Location: Winter Park, Winter Park
Do Not Show Listings
2889 ROUEN AVE, WINTER PARK, FL 32789
$399,5004 Days on yellowkey MLS ID: L4961275
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1959 Tax: $5,061 (2025)Community: Winter Park ManorSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,061
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Charming Winter Park home on a spacious quarter-acre lot! Welcome to 2889 Rouen Avenue, Charming Winter Park home on a spacious quarter-acre lot! Welcome to 2889 Rouen Avenue, Fresh exterior paint and move-in-ready 3-bedroom, 2-bath residence offering approximately 1,140 square feet of comfortable living space. This home features a bright and functional layout, well-sized bedrooms, and a large fenced yard with plenty of room to enjoy the outdoors. Brand new Roof is underway. Conveniently located near Rollins College, Park Avenue, Full Sail University, shopping, dining, and I-4, and zoned for Dommerich, this property offers an outstanding opportunity in a sought-after location. Move-in-ready 3-bedroom, 2-bath residence offering approximately 1,140 square feet of comfortable living space. This home features a bright and functional layout, well-sized bedrooms, and a large fenced yard with plenty of room to enjoy the outdoors. Brand new Roof is underway. Conveniently located near Rollins College, Park Avenue, Full Sail University, shopping, dining, and I-4, and zoned for Dommerich, this property offers an outstanding opportunity in a sought-after location. see private remarks and showing time for direct seller’s contact.
Listing is courtesy of: HELLOSOLD LLC (954-778-5300)
Listing Agent: Dan Farber (954-778-5300)
2408 LAFAYETTE AVE, WINTER PARK, FL 32789
$1,495,00015 Days on yellowkey MLS ID: O6397694
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2838 Built: 2024 Tax: $3,770 (2024)Community: Winter Park VillageSpa: NoSingle Family
Taxes:$3,770
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2024
Middle School: Maitland Middle
Remarks: This custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set apart for quiet pursuits. The chef’s kitchen opens naturally to the great room and boasts a large island, top-of-the-line Thermador appliances, complemented by the sleek quartz countertops that offer both style and functionality. Conveniently equipped with two sets of washers and dryers, this home ensures efficiency and ease for the busiest of households. Retreat to the master suite, where luxury meets serenity. A massive walk-in closet provides ample storage, while the spa-like master bath invites relaxation with its elegant design and premium features. The indoor outdoor flow is easy with the huge set of glass sliders leading to the covered porch equipped with drop down screens. Enjoy the summer kitchen and sparkling pool while entertaining family and friends. This home is a true gem that combines thoughtful details with sophisticated style.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Matthew Burks (407-257-5347)
2412 CHANTILLY AVE, WINTER PARK, FL 32789
$2,394,50073 Days on yellowkey MLS ID: O6381552
REDUCED by $500 (0.0%) on 04/20/2026
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 4506 Built: 2026 Tax: $4,779 (2025)Community: Winter Park VillageSingle Family
Taxes:$4,779
Remarks: Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This flows effortlessly into a gorgeous gourmet kitchen with high-end appliances featuring a Wolf range, Sub-Zero refrigerator, Euro-style cabinetry, oversized island, and walk-in pantry. The downstairs primary suite overlooks the pool and includes a spa-like bath with soaking tub and rain showers. An additional ensuite bedroom on the first floor works perfectly as a guest room or office. Upstairs you’ll find a large loft and media area with private balcony, along with three ensuite bedrooms including walk-in closets. Step outside and enjoy year-round living under the covered lanai featuring a summer kitchen overlooking the saltwater pool surrounded by mature landscaping. An outdoor bath adds extra convenience, and the oversized lot provides abundant space to relax, entertain or dine al fresco. This home comes complete with a spacious three-car garage with EV charging. Minutes to Interlachen Country Club, Winter Park Racquet Club, and Park Ave shopping. Don’t miss this beautiful custom modern home in one of Winter Park’s most sought-after neighborhoods! Ask about the new landscaping package, and driveway installation.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Tab Bish Llc (855-450-0442)
350 CORNWALL RD, WINTER PARK, FL 32792
$775,00027 Days on yellowkey MLS ID: O6394524
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2038 Built: 1963 Tax: $2,127 (2025)Community: Winter Park Pines RepSingle Family
Taxes:$2,127
Remarks: One or more photo(s) has been virtually staged. Fully reimagined and COMPLETELY RENOVATED with Custom features, this stunning 4-br, 3-ba home in desirable Winter Park Pines sits proudly on a spacious corner lot and offers Modern Luxury with thoughtful, HIGH END UPGRADES throughout. The interior showcases all-new cabinetry and countertops, highlighted by a dramatic waterfall kitchen island, brand-new appliances including a built-in microwave tucked into a custom pantry cabinet. Every detail has been carefully considered, from new luxury vinyl flooring and interior doors to upgraded closet shelving, sleek bathroom mirrors, and stylish shower enclosures. Sound insulation enhancements in key areas—including the primary suite, bathrooms, and kitchen walls—provide added comfort and privacy, while smart ceiling fans, dimmable lighting, USB charging outlets, and pre-wiring for under-cabinet lighting and wall-mounted TVs bring modern convenience to everyday living. Beyond the interior, the home continues to impress with major system upgrades and durable exterior improvements designed for long-term peace of mind. Enjoy a BRAND NEW ROOF with transferable warranty, updated soffit and fascia, rot-proof siding and porch columns, and new fiberglass exterior doors with built-in blinds. The property also features a new irrigation system, vinyl fencing, and an expansive 3+ car driveway. Behind the walls, everything has been upgraded—including full electrical rewiring with a new 200-amp service, all-new plumbing from underground lines to fixtures, and a high-efficiency HVAC system with new ductwork and insulation for maximum energy savings, making this home truly MOVE-IN READY with no detail overlooked. FYI-Dumpster to be removed and pressure washed and Install of PVC fence w/ gate at driveway on 04/09.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Kelly Butterfield (407-463-1289)
3651 N GOLDENROD RD #D101, WINTER PARK, FL 32792
$179,00038 Days on yellowkey MLS ID: O6391256
REDUCED by $6,000 (3.2%) on 04/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 840 Built: 1990Monthly Fee: $370 Tax: $2,000 (2025)Community: Lancelot/Winter ParkCondo
Taxes:$2,000
Elementary School: Aloma Elem
Middle School: Glenridge Middle
Remarks: Welcome to this beautifully maintained 2-bedroom, 2-bathroom first-floor corner-unit condo in Winter Park, offering comfort, convenience, and peace of mind, with major updates completed in 2026. These upgrades were specifically implemented to enhance the property's aesthetic appeal and energy efficiency. The exterior updates include replacing all windows with single-hung, double-pane, low-E glass vinyl units and installing a matching vinyl sliding patio door. Interior improvements include new interior and closet doors, 5" baseboards, and fresh paint on all ceilings, walls, and trim. Additionally, all ceilings have been modernized to a smooth finish, and 2" cordless faux-wood blinds have been installed throughout. Both bathrooms have been fully renovated with new flooring, wall tiling, tubs, toilets, vanities, and updated fixtures. The kitchen has also been completely transformed with new cabinetry, granite countertops, a modern faucet, and a full suite of stainless steel appliances. Located near the University of Central Florida, Full Sail University, and SR-417, this condo offers quick access to major commuting routes, shopping, dining, and everyday essentials. Whether you're looking for a primary residence or a long-term investment opportunity, this property combines location, functionality, and value in one of Orlando's most connected areas.
Listing is courtesy of: ANNE ROGERS REALTY GROUP INC (407-649-4141)
Listing Agent: Reza Shirzad (407-234-1515)
291 LEWFIELD CIR #291, WINTER PARK, FL 32792
$144,00068 Days on yellowkey MLS ID: O6382547
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973Monthly Fee: $350 Tax: $1,942 (2025)Community: Stratford Winter ParkCondo
Taxes:$1,942
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: One of the best patio views in this community. Enjoy easy living in this cozy, open-concept first-floor condo located in a desirable Winter Park community. Step out onto your newly screened-in patio and take in the peaceful, park-like setting — a relaxing extension of your living space and the perfect spot for morning coffee or evening unwinding. Recent 2025 improvements include a new A/C system, water heater, freshly painted interior, new screened porch, and new toilet — giving you move-in-ready comfort and peace of mind. The kitchen comes fully equipped with range, dishwasher, refrigerator, and microwave. A stackable washer and dryer are conveniently located in the bedroom, and an additional community laundry room with two washers and dryers is available free of charge. Stratford residents enjoy an amenity-rich lifestyle including: • Two sparkling pools • Tennis courts • 24/7 fitness center • Clubhouse available for private gatherings • Pet station *Planned social events for residents. The HOA adds tremendous value by covering water, trash removal, internet, pest control, exterior maintenance, grounds care, and common areas — simplifying ownership and monthly budgeting. Located in a prime Winter Park area with easy access to 408, Semoran Blvd., 417, I-4, and State Road 50. Just minutes from shopping, dining, grocery stores, and within 20 minutes of UCF, Full Sail University, Rollins College, and Park Avenue. With its thoughtful updates, first-floor convenience, and exceptional community amenities, this condo offers more than just a home — it delivers an above-average lifestyle in one of Central Florida’s most desirable locations.
Listing is courtesy of: WATSON REALTY CORP (407-332-6000)
Listing Agent: Barbara Coy (407-497-1777)
1319 BESSMOR RD, WINTER PARK, FL 32789
$595,0004 Days on yellowkey MLS ID: O6400395
1 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1126 Built: 1956 Tax: $5,626 (2025)Community: Winter Park VillageSpa: NoSingle Family
Taxes:$5,626
Elementary School: Dream Lake Elem
Remarks: Under contract-accepting backup offers. Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024. SEPTIC PUMP OUT, OCT 2025. No carpeting instead there is SOLID FLOORING THROUGHOUT: WOOD PARQUET, TILE, LUXURY VINYL PLANK. The kitchen has been updated with SOLID WOOD KITCHEN CABINETS + GRANITE COUNTER TOPS and newer MATCHING APPLIANCES. The home has INDOOR WASHER/DRYER and a working fireplace. The back yard is FULLY FENCED. Local top rated CITY OF WINTER PARK SCHOOLS. And CITY OF WINTER PARK UTILITIES. The land, the lot have a fantastic upside. BOTH NEXT DOOR (WEST SIDE) AND REAR (NORTH SIDE) NEIGHBORING LOTS HAVE BEEN EMPTY FOR SEVERAL YEARS. This is a great investment and the property itself offers excellent rental income. Think "down the road" value + immediate return value.
Listing is courtesy of: GALLOWAY REAL ESTATE (407-421-9990)
Listing Agent: Sidney Galloway (407-421-9990)
101 S NEW YORK AVE #302, WINTER PARK, FL 32789
$1,450,00031 Days on yellowkey MLS ID: O6390752
REDUCED by $130,000 (8.2%) on 04/24/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3174 Built: 2009Monthly Fee: $1,263 Tax: $19,802 (2025)Community: Winter Park ResidentialCondo
Taxes:$19,802
Remarks: Motivated Sellers! Discover unparalleled luxury at The Douglas Grand, a distinguished location just a stone’s throw from Park Ave in Downtown Winter Park. This expansive 2-Story unit boasts 3,174 sq/ft of living space with your private elevator. From the moment you step inside, you’ll be captivated by the exquisite craftmanship and modern comforts that define this exceptional residence. This stunning condo boast three spacious ensuite bedrooms and abundance of storage. The heart of this home is the gourmet kitchen, custom-designed and built to fulfill every chef's dream complemented by top-of-the-line appliances that include a wall-mounted convection/microwave oven and a cutting-edge Wolfe induction stove top. The kitchen is not only functional but also perfect for entertaining, featuring a spacious breakfast bar where culinary creativity knows no bounds. As you move through this exceptional residence, in the living room, dining room, and entrance, creating an inviting ambiance that welcomes you home. Indulge in the spa-like sanctuary of the master bathroom, where luxury knows no bounds with a charming fireplace in the primary suite. Here, you'll find a sumptuous bathtub, separate vanity areas. With three generously appointed bedrooms, featuring custom closets, you'll have ample space to organize your wardrobe and storage needs effortlessly. Step onto the private balcony upstairs and be captivated by the breathtaking views. This secluded outdoor space is an ideal setting for unwinding with an evening cocktail, savoring a family dinner, or starting your day with a tranquil cup of morning coffee. The Douglas Grand enjoys a central location that places you within a lifestyle that defines this charming community. In addition to its unmatched location, this building offers a quiet, private, and secure environment—making it the perfect choice for those seeking a "lock and leave" second home or a luxurious vacation retreat. Don't miss this opportunity to experience the height of elegance and y reach of Downtown Winter Park's award-winning restaurants, cultural museums, upscale shopping boutiques, and the vibrant sophistication. Contact me today to schedule a private viewing of this remarkable residence.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Julie Scott (407-497-3492)
1695 LEE RD #C202, WINTER PARK, FL 32789
$205,000417 Days on yellowkey MLS ID: O6285607
REDUCED by $5,000 (2.4%) on 04/23/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1149 Built: 1966 Tax: $2,126 (2024)Community: Waterfall Cove At Winter ParkCondo
Taxes:$2,126
Remarks: This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.
Listing is courtesy of: PRIMESTATE REALTY, INC. (407-850-9494)
Listing Agent: Hoover Yap (407-342-9395)
736 WARRENTON RD, WINTER PARK, FL 32792
$300,00017 Days on yellowkey MLS ID: O6397291
1 Days Off yellowkey (back on 4/14/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1320 Built: 1986Monthly Fee: $86 Tax: $4,378 (2025)Community: Winter Park Pines Patio HomesSpa: NoHalf Duplex
Taxes:$4,378
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Renovated 2 bedroom, 2 bathroom villa in a prime Winter Park location, ready for its next owner. Walk into a spacious, light and bright foyer with fresh interior paint and sliding doors that lead out to the patio, bringing in tons of natural light. The seller has removed all popcorn ceilings (a huge upgrade), and the property features laminate flooring throughout most of the main living areas. The main living space has vaulted ceilings and an open layout with room for both living and dining, and sliding glass doors leading out to the patio. The kitchen has been updated with new stainless steel appliances and new countertops, and offers a closet pantry along with a bay window that brightens the space. The primary suite is set toward the back of the home with high ceilings, its own sliding doors to the patio, a walk-in closet, and a renovated bathroom with a large walk-in shower. The split floor plan places the second bedroom near the front by the foyer, with a renovated full bathroom just next to it—great for guests or a home office. The backyard offers a blank canvas to create your own oasis, with a covered patio, a large screened porch, and a fully fenced private yard—hard to find with a villa! Additional highlights include a one-car garage with washer/dryer hookup, new light fixtures, and fresh interior paint. Located in the Winter Park Pines just minutes from iconic Park Avenue shopping and dining and downtown Winter Park. Across from Full Sail and a short drive to UCF. Call today to schedule your private showing!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Andrea Parra Chopite, Pa (407-515-0097)
665 LYMAN AVE, WINTER PARK, FL 32789
$450,0008 Days on yellowkey MLS ID: O6400200
0 Days Off yellowkey (back on 4/23/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1119 Built: 1994 Tax: $5,851 (2025)Community: Town Of Winter ParkSingle Family
Taxes:$5,851
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated Winter Park bungalow, just steps from Hannibal Square and Park Avenue! This charming 3-bedroom, 2-bath home offers just over 1,100 square feet of thoughtfully renovated living space. The kitchen has been tastefully renovated and upgraded with modern appliances, while tile flooring runs throughout the entire home. Major updates include newer roof, fully replumbed system (completed this month), and a brand-new water heater—giving you true peace of mind. Inside, you’ll love the high ceilings in the living, dining, and kitchen areas, creating a bright and open feel. Large windows flood the home with natural Florida sunlight, and the private rear deck is perfect for relaxing or entertaining. This is a true move-in-ready home in one of Winter Park’s most desirable locations—schedule your showing today before it’s gone!
Listing is courtesy of: CENTRAL FLORIDA PRIME REAL ESTATE LLC (407-404-4041)
Listing Agent: Jonathan Nakhnoukh (407-334-5806)
3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792
$159,0004 Days on yellowkey MLS ID: O6401114
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 840 Built: 1990Monthly Fee: $370 Tax: $2,461 (2025)Community: Lancelot/Winter ParkCondo
Taxes:$2,461
Remarks: One or more photo(s) has been virtually staged. Welcome to this inviting 2-bedroom, 2-bathroom condo located in the desirable Lancelot at Winter Park community, offering the perfect blend of comfort and convenience for investors, first-time buyers, or anyone seeking low-maintenance living. This well-appointed unit features an open and airy layout with abundant natural light, seamlessly connecting the living and dining areas to create an ideal space for both relaxing and entertaining. The modern kitchen provides a functional workspace designed for everyday ease. Residents will also enjoy access to a community pool, perfect for unwinding or hosting guests, along with professionally maintained common areas that enhance the overall appeal of the neighborhood. Ideally situated, this condo offers close proximity to UCF and Full Sail University, making it an excellent option for rental potential, as well as convenient access to major shopping centers, dining options, and key highways including I-4 for easy commuting. Whether you're searching for a primary residence, a second home, or a strong investment opportunity, this property delivers exceptional value in a prime location. The property was previously leased at $1,625 per month.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Christina Munkberg Bianca (407-340-1308)
225 LEWFIELD CIR #225, WINTER PARK, FL 32792
$220,000326 Days on yellowkey MLS ID: O6314817
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 953 Built: 1973Monthly Fee: $465 Tax: $1,020 (2024)Community: Stratford A Winter Park CondoCondo
Taxes:$1,020
Remarks: One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors leading to the community green space that is a tropical oasis. The adjacent dining area includes a stackable washer/dryer and flows into a modern kitchen with floor-to-ceiling cabinetry, granite countertops, and stainless steel appliances. Both spacious bedrooms sit near the entry, with the primary suite offering a walk-in closet and a sleek ensuite bath with a glass-front shower and floating vanity—mirrored in the newly updated guest bath as well. Enjoy low-maintenance living with access to resort-style community amenities including two pools, tennis courts, and a gym—all in a prime location! Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
144 LEWFIELD CIR #144, WINTER PARK, FL 32792
$137,00044 Days on yellowkey MLS ID: O6390043
REDUCED by $7,000 (4.9%) on 04/21/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973Monthly Fee: $351 Tax: $720 (2024)Community: Stratford A Winter Park CondoCondo
Taxes:$720
Remarks: LOCATION! LOCATION! LOCATION! Beautiful 2nd floor corner condo in desirable Winter Park, featuring 1 bed/1 bath, open concept living/dining area and balcony. Move-in ready and conveniently located near UCF, Rollins College, Valencia College, Park Avenue, and Downtown Orlando. Residents enjoy resort-style amenities including two pools, tennis court, a fitness center, and clubhouse available for rental for gathering or events. The unit includes a fully equipped kitchen, stackable washer and dryer in the bedroom, and access to free community laundry. HOA covers water, trash removal, internet, pest control, exterior maintenance, and grounds care. Close to shopping, dining, and major highways for easy access across the area.
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Sandra Da Silva (407-840-8500)
2708 LION HEART RD, WINTER PARK, FL 32792
$627,50052 Days on yellowkey MLS ID: O6387685
REDUCED by $2,000 (0.3%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1785 Built: 1963 Tax: $7,007 (2024)Community: Winter Park Pines RepSpa: NoSingle Family
Taxes:$7,007
Elementary School: Brookshire Elem
Remarks: Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.
Listing is courtesy of: EQUITYPRO LLC (407-203-6860)
Listing Agent: Navid Rokh (321-900-5977)
2681 FITZHUGH RD, WINTER PARK, FL 32792
$750,00065 Days on yellowkey MLS ID: O6383699
0 Days Off yellowkey (back on 4/20/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2375 Built: 1966 Tax: $5,903 (2024)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$5,903
Remarks: Under contract-accepting backup offers. CALLING FOR HIGHEST AND BEST OFFERS BY MONDAY, APRIL 20th at 9:00 AM. Tucked away on a quiet street in the heart of Winter Park, this fully renovated 4-bedroom, 2.5-bath pool home—enhanced by fully owned solar panels—offers a rare blend of privacy, thoughtful design, and effortless indoor-outdoor living. Set on a generous ¼-acre lot, every detail has been curated to create a home that feels both elevated and family-friendly. Inside, the home opens to a flowing layout ideal for both everyday living and entertaining. Wide-plank luxury vinyl flooring, designer tile, and a soothing, modern palette create a cohesive sense of calm throughout. The kitchen is both a statement and a gathering place, featuring an oversized island wrapped in Taj Mahal quartzite, stainless steel appliances, and a custom wine bar—designed for connection, conversation, and celebration. Adjacent to the kitchen, the sunroom is a showstopper bathed in natural light and enhanced with custom built-ins, this versatile space effortlessly transforms into a home office, playroom, or entertainment lounge. This is where this home comes alive; perfect for large gatherings. The primary suite offers a serene retreat, highlighted by a fully remodeled spa-inspired bathroom with a soaking tub and a sleek, modern shower; inviting you to slow down and unwind. Outside, the newly added 800-square-foot turf play area, side yard, and green space surrounding the pool create room to play, entertain, and relax. The cul de sac and backyard feel exceptionally private, quiet, and peaceful. Just minutes from Park Avenue, you are surrounded by boutique shopping, acclaimed dining, lakeside strolls, and a lifestyle that feels both vibrant and relaxed. From morning coffee runs to evening walks under oak-lined streets, this is the essence of Winter Park living. This home is more than move-in ready—it’s a place to gather, grow and live. ROOF (OCT. 2022) HVAC (2017) WATER HEATER (2016) PLUMBING (2020) ELECTRICAL (UPDATED 2026) POOL PUMP/MOTOR (2020), POOL RESURFACED (2017) DRAIN SYSTEM: FRENCH DRAINS, SUMP PUMPS, GUTTERS (2024)
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Rebecca Bininger Junod (407-230-3650)
731 BONGART RD, WINTER PARK, FL 32792
$499,999113 Days on yellowkey MLS ID: S5140952
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1826 Built: 1961 Tax: $5,910 (2025)Community: Winter Park EstatesSingle Family
Taxes:$5,910
Elementary School: Lakemont Elem
Remarks: One or more photo(s) has been virtually staged. Experience luxury living in this stunning, fully remodeled single-family home located in the heart of Winter Park, where modern sophistication meets exceptional functionality. This spectacular residence features a total of 4 spacious bedrooms and 3 modern bathrooms, boasting sleek laminate flooring throughout and a chef-inspired kitchen fully equipped with premium stainless steel appliances. A standout feature of this property is its versatile layout: one bedroom and one bathroom are completely separate from the main living area, offering the perfect solution for guest privacy, a multi-generational suite, or an opportunity to generate additional rental income. Outside, the massive backyard and sparkling pool provide an ideal setting for family gatherings and outdoor entertainment, all while being nestled in a prime location just minutes from the iconic Park Avenue shopping district, the Winter Park Farmer’s Market, and convenient access to the 436. This home is the ultimate choice for those seeking the perfect blend of suburban tranquility and urban convenience in the very best of Central Florida living.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Maria Gomez Arevalo, Pa (407-705-7203)
639 FRIAR RD, WINTER PARK, FL 32792
$795,00023 Days on yellowkey MLS ID: O6395715
1 Days Off yellowkey (back on 4/20/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1950 Built: 1967 Tax: $3,415 (2025)Community: Winter Park PinesSingle Family
Taxes:$3,415
Remarks: Welcome to 639 Friar Road, ideally situated on a quiet street in the highly desirable Winter Park Pines neighborhood. This extensively updated residence offers the character of a classic 1960s home with the quality and feel of a 2026 renovation. Major improvements include a new roof, new HVAC system with new ductwork, new panel box, and thoughtfully curated high-end kitchen, bath, and lighting design elements. Original terrazzo flooring has been meticulously restored and polished throughout, preserving the home’s timeless appeal. Featuring four bedrooms, three full baths, the home offers a functional open-concept layout with a desirable split floor plan. Two primary suites, each with private en-suite baths, provide flexibility for multi-generational living or guest accommodations. The property showcases strong curb appeal and continues to impress outdoors with a spacious backyard and an oversized lanai designed for entertaining. Zoned for highly rated Winter Park schools, this home delivers an exceptional blend of style, comfort, and indoor-outdoor living in one of Winter Park’s most established neighborhoods.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Dianne Moore (407-494-7575)
188 LEWFIELD CIR #188, WINTER PARK, FL 32792
$129,99053 Days on yellowkey MLS ID: O6387291
REDUCED by $9,010 (6.5%) on 04/20/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973 Tax: $424 (2024)Community: Stratford A Winter Park CondoCondo
Taxes:$424
Remarks: Welcome to 188 Lewfield Cir — a beautifully designed 1-bedroom, 1-bath condo located in the highly desirable The Stratford at Winter Park Condominium community. This unit features an open floor plan that creates a bright, spacious feel, perfect for comfortable everyday living or entertaining guests. The layout maximizes functionality while maintaining a modern, low-maintenance lifestyle. Residents of The Stratford enjoy resort-style amenities including two outdoor swimming pools, a clubhouse, a fully equipped fitness center, and beautifully maintained grounds; offering both relaxation and convenience right outside your door. Located in the heart of Winter Park, you’re just minutes from premier shopping, top-rated restaurants, entertainment, and major roadways. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this location places you in one of Central Florida’s most sought-after areas. Comfort. Convenience. Winter Park lifestyle. 188 Lewfield Cir is ready to welcome you home.
Listing Agent: Johnny Aybar, Llc (407-808-9569)
744 CORNWALL RD, WINTER PARK, FL 32792
$695,000267 Days on yellowkey MLS ID: O6332168
REDUCED by $20,000 (2.8%) on 04/15/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1968 Built: 1968 Tax: $5,359 (2024)Community: Winter Park PinesSpa: NoSingle Family
Taxes:$5,359
Remarks: Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing pool, pickleball courts, and miles of trails for jogging, biking, or leisurely strolls. Enjoy the outdoors while being in close proximity to shopping, dining, and the celebrated Winter Park schools.Recent updates make this home truly special. The new A/C system and upgraded electrical panel—complete with room for additional breakers—ensure your comfort and convenience. The manifold system has also been updated, and the roof was newly installed in 2018 for peace of mind.Additionally, half of the windows have been replaced with high-quality Anderson windows, enhancing both energy efficiency and natural light.Don’t miss the opportunity to own this well-maintained home in a vibrant neighborhood that perfectly balances recreation and relaxation. Schedule your showing today!
Listing is courtesy of: VERSALIS REALTY POWERED BY SELLSTATE (407-608-9593)
Listing Agent: Tammy Cuddy (407-608-9593)
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