Location: Winter Park
Do Not Show Listings
7488 WHISPERWOOD DR #28, WINTER PARK, FL 32792
$230,000Listed 06/23/2026 2:23PM MLS ID: O6419151
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1578 Built: 1974Monthly Fee: $575 Tax: $3,078 (2025)Community: Whisperwood CondoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,078
Elementary School: Cheney Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Welcome to Whisperwood, where space, convenience, and investment potential come together in one exceptional opportunity. This rare gem is a beautifully maintained 2-bedroom, 2.5-bath residence offering a rarely available townhome-style floor plan that combines generous living spaces, exceptional functionality, and outstanding investment potential. The spacious multi-level layout features expansive living and dining areas, a convenient guest powder bath, and two oversized dual primary-style suites, each with its own private bathroom. The thoughtfully designed floor plan delivers the privacy, flexibility, and comfort today's buyers are seeking. Natural light fills the interior, while the private balcony provides the perfect retreat for morning coffee or evening relaxation. A private fenced backyard opens to a lush green space, creating a peaceful outdoor setting rarely found in condominium living. Additional highlights include a covered carport, dedicated laundry closet, abundant storage throughout, and a large second-floor storage room. Residents enjoy a truly low-maintenance lifestyle with access to Whisperwood's sparkling community pool, clubhouse, and beautifully landscaped grounds. The HOA provides exceptional value by covering exterior building maintenance, grounds maintenance, water, sewer, trash, pest control, pool maintenance, recreational facilities, and common area upkeep. Perfectly positioned near SR-417, Goldenrod Road, and University Boulevard, this prime location offers seamless access to Downtown Orlando, Winter Park, Orlando International Airport, major employment centers, premier shopping and dining destinations, and Central Florida's world-famous attractions. For investors, this property represents a compelling income-producing opportunity. Currently tenant-occupied, offers immediate cash flow, Its strategic location near UCF, Full Sail University, Valencia College, and Seminole State College supports strong, year-round rental demand, making it an attractive move-in ready investment with enduring appeal. Whether you're searching for a primary residence, a low-maintenance lifestyle, or a strategic addition to your investment portfolio, this exceptional Whisperwood residence offers the perfect blend of space, location, convenience, and value.
Listing is courtesy of: PARKVIEW REAL ESTATE (407-312-6472)
Listing Agent: Miranda Azer (407-312-6472)
1564 LAWNDALE CIR, WINTER PARK, FL 32792
$450,000Listed 06/23/2026 1:02PM MLS ID: O6418817
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1980 Built: 1985Monthly Fee: $46 Tax: $3,124 (2025)Community: Country LaneSingle Family
Taxes:$3,124
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Discover the potential of this spacious 4-bedroom, 2.5-bath home located at 1564 Lawndale Cir in desirable Winter Park. Featuring a comfortable floor plan with generous living space, this home offers flexibility for everyday living, entertaining, working from home, or hosting guests. The bedroom layout provides privacy and functionality, while the location offers convenient access to shopping, dining, parks, schools, major roadways, and nearby Orlando destinations. With its size, layout, and prime Winter Park location, this property is a great opportunity for buyers looking to personalize a home and create lasting value. Don’t miss your chance to schedule a private showing.
Listing is courtesy of: SET HOMES REALTY LLC (407-690-3314)
Listing Agent: Yahya Chhotani Llc (732-955-1302)
948 POINCIANA LN, WINTER PARK, FL 32789
$2,899,900162 Days on yellowkey MLS ID: O6372165
REDUCED by $274,100 (8.6%) on 06/13/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3676 Built: 2001 Tax: $19,753 (2025)Community: Maitland Shores First AddSpa: YesSingle Family
Taxes:$19,753
Elementary School: Dommerich Elem
Middle School: Maitland Middle
Remarks: Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an extraordinary residence where exceptional craftsmanship and sophisticated design converge at 948 Poinciana Lane. This meticulously reimagined estate represents the pinnacle of refined living in one of Winter Park's most prestigious neighborhoods, offering an effortless blend of classic architecture and contemporary luxury. From the moment you step through the elegant foyer, you're greeted by sun-drenched interiors showcasing gleaming hardwood floors, soaring coffered ceilings, and designer details at every turn. The thoughtful floor plan reveals a private home office with custom built-ins and fireplace to the right, and a gracious formal dining room to the left—perfect for hosting memorable gatherings. The heart of this home is the spectacular kitchen, a true chef's masterpiece featuring custom cabinetry, pristine marble countertops, statement pendant lighting, and top-tier appliances. This culinary haven flows seamlessly into the light-filled family room, where expansive windows frame views of your private outdoor sanctuary. The first-floor primary retreat is a haven of tranquility, featuring an expansive walk-in dressing room with exceptional storage and a spa-inspired ensuite bath. Luxuriate in the freestanding soaking tub, refresh in the walk-in shower, or prepare for your day at the generous double vanity—all appointed with elegant finishes befitting this caliber of home. Three generously proportioned guest bedrooms upstairs offer optimal comfort and privacy, complemented by a Jack-and-Jill bath and additional hall bath. A spacious bonus room with backyard views provides versatility for a media room, playroom, or home gym. Above the garage, an additional 260-square-foot bonus room with wet bar and wine fridge creates the ideal entertainer's lounge or game room. Step through French doors to your private resort-style backyard—a meticulously landscaped oasis featuring a sparkling pool and spa surrounded by lush greenery, stately palms, and thoughtful lighting. Whether gathering around the firepit, lounging poolside, or dining alfresco under the stars, this outdoor retreat elevates everyday living to an art form. No detail has been overlooked in this complete renovation: designer light fixtures and custom window treatments throughout, first-floor laundry convenience, elevated trim and baseboard, fresh paint, recessed lighting, and three HVAC units ensuring year-round comfort. The location is simply unparalleled—a leisurely stroll to the Winter Park Racquet Club, zoned for A-rated public schools, and just moments from the world-renowned shops and restaurants of Park Avenue. This is more than a home; it's a lifestyle of distinction in Central Florida's most desirable address.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792
$250,00064 Days on yellowkey MLS ID: O6400674
REDUCED by $9,000 (3.5%) on 06/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1295 Built: 1985Monthly Fee: $499 Tax: $2,560 (2024)Community: Cedarwood Village 1Condo
Taxes:$2,560
Elementary School: English Estates Elementary
Tax Year: 2024
Remarks: Nestled in a peaceful setting within the serene Cedarwood Village community, this charming one-story Winter Park condo offers a quiet retreat away from traffic noise, with a rear wooden fence for no visible neighbors for added privacy. The spacious 27-foot tiled and enclosed lanai creates the perfect place to relax and enjoy the tranquil surroundings. Cedarwood Village also offers low-maintenance living, with lawn care included in the HOA, along with amenities such as rebuilt tennis courts, a recently remodeled pool, a clubhouse, dog-walking areas, and newly paved roads. Conveniently located in a highly rated school district and close to shopping, dining, and entertainment, the property is also just minutes from Full Sail University, Valencia College, and UCF. Inside, the condo is beautifully updated and shows the care of meticulous owners. The modern kitchen features granite countertops, matching cabinetry, and an eat-in area with sliding doors leading to the private patio, while the bathrooms and dining room wet bar are finished with the same stylish cabinets and granite. The split floor plan includes tile flooring throughout the main living areas and wood floors in the bedrooms. The large living and dining spaces feature vaulted ceilings with skylights for abundant natural light, along with a cozy wood-burning fireplace. French doors from the living room open to the enclosed lanai, while the primary suite also has direct lanai access, ample closet space, and a private bath with both a tub and shower. Additional features include an interior laundry closet adjacent to the kitchen, updated plumbing, a roof replaced in 2018, and new ductwork installed in 2023. AC 2008. Seller providing a $4,500 Buyer credit at closing toward a new AC. Two assigned parking spaces are located directly in front of the unit.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)
Listing Agent: Jeff Stewart (407-247-9762)
102 BELL PL, WINTER PARK, FL 32792
$1,399,00070 Days on yellowkey MLS ID: O6398118
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2459 Built: 2025 Tax: $4,224 (2025)Community: Eastgate SubSpa: NoSingle Family
Taxes:$4,224
Elementary School: None
High School: None
Middle School: None
Remarks: Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for superior durability, this home is quietly nestled on a cul-de-sac in one of Winter Park’s most up-and-coming areas—without the restrictions of an HOA. Just moments from Interlachen Country Club and the charming Lakemont Heights neighborhood, the location offers both prestige and convenience. From the moment you enter through the impressive double doors, you’re welcomed by a light-filled, open-concept design. Soaring 10-foot ceilings and elegant 8-foot doors create an airy, expansive feel, while abundant natural light highlights the home’s sleek, contemporary finishes. At the heart of the home, the chef-inspired kitchen truly shines. Outfitted with luxurious quartz countertops, stainless steel appliances, and a custom LED-lit wine display, it’s designed to impress. The seamless flow into the living and dining spaces—along with views of the backyard—makes it perfect for entertaining or everyday connection. The primary suite is a private sanctuary, offering a spa-like escape with dual vanities, a spacious dual-entry shower, and a freestanding soaking tub designed for relaxation. With three additional bedrooms, a dedicated office, and 3.5 beautifully appointed bathrooms, this thoughtfully designed single-story home provides nearly 2,500 square feet of flexible living space. Outdoors, your personal retreat awaits. Enjoy year-round Florida living on the covered lanai, complete with a built-in summer kitchen and a custom-designed pool—ideal for hosting or unwinding. The fully fenced yard features new vinyl fencing, fresh sod, and an automated sprinkler system for effortless maintenance. Perfectly positioned near Phelps Park, the Winter Park YMCA, Lakemont Elementary, and an array of top-tier shopping and dining destinations, this home delivers the ideal blend of privacy, craftsmanship, and everyday luxury.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Nick Mckee (407-913-0171)
240 N PHELPS AVE, WINTER PARK, FL 32789
$2,250,00012 Days on yellowkey MLS ID: O6415360
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2889 Built: 2026 Tax: $6,605 (2025)Community: Sylvan HeightsSingle Family
Taxes:$6,605
Elementary School: Brookshire Elem
Remarks: A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.
2712 TORTOISE CV, WINTER PARK, FL 32792
$235,000Listed 06/23/2026 12:31PM MLS ID: O6419150
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 924 Built: 1981 Tax: $2,442 (2025)Community: Slovak VillageHalf Duplex
Taxes:$2,442
Remarks: Why Rent WHEN you can own this 2 bedroom 1 bath single car garage on this 1/2 duplex with NO HOA. Located conveniently to all major roads, shopping, schools and restaurants. New roof installed 2025. Don't hesitate to come view!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Lisa Wright (321-231-3141)
2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792
$259,00067 Days on yellowkey MLS ID: O6398500
REDUCED by $10,000 (3.7%) on 06/04/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1295 Built: 1987 Tax: $1,107 (2025)Community: Cedarwood Village 1Condo
Taxes:$1,107
Remarks: Discover comfort and convenience in this charming, spacious 2-bedroom, 2-bath residence nestled in the heart of Winter Park! Step inside to an inviting living room with a vaulted ceiling. The fully equipped open-floor kitchen, featuring ample roomy cabinets, is perfect for everyday living and entertaining. The thoughtfully designed split floor plan enhances functionality and privacy. Elegant, durable flooring throughout the home ensures easy maintenance. Enjoy the walk-in shower and bathtub with upgraded plumbing and tile. A convenient coffee nook sits just off the kitchen. The spacious patio is ideal for entertaining guests and enjoying outdoor time. Community amenities include a swimming pool and tennis courts, supporting a low-maintenance, active lifestyle.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Robert Arnold, Jr (407-389-7318)
1023 WORTHING CT, WINTER PARK, FL 32792
$450,00011 Days on yellowkey MLS ID: O6416552
0 Days Off yellowkey (back on 6/23/2026)
REDUCED by $10,000 (2.2%) on 06/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1184 Built: 1983 Tax: $1,092 (2025)Community: Howell Estates 2Nd AddSpa: NoSingle Family
Taxes:$1,092
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, 2-bath home nestled on a quiet cul-de-sac! Featuring a desirable split-bedroom floor plan, this home offers both comfort and privacy. The kitchen includes a convenient breakfast bar, perfect for casual dining and entertaining. Step outside and enjoy true Florida living in the expansive screened lanai overlooking a large, fully fenced backyard filled with lovely flowers and plenty of room to relax or play. The sparkling 26x14 chlorine pool with a 7-foot-deep end is ideal for both entertaining and unwinding. The home also features a side-entry 2-car garage, adding to its curb appeal and functionality. Major updates include a new roof (Nov 2024) and new fence (Dec 2024). Ideally located close to shopping, dining, and with easy access to 417, this home offers the perfect combination of privacy, convenience, and lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Yolon Riveiro (321-228-4708)
501 HERITAGE BLVD, WINTER PARK, FL 32792
$474,900102 Days on yellowkey MLS ID: S5145746
REDUCED by $5,000 (1.0%) on 06/23/2026
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1376 Built: 1966 Tax: $10,434 (2025)Community: Georgetown EstatesSingle Family
Taxes:$10,434
Elementary School: Lakemont Elem
Remarks: Welcome to this beautifully remodeled, move-in-ready home in the highly sought-after Winter Park area. This single-story residence features 4 bedrooms and 2 bathrooms, offering a bright, open floor plan with modern finishes designed for both comfort and functionality. A standout feature of this property is its commitment to sustainable living and energy efficiency. Highlights include: - Newer Roof: Installed in 2023 - Radiant Barrier & Blown-In Attic Insulation: Keeps the Florida heat out and significantly lowers cooling costs. - High-Efficiency HVAC: Energy Star rated AC unit ensuring consistent temperatures and peak savings. Step outside to an expansive backyard featuring a private pool, perfect for relaxing or entertaining. This large outdoor space offers endless possibilities for customization, such as a garden or an outdoor kitchen. Located in a quiet, established neighborhood within an A+ rated school zone, this home provides convenient access to top shopping, dining, parks, and major highways. Don't miss this incredible opportunity to own a fully updated turnkey property in one of the most desirable areas of Winter Park.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Bernardo Carrasquel (407-920-4973)
234 DETMAR DR, WINTER PARK, FL 32789
$1,599,000133 Days on yellowkey MLS ID: O6379927
2 Days Off yellowkey (back on 5/29/2026)
REDUCED by $46,000 (2.8%) on 04/29/2026
Bed: 4 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: Under contract-accepting backup offers. 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 is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Nicole Seybold (407-808-9374)
528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792
$535,00013 Days on yellowkey MLS ID: O6414677
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1656 Built: 1964 Tax: $6,000 (2025)Community: Winter Park PinesSingle Family
Taxes:$6,000
Remarks: Welcome to Winter Park Pines, one of Winter Park's most desirable and established neighborhoods! Situated on nearly a quarter-acre lot, this beautifully maintained home with fresh interior paint combines modern updates, everyday comfort, and an unbeatable location. The stunning recently updated kitchen serves as the heart of the home, featuring stylish finishes and an inviting space for cooking, entertaining, and gathering. Throughout the home, you'll find attractive flooring with no carpet, offering both a clean, modern look and easy maintenance. Major improvements provide peace of mind, including a new roof and complete re-plumbing completed in 2023. The spacious lot offers plenty of room to enjoy outdoor living, gardening, pets, or future possibilities. Location is everything, and this home delivers. Just steps from Cady Way Pool and the popular Cady Way Trail, you'll enjoy easy access to recreation, fitness, and outdoor activities. Residents also love the convenient proximity to restaurants, shopping, parks, golf, and the charm of Downtown Winter Park. Best of all, there is no HOA, providing added flexibility and freedom. With significant recent updates, a generous lot, and a prime location in highly sought-after Winter Park Pines, this move-in-ready home is a wonderful opportunity to enjoy the very best of Winter Park living.
Listing Agent: Jonathan Cole (407-928-9516)
1521 CAVENDISH RD, WINTER PARK, FL 32789
$470,00012 Days on yellowkey MLS ID: O6415985
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1036 Built: 1946 Tax: $2,793 (2025)Community: Orwin Manor WestminsterSingle Family
Taxes:$2,793
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Virtually Staged. Located in the heart of Orwin Manor, one of Winter Park’s most beloved historic neighborhoods, 1521 Cavendish Road is a beautifully renovated 2-bedroom, 1-bath home offering 1,042 square feet of thoughtfully updated living space. Positioned between Winter Park, College Park, and Downtown Orlando, residents enjoy convenient access to AdventHealth, Loch Haven Park, the Orlando Museum of Art, Orlando Science Center, Park Avenue, Ivanhoe Village, and some of the area's most celebrated dining, shopping, and cultural destinations. Surrounded by mature landscaping, manicured hedges, colorful garden beds, and stately palms, the home's curb appeal reflects the character and pride of ownership found throughout the neighborhood. French front doors open to a spacious foyer that leads into a bright family and dining room combination, where new pine laminate flooring, crown molding, plantation shutters, and updated lighting blend historic character with modern comfort. The renovated kitchen features shaker cabinetry, Silestone countertops, stainless steel appliances, abundant storage, and natural light. Both bedrooms have been thoughtfully updated with new flooring, LED recessed lighting, ceiling fans, and plantation shutters, while the recently renovated bathroom pairs basketweave tile flooring, subway tile, quartz countertops, and classic finishes that honor the home's original style. Outside, the large backyard has been transformed into a private retreat featuring a composite deck, new fencing, mature palms, raised garden beds, steel-edged landscaping, and a paver walkway. Thoughtfully updated while preserving its architectural charm, this home offers a rare opportunity to enjoy historic character in a neighborhood that continues to benefit from the growth, investment, and enduring appeal of Winter Park and Downtown Orlando. Schedule your private tour today.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: John Goggin (321-332-3000)
1750 CAROLLEE LANE, WINTER PARK, FL 32789
$1,820,00095 Days on yellowkey MLS ID: O6391179
REDUCED by $70,000 (3.7%) on 05/26/2026
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
Remarks: Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom, 3.5-bath, custom pool and spa residence offers more than 3,200 square feet of thoughtfully updated living space near Park Avenue, the Chain of Lakes and top-rated schools. The fully renovated 2025 kitchen serves as the centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink and an expansive island designed for gathering and entertaining. The first-floor primary suite offers a private retreat with a completely reimagined spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and upgraded walk-in shower. Designed for comfort and entertaining, the home also features a dedicated office and an upstairs loft with a custom dry bar and beverage refrigerator. Outdoors, the backyard lives like a private resort-style oasis, complete with a saltwater pool and spa, sun shelf, travertine decking, electronic roll-down screens and a fully equipped outdoor kitchen designed for year-round enjoyment. Lush new backyard landscaping completed in May 2026, including enhanced privacy elements, creates an intimate outdoor setting rarely found this close to the heart of Winter Park. Additional highlights include updated irrigation supported by a private well, a new downstairs HVAC system and a home warranty provided for the buyer at closing. Move-in ready and impeccably maintained, this residence offers refined living in one of Winter Park’s desirable settings.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Michelle Hochfelder (407-221-5073)
927 FAIRWAY DR, WINTER PARK, FL 32792
$680,00067 Days on yellowkey MLS ID: TB8498515
0 Days Off yellowkey (back on 5/27/2026)
REDUCED by $19,000 (2.7%) on 04/30/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1918 Built: 1973 Tax: $4,784 (2025)Community: Golfside Sec 03Spa: NoSingle Family
Taxes:$4,784
Remarks: Welcome to this beautifully updated home offering the perfect blend of comfort, style and convenience. From the moment you arrive, you’ll notice the inviting tree-lined streets in this quiet residential neighborhood. Step inside to discover a bright, thoughtfully designed layout, filled with natural light, featuring spacious living areas and tasteful updated finishes throughout. The updated, open-concept kitchen is a true centerpiece, complete with modern appliances, ample cabinetry, a generous peninsula, and in eat-in area, ideal for gathering with family and friends. The primary suite provides a relaxing retreat with a recently updated in-suite bathroom and plenty of closet space. Additional bedrooms are generously sized, including a fourth bedroom, perfect for multi-generational living, guests, or a home office. Outside, enjoy a sparkling, screened-enclosed pool, and a private backyard oasis, with plenty of yard space to relax, play, or entertain. Whether you're hosting a weekend barbecue or enjoying a quiet evening, this outdoor space offers endless possibilities. Walk over to the Winter Pines golf course located behind the home, where you can enjoy lunch at the beautifully updated clubhouse, hit the driving range, or enjoy the seasonal community events like Santa in the Park, Movie in the Park, or occasional neighborhood happy hours. Located in the beautiful neighborhood of Winter Park Pines with amenities such as Ward Park, Brookshire Elementary, Winter Park HS, and the Cady Way bike trail, which you can take to Baldwin Park’s main street for shopping and dining, or a stroll around Lake Baldwin. Conveniently located near downtown Orlando, Park Avenue for shopping and dining, or just minutes from the 417 for commuting. Seller offering a home warranty to a buyer for the first year.
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
2889 ROUEN AVE, WINTER PARK, FL 32789
$365,00063 Days on yellowkey MLS ID: L4961275
REDUCED by $10,000 (2.7%) on 06/23/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1959 Tax: $5,061 (2025)Community: Winter Park ManorSingle Family
Taxes:$5,061
Remarks: 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 water heater. 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)
942 ENCLAVE PL, WINTER PARK, FL 32792
$2,195,00026 Days on yellowkey MLS ID: O6411550
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3831 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. 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 an elevated yet livable environment, all set within a beautifully landscaped and private setting. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Matthew Burks (407-257-5347)
926 ENCLAVE PL, WINTER PARK, FL 32792
$2,235,00034 Days on yellowkey MLS ID: O6408030
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4150 Built: 2026Monthly Fee: $124 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
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 an elevated yet livable environment, all set within a beautifully landscaped and private setting. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options.
Listing Agent: Laura Earl (443-994-9441)
938 ENCLAVE PL, WINTER PARK, FL 32792
$2,099,00034 Days on yellowkey MLS ID: O6408090
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3865 Built: 2026Monthly Fee: $124 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
Remarks: Pre-Construction. To be built. Welcome to The Enclave, an exclusive boutique community in the heart of Winter Park featuring just 23 thoughtfully crafted residences by FG Schaub Custom Homes. Nestled beneath mature oak canopies and surrounded by lush natural beauty, this private enclave offers the perfect balance of tranquility, sophistication, and walkable convenience. Ideally located just moments from Phelps Park, the YMCA, premier dining, shopping, and the vibrant charm of downtown Winter Park, residents enjoy an elevated lifestyle in one of Central Florida’s most desirable locations. This stunning custom-designed residence showcases timeless architecture with clean modern farmhouse influences, highlighted by striking curb appeal, refined exterior detailing, and thoughtfully curated landscaping. Inside, exceptional craftsmanship and upscale finishes define every space. Features include high-performance low-E double-pane windows, 8-foot solid-core interior doors, tankless gas water heaters, and an open, livable floor plan designed for both everyday comfort and elegant entertaining. The gourmet kitchen is appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a refined palette of materials and colors. Expansive indoor-outdoor living spaces include a resort-style pool and a fully equipped summer kitchen, creating the ultimate Florida lifestyle experience. Spacious interiors, elevated detailing, and quality construction come together to create a home that is both luxurious and inviting. Buyers still have the opportunity to personalize select finishes and explore certain floor plan modifications. Additional upgrade options may include a detached cabana and/or guest house, subject to lot compatibility, community guidelines, and additional pricing. A rare opportunity to own a truly custom home in one of Winter Park’s most intimate and architecturally distinctive new communities.
910 ENCLAVE PL, WINTER PARK, FL 32792
$1,899,00040 Days on yellowkey MLS ID: O6406803
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3620 Built: 2027Monthly Fee: $124 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
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