Location: Winter Park
Keyword(s): Tuskawilla Middle
Keyword(s) Middle School: Tuskawilla Middle
Do Not Show Listings
1605 PURITAN AVE, WINTER PARK, FL 32792
$399,00028 Days on yellowkey MLS ID: O6417098
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1285 Built: 1963 Tax: $3,605 (2025)Community: Eastbrook Sub Unit 06 2Nd RepSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,605
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: SELLER FINANCING. Stunning 3-bedroom, 2-bath remodeled home with no HOA, ideally located on the border of Winter Park and Orlando. This move-in-ready property features a new roof installed in July 2025, an updated kitchen with beautiful granite countertops and brand-new appliances. Enjoy the perfect combination of comfort, style, and convenience with easy access to shopping, dining, schools, and major roadways. Don't miss this one! Schedule your private showing right away!
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: Angelica Tomlinson Llc (407-222-8676)
5340 N LAKE BURKETT LN, WINTER PARK, FL 32792
$469,90040 Days on yellowkey MLS ID: O6413717
REDUCED by $5,100 (1.1%) on 07/14/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1746 Built: 1994Monthly Fee: $76 Tax: $1,591 (2025)Community: Trinity Bay Ph 2Spa: NoSingle Family
Taxes:$1,591
Remarks: Private Lake Access & Exceptional Florida Living! Welcome to Trinity Bay, a charming community offering deeded access to Lake Burkett, a private 75-acre spring-fed ski lake featuring navigable access to Lake Martha. Reserved primarily for neighborhood residents and their guests, this unique amenity provides an incredible opportunity to enjoy biking, boating, waterskiing, and lakeside recreation just moments from home. This meticulously maintained residence stands out with fresh exterior paint, updated landscaping, and inviting curb appeal. Inside, soaring vaulted ceilings and abundant natural light create an open, airy atmosphere, enhanced by fresh interior paint throughout. The thoughtfully designed split-bedroom floor plan makes excellent use of every square foot, offering comfortable living with no wasted space. An indoor laundry room, spacious 2-car garage, and desirable semi cul-de-sac location add to the home's appeal. Beyond the lake, residents enjoy a community pool, playground, boat launch, and dock along with being located directly across the street from the Cross-Seminole Bike Trail, creating a true lifestyle community. Conveniently located with easy access to SR 417, shopping, dining, and everyday essentials, this home offers the perfect blend of recreation, convenience, and value. Experience the rare opportunity to enjoy private lake-access living in one of the area's most desirable neighborhoods.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Tanya Mcdonnell (407-625-2719)
1914 BONANZA CT, WINTER PARK, FL 32792
$429,99961 Days on yellowkey MLS ID: O6408461
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1727 Built: 1968 Tax: $4,497 (2025)Community: Eastbrook Sub Unit 13Single Family
Taxes:$4,497
Remarks: Welcome to your winter Park retreat! Step into this beautifully renovated 3 bedroom, 2 bathroom home where modern meets timeless comfort. Designed with an open floor plan, the living space flows seamlessly, making it perfect for both entertaining and everyday living. The brand new kitchen shines with contemporary finishes, while the new flooring throughout the home adds warmth and style. Both bathrooms have been thoughtfully renovated, offering a clean and modern feel. The Florida room, wrapped in huge windows. floods the home with natural light, creating a bright and inviting space you'll love year round. Step outside to enjoy a covered patio, ideal for morning coffee or relaxing evenings with friends and family. With its prime location, this home is a blend of convenience, charm, and modern living ready for you to make it your own. Call and schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Judy Julien, Pa (407-234-4051)
1564 LAWNDALE CIR, WINTER PARK, FL 32792
$450,00022 Days on yellowkey 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
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)
1418 LONE FEATHER TRL, WINTER PARK, FL 32792
$750,00029 Days on yellowkey MLS ID: O6417341
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2197 Built: 2022Monthly Fee: $244 Tax: $6,224 (2025)Community: Landings At Hawks CrestSingle Family
Taxes:$6,224
Remarks: Nestled within the gated community of Hawks Crest, this beautifully appointed two-story residence offers a sophisticated blend of timeless design, modern comfort, and effortless Florida living. Thoughtfully designed and meticulously maintained, the home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes, and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage, and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office, or fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee, or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic walking trails, and private access to Lake Howell. The community is also conveniently located near local favorites including Kelly's Ice Cream, Foxtail Coffee, and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining, and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Harif Hazera Llc (407-953-9098)
4469 OLD BEAR RUN, WINTER PARK, FL 32792
$1,799,999156 Days on yellowkey MLS ID: O6375415
0 Days Off yellowkey (back on 7/14/2026)
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
Elementary School: Red Bug Elementary
Tax Year: 2024
Remarks: Under contract-accepting backup offers. 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)
1320 GLADIOLAS DR, WINTER PARK, FL 32792
$475,00047 Days on yellowkey MLS ID: O6412139
REDUCED by $5,000 (1.0%) on 06/15/2026
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)
2087 LAURELWOOD WAY, WINTER PARK, FL 32792
$625,00034 Days on yellowkey MLS ID: O6415387
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1920 Built: 2019Monthly Fee: $244 Tax: $4,970 (2025)Community: Hawks CrestSingle Family
Taxes:$4,970
Remarks: Nestled within the gated community of Hawks Crest, this thoughtfully designed single-story residence offers an exceptional blend of comfort, style and convenience in the heart of Winter Park. Spanning 1,920 square feet, this home features an open-concept floor plan that seamlessly connects the living, dining and kitchen areas, creating an inviting setting for both everyday living and entertaining. The kitchen serves as the centerpiece of the home, appointed with granite countertops, stainless steel appliances and a spacious center island with seating. The private owner's suite offers a walk-in closet and a well-appointed bath, while three additional bedrooms provide flexibility for guests, a home office or evolving lifestyle needs. A covered lanai overlooks the tranquil pond, creating the perfect backdrop for outdoor relaxation and year-round Florida living. Residents of Hawks Crest enjoy access to an impressive collection of amenities, including a clubhouse, fitness center, resort-style pool, splash pad, dog park, playgrounds, virtual guard gate and private access to Lake Howell for kayaking and paddleboarding. Ideally located just minutes from highways, Park Avenue, downtown Maitland, top-rated schools, Foxtail Coffee and Kelly's Ice Cream, this residence offers the opportunity to enjoy one of Winter Park's most sought-after gated communities.
1840 ASTER DR, WINTER PARK, FL 32792
$419,90044 Days on yellowkey MLS ID: O6412364
REDUCED by $10,090 (2.3%) on 07/09/2026
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
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)
2651 CAYMAN WAY, WINTER PARK, FL 32792
$255,000176 Days on yellowkey MLS ID: O6375086
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1020 Built: 1978Monthly Fee: $99 Tax: $3,553 (2024)Community: Windward Square Sec 2Townhouse
Taxes:$3,553
Remarks: Virtually Staged. ALL PLAY and NO WORK! Imagine coming home to a space where weekends are made for relaxing, entertaining, and enjoying the best of Florida living. This single-story, two-bedroom, two-bath townhome offers an effortless lifestyle in a location that puts everything within reach. Vaulted ceilings create an open, airy feel in the spacious living and dining area, while sliding glass doors lead to a private, fenced backyard with a large concrete patio?perfect for morning coffee, weekend barbecues, or unwinding after a long day. With no rear neighbors and views of the community green space, you?ll enjoy added privacy and tranquility. The kitchen is designed for everyday ease, featuring ample cabinetry, a breakfast bar, and all appliances included, making move-in simple. Retreat to the oversized primary suite with a walk-in closet and direct patio access, creating a true indoor-outdoor flow. The second bedroom offers flexibility for guests, a home office, or creative space. Step outside your front door and enjoy resort-style amenities, including three swimming pools, tennis courts, a clubhouse, and a playground—all with low HOA fees. With parking for three vehicles, convenience is built right in. Located close to shopping, dining, major roadways, and just minutes from Winter Park’s Park Avenue, this home delivers both comfort and connection. Owner-occupant only community—ideal for those looking to put down roots and enjoy a true neighborhood feel. Live more. Maintain less. Welcome home.
Listing Agent: Kyle Clark (407-921-3287)
2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792
$245,00086 Days on yellowkey MLS ID: O6400674
REDUCED by $5,000 (2.0%) on 07/11/2026
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
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 $5,000 Buyer credit at closing toward a new AC and Water Heater. 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)
3463 ARNEL DR, WINTER PARK, FL 32792
$414,900120 Days on yellowkey MLS ID: O6390301
REDUCED by $5,000 (1.2%) on 07/02/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1770 Built: 1967 Tax: $4,648 (2024)Community: Eastbrook Sub Unit 11Single Family
Taxes:$4,648
Remarks: One or more photo(s) has been virtually staged. Pool Home *No HOA *Paid-Off Solar Panels **Roof (2018) Welcome to this well-maintained 3-bedroom, 2-bathroom home offering approximately 1,770 square feet, a 2-car garage, private pool, Roof (2018), Water Heater (2019), and fully paid-off solar panels for added energy savings. The renovated kitchen features quartz countertops, stainless steel appliances, modern cabinetry, an oversized island with an induction cooktop, and an open layout that flows into the main living areas. The spacious Florida Room is one of the home's highlights, featuring soaring wood ceilings, exposed beams, a built-in serving area, and direct access to the pool. It's a great space to relax, entertain, enjoy your morning coffee, or watch the big game. The primary suite offers a flexible bonus area that can be used as a reading nook, home office, vanity, workout space, or additional storage. The primary bathroom also has direct access to the pool. Step outside and enjoy a backyard that's hard to find in many pool homes. In addition to the private pool, you'll still have green space to enjoy, plus a barbecue connection already in place for outdoor cooking. Whether you're hosting friends, grilling on the weekend, or simply unwinding by the pool after work, this backyard is ready to enjoy. Conveniently located just minutes from Park Avenue, Rollins College, Full Sail University, UCF, shopping, dining, and major highways. Zoned for highly rated Seminole County schools.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
1956 JAPONICA RD, WINTER PARK, FL 32792
$549,00014 Days on yellowkey MLS ID: O6421731
0 Days Off yellowkey (back on 7/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1923 Built: 1972Monthly Fee: $2 Tax: $4,849 (2025)Community: Winter WoodsSingle Family
Taxes:$4,849
Remarks: Welcome home to this beautifully updated 3-bedroom, 2-bath move-in ready home living on a spacious quarter-acre lot in one of Winter Park’s established neighborhoods. From the moment you arrive, you’ll appreciate the home’s inviting curb appeal with refreshed landscaping, and gutters. Inside, the open, light-filled layout features luxury vinyl plank flooring and tile throughout, creating a cohesive and modern feel that’s both beautiful and easy to maintain.The heart of the home is the thoughtfully renovated kitchen, complete with quartz countertops, soft-close cabinetry, Whirlpool and KitchenAid stainless steel appliances - including an induction stove top and double ovens. Major home features have recently been updated giving buyers confidence and peace of mind. The roof was replaced in 2020, the HVAC system in 2023, the water heater in 2019, and windows plus the sliding glass door were replaced in 2025 to improve energy efficiency and comfort. Step outside to your own private backyard retreat. The fully fenced yard offers exceptional space for pets, play, gardening, or even a future pool. An oversized extended paver patio creates the perfect setting for outdoor dining, entertaining friends, or simply relaxing on a Florida evening.
Listing is courtesy of: PROPLOGIK REALTY INC (407-658-8566)
Listing Agent: Marcos Marchena (407-658-8566)
5781 SHALE CT, WINTER PARK, FL 32792
$320,0009 Days on yellowkey MLS ID: O6422583
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1086 Built: 1985Monthly Fee: $69 Tax: $2,096 (2025)Community: Aloma ParkSpa: NoHalf Duplex
Taxes:$2,096
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 5781 Shale Court in Winter Park, a 2-bedroom, 2-bath home designed for comfortable everyday living. This one-story residence offers a practical layout with space for relaxing, dining, and hosting guests. The two-bedroom configuration provides flexibility for residents, visitors, a home office, or a hobby room, while two full bathrooms add convenience for daily routines. Outdoor living includes a covered and screened patio, creating a comfortable space to enjoy fresh air, outdoor dining, or quiet downtime while staying shaded and protected from the elements. Located in Winter Park, the home is close to shopping, dining, parks, schools, and everyday conveniences. The area offers access to nearby destinations such as Winter Park Village, Park Avenue, local recreation, and major roadways connecting to Maitland, Orlando, and surrounding Central Florida communities.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
1189 LAZY HOLLOW PL, WINTER PARK, FL 32792
$450,00012 Days on yellowkey MLS ID: O6422142
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1525 Built: 1984 Tax: $2,369 (2025)Community: SpringviewSingle Family
Taxes:$2,369
Remarks: Welcome to your own private backyard oasis in the heart of Winter Park! This beautifully maintained two-story home offers 4 bedrooms, 2 bathrooms, and the perfect blend of comfort, style, and outdoor living. With no HOA, a fully fenced backyard, and a sparkling pool, this home delivers the Florida lifestyle buyers have been searching for. From the moment you arrive, you'll appreciate the pride of ownership throughout. The home features a 2022 metal roof, 2021 gutters, 2020 insulation, a 2019 A/C, and a new garage door and opener installed in 2023, giving buyers peace of mind for years to come. Inside, the home has been refreshed with fresh interior paint, updated door hardware throughout, updated kitchen hardware, and tasteful finishes that create a bright and welcoming atmosphere. Just beyond the living spaces, the screened patio provides the perfect transition to your backyard oasis. The backyard is truly the highlight of the home, featuring a pool resurfaced in 2024, a replaced pool pump motor, an expansive patio, a pergola, and a built-in sound system that conveys with the home, creating the perfect setting for relaxing or entertaining family and friends. The generous, fully fenced backyard offers plenty of space for pets, play, gardening, and enjoying the outdoors. Move-in ready and loaded with valuable updates, this exceptional Winter Park pool home offers comfort, functionality, and an unbeatable outdoor lifestyle. Conveniently located near shopping, dining, parks, and major roadways, this is one you won't want to miss!
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Simi Lakhani (407-408-7393)
2521 GALLIANO CIR, WINTER PARK, FL 32792
$360,00021 Days on yellowkey MLS ID: O6419329
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1682 Built: 2003Monthly Fee: $175 Tax: $4,532 (2025)Community: Vistas At Lake HowellTownhouse
Taxes:$4,532
Elementary School: Sterling Park Elementary
Remarks: Welcome to this beautifully maintained townhome located in the heart of Winter Park, Florida. From the moment you arrive, the charming exterior draws you in with its classic stucco finish, attached one-car garage, manicured landscaping, and a welcoming shaded entry framing the front door. Step inside to an inviting foyer featuring high ceilings, modern lighting, and a striking staircase that sets a stylish tone for the rest of the home. The main level transitions into an expansive, light-filled open concept floor plan seamlessly connecting the living room, dining area, and kitchen. Rich wood-look LVP flooring runs throughout the entire lower level, perfectly complementing the crisp neutral walls and providing a cohesive, contemporary aesthetic. The spacious living and dining areas offer an exceptional layout for both daily living and effortless entertaining. Large sliding glass doors at the rear of the home flood the living space with natural light and open directly to a private, screened-in back patio, making it easy to enjoy the Florida breeze. Overlooking the dining area is a spacious kitchen, which features a half-wall cutout that keeps the chef connected to the conversation. Equipped with plenty of warm wood cabinetry, neutral countertops, a deep double sink, and a suite of white appliances, this kitchen is as ample as it is welcoming. A convenient guest half-bathroom with a pedestal sink completes the well-designed ground floor layout. Head upstairs to discover the private living quarters, where the beautiful wood-look flooring continues through the hallway and into each spacious bedroom. The expansive primary suite serves as a true retreat, boasting high vaulted ceilings, an elegant modern ceiling fan, a massive walk-in closet with built-in wire shelving, and a trio of large windows that fill the space with cheerful morning light. This main bedroom easily accommodates king-sized furniture and offers the luxury of an attached en-suite bathroom with dual sinks. The additional bedrooms are equally impressive, each featuring soaring vaulted ceilings, updated stylish ceiling fans, and generous closet space near the dedicated upper-level laundry closet, which comes equipped with a washer and dryer. The outdoor and utility spaces add tremendous value and convenience to this efficient property. The attached garage features an open, clean layout perfect for secure parking, extra storage, or a small home workshop area. At the back of the home, the deep screened-in patio is an ideal spot for outdoor dining, grilling, or relaxing in the shade. The patio steps out onto a beautiful community green belt with pristine lawns and mature shade trees, offering a peaceful residential backdrop. Nestled in a premium, tree-lined enclave, the community boasts pristine, winding roads, manicured privacy hedges, and a scenic retention pond complete with a flowing water fountain feature. This idyllic neighborhood setting perfectly balances the tranquility of nature with outstanding proximity to nearby lakes, parks, major roadways, and local shopping centers. Don't miss the opportunity to own this pristine, move-in ready retreat in one of Central Florida's most highly sought-after locations.
Listing is courtesy of: LPT REALTY LLC (386-388-7877)
Listing Agent: Daniel Lennon (954-483-9760)
283 LEWFIELD CIR #283, WINTER PARK, FL 32792
$142,50013 Days on yellowkey MLS ID: O6420915
1 Days Off yellowkey (back on 7/12/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973 Tax: $1,729 (2025)Community: Stratford A Winter Park CondoCondo
Taxes:$1,729
Remarks: Under contract-accepting backup offers. Seller may consider buyer concessions if made in an offer ~ Recently UPDATED and ready for its next owner, this light-filled FIRST FLOOR condo unit offers LOW MAINTENANCE LIVING in the desirable Stratford community of Winter Park – with a monthly HOA that's lower than many comparable communities! Step inside through the semi-private INTERIOR ENTRY to an OPEN CONCEPT floor plan featuring updated bathroom finishes, WOOD LAMINATE & TILE FLOORING throughout, and a spacious living and dining area designed for everyday comfort and easy entertaining. The kitchen is equipped with STAINLESS STEEL APPLIANCES, breakfast bar seating, and a seamless connection to the main living spaces. A convenient IN-UNIT LAUNDRY closet adds to the home's functionality, while sliding glass doors lead out to a SCREENED LANAI overlooking a large green space for the perfect spot to enjoy your morning coffee or unwind at the end of the day. Stratford is a beautifully maintained community offering a park-like setting complete with a COMMUNITY POOL and peaceful surroundings thanks to the mature trees, making it easy to enjoy the Florida lifestyle without the upkeep of a single-family home. Ideally located at the corner of Lake Howell Road and Howell Branch Road with quick access to SR 436, you will appreciate being just minutes from abundant shopping, dining, medical services, parks, and everyday conveniences. Whether you are searching for your first home, a seasonal retreat, or an investment opportunity, this well-maintained Winter Park condo is one you won't want to miss. Call today to schedule a tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
1540 FLORENTINO LN, WINTER PARK, FL 32792
$315,00053 Days on yellowkey MLS ID: O6408841
REDUCED by $20,000 (6.0%) on 07/12/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1682 Built: 2004Monthly Fee: $175 Tax: $5,340 (2025)Community: Vistas At Lake HowellTownhouse
Taxes:$5,340
Remarks: Come and see your new home in the sought after Vistas at Howell Branch community. This two story townhouse has 3 bedrooms, 2.5 baths, and open first floor, floor plan. Relax in the evening on your screened in porch. The master bedroom has a walk in closet and large master bath. Your washer and dryer are on the second floor centrally located to all the bedrooms. You will find yourself within walking distance of restaurants, grocery stores, and other retail outlets. It's central location puts within minutes of 436 and 417. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Ashley Fisak (407-848-7975)
2008 HOUNDSLAKE DR, WINTER PARK, FL 32792
$515,00030 Days on yellowkey MLS ID: O6414369
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2250 Built: 1980 Tax: $5,253 (2025)Community: Cedar RidgeSingle Family
Taxes:$5,253
Remarks: Virtually Staged. Discover space, comfort, and flexibility in this beautifully updated 4-bedroom, 2-bath home in the highly desirable Cedar Ridge community of Winter Park with no HOA. Offering approximately 2,250 square feet of living space, this home also features a versatile flex room ideal as a nursery, home office, guest suite, media room, or private retreat. The 2025 remodeled kitchen offers abundant cabinetry and pantry storage, while the renovated bathrooms feature stylish, modern finishes. Ceramic tile flows throughout most of the home, with warm wood-look flooring in three bedrooms for added comfort. Enjoy peace of mind with major improvements already completed, including a 2024 roof, 2023 whole-home replumbing, and 2023 electrical panel replacement with generator hookup. These significant updates allow you to focus on enjoying your new home instead of tackling major projects. Step outside to an oversized, fully fenced backyard shaded by two magnificent mature oak trees, creating a private setting for relaxing, entertaining, or family gatherings. A side-entry two-car garage adds both curb appeal and everyday convenience. Conveniently located just minutes from Baldwin Park, UCF, shopping, dining, parks, and Seminole County schools, this Cedar Ridge home offers exceptional space, recent major updates, and the convenience of an established Winter Park neighborhood with no HOA.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Nicholas Feinsod (407-607-7485)
1090 WILDMEADOW RUN, WINTER PARK, FL 32792
$835,000110 Days on yellowkey MLS ID: O6394208
REDUCED by $10,000 (1.2%) on 06/02/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2589 Built: 2021Monthly Fee: $243 Tax: $6,258 (2024)Community: Hawks CrestSingle Family
Taxes:$6,258
Remarks: Virtually Staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of electricity. Ask to see the bill. The premium solar system is PAID OFF with a TRANSFERABLE WARRANTY by manufacturer. This off-grid solar system comes with a WHOLE HOUSE BATTERY BACKUP, keeping your lights on when the power goes out. This home already comes wired for electric vehicles with room to expand. Excess power generated is sold back to the power company through the NET METERING program, resulting in credits back to the owners at the end of the year. The solar system also has two power monitoring systems for tracking your energy usage & production, conveniently controlled by your phone and computer. Hawks Crest is your home to community, where residents enjoy gated access into a landscaped resort atmosphere, featuring water fountains throughout, with an abundance of amenities. The clubhouse features a resort pool & kiddie pool, a fitness center, with sidewalks & playgrounds, along with the community’s private dock access to Lake Howell with a canoe/kayak launch. Now imagine, relaxing and enjoying park and pond views from your expansive lanai, soaking in the serene sunsets & manicured landscaping, all from the comfort of your spacious, 4-bedroom 3.5 bath home, conveniently located just a short distance from the resort clubhouse. Owners can relax and unwind while management handles all landscaping around your home, truly providing you a maintenance-free living lifestyle. Additional upgrades with this home include, commercial grade luxurious vinyl wide-plank flooring, two power monitoring systems, a whole-house water softener & filter system, and two HVAC units, all designed for comfort, convenience, and a very clean home, where you can relax. Nestled in this spacious home, you’ll find 20-foot-high ceilings with awe-inspiring views of the illuminated pond fountain, creating a serene view & relaxing atmosphere you’ll enjoy, even from the kitchen sink. Your chandelier can be lowered 20-feet to the floor for easy maintenance & cleaning, using a winch lift system in the attic.(Rated up to 200 lbs). And even watch the rockets launch at The Cape from the front yard. Uniquely designed, this home was built to withstand extreme weather, featuring a concrete/granite tile roofing system, steel reinforcement, concrete-filled block walls & slab, all anchoring to the foundation, uniquely tying everything together. Meticulously maintained by the owners, this home comes with a complete set of blueprints, along with many photos & videos taken of the home during the building process. Owners even have documents for all equipment & appliances. And the premium solar system comes with a transferable warranty that will keep the lights on when the power is out. This home features a split floor-plan, with a primary bedroom on both the first and second floors. Spanning 2,589 sq.ft., this home offers an additional 540 sq.ft. of screened-in lanai, providing a private outdoor oasis where you’ll find owners enjoying the tranquility of Florida sunsets. Schedule a showing for your buyers today! And…***Remember to see the list of the owners’ upgrades***.
Listing is courtesy of: BHHS FLORIDA REALTY (352-729-7325)
Listing Agent: Rod Chevalier (352-729-1818)
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