Location: Winter Park
Keyword(s): Winter Park High
Keyword(s) High School: Winter Park High
Do Not Show Listings
1210 FAIRWAY DR, WINTER PARK, FL 32792
$549,000Listed 04/13/2026 11:42AM MLS ID: O6398533
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1737 Built: 1979 Tax: $7,265 (2025)Community: Golfside Sec 3Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,265
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Welcome home to this beautiful single-story Pool home in the Golfside community of Winter Park. Offering 3 bedrooms, 2 bathrooms, and 1,737 square feet of living space, this home features a spacious and inviting layout designed for both everyday living and entertaining. Upon entry, you are welcomed into the living room, while an adjacent dining room combination provides additional flexible gathering space. The family room offers French door access to the covered rear patio, creating a seamless indoor-outdoor flow to the expansive backyard, perfect for hosting family and friends.The kitchen opens to the main living areas and is equipped with stainless appliances, stone countertops, and ample cabinet space. A hallway just off the family room leads to all three bedrooms and two full bathrooms, including a spacious primary suite with an ensuite bath. Additional features include engineered wood throughout the main living areas, extra storage closets, an interior laundry room, and a 2-car garage.Ideally located near Winter Pines Golf Club, this home also offers convenient access to I-4 and SR-417, making it easy to reach shopping, dining, entertainment, downtown Orlando, the airport, area attractions, and the beaches.
Listing is courtesy of: CENTRAL FLORIDA PRIME REAL ESTATE LLC (407-404-4041)
Listing Agent: Albin Hubscher (407-404-4041)
240 N PHELPS AVE, WINTER PARK, FL 32789
$2,279,00035 Days on yellowkey MLS ID: O6389035
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2889 Built: 2026 Tax: $6,605 (2025)Community: Sylvan HeightsSpa: NoSingle Family
Taxes:$6,605
Remarks: Brand new construction luxury home in the heart of Winter Park! This stunning two-story custom residence offers nearly 3,000 sq ft of heated living space with 5 bedrooms and 4 1/2 bathrooms. A soaring two-story foyer creates a dramatic first impression and opens into an expansive great room featuring 12-foot ceilings, wide-plank flooring, and abundant natural light. The family room showcases a custom paneled feature wall with a sleek built-in electric fireplace, creating a striking focal point for the space. The gourmet kitchen is designed for both everyday living and entertaining, highlighted by a large center island with seating, European slab cabinetry, premium hardware, designer countertops, and high-end appliances. Ample storage and a clean modern aesthetic make this kitchen as functional as it is beautiful. Tucked beneath the staircase is a custom wine storage feature, adding a unique luxury detail. The first floor also includes a private guest suite with its own en suite bathroom, perfect for visitors or multi-generational living. A dedicated home office provides a quiet workspace, while the main-floor laundry room adds convenience. Outside, a professionally designed outdoor kitchen extends the living space and creates the perfect setting for year-round entertaining under the Florida sky. Upstairs, the luxurious primary suite serves as a private retreat. The spacious walk-in closet features a fully custom organization system, while the spa-inspired primary bathroom includes a dual-sink vanity, elegant freestanding soaking tub, and oversized walk-in shower with premium tile work. Three additional bedrooms complete the second floor. Two share a beautifully appointed Jack-and-Jill bathroom, while the fourth bedroom features its own private en suite bath, offering flexibility for guests or family members. Located at 240 N. Phelps Avenue, this home places you just minutes from Winter Park’s iconic Park Avenue — a vibrant destination known for its boutique shopping, award-winning restaurants, art galleries, and charming sidewalk cafés. Residents enjoy access to top-rated schools, including Winter Park High School, as well as renowned cultural destinations such as the Morse Museum of American Art and the Polasek Museum. Outdoor lovers will appreciate nearby Central Park, Mead Garden, and the scenic Winter Park Chain of Lakes. Conveniently located near I-4, SR-417, downtown Orlando, Lake Nona Medical City, UCF, and Orlando International Airport, this home offers the perfect balance of luxury, convenience, and the timeless charm that makes Winter Park one of Central Florida’s most sought-after communities. Schedule your private showing today.
Listing is courtesy of: GOLDEN GROUP REALTY LLC (407-990-5905)
Listing Agent: Milena Fernandes (407-990-5905)
543 E LAKE SUE AVE, WINTER PARK, FL 32789
$1,875,0004 Days on yellowkey MLS ID: O6397480
1 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3657 Built: 1986 Tax: $14,126 (2025)Community: Lake Virginia Pt RepSpa: NoSingle Family
Taxes:$14,126
Elementary School: None
Middle School: Audubon Park K-8
Remarks: Under contract-accepting backup offers. Welcome to Timberlane Shores—one of Winter Park’s most desirable neighborhoods! This beautiful 4-bedroom, 4.5-bath home sits on over a third of an acre in a quiet, tucked-away location with gorgeous updated landscaping. Inside, you’ll find wide-plank hardwood floors throughout and a thoughtfully designed floor plan with separate living and dining rooms plus a spacious family room. The bright kitchen features white cabinetry with pull-out drawers, marble countertops, subway tile backsplash, and newer appliances (2018), including a Sub-Zero refrigerator and Wolf gas 4 burner range. The kitchen opens to a bright sunroom with beautiful wood-like tile floors laid in a herringbone pattern (2018). Such a great space that is filled with natural light—perfect as a casual gathering space or playroom, making this an ideal home for entertaining. The sunroom overlooks the enormous backyard space and large pool area with custom designed pavers (2023). A downstairs guest suite with full bath provides comfort and privacy, while a dedicated office with built-in desks and brand new carpet adds functionality. Upstairs, the oversized primary suite boasts a beautifully appointed bathroom with dual sinks, marble countertops, soaking tub, and separate walk-in shower, along with a custom walk-in closet. Two additional upstairs bedrooms each offer en-suite baths, including one renovated in 2021. Recent updates include new windows (2017), solid wood front door (2021), renovated bath (2021), two new AC units and duct cleaning (2024), and a new roof (2024). This exceptional home offers the perfect blend of style, comfort, and location—truly a must-see.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Lisa Fleming (321-228-8341)
311 E MORSE BLVD #7-19, WINTER PARK, FL 32789
$299,900105 Days on yellowkey MLS ID: O6368912
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 482 Built: 1960Monthly Fee: $870 Tax: $3,161 (2024)Community: Whispering WatersCondo
Taxes:$3,161
Elementary School: Audubon Park K8
Tax Year: 2024
Remarks: One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Welcome to an exceptional opportunity to own a beautifully maintained, move-in ready third-floor, water-view, corner unit studio residence in one of Winter Park’s most coveted locations—directly adjacent to Lake Osceola and just moments from iconic Park Avenue. This rare downtown setting places you within effortless reach of the Winter Park Farmers’ Market, acclaimed dining, boutique shopping, cultural venues, and a picturesque network of lakes and parks. The residence features a bright and open floor plan where the kitchen, dining, and living spaces flow seamlessly, creating an inviting atmosphere ideal for both everyday living and entertaining. Upon entry, you are welcomed by multiple storage closets and a discreet hallway that provides additional storage and convenient access to the full bathroom—an uncommon luxury for a studio-style layout. Sliding glass doors lead to a generously sized, private covered and enclosed balcony overlooking the tranquil interior courtyard, with peaceful views of the community pool and Lake Osceola beyond. This serene outdoor retreat is the perfect setting for morning coffee, evening relaxation, or quiet reflection amid lush surroundings. Residents enjoy a truly low-maintenance lifestyle, with electric, gas, water, sewer, and trash all included in the condominium fee. Building amenities include elevator access to the third floor, on-site management, a community laundry facility, and beautifully appointed common areas. The property also features expansive outdoor patios overlooking Lake Osceola, a resident club room, and immediate access to the community pool. Located within Whispering Waters, a highly desirable 55+ community, this residence is ideally suited as a primary home, seasonal retreat, or elegant in-law suite—offering timeless Winter Park living with unmatched convenience and charm.
Listing is courtesy of: TURN-KEY MOVES REALTY (407-796-2221)
Listing Agent: Mathew Kelly (407-796-2221)
3054 BLUEBROOK DR, WINTER PARK, FL 32792
$427,500Listed 04/12/2026 11:09PM MLS ID: O6398450
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1939 Built: 1973 Tax: $6,422 (2025)Community: Laurel SpgsSingle Family
Taxes:$6,422
Elementary School: Aloma Elem
Remarks: "Open the Doors to Your Dreams" of owning an Affordable Home with a pool in Winter Park. The home features a Spacious Kitchen with Upgraded Cabinets, and stone countertops; Primary bedroom suite is amazing. You will love the layout and upgraded primary bathroom; Beautiful Porcelain tile flooring throughout the home; Large family room with fireplace; Large screened back porch/LANAI. And there is an inground pool in the back yard. You will enjoy entertaining in this home featuring a gourmet kitchen with granite countertops, and stainless steel appliances. This property may qualify for Seller Financing (Vendee). If property was built prior to 1978, Lead Based Paint Potentially Exists. Come tour this home today. We expect this one to sell quickly.
Listing is courtesy of: WEATHERSPOON REALTY INC (407-878-4468)
Listing Agent: Eugene Weatherspoon (407-878-4468)
2919 BOWER RD, WINTER PARK, FL 32792
$779,00025 Days on yellowkey MLS ID: O6391025
3 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2325 Built: 1971 Tax: $9,857 (2025)Community: Winter Park PinesSingle Family
Taxes:$9,857
Remarks: Beautifully updated 3BR/2BA pool home in the highly sought-after Winter Pines community of Winter Park! This move-in ready home offers a bright, open layout with multiple living spaces, perfect for both everyday living and entertaining. The upgraded kitchen features stainless steel appliances, granite countertops, breakfast bar, custom cabinetry, and a farmhouse-style undermount sink, all opening to a spacious dining area with a stunning exposed brick fireplace. A newly enclosed and fully air-conditioned back room (converted from the former porch) offers exceptional flex space—perfect for a bonus room, playroom, or additional living area. Designed to maximize Florida living, this space features an expansive sliding glass door that seamlessly blends indoor and outdoor living, while a separate dedicated HVAC system ensures optimal comfort year-round. The primary suite includes a walk-in closet, dressing area, and en suite bath with dual-sink granite vanity and step-in shower. Just off the primary bedroom is a newly added office/nursery space, perfect for working from home or a private retreat. Split floor plan with two additional generously sized bedrooms and a full bath for added privacy. Enjoy Florida living outdoors with a spacious patio, sparkling pool, and large backyard featuring brand-new sod—perfect for entertaining or relaxing. Additional upgrades include fresh paint and a high-end seamless metal roof. Prime location just minutes to Cady Way Park, shopping, dining, and zoned for top-rated schools. Don’t miss this one—schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Nick Mckee (407-913-0171)
647 RANDY LN, WINTER PARK, FL 32789
$1,795,00035 Days on yellowkey MLS ID: O6387217
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2851 Built: 1957 Tax: $5,627 (2025)Community: TimberlaneSingle Family
Taxes:$5,627
Remarks: Welcome to 647 Randy Lane in Winter Park. This is a rare opportunity to own a designer residence in one of the area's most sought-after neighborhoods, offered for the first time in over 10 years. Situated on a spacious corner lot, 0.36 acres, this meticulously maintained home showcases timeless charm paired with modern luxury. Lush, mature landscaping surrounds an oversized private pool, expansive patio and generous backyard, creating a Florida outdoor living experience ideal for entertaining or relaxing year-round. Inside, the home features an open-concept floor plan designed for both comfort and style. The chef's kitchen stands out, appointed with quartz countertops, premium Wolf double ovens and a built-in Sub-Zero refrigerator, delivering high-end performance with sophisticated design. Seamless indoor-outdoor flow enhances the living experience, leading to a resort-style backyard retreat complete with ambient lighting, perfect for evening gatherings and weekend enjoyment. Ideally situated minutes from Park Avenue's renowned dining, boutique shopping, and cultural attractions, this home offers unparalleled convenience in the heart of Winter Park. Located in one of the area’s most desired school districts, including Audubon K-8 and Winter Park High School. The home is equipped with updated features like a newer roof (2024), solar panels (2024), resurfaced pool and tile (2021), well irrigation, tankless gas water heater, oversized indoor laundry room and more. This exceptional property blends luxury, location and lifestyle-making it a standout opportunity in the Winter Park real estate market.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Sara Cambron (321-277-8444)
850 JUANITA RAEL, WINTER PARK, FL 32789
$1,425,00096 Days on yellowkey MLS ID: O6370568
1 Days Off yellowkey (back on 1/12/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2306 Built: 1966 Tax: $6,218 (2024)Community: Green Oaks Rep 03Spa: NoSingle Family
Taxes:$6,218
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Location, location, location. Sought after location on the North end of Park Avenue. Avoid the traffic in and out of Downtown Winter Park while being minutes away from everything on the Avenue. One of the very few single level homes of this quality in Winter Park 32789. Single story ranch on a lovely, private, large corner lot. 2306 heated and cooled square feet. Primary bedroom en-suite with 3 additional bedrooms and 2 additional bathrooms, 15,000 sq ft large corner lot with oversized side-entry garage and over-sized laundry room. Magnificent, private back yard oasis with pool and covered veranda. Freshly painted inside and outside. New lovely oak wood floors, newer roof and windows, new hardware and updated lighting. Oversized two car garage with storage. This home is move-in ready and all the model-home furniture is available to purchase as well.
Listing is courtesy of: PHIL KEAN REAL ESTATE LLC (407-982-2265)
Listing Agent: Brad Grosberg (321-439-1494)
3312 HEARTWOOD AVE, WINTER PARK, FL 32792
$465,000177 Days on yellowkey MLS ID: O6352582
REDUCED by $19,000 (3.9%) on 04/08/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2878 Built: 1983 Tax: $2,183 (2025)Community: Bel-Aire PinesSpa: NoSingle Family
Taxes:$2,183
Remarks: One or more photo(s) has been virtually staged. A family home with a private entrance to a large In-Law suite upstairs and private entrance to spacious downstairs living. The downstairs has three (3) bedrooms and two (2) baths on a split floor plan with plenty of room to entertain. This home is move-in ready and recently had a new roof installed which comes with a five (5) year warranty which covers all repairs and is transferrable. All systems in this home have been lovingly maintained for the next owner. No repairs needed. The yard is completely fenced in for safety and has flower beds already installed if gardening is your thing, along with a storage shed and irrigation system for the front yard. Come take a look! PLEASE SHUT OFF LIGHTS AND FANS WHEN SHOWING IS COMPLETE and END SHOWING IN SENTRILOCK.
Listing is courtesy of: MID-STATE PROPERTIES PSL LLC (561-843-9537)
Listing Agent: Stacy Morano (561-843-9537)
3021 AARON BURR AVE #3, WINTER PARK, FL 32792
$140,000Listed 04/12/2026 11:07PM MLS ID: S5147382
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1090 Built: 1974Monthly Fee: $479 Tax: $1,992 (2025)Community: ColoniesCondo
Taxes:$1,992
Elementary School: Cheney Elem
Remarks: Townhouse opportunity—ideal for either personal residence or investment—featuring 2 bedrooms and 2.5 bathrooms. Conveniently located near supermarkets, shops, universities, and public transportation. At closing, all outstanding HOA special assessments will be paid off. The Townhome is rent $1,600. The unit is located in Winter Park Area HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.
Listing is courtesy of: NAIM REAL ESTATE LLC (818-268-9917)
Listing Agent: Daiana Garcia Medrano (321-315-4686)
851 MILES AVE #13, WINTER PARK, FL 32789
$209,999116 Days on yellowkey MLS ID: O6368234
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 808 Built: 1984 Tax: $2,694 (2025)Community: Aragon CondoCondo
Taxes:$2,694
Remarks: Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor condo in the heart of charming Winter Park, FL 32789! Meticulously updated since 2023, this home blends modern luxury with effortless comfort and is truly move-in ready. As you step inside, you’ll be greeted by elegant porcelain tile flooring throughout—offering both durability and a look that’s easy to maintain. The heart of the home, the kitchen, has been completely reimagined with sleek granite countertops, fresh cabinetry, and contemporary finishes that make cooking and entertaining a joy. The bathroom has also received a full renovation, featuring granite countertops and updated fixtures that enhance both style and function. With thoughtful design at every turn, this condo feels fresh, bright, and uniquely yours. Situated on the second floor for added privacy and natural light, this unit provides a peaceful retreat while still being close to all that Winter Park has to offer. Enjoy being minutes from Park Avenue, with its array of boutique shopping, acclaimed restaurants, art galleries, and outdoor markets. Explore scenic parks, lakeside boat tours, cultural attractions, and community events that make Winter Park one of Central Florida’s most desirable places to live. Whether you’re searching for your next home or an exceptional investment opportunity, 851 Miles Ave #13 showcases stylish updates, quality finishes, and a location you’ll love. Don’t miss your chance — schedule a showing today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Eric Campbell (321-279-8941)
1507 GOLFSIDE DR, WINTER PARK, FL 32792
$975,00011 Days on yellowkey MLS ID: O6395355
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2003 Built: 1981 Tax: $2,783 (2025)Community: Greenview At Winter PinesSingle Family
Taxes:$2,783
Remarks: One or more photo(s) has been virtually staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring throughout. Updates include (but definitely not limited to) BRAND new kitchen with Stainless Steel Appliances, new cabinets & quartz countertops. Formal living & dining rooms PLUS Family room with vaulted ceilings featuring a new electric fireplace for amazing ambiance and sliding doors inviting you to new brick pavered 31x 11 screened porch overlooking newly refinished sparkling pool & golf course (no rear or side neighbors!!) Bedroom wing of home offers a large inside laundry room, beautiful guest/pool bath with dual sinks & shower/tub and 2 fresh guest bedrooms. THE PRIMARY SUITE has been thoughtfully remodeled with sliding doors to pool, AMAZING primary bath with oversized work-of-art shower with dual shower heads, dual vanity, separate water closet & HUGE walk-in closet! Extras include: NEW double paned windows & 3 sliding doors to pool/patio, crown molding, NEW roof November 2024, oversized 2 car garage, NEW landscaping, all NEW ceiling fans & light fixtures, NO HOA!! Zoned for Brookshire Elementary, Glenridge Middle & Winter Park High. WELCOME HOME!
Listing Agent: Catherine D'Amico (407-252-3210)
720 W WEBSTER AVE, WINTER PARK, FL 32789
$550,00039 Days on yellowkey MLS ID: G5108643
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1356 Built: 1950 Tax: $5,128 (2024)Community: Carver TownSingle Family
Taxes:$5,128
Remarks: One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! Welcome to 720 W Webster Avenue, a beautifully renovated home in the heart of historic Carver Town in Winter Park—one of the most sought-after locations in Central Florida. Just a short walk to downtown Winter Park, this charming residence blends modern updates with timeless character while offering the lifestyle people move here for. This 3-bedroom, 2-bathroom home contains 1,356 square feet of thoughtfully updated living space designed for both comfort and style. From the moment you step inside, you'll notice the clean, modern feel created by zero carpet throughout the entire home, giving every room a fresh, cohesive look while making maintenance simple and practical. At the center of the home is the fully updated kitchen, featuring beautiful granite countertops, ample cabinetry, and a functional layout perfect for everyday living or entertaining guests. The kitchen serves as the heart of the home, separating the spacious living room from the formal dining room, creating a natural flow between gathering spaces while maintaining distinct areas for relaxing and hosting. Both bathrooms have been fully renovated, showcasing modern finishes that complement the home's updated aesthetic. Each bedroom offers comfortable space, natural light, and flexibility for a primary suite, guest room, or home office. Convenience continues with the laundry closet featuring a newer stackable washer and dryer, maximizing space while keeping everyday tasks simple and efficient. Step outside and you'll find a fully fenced backyard, providing privacy and plenty of room for pets, outdoor gatherings, or simply enjoying Florida’s beautiful weather. The property also includes an oversized covered carport, offering generous parking and protection from the elements. For electric vehicle owners, the carport is already equipped with a Tesla charger, making daily charging effortless and future-ready. What truly sets this property apart is its unbeatable location. Situated in historic Carver Town, you're just minutes from the charm and vibrancy of downtown Winter Park. Enjoy easy access to Park Avenue’s award-winning restaurants, boutique shopping, art galleries, and cultural attractions. Spend weekends exploring the Winter Park Farmers Market, taking a scenic boat tour on the Winter Park Chain of Lakes, or strolling through Central Park’s shaded oak-lined paths. Whether you're looking for a primary residence, a stylish Winter Park retreat, or a home close to everything that makes this city special, 720 W Webster Avenue delivers the perfect combination of location, updates, and lifestyle. Opportunities to own a fully renovated home this close to downtown Winter Park are rare. Schedule your private showing today and experience everything this exceptional property and location can provide!
Listing is courtesy of: SERHANT (646-480-7665)
Listing Agent: Vincent Cordaro (631-834-0816)
1108 FAIRWAY DR, WINTER PARK, FL 32792
$725,00045 Days on yellowkey MLS ID: O6386266
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1677 Built: 1978 Tax: $6,713 (2024)Community: Golfside Sec 03Single Family
Taxes:$6,713
Remarks: Offering WELL BELOW appraised value!! Buyer financing fell through, act quickly this one wont last long. In one of Winter Parks most sought after neighborhoods, take a look at this exceptional 3-bedroom, 2-bathroom pool home with an additional bonus space. Completely reimagined with a designer’s eye, this residence blends high-end aesthetic with the ultimate peace of mind—with a newer roof, A/C, and water heater. Step inside to a Sun-filled sanctuary featuring new luxury vinyl plank flooring and gorgeous tile. The heart of the home is the brand-new chef’s kitchen, featuring custom white oak wood cabinetry, rare Taj Mahal quartzite countertops, and elegant champagne bronze finishes throughout. The kitchen flows seamlessly into the living areas, where new tile work elevates the wet areas for a cohesive, upscale feel. Work from home in style in the dedicated bonus room, an ideal footprint for a private office or creative studio. This home features true functionally for a family to live in everyday. This one of a kind home features a custom in home laundry room, custom vanities, a fireplace made to enhance the homes aesthetic & custom doors through the entire home. Beyond the interior, your private Florida lifestyle awaits. Retreat to the expansive screened-in pool, patio and large backyard. Located just steps from the Winter Park Pines Golf Course and the scenic Cady Way Trail, this home offers more than just a renovation—it offers a lifestyle. Enjoy easy access to the clubhouse for dining, top-rated schools, and the vibrant culture of downtown Winter Park. With every detail thoughtfully curated and major systems already updated, this is the turnkey masterpiece you’ve been waiting for.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Rene Droz, Iii (407-484-8786)
676 DUNBLANE DR, WINTER PARK, FL 32792
$750,000129 Days on yellowkey MLS ID: O6365557
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1827 Built: 1962 Tax: $5,584 (2024)Community: Kenilworth Shores Sec 04Single Family
Taxes:$5,584
Remarks: This meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community could be YOURS! 3 Beds | 2 Baths | Bonus Room | This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full bathrooms, a formal living room, dining area, and a bright breakfast nook. An additional bonus room provides flexible use — ideal as a home office, creative studio, workout space or playroom — all with tranquil views of the pool and backyard. The property features a beautifully landscaped, fully fenced yard and a private pool area, perfect for entertaining, relaxing, or enjoying the Florida lifestyle. Originally updated in 2012, the home benefits from a well-balanced and comfortable floorplan, complemented by key mechanical upgrades including a newer HVAC system and roof, and a brand-new water heater installed in 2024. With these major updates already completed, the property is truly move-in ready — offering peace of mind and lasting value. Don’t miss your opportunity to own a beautifully maintained home in a location that continues to deliver on both lifestyle and convenience. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High, the location also offers close proximity to top institutions and amenities, including Rollins College (2.3 miles), Full Sail University (2.4 miles), AdventHealth Winter Park (0.9 miles), and the VA Medical Center (1.3 miles). Outdoor enthusiasts will appreciate the nearby Cady Way Trail, Blue Jacket Park, and Lake Baldwin, all within a short drive, offering walking paths, open green space, and recreational opportunities. ASSUMABLE VA LOAN at 2.25% Interest Incredible opportunity to assume the seller’s VA mortgage at just 2.25% interest. Just minutes from the vibrant centers of Baldwin Park and Park Avenue, this property provides convenient access to an array of restaurants, boutique shops, cafés, and year-round events. 676 Dunblane Drive is a rare opportunity to own a well-located, move-in-ready home in one of Winter Park’s most established and sought-after neighborhoods. Book your private showing TODAY!
Listing is courtesy of: BALDWIN PARK REALTY LLC (407-986-9800)
Listing Agent: Emma Kaplan (407-942-7542)
2702 PARKLAND DR, WINTER PARK, FL 32789
$1,175,0003 Days on yellowkey MLS ID: O6397997
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2656 Built: 1949 Tax: $5,269 (2025)Community: ParklandoSingle Family
Taxes:$5,269
Remarks: Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.
Listing is courtesy of: NORDQUIST & COMPANY INC (407-694-0996)
Listing Agent: Elizabeth Nordquist (407-694-0996)
318 VITORIA AVE, WINTER PARK, FL 32789
$2,200,00017 Days on yellowkey MLS ID: O6388489
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2433 Built: 1922 Tax: $2,960 (2024)Community: College QuarterSpa: NoSingle Family
Taxes:$2,960
Remarks: Elegant 1922 Mission Revival home, located in popular College Quarter is a registered historic place in Winter Park, FL. Lifestyle is neighborly/relaxed/pet friendly/enhanced by proximity to Lake Virginia/lakeshore sidewalks/Rollins College campus/downtown Winter Park/Central Park/museums/shops/restaurants/cultural events, most walking distance. College Quarter residents enjoy exclusive use of Park/Dock on Lake Virginia to kayak/paddleboard/motor through Chain of Lakes or meet up for holiday fireworks/once-in-a-lifetime or yearly celestial events. College Quarter is one of the oldest/most architecturally diverse neighborhoods. This 1922 home represents the Florida Mission Revival vernacular through a timeless blend of stucco exterior walls/asymmetrical façade/prominent arches above doors/large windows/a flat roof/barrel red tiles/a distinctive parapet and walled courtyard with wrought-iron gate designed by local master ironworker. True to Mission Revival style, home connects to nature and surrounding College Quarter landscape through above architectural details that embody poetics of Mission Revival style. Builder used sensitive siting, placed home at highest elevation on street & it remains responsive to prevailing lake breezes/paths of rising sun & moon 104 years later. Lake light/sunlight/moonlight take centerstage in every room. Whether through window or door, each part of house has relationship with its surroundings. Mission Revival style accomplishes what homeowners often seek—a home’s ability to surprise. Airiness/lightness, beautiful atmosphere/ambience that Mission Revival architecture creates is notable that way. Mission Revival layout is key to that effect. Home’s modified Great Room layout combines roles of several traditional rooms--family/kitchen/living/dining rooms into 1 expansive space ideal for families/entertaining guests/enjoying natural light/views. Open layout in house is conducive to spending quality time together/socializing/entertaining. Proximity of kitchen/dining/living & outdoor spaces allow for easy interaction/conversation & creates sense of togetherness. Great Room dominates first floor living/dining room areas. One interior archway frames foyer, another leads to family room. Left of fireplace in Great Room are French Doors to enclosed porch/walled courtyard/plunge pool. Ceiling is 10 ft exposed rafters, 2 large, arched windows, one on East wall, one on West, face each other across 4 interior spaces. Changing light seen through handblown windowpanes in Great Room illuminate first floor & exterior environment. When moon rises over lake's cypress trees it appears in Great Room east window, travels thru sky, peeps into 2nd floor windows before moving ever higher in the sky. Kitchen’s center island is gleaming butcher block & divides food prep area from pantry/laundry/guest bathroom/living/dining areas. Kitchen counter imported tile/oak cabinets/small eat-in breakfast nook. French Doors open to brick courtyard/garden area/plunge pool. Kitchen/Pantry/Guest Bathroom have heart of pine floors. Laundry new ceramic tile, built-in wood cabinets/shelves, new washer/dryer, stainless-steel sink. Great Room floors original oak. Staircase/second story floors original heart of pine. Bedroom 1 ensuite Bathroom/Linen Closet/Balcony. Bedroom 2 beautiful views/2 closets/built-in drawers/. Bedroom 3 best water views during day. Single-family ownership 45 years. Roof & 2 balconies 5 yrs old. Major renovations 2021- to present
Listing Agent: Wendy Brandon (407-435-9009)
906 ENCLAVE PL, WINTER PARK, FL 32792
$1,925,00024 Days on yellowkey MLS ID: O6383092
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3618 Built: 2026Monthly Fee: $372 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
Taxes:$9,900
Tax Year: 2026
Remarks: Pre-Construction. To be built. This home is under construction proposed completion March 2027. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool. Spacious layouts, refined detailing, and quality construction create an elevated yet livable environment, all set within a beautifully landscaped and private setting. Please inquire for details and customization options.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Laura Earl (443-994-9441)
1760 GREENWICH AVE, WINTER PARK, FL 32789
$650,00025 Days on yellowkey MLS ID: O6392001
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1610 Built: 1967 Tax: $2,779 (2025)Community: Golfview HeightsSingle Family
Taxes:$2,779
Remarks: Fabulous Winter Park location. This is a 3 bedroom, 2 bath patio home with a great layout, split bedroom plan, high ceilings in the living room, and an eat in kitchen that is open to the family room. A large primary bedroom which has a walk in closet, two additional closets and french doors leading out to the back yard. There is a screened in patio off of the breakfast / dining area and an interior laundry room. Zoned for Winter Park schools, minutes from downtown Park Ave., Rollins College and Advent Health Winter Park. Property is a gem perfect for a renovation or an opportunity to build new.
Listing Agent: Meg Dolan (321-948-0701)
1870 WALKER AVE, WINTER PARK, FL 32789
$1,425,00031 Days on yellowkey MLS ID: O6390504
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2046 Built: 2026 Tax: $3,981 (2025)Community: Osceola HeightsSingle Family
Taxes:$3,981
Remarks: This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas, setting a warm and elegant tone. The open-concept floor plan is designed for everyday living and effortless entertaining, with expansive windows allowing natural sunlight to pour into every space. At the heart of the home is a beautifully designed kitchen that blends classic style with modern functionality. A stunning quartz waterfall island anchors the space, complemented by custom cabinetry and a suite of high-end appliances including an ILVE induction range with six elements and Café French door refrigerator, dishwasher and microwave. Designer-grade lighting and refined finishes elevate the kitchen into a centerpiece of the home. The dining room is filled with light and character, featuring three sets of French doors that open to a charming private front and side courtyard, an ideal setting for morning coffee or intimate outdoor dining. In the living room, a dramatic wall of sliding glass doors connects the interior to the brick patio and backyard, creating a seamless indoor-outdoor lifestyle. The first-floor primary suite offers a peaceful retreat, complete with a spacious walk-in closet and a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub and dual vanities. Additional conveniences on the main level include a beautifully appointed powder bath, a dedicated laundry room and a generous storage room tucked neatly beneath the staircase. Upstairs, a versatile loft provides additional living space ideal for a media area, office or lounge. Two additional bedrooms are also on the second floor, each featuring custom built-in closets, beautiful designer lighting and abundant natural light. Built with quality and efficiency in mind, the home includes numerous upgrades such as a slate roof, Trane air-conditioning system, Rheem tankless water heater and a two-car attached garage. Ideally just minutes from the renowned shopping and dining of Park Avenue and charm of downtown Winter Park, this exceptional home also offers convenient access to major roadways, Orlando International Airport, leading hospitals, and top-rated public and private schools, bringing together style, comfort and location in one remarkable new construction opportunity.
Listing Agent: Mick Night (407-629-4446)
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