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$1,450,000
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

$2,299,000
5 Beds 5 Baths Charmont SubDv. 32789 Zip Code
Under Construction. Experience modern luxury in this exceptional new construction residence by LUIH Luxury Homes, scheduled for completion in December 2026.Offering 5 bedrooms, 5 bathrooms, and 2,868 square feet of thoughtfully designed living space, this home showcases contemporary architecture, refined finishes, and a functional layout tailored to today's lifestyle. A light-filled open floor plan creates effortless flow between the living, dining, and kitchen spaces, making the home equally suited for everyday living and entertaining. Designer details and carefully selected finishes bring warmth and sophistication throughout, while expansive windows enhance the bright, inviting interiors. The private outdoor living area is designed to embrace Florida living, featuring a resort-style pool and spa with plenty of space to relax, dine, and entertain. Ideally situated near Park Avenue, residents will enjoy convenient access to boutique shopping, acclaimed restaurants, golf courses, parks, and Winter Park's renowned arts and cultural destinations, all while enjoying the comfort and quality of a brand-new luxury home.

1840 Laurel Road, Winter Park

$1,749,000
4 Beds 4 Baths Winter Park Village SubDv. 32789 Zip Code
Under Construction. Currently under construction by LUIH Luxury Homes, this exceptional new construction residence is anticipated for completion in November 2026 and brings contemporary design and elevated living to one of Winter Park's most desirable neighborhoods. Offering 4 bedrooms, 3.5 bathrooms, and 2,715 square feet of thoughtfully designed living space, the home blends clean architectural lines with warm, inviting interiors designed for both everyday living and effortless entertaining. The open-concept floor plan is filled with natural light and seamlessly connects the main living areas, creating a spacious and functional layout. Designer finishes, sophisticated details, and carefully selected materials elevate every space, while the chef-inspired kitchen serves as the heart of the home. Step outside to your private backyard retreat featuring a resort-style pool and spa, providing the perfect setting for relaxing or entertaining year-round. Ideally located just minutes from Park Avenue, residents will enjoy easy access to award-winning dining, boutique shopping, parks, golf courses, and Winter Park's vibrant cultural scene.

2525 Lafayette Avenue, Winter Park

$4,750,000
5 Beds 5 Baths Lake Maitland SubDv. 32789 Zip Code
Privately nestled on 1.32 acres (1.1+ acres HIGH & DRY) along the tranquil shores of Lake Temple, this remarkable residence is a true compound where architecture, craftsmanship, and nature exist in perfect balance. Completed in 2019 by Gallimore Homes and enhanced with more than $300K in upgrades, this home was designed to feel secluded and private while serving as the ultimate destination for entertaining. This unique property offers a 4,060+ SF main residence (4 beds / 3.5 baths plus bonus room for a future 5th bedroom), a detached 480+ SF guest house (1 bed / 1 bath), and resort-style outdoor living overlooking peaceful water views and a rolling backyard. Designed for exceptional privacy, the home is positioned well back from the street and buffered by mature landscaping, a private courtyard wall with a security gate, and hurricane-impact windows and doors throughout. Additional highlights include an oversized three-car garage, parking for 15+ vehicles, and space to park a boat or RV next to the conservation area. Inside, soaring ceilings and premium finishes create an immediate sense of warmth and sophistication. Ten-foot-tall EuroWall folding glass doors span 15 feet across the great room, seamlessly blending indoor and outdoor living while framing beautiful backyard and water views. The chef's kitchen showcases professional-grade Sub-Zero and Wolf appliances, an oversized gathering island with prep sink, ice maker, waterfall countertops, a 48-inch Wolf six-burner dual-fuel range, dry bar with refrigerated drawers, and a spacious walk-in pantry. The open-concept design flows effortlessly into the great room and dining area, making everyday living and entertaining equally inviting. The split-bedroom floor plan offers exceptional privacy, highlighted by a spacious first-floor primary suite with 2 walk-in closets (totaling 175+ SF) and a spa-inspired bath. The first floor also includes a guest suite, two additional bedrooms with a Jack-and-Jill bath, and a powder/pool bath with access to the lania. Upstairs, the bonus room provides flexibility for a media room, game room, home office, and pre-plumed for a bath and kitchenette for a future 5th bedroom. Equally impressive is the detached guest house, complete with its own covered front porch, full kitchen, living room, bedroom, full bath, and beautiful backyard views…ideal for multigenerational living, extended guests, a private office, or long-term visitors. The covered lanai was designed for year-round outdoor living with three Phantom Screens spanning nearly 45 feet, an authentic Argentine wood-fired grill, and a built-in wet bar. The heated saltwater infinity-edge pool features a sun shelf, LED lighting, and a composite wood sun deck overlooking the water. The expansive lawn gently slopes to the shoreline beneath a magnificent 100+ year-old oak tree, enhanced by mature landscaping and landscape lighting that creates an unforgettable setting for intimate evenings and large-scale gatherings too. Located less than three miles from Interlachen Country Club and a few blocks from the Winter Park Racquet Club, this property offers a rare combination of privacy, flexibility, and estate-style living on more than an acre of waterfront in Winter Park. (*Ask for a Floorplan, List of Improvements, and Survey. Click the Virtual Tour link to see a video of the property! )

2525 Temple Drive, Winter Park

$675,000
3 Beds 2 Baths Winter Park Pines SubDv. 32792 Zip Code
Welcome to this beautifully updated three-bedroom, two-bathroom pool home offering nearly 1,800 square feet of thoughtfully designed living space on a spacious lot backing to a peaceful conservation easement. Featuring separate living and family rooms, a remodeled kitchen, and an exceptional outdoor retreat, this inviting home is perfectly designed for both everyday living and entertaining. From the moment you arrive, the classic brick entry creates a warm first impression. Inside, the flexible floor plan provides plenty of space to gather, relax, work from home, or host guests. Laminate wood flooring and updated baseboards (2022) complement plantation shutters, recessed lighting, and ceiling fans throughout. Multiple storage closets add everyday functionality, while updated windows and French doors fill the home with natural light and seamlessly connect the indoor and outdoor living spaces. The remodeled kitchen (2021) features crisp white shaker cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, an oversized stainless-steel sink, and a breakfast bar with seating for four. A dedicated coffee bar and pantry add convenience, while the large bay window overlooks the pool and private backyard, creating the perfect backdrop for everyday living. The spacious primary suite offers a walk-in closet and ceiling fan. Its ensuite bathroom, renovated in 2022, features large marble-look tile, a double vanity with quartz countertops, and a beautifully updated walk-in shower with a frameless glass enclosure. Two additional guest bedrooms and an updated full bathroom complete the bedroom wing. Step outside to the true centerpiece of the home. Backing to a conservation easement, the backyard offers a peaceful setting with enhanced privacy. The screened, in-ground chlorine pool was completely refreshed in 2025 with new tile, repaired beam, resurfacing, and new pool light. The lanai deck was also resurfaced, creating an ideal space for swimming, outdoor dining, and entertaining family and friends. The outdoor improvements continue with fresh landscaping completed in 2025, including new sod, a stone pathway, French drains for improved drainage, and an updated irrigation timer. The fully fenced backyard (2023) provides additional privacy for pets, play, and gatherings. Ideally located near Cady Way Trail and Winter Park Pines Golf Course, you'll also enjoy convenient access to Cady Way Park amenities, including a community pool, playground, tennis and pickleball courts, beach volleyball, and walking trails. AdventHealth Winter Park and the Crosby Wellness Center are just minutes away, while Rollins College, Full Sail University, UCF, and Orlando International Airport are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines modern updates, flexible living spaces, and a private backyard retreat in one of Winter Park's most desirable locations. ROOF - 2024 ELECTRICAL PANELS - 2021

433 Gilbert Road, Winter Park

$435,000
3 Beds 2 Baths Garden Lake Estates Unit 1 SubDv. 32792 Zip Code
This is an Excellent split plan pool home. Tile floors in the Family room, Living Room, and Dining room keep with the Florida syle. The bedrooms feature wood floors in all the bedrooms.The screened in pool is also heated and has a Heated Spa. It is conveniently located in Seminole County with a Winter Park address. It also features a ROOF that is only two years old ! You can cool off in the screened in pool on hot days. During the cooler time of year you can use the Heater for both the pool and Spa.The screen enclosure helps to make the pool more inviting. You also have a covered porch area for entertaining. There is yard space that is fully fenced. The back yard also has a shed for storing your yard tools. SOLD AS IS. Contact the Listing Agent for a personal tour !

3740 Hawthorne Lane, Winter Park

$278,000
2 Beds 2 Baths Cedarwood Village 1 SubDv. 32792 Zip Code
Turnkey Living in the Heart of Winter Park! Welcome to this beautifully maintained 2-bedroom, 2-bath townhome offering the perfect blend of comfort, convenience, and low-maintenance living. Vacant and move-in ready, this home has been freshly painted and features a recently replaced air conditioning system, providing peace of mind for its next owner. Inside, you'll find a thoughtfully designed floor plan with spacious living and dining areas, a well-appointed kitchen, and two generously sized bedrooms and bathrooms designed for comfort and functionality. Whether you're relaxing at home or entertaining friends and family, this inviting layout makes everyday living effortless. Step outside and enjoy the exceptional community amenities, including a sparkling swimming pool and tennis courts, perfect for enjoying Florida's year-round sunshine. Whether you're a first-time homebuyer, downsizing, seeking a second home, or looking for an investment opportunity, this property offers incredible versatility. Ideally located in desirable Winter Park, you'll be just minutes from shopping, dining, entertainment, major highways, UCF, Full Sail University, Downtown Winter Park, and Downtown Orlando, making commuting and enjoying Central Florida's best attractions a breeze. Don't miss your opportunity to own this beautifully updated, turnkey home in one of Central Florida's most sought-after communities! All room measurements, HOA information, square footage, and property details are deemed reliable but not guaranteed and should be independently verified by the buyer and buyer's agent.

2475 Tahoe Circle Unit 2475, Winter Park

$129,000
1 Beds 1 Baths Golfside Villas Condo SubDv. 32792 Zip Code
Freshly Updated 1-Bedroom Condo – Perfect for Homeowners or Investors! Whether you're looking for your first home, downsizing, or adding to your investment portfolio, this move-in-ready 1-bedroom, 1-bath condominium is an excellent opportunity. Featuring brand-new luxury vinyl plank flooring and a freshly painted interior, this home offers a clean, modern feel throughout. The open-concept floor plan seamlessly connects the kitchen, dining, and living areas, creating a bright and inviting space for everyday living and entertaining. A set of French doors leads to the screened-in porch, providing the perfect spot to enjoy your morning coffee or unwind after a long day. The spacious bedroom features a large walk-in closet, offering plenty of storage. This condo also includes one assigned parking space, along with additional guest parking for visitors. Residents enjoy access to a community pool and onsite laundry facilities, adding to the convenience of low-maintenance living. Ideally located just minutes from SR 408, the University of Central Florida (UCF), shopping, dining, restaurants, and entertainment, this condo offers an unbeatable combination of comfort, convenience, and value. Whether you're searching for a primary residence or a smart investment opportunity in a high-demand area, this Central Florida gem is one you won't want to miss!

1000 S Semoran Boulevard Unit 305, Winter Park

$1,419,900
4 Beds 4 Baths Lawndale SubDv. 32789 Zip Code
Under Construction. Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by one of the areas finest builders. This stunning new farmhouse-inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant 2 story entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows seamlessly into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool and lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with dual vanities, a freestanding soaking tub, and a spacious walk-in closet with custom shelving. A convenient laundry area is thoughtfully located just off the suite. Upstairs, a large bonus room with a closet offers versatility as a fifth bedroom, game room, or home office. Two additional bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. The photos shown are of the same model in another location. Finishes will vary. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!

1546 Miller Avenue, Winter Park

$2,275,000
4 Beds 5 Baths J Kronenberger Sub SubDv. 32789 Zip Code
This WINTER PARK POOL HOME is set on a corner lot with entrances from both Palmer Avenue and Temple Drive. Located within Winter Park's exclusive J Kronenberger community, this luxury property is tucked away approximately a half mile to Winter Park's YMCA, Phelps Park & the lovely Kraft Azalea Garden, and approximately 1.5 miles to Park Avenue's restaurants, boutiques and farmer's market. The floor plan offers 4 bedrooms, 4.5 bathrooms & a home office/bonus room. The bedrooms are organized in a triple split plan arrangement that frames the open-concept gathering areas. Three bedrooms have private ensuite bathrooms, the 4th bedroom is placed directly next to the hall bath, and the office/bonus room sits adjacent to the guest half bath...everyone has a bathroom! Multiple exits lead out to the backyard, seamlessly merging the indoor and outdoor spaces. Mature hedges provide natural privacy for the open-air pool, spacious pool deck and backyard lawn. Additionally, a backyard paver path provides access to the property's 2-car detached garage. There is plenty of parking for year-round entertaining with the front half circle drive and the rear 2-car garage with multi-car driveway. This home uses natural gas to fuel the range, tankless water heater and outdoor firepit on the pool deck. Recent updates include outdoor perimeter lighting, rear fence, privacy hedges & irrigation. Prime real estate within Winter Park’s historic tree-lined streets.

1271 Palmer Avenue, Winter Park

$259,000
3 Beds 3 Baths Cedarwood Village 1 SubDv. 32792 Zip Code
Welcome to 2433 Grand Teton Circle in the sought-after Cedarwood Village community of Winter Park, where move-in ready living, thoughtful updates, and an unbeatable location come together. Featuring the largest floor plan in the community, this spacious condo has been refreshed with brand-new carpet and fresh interior paint, offering a bright, inviting space that’s ready for its next owner. The highly desirable layout includes a first-floor primary suite, making everyday living both comfortable and convenient. Inside, you’ll love the soaring vaulted ceilings that create an open, airy feel, while the wood-burning fireplace serves as the focal point of the living room, adding warmth and character. Just off the primary suite, a private front patio provides the perfect place to enjoy your morning coffee or unwind in the evening. A dedicated storage room offers additional space for seasonal décor, bicycles, and outdoor equipment. Cedarwood Village is known for its low-maintenance lifestyle, with the HOA maintaining the grounds and completing roof and exterior paint replacements approximately five years ago. Residents also enjoy access to a community pool, clubhouse, tennis courts, pickleball courts and guest parking. Location is one of this home’s greatest features. Ideally situated near Downtown Winter Park, Park Avenue, Winter Park Village, Baldwin Park, Full Sail University, Rollins College, Valencia College, and the University of Central Florida (UCF), you’ll enjoy convenient access to some of Central Florida’s best shopping, dining, entertainment, and recreation. Commuting is easy with nearby Howell Branch Road, Semoran Boulevard (SR 436), Aloma Avenue (SR 426), 417, and I4, providing quick access to Downtown Orlando, Maitland, Lake Mary, AdventHealth Winter Park, and Orlando International Airport. Located within the Seminole County Public School district, this home offers both convenience and an exceptional Winter Park address. Whether you’re searching for a primary residence, a low-maintenance home, or a spacious Winter Park condo in one of Central Florida’s most convenient locations, 2433 Grand Teton Circle offers the perfect combination of space, comfort, and lifestyle.

2433 Grand Teton Circle, Winter Park

$469,000
3 Beds 2 Baths Casa Aloma SubDv. 32792 Zip Code
Okay, let's talk about this one. Yes, there's green carpet. Yes, it needs your vision. I know exactly what you're thinking right now. But hear me out, because this house has some things going for it that are genuinely hard to find. Start with the location. In under 10 minutes in any direction, you could be having lunch on Park Ave, shopping at Altamonte Mall, or launching your boat up in Maitland. That kind of range is rare in Central Florida, and this spot has it. And there's no HOA here, which if you know, you know. Then there's the pool. A real pool, tucked behind a block wall for total privacy, so you can actually enjoy it without the whole street watching. That kind of setup doesn't come around often. This is a 3 bedroom, 2 bath home with real bones and real space. The layout gives you room to breathe, and the systems that actually matter have already been taken care of. Water heater, brand new in 2026. HVAC, also brand new in 2026. Roof was done in 2025. Plumbing was updated in 2017. So the expensive, unglamorous stuff, the stuff that actually protects your investment, is already handled. The home has been professionally cleaned and pressure washed, so it's not just clean, it's move in ready clean. You could genuinely move in as is and update it slowly, on your own timeline, as your taste and budget allow. No rush. No pressure. Just a solid home with good bones, a pool, an unbeatable location, and all the boring but important stuff already done for you. Sometimes the right house isn't the one that's already finished. It's the one that's ready for you to finish it.

2703 Tierra Circle, Winter Park

$399,000
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

$1,800,000
5 Beds 5 Baths Osceola Shores Sec 02 SubDv. 32789 Zip Code
Short Sale. Welcome to this luxury, home in the heart of Winter Park. Less than a mile away from Park Ave. Winter Park that offers entertainment, restaurants, farmers market and so much more. A beautiful contemporary style home with modern interior finishes. Featuring an open floor plan, 5 bedrooms, 4.5 baths, a loft/flex space, media room, 2 study areas, front porch, back patio, lanai and so much more. Corner lot and privacy. Engineered hard wood floors through out the house and tile in utility rooms. 2 laundry rooms for convenience, located on 1st and 2nd floor of the home. Private backyard setting, a very large pool, an outdoor entertainment area featuring a kitchen and a fireplace and a screened in lanai. Metal Roof with Solar panels. A gas stove with large island and lots of space for entertainment. This home has a lot to offer in the most desirable location. Schedule your showing today.

281 Brewer Avenue, Winter Park

$185,000
2 Beds 3 Baths Hidden Oaks Condo Ph 10 SubDv. 32792 Zip Code
This charming 2-bedroom, 2.5-bathroom townhome style condo offers the perfect blend of comfort and convenience. Enjoy the peace of mind that comes with a new AC (2025), a new roof (2021), newer water heater (2019) and new refrigerator and dishwasher ensuring your home is both energy-efficient and well-maintained. The entire first floor features ceramic tile, while the upstairs boasts beautiful laminate wood flooring—no carpet here! Both bedrooms are located upstairs, each with its own ensuite bathroom and additional storage above the mirrors. Downstairs, you'll find ample space for entertaining or simply relaxing, enhanced by the convenience of a wet bar. Located just minutes from UCF and Full Sail University, this condo is perfect for anyone looking to enjoy the vibrant local community without the long commute! With shopping, dining, and recreational activities nearby, you'll have everything you need right at your fingertips. Don’t miss out on this fantastic opportunity—schedule a showing today!

7450 Wynnewood Square Unit 189, Winter Park

$290,000
3 Beds 3 Baths Windward Square Sec 1 SubDv. 32792 Zip Code
Welcome to 2487 Harbour Way, a spacious single-story townhome offering 3 bedrooms, 3 full bathrooms, and 1,803 square feet of comfortable living space. The practical layout features inviting living and dining areas, a well-equipped kitchen, central air, and a walk-in closet. Outside, garden space, lighting, and sidewalks add to the home's appeal. Enjoy a low-maintenance lifestyle in Windward Square, where residents have access to a community pool and playground, with the pool included in the low monthly HOA fee. Conveniently located near schools, parks, shopping, dining, and everyday essentials, this Winter Park property offers space, convenience, and community amenities in one appealing package. Schedule your private showing today!

2487 Harbour Way, Winter Park

$750,000
4 Beds 3 Baths Landings At Hawks Crest SubDv. 32792 Zip Code
Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office or a fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic trails and private access to Lake Howell. The community is also conveniently located near local favorites, including Kelly's Ice Cream, Foxtail Coffee and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.

1418 Lone Feather Trail, Winter Park

$4,250,000
4 Beds 6 Baths Alexander Place SubDv. 32789 Zip Code
Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winning contemporary estate is a masterclass in modern design. Tucked away on a prestigious cul-de-sac between Lake Osceola and the iconic Alfond Inn, the residence offers unparalleled privacy just two blocks from Park Avenue's world-class amenities. A striking entryway with 10-foot mahogany doors reveals a secluded courtyard oasis, featuring a sparkling pool framed by lush Signature landscaping. Inside, expansive living spaces with soaring 14-foot ceilings and a dramatic 40-foot gallery wall flow seamlessly to the outdoors, creating an effortless connection between interior elegance and open-air entertaining. The sleek, state-of-the-art kitchen is curated with premium Monogram, JennAir, and Gaggenau appliances, complemented by a sophisticated wet bar and an intimate media lounge. Ascend the floating staircase or private elevator to the primary sanctuary, which exclusively commands the entire second level. This lavish retreat features a spa-inspired bath with a smart-controlled shower, an oversized marble vanity, and three private terraces. The estate is further elevated by a first-floor guest suite, an executive office, a fitness studio with an en-suite steam shower, and a versatile poolside casita. Integrated smart home technology, automatic Lutron shades, whole-house generator and a three car garage provide ultimate modern convenience. Every element of this residence reflects intentional design, innovation, and timeless elegance, embodying the pinnacle of world-class Winter Park living.

229 Alexander Place, Winter Park

$849,949
5 Beds 4 Baths Winter Park Pines SubDv. 32792 Zip Code
LIGHTING FAST RESPONSE - FULLY RENOVATED 5-BEDROOM, 4-BATH WINTER PARK ESTATE Welcome to 724 Monmouth Way, a beautifully reimagined five-bedroom, four-bath estate designed for comfortable family living, elegant entertaining, and everyday luxury. Renovated in 2026, this spacious home features thoughtfully separated bedroom wings, impressive living areas, abundant natural light, and designer finishes throughout. The expansive 13-by-22-foot primary suite offers enough space for a private sitting area, reading retreat, or lounge within the bedroom. The luxurious primary bathroom features a double vanity, an oversized shower with dual showerheads, a heated smart toilet, and a six-foot freestanding soaking tub positioned beneath a built-in skylight. Marble fluted accent walls surrounding the tub and shower create a dramatic, spa-like atmosphere. A generous 7-by-8-foot walk-in closet provides abundant storage. At the heart of the home is a newly designed, chef-inspired kitchen featuring a striking 9-by-5-foot double-waterfall island, extensive cabinetry, exceptional storage, a custom range hood surround, and an elegant cabinet column that gives the kitchen a truly distinctive designer look. Two large skylights above the kitchen and adjoining casual dining area fill the space with natural light, creating a bright, open, and inviting atmosphere throughout the day. The adjoining butler’s pantry functions as a second kitchen and includes its own sink and faucet, full-size refrigerator space, extensive cabinetry, and additional countertop space. Prepare meals, store small appliances, and keep entertaining messes neatly tucked away from the main kitchen. A guest bedroom located near the primary suite includes its own private ensuite bathroom. This flexible left-wing space is ideal for overnight guests, a nursery, private office, fitness room, or multigenerational living arrangement. On the opposite side of the home, the right bedroom wing offers added privacy and separation from the primary suite. This hallway includes three additional spacious bedrooms, a full bathroom, and a convenient half bathroom. The large formal living room is filled with natural light from its front-facing windows. A separate 22-foot family room creates an impressive gathering space and features a dramatic 10-foot linear fireplace, making it the perfect setting for holidays, celebrations, movie nights, and everyday relaxation. Outside, the large, thoughtfully designed backyard features newly installed Zoysia grass, a private putting green, and naturally shaded areas perfect for relaxing, entertaining, or enjoying the Florida lifestyle. Major improvements include a new roof, electrical system, plumbing, and water heater completed in 2026, along with an HVAC system installed in 2019. This exceptional Winter Park home combines generous living space, modern luxury, flexible accommodations, dramatic natural light, and extensive renovations in one remarkable property.

724 Monmouth Way, Winter Park

$2,195,000
4 Beds 5 Baths Conwill Estates SubDv. 32789 Zip Code
Positioned in one of Winter Park's most desirable neighborhoods, this exceptional French Mediterranean residence is just moments from Phelps Park, the Winter Park YMCA, Lakemont Elementary, and Interlachen Country Club. Built by MichaelCharles Homes with interiors by Wolfe-Rizor Interiors, the home pairs timeless architecture with refined contemporary design, abundant natural light, and exceptional craftsmanship. The thoughtfully designed floor plan offers 4 bedrooms, 4 full bathrooms, and 1 half bathroom. The first-floor primary suite features a spa-inspired bathroom and an expansive custom walk-in closet with dedicated his-and-her wardrobe areas. A flexible adjoining room is ideal as a private office, nursery, fitness room, or optional fifth bedroom. On the opposite wing of the home, the private guest suite includes a full bathroom and walk-in closet. The second floor features two additional guest bedrooms, each with access to a full bathroom, along with a spacious loft that serves as the perfect media room, playroom, or secondary living area. At the heart of the home, the chef's kitchen showcases a large center island, custom cabinetry, and premium finishes. Oversized glass doors open to a covered lanai with outdoor dining, grilling space, and a resort-style pool. Framed by mature Japanese maple trees, the backyard offers exceptional privacy and a spacious lawn for recreation or entertaining. Situated on a quiet, oak-lined street, this custom-built home reflects the quality in every detail, presenting a rare opportunity to own an exceptional residence in the heart of Winter Park.

1750 Walnut Avenue, Winter Park

$569,000
3 Beds 3 Baths Fairshores Place SubDv. 32789 Zip Code
Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.

2803 Riddle Drive, Winter Park

$255,000
3 Beds 2 Baths Cedarwood Village 1 SubDv. 32792 Zip Code
Rare end units like this don't come around often! Welcome to 2450 Grand Teton Circle, tucked away in the well-maintained, established community of Cedarwood Village in Winter Park. This 3-bedroom, 2-bath home is filled with natural light thanks to its end-unit location, and the open layout makes it easy to relax, entertain and enjoy everyday living. The spacious living and dining areas flow together nicely, while the kitchen offers plenty of room to cook, gather, and stay connected with family and friends. Over the past several years, this home has been thoughtfully updated, giving the next owner peace of mind. Major improvements include a new roof, skylights, HVAC system, water heater, kitchen appliances, washer and dryer, updated LED lighting, and fresh interior paint. Both bathrooms have been beautifully remodeled, the home has been replumbed by the HOA, and the primary closet has been enhanced with custom shelving. Additional updates include new flooring in the secondary bedrooms, updated window blinds, and thoughtful finishing touches throughout. The private screened lanai has been transformed into a cozy outdoor retreat with fresh paint, a ceiling fan, new screens and screen door, string lighting, and decorative greenery—making it the perfect place to enjoy your morning coffee or unwind after a long day. Life here is easy. Cedarwood Village is a beautifully maintained, established community featuring a community pool and Clubhouse for your special events, tennis courts, and pickleball courts. The HOA has also recently repainted the exterior of the buildings, helping keep the neighborhood looking fresh and inviting. Best of all, this home is value priced, giving you an incredible opportunity to own in desirable Winter Park without the premium price tag. You're just minutes from Winter Park's shopping and dining, Full Sail University, UCF, major employers, and convenient access to SR-417 and downtown Orlando. If you've been looking for a move-in-ready home in a fantastic location with years of thoughtful updates already completed, this rare end unit is definitely worth a look!

2450 Grand Teton Circle Unit 2450, Winter Park

$2,569,999
5 Beds 5 Baths Orange Grove Sub SubDv. 32789 Zip Code
Under Construction. Experience the very best of Winter Park living with this stunning new construction home, where sophisticated design, luxury finishes, and an incredible location come together on a quiet tree-lined street. Ideally positioned just a short golf cart ride from Park Avenue, the YMCA, and Interlachen Country Club, this home offers the perfect combination of privacy, convenience, and refined Winter Park living. From the moment you step inside, an impressive foyer greets you, showcasing intricate marble mosaic tile that sets the tone for the craftsmanship found throughout. The open-concept floor plan flows effortlessly into the main living spaces, where the spacious living room serves as the centerpiece of the home with elegant archways, custom shelving with LED underlighting, warm wood beam accents, and a stunning stone-wrapped fireplace creating the perfect balance of sophistication and comfort. Designed for both everyday living and entertaining, the dining room features a beautiful dry bar complete with a wine refrigerator, while the chef’s kitchen is truly the heart of the home. Outfitted with Calacatta quartz countertops, a paneled built-in refrigerator, a full suite of Thermador appliances, and a spacious walk-in pantry, every detail has been thoughtfully selected to deliver both style and functionality. The first-floor primary suite provides a private retreat with generous proportions and a spa-inspired bathroom featuring marble mosaic tile, dual vanities, a freestanding soaking tub, an expansive walk-in shower, and a large walk-in closet. A rare additional first-floor guest suite adds incredible flexibility for family and visitors. Upstairs, the home continues to impress with a spacious loft, a conveniently located laundry room, and three additional bedrooms, offering plenty of room for everyone. Step outside and experience your personal outdoor oasis with a spacious covered lanai featuring a full summer kitchen overlooking the sparkling pool and spa. The oversized backyard provides an abundance of green space, creating the perfect setting for relaxing, entertaining, or enjoying time with family. Additional highlights include impact-rated windows and doors, premium finishes throughout, and an unbeatable location surrounded by some of Winter Park’s most desirable amenities. This is a rare opportunity to own a brand-new home combining thoughtful design, exceptional craftsmanship, and one of Central Florida’s most sought-after lifestyles.

1754 Taylor Avenue, Winter Park