**Third, Fifth, and Sixth MLS photo's are virtually rendered showing the potential of an off white painted exterior if painted**A rare opportunity to own a piece of Winter Park history in the coveted College Quarter. Built in 1922 and recognized as a designated historic residence, 318 Vitoria Avenue is a distinctive Mission Revival home offering timeless architecture, remarkable craftsmanship, and an exceptional lifestyle near Lake Virginia, Rollins College, and Park Avenue. Set on an elevated homesite along one of Winter Park’s picturesque brick streets, this 3-bedroom, 2.5-bath residence offers 2,036 square feet thoughtfully oriented to embrace natural light and breezes from nearby Lake Virginia. Its Mission Revival architecture is showcased through graceful arches, classic stucco construction, barrel-tile accents, distinctive balconies, and a secluded courtyard framed by custom ironwork created by a local master craftsman. Inside, original oak and heart-pine floors preserve more than a century of character. The expansive great room serves as the heart of the home, featuring 10-foot exposed-rafter ceilings, dramatic arched windows with handblown glass, a wood-burning fireplace, and French doors that create a seamless connection to the courtyard and pool. The kitchen features an oversized butcher-block island, imported tile, oak cabinetry, a breakfast nook, and adjoining pantry and laundry areas. Uniques details continue with custom coquina flooring on the porch and intricate tilework in the Florida room, both created by a Disney Imagineer and adding an exceptional layer of artistry and one-of-a-kind craftsmanship to the home. Upstairs, three bedrooms feature original heart-pine flooring, abundant natural light, built-in storage, balconies, and select views toward Lake Virginia. An unfinished basement provides valuable additional storage—an uncommon feature in Central Florida. Thoughtful improvements complement the home’s historic character, including a roof completed in 2021, air-conditioning system installed in 2020, recently updated tankless water heater, and a 2026 electrical panel upgrade with whole-home surge protection. Outside, mature landscaping surrounds the private plunge pool and courtyard, creating an intimate setting for relaxing and entertaining. College Quarter residents enjoy exclusive access to a private neighborhood park and dock on Lake Virginia, providing a wonderful connection to kayaking, paddleboarding, boating, and Winter Park’s Chain of Lakes. Rollins College, Park Avenue, Central Park, museums, restaurants, boutiques, and many of the city’s most celebrated destinations are all close at hand. Held by the same family for 46 years, 318 Vitoria Avenue represents a rare convergence of historic architecture, bespoke craftsmanship, meaningful modern improvements, private outdoor living, lake access, and an extraordinary Winter Park location. A distinctive residence ready for its next chapter.

3 Beds ⋅ 3 Baths ⋅ College Place Rep SubDv. ⋅ 32789 Zip Code

**Third, Fifth, and Sixth MLS photo's are virtually rendered showing the potential of an off white painted exterior if painted**A rare opportunity to own a piece of Winter Park history in the coveted College Quarter. Built in 1922 and recognized as a designated historic residence, 318 Vitoria Avenue is a distinctive Mission Revival home offering timeless architecture, remarkable craftsmanship, and an exceptional lifestyle near Lake Virginia, Rollins College, and Park Avenue. Set on an elevated homesite along one of Winter Park’s picturesque brick streets, this 3-bedroom, 2.5-bath residence offers 2,036 square feet thoughtfully oriented to embrace natural light and breezes from nearby Lake Virginia. Its Mission Revival architecture is showcased through graceful arches, classic stucco construction, barrel-tile accents, distinctive balconies, and a secluded courtyard framed by custom ironwork created by a local master craftsman. Inside, original oak and heart-pine floors preserve more than a century of character. The expansive great room serves as the heart of the home, featuring 10-foot exposed-rafter ceilings, dramatic arched windows with handblown glass, a wood-burning fireplace, and French doors that create a seamless connection to the courtyard and pool. The kitchen features an oversized butcher-block island, imported tile, oak cabinetry, a breakfast nook, and adjoining pantry and laundry areas. Uniques details continue with custom coquina flooring on the porch and intricate tilework in the Florida room, both created by a Disney Imagineer and adding an exceptional layer of artistry and one-of-a-kind craftsmanship to the home. Upstairs, three bedrooms feature original heart-pine flooring, abundant natural light, built-in storage, balconies, and select views toward Lake Virginia. An unfinished basement provides valuable additional storage—an uncommon feature in Central Florida. Thoughtful improvements complement the home’s historic character, including a roof completed in 2021, air-conditioning system installed in 2020, recently updated tankless water heater, and a 2026 electrical panel upgrade with whole-home surge protection. Outside, mature landscaping surrounds the private plunge pool and courtyard, creating an intimate setting for relaxing and entertaining. College Quarter residents enjoy exclusive access to a private neighborhood park and dock on Lake Virginia, providing a wonderful connection to kayaking, paddleboarding, boating, and Winter Park’s Chain of Lakes. Rollins College, Park Avenue, Central Park, museums, restaurants, boutiques, and many of the city’s most celebrated destinations are all close at hand. Held by the same family for 46 years, 318 Vitoria Avenue represents a rare convergence of historic architecture, bespoke craftsmanship, meaningful modern improvements, private outdoor living, lake access, and an extraordinary Winter Park location. A distinctive residence ready for its next chapter.

318 Vitoria Avenue, Winter Park

$510,000

Excellent Winter Park location! This 3 bedroom 2.5 bath quad-condo LIVES LIKE A PRIVATE 2-STORY HOME, with attached oversized 2 car garage, private patio and back fenced area. (The unit is attached to another only by a common garage wall.) Priced below market value to be sold AS-IS for the seller's convenience and TLC needed. ** One Year AHS Home Warranty included.** Nestled between Denning Dr and Orlando Ave, this home is an easy walk to the vibrant charm of Park Avenue, and close to the Winter Park Library, SunRail, and Rollins College. Publix and restaurants are just down the street! The first floor is tiled, with foyer entry, and comfortable family/dining/kitchen living area complete with fireplace. Sliding doors lead to a private patio. Upstairs, the large primary suite is a nice retreat with high ceilings, double walk in closets, double vanity and ample sized shower. Two more bedrooms and another bath complete the 2nd floor. High end washer and dryer are included in the attached garage, and a full wall workshop is in the garage too. Call to see it today!

3 Beds ⋅ 3 Baths ⋅ Villas Of Aragon Condo SubDv. ⋅ 32789 Zip Code

Excellent Winter Park location! This 3 bedroom 2.5 bath quad-condo LIVES LIKE A PRIVATE 2-STORY HOME, with attached oversized 2 car garage, private patio and back fenced area. (The unit is attached to another only by a common garage wall.) Priced below market value to be sold AS-IS for the seller's convenience and TLC needed. ** One Year AHS Home Warranty included.** Nestled between Denning Dr and Orlando Ave, this home is an easy walk to the vibrant charm of Park Avenue, and close to the Winter Park Library, SunRail, and Rollins College. Publix and restaurants are just down the street! The first floor is tiled, with foyer entry, and comfortable family/dining/kitchen living area complete with fireplace. Sliding doors lead to a private patio. Upstairs, the large primary suite is a nice retreat with high ceilings, double walk in closets, double vanity and ample sized shower. Two more bedrooms and another bath complete the 2nd floor. High end washer and dryer are included in the attached garage, and a full wall workshop is in the garage too. Call to see it today!

1061 Aragon Avenue Unit 1061, Winter Park

$1,450,000

RARE & GORGEOUS MEDITERRANEAN ESTATE located on a private, OVERSIZED CUL-DE-SAC LOT in Talman Mews, featuring a heated pool and spa with waterfall and water features, private office, loft, bonus/game room, and home gym room. Custom double wood doors open to a breathtaking two-story foyer with a motorized chandelier lift, curved staircase, and private elevator that goes up to the second floor. The first level features 10-foot ceilings, travertine flooring, custom columns, and crown molding in the formal living spaces. The kitchen is outfitted with upscale appliances including a Thermador separate paneled refrigerator and freezer, 6-burner gas range, chef style built-in microwave and convection oven, two paneled dishwashers, exotic granite countertops, center island, and custom walk-in pantry. The family room, anchored by a gas fireplace, opens through French doors to a covered lanai and resort-style backyard. A game room with a pool table and full en-suite bath can function as a second primary suite or in-law retreat, and a first-floor bedroom adds flexibility for guests or remote work. The garage's third bay was converted to be used as a home gym, with the option to reconvert for additional vehicle storage. Upstairs, every bedroom has a private en-suite bath. The primary suite includes a tray ceiling, sitting area, wet bar, private large sized balcony (great place to watch the rocket launches!) and it also has direct stair access downstairs to the pool. The primary bath features a jetted garden tub, gorgeous columns, separate walk-in shower, custom wood cabinetry with granite countertops, and an oversized walk-in closet. A loft, private study, upstairs laundry room, and additional bedrooms (one with its own sitting area) complete the second floor. The backyard includes tropical landscaping, vinyl privacy fencing, a heated pool and spa with water features, and a covered lanai pre-plumbed for a future summer kitchen. Additional features include a side-entry garage with epoxy flooring and workbench, barrel tile roof with radiant barrier, double-pane thermal windows, tankless water heater, security system, and surround sound pre-wire. Located 5 minutes from the prestigious Trinity Preparatory School. This home offers easy access to Downtown Winter Park, Downtown Orlando, UCF, Orlando International Airport, premier shopping, dining, and entertainment, the perfect blend of luxury, comfort, and convenience. THIS HOME REPRESENTS THE FINEST OF WINTER PARK LIVING!

4 Beds ⋅ 5 Baths ⋅ Talman Mews Ph 2 SubDv. ⋅ 32792 Zip Code

RARE & GORGEOUS MEDITERRANEAN ESTATE located on a private, OVERSIZED CUL-DE-SAC LOT in Talman Mews, featuring a heated pool and spa with waterfall and water features, private office, loft, bonus/game room, and home gym room. Custom double wood doors open to a breathtaking two-story foyer with a motorized chandelier lift, curved staircase, and private elevator that goes up to the second floor. The first level features 10-foot ceilings, travertine flooring, custom columns, and crown molding in the formal living spaces. The kitchen is outfitted with upscale appliances including a Thermador separate paneled refrigerator and freezer, 6-burner gas range, chef style built-in microwave and convection oven, two paneled dishwashers, exotic granite countertops, center island, and custom walk-in pantry. The family room, anchored by a gas fireplace, opens through French doors to a covered lanai and resort-style backyard. A game room with a pool table and full en-suite bath can function as a second primary suite or in-law retreat, and a first-floor bedroom adds flexibility for guests or remote work. The garage's third bay was converted to be used as a home gym, with the option to reconvert for additional vehicle storage. Upstairs, every bedroom has a private en-suite bath. The primary suite includes a tray ceiling, sitting area, wet bar, private large sized balcony (great place to watch the rocket launches!) and it also has direct stair access downstairs to the pool. The primary bath features a jetted garden tub, gorgeous columns, separate walk-in shower, custom wood cabinetry with granite countertops, and an oversized walk-in closet. A loft, private study, upstairs laundry room, and additional bedrooms (one with its own sitting area) complete the second floor. The backyard includes tropical landscaping, vinyl privacy fencing, a heated pool and spa with water features, and a covered lanai pre-plumbed for a future summer kitchen. Additional features include a side-entry garage with epoxy flooring and workbench, barrel tile roof with radiant barrier, double-pane thermal windows, tankless water heater, security system, and surround sound pre-wire. Located 5 minutes from the prestigious Trinity Preparatory School. This home offers easy access to Downtown Winter Park, Downtown Orlando, UCF, Orlando International Airport, premier shopping, dining, and entertainment, the perfect blend of luxury, comfort, and convenience. THIS HOME REPRESENTS THE FINEST OF WINTER PARK LIVING!

2138 Talman Court, Winter Park

$1,894,400

Welcome to 2614 Parkland Drive. This is your chance to own a showpiece location with zoned for the coveted Audubon Park K-8 and Winter Park High School districts.

Parklando 03 SubDv. ⋅ 32789 Zip Code

Welcome to 2614 Parkland Drive. This is your chance to own a showpiece location with zoned for the coveted Audubon Park K-8 and Winter Park High School districts.

2614 Parkland Drive, Winter Park

$429,000

Rare opportunity in Winter Park's 32789! Located on a quiet cul-de-sac in one of Central Florida's most sought-after ZIP codes, this spacious 4-bedroom, 2-bath home offers approximately 2,400 square feet of living space, a brand new roof (2025), water heater (2021), and is situated on a generous lot with no HOA. Whether you're dreaming of creating your forever home, searching for your next renovation project, or looking to add a prime rental property to your portfolio, this is one you won't want to miss. With a little vision and updating, this property can truly shine in a neighborhood where beautifully renovated homes and stunning new construction continue to elevate property values. The location is exceptional—minutes from Park Avenue, Winter Park Village, top-rated schools, Rollins College, AdventHealth, downtown Orlando, and convenient access to I-4 and SR 408. Enjoy some of Central Florida's finest dining, boutique shopping, parks, museums, and entertainment, all just moments from your doorstep. Families will also appreciate Killarney Elementary School is just one street away. With endless possibilities to reimagine, renovate, or invest, opportunities to purchase a home like this seldom come along. If you're looking to build equity, generate rental income, or create the home you've always envisioned, this exceptional property is ready for its next chapter.

4 Beds ⋅ 2 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Rare opportunity in Winter Park's 32789! Located on a quiet cul-de-sac in one of Central Florida's most sought-after ZIP codes, this spacious 4-bedroom, 2-bath home offers approximately 2,400 square feet of living space, a brand new roof (2025), water heater (2021), and is situated on a generous lot with no HOA. Whether you're dreaming of creating your forever home, searching for your next renovation project, or looking to add a prime rental property to your portfolio, this is one you won't want to miss. With a little vision and updating, this property can truly shine in a neighborhood where beautifully renovated homes and stunning new construction continue to elevate property values. The location is exceptional—minutes from Park Avenue, Winter Park Village, top-rated schools, Rollins College, AdventHealth, downtown Orlando, and convenient access to I-4 and SR 408. Enjoy some of Central Florida's finest dining, boutique shopping, parks, museums, and entertainment, all just moments from your doorstep. Families will also appreciate Killarney Elementary School is just one street away. With endless possibilities to reimagine, renovate, or invest, opportunities to purchase a home like this seldom come along. If you're looking to build equity, generate rental income, or create the home you've always envisioned, this exceptional property is ready for its next chapter.

2323 Devon Court, Winter Park

$399,000

Step into this beautifully designed townhome featuring an open-concept kitchen, dining, and living area—perfect for everyday living and entertaining. The modern kitchen boasts stainless steel appliances, gray cabinetry, and quartz countertops. Upstairs, the spacious primary suite offers a walk-in closet and a private in-suite bath with dual quartz vanities, while two additional bedrooms, a full bath, and a convenient laundry closet complete the second floor. Relax on the covered lanai and enjoy the privacy of this home's cul-de-sac location. The HOA includes landscaping, exterior maintenance and repairs, high-speed internet, and access to the gated community, providing low-maintenance living. With no CDD, this home is an excellent option for both homeowners and investors. Ideally located in highly desirable Winter Park, Grayson Square is just minutes from SR-436, SR-434, and SR-417, with Publix, Starbucks, shopping, dining, and top-rated Seminole County schools nearby. Park Avenue is only a short drive away, making this home the perfect combination of convenience, comfort, and value.

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code

Step into this beautifully designed townhome featuring an open-concept kitchen, dining, and living area—perfect for everyday living and entertaining. The modern kitchen boasts stainless steel appliances, gray cabinetry, and quartz countertops. Upstairs, the spacious primary suite offers a walk-in closet and a private in-suite bath with dual quartz vanities, while two additional bedrooms, a full bath, and a convenient laundry closet complete the second floor. Relax on the covered lanai and enjoy the privacy of this home's cul-de-sac location. The HOA includes landscaping, exterior maintenance and repairs, high-speed internet, and access to the gated community, providing low-maintenance living. With no CDD, this home is an excellent option for both homeowners and investors. Ideally located in highly desirable Winter Park, Grayson Square is just minutes from SR-436, SR-434, and SR-417, with Publix, Starbucks, shopping, dining, and top-rated Seminole County schools nearby. Park Avenue is only a short drive away, making this home the perfect combination of convenience, comfort, and value.

2033 Canny Cove, Winter Park

$280,000

Turnkey Charm in Winter Park! This beautifully remodeled 3-bedroom, 2-bathroom home offers the perfect blend of style and convenience. Step inside to find durable ceramic tile flooring flowing through a spacious family room, perfect for entertaining. The home features a 1-car garage with a functional laundry area equipped with a washer and dryer tucked neatly in the back, alongside a fantastic outdoor setup. Relax on your open, screened-in patio overlooking a massive, fully fenced backyard. Freshly updated inside and out, this move-in-ready gem is ready for its next owner!

3 Beds ⋅ 2 Baths ⋅ Coronation Add SubDv. ⋅ 32792 Zip Code

Turnkey Charm in Winter Park! This beautifully remodeled 3-bedroom, 2-bathroom home offers the perfect blend of style and convenience. Step inside to find durable ceramic tile flooring flowing through a spacious family room, perfect for entertaining. The home features a 1-car garage with a functional laundry area equipped with a washer and dryer tucked neatly in the back, alongside a fantastic outdoor setup. Relax on your open, screened-in patio overlooking a massive, fully fenced backyard. Freshly updated inside and out, this move-in-ready gem is ready for its next owner!

3321 Royal Street, Winter Park

$1,275,000

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 230 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable homesite with private lake access and the ability to build your own dock.

3 Beds ⋅ 3 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 230 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable homesite with private lake access and the ability to build your own dock.

240 Killarney Drive, Winter Park

$1,250,000

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 240 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable corner homesite with private lake access and the ability to build your own dock.

4 Beds ⋅ 1 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 240 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable corner homesite with private lake access and the ability to build your own dock.

230 Killarney Drive, Winter Park

$920,000

Experience refined Florida living in this exceptional single-story residence, ideally situated on a quiet cul-de-sac within an intimate gated community in one of Winter Park's most desirable locations. Impeccably maintained, this elegant home offers over 3,000 square feet of thoughtfully designed living space with 4 bedrooms, 3 full baths, a private office, and a desirable three-way split floor plan that provides both privacy and flexibility. Designed for comfortable everyday living and effortless entertaining, the home features formal living and dining rooms, a spacious family room, and a bright breakfast area. The stunning gourmet kitchen is the heart of the home, showcasing timeless white cabinetry, quartz countertops, abundant prep space, a convenient butler's pantry, and an open flow to the main living areas. The generous primary suite offers a spacious walk-in closet and a luxurious retreat, while quality finishes and meticulous attention to detail are evident throughout. Enjoy year-round outdoor living on the private screened lanai, perfect for relaxing or entertaining. Additional highlights include a three-car garage, a durable tile roof, and a fully paid solar energy system, keeping the average monthly electric bill under $100. Combining elegance, energy efficiency, and an outstanding location, this move-in-ready home offers the perfect balance of luxury, comfort, and convenience.

4 Beds ⋅ 3 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code

Experience refined Florida living in this exceptional single-story residence, ideally situated on a quiet cul-de-sac within an intimate gated community in one of Winter Park's most desirable locations. Impeccably maintained, this elegant home offers over 3,000 square feet of thoughtfully designed living space with 4 bedrooms, 3 full baths, a private office, and a desirable three-way split floor plan that provides both privacy and flexibility. Designed for comfortable everyday living and effortless entertaining, the home features formal living and dining rooms, a spacious family room, and a bright breakfast area. The stunning gourmet kitchen is the heart of the home, showcasing timeless white cabinetry, quartz countertops, abundant prep space, a convenient butler's pantry, and an open flow to the main living areas. The generous primary suite offers a spacious walk-in closet and a luxurious retreat, while quality finishes and meticulous attention to detail are evident throughout. Enjoy year-round outdoor living on the private screened lanai, perfect for relaxing or entertaining. Additional highlights include a three-car garage, a durable tile roof, and a fully paid solar energy system, keeping the average monthly electric bill under $100. Combining elegance, energy efficiency, and an outstanding location, this move-in-ready home offers the perfect balance of luxury, comfort, and convenience.

1492 Via Sangro Pl, Winter Park

$1,150,000

Located on one of Winter Park's picturesque brick streets in the highly desirable “Tree Streets”, this beautifully updated home offers incredible curb appeal with a circular driveway, charming front porch with brick flooring, and mature landscaping. Inside, a spacious foyer with soaring ceilings welcomes you, while engineered hardwood flooring runs throughout the main living areas. The recently renovated kitchen is the heart of the home, featuring quartz countertops, custom oak cabinetry with gold hardware, a center island with seating, stylish backsplash, and stainless steel appliances, including a gas range. The kitchen opens to the spacious dining room and inviting family room with built-ins, high ceilings, and French doors that fill the space with natural light. One of the home's most unique features is its thoughtfully designed layout. The original 1951 portion of the home offers two bedrooms, including the original primary suite with a large walk-in closet and private bath, plus a beautifully renovated hall bathroom. An addition completed in the early 2000s created an impressive owner's retreat on the opposite side of the home, complete with vaulted ceilings, French doors to the backyard, an oversized walk-in closet with custom organization, and a spacious bathroom with double vanities, soaking tub, separate shower, and private water closet. A fourth bedroom, tucked away in its own wing off the dining room, features built-ins, a large walk-in closet, and is conveniently located near the indoor laundry room. Situated on a generous .24-acre lot, the backyard offers plenty of room to add a pool while still leaving space to enjoy the yard. A long driveway leads to the rear one-car carport and an oversized storage room. Major updates include a 2020 roof and 2021 AC. All of this is just minutes from Park Avenue's renowned shopping, dining, and events, with easy access to top-rated Winter Park schools, parks, and everything that makes this neighborhood one of Central Florida's most sought-after places to call home.

4 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace 2nd Add SubDv. ⋅ 32789 Zip Code

Located on one of Winter Park's picturesque brick streets in the highly desirable “Tree Streets”, this beautifully updated home offers incredible curb appeal with a circular driveway, charming front porch with brick flooring, and mature landscaping. Inside, a spacious foyer with soaring ceilings welcomes you, while engineered hardwood flooring runs throughout the main living areas. The recently renovated kitchen is the heart of the home, featuring quartz countertops, custom oak cabinetry with gold hardware, a center island with seating, stylish backsplash, and stainless steel appliances, including a gas range. The kitchen opens to the spacious dining room and inviting family room with built-ins, high ceilings, and French doors that fill the space with natural light. One of the home's most unique features is its thoughtfully designed layout. The original 1951 portion of the home offers two bedrooms, including the original primary suite with a large walk-in closet and private bath, plus a beautifully renovated hall bathroom. An addition completed in the early 2000s created an impressive owner's retreat on the opposite side of the home, complete with vaulted ceilings, French doors to the backyard, an oversized walk-in closet with custom organization, and a spacious bathroom with double vanities, soaking tub, separate shower, and private water closet. A fourth bedroom, tucked away in its own wing off the dining room, features built-ins, a large walk-in closet, and is conveniently located near the indoor laundry room. Situated on a generous .24-acre lot, the backyard offers plenty of room to add a pool while still leaving space to enjoy the yard. A long driveway leads to the rear one-car carport and an oversized storage room. Major updates include a 2020 roof and 2021 AC. All of this is just minutes from Park Avenue's renowned shopping, dining, and events, with easy access to top-rated Winter Park schools, parks, and everything that makes this neighborhood one of Central Florida's most sought-after places to call home.

1351 Oneco Avenue, Winter Park

$175,000

Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping! One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional Built-in Closets, Vanity and Mirrored Closets and updated Bath, accessible for Guests and close to Master! Updated Windows! Private Balcony! Owner is providing a One-Year Home Warranty and a $3,000 Flooring Credit. Make this affordable Unit your own!

1 Beds ⋅ 1 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping! One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional Built-in Closets, Vanity and Mirrored Closets and updated Bath, accessible for Guests and close to Master! Updated Windows! Private Balcony! Owner is providing a One-Year Home Warranty and a $3,000 Flooring Credit. Make this affordable Unit your own!

1500 Gay Road Unit 4D, Winter Park

$575,000

Welcome to this beautifully maintained and thoughtfully updated home in the desirable City of Winter Park, offering an exceptional blend of comfort, space, and convenience. From the moment you arrive, the freshly installed, vibrant green front lawn and attractive landscaping create an inviting first impression. Inside, the cathedral ceiling enhances the spacious feel of the open floor plan, complemented by luxury vinyl flooring and ceramic tile throughout. The well-appointed kitchen features white cabinetry, granite countertops, and a new stainless steel appliance package that adds a modern touch. The home's versatile layout offers plenty of room for everyday living and entertaining, including a separate family room, a bright Florida Room, and a dedicated office or exercise room equipped with an energy-efficient mini-split system and convenient access to the carport. The inside utility room includes a full-size washer and dryer, as well as a second side-by-side refrigerator for added storage and convenience. The spacious primary bedroom provides a comfortable retreat with a private bath featuring maple cabinetry, ample vanity storage, and a roomy walk-in shower. The guest bath offers a tub/shower combination. Step outside to enjoy the spacious, fully fenced backyard—perfect for relaxing, entertaining, gardening, or enjoying the Florida sunshine. Additional features include a storage shed, sprinkler system supplied by a separate well, and a one-car carport with parking for up to three additional vehicles. Major updates include an AC system replaced in 2017, a new roof and electrical panel in 2019, and replumbing completed in 2019. Best of all, you are walking distance to Winter Park High School and just minutes from local dining, shopping, and everyday conveniences. With its spacious floor plan, flexible living areas, attractive updates, generous outdoor space, and prime Winter Park location, this home is a must-see. Schedule your private showing today! Buyer/buyer's agent to verify all schools and room measurements. Appliances convey as is. Brio Management LLC, Seller, is owned by 2 Florida Licensed Real Estate Brokers.

3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 07 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully maintained and thoughtfully updated home in the desirable City of Winter Park, offering an exceptional blend of comfort, space, and convenience. From the moment you arrive, the freshly installed, vibrant green front lawn and attractive landscaping create an inviting first impression. Inside, the cathedral ceiling enhances the spacious feel of the open floor plan, complemented by luxury vinyl flooring and ceramic tile throughout. The well-appointed kitchen features white cabinetry, granite countertops, and a new stainless steel appliance package that adds a modern touch. The home's versatile layout offers plenty of room for everyday living and entertaining, including a separate family room, a bright Florida Room, and a dedicated office or exercise room equipped with an energy-efficient mini-split system and convenient access to the carport. The inside utility room includes a full-size washer and dryer, as well as a second side-by-side refrigerator for added storage and convenience. The spacious primary bedroom provides a comfortable retreat with a private bath featuring maple cabinetry, ample vanity storage, and a roomy walk-in shower. The guest bath offers a tub/shower combination. Step outside to enjoy the spacious, fully fenced backyard—perfect for relaxing, entertaining, gardening, or enjoying the Florida sunshine. Additional features include a storage shed, sprinkler system supplied by a separate well, and a one-car carport with parking for up to three additional vehicles. Major updates include an AC system replaced in 2017, a new roof and electrical panel in 2019, and replumbing completed in 2019. Best of all, you are walking distance to Winter Park High School and just minutes from local dining, shopping, and everyday conveniences. With its spacious floor plan, flexible living areas, attractive updates, generous outdoor space, and prime Winter Park location, this home is a must-see. Schedule your private showing today! Buyer/buyer's agent to verify all schools and room measurements. Appliances convey as is. Brio Management LLC, Seller, is owned by 2 Florida Licensed Real Estate Brokers.

2010 Summerfield Road, Winter Park

$4,900,000

A pristine location in the Vias of Winter Park, this refined Santa Barbara-inspired Mediterranean estate rests on nearly half an acre — a rare double lot. A 2006 custom build by Maroon Fine Homes and renovated in 2024 by Greg Hardwick, this estate blends timeless architecture with comfortable sophistication and functionality. A stone’s throw to the celebrated shops and dining of Park Avenue, Rollins College, Winter Park Golf Course, and the serene beauty of Kraft Azalea Gardens, the location is simply unrivaled. This extraordinary residence spans nearly 5,000 sf with a flowing floor plan designed for entertaining and everyday living. Solid wood artisan arched doors anchor the inviting foyer with porcelain marble tile, volume ceilings, and a sleek iron circular staircase as a focal point. An open dining and intimate living room layout are flanked by windows and clear view doors, which bring in natural light. The spaces share a unique temperature-controlled wine cellar finished with seamless glass and ambient lighting, adding a dramatic touch for the discerning enthusiast. The main level centers around a spacious kitchen that enjoys a dedicated eat-in space and counter seating, with a family room that overlooks the expansive backyard. A dedicated wet bar and first-floor bonus room make this home ideal for hosting at any scale. The outdoor living rivals a 5-star resort, recently reimagined in 2026 by Signature Landscaping. An immense new pool with a sun shelf anchors the outdoor living experience, surrounded by a lush turf courtyard, sport court, and a covered lanai with generous pavered decking and a summer kitchen. A cozy gas fire pit with casual seating invites you to take in the evening breezes. Privacy abounds with mature Japanese blueberry trees and Podocarpus hedges. A dedicated side yard dog run completes this outdoor haven. The main floor is home to the first-floor primary suite, with privacy doors separating this section of the home. It is a true retreat unto itself, offering a sunlit sitting area with doors leading to the backyard, a beautifully appointed bath, a dedicated home office, and two custom-fitted walk-in closets, one of which includes a secondary laundry area. The spa-inspired bathroom has it all, featuring a generous shower with a soaking tub within the enclosure for the ultimate relaxation experience. A first-floor guest suite, thoughtfully designed with a split-plan layout, provides privacy for visitors, while three additional ensuite bedrooms and a bonus landing are located upstairs. The oversized three-car side-loading garage is air-conditioned and features upgraded flooring, while a generous circular drive and mature front hedge offer a gracious arrival experience and an added layer of privacy. A rare convergence of premier location, architectural distinction, and meticulous renovation — this is Winter Park luxury living at its finest.

5 Beds ⋅ 6 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code

A pristine location in the Vias of Winter Park, this refined Santa Barbara-inspired Mediterranean estate rests on nearly half an acre — a rare double lot. A 2006 custom build by Maroon Fine Homes and renovated in 2024 by Greg Hardwick, this estate blends timeless architecture with comfortable sophistication and functionality. A stone’s throw to the celebrated shops and dining of Park Avenue, Rollins College, Winter Park Golf Course, and the serene beauty of Kraft Azalea Gardens, the location is simply unrivaled. This extraordinary residence spans nearly 5,000 sf with a flowing floor plan designed for entertaining and everyday living. Solid wood artisan arched doors anchor the inviting foyer with porcelain marble tile, volume ceilings, and a sleek iron circular staircase as a focal point. An open dining and intimate living room layout are flanked by windows and clear view doors, which bring in natural light. The spaces share a unique temperature-controlled wine cellar finished with seamless glass and ambient lighting, adding a dramatic touch for the discerning enthusiast. The main level centers around a spacious kitchen that enjoys a dedicated eat-in space and counter seating, with a family room that overlooks the expansive backyard. A dedicated wet bar and first-floor bonus room make this home ideal for hosting at any scale. The outdoor living rivals a 5-star resort, recently reimagined in 2026 by Signature Landscaping. An immense new pool with a sun shelf anchors the outdoor living experience, surrounded by a lush turf courtyard, sport court, and a covered lanai with generous pavered decking and a summer kitchen. A cozy gas fire pit with casual seating invites you to take in the evening breezes. Privacy abounds with mature Japanese blueberry trees and Podocarpus hedges. A dedicated side yard dog run completes this outdoor haven. The main floor is home to the first-floor primary suite, with privacy doors separating this section of the home. It is a true retreat unto itself, offering a sunlit sitting area with doors leading to the backyard, a beautifully appointed bath, a dedicated home office, and two custom-fitted walk-in closets, one of which includes a secondary laundry area. The spa-inspired bathroom has it all, featuring a generous shower with a soaking tub within the enclosure for the ultimate relaxation experience. A first-floor guest suite, thoughtfully designed with a split-plan layout, provides privacy for visitors, while three additional ensuite bedrooms and a bonus landing are located upstairs. The oversized three-car side-loading garage is air-conditioned and features upgraded flooring, while a generous circular drive and mature front hedge offer a gracious arrival experience and an added layer of privacy. A rare convergence of premier location, architectural distinction, and meticulous renovation — this is Winter Park luxury living at its finest.

1180 Via Lugano, Winter Park

$799,900

JUST REDUCED! Impeccably Renovated Turn-Key Oasis with a Resort-Style Backyard! No HOA with yard large enough for possible ADU. Welcome home to this meticulously updated 4-bedroom, 3-bathroom residence where true pride of ownership shines through every detail. Absolutely turn-key and loaded with premium updates throughout, such as new electrical panel, newer water heater, new pool pavers, upgraded engineered floors throughout & much more! This home offers the perfect blend of modern luxury and effortless entertaining.The heart of the home seamlessly connects to the outdoors with a brilliant kitchen pass-through window, serving an enormous covered patio. Step into your own private, tranquil backyard oasis featuring a freshly resurfaced pool surrounded by stunning new pavers & large Perolga. Whether you are hosting a summer barbecue or rinsing off in your convenient outdoor shower after a swim, this backyard is built for Florida living at its finest. Property is zoned for highly rated schools with convenient location just moments away from Cady Way Park & trails, Rollins, UCF, & Full Sail Colleges, just 4 miles from vibrant dining(Park Ave) & premier shopping.

4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

JUST REDUCED! Impeccably Renovated Turn-Key Oasis with a Resort-Style Backyard! No HOA with yard large enough for possible ADU. Welcome home to this meticulously updated 4-bedroom, 3-bathroom residence where true pride of ownership shines through every detail. Absolutely turn-key and loaded with premium updates throughout, such as new electrical panel, newer water heater, new pool pavers, upgraded engineered floors throughout & much more! This home offers the perfect blend of modern luxury and effortless entertaining.The heart of the home seamlessly connects to the outdoors with a brilliant kitchen pass-through window, serving an enormous covered patio. Step into your own private, tranquil backyard oasis featuring a freshly resurfaced pool surrounded by stunning new pavers & large Perolga. Whether you are hosting a summer barbecue or rinsing off in your convenient outdoor shower after a swim, this backyard is built for Florida living at its finest. Property is zoned for highly rated schools with convenient location just moments away from Cady Way Park & trails, Rollins, UCF, & Full Sail Colleges, just 4 miles from vibrant dining(Park Ave) & premier shopping.

722 S Ranger Boulevard, Winter Park

$285,000

Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland. This inviting home features a versatile upstairs loft overlooking the living and dining areas—perfect for a home office, fitness space, craft room, or additional guest accommodations. The bright, cheerful eat-in kitchen is both stylish and functional, showcasing quartz countertops, a glass tile backsplash, abundant cabinetry, a pull-out spice rack, trash/recycling cabinet, and a built-in storage unit. Sliding glass doors open to the private front courtyard, filling the space with natural light. Conveniently located laundry area, complete with washer and dryer, is tucked within the kitchen. The spacious living room features a cozy wood-burning fireplace and flows seamlessly into the dining area beneath soaring vaulted ceilings accented by skylights. Sliding glass doors lead to a screened lanai with a slate tile floor and a storage closet—an ideal spot to relax and enjoy Florida living. The primary suite also opens directly to the lanai and offers a beautifully renovated en-suite bath with a luxurious walk-in shower, updated vanity, linen cabinet, and a custom walk-in closet with built-in organizers. The front bedroom also includes a generous walk-in closet. Enjoy added privacy with a picturesque, tree-lined green space across the street rather than neighboring condos directly in front. Two dedicated parking spaces are conveniently located just outside your door. Cedarwood Village offers an exceptional location directly across from Casselberry Commons Shopping Plaza and is just minutes from Full Sail University, UCF, and Rollins College. Residents enjoy a community swimming pool, tennis courts with pickleball lines, and designated dog-walking areas. Additional highlights include a new roof and skylights installed in 2020. Monthly HOA fees cover exterior maintenance, lawn care, and community amenities, making this the perfect opportunity to enjoy carefree living in one of the area's most desirable communities.

2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland. This inviting home features a versatile upstairs loft overlooking the living and dining areas—perfect for a home office, fitness space, craft room, or additional guest accommodations. The bright, cheerful eat-in kitchen is both stylish and functional, showcasing quartz countertops, a glass tile backsplash, abundant cabinetry, a pull-out spice rack, trash/recycling cabinet, and a built-in storage unit. Sliding glass doors open to the private front courtyard, filling the space with natural light. Conveniently located laundry area, complete with washer and dryer, is tucked within the kitchen. The spacious living room features a cozy wood-burning fireplace and flows seamlessly into the dining area beneath soaring vaulted ceilings accented by skylights. Sliding glass doors lead to a screened lanai with a slate tile floor and a storage closet—an ideal spot to relax and enjoy Florida living. The primary suite also opens directly to the lanai and offers a beautifully renovated en-suite bath with a luxurious walk-in shower, updated vanity, linen cabinet, and a custom walk-in closet with built-in organizers. The front bedroom also includes a generous walk-in closet. Enjoy added privacy with a picturesque, tree-lined green space across the street rather than neighboring condos directly in front. Two dedicated parking spaces are conveniently located just outside your door. Cedarwood Village offers an exceptional location directly across from Casselberry Commons Shopping Plaza and is just minutes from Full Sail University, UCF, and Rollins College. Residents enjoy a community swimming pool, tennis courts with pickleball lines, and designated dog-walking areas. Additional highlights include a new roof and skylights installed in 2020. Monthly HOA fees cover exterior maintenance, lawn care, and community amenities, making this the perfect opportunity to enjoy carefree living in one of the area's most desirable communities.

2372 Sun Valley Circle Unit 2372, Winter Park

$1,625,000

Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exceptional 4-bedroom, 4-bath pool home with a dedicated office offers timeless design, thoughtful updates, and an unbeatable location. A welcoming covered front porch provides the perfect spot to enjoy your morning coffee. Inside, soaring ceilings, extensive moldings, travertine and hardwood floors, and abundant natural light create an elegant first impression. Just off the foyer, French doors open to a private office, ideal for working from home. A secondary bedroom and full bath with a walk-in shower are conveniently located on the main level. The spacious kitchen flows seamlessly into the family room and features granite countertops, solid wood soft-close cabinetry, a gas cooktop, wall oven, breakfast bar, wet bar, walk-in pantry, and a sunny breakfast nook overlooking the lanai and pool. The adjoining family room is anchored by a gas fireplace and French doors leading outdoors. The covered lanai showcases a tongue-and-groove ceiling and remote-controlled screens, creating the perfect setting for year-round entertaining. The generous first-floor primary suite offers space for a sitting area and features two custom walk-in closets, dual vanities, a soaking tub, separate shower, and private water closet. A beautiful wrought-iron staircase leads upstairs to two generous en-suite bedrooms and a cozy loft. The private backyard is designed for relaxation and entertaining, featuring a saltwater pool and spa surrounded by lush landscaping. Additional highlights include two newer HVAC systems (2022 and 2023), a gas water heater (2022), central vacuum system, built-in Home Team pest defense system, and plantation shutters throughout. Located within the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home is ideally situated between Park Avenue and Corrine Drive, with downtown Orlando just minutes away.

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exceptional 4-bedroom, 4-bath pool home with a dedicated office offers timeless design, thoughtful updates, and an unbeatable location. A welcoming covered front porch provides the perfect spot to enjoy your morning coffee. Inside, soaring ceilings, extensive moldings, travertine and hardwood floors, and abundant natural light create an elegant first impression. Just off the foyer, French doors open to a private office, ideal for working from home. A secondary bedroom and full bath with a walk-in shower are conveniently located on the main level. The spacious kitchen flows seamlessly into the family room and features granite countertops, solid wood soft-close cabinetry, a gas cooktop, wall oven, breakfast bar, wet bar, walk-in pantry, and a sunny breakfast nook overlooking the lanai and pool. The adjoining family room is anchored by a gas fireplace and French doors leading outdoors. The covered lanai showcases a tongue-and-groove ceiling and remote-controlled screens, creating the perfect setting for year-round entertaining. The generous first-floor primary suite offers space for a sitting area and features two custom walk-in closets, dual vanities, a soaking tub, separate shower, and private water closet. A beautiful wrought-iron staircase leads upstairs to two generous en-suite bedrooms and a cozy loft. The private backyard is designed for relaxation and entertaining, featuring a saltwater pool and spa surrounded by lush landscaping. Additional highlights include two newer HVAC systems (2022 and 2023), a gas water heater (2022), central vacuum system, built-in Home Team pest defense system, and plantation shutters throughout. Located within the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home is ideally situated between Park Avenue and Corrine Drive, with downtown Orlando just minutes away.

341 E Reading Way, Winter Park

$1,025,000

Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

3 Beds ⋅ 3 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

1138 S Pennsylvania Avenue, Winter Park

$2,800,000

Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desirable locations. Situated in the heart of Hannibal Square and just three blocks from Park Avenue, this residence places premier dining, shopping, galleries, museums, Central Park and year-round community events within easy walking distance. Thoughtfully designed with both style and functionality in mind, the home showcases high-end finishes throughout including rich Brazilian walnut flooring, oversized 24 x 48 ceramic tile, coffered ceilings, quartz countertops, custom cabinetry and premium stainless-steel appliances. The chef’s kitchen is anchored by an eight-burner Wolf gas range and a Sub-Zero refrigerator, paired with a hidden pantry discreetly concealed behind custom cabinetry. A striking metal staircase serves as a central architectural feature, adding a contemporary design element that complements the home’s clean lines and sophisticated aesthetic. The open-concept floor plan is filled with natural light, enhanced by expansive windows throughout that frame peaceful green views and mature tree-lined surroundings. The main living areas extend seamlessly to the outdoors, where a first-floor entertaining wet bar with a wine refrigerator opens directly to the private courtyard, creating an effortless indoor-outdoor flow ideal for hosting. The courtyard features a fire pit surrounded by greenery, while the balcony off the main living area includes a summer kitchen. A fenced yard offers privacy and space for pets to enjoy. Designed for today’s lifestyle, the home includes a PRIVATE ELEVATOR servicing all three floors, dual HVAC systems, two tankless water heaters hardwired security cameras and a spacious three-car garage with an electric vehicle charging station and generous storage space. RARELY AVAILABLE in Downtown Winter Park, the oversized THREE CAR GARAGE offers exceptional functionality and flexibility. The private driveway provides additional parking while abundant guest parking nearby makes entertaining easy, an uncommon convenience in a downtown setting. The primary suite occupies the third floor, offering a private retreat with separation from the main living areas. It features a very large owner’s closet filled with natural light and a dedicated vanity area, creating a functional yet refined dressing space. Two additional bedrooms and a dedicated office or den provide flexibility for working from home, accommodating guests or creating additional living space. Each bathroom has been thoughtfully appointed with quality finishes and timeless design. Tucked within a quiet enclave , this residence offers a unique balance of privacy and walkability. The property is adjacent to the recently completed $6.1 million residence of internationally respected architect Kamal Rizk further underscoring the caliber of the surrounding neighborhood. Homes of this quality and location rarely come to market, presenting a truly limited opportunity to own in one of Winter Park’s most sought-after addresses. Combining the architectural vision and craftsmanship of Phil Kean Design Group with luxury finishes, modern conveniences and an exceptional location, this residence offers sophisticated low-maintenance living in the heart of Winter Park’s most vibrant neighborhood. Furniture may convey and pricing upon request. New 10 yr. termite bond will convey with the sale.

3 Beds ⋅ 4 Baths ⋅ Morse & Pennsylvania Twnhms SubDv. ⋅ 32789 Zip Code

Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desirable locations. Situated in the heart of Hannibal Square and just three blocks from Park Avenue, this residence places premier dining, shopping, galleries, museums, Central Park and year-round community events within easy walking distance. Thoughtfully designed with both style and functionality in mind, the home showcases high-end finishes throughout including rich Brazilian walnut flooring, oversized 24 x 48 ceramic tile, coffered ceilings, quartz countertops, custom cabinetry and premium stainless-steel appliances. The chef’s kitchen is anchored by an eight-burner Wolf gas range and a Sub-Zero refrigerator, paired with a hidden pantry discreetly concealed behind custom cabinetry. A striking metal staircase serves as a central architectural feature, adding a contemporary design element that complements the home’s clean lines and sophisticated aesthetic. The open-concept floor plan is filled with natural light, enhanced by expansive windows throughout that frame peaceful green views and mature tree-lined surroundings. The main living areas extend seamlessly to the outdoors, where a first-floor entertaining wet bar with a wine refrigerator opens directly to the private courtyard, creating an effortless indoor-outdoor flow ideal for hosting. The courtyard features a fire pit surrounded by greenery, while the balcony off the main living area includes a summer kitchen. A fenced yard offers privacy and space for pets to enjoy. Designed for today’s lifestyle, the home includes a PRIVATE ELEVATOR servicing all three floors, dual HVAC systems, two tankless water heaters hardwired security cameras and a spacious three-car garage with an electric vehicle charging station and generous storage space. RARELY AVAILABLE in Downtown Winter Park, the oversized THREE CAR GARAGE offers exceptional functionality and flexibility. The private driveway provides additional parking while abundant guest parking nearby makes entertaining easy, an uncommon convenience in a downtown setting. The primary suite occupies the third floor, offering a private retreat with separation from the main living areas. It features a very large owner’s closet filled with natural light and a dedicated vanity area, creating a functional yet refined dressing space. Two additional bedrooms and a dedicated office or den provide flexibility for working from home, accommodating guests or creating additional living space. Each bathroom has been thoughtfully appointed with quality finishes and timeless design. Tucked within a quiet enclave , this residence offers a unique balance of privacy and walkability. The property is adjacent to the recently completed $6.1 million residence of internationally respected architect Kamal Rizk further underscoring the caliber of the surrounding neighborhood. Homes of this quality and location rarely come to market, presenting a truly limited opportunity to own in one of Winter Park’s most sought-after addresses. Combining the architectural vision and craftsmanship of Phil Kean Design Group with luxury finishes, modern conveniences and an exceptional location, this residence offers sophisticated low-maintenance living in the heart of Winter Park’s most vibrant neighborhood. Furniture may convey and pricing upon request. New 10 yr. termite bond will convey with the sale.

660 W Morse Boulevard, Winter Park

$350,000

Welcome to this beautifully maintained townhome located in the heart of Winter Park, Florida. From the moment you arrive, the charming exterior draws you in with its classic stucco finish, attached one-car garage, manicured landscaping, and a welcoming shaded entry framing the front door. Step inside to an inviting foyer featuring high ceilings, modern lighting, and a striking staircase that sets a stylish tone for the rest of the home. The main level transitions into an expansive, light-filled open concept floor plan seamlessly connecting the living room, dining area, and kitchen. Rich wood-look LVP flooring runs throughout the entire lower level, perfectly complementing the crisp neutral walls and providing a cohesive, contemporary aesthetic. The spacious living and dining areas offer an exceptional layout for both daily living and effortless entertaining. Large sliding glass doors at the rear of the home flood the living space with natural light and open directly to a private, screened-in back patio, making it easy to enjoy the Florida breeze. Overlooking the dining area is a spacious kitchen, which features a half-wall cutout that keeps the chef connected to the conversation. Equipped with plenty of warm wood cabinetry, neutral countertops, a deep double sink, and a suite of white appliances, this kitchen is as ample as it is welcoming. A convenient guest half-bathroom with a pedestal sink completes the well-designed ground floor layout. Head upstairs to discover the private living quarters, where the beautiful wood-look flooring continues through the hallway and into each spacious bedroom. The expansive primary suite serves as a true retreat, boasting high vaulted ceilings, an elegant modern ceiling fan, a massive walk-in closet with built-in wire shelving, and a trio of large windows that fill the space with cheerful morning light. This main bedroom easily accommodates king-sized furniture and offers the luxury of an attached en-suite bathroom with dual sinks. The additional bedrooms are equally impressive, each featuring soaring vaulted ceilings, updated stylish ceiling fans, and generous closet space near the dedicated upper-level laundry closet, which comes equipped with a washer and dryer. The outdoor and utility spaces add tremendous value and convenience to this efficient property. The attached garage features an open, clean layout perfect for secure parking, extra storage, or a small home workshop area. At the back of the home, the deep screened-in patio is an ideal spot for outdoor dining, grilling, or relaxing in the shade. The patio steps out onto a beautiful community green belt with pristine lawns and mature shade trees, offering a peaceful residential backdrop. Nestled in a premium, tree-lined enclave, the community boasts pristine, winding roads, manicured privacy hedges, and a scenic retention pond complete with a flowing water fountain feature. This idyllic neighborhood setting perfectly balances the tranquility of nature with outstanding proximity to nearby lakes, parks, major roadways, and local shopping centers. Don't miss the opportunity to own this pristine, move-in ready retreat in one of Central Florida's most highly sought-after locations.

3 Beds ⋅ 3 Baths ⋅ Vistas At Lake Howell SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully maintained townhome located in the heart of Winter Park, Florida. From the moment you arrive, the charming exterior draws you in with its classic stucco finish, attached one-car garage, manicured landscaping, and a welcoming shaded entry framing the front door. Step inside to an inviting foyer featuring high ceilings, modern lighting, and a striking staircase that sets a stylish tone for the rest of the home. The main level transitions into an expansive, light-filled open concept floor plan seamlessly connecting the living room, dining area, and kitchen. Rich wood-look LVP flooring runs throughout the entire lower level, perfectly complementing the crisp neutral walls and providing a cohesive, contemporary aesthetic. The spacious living and dining areas offer an exceptional layout for both daily living and effortless entertaining. Large sliding glass doors at the rear of the home flood the living space with natural light and open directly to a private, screened-in back patio, making it easy to enjoy the Florida breeze. Overlooking the dining area is a spacious kitchen, which features a half-wall cutout that keeps the chef connected to the conversation. Equipped with plenty of warm wood cabinetry, neutral countertops, a deep double sink, and a suite of white appliances, this kitchen is as ample as it is welcoming. A convenient guest half-bathroom with a pedestal sink completes the well-designed ground floor layout. Head upstairs to discover the private living quarters, where the beautiful wood-look flooring continues through the hallway and into each spacious bedroom. The expansive primary suite serves as a true retreat, boasting high vaulted ceilings, an elegant modern ceiling fan, a massive walk-in closet with built-in wire shelving, and a trio of large windows that fill the space with cheerful morning light. This main bedroom easily accommodates king-sized furniture and offers the luxury of an attached en-suite bathroom with dual sinks. The additional bedrooms are equally impressive, each featuring soaring vaulted ceilings, updated stylish ceiling fans, and generous closet space near the dedicated upper-level laundry closet, which comes equipped with a washer and dryer. The outdoor and utility spaces add tremendous value and convenience to this efficient property. The attached garage features an open, clean layout perfect for secure parking, extra storage, or a small home workshop area. At the back of the home, the deep screened-in patio is an ideal spot for outdoor dining, grilling, or relaxing in the shade. The patio steps out onto a beautiful community green belt with pristine lawns and mature shade trees, offering a peaceful residential backdrop. Nestled in a premium, tree-lined enclave, the community boasts pristine, winding roads, manicured privacy hedges, and a scenic retention pond complete with a flowing water fountain feature. This idyllic neighborhood setting perfectly balances the tranquility of nature with outstanding proximity to nearby lakes, parks, major roadways, and local shopping centers. Don't miss the opportunity to own this pristine, move-in ready retreat in one of Central Florida's most highly sought-after locations.

2521 Galliano Circle, Winter Park

$1,725,000

Welcome to an exceptional lakefront home in the gated community of Lake Florence Preserve, where luxury, space, and lifestyle come together in the heart of Winter Park. This stunning 6-bedroom, 5+ bath pool home sits on the shores of private, Lake Florence, offering a rare opportunity for true waterfront living. Step inside to a grand two-story entry with soaring 10-foot ceilings and an open-concept layout designed for effortless entertaining. Natural light fills the expansive living, dining, and kitchen spaces, highlighting the home’s high-end finishes and thoughtful design. At the center of the home is a chef’s kitchen featuring an oversized 11’ x 5’ island, gas range with vent hood, premium Samsung and GE appliances, and an impressive 10’ x 4’ walk-in pantry, perfect for hosting or daily convenience. With six generously sized bedrooms, including a private in-law suite, this home offers flexibility for multigenerational living or guests. Upstairs, the spacious primary suite boasts lake views, a large ensuite bath, and dual walk-in closets. You’ll also find a versatile 19’ x 18’ game room with a 17' wide balcony overlooking the pool and lake, along with an oversized second-floor laundry room. Outdoor living is where this property truly shines. Enjoy direct access to Lake Florence from your private dock with electric boat lift, ideal for boating, jet skiing, or peaceful sunset cruises. The backyard is designed for relaxation and entertaining, complete with a saltwater pool, fully fenced yard, tiki hut featuring an outdoor kitchen and outdoor shower fitted with hot and cold water. Additional highlights include a 3-car garage, tankless water heater, custom closets throughout, and upgraded lighting and ceiling fans. Ideally located just minutes from SR 436, the 417, and only 15 minutes to Park Avenue, this home offers both convenience and exclusivity within a sought-after gated community. This is a rare opportunity to own a true lakefront retreat. Schedule your private showing today.

6 Beds ⋅ 6 Baths ⋅ Lake Florence Preserve SubDv. ⋅ 32792 Zip Code

Welcome to an exceptional lakefront home in the gated community of Lake Florence Preserve, where luxury, space, and lifestyle come together in the heart of Winter Park. This stunning 6-bedroom, 5+ bath pool home sits on the shores of private, Lake Florence, offering a rare opportunity for true waterfront living. Step inside to a grand two-story entry with soaring 10-foot ceilings and an open-concept layout designed for effortless entertaining. Natural light fills the expansive living, dining, and kitchen spaces, highlighting the home’s high-end finishes and thoughtful design. At the center of the home is a chef’s kitchen featuring an oversized 11’ x 5’ island, gas range with vent hood, premium Samsung and GE appliances, and an impressive 10’ x 4’ walk-in pantry, perfect for hosting or daily convenience. With six generously sized bedrooms, including a private in-law suite, this home offers flexibility for multigenerational living or guests. Upstairs, the spacious primary suite boasts lake views, a large ensuite bath, and dual walk-in closets. You’ll also find a versatile 19’ x 18’ game room with a 17' wide balcony overlooking the pool and lake, along with an oversized second-floor laundry room. Outdoor living is where this property truly shines. Enjoy direct access to Lake Florence from your private dock with electric boat lift, ideal for boating, jet skiing, or peaceful sunset cruises. The backyard is designed for relaxation and entertaining, complete with a saltwater pool, fully fenced yard, tiki hut featuring an outdoor kitchen and outdoor shower fitted with hot and cold water. Additional highlights include a 3-car garage, tankless water heater, custom closets throughout, and upgraded lighting and ceiling fans. Ideally located just minutes from SR 436, the 417, and only 15 minutes to Park Avenue, this home offers both convenience and exclusivity within a sought-after gated community. This is a rare opportunity to own a true lakefront retreat. Schedule your private showing today.

2914 Reef Knot Place, Winter Park

$185,000

Discover the potential of this 2-bedroom, 2-bath end-unit condominium located in the desirable Wrenwood Condominium community in Winter Park, Florida. Offering 1,058 square feet of living space, this home presents an excellent opportunity for buyers seeking affordability, convenience, and the chance to add their own personal style. Inside, you'll find ceramic tile flooring throughout, knockdown ceilings, and a functional floor plan designed for comfortable everyday living. All kitchen appliances are included, making your transition even easier. The end-unit location provides additional privacy and natural light while offering pleasant views of the community pool. Built with solid concrete block construction, this condominium offers durability and low-maintenance ownership. The bathrooms could benefit from updating, providing the perfect opportunity for the next owner to customize the home to their own taste and preferences. Whether you're a first-time homebuyer, downsizing, looking for a seasonal residence, or seeking an investment property, this home offers tremendous potential and value. Wrenwood Condominium allows up to two pets, with a maximum weight of 25 pounds each, making it a great option for pet lovers. Conveniently located near shopping, dining, entertainment, major highways, and everything Winter Park and the greater Orlando area have to offer. Don't miss this opportunity to own an affordable Winter Park condominium and create the home you've always envisioned.

2 Beds ⋅ 2 Baths ⋅ Wrenwood Condo SubDv. ⋅ 32792 Zip Code

Discover the potential of this 2-bedroom, 2-bath end-unit condominium located in the desirable Wrenwood Condominium community in Winter Park, Florida. Offering 1,058 square feet of living space, this home presents an excellent opportunity for buyers seeking affordability, convenience, and the chance to add their own personal style. Inside, you'll find ceramic tile flooring throughout, knockdown ceilings, and a functional floor plan designed for comfortable everyday living. All kitchen appliances are included, making your transition even easier. The end-unit location provides additional privacy and natural light while offering pleasant views of the community pool. Built with solid concrete block construction, this condominium offers durability and low-maintenance ownership. The bathrooms could benefit from updating, providing the perfect opportunity for the next owner to customize the home to their own taste and preferences. Whether you're a first-time homebuyer, downsizing, looking for a seasonal residence, or seeking an investment property, this home offers tremendous potential and value. Wrenwood Condominium allows up to two pets, with a maximum weight of 25 pounds each, making it a great option for pet lovers. Conveniently located near shopping, dining, entertainment, major highways, and everything Winter Park and the greater Orlando area have to offer. Don't miss this opportunity to own an affordable Winter Park condominium and create the home you've always envisioned.

4756 Tangerine Avenue Unit 4756, Winter Park

$490,000

Virtually Staged. Discover space, comfort, and flexibility in this beautifully updated 4-bedroom, 2-bath home in the highly desirable Cedar Ridge community of Winter Park with no HOA. Offering approximately 2,250 square feet of living space, this home also features a versatile flex room ideal as a nursery, home office, guest suite, media room, or private retreat. The 2025 remodeled kitchen offers abundant cabinetry and pantry storage, while the renovated bathrooms feature stylish, modern finishes. Ceramic tile flows throughout most of the home, with warm wood-look flooring in three bedrooms for added comfort. Enjoy peace of mind with major improvements already completed, including a 2024 roof, 2023 whole-home replumbing, and 2023 electrical panel replacement with generator hookup. These significant updates allow you to focus on enjoying your new home instead of tackling major projects. Step outside to an oversized, fully fenced backyard shaded by two magnificent mature oak trees, creating a private setting for relaxing, entertaining, or family gatherings. A side-entry two-car garage adds both curb appeal and everyday convenience. Conveniently located just minutes from Baldwin Park, UCF, shopping, dining, parks, and Seminole County schools, this Cedar Ridge home offers exceptional space, recent major updates, and the convenience of an established Winter Park neighborhood with no HOA.

4 Beds ⋅ 2 Baths ⋅ Cedar Ridge SubDv. ⋅ 32792 Zip Code

Virtually Staged. Discover space, comfort, and flexibility in this beautifully updated 4-bedroom, 2-bath home in the highly desirable Cedar Ridge community of Winter Park with no HOA. Offering approximately 2,250 square feet of living space, this home also features a versatile flex room ideal as a nursery, home office, guest suite, media room, or private retreat. The 2025 remodeled kitchen offers abundant cabinetry and pantry storage, while the renovated bathrooms feature stylish, modern finishes. Ceramic tile flows throughout most of the home, with warm wood-look flooring in three bedrooms for added comfort. Enjoy peace of mind with major improvements already completed, including a 2024 roof, 2023 whole-home replumbing, and 2023 electrical panel replacement with generator hookup. These significant updates allow you to focus on enjoying your new home instead of tackling major projects. Step outside to an oversized, fully fenced backyard shaded by two magnificent mature oak trees, creating a private setting for relaxing, entertaining, or family gatherings. A side-entry two-car garage adds both curb appeal and everyday convenience. Conveniently located just minutes from Baldwin Park, UCF, shopping, dining, parks, and Seminole County schools, this Cedar Ridge home offers exceptional space, recent major updates, and the convenience of an established Winter Park neighborhood with no HOA.

2008 Houndslake Drive, Winter Park

$725,000

Welcome to this stunning Taylor Morrison Boca model in the highly desirable Hawks Crest gated community. This beautifully maintained 4-bedroom, 2.5-bath home offers an exceptional blend of luxury, comfort, and modern convenience. Upon entry, you're greeted by a dramatic two-story foyer with soaring 20-foot ceilings and abundant natural light. The open-concept living spaces feature luxury vinyl plank flooring throughout, plantation shutters, and corner sliding glass doors that seamlessly connect indoor and outdoor living. Enjoy breathtaking west-facing water views, a picturesque fountain and bridge backdrop, and spectacular sunset views from your private backyard. One of the home's standout features is its generously sized, aluminum-fenced backyard, offering ample space for outdoor entertaining, play, pets, gardening, or even a future pool while still enjoying tranquil waterfront views. Thoughtful smart-home upgrades include electric curtains on the sliding doors, Eufy security cameras, smart door locks, and a MyQ-enabled garage door. The oversized two-car garage also features convenient touchpad access. Residents of Hawks Crest enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, and scenic walking trails. Outdoor enthusiasts will appreciate direct access to Lake Howell for kayaking and canoeing. HOA dues include professional landscaping maintenance, allowing homeowners to enjoy a beautifully maintained property with less upkeep. This move-in-ready home offers the perfect combination of elegant design, premium upgrades, abundant outdoor space, low-maintenance living, and an unbeatable waterfront lifestyle.

4 Beds ⋅ 3 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to this stunning Taylor Morrison Boca model in the highly desirable Hawks Crest gated community. This beautifully maintained 4-bedroom, 2.5-bath home offers an exceptional blend of luxury, comfort, and modern convenience. Upon entry, you're greeted by a dramatic two-story foyer with soaring 20-foot ceilings and abundant natural light. The open-concept living spaces feature luxury vinyl plank flooring throughout, plantation shutters, and corner sliding glass doors that seamlessly connect indoor and outdoor living. Enjoy breathtaking west-facing water views, a picturesque fountain and bridge backdrop, and spectacular sunset views from your private backyard. One of the home's standout features is its generously sized, aluminum-fenced backyard, offering ample space for outdoor entertaining, play, pets, gardening, or even a future pool while still enjoying tranquil waterfront views. Thoughtful smart-home upgrades include electric curtains on the sliding doors, Eufy security cameras, smart door locks, and a MyQ-enabled garage door. The oversized two-car garage also features convenient touchpad access. Residents of Hawks Crest enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, and scenic walking trails. Outdoor enthusiasts will appreciate direct access to Lake Howell for kayaking and canoeing. HOA dues include professional landscaping maintenance, allowing homeowners to enjoy a beautifully maintained property with less upkeep. This move-in-ready home offers the perfect combination of elegant design, premium upgrades, abundant outdoor space, low-maintenance living, and an unbeatable waterfront lifestyle.

1316 Blue Stem Lane, Winter Park

$440,000

Welcome to 8433 Commander Cove, ideally situated on a quiet cul-de-sac in the highly sought-after Trinity Bay community. Upon entering this spacious home you're greeted by soaring vaulted ceilings, a formal dining area, and a stunning cathedral-style front window that fills the space with natural light. The separate enclosed kitchen offers functionality and charm, with French doors leading to a covered, tiled lanai. Step outside and enjoy a large patio surrounded by mature trees and lush landscaping—an ideal setting for morning coffee, outdoor entertaining, and family barbecues. The inviting family room showcases vaulted ceilings, a grand brick fireplace, and a versatile bonus den/office with a window, perfect for working from home or additional living space. Conveniently located off the family room is an indoor laundry area and half bath. The first-floor primary suite offers privacy and comfort, featuring a dual-vanity bathroom and private French door access to the covered lanai. Upstairs, you'll find three generously sized bedrooms, each equipped with ceiling fans and ample closet space, along with a second dual-vanity full bathroom. Whether you're a first-time homebuyer or looking for room to accommodate a growing family, this home offers exceptional value and functionality. Residents of Trinity Bay enjoy access to a community pool, community playground, and a private neighborhood boat ramp with access to the Lake Burkett and Lake Martha Chain of Lakes, where boating, water skiing, fishing, and other recreational activities are welcomed. Don't miss this opportunity to own a beautiful home in one of the area's most desirable neighborhoods!

4 Beds ⋅ 3 Baths ⋅ Trinity Bay SubDv. ⋅ 32792 Zip Code

Welcome to 8433 Commander Cove, ideally situated on a quiet cul-de-sac in the highly sought-after Trinity Bay community. Upon entering this spacious home you're greeted by soaring vaulted ceilings, a formal dining area, and a stunning cathedral-style front window that fills the space with natural light. The separate enclosed kitchen offers functionality and charm, with French doors leading to a covered, tiled lanai. Step outside and enjoy a large patio surrounded by mature trees and lush landscaping—an ideal setting for morning coffee, outdoor entertaining, and family barbecues. The inviting family room showcases vaulted ceilings, a grand brick fireplace, and a versatile bonus den/office with a window, perfect for working from home or additional living space. Conveniently located off the family room is an indoor laundry area and half bath. The first-floor primary suite offers privacy and comfort, featuring a dual-vanity bathroom and private French door access to the covered lanai. Upstairs, you'll find three generously sized bedrooms, each equipped with ceiling fans and ample closet space, along with a second dual-vanity full bathroom. Whether you're a first-time homebuyer or looking for room to accommodate a growing family, this home offers exceptional value and functionality. Residents of Trinity Bay enjoy access to a community pool, community playground, and a private neighborhood boat ramp with access to the Lake Burkett and Lake Martha Chain of Lakes, where boating, water skiing, fishing, and other recreational activities are welcomed. Don't miss this opportunity to own a beautiful home in one of the area's most desirable neighborhoods!

8433 Commander Cove, Winter Park

$3,795,000

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

1600 Legion Drive, Winter Park

$1,595,000

Exceptional opportunity in the heart of Winter Park - a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue's renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted "Vias" of Winter Park, a collection of streets long regarded as one of the city's most established and desirable residential enclaves. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end users alike - a rare chance to secure one of winter Park's most desirable land offerings in a highly established neighborhood.

Tuscany Terrace SubDv. ⋅ 32789 Zip Code

Exceptional opportunity in the heart of Winter Park - a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue's renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted "Vias" of Winter Park, a collection of streets long regarded as one of the city's most established and desirable residential enclaves. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end users alike - a rare chance to secure one of winter Park's most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park

$849,900

Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood cabinetry, a wet bar for effortless entertaining, a dining room, and a convenient half bath - all finished with rich hardwood floors. French doors lead to a private, fenced yard with two deck spaces, one covered with an awning, perfect for outdoor entertaining or quiet mornings outside. Also on the main level, the spacious primary suite offers an oversized walk-in closet and direct yard access. The luxurious primary bath features double vanities, a soaking tub, and a separate standing shower. Upstairs, a generous bonus living space is flanked by two additional bedrooms, one of which includes an en-suite bath and two walk-in closets - ideal for guests or a home office setup. A full hall bath completes the upper level. Throughout the home, storage has been thoughtfully considered, with generous closet space at every turn. Smart home features including remote-controlled outdoor lighting, garage door, irrigation, and alarm system make this the ultimate lock-and-leave lifestyle home. Residents also enjoy exclusive access to Virginia Heights Park, a private lakefront park reserved for neighborhood use only - a rare amenity in the heart of Winter Park. Come see what makes this property so special!

3 Beds ⋅ 4 Baths ⋅ Virginia Hgts Rep SubDv. ⋅ 32789 Zip Code

Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood cabinetry, a wet bar for effortless entertaining, a dining room, and a convenient half bath - all finished with rich hardwood floors. French doors lead to a private, fenced yard with two deck spaces, one covered with an awning, perfect for outdoor entertaining or quiet mornings outside. Also on the main level, the spacious primary suite offers an oversized walk-in closet and direct yard access. The luxurious primary bath features double vanities, a soaking tub, and a separate standing shower. Upstairs, a generous bonus living space is flanked by two additional bedrooms, one of which includes an en-suite bath and two walk-in closets - ideal for guests or a home office setup. A full hall bath completes the upper level. Throughout the home, storage has been thoughtfully considered, with generous closet space at every turn. Smart home features including remote-controlled outdoor lighting, garage door, irrigation, and alarm system make this the ultimate lock-and-leave lifestyle home. Residents also enjoy exclusive access to Virginia Heights Park, a private lakefront park reserved for neighborhood use only - a rare amenity in the heart of Winter Park. Come see what makes this property so special!

1265 Arlington Pl, Winter Park

$2,250,000

A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.

5 Beds ⋅ 5 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code

A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.

240 N Phelps Avenue, Winter Park

$4,950,000

Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home's advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.

4 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home's advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.

231 Chelton Circle, Winter Park

The Nest Group

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