Displaying: For Sale
Location: Winter Garden
Property Type(s): Single Family
Price: $500,000 to $599,000
Do Not Show Listings
Winter Garden - 164 properties found
113 W DIVISION ST, WINTER GARDEN, FL 34787
$525,99057 Days on yellowkey MLS ID: S5148787
REDUCED by $13,910 (2.6%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1487 Built: 1951 Tax: $4,920 (2025)Community: Winter Garden Shores RepSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,920
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome a beautifully remodeled Winter Garden home that seamlessly blends classic charm with modern upgrades! step inside to discover an open-concept kitchen, top appliances, quartz countertops, sleek modern bathrooms, new windows, and durable waterproof laminate floors, excellent screen porch. Perfect for everyday living and entertaining alike. New windows flood the interior with natural light, while luxury flooring flows throughout for effortless style and maintenance. This inviting 4-bed, 2-bath residence offers 1,487 sq ft of thoughtfully reimagined living space on a generous 0.17-acre lot in the desirable Winter Garden Shores neighborhood. Relax in sleek, modern bathrooms and enjoy the lush Florida weather from your excellent screened porch, ideal for morning coffee or evening gatherings. The home also includes an attached garage and has been upgraded with central air and updated finishes throughout. Located just moments from top schools, City Hall, dining, parks, and major commute routes, this home offers convenience without compromising. Whether you’re a growing family, first-time buyer, or relocating to the area, this Winter Garden gem is not to be missed! Owner offering 5k to closing cost..
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Marcelo Garrido (321-502-4448)
503 FIRST CAPE CORAL DR, WINTER GARDEN, FL 34787
$556,00099 Days on yellowkey MLS ID: O6381166
1 Days Off yellowkey (back on 6/16/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2365 Built: 2006Monthly Fee: $123 Tax: $3,974 (2024)Community: Black Lake Park Ph 01Single Family
Taxes:$3,974
Elementary School: SunRidge Elementary
High School: West Orange High
Tax Year: 2024
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. PRICE IMPROVEMENT!! Set within a gated community, Black Lake Park, just moments from Winter Garden Village - This beautifully maintained corner-lot residence offers a rare blend of everyday convenience and true lake-life access. A standout feature of the community is the PRIVATE BOAT RAMP and dedicated boat parking, providing direct entry to Black Lake — an exceptional amenity seldom found so close to town. The home itself has been thoughtfully cared for and updated, featuring a 2022 roof, fully fenced backyard, and an open, airy floor plan designed for both comfort and entertaining. High ceilings enhance the sense of space, while the primary suite serves as a private retreat with two walk-in closets and generous proportions throughout. Ideally located near top local restaurants, shopping, and entertainment, this home is just a five-minute drive to historic Plant Street in downtown Winter Garden and offers easy access to major highways for a seamless commute. Whether enjoying waterfront weekends, dining out nearby, or relaxing at home, this property delivers a lifestyle that is as convenient as it is distinctive.
Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)
Listing Agent: Heather Spirazza (407-757-6022)
15336 FIRELIGHT DR, WINTER GARDEN, FL 34787
$585,00014 Days on yellowkey MLS ID: G5113550
0 Days Off yellowkey (back on 6/15/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2242 Built: 2007Monthly Fee: $167 Tax: $4,649 (2025)Community: Belle Meade Ph 2Single Family
Taxes:$4,649
Elementary School: Whispering Oak Elem
Remarks: Under contract-accepting backup offers. Welcome to 15336 Firelight Drive, located in the highly desirable gated community of Belle Meade in Winter Garden. Situated directly across from the lake, this beautifully maintained 4-bedroom, 3-bathroom home with a 3-car garage offers a spacious split-bedroom floor plan designed for both comfort and privacy. Inside, you'll find wood flooring, elegant architectural details, and a well-appointed kitchen featuring granite countertops, solid wood cabinetry, stainless steel appliances, a pantry, and a breakfast nook. The spacious primary suite includes dual walk-in closets, French doors leading to the screened lanai, and a spa-inspired bathroom with a garden tub, separate shower, and dual vanities. Major updates include a NEW ROOF installed in 2023 and a BRAND NEW HVAC system installed in June 2026, providing valuable peace of mind for the next owner. Conveniently located just minutes from Winter Garden Village, Highway 429, shopping, dining, and top-rated schools, this home offers the perfect combination of location, functionality, and lifestyle. Schedule your private showing today.
Listing is courtesy of: BRAZA HOMES (352-978-6993)
Listing Agent: Lucas Barbosa Santos (352-978-6993)
16153 WATER SPRING BLVD, WINTER GARDEN, FL 34787
$549,990111 Days on yellowkey MLS ID: O6387508
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2042 Built: 2020Monthly Fee: $108 Tax: $6,865 (2024)Community: Storey Grove Ph 2Single Family
Taxes:$6,865
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: Single Family bungalow, 4 bedrooms and 3 full bathrooms, with backyard is rare. Designed for comfort and modern living, this property offers no carpet throughout, creating a clean and elegant look with luxury vinyl plank flooring. All pictures are real, no virtual staging or AI. The home includes a dedicated office space, thoughtfully designed and decorated, perfect for working from home. Enjoy the stylish TV/family room with a stunning wood slat accent wall and LED lights, adding warmth and sophistication to the space. Additional upgrades include a whole-house water filtration system and solar panels with a payment of less than $99 per month, helping reduce energy costs and increase efficiency. The community offers excellent amenities, including a resort-style pool, fitness center, basketball court, playground, and clubhouse for residents to enjoy. Ideally located next to top-rated schools, this home allows children to walk to school, making daily routines easier and safer. The property also sits on a premium lot adjacent to a walking path, providing additional privacy and open space. This is a fantastic opportunity to own a beautiful home in a highly desirable community.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Rodrigo Khoury Francisco (407-308-6489)
1049 SPRING LANDING DR, WINTER GARDEN, FL 34787
$547,90013 Days on yellowkey MLS ID: O6412927
1 Days Off yellowkey (back on 6/15/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2167 Built: 1990Monthly Fee: $25 Tax: $5,582 (2025)Community: Crown Point SpgsSingle Family
Taxes:$5,582
Elementary School: Dillard Street Elem
High School: Ocoee High
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. Beautifully updated and move in ready, this Winter Garden home combines modern updates with generous living space and a convenient location. The sellers have completely remodeled the interior, creating a fresh and inviting atmosphere throughout. The updated kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and an open layout that flows seamlessly into the main living areas. One of the standout features of the home is the spacious game room and enclosed screened porch, providing flexible space for entertaining, hobbies, gatherings, or simply enjoying views of the backyard year round. Large windows bring in natural light and create a bright, welcoming environment throughout the home. Recent major improvements offer added peace of mind, including a brand new roof, new water heater, and updated landscaping completed in February 2026. The generously sized yard provides room to enjoy the outdoors while mature trees add character and shade. Located in the heart of Winter Garden, this property offers convenient access to historic downtown Winter Garden, the West Orange Trail, shopping, dining, parks, and major roadways for an easy commute throughout Central Florida. This is an excellent opportunity to own a thoughtfully updated home in one of the area's most desirable locations.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Liza Farzati (561-385-8271)
16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787
$560,000202 Days on yellowkey MLS ID: O6365057
0 Days Off yellowkey (back on 5/22/2026)
REDUCED by $5,000 (0.9%) on 05/12/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2477 Built: 2018Monthly Fee: $245 Tax: $8,615 (2025)Community: Waterleigh Ph 2ASingle Family
Taxes:$8,615
Remarks: Lock in a guaranteed 5.625% interest rate through our preferred lender and make your move. Priced to sell, this beautifully maintained 2018-built Clearden model in the highly desirable Waterleigh community is ready for its next owner. Offering 2,477 sq ft, 4 bedrooms, and 3.5 bathrooms, this home is move-in ready with major updates already done. The open-concept main floor features a chef-ready kitchen with granite countertops, wood cabinetry, and stainless steel appliances, flowing into spacious living and dining areas with soaring ceilings. Tile flooring runs throughout the first floor, and a covered paver patio extends your living space outdoors. A first-floor bedroom with en suite bathroom and walk-in closet adds flexibility for guests, in-laws, or a home office. Upstairs, fresh interior paint (2024), new carpet (2024), and a 15x10 loft deliver comfort and versatility. Two secondary bedrooms share a dual-sink bath, while the primary suite features a spa-style bathroom with dual sinks and an oversized walk-in closet. A separate upstairs laundry room completes the level. Additional highlights include a freshly painted exterior, energy-efficient dual-pane windows, HOA-maintained landscaping, and a 2-year home warranty conveying at closing. Resort-style community amenities pools, clubhouse, and parks all just minutes from Walt Disney World. With a rate this low already secured, the only thing left to do is schedule your showing.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jeanine Louis, Llc (407-595-8634)
6279 SUNNY TIME AVENUE, WINTER GARDEN, FL 34787
$546,49026 Days on yellowkey MLS ID: O6412141
2 Days Off yellowkey (back on 6/14/2026)
REDUCED by $15,500 (2.8%) on 06/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1913 Built: 2026Monthly Fee: $152 Tax: $1,372 (2024)Community: Silverleaf OaksSpa: NoSingle Family
Taxes:$1,372
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: Under Construction. Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! Introducing the Haddock bungalow, a brand-new home that combines modern design and ultimate comfort. This home includes 3 spacious bedrooms, 2 full bathrooms, a powder room, a loft, a covered lanai, and a 2-car rear-load detached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. The kitchen boasts a large center island, a convenient storage pantry, and Whirlpool stainless steel appliances—including a vented microwave. Elkins white cabinetry, a decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room and coat closet. Upstairs, you’ll find the private owner’s suite and en suite bathroom, two spare bedrooms, a second full bathroom, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a glass-enclosed shower, quartz-topped dual vanity, private water closet, and linen closet. Throughout the entire first floor, bathrooms, and laundry room enjoy the beauty and convenience of ceramic tile. Plush, stain-resistant Shaw carpet covers the stairs, loft, and bedrooms, adding comfort and style. Smart home features include a smart thermostat, a smart doorbell, and LED downlights—ensuring your home is as connected as it is stunning. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.
Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)
Listing Agent: Adrienne Escott (407-250-9131)
5960 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$597,99644 Days on yellowkey MLS ID: G5112227
INCREASED by $40,873 (7.3%) on 06/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1772 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Taxes:$0
Remarks: Virtually Staged. Under Construction. Welcome to this beautifully designed newer-construction, the Amelia, a charming single-story bungalow in the highly sought-after Avalon Woods community of Winter Garden! Built in 2026, this spacious residence offers modern finishes, an open-concept layout, and a prime location just minutes from Hamlin Town Center, shopping, dining, top-rated schools, and major highways. Inside, you’ll find a bright and inviting floor plan featuring a large kitchen with upgraded cabinetry, stainless steel appliances, stone countertops, and an oversized island overlooking the main living and dining areas — perfect for entertaining. The spacious primary suite offers a private retreat with a walk-in closet and a well-appointed bathroom with dual vanities and a large walk-in shower.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
921 BENDING OAK TRL, WINTER GARDEN, FL 34787
$549,90047 Days on yellowkey MLS ID: O6405328
REDUCED by $20,000 (3.5%) on 06/11/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2517 Built: 2012Monthly Fee: $125 Tax: $3,791 (2025)Community: Oaks/Brandy Lake 01 Rep A & BSingle Family
Taxes:$3,791
Elementary School: Tildenville Elem
Remarks: Virtually Staged. Welcome home to 921 Bending Oak Trail in highly sought-after, downtown, golf cart district of Winter Garden! This spacious 4-bedroom, 2.5-bath home is perfectly situated on a private oversized corner lot with serene pond views, offering both privacy and a peaceful backdrop. The thoughtfully designed layout features a first-floor primary suite and convenient downstairs laundry room. The main living areas showcase updated modern, stone-like tile flooring, while the kitchen offers a large walk-in pantry that extends under the staircase for exceptional storage. The spacious Living Room and covered patio are wired for a surround sound system and have beautiful water views from the windows and paver patio. Upstairs, you’ll find generously sized secondary bedrooms, including one with an oversized walk-in closet, along with a large loft ideal for a home office, playroom, or flex space, all featuring engineered hardwood flooring. Enjoy outdoor living with a spacious entertaining area and the added benefit of a rear-entry garage accessed through a private, owners-only alleyway where you can also enter the home without climbing any stairs. Major updates include a roof replacement in 2025, making this home as practical as it is beautiful. Lastly, the location is incredible, the neighborhood is extremely well maintained, offering a tranquil walking community around Brandy Lake and duck filled ponds, a sparkling community pool, entertaining pavilion, community greenspace, and perfect playground for the little ones.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Claire Sims Llc (203-767-8109)
15073 VALVERSE ALY, WINTER GARDEN, FL 34787
$515,00013 Days on yellowkey MLS ID: O6416182
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1892 Built: 2017Monthly Fee: $339 Tax: $4,172 (2025)Community: Overlook 2/Hamlin Ph 2 & 5Single Family
Taxes:$4,172
Elementary School: Independence Elementary
Middle School: Bridgewater Middle
Remarks: Beautiful home in The Cove at Hamlin Now Available. This is part of the highly desirable Overlook at Hamlin community in Winter Garden. This home has been Well Maintained, and Tastefully Upgraded by the Original Owner. Amenities and Upgrades include: Gourmet Kitchen (with 42" Cabinetry, Gas Range, Farmer's Sink, Large Center Island), Hardwood Flooring, Plantation Shutters throughout, Shiplap Accent Walls, Custom Wine Room, and more. Improvements continued to the Outdoors as well with a Large Screened Paver Patio Outdoor Living Area, Summer Kitchen complete with TV mount, and Fenced Yard (wrought iron). Relax on the front porch overlooking the community park, or take advantage of the resort-style amenities including a clubhouse, fitness center, pool, splash pad, pavilion, event space, sports lawn, amphitheater, fire pit, canoes, private boat ramp and playground. Landscaping is maintained by the community. Located just minutes from SR 429, Florida’s Turnpike, shopping, dining, medical facilities, and the major theme parks, this home combines modern comfort with unbeatable convenience in one of Winter Garden’s most sought-after neighborhoods. Don't miss your opportunity to own this amazing home. Schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Mike Long (407-325-4104)
913 BENDING OAK TRL, WINTER GARDEN, FL 34787
$530,00013 Days on yellowkey MLS ID: O6409986
1 Days Off yellowkey (back on 6/14/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2212 Built: 2012Monthly Fee: $125 Tax: $3,860 (2025)Community: Oaks/Brandy Lake 01 Rep A & BSingle Family
Taxes:$3,860
Remarks: Under contract-accepting backup offers. Located in Winter Garden’s sought after Golf Cart District, this spacious two story home offers a flexible floor plan and a convenient location close to downtown shopping, dining, entertainment, parks, and local events. A welcoming front elevation and beautifully maintained landscaping create great curb appeal, while the oversized homesite provides added outdoor space and privacy. Inside, the open concept layout is designed for both everyday living and entertaining. The kitchen features abundant cabinetry, generous counter space, and a large breakfast bar overlooking the living and dining areas. Sliding glass doors lead to a screened lanai and fully fenced backyard, creating an ideal space to enjoy Florida’s outdoor lifestyle. A first floor bedroom with an adjacent full bath offers flexibility for guests, a home office, or multi purpose use. Upstairs, the remaining bedrooms are thoughtfully arranged to provide comfortable separation of space. Recent updates include a newer AC system and a roof that is approximately one year old, offering added peace of mind. Conveniently located with easy access to major roadways, shopping, dining, recreation, and everything that makes Winter Garden one of Central Florida’s most desirable destinations, this home combines space, functionality, and location in one exceptional opportunity.
Listing Agent: Jonathan Fadoul (347-366-7105)
7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787
$545,00048 Days on yellowkey MLS ID: O6402423
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2113 Built: 2016Monthly Fee: $253 Tax: $5,148 (2025)Community: Lakeview Pointe/Horizon West PSingle Family
Taxes:$5,148
Elementary School: Summerlake Elementary
Remarks: Welcome to 7190 Enchanted Lake Drive—your exclusive gateway to the vibrant Horizon West lifestyle. Seize the rare opportunity to own a highly sought-after 4-bedroom, 3-bathroom residence in the coveted Lakeview Pointe community, where modern luxury meets unmatched convenience. This beautifully maintained 2,294 sq. ft. home is designed for effortless entertaining, featuring an expansive open-concept first floor where abundant natural light creates a warm and inviting atmosphere. The upgraded chef's kitchen is an absolute showstopper, boasting 42-inch white cabinets, a new KitchenAid dishwasher, and a convection range. It flows seamlessly into the main living spaces, making it the perfect centerpiece for both intimate family meals and lively gatherings. Step outside to your private screened patio—an idyllic outdoor oasis designed for relaxing in the Florida breeze year-round. Everyday practicality is beautifully elevated by a charming covered walkway leading to the detached 2-car garage, while the freshly painted exterior ensures striking curb appeal and long-term durability. Inside, experience a higher standard of living with custom built-in closets throughout, offering premium storage solutions rarely found at this price point. Best of all, you can end your evenings on the cozy front porch, the ultimate spot to unwind and take in the spectacular nightly Disney fireworks—a truly magical and unique feature that makes this house feel like home.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Mark Gardner (689-248-8585)
8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787
$555,00075 Days on yellowkey MLS ID: TB8496196
REDUCED by $10,000 (1.8%) on 06/09/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2019 Built: 2017Monthly Fee: $312 Tax: $5,109 (2025)Community: Waterleigh Ph 1BSpa: YesSingle Family
Taxes:$5,109
Elementary School: Panther Lake Elementary
Remarks: Welcome to Waterleigh Phase 1 in Horizon West, Winter Garden, one of the most desirable communities in the area, known for resort-style amenities, scenic lakes, and top-rated schools. This rare one-story Arbor floor plan offers an open-concept layout with a highly sought after private fenced backyard with new landscape - perfect for relaxing, entertaining, and enjoying Florida living at its best. This home features an extended screened-in lanai & patio upgrade with a hot tub, cozy electric fireplace, dedicated home gym space, tandem 3-car garage, fresh exterior and interior paint. The home gym can be easily converted into a fourth bedroom, with drawings/plans available. This home is move-in ready with thoughtful upgrades. Minutes from Hamlin Town Center, shopping, dining, and entertainment, plus quick access to Disney and major highways. Top rated schools: Panther Lake Elementary, Water Springs Middle School, Horizon High School. Please schedule a showing to come view this rare opportunity to own a single-story home in Waterleigh Phase 1.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Timothy Shepard (727-204-9618)
279 DOE RUN DR, WINTER GARDEN, FL 34787
$599,00026 Days on yellowkey MLS ID: TB8513595
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2435 Built: 2005Monthly Fee: $57 Tax: $2,489 (2025)Community: Deerfield Place 57/1Single Family
Taxes:$2,489
Remarks: Virtually Staged. Discover your dream home in the heart of vibrant Winter Garden! This charming 3/2.5 with spacious loft offers modern upgrades galore—brand-new roof & carpet (2026), stunning 2025 kitchen remodel, fresh downstairs flooring, new water heater, epoxy garage with ceiling-mounted storage rack, elegant crown molding, 6” baseboards, wooden trim/chairail moldings, wainscoting picture frames, widened driveway, new exterior paint, and huge walk-in master closet. Enjoy a fully fenced backyard oasis with expansive 24x24 pavers on a generous 6,048 sq ft lot (Flood Zone X). Low HOA in this neighborhood. Minutes to downtown, shops, dining & highways—your perfect Central Florida lifestyle awaits! Some photos are virtually staged.
Listing is courtesy of: FLORIDA EXECUTIVE REALTY 2 (813-832-5400)
Listing Agent: Jerry Cionci (941-779-4717)
1061 PORTMOOR WAY, WINTER GARDEN, FL 34787
$535,00020 Days on yellowkey MLS ID: G5113349
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1804 Built: 2001Monthly Fee: $243 Tax: $6,801 (2025)Community: Stoneybrook West 44/134Single Family
Taxes:$6,801
Remarks: Welcome to 1061 Portmoor Way, a single-story 4-bedroom, 2-bathroom home located in the highly desirable Stoneybrook West community—a 24-hour manned, guard-gated golf community known for its resort-style living. This home features inviting modern living spaces that flow seamlessly to a fully fenced backyard with a patio, creating the perfect setting for outdoor relaxation and entertaining. New Roof installed in 2020, water heater installed in 2022, stainless steel appliances, modernized kitchen, tiled floor in kitchen, bathrooms and laundry room. Residents of Stoneybrook West benefit from an outstanding amenity lifestyle, including 24-hour security, a clubhouse, fitness center, resort-style pool, tennis, basketball and volleyball courts, playground, fishing dock, and a boat ramp with access to Black Lake. The community is also home to Stoneybrook West Golf Club and SB Prime restaurant and bar. HOA dues include internet and Spectrum TV, offering added convenience and value. Ideally located minutes from Winter Garden Village, downtown Winter Garden, and SR-429, this home provides easy access to shopping, dining, entertainment, and everyday essentials while still offering a peaceful, gated community setting.
Listing is courtesy of: ENGEL & VOLKERS CLERMONT (407-905-6700)
Listing Agent: Lisa Reed (407-509-7995)
5460 BOWMAN DR, WINTER GARDEN, FL 34787
$585,00047 Days on yellowkey MLS ID: O6402308
REDUCED by $30,000 (4.9%) on 06/10/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2474 Built: 2016Monthly Fee: $328 Tax: $8,917 (2025)Community: Overlook At HamlinSpa: NoSingle Family
Taxes:$8,917
Remarks: **Video Tour Available** Welcome to Overlook at Hamlin, where an active, vibrant lifestyle is built right into your everyday routine. Just minutes from restaurants and entertainment including PopStroke, Ford’s Garage, Agave Bandido, Cinepolis and world-famous theme parks, this home places you at the center of it all while offering peaceful views of Lake Hancock from its inviting front porch—perfect for morning coffee or winding down after a full day. Inside, the layout is designed to keep up with your pace. A bright, private office with French doors makes working from home or managing your schedule effortless. The open-concept family room flows seamlessly into the eat-in kitchen, creating a natural hub for gathering and staying connected. With granite countertops, stainless steel appliances, a gas range, a walk-in pantry and a spacious island, this kitchen is ready for everything from quick breakfasts to hosting friends. Outside you’ll find a generous screened patio—ideal for relaxing, stretching, or enjoying Florida’s year-round sunshine. There’s even a removable fence to create a separate play space! The detached garage has a covered walkway to the main house, so there are no worries about carrying groceries in during one of our famous Florida rain showers. The garage apartment adds incredible flexibility, featuring a kitchenette, full bath, and large closet—perfect for guests, a home studio, or a private fitness or wellness space. In the main house, you’ll find a versatile loft that can easily transform into a home gym, yoga studio, or creative retreat. The primary suite offers a calming escape with a tray ceiling, spa-like bathroom with a frameless tiled shower, and a walk-in closet. A 2nd upstairs bedroom and full bath provide comfortable accommodations for family or guests. Thoughtful upgrades like plantation shutters, ceiling fans, fire sprinklers in the home to help keep insurance rates low and durable large plank tile flooring enhance both style and functionality, while the upstairs laundry room and downstairs half bath add everyday convenience. Best of all, the HOA takes care of lawn maintenance—freeing up your time to enjoy the community’s exceptional amenities, including a beautiful pool, fitness center, and fishing pier. Cap off your evenings with breathtaking rocket launches and nightly theme park fireworks lighting up the sky. This is more than a home—it’s a lifestyle designed to keep you moving, connected, and inspired.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Tennille Biggers (850-628-4455)
12554 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787
$599,000273 Days on yellowkey MLS ID: O6346537
1 Days Off yellowkey (back on 6/13/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2743 Built: 2025Monthly Fee: $96 Tax: $1,862 (2024)Community: Osprey Ranch-Ph 1Single Family
Taxes:$1,862
Remarks: This tenant-occupied home, rented for $3,400/month until June 30, 2026, presents an excellent investment opportunity with immediate income. Located in the desirable Osprey Ranch community of Winter Garden, the property features 4 bedrooms, 3.5 bathrooms, and 2,743 heated square feet of living space. The functional floor plan includes a modern kitchen with all appliances and a laundry room with washer and dryer. Osprey Ranch, in the highly sought-after Horizon West area, offers a lifestyle of comfort and recreation. Community amenities include a resort-inspired pool and cabana currently under construction, plus a splash pad, playground, and dog park. Showings must be scheduled in advance with the listing agent.
Listing Agent: Adriana Pl Franzoi (407-924-0872)
2202 ROMANUM DR, WINTER GARDEN, FL 34787
$565,00069 Days on yellowkey MLS ID: O6398743
REDUCED by $14,900 (2.6%) on 06/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1889 Built: 2015Monthly Fee: $211 Tax: $3,839 (2025)Community: Alexander RidgeSingle Family
Taxes:$3,839
Remarks: Welcome to your next home in the heart of Winter Garden—where location, lifestyle, and upgrades come together seamlessly. This beautifully updated 3-bedroom, 2-bathroom home with an additional 135-square-foot flex space is perfectly positioned just 20 minutes from Disney, 15 minutes from Downtown Winter Garden, and only 10 minutes to Winter Garden Village, giving you easy access to everything Central Florida has to offer. Step inside to find brand-new luxury vinyl flooring, fresh exterior paint (2024), and a bright, open feel that makes the home both inviting and functional. The additional 135-square-foot living space under air conditioning, complete with elegant French doors, offers endless possibilities as a home office, playroom, fitness room, or second living area. Out back, enjoy your own private putting green—ideal for unwinding or entertaining guests. And with HOA-maintained landscaping, you can say goodbye to yard work and hello to low-maintenance living. Major updates bring peace of mind, including a new roof (2024), new AC unit (2025), and new gutters (2024). Additional features include a garage with epoxy flooring, a hybrid hot water heater, and a sleek GE Slate appliance package that adds a modern touch to the kitchen. This home checks all the boxes—location, upgrades, and lifestyle. Schedule your private showing today and experience it for yourself.
Listing Agent: Trevor Zwick (863-303-6114)
5754 SURPRISE LILY DR, WINTER GARDEN, FL 34787
$515,00012 Days on yellowkey MLS ID: S5151845
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2128 Built: 2021Monthly Fee: $91 Tax: $8,266 (2025)Community: Hamilton Gardens Ph 2A 2BSingle Family
Taxes:$8,266
Remarks: Location, Location, Location! Welcome to this beautiful 4-bedroom home located in the highly desirable Hamilton Gardens community in Winter Garden. Just minutes from Hamlin Town Center, you’ll enjoy convenient access to shopping, restaurants, coffee shops, movie theaters, fitness centers, Publix, and everyday essentials. This spacious home features 4 bedrooms, with all bedrooms conveniently located upstairs, creating a functional layout that offers privacy and separation from the main living areas. Downstairs, you’ll find a versatile flex space that can be used as a home office, study area, playroom, or additional sitting room. The open-concept kitchen features a gas stove, perfect for those who enjoy cooking and entertaining. The kitchen flows seamlessly into the living and dining areas, creating an inviting space for family gatherings and everyday living. Residents of Hamilton Gardens enjoy access to the community swimming pool and beautifully maintained neighborhood amenities. The home is also conveniently located near SR-429, providing quick access to Disney, Downtown Winter Garden, Downtown Orlando, and other major destinations throughout Central Florida. Families will appreciate the excellent school district, including highly rated elementary and middle schools, making this one of the most desirable areas in Winter Garden.
Listing is courtesy of: NUMBER 1 BROKER, LLC (407-566-3400)
Listing Agent: Eric Jia (407-401-1431)
6475 BREEZE FILLED LN, WINTER GARDEN, FL 34787
$585,00012 Days on yellowkey MLS ID: O6416512
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2231 Built: 2025Monthly Fee: $147 Tax: $2,107 (2025)Community: Silverleaf Oaks At Hamlin Phase 3ASingle Family
Taxes:$2,107
Remarks: Exceptional Deal Priced Below Builder’s Current Offerings! Like-New & Move-In Ready! Seller is Motivated! This stunning 5-bedroom, 3-bath Caden model by Pulte Homes has been lightly lived in and shows like new! Occupied for only a few months by its original owners, the home offers a bright, open layout with a spacious gathering room and a modern kitchen featuring quartz countertops and premium finishes. Upstairs, you’ll find the primary suite with a walk-in closet, along with three additional bedrooms and a versatile loft, perfect for a home office or entertainment space. Additional upgrades include: luxury vinyl flooring throughout, epoxy-coated garage floor, quartz countertops in the kitchen and all bathrooms. Located in the sought-after Silverleaf Reserve community, residents enjoy resort-style amenities such as a pool, pickleball court, and playground, plus easy access to A+ rated schools, shopping, dining, and major highways. Energy-efficient, fully furnished, and ready to move in, this home truly has it all!
Listing is courtesy of: ONLI REALTY GROUP LLC (352-278-8544)
Listing Agent: Vinny Machado Da Silva (352-278-8544)
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