Location: Winter Park
Do Not Show Listings
423 OLOLU DR, WINTER PARK, FL 32789
$589,000104 Days on yellowkey MLS ID: O6369976
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1920 Built: 1981 Tax: $4,030 (2024)Community: Killarney CircleSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,030
Elementary School: Killarney Elem
High School: Edgewater High
Tax Year: 2024
Middle School: College Park Middle
Remarks: Welcome to this beautifully remodeled two story home in one of Winter Park’s most desirable upscale neighborhoods, offering timeless charm, modern upgrades, and no HOA restrictions. Completely renovated in 2019, this property features a newer roof, windows, A/C system, electrical, plumbing, driveway, and a fully fenced yard with a private entry gate, along with fresh exterior & interior repaint completed in 2025. Inside, you will find bright, open living spaces and a modern kitchen designed for both everyday living and entertaining. Upstairs, a spacious family room opens to a covered balcony with serene lake views, creating an ideal space to relax or entertain. The flexible layout also allows for two separate living areas, making it well suited for multi-generational living or rental income. Step outside to enjoy the expansive gated yard with plenty of room for gatherings along with ample parking. Conveniently located just minutes from shopping, dining, Downtown Orlando, Downtown Winter Park, Full Sail University, and Rollins College, this home offers an exceptional location. The seller is offering 1% closing cost Buyer credit with a full price offer. Do not miss this rare opportunity to own a beautifully updated home with endless potential in a highly desirable location. Contact us today to schedule your private showing!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jill Healey (407-797-1420)
901 ENCLAVE PL, WINTER PARK, FL 32792
$1,495,00033 Days on yellowkey MLS ID: O6383602
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2738 Built: 2026Monthly Fee: $247 Tax: $9,900 (2026)Community: The Enclave Winter ParkTownhouse
Taxes:$9,900
Elementary School: Lakemont Elem
High School: Winter Park High
Tax Year: 2026
Middle School: Maitland Middle
Remarks: Pre-Construction. To be built. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, blending timeless character with modern luxury. 901 Enclave Place (Lot1) is a thoughtfully designed courtyard home offering an elegant yet functional layout centered around private outdoor living. A charming covered front porch and welcoming foyer lead into an expansive open-concept gathering and dining space, seamlessly connected to a designer kitchen featuring a large center island, walk-in pantry, and effortless flow for entertaining. At the heart of the home, a covered lanai and courtyard create a true indoor-outdoor lifestyle—perfect for year-round enjoyment and intimate gatherings. The first-floor primary suite is a private retreat with a spacious walk-in closet and spa-inspired bath, complemented by a convenient powder bath and laundry/pantry area. Upstairs, you’ll find a well-appointed layout including an second primary suite with a luxurious bath and oversized closet, a additional bedroom, full bath, and a versatile gathering loft—ideal as a media room, office, or flex space. Designed with both comfort and sophistication in mind, this residence showcases clean architectural lines, abundant natural light, and carefully curated indoor and outdoor living spaces. Located within a boutique enclave of just a limited number of homes, residents will enjoy a serene setting surrounded by mature trees and thoughtfully designed community green space. Experience the best of Winter Park living with close proximity to renowned dining, shopping, and top-rated schools—all within one of the area’s most sought-after new communities. Design book is available upon request. Please inquire for details and customization options.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Laura Earl (443-994-9441)
905 ENCLAVE PL, WINTER PARK, FL 32792
$1,495,00033 Days on yellowkey MLS ID: O6383679
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2756 Built: 2026Monthly Fee: $247 Tax: $9,900 (2026)Community: The Enclave Winter ParkTownhouse
Remarks: Pre-Construction. To be built. 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. Ideally located within walking distance to Park Avenue and historic Old Winter Park, this exclusive neighborhood blends timeless character with modern luxury. The courtyard homes at The Enclave offer a distinctive design centered around light, openness, and indoor-outdoor living. These four-bedroom residences feature thoughtfully designed floor plans with a first-floor primary suite and expansive living spaces that flow seamlessly to private outdoor areas. Large windows and two unique entry design options allow for abundant natural light, enhancing the open-concept layouts. Each home is finished with high-end selections, including Wolf and Sub-Zero appliances, high-performance double-pane windows, and elevated interior finishes throughout. Blending modern design with comfort and functionality, these homes provide a unique opportunity to enjoy a private courtyard lifestyle in one of Winter Park’s most desirable locations. Design book is available upon request. Please inquire for details and customization options.
Listing Agent: Matthew Burks (407-257-5347)
1695 LEE RD #E204, WINTER PARK, FL 32789
$115,000133 Days on yellowkey MLS ID: O6366205
REDUCED by $9,900 (7.9%) on 04/03/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 881 Built: 1966Monthly Fee: $482 Tax: $1,917 (2024)Community: Waterfall CoveCondo
Taxes:$1,917
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom. Durable vinyl flooring with cozy carpeted bedrooms with a spacious walk in in closet in the primary bedroom. You will get a private balcony — perfect for morning coffee or evening relaxation and the convenience of your our laundry with washer and dryer hookups included. This condo is perfectly located in a desirable area with lots of nearby shopping, restaurants, and amenities
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Brandy Ray (949-449-5652)
4190 BEAR GULLY RD, WINTER PARK, FL 32792
$524,900106 Days on yellowkey MLS ID: O6371014
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2058 Built: 2003Monthly Fee: $52 Tax: $5,630 (2024)Community: Bear Gully ForestSingle Family
Taxes:$5,630
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Spacious Winter Park home on over a half acre with no rear neighbors!. In Bear Gully Forest community and has over 2,000 s/f- with a Living Room, Dining Room, Eat-in Kitchen and more. The home's fully-equipped kitchen has excellent cabinet space and appliances that include a stove, microwave, and dishwasher. An inside laundry room has a washer/dryer combination for your convenience. Bedroom with 1/2 bath upstairs. Roof new in 2018 with a 10 year full warranty.
Listing is courtesy of: ADVANCE REALTY & MANAGEMENT LLC (407-901-3636)
Listing Agent: Craig Swetnam (407-802-0405)
5180 LAZY OAKS DR #5180, WINTER PARK, FL 32792
$290,00021 Days on yellowkey MLS ID: O6395367
0 Days Off yellowkey (back on 4/8/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1008 Built: 1984Monthly Fee: $277 Tax: $1,746 (2024)Community: Lazy Oaks CondoCondo
Taxes:$1,746
Remarks: Welcome to your Florida retreat. Whether you’re searching for the perfect first home or looking to downsize into a low-maintenance lifestyle, this single-story end-unit villa offers the ideal blend of comfort, convenience, and charm. With only one shared wall, it lives and feels like a single-family home. The HOA handles all exterior maintenance—including the roof, which was replaced just a few years ago—keeping your upkeep minimal and your insurance costs impressively low. The seller has lovingly maintained this home for nearly a decade and completed a long list of high-quality updates, including: - Glass sliders replaced in 2018 - Water heater replaced in 2019 - AC replaced in 2024 - Garage door replaced in 2024 - Front entry storm door added in 2024 - All kitchen appliances replaced within the last 5 years If that’s not pride of ownership, what is? Inside, the kitchen features newer cabinets, quartz countertops, and updated lighting throughout the home. The seller also transformed the back patio into a screened-in oasis—your own private Florida getaway perfect for morning coffee or evening relaxation. Location is another major highlight. Situated in prestigious Winter Park and zoned for some of Seminole County’s top-rated schools, this home offers unbeatable convenience. You’re just minutes from major highways, shopping, dining, and everything Central Florida has to offer. Schedule your showing today and experience all the beautiful features this home provides.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Farzana Zalil (407-617-3258)
4768 TANGERINE AVE #4768, WINTER PARK, FL 32792
$185,00057 Days on yellowkey MLS ID: S5144503
REDUCED by $9,900 (5.1%) on 04/08/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1973Monthly Fee: $280 Tax: $1,479 (2024)Community: Wrenwood CondoCondo
Taxes:$1,479
Remarks: Stunning renovated 1-bedroom in Winter Park! Enjoy all-new flooring, fresh paint, knockdown ceilings, and a sleek bath and kitchen with new cabinets and stainless appliances. Community was freshly painted and roads repaved in 2025. Prime location near top dining, shopping, and parks. Move-in ready perfection!
Listing is courtesy of: PROPERTY OUTLET INTERNATIONAL (407-723-7000)
Listing Agent: Christopher Franqui (347-703-7008)
550 PALMER AVE, WINTER PARK, FL 32789
$6,895,000182 Days on yellowkey MLS ID: O6349188
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 5939 Built: 2025 Tax: $10,292 (2025)Community: Osceola PlaceSpa: YesSingle Family
Taxes:$10,292
Tax Year: 2025
Remarks: Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: John Mcdade (407-721-7275)
914 ENCLAVE PL, WINTER PARK, FL 32792
$1,895,00033 Days on yellowkey MLS ID: O6391825
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3617 Built: 2026Monthly Fee: $372 Tax: $10,000 (2025)Community: The Enclave Winter ParkSingle Family
Taxes:$10,000
Remarks: Pre-Construction. To be built. 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 a elevated yet livable environment, all set within a beautifully landscaped and private setting. Please inquire for details and customization options.
234 DETMAR DR, WINTER PARK, FL 32789
$1,645,00071 Days on yellowkey MLS ID: O6379927
Bed: 5 Bath: 5.5 Gar: 1 Liv Area Sq Ft: 3609 Built: 1935 Tax: $13,664 (2025)Community: Osceola Shores Sec 1Spa: NoSingle Family
Taxes:$13,664
Remarks: Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downstairs primary suite offers privacy and comfort with an elegant spa inspired bath. The detached one bedroom guest house is perfect for houseguests, a home office or multi-generational living. The main house has a flexible floor plan that includes four bedrooms and four and one half baths, a sunroom ideal for home office, formal dining room, oversized family room and charming sitting area with fireplace. The kitchen is a chef's delight with six burner gas range, large center island, plentiful l space for gatherings and a separate breakfast room. Other notable features include gleaming wood floors, double pane windows offering abundant natural light, adorable laundry room/mud room. French doors from many rooms open to a classic front porch that is a perfect place for relaxing and enjoying picturesque grounds with towering oaks. Step outside to a private heated pool. Detached garage includes Tesla charging station. This gated compound situated on .42 acres is one block from Lake Osceola and a easy walk to Park Avenue.
Listing Agent: Nicole Seybold (407-808-9374)
1750 CAROLLEE LANE, WINTER PARK, FL 32789
$1,890,00033 Days on yellowkey MLS ID: O6391179
REDUCED by $105,000 (5.3%) on 04/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3249 Built: 2012 Tax: $24,658 (2025)Community: Green Terrace V/140 Lot 3 Blk BSingle Family
Taxes:$24,658
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. In one of Winter Park’s established neighborhoods, residents enjoy access to top-rated schools, tree-lined streets, and proximity to Park Avenue’s renowned dining and shopping, as well as the area’s scenic Chain of Lakes. Originally built in 2012, this four-bedroom, 3.5-bath home offers over 3,200 square feet of thoughtfully designed living space, enhanced by a comprehensive series of recent upgrades. The fully renovated 2025 kitchen serves as centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink, refinished cabinetry and designer hardware, all anchored by an expansive island ideal for gathering and entertaining. The first-floor primary suite provides a private retreat, complemented by a completely renovated spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and an upgraded walk-in shower. Additional 2025 renovations include the powder bath and laundry room, along with new lighting, fresh interior paint, plantation shutters and custom built-ins throughout. Designed for comfort and versatility, the home also features a dedicated office and a spacious upstairs loft with a custom built-in dry bar and beverage refrigerator. Outdoor living is equally inviting, with a private backyard oasis featuring a saltwater pool and spa with sun shelf, travertine decking, and a fully equipped outdoor kitchen with quartzite countertops and custom cabinetry. Electronic roll-down screens and updated landscaping, including a Clusia hedge, provide enhanced privacy and year-round enjoyment. Additional improvements include a new downstairs HVAC system, updated irrigation and sod, exterior paint and a whole-home security system. Move-in ready and ideally located, this home offers a seamless blend of modern upgrades and timeless design.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Michelle Hochfelder (407-221-5073)
675 OVERSPIN DR, WINTER PARK, FL 32789
$775,00072 Days on yellowkey MLS ID: O6378975
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3062 Built: 2010 Tax: $11,578 (2025)Community: Dubsdread HeightsSingle Family
Taxes:$11,578
Elementary School: Princeton Elem
Remarks: Seller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatile layout, and the best of Winter Park at your doorstep! With Dubsdread Golf Course just around the corner and Fairbanks Avenue minutes away, this 4-bedroom, 3.5-bath CUSTOM BUILT HOME puts you in the center of it all – NO HOA required! Major systems have been well maintained; including a NEW A/C UNIT with UV lights (2025), FRESH INTERIOR PAINT, NEWER WATER HEATER (2021), double-pane windows, and the aerobic septic system was recently serviced (2022). All that is left is to move in and enjoy the lifestyle! This home’s flexible floor plan delivers TWO PRIMARY SUITES – one on the first floor and another upstairs – making it ideal for multi-generational living, in-laws, long-term guests, or simply room to grow. The downstairs suite features a spa-like en-suite bath with dual sinks, a SOAKING TUB, large glass shower, and a WALK-IN/THROUGH CLOSET that connects directly to the main floor laundry. Upstairs, the second suite offers a private bath and direct access to a balcony. The SECOND LAUNDRY ROOM upstairs and huge 30x11 BONUS/UTILITY ROOM provide even more convenience and space. At the heart of the home you will find a GOURMET KITCHEN, crafted with the home chef in mind offering an LG STUDIO REFRIGERATOR, INDUCTION COOKTOP, DOUBLE WALL OVEN, sleek stone counters and a complementary backsplash, upgraded cabinetry, and a large ISLAND with bar seating and chic pendant lighting. The kitchen flows seamlessly into the OPEN LIVING AND DINING AREAS, making everyday living or hosting family and friends a breeze. The LOFT at the top of the stairs delivers additional flexible living space and includes a wet bar with fridge, perfect for a casual hangout space, movie room, office space or anything else you or your family might need. TILE AND WOOD FLOORS, crown molding, and an abundance of natural light give the interior a modern yet timeless feel. Outside you will enjoy stylish curb appeal with a paver driveway – plus a COVERED LANAI overlooking a FENCED BACKYARD, and the spacious lot offers plenty of room for outdoor living. From golf, fine and casual dining to shopping, top-rated schools like Princeton Elementary, and easy access to I-4, 426, and 436, everything you love about Winter Park is right at your fingertips! This home offers the upgrades, the space, and the location you have been waiting for. Call today to schedule a tour and fall in love with your new HOME SWEET HOME!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
4923 N MAGNOLIA AVE, WINTER PARK, FL 32792
$390,00015 Days on yellowkey MLS ID: O6396378
0 Days Off yellowkey (back on 4/7/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1559 Built: 1953 Tax: $2,479 (2025)Community: Suburban HomesSingle Family
Taxes:$2,479
Remarks: Charming MOVE-IN Ready Solid Block 3 bedroom, 2 bath Winter Park home. This home features updated kitchen and baths, newer flooring, newer Roof- 2021, Water heater-2023, AC-2016. The home has been re-plumbed and offers newer windows-2018. Beautiful Tongue-N-Grove Woodwork covers the ceiling & walls Bonus room/Den. The home offers a split floor plan and is constructed with plaster walls, its solid and energy efficient. The home is zoned for Top-Rated, sought after Winter Park High School, Maitland Middle and Lakemont Elementary. The very best location. This one won't last long..............
Listing is courtesy of: A+ REALTY PROFESSIONALS, INC (407-702-5243)
Listing Agent: Darlene Chance (407-247-2307)
1127 WILDMEADOW RUN, WINTER PARK, FL 32792
$675,000140 Days on yellowkey MLS ID: O6364368
0 Days Off yellowkey (back on 3/19/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2196 Built: 2020Monthly Fee: $243 Tax: $6,882 (2024)Community: Meadows At Hawks CrestSingle Family
Taxes:$6,882
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This is not just a listing—it is the rare, fully-curated luxury opportunity you’ve been waiting for inside Winter Park’s security-gated Hawks Crest community. This 4-Bedroom, 2.5-Bathroom Taylor Morrison home, built just 5 years ago, professionally cleaned and has been elevated by a recent $20,000+ DESIGNER transformation, making it superior to any comparable new construction. We've handled every high-end detail; you simply move in. The curb appeal is instant, featuring freshly trimmed landscaping, a paver driveway and tile roof for longevity. The interior is pure sophistication. The open-concept living area boasts architectural drama, highlighted by stunning, custom-made 18-FOOT CURTAIN DRAPES (a $5,000 investment) that accentuate the room's height. The kitchen is a chef’s dream, centered around the cutting-edge Samsung BESPOKE refrigerator, complemented by refined cabinetry hardware and brand-new, premium plumbing fixtures. Your HOA DUES COVER FITNESS CENTER, POOL, DOCK, CLUBHOUSE, AND FULL LAWN MAINTENANCE, ensuring a low-maintenance, turn-key experience from day one. Every space radiates quality: the new Designer LIGHTING PACKAGE creates the perfect ambiance throughout, while all baths are appointed with sleek contemporary mirrors and modern accents, including a premium Kohler toilet in the Master Suite. Functionality is also premium, featuring a newly installed, $7,000 value of top-quality exterior GUTTERS for superior drainage and protection. Step outside to your private, beautifully constructed enclosed outdoor sanctuary, offering comfortable, year-round enjoyment. The location is unparalleled: less than a short distance from Park Maitland Preschool, Kelly’s Ice Cream, and Foxtail Coffee right at the community entrance. You are moments from everything: 15 minutes to Park Avenue and rapid access to Orlando's best. It is also perfectly positioned for easy access to world-class entertainment, being just 40 minutes from Walt Disney World and Universal's Epic Studios. This is the chance to secure a truly turn-key, designer-finished home in Winter Park, positioned to sell immediately. With a level of finish this immaculate and demand this high. If you want this home, tell your agent to secure your time slot immediately.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Christopher Beverly (407-394-7424)
4790 TANGERINE AVE #4790, WINTER PARK, FL 32792
$194,99565 Days on yellowkey MLS ID: O6380539
REDUCED by $20,000 (9.3%) on 04/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1058 Built: 1973 Tax: $2,253 (2024)Community: Wrenwood CondoCondo
Taxes:$2,253
Remarks: Move right into this beautifully two-bedroom, two-bath condominium located in desirable East Winter Park. The thoughtfully designed floor plan offers two spacious bedrooms, and bathrooms—one featuring a tub and the other a shower—providing comfort and privacy. The light-filled great room showcases attractive laminate wood flooring and sliding glass doors that open to a private, screened-in porch overlooking a sunny, landscaped courtyard—perfect for relaxing. Recent upgrades include a new AC system (May 2021), a new roof (2022), exterior paint 2025, updated bathrooms, upgraded laminate wood flooring throughout. The primary bathroom has been enhanced with a luxurious walk-in shower featuring upgraded stone and tile finishes. This unit is quietly situated in a private location within the well-maintained Wrenwood Condominiums community, offering assigned parking directly in front of the unit and access to a sparkling community swimming pool. Ideally located in East Winter Park, this community offers easy access to Park Avenue shopping and dining, Winter Park Village, Full Sail University, and nearby parks and lakes. Enjoy a vibrant lifestyle with museums, farmers markets, scenic walking areas, and the renowned Winter Park Chain of Lakes just minutes away, all while remaining close to major roadways and downtown Orlando. Schedule your private showing today.
Listing is courtesy of: SUNSHINE BROKERAGE, LLC (407-509-7961)
Listing Agent: Sonny Manku (407-509-7961)
5275 PINE LILY CIR, WINTER PARK, FL 32792
$665,00082 Days on yellowkey MLS ID: O6377988
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3152 Built: 2014Monthly Fee: $182 Tax: $7,425 (2024)Community: Sanctuary At AlomaSpa: YesSingle Family
Taxes:$7,425
Remarks: Located in desirable Winter Park, this POOL home offers exceptional value. This spacious 5-bedroom plus den area, 3.5-bathroom house has a beautiful pond view from the front door. 3 car garage space and 6 car driveway give you plenty of space for storage and parking. 3,111 square feet of comfortable living space plus a gorgeous screened-in pool with spa. The home features high ceilings that create an open, airy feel throughout. The kitchen showcases elegant granite counters and modern stainless steel appliances. Hard flooring flows through the main living areas, offering both style and easy maintenance. Solar panels on the home save you hundreds each month on electricity. SELLER WILL PAY OFF SOLAR PANELS AT CLOSING! Step outside to your private backyard oasis with a screened-in pool and jacuzzi spa, ideal for year-round Florida living. The fully vinyl fenced yard provides privacy and security for families and pets. This move-in ready property means you can start enjoying your new home immediately. The location offers incredible convenience with easy access to Winter Park shopping, restaurants, and world-famous theme parks. Major roads are nearby, making commuting simple whether you work locally or need to travel throughout Central Florida. The gated community adds security and peace of mind. Winter Park is known for its charming downtown area, excellent schools, and beautiful parks. This neighborhood combines suburban tranquility with urban accessibility, giving you the best of both worlds. Schedule your showing today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Kathy Williams (407-230-7305)
1500 HARRIS CIR, WINTER PARK, FL 32789
$1,295,00070 Days on yellowkey MLS ID: O6379012
Bed: 2 Bath: 3.0 Liv Area Sq Ft: 2096 Built: 1994 Tax: $11,846 (2024)Community: Sylvan Lake ShoresSingle Family
Taxes:$11,846
Remarks: Tucked along one of Winter Park’s charming brick streets and positioned directly across from Lake Sylvan, this recently renovated residence unfolds like a quiet design story, one where character, craftsmanship and modern ease are aligned. From the moment you arrive, the home’s inviting curb appeal and reimagined cottage gardens set the tone, offering a sense of arrival that feels timeless and effortlessly refined. Inside, light pours through expansive picture windows, illuminating marble floors that flow seamlessly through the living room, dining area and kitchen. Every space has been thoughtfully curated by New York City–based interior designer Paulette Pascarella, where classic architecture is elevated by contemporary finishes and a restrained, sophisticated palette. The new kitchen serves as a centerpiece and a gathering space, featuring custom cabinetry, quartz countertops with a full-height backsplash and a high-end appliance suite anchored by a Bertazzoni refrigerator, equally suited for everyday living or intimate entertaining. Just beyond, the family room or den introduces warmth and texture with beautiful wood floors and custom built-ins designed for function and form. Motorized shades by The Shade Store, lighting by Visual Comfort and Currey, and hardware details by Buster + Punch are layered throughout the home, complemented by exquisite textile selections from Brunschwig, Schumacher, Thibaut, and Cowtan & Tout, each detail quietly reinforcing the level of thought and design intention behind the renovation. The second floor is a serene retreat and allows for elevated view of Lake Sylvan. The primary suite with soaring ceilings offers a generous window framing treetop views. The spa-inspired bath features a large glass-enclosed shower and a custom built-in dressing area, creating a private sanctuary that feels removed from the everyday. Two additional bedrooms, one with an en-suite bath, complete the upper level, offering flexibility for guests, work-from-home needs or extended stays. Outdoors, the grounds have been thoughtfully reimagined to evoke a cottage garden feel, providing a peaceful backdrop for morning coffee or evening strolls along the brick-lined street. The location is equally compelling, in a neighborhood known for its winding roads and timeless charm, just minutes from shopping, dining and cultural offerings of Park Avenue. Offering a lock-and-leave lifestyle, this home lives beautifully as a primary residence or as a second or third home and presents a compelling alternative to condominium or townhome living, where privacy, design and a desired Winter Park setting come together in one exceptional offering. There is potential for a third bedroom suite by converting the den/family room on the first floor as it is adjacent to a full bath.
Listing Agent: Mick Night (407-629-4446)
823 GRANVILLE DR, WINTER PARK, FL 32789
$1,400,00023 Days on yellowkey MLS ID: O6394306
1 Days Off yellowkey (back on 4/7/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2544 Built: 1963 Tax: $7,623 (2025)Community: Park GroveSingle Family
Taxes:$7,623
Elementary School: Dommerich Elem
Remarks: Timeless Olde Winter Park charm meets relaxed Florida living at 823 Granville Drive, a true Park Grove gem on an expansive 100' x 135' lot. Nestled among tree-lined streets in this coveted, well-established neighborhood, this single-story residence offers 4 bedrooms, 3.5 baths, and effortless indoor-outdoor living. Thoughtfully designed for entertaining, the home features two fireplaces that anchor inviting living and family spaces, creating a warm, elegant backdrop for gatherings large and small. The open, flowing layout keeps daily living convenient on one level while offering plenty of separation for guests or multi-generational living. Step outside to your own private retreat: a screened, enclosed pool area that feels like an outdoor living room, perfect for morning laps, weekend barbecues, or evening cocktails. The generous lot provides room to play, garden, or simply enjoy the lush surroundings and privacy Park Grove is known for. Practical features include a two-car garage, ample storage, and the rare opportunity to own a pool home in one of Winter Park’s most sought-after neighborhoods, just minutes to Park Avenue shopping, dining, lakes, and cultural venues. This is the Park Grove lifestyle—single-story, pool, charm, and location—all in one compelling property.
Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)
Listing Agent: Anthony Consalvo (407-599-7070)
291 LEWFIELD CIR #291, WINTER PARK, FL 32792
$144,00065 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
Remarks: One of the best 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)
2530 LEEWARD WAY, WINTER PARK, FL 32792
$265,00070 Days on yellowkey MLS ID: O6380907
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1199 Built: 1976Monthly Fee: $99 Tax: $795 (2024)Community: Windward Square Sec 1Townhouse
Taxes:$795
Remarks: Well-maintained 2-bedroom, 2-bath home with 1,199 sq ft in a desirable Winter Park 32792 location offering a fenced backyard, low HOA, and a flexible bonus space ideal for a home office, study, or hobby area. The functional split-bedroom layout provides privacy, while the open living and dining areas create a comfortable space for everyday living or entertaining. The kitchen offers ample cabinetry and counter space, flowing seamlessly to the main living area plus upgraded appliances. The primary suite includes a private bath and generous closet space, while the secondary bedroom and full bath provide flexibility for guests, office use, or additional living needs. Enjoy outdoor living in the fully fenced yard—ideal for relaxing, gardening, or pets. Additional highlights include driveway parking, interior laundry, and low-maintenance living. -- NEW ROOF IN PROCESS -- Prime location with convenient access to major corridors and top destinations: ˜ 3 mi to Full Sail University, ˜ 5 mi to UCF, ˜ 4 mi to AdventHealth Winter Park, and ˜ 6 mi to Park Avenue and Downtown Winter Park. Nearby shopping, dining, and grocery options are within minutes, with quick connectivity to SR-436, University Blvd, and SR-417 for commuting throughout Central Florida. An excellent opportunity to own in Winter Park with space, privacy, and strong location value.
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