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

$650,000

2 Beds ⋅ 2 Baths ⋅ Mack Peter Rev SubDv. ⋅ 32789 Zip Code

Rare opportunity to own a charming Duplex on a corner lot in the heart of Winter Park! Located walking distance to Mead gardens and Orange Ave, and less than a mile from Park Ave. shopping and dining, this incredible investment is positioned for convenience and enjoyment! Across the street is a community garden. Whether you are looking for an investment property to add to your portfolio or a primary residence with income generating capabilities, this property has it all! New roof in 2024, and new windows and exterior paint in 2026. AC's updated in 2024 & 2025. Schedule a tour to secure this incredible investment today!

901 Harmon Avenue, Winter Park

$1,950,000

32792 Zip Code

Rare opportunity to acquire an established church property on 6.21 acres with outstanding frontage and visibility along one of the area's busiest corridors. The existing sanctuary, ample parking, and expansive grounds provide an excellent opportunity for a growing congregation to establish or expand its ministry. For investors and developers, the property's Future Land Use designation for multifamily offers exceptional long-term redevelopment potential in a high-demand location. A unique offering with immediate functionality and future possibilities.

3075 N Goldenrod Road, 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

$425,000

Eastgate Sub SubDv. ⋅ 32792 Zip Code

A great opportunity to own land in one of Winter Park's most sought-after pockets. This property's true value lies in its prime homesite. You can build your dream home or renovate to suit, all while capturing the location that can't be replicated. Tucked in an established, tree-lined neighborhood minutes from Park Avenue's boutiques and dining, Winter Park's chain of lakes, and easy access to I-4, this address puts you at the center of it all. Zoned for top-rated Winter Park schools, this is the kind of location families compete for. Whether you're an investor, builder, or buyer looking to create something custom, this is a foundation worth building on. Land + location + schools — the trifecta that makes Winter Park real estate hold its value.

1909 Taylor Avenue, Winter Park

$409,900

3 Beds ⋅ 2 Baths ⋅ Justamere Camp Rep SubDv. ⋅ 32789 Zip Code

Virtually Staged. Conveniently located just minutes from I-4, downtown Orlando, and Winter Park, this versatile home offers the perfect blend of comfort, flexibility, and location. The upper level features two bedrooms and one full bath, while the lower level includes one bedroom and one full bath. Each floor has its own private entrance and full kitchen, making it ideal for multi-generational living, rental income, a guest suite, or added privacy. Situated on a beautiful, tree-lined dead-end street, the property offers a peaceful setting while remaining close to shopping, dining, and entertainment. Inside, you'll find contemporary fixtures, stylish finishes, updated appliances, and an abundance of natural light throughout. The spacious backyard and inviting seating area provide the perfect space to relax or entertain family and friends. Major updates include a recently replaced roof, HVAC system, and electrical panel, offering added peace of mind. Some photos have been virtually staged to help showcase the home's layout and potential.

2568 Lotafun Avenue, Winter Park

$1,275,000

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

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

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

$325,000

2 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Roof 2018 | HVAC 2020| Set on a deep, tree-canopied lot in one of Winter Park's most desirable established neighborhoods, this charming single-story concrete-block home blends timeless character with everyday convenience. A grand oak shades the front lawn, helping cool the home and lower energy costs, while durable masonry construction, a dimensional-shingle roof, and a full-length driveway leading to a covered carport deliver lasting value and practical, protected parking with an attached workshop & storage room. A generous screened front porch offers a breezy, bug-free spot for morning coffee or evening relaxation before you step inside to a spacious living room featuring gleaming refinished hardwood floors and a wood-burning fireplace framed by a classic white mantel with fluted columns. A large picture window floods the room with natural light, and a graceful curved archway, one of the home's most distinctive architectural details, leads you deeper into the thoughtfully connected floor plan. The kitchen is efficiently designed with cabinetry lining both walls for ample storage, laminate counters, under-cabinet lighting, and a full stainless-steel appliance suite. A double sink offers plenty of room to work and a large window overlooks the lush backyard, with a rear door providing easy access for grilling and entertaining. The adjacent, light-filled dining room offers flexible space that works well for family meals, a home office, or a quiet reading nook. Two comfortable bedrooms feature hardwood floors, ceiling fans with lights, and built-in closets, one with built-in shelving, while the bright corner primary enjoys windows on two walls for excellent light and cross-ventilation. A full bathroom is finished with a tiled tub-and-shower combination, a wood vanity, and a frosted privacy window that brings in daylight while maintaining seclusion. Out back, a large, fully fenced yard framed by mature oaks, palms, and established privacy hedges creates a secluded, park-like retreat with ample room to garden, play, entertain, or add a pool. Just minutes from historic Park Avenue, residents enjoy boutique shopping, award-winning restaurants, sidewalk cafés, museums, and year-round community events, with nearby College Park adding popular dining, breweries, and specialty shops. Outdoor recreation abounds with Dubsdread Golf Course, Mead Botanical Garden, Kraft Azalea Garden, and numerous parks close by, plus easy access to Winter Park's scenic chain of lakes and walking trails, all without requiring waterfront ownership. Commuting is effortless thanks to convenient access to Interstate 4, Fairbanks Avenue, Lee Road, SR 426, and SR 436, providing quick connections throughout Central Florida. Downtown Orlando, the Orlando Health and AdventHealth medical campuses, and major employment centers are all within easy reach. With excellent shopping, grocery stores, entertainment, and cultural attractions nearby, this sought-after location offers the perfect balance of quiet residential living and close proximity to everything Central Florida has to offer. This listing is for a single home and lot at 846 Driver Ave, but the owner would also consider selling the adjacent home next door to the North at 844 Driver Ave. If you are interested in purchasing both homes simultaneously, contact listing agent for more details.

846 Driver Avenue, Winter Park

$525,000

3 Beds ⋅ 4 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code

Beneath mature oak trees in The Quarters at Winter Park, this townhome-style condominium presents a rare opportunity to own a spacious, architecturally distinctive residence in one of Winter Park's most established communities. Priced to reflect its as-is condition, the home offers exceptional potential for a buyer ready to personalize the space. A gated brick courtyard and covered front porch lead to light-filled living and dining areas featuring engineered hardwood flooring and a wrought-iron staircase. The kitchen offers granite countertops, a gas range and opens to the family room, where a gas fireplace and skylight create a welcoming gathering space. A private screened courtyard connects the residence to the detached two-car garage. Upstairs, the primary suite spans more than 300 square feet and features a custom walk-in closet and dual-sink en-suite bath. Two additional bedrooms include one with a private en-suite bath and another with access to a balcony overlooking the tree-lined street. Ideally just minutes from Park Avenue, Rollins College and Seven Oaks Park, this residence offers the opportunity to renovate and customize a home in one of Winter Park's most sought-after communities. Sold as is, with an inspection report available upon request.

1134 Washington Avenue Unit 13C, Winter Park

$775,000

4 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. This move-in-ready home combines elevated finishes, abundant natural light, a flexible split-bedroom floor plan, and an exceptional location near the shopping, dining, and cultural attractions that make Winter Park one of Central Florida’s most desirable communities. At the center of the home is a completely redesigned kitchen that is both stylish and highly functional. New cabinetry, quartz countertops, stainless steel appliances, generous storage, and an oversized island with bar seating create an inviting setting for everyday meals and entertaining. A beautiful picture window frames views of the lush backyard and fills the kitchen with natural light. The open living spaces flow seamlessly together over wood-look tile flooring, while fresh interior paint, updated fixtures, and an electric fireplace add warmth and a polished contemporary feel. Privately positioned on one side of the home, the expansive primary suite feels like a retreat of its own. The suite includes a custom designed walk-in closet and a beautifully designed bathroom with separate vanities, a freestanding soaking tub, an oversized walk-in shower, and a private water closet. Three additional bedrooms are located on the opposite side of the home, providing separation and flexibility for family members or overnight guests. The outdoor setting is equally impressive. The enormous, fully fenced backyard has been lovingly maintained and features mature greenery, privacy, and plenty of room for entertaining, recreation, gardening, pets, or a future outdoor living retreat. Bonus: there is additional parking on the west side of the home that is accessible from the backyard - perfect for hosting or entertaining! A cobblestone driveway enhances the home’s curb appeal, while notable improvements include replacement of the HVAC system and ductwork in 2016, numerous plumbing updates, and extensive interior renovations. Enjoy a location that places the best of Winter Park within easy reach. The home is conveniently located near the Winter Park YMCA, Lakemont Elementary School, Phelps Park, Rollins College, and the Winter Park Chain of Lakes - not to mention all of the boutiques, restaurants, museums, & cafés, and community events of historic Park Avenue. Baldwin Park, Winter Park Village, and Audubon Park are also just minutes away, offering even more options for dining, shopping, entertainment, and outdoor recreation. This is an exceptional opportunity to enjoy a gorgeous, fully updated home in the highly desirable in-town Winter Park address. Schedule your private showing and experience the lifestyle, location, and thoughtful design of 1562 Arbor Park Drive.

1562 Arbor Park Drive, Winter Park

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