Location: Winter Park , 32792
Do Not Show Listings
256 LEWFIELD CIR #256, WINTER PARK, FL 32792
$184,900199 Days on yellowkey MLS ID: O6367842
1 Days Off yellowkey (back on 6/19/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 927 Built: 1973Monthly Fee: $465 Tax: $1,916 (2025)Community: Stratford A Winter Park CondoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,916
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: This charming and well-maintained 2 bedroom, second-floor condo in Winter Park is ready for you to call your own! The home features comfortable carpeted living areas throughout. The centrally located galley kitchen offers plenty of cabinet and counter space and connects directly to the dining room. The spacious living room gets plenty of natural light through large sliding glass doors, opening to a covered and screened rear porch with a pool view. The primary suite features a walk-in closet and a private bath with a floor-to-ceiling tiled walk-in shower. The HOA completed roofing and plumbing improvements in 2019, and all exterior and grounds maintenance is handled by the on-site HOA. The Stratford community offers two pools, a community and fitness center, and tennis courts. Just minutes from popular Downtown Winter Park with its dining and shopping, with easy highway access via the 417 and I-4, and surrounded by nearby lakes and parks, this is one opportunity you don’t want to miss. Call today to schedule your private tour!
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Renee Kumar Llc (407-756-4422)
7327 FOREST HILL CT #223, WINTER PARK, FL 32792
$175,00086 Days on yellowkey MLS ID: O6403841
REDUCED by $5,000 (2.8%) on 07/28/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1031 Built: 1984Monthly Fee: $450 Tax: $2,597 (2025)Community: Hidden Oaks Condo Ph 12Condo
Taxes:$2,597
Elementary School: None
High School: None
Middle School: None
Remarks: Looking for the perfect starter home or great little rental. This townhhouse-style condo with 2 master suites. With granite countertop on kitchen. Open floor plan, inside laundry closet off the dinette. Tile flooring downstairs and carpet up, additional exterior storage room and fenced in patio. garbage. Hidden Oaks community features community pool & fenced playground area. Zoned for Winter Park Schools. Conveniently located just: 10 minutes to Downtown Orlando, 15 minutes to Orlando International Airport, 10 minutes to shopping and dining, 15 minutes to Valencia College, 25 minutes to UCF, 30 minutes to Disney World. Easy access to FL-408 & FL-417.
Listing is courtesy of: M L VAZ REALTY INC (407-380-9397)
Listing Agent: Leda Vaz (407-509-7947)
1840 ASTER DR, WINTER PARK, FL 32792
$414,90058 Days on yellowkey MLS ID: O6412364
REDUCED by $5,000 (1.2%) on 07/28/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1667 Built: 1978 Tax: $864 (2025)Community: Garden Lake Estates Unit 1Spa: NoSingle Family
Taxes:$864
Elementary School: Red Bug Elementary
Remarks: Step into this well maintained 3 bedroom 2 bath home located in a highly sought after Winter Park, Garden Lake Estates. Nestled in Seminole County, A rated school zone! The home also sits on a large lot with plenty of room for outdoor living, No rear neighbors for added privacy, gardening or future expansion. This property offers endless potential. Featuring a newer roof, this home offers added value and peace of mind for its next owner. Conveniently located near shopping, schools, dining, parks and major roadways, you'll enjoy both comfort and convenience.One or more photo(s) have been virtually staged.
Listing is courtesy of: KONA REALTY SERVICES LLC (407-960-6844)
Listing Agent: Brendon Spalding (407-929-1724)
102 BELL PL, WINTER PARK, FL 32792
$1,399,000106 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
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)
433 GILBERT RD, WINTER PARK, FL 32792
$675,0002 Days on yellowkey MLS ID: O6428430
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1770 Built: 1965 Tax: $4,032 (2025)Community: Winter Park PinesSpa: NoSingle Family
Taxes:$4,032
Elementary School: Brookshire Elem
High School: Winter Park High
Middle School: Glenridge Middle
Remarks: Welcome to this beautifully updated three-bedroom, two-bathroom pool home offering nearly 1,800 square feet of thoughtfully designed living space on a spacious lot backing to a peaceful conservation easement. Featuring separate living and family rooms, a remodeled kitchen, and an exceptional outdoor retreat, this inviting home is perfectly designed for both everyday living and entertaining. From the moment you arrive, the classic brick entry creates a warm first impression. Inside, the flexible floor plan provides plenty of space to gather, relax, work from home, or host guests. Laminate wood flooring and updated baseboards (2022) complement plantation shutters, recessed lighting, and ceiling fans throughout. Multiple storage closets add everyday functionality, while updated windows and French doors fill the home with natural light and seamlessly connect the indoor and outdoor living spaces. The remodeled kitchen (2021) features crisp white shaker cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, an oversized stainless-steel sink, and a breakfast bar with seating for four. A dedicated coffee bar and pantry add convenience, while the large bay window overlooks the pool and private backyard, creating the perfect backdrop for everyday living. The spacious primary suite offers a walk-in closet and ceiling fan. Its ensuite bathroom, renovated in 2022, features large marble-look tile, a double vanity with quartz countertops, and a beautifully updated walk-in shower with a frameless glass enclosure. Two additional guest bedrooms and an updated full bathroom complete the bedroom wing. Step outside to the true centerpiece of the home. Backing to a conservation easement, the backyard offers a peaceful setting with enhanced privacy. The screened, in-ground chlorine pool was completely refreshed in 2025 with new tile, repaired beam, resurfacing, and new pool light. The lanai deck was also resurfaced, creating an ideal space for swimming, outdoor dining, and entertaining family and friends. The outdoor improvements continue with fresh landscaping completed in 2025, including new sod, a stone pathway, French drains for improved drainage, and an updated irrigation timer. The fully fenced backyard (2023) provides additional privacy for pets, play, and gatherings. Ideally located near Cady Way Trail and Winter Park Pines Golf Course, you'll also enjoy convenient access to Cady Way Park amenities, including a community pool, playground, tennis and pickleball courts, beach volleyball, and walking trails. AdventHealth Winter Park and the Crosby Wellness Center are just minutes away, while Rollins College, Full Sail University, UCF, and Orlando International Airport are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines modern updates, flexible living spaces, and a private backyard retreat in one of Winter Park's most desirable locations. ROOF - 2024 ELECTRICAL PANELS - 2021
Listing Agent: Amy Turner (407-803-3885)
651 DARCEY DR, WINTER PARK, FL 32792
$500,0002 Days on yellowkey MLS ID: O6428379
0 Days Off yellowkey (back on 7/27/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1866 Built: 1967 Tax: $7,847 (2025)Community: Brookshire HeightsSingle Family
Taxes:$7,847
Remarks: Under contract-accepting backup offers. An opportunity to purchase a home in an established Winter Park neighborhood on quiet street, close to great schools and AdventHealth Winter Park Hospital. Perfect for renovation or a new build.
Listing is courtesy of: ANNE ROGERS REALTY GROUP INC (407-649-4141)
Listing Agent: Becky Dobson (407-617-6026)
1320 GLADIOLAS DR, WINTER PARK, FL 32792
$474,00061 Days on yellowkey MLS ID: O6412139
REDUCED by $1,000 (0.2%) on 07/28/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1624 Built: 1983 Tax: $1,380 (2025)Community: Garden Lake Estates Unit 3Single Family
Taxes:$1,380
Remarks: Been looking for a 4 bedroom home? Well, you have found it!!! This one owner home definitely shows pride of ownership! The attention to detail is obvious! Some of the upgrades include a 10 KW solar panel system, double pane gas insulated windows throughout the house and the enclosed lanai. The kitchen has LG appliances and granite countertops. Both bathrooms have updates as well. The house has ceramic tile throughout and bamboo flooring in the master bedroom. More updates include Trane A/C system, newer water heater, roof in 2021, and electrical panel in 2017. Also included are a garage door opener that has battery backup for power outages, ring door sensors on all main windows and doors, motion activated lights at night on all 4 sides of home, a water softener, and an I-Flo system on the A/C. All that, and a desirable neighborhood with highly rated schools! You don't want to miss this one! Make your appointment today!!!
Listing is courtesy of: OPTIMA REAL ESTATE (407-366-4500)
Listing Agent: Deborah Morgan (407-314-8610)
145 SCOTTSDALE SQ, WINTER PARK, FL 32792
$99,90014 Days on yellowkey MLS ID: O6424788
0 Days Off yellowkey (back on 7/28/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1020 Built: 1974Monthly Fee: $880 Tax: $1,552 (2025)Community: Winter Park Woods CondoCondo
Taxes:$1,552
Remarks: Under contract-accepting backup offers. Move-in ready! Fully updated 2 bedroom/2 bath condo located in Winter Park for under 100k! Conveniently located on the first floor for easy access. Open kitchen overlooks the spacious great room and features white cabinets, Stainless Steel appliances, Granite counters, and breakfast bar. Split bedroom plan with 2 full baths featuring Granite counters and beautiful tiled showers/tubs. Neutral wood look laminate flooring throughout. Sliding doors lead to a private patio, providing a relaxing outdoor space, plus a private laundry room with washer/dryer and extra storage space with shelving. This unit offers a premium location with pool, clubhouse, and tennis right behind this building. Residents enjoy low-maintenance living with HOA coverage that includes building exterior and landscaping maintenance, pest control, water, access to two community pools, a playground, and tennis courts. Located in the desirable Winter Park area, this condo offers easy access to downtown Winter Park retail and restaurants, Full Sail, UCF, Valencia College, Rollins College, and Highways 417 and 408 for easy commuting. Also nearby are Sam's Club, Costco, Publix, Sprouts, Target, Walmart, and the Cady Way Trail for walking/biking. Zoned for highly rated Winter Park schools! This condo is perfect as a primary residence, vacation getaway, or investment opportunity with very strong rental demand. Note - NEW appliances are being installed around August 3 - refrigerator, range, microwave, and dishwasher.
Listing is courtesy of: GENSTONE REALTY (407-237-0905)
Listing Agent: Shaunda Hall (407-625-4044)
1438 TIERRA CIR, WINTER PARK, FL 32792
$514,90088 Days on yellowkey MLS ID: O6403855
REDUCED by $5,000 (1.0%) on 06/24/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1627 Built: 1968 Tax: $1,630 (2024)Community: Casa AlomaSpa: NoSingle Family
Taxes:$1,630
Tax Year: 2024
Remarks: Charming, Fully Renovated Pool Home in Sought-After Winter Park. Welcome to this beautifully updated pool home, ideally located in desirable Winter Park—just minutes from premier shopping, dining, and entertainment, with easy access to major roadways for a seamless commute. From the moment you step inside, you’re greeted by a warm, modern aesthetic that blends comfort with style. To the right, a spacious step-down living room offers abundant natural light and lovely views of the front yard. To the left, the formal dining room flows effortlessly into the heart of the home—a stunning, fully renovated kitchen and inviting family room overlooking the private pool and patio. The kitchen is designed to impress, featuring solid wood cabinetry, stainless steel appliances, sleek modern lighting, ample counter space, and a center island perfect for gathering. The adjoining family room is anchored by a stylish electric fireplace, creating a cozy ambiance while offering serene views of the outdoor living area. This home features a desirable split-bedroom floor plan, providing privacy and flexibility. The primary suite is tucked away on one side, while two additional bedrooms and a full bathroom are located on the opposite wing—ideal for family or guests. Extensive upgrades provide peace of mind and modern appeal, including a newer roof (2021), a newer AC (2019) fully renovated kitchen and bathrooms, 5-inch baseboards, knockdown ceiling texture, textured walls, luxury vinyl plank flooring throughout, fresh interior and exterior paint, and updated electrical and plumbing fixtures. Step outside to your private oasis—a fully fenced backyard with a screened-in pool enclosure and lanai, perfect for relaxing or entertaining year-round in true Florida style. This move-in-ready gem truly has it all. Don’t miss your opportunity—schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Tony Nicolas (630-514-9342)
2433 GRAND TETON CIR, WINTER PARK, FL 32792
$259,0006 Days on yellowkey MLS ID: O6427336
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1720 Built: 1981 Tax: $4,050 (2025)Community: Cedarwood Village 1Condo
Taxes:$4,050
Remarks: Welcome to 2433 Grand Teton Circle in the sought-after Cedarwood Village community of Winter Park, where move-in ready living, thoughtful updates, and an unbeatable location come together. Featuring the largest floor plan in the community, this spacious condo has been refreshed with brand-new carpet and fresh interior paint, offering a bright, inviting space that’s ready for its next owner. The highly desirable layout includes a first-floor primary suite, making everyday living both comfortable and convenient. Inside, you’ll love the soaring vaulted ceilings that create an open, airy feel, while the wood-burning fireplace serves as the focal point of the living room, adding warmth and character. Just off the primary suite, a private front patio provides the perfect place to enjoy your morning coffee or unwind in the evening. A dedicated storage room offers additional space for seasonal décor, bicycles, and outdoor equipment. Cedarwood Village is known for its low-maintenance lifestyle, with the HOA maintaining the grounds and completing roof and exterior paint replacements approximately five years ago. Residents also enjoy access to a community pool, clubhouse, tennis courts, pickleball courts and guest parking. Location is one of this home’s greatest features. Ideally situated near Downtown Winter Park, Park Avenue, Winter Park Village, Baldwin Park, Full Sail University, Rollins College, Valencia College, and the University of Central Florida (UCF), you’ll enjoy convenient access to some of Central Florida’s best shopping, dining, entertainment, and recreation. Commuting is easy with nearby Howell Branch Road, Semoran Boulevard (SR 436), Aloma Avenue (SR 426), 417, and I4, providing quick access to Downtown Orlando, Maitland, Lake Mary, AdventHealth Winter Park, and Orlando International Airport. Located within the Seminole County Public School district, this home offers both convenience and an exceptional Winter Park address. Whether you’re searching for a primary residence, a low-maintenance home, or a spacious Winter Park condo in one of Central Florida’s most convenient locations, 2433 Grand Teton Circle offers the perfect combination of space, comfort, and lifestyle.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alexis Jacobsen (407-900-0771)
4469 OLD BEAR RUN, WINTER PARK, FL 32792
$1,799,999170 Days on yellowkey MLS ID: O6375415
REDUCED by $50,001 (2.7%) on 05/22/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4288 Built: 1978 Tax: $10,710 (2024)Community: Pervis Survey For R ESpa: NoSingle Family
Taxes:$10,710
Remarks: Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom residence offers a rare combination of privacy, scale, and true Florida waterfront lifestyle. A circular driveway behind a private gate welcomes you to a thoughtfully renovated home designed to capture sweeping lake views. Bear Gully Lake is spring-fed and open to water vehicles, making it ideal for boating, water skiing, wakeboarding, tubing, fishing, and year-round enjoyment. The lakefront experience is exceptional, featuring a fully equipped dock with power, covered boat lift, and sun deck, perfectly positioned for enjoying stunning sunsets. Outdoor living is a highlight of the property. The expansive lanai and pool area overlook the lake and are ideal for entertaining, complete with a renovated summer kitchen featuring a grill, sink, mini refrigerator, and granite countertops. The oversized backyard provides ample space for gatherings, recreation, and pets. Inside, the home opens to a dramatic great room with vaulted ceilings, a striking stacked-stone feature wall with custom built-ins, and large sliding glass doors that fully retract to create seamless indoor-outdoor living. The space was reimagined during extensive renovations to maximize natural light and lake views. The chef’s kitchen, redesigned by award-winning designer Sandra Agurto of CCI, features all-wood cabinetry, quartz countertops, contemporary backsplash, oversized island with beverage and wine refrigerators, induction cooktop, convection ovens, and a separate full refrigerator and freezer, with abundant custom storage throughout. The primary suite is privately located in its own wing and offers serene lake views, high ceilings, and a spa-style en-suite bath renovated in 2022 with soaking tub, walk-in shower, expansive custom vanity, upgraded lighting, and private water closet with bidet. A large walk-in closet with custom built-ins completes the suite. All bedrooms feature their own bathrooms and walk-in closets, providing exceptional privacy and flexibility, with three full en-suite bedrooms ideal for guests or multigenerational living. Additional flexible spaces include a gym or bonus room suitable for formal living, dining, or a game room. Recent upgrades include a new roof (2018), new hot water heater (2024), fully fenced yard, Russound sound system, updated security system, new pool deck pavers, and a rebuilt dock with Trex decking and updated boat lift components. The home is part of a lake association with no mandatory dues, providing community updates and seasonal events such as the holiday boat parade. Conveniently located near SR-417, UCF, downtown Winter Park, and Trinity Prep, this is a rare opportunity to own a true spring-fed lakefront home on one of Winter Park’s most coveted lakes.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Keigan Lewis (305-393-8683)
2676 BARBADOS DR, WINTER PARK, FL 32792
$340,00061 Days on yellowkey MLS ID: O6411958
2 Days Off yellowkey (back on 6/26/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1743 Built: 1978Monthly Fee: $98 Tax: $4,131 (2025)Community: Windward Square Sec 2Townhouse
Taxes:$4,131
Elementary School: Eastbrook Elementary
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, 2-bathroom corner-unit townhome located in the heart of Winter Park. Offering 1,743 square feet of thoughtfully designed living space, this home combines comfort, style, and an unbeatable location just minutes from shopping, dining, parks, and top-rated schools. The desirable corner-unit placement provides added privacy, extra natural light, and a spacious feel throughout. Inside, you’ll find luxury vinyl plank flooring flowing seamlessly throughout the home and a stunning vaulted ceiling that creates an airy, open atmosphere in the living room. The beautifully updated kitchen is truly the centerpiece of the home, featuring gorgeous wood countertops, ample cabinet space, and an open-concept layout perfect for entertaining family and friends. Step outside to the rear screened-in patio and enjoy peaceful pond views in your own private outdoor retreat. Whether you’re sipping your morning coffee or unwinding after a long day, this tranquil space offers the perfect setting to relax and enjoy Florida living year-round. This exceptional Winter Park townhome is a rare opportunity you won’t want to miss.
Listing Agent: Joseph Sipp (407-820-7016)
2475 TAHOE CIR #2475, WINTER PARK, FL 32792
$278,0002 Days on yellowkey MLS ID: O6428082
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1295 Built: 1981Monthly Fee: $499 Tax: $2,246 (2025)Community: Cedarwood Village 1Condo
Taxes:$2,246
Remarks: Turnkey Living in the Heart of Winter Park! Welcome to this beautifully maintained 2-bedroom, 2-bath townhome offering the perfect blend of comfort, convenience, and low-maintenance living. Vacant and move-in ready, this home has been freshly painted and features a recently replaced air conditioning system, providing peace of mind for its next owner. Inside, you'll find a thoughtfully designed floor plan with spacious living and dining areas, a well-appointed kitchen, and two generously sized bedrooms and bathrooms designed for comfort and functionality. Whether you're relaxing at home or entertaining friends and family, this inviting layout makes everyday living effortless. Step outside and enjoy the exceptional community amenities, including a sparkling swimming pool and tennis courts, perfect for enjoying Florida's year-round sunshine. Whether you're a first-time homebuyer, downsizing, seeking a second home, or looking for an investment opportunity, this property offers incredible versatility. Ideally located in desirable Winter Park, you'll be just minutes from shopping, dining, entertainment, major highways, UCF, Full Sail University, Downtown Winter Park, and Downtown Orlando, making commuting and enjoying Central Florida's best attractions a breeze. Don't miss your opportunity to own this beautifully updated, turnkey home in one of Central Florida's most sought-after communities! All room measurements, HOA information, square footage, and property details are deemed reliable but not guaranteed and should be independently verified by the buyer and buyer's agent.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Sarah Doyer (386-490-7677)
4798 TANGERINE AVE #4798, WINTER PARK, FL 32792
$175,00055 Days on yellowkey MLS ID: S5150136
1 Days Off yellowkey (back on 7/28/2026)
REDUCED by $5,000 (2.8%) on 07/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1058 Built: 1973 Tax: $368 (2025)Community: Wrenwood CondoSpa: NoCondo
Taxes:$368
Remarks: Under contract-accepting backup offers. Welcome to this charming and well-maintained condominium located in the desirable Winter Park area, offering the perfect blend of comfort, convenience, and low-maintenance living. This inviting residence features a spacious and functional layout filled with natural light, creating a warm and welcoming atmosphere ideal for everyday living or entertaining. Enjoy an open living and dining area that flows seamlessly to a private screened porch with additional storage space, perfect for relaxing and enjoying the peaceful surroundings. The home offers generous room sizes, ample storage throughout, and a comfortable living environment within a quiet and established community. Residents enjoy access to community amenities including a sparkling swimming pool, fitness center, clubhouse/conference room, beautifully maintained grounds, and ample parking. HOA benefits may include exterior maintenance, landscaping, water, trash service, and roof maintenance, providing added convenience and value. Ideally situated in East Winter Park, this property offers exceptional access to everything Central Florida has to offer. Conveniently located just minutes from Full Sail University, the University of Central Florida (UCF), Rollins College, Downtown Winter Park, Baldwin Park, and Downtown Orlando. Enjoy nearby shopping, dining, entertainment, golf courses, parks, grocery stores, and everyday conveniences all within close proximity. Commuters will appreciate the easy access to major highways including SR-417 and SR-408, while Orlando International Airport is only a short drive away. Whether you are a first-time homebuyer, downsizing, investing, or searching for a centrally located primary residence, this home presents an outstanding opportunity to enjoy the Winter Park lifestyle in a peaceful and well-connected community.
Listing Agent: Vincenza Di Cesare De Vieira, Pa (407-680-8118)
3740 HAWTHORNE LN, WINTER PARK, FL 32792
$435,0002 Days on yellowkey MLS ID: O6428202
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1645 Built: 1979 Tax: $2,081 (2025)Community: Garden Lake Estates Unit 1Spa: YesSingle Family
Taxes:$2,081
Remarks: This is an Excellent split plan pool home. Tile floors in the Family room, Living Room, and Dining room keep with the Florida syle. The bedrooms feature wood floors in all the bedrooms.The screened in pool is also heated and has a Heated Spa. It is conveniently located in Seminole County with a Winter Park address. It also features a ROOF that is only two years old ! You can cool off in the screened in pool on hot days. During the cooler time of year you can use the Heater for both the pool and Spa.The screen enclosure helps to make the pool more inviting. You also have a covered porch area for entertaining. There is yard space that is fully fenced. The back yard also has a shed for storing your yard tools. SOLD AS IS. Contact the Listing Agent for a personal tour !
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: John Crea (407-754-6001)
3621 HAWTHORNE LN, WINTER PARK, FL 32792
$415,00023 Days on yellowkey MLS ID: S5153086
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1525 Built: 1979 Tax: $1,108 (2025)Community: Garden Lake Estates Unit 1Single Family
Taxes:$1,108
Elementary School: Evans Elementary
Remarks: Discover the perfect place to call home! This beautiful 4-bedroom, 2-bath residence offers a spacious layout, a 2-car garage, and the freedom of no HOA. Conveniently located near top-rated schools, shopping, dinning and major highways, it provides the ideal balance of comfort, convenience, and value. Whether you're a first time homebuyer or looking to upgrade, this home is an excellent opportunity you won't want to miss.
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Jimmy Claudio (407-552-8519)
1507 GOLFSIDE DR, WINTER PARK, FL 32792
$850,000118 Days on yellowkey MLS ID: O6395355
REDUCED by $49,000 (5.5%) on 07/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2003 Built: 1981 Tax: $2,783 (2025)Community: Greenview At Winter PinesSingle Family
Taxes:$2,783
Remarks: Virtually Staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring throughout. Updates include (but definitely not limited to) BRAND new kitchen with Stainless Steel Appliances, new cabinets & quartz countertops. Formal living & dining rooms PLUS Family room with vaulted ceilings featuring a new electric fireplace for amazing ambiance and sliding doors inviting you to new brick pavered 31x 11 screened porch overlooking newly refinished sparkling pool & golf course (no rear or side neighbors!!) Bedroom wing of home offers a large inside laundry room, beautiful guest/pool bath with dual sinks & shower/tub and 2 fresh guest bedrooms. THE PRIMARY SUITE has been thoughtfully remodeled with sliding doors to pool, AMAZING primary bath with oversized work-of-art shower with dual shower heads, dual vanity, separate water closet & HUGE walk-in closet! Extras include: NEW double paned windows & 3 sliding doors to pool/patio, crown molding, NEW roof November 2024, oversized 2 car garage, NEW landscaping, all NEW ceiling fans & light fixtures, NO HOA!! Zoned for Brookshire Elementary, Glenridge Middle & Winter Park High. WELCOME HOME!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Catherine D'Amico (407-252-3210)
2223 CONIFER AVE, WINTER PARK, FL 32792
$435,00016 Days on yellowkey MLS ID: O6424677
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1620 Built: 1970 Tax: $2,253 (2025)Community: Eastbrook Sub Unit 16Spa: NoSingle Family
Taxes:$2,253
Remarks: Virtually Staged. Welcome to 2223 Conifer Ave, recently enhanced with a new roof, fresh interior paint, and fresh exterior paint. The kitchen features all stainless steel appliances and an accent backsplash. A walk in closet is included in the primary bedroom, complemented by double sinks in the primary bathroom. Outside, an in ground pool and a covered patio in the back yard, all within a fenced in backyard. Perfectly updated and designed for comfort and enjoyment, this home awaits.. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
814 DENSMORE DR, WINTER PARK, FL 32792
$425,000104 Days on yellowkey MLS ID: O6399773
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1610 Built: 1960 Tax: $5,402 (2025)Community: Winter Park EstatesSingle Family
Taxes:$5,402
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Welcome to this charming home situated on a spacious lot in a quiet, established neighborhood in Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, expansive front yard, and peaceful setting that make this property feel like home. Inside, the home offers a light and open layout with a seamless flow between the living, dining, and kitchen spaces—perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, granite countertops, stainless steel appliances, and a functional layout with bar seating, making it both stylish and practical. The bedrooms are comfortably sized with great natural light, offering flexibility for family, guests, or a home office. The bathrooms have been thoughtfully updated, including a beautifully renovated shower with modern tilework that adds a fresh, clean feel. The Florida room in the back creates a relaxing space for drinking coffee or curling up for a family movie night. Step outside to a generously sized backyard with endless potential—whether you envision creating an outdoor entertaining space, adding a pool, or simply enjoying the open green space. With plenty of room to spread out, this yard offers the kind of flexibility that’s hard to find. Conveniently located near local shopping, dining, and major roadways, this home offers both comfort and accessibility. Zoned for great Winter Park schools. Whether you’re a first-time buyer, investor, or looking to downsize, this property presents an incredible opportunity to own a home with room to make it your own.
Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)
Listing Agent: Liz Jones (407-619-6345)
2833 PRINCE JOHN RD, WINTER PARK, FL 32792
$684,0007 Days on yellowkey MLS ID: O6427246
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1605 Built: 1963 Tax: $6,145 (2025)Community: Winter Park Pines RepSingle Family
Taxes:$6,145
Remarks: Virtually Staged. Welcome to a residence where timeless design meets modern sophistication in the highly sought-after Winter Park Pines community—one of Winter Park's most established neighborhoods, celebrated for its tree-lined streets, oversized homesites, exceptional schools, and proximity to world-class dining, shopping, golf, and cultural attractions. With no HOA, this thoughtfully renovated home offers the perfect balance of refined living and everyday comfort in one of Central Florida's most desirable locations. This 1,605 sqft, 4-bedroom, 2-bath residence, has been transformed with modern finishes, upgraded systems, and thoughtful design throughout. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a bright and inviting space ideal for both everyday living and entertaining. The interior features new luxury vinyl flooring in all main areas and fully remodeled bathrooms with floor and wall tile, elongated modern toilets, updated vanities, and premium finishes. The main bathroom includes a new bathtub, medicine cabinet, and mirror cabinet, while the master bathroom offers a glass-walled shower with a niche and a double floating vanity with mirrored cabinets. The kitchen is a true centerpiece, showcasing a large island, quartz countertops, high-end custom cabinetry with soft-close drawers, and a pantry with built-in shelving. Luxury FORNO white-and-gold appliances elevate the space, including an induction cooktop and range, hood fan, double-door refrigerator with ice maker, and a microwave built into an island drawer. The kitchen is completed with a high-end white sink bowl and garbage disposal, adding both style and functionality. Major improvements were completed with permits, including new HVAC (2026), new water heater (2026), new 200 Amps electrical panel (2026), and a full plumbing repipe (2026). Additional upgrades include new wired smoke alarms and new doors throughout. The living room features modern potlights, and all bedrooms include contemporary ceiling fans. The lanai has been renovated, offering a comfortable outdoor retreat. Exterior enhancements include an updated roof (2020), fresh interior and exterior paint, a refinished garage floor, and an upgraded garage door opener (2026). The property also features a brand-new irrigation system (2026) to keep the grounds lush and easy to maintain. Smart-home additions include a smart Blink doorbell and a smart front-door lock, providing added convenience and security. The spacious, fully-fenced backyard offers privacy and endless possibilities for outdoor enjoyment, gardening, or future enhancements. Perfectly positioned just minutes from Winter Park Pines Golf Club, Cady Way Trail, Park Avenue, Rollins College, AdventHealth Winter Park, and the boutiques, fine dining, and cafés that have made Winter Park one of Central Florida's most coveted destinations, you'll also enjoy convenient access to Downtown Orlando, Baldwin Park, major highways, Orlando International Airport, and countless entertainment venues. With meticulous renovations, modern systems, smart-home upgrades, and an unbeatable Winter Park Pines location, this home is truly move-in ready and prepared to welcome its next owner.
Listing is courtesy of: NETWORTH REALTY OF ORLANDO, LLC (321-329-3127)
Listing Agent: Wendy Aldana Llc (510-316-6968)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.