Location: Winter Garden
Do Not Show Listings
2025 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787
$715,00020 Days on yellowkey MLS ID: O6422627
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2655 Built: 1999Monthly Fee: $92 Tax: $2,506 (2025)Community: Wintermere PointeSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,506
Elementary School: Lake Whitney Elem
High School: West Orange High
Tax Year: 2025
Middle School: SunRidge Middle
Remarks: Virtually Staged. Fabulous 5 bedroom, 4 bath pool home lovingly cared for by the original owners. Situated near the end of a cul-de-sac on an almost ½-acre lot with a fully fenced backyard in the gated community of Wintermere Pointe! A long driveway provides ample parking and leads to the OVERSIZED 3-CAR GARAGE, which was extended an additional 4 feet during construction to provide exceptional storage space. Inside, this spacious and thoughtfully designed home features tile flooring throughout the main living areas downstairs, wood laminate flooring in the family room, and brand new carpet on the staircase and in the upstairs 5th bedroom. The desirable 3-way split bedroom floor plan provides wonderful privacy for family and guests. Featuring loads of storage throughout, including an oversized under-stair storage closet in the back hall, a generously sized linen closet in the alcove between Bedrooms 2 and 3, and an additional storage closet in the laundry room. The primary suite is privately located on one side of the home and features French doors opening to the lanai and pool, two walk in closets and a beautifully UPDATED primary bath with new flooring, separate vanities that offer plenty of storage, quartz countertops, a renovated shower with glass surround and updated showerhead plus a private water closet with a new commode. All commodes throughout home have been replaced with "comfort height" commodes. At the heart of the home is the spacious kitchen offering abundant cabinetry, granite countertops and LG stainless appliances (Bosch dishwasher) replaced in 2022. The kitchen opens to the family room w/surround sound, creating a comfortable and inviting space for everyday living and entertaining. Upstairs, the huge 5th bedroom offers incredible flexibility with two walk in closets and a private bathroom - perfect for guests, multigenerational living, a bonus room or private retreat. Outdoor living is exceptional! A huge Florida room was added across the back of the home, providing additional all-season living and entertaining space beyond the screened pool and lanai. The expansive, fully fenced backyard and almost ½-acre homesite provide plenty of room to enjoy the Florida lifestyle. MAJOR UPDATES INCLUDE: ALL NEW energy-efficient windows (June 2023) and doors (2024), Water softener (February 2024), Water heater (September 2023), garage door opener (2021), Roof (May 2017) and HVAC (September 2015) with annual maintenance service. AC ducts were inspected with boots resealed to drywall and collars in June 2019, then professionally cleaned and inspected in March 2024. Annual septic service, including draining and filter cleaning, was completed in January 2026, and the dryer vent was cleaned in April 2026. The transferable termite bond renews in November 2026. Additional improvements include replacement of the sprinkler meter including the majority of electrical sprinkler valves, gutter cleaning and sealing and installation of Gutter Guards in March 2025, along with replacement of two electrical valves at the pool pump. THE LOCATION IS FANTASTIC! Just 5 minutes to Winter Garden Village for abundant shopping and dining, including the new Seasons 52 coming soon. Approximately 10 minutes to charming Downtown Winter Garden with its popular restaurants, shops and Saturday Farmers Market and approximately 16 minutes to Disney! Zoned for highly rated Lake Whitney Elementary, SunRidge Middle, and West Orange High School. This home is truly a special opportunity!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Sherri Palmer (407-718-0412)
7840 WINTER WREN ST, WINTER GARDEN, FL 34787
$519,90027 Days on yellowkey MLS ID: O6421167
REDUCED by $6,000 (1.1%) on 07/24/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2004 Built: 2015Monthly Fee: $251 Tax: $7,385 (2025)Community: Summerlake Pd Ph 1B RepSingle Family
Taxes:$7,385
Elementary School: Summerlake Elementary
High School: Horizon High School
Middle School: Hamlin Middle
Remarks: Come take a look at this gorgeous 3 bedrooms and 2 and half baths home located in Summerlake community! Lake (pond) view !! Professionally decorated and loaded with designer upgrades including laminate wood flooring, Master bathroom has a walk in closet along with dual sinks. Other features include a two car garage, front porch, carpet in the bedrooms. Community amenities include a resort style pool, fitness center, clubhouse, dog park, tot lot, basketball and tennis courts. Summerlake Clubhouse & Fitness Center is a social and recreational hub, and the neighborhood is close to central Florida’s renowned recreation, including the theme parks, beaches, and lakes, for waterskiing, boating, swimming, and fishing! Also , as a great addition , a gorgeous whole slab huge family table is included ( please check pictures) with this sale. Table price was 12k when purchased, very rich and nice looking . Also,as an extra - there is an additional LG french door refrigerator in the garage.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
721 S WOODLAND ST, WINTER GARDEN, FL 34787
$440,00031 Days on yellowkey MLS ID: O6419636
REDUCED by $10,000 (2.2%) on 07/23/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1034 Built: 1955 Tax: $508 (2025)Community: Borders & Woosley SubSingle Family
Taxes:$508
Elementary School: Dillard Street Elem
Middle School: Lakeview Middle
Remarks: Located within Winter Garden’s golf cart district and just minutes from Plant Street, this property offers a distinctive combination of current residential use, C-2 General Commercial zoning, and no HOA. The single-story, concrete-block home includes 2 bedrooms, 1 bathroom, 1,034 square feet of heated living space, an enclosed porch that provides additional flexible space, and a roof replaced in 2023. The interior is ready for renovation, allowing the next owner to update the property according to their intended use and vision. Situated on an approximately 0.19-acre homesite, the property also features mature shade trees, a concrete driveway, and fenced sections of the yard. Its central Winter Garden location provides convenient access to the restaurants, shops, farmers market, community events, and West Orange Trail surrounding downtown and Plant Street, while nearby golf-cart-friendly roadways offer another way to explore the area. Whether considered for continued residential use, a renovation project, or a future business opportunity, this property presents a range of possibilities in a well-connected location. Buyers should independently verify all intended uses, permitting requirements, and zoning regulations with the City of Winter Garden.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Christopher Bessette (407-292-5400)
15665 CITRUS HARVEST RD, WINTER GARDEN, FL 34787
$699,90086 Days on yellowkey MLS ID: O6400896
REDUCED by $20,000 (2.8%) on 07/11/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2931 Built: 2016Monthly Fee: $235 Tax: $5,441 (2025)Community: Hickory Hammock Ph 2ASingle Family
Taxes:$5,441
Elementary School: Whispering Oak Elem
Remarks: PREMIUM CONSERVATION LOT offering privacy and natural beauty, with a GREEN SPACE on the right side of the home and a park with sitting benches and sidewalks located across the street. Discover exceptional value and picturesque Florida living in this beautifully appointed 4-bedroom, 2.5-bath home offering 2931 square feet of thoughtfully designed living space. Enjoy tranquil views of the Lake Burnett inlet from the screened lanai. Inside, a bright open-concept floor plan showcases tile flooring throughout the first floor, luxury vinyl plank flooring upstairs, crown molding, custom window casings, a designer feature wall in the dining room, and elegant finishes throughout. The spacious kitchen is the heart of the home, featuring 42-inch cabinetry, stainless steel appliances, a walk-in pantry, a kitchen island, and seamless flow into the great room and dining areas—perfect for entertaining and everyday living. A flex room / office on the first floor, provides ideal additional living area or work-from-home space. Upstairs, the game room offers even more flexibility. Double doors lead to the spacious primary suite, featuring a charming window bench seat, large walk-in closet, dual vanities, soaking tub, walk-in shower, and private water closet. Generously sized secondary bedrooms provide ample space, with two bedrooms featuring walk-in closets. Step outside to the fully fenced backyard with aluminum fencing and dual side gates, where peaceful conservation views create the perfect backdrop for relaxing or entertaining. Additional upgrades include fresh exterior paint, a new water heater, new dishwasher, newer washer and dryer, gutters with premium leaf protection, and pre-wiring for a security system. Residents of Hickory Hammock enjoy resort-style amenities including a clubhouse, pool, fitness center, tennis courts, sand volleyball courts, fishing pier, playground, walking trails, community parks, and golf cart-friendly streets. Conveniently located just 10 minutes from the 429, connecting you to the Turnpike and I-4. A quick 10 minutes to the Winter Garden Village and Downtown Winter Garden, you'll enjoy easy access to boutique shopping, restaurants, coffee shops, Plant Street Market, and the popular Saturday Farmers Market. Now offered at an exceptional value, this home presents an outstanding opportunity to enjoy the Florida lifestyle you've been dreaming of. Schedule your private showing today. WELCOME HOME!
Listing is courtesy of: CARIS REALTY AND INVESTMENTS INC (407-595-0009)
Listing Agent: Janelle Conway (407-595-0009)
14327 WABASSO LOOP, WINTER GARDEN, FL 34787
$869,990304 Days on yellowkey MLS ID: O6347454
REDUCED by $30,000 (3.3%) on 07/24/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3710 Built: 2022Monthly Fee: $200 Tax: $12,141 (2024)Community: Tilden Place/Winter GardenSingle Family
Taxes:$12,141
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Beautifully upgraded home located in the desirable gated community of Tilden Place in the heart of Horizon West. This home showcases one of the builder’s highest-level design upgrade packages, featuring premium cabinetry, upgraded flooring, elegant finishes, crown molding, designer lighting, and a gourmet kitchen with luxury selections throughout. The fully fenced backyard provides privacy and is perfect for entertaining, pets, or outdoor living. Outstanding location just minutes from Hamlin Town Center, offering convenient access to shopping, dining, entertainment, Cinepolis Luxury Cinemas, Publix, Walgreens, and major roadways including SR-429. Nearby restaurants include The French Cafe, Bosphorous Turkish Cuisine, Agave Azul Cocina Mexicana, Ford’s Garage, Gochujang Korean BBQ, Capone’s Coal Fired Pizza, Teak Neighborhood Grill, Jeremiah’s Italian Ice, Kelly’s Homemade Ice Cream, Starbucks, and Home State Brewing Co. Zoned for highly sought-after schools:Keenes Crossing Elementary School, Bridgewater Middle School, Windermere High School, Foundation Academy – Tilden Campus; The Goddard School of Winter Garden, Cranium Academy, StarChild Academy of Winter Garden. Easy access to Walt Disney World, Flamingo Crossings, Winter Garden Village, Orlando Health Horizon West Hospital, and the future Horizon West growth corridor. Don’t miss this exceptional opportunity to own one of Horizon West’s finest homes in a gated community with premium builder upgrades. Schedule your private tour today and experience everything this beautiful home.
Listing is courtesy of: KARDOSH REALTY (407-499-4466)
Listing Agent: Stephanie Li (407-538-7599)
2200 ROMANUM DR, WINTER GARDEN, FL 34787
$550,00073 Days on yellowkey MLS ID: O6408190
0 Days Off yellowkey (back on 6/29/2026)
REDUCED by $10,000 (1.8%) on 06/24/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2561 Built: 2015Monthly Fee: $211 Tax: $8,843 (2025)Community: Alexander RdgSpa: NoSingle Family
Taxes:$8,843
Remarks: Come see 2200 Romanum Dr, recently updated with fresh interior paint and partial flooring replacement throughout. The kitchen features a functional island, all stainless steel appliances, and an accent backsplash. The primary bedroom includes a walk in closet, while its bathroom provides double sinks and a separate tub and shower. An exterior covered patio extends to a fenced in backyard. This updated property combines modern comfort and outdoor enjoyment. 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)
7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787
$535,00081 Days on yellowkey MLS ID: O6402423
REDUCED by $10,000 (1.8%) on 06/25/2026
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
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 on a premium corner lot in the coveted Lakeview Pointe community. Perfectly positioned just moments from the premier dining, shopping, and entertainment at Hamlin Town Center, this property offers the ultimate Central Florida lifestyle with seamless access to the FL-429 and the magic of Disney World. Step inside to experience an expansive 2,113 square foot layout designed for effortless entertaining and modern flexibility. The open-concept first floor boasts an upgraded chef's kitchen featuring 42-inch white cabinets, a new KitchenAid dishwasher, a convection range, and beautiful stone counters. The kitchen flows seamlessly into the light-filled main living space, which opens directly to a private, screened-in patio and fully fenced yard. Uniquely advantageous, the first floor includes a convenient 4th bedroom and full bathroom, ideal for an elegant home office or guest suite . Upstairs, discover a spacious bonus Loft alongside three additional bedrooms, including a luxurious primary retreat featuring premium custom built-in closets . A covered walkway leads out to your detached 2-car garage, while the freshly painted exterior delivers stunning curb appeal. Best of all, you can end your evenings on your cozy front porch enjoying spectacular views of the nightly Disney fireworks. Boasting a low monthly HOA of $253 and absolutely no CDD fees, this immaculate home represents an incredible, newly adjusted value in Winter Garden. Schedule your private tour today!
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Mark Gardner (689-248-8585)
15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787
$765,000123 Days on yellowkey MLS ID: O6393987
1 Days Off yellowkey (back on 7/24/2026)
REDUCED by $30,000 (3.8%) on 05/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4307 Built: 2014Monthly Fee: $114 Tax: $5,670 (2025)Community: Reserve/Carriage Pointe Ph 1Single Family
Taxes:$5,670
Elementary School: Hamlin Elementary
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 15558 Sandfield Loop, a refreshed residence offering a turn-key lifestyle within one of Winter Garden’s most exclusive and hard-to-find GATED community. This house has been freshly updated from top to bottom, including new interior and exterior paint that makes the whole place feel brand new. The first thing you'll notice when you walk in is the massive, two-story high ceiling in the living area—it brings in tons of natural light and gives the home a great, airy feel. The kitchen has been fully redone with modern two-tone cabinets and beautiful quartz countertops. Throughout the home, you will find fresh paint and new flooring that perfectly complement the contemporary aesthetic. Situated within a highly-rated school zone, this MOVE IN READY property combines the security of a premier gated community with grand architectural features and stylish updates.
Listing is courtesy of: ORLANDO HIGHLAND REALTY LLC (561-385-7610)
Listing Agent: Xiaoli Lin (561-385-7610)
15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787
$669,99024 Days on yellowkey MLS ID: S5153036
INCREASED by $20,100 (3.1%) on 07/14/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2930 Built: 2024Monthly Fee: $202 Tax: $9,669 (2025)Community: Harvest/OvationSingle Family
Taxes:$9,669
Middle School: Horizon West Middle School
Remarks: Exceptional opportunity in Winter Garden. This stunning 2024 home offers 5 bedrooms, 4.5 bathrooms, and a fully independent Next Gen suite featuring its own private entrance, living room, bedroom, full bathroom, and kitchenette—perfect for multigenerational living, a private home office, or even generating additional rental income. With over $60,000 in completed upgrades, this property delivers exceptional value and a truly move-in-ready experience. Ideally located just minutes from Disney, Flamingo Crossings, Hamlin Town Center, top-rated schools, hospitals, shopping, dining, and entertainment, this home blends modern comfort with unbeatable convenience. The open-concept layout showcases high ceilings, a beautifully remodeled kitchen, porcelain tile flooring throughout the first floor, upgraded second-floor flooring, wood stairs, premium interior paint, a paver driveway and patio, epoxy-coated garage flooring, and numerous additional enhancements. A rare chance to own a nearly new, highly upgraded home in one of Winter Garden’s most desirable areas. Buyer and buyer’s agent to verify all information, including room sizes, HOA details, school zoning, rental restrictions, lease terms, and all property information.
Listing is courtesy of: MOSAIC PARTNERS GROUP (407-989-2021)
Listing Agent: Andrea Munoz (407-989-2021)
10294 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787
$449,90074 Days on yellowkey MLS ID: O6407798
REDUCED by $10,000 (2.2%) on 07/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1689 Built: 2019Monthly Fee: $245 Tax: $7,600 (2025)Community: Waterleigh Ph 2C-1Single Family
Taxes:$7,600
Middle School: Water Spring Middle
Remarks: One or more photo(s) has been virtually staged. MOVE-IN READY and the BEST-PRICED SINGLE-STORY HOME IN WATERLEIGH with the ability to close quickly! Situated on an oversized 145-foot-deep homesite, this beautifully maintained 3 Bedroom, 2 Bathroom Laurel floor plan offers an extended paver driveway, spacious backyard, and an open-concept layout perfect for everyday living. The gourmet kitchen features a large granite island, walk-in pantry, brand-new stainless steel appliances, upgraded pendant lighting, and beautiful Toscana stained glass windows. The spacious primary suite includes dual sinks, an oversized walk-in shower with bench, and a walk-in closet. A split floor plan provides added privacy, while the rear-entry garage offers built-in cabinetry, granite workspace, and extra storage. Additional upgrades include designer lighting, upgraded faucets, extensive tile flooring, wood window sills, and window blinds throughout. Enjoy Waterleigh's resort-style amenities including 4 pools, 3 clubhouses, fitness centers, tennis, pickleball, walking trails, playgrounds, and HOA lawn maintenance. Conveniently located just minutes from Disney, Hamlin Town Center, shopping, dining, SR-429, and I-4. Beautifully upgraded, competitively priced, and ready for its next owner.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Sabrina Freeman (407-446-5541)
1142 DUNBROOKE ST, WINTER GARDEN, FL 34787
$515,00039 Days on yellowkey MLS ID: O6417527
1 Days Off yellowkey (back on 6/26/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2068 Built: 2005Monthly Fee: $53 Tax: $4,251 (2025)Community: Chapin StationSingle Family
Taxes:$4,251
Elementary School: Maxey Elem
High School: Ocoee High
Remarks: Under contract-accepting backup offers. Virtually staged. Welcome to Chapin Station! On an almost quarter-acre lot, this four-bedroom, three-bath home offers a light and spacious split-bedroom open floor plan designed for comfort and functionality. Go inside to find soaring ceilings and an open layout featuring a formal dining room, a large family room and a bright breakfast nook overlooking the kitchen. Double-pane windows provide added energy efficiency throughout the home. The living areas seamlessly connect to the expansive covered rear patio and private backyard, creating the ideal setting for everyday living and entertaining. The thoughtfully designed split floor plan provides privacy for all. The primary suite features vaulted ceilings, dual walk-in closets and an en-suite bath with double vanities, a garden tub and a separate shower. On the opposite side of the home, two secondary bedrooms share a full bath, while a separate guest suite and additional bath offer ideal accommodations for visitors or multigenerational living. The oversized backyard provides ample space to create your dream outdoor oasis, whether you envision a pool, play area, garden or outdoor entertainment space. The large covered patio is ideal for grilling, relaxing, and gathering with family and friends. In the sought-after Chapin Station community, this well-maintained home offers easy access to the West Orange Trail, historic downtown Winter Garden, major highways, hospitals, shopping, dining and Central Florida's world-famous theme parks.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Naresh Mistry (321-356-7882)
3399 BUOY CIR, WINTER GARDEN, FL 34787
$1,204,90033 Days on yellowkey MLS ID: O6419829
REDUCED by $20,000 (1.6%) on 07/24/2026
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 5277 Built: 2020Monthly Fee: $128 Tax: $17,116 (2025)Community: Lakeview PreserveSingle Family
Taxes:$17,116
Remarks: Experience luxury waterfront living in one of Winter Garden's most desirable communities! This stunning home offers the perfect blend of elegant design, spacious living, and breathtaking water views. From the moment you arrive, you'll appreciate the attractive curb appeal, paver driveway, and spacious three-car garage. Inside, you'll find an expansive open floor plan designed for both everyday living and entertaining. The heart of the home is the impressive chef's kitchen featuring an oversized quartz island, built-in wall oven and microwave, stainless steel appliances, abundant cabinetry, a walk-in pantry, and plenty of prep space. The kitchen flows seamlessly into the spacious family room, highlighted by beautiful luxury flooring, tray ceilings, decorative wall accents, and oversized sliding glass doors that frame the picturesque lake views. The first-floor primary suite is a true retreat, offering private access to the screened lanai, generous proportions, and a luxurious ensuite bath complete with dual vanities, an oversized walk-in shower, private water closet, and an expansive walk-in closet. Step outside to the oversized screened lanai and enjoy your morning coffee or evening sunsets overlooking the peaceful water. The backyard offers plenty of room to relax while taking in the tranquil views. Additional features include a large laundry room, spacious secondary bedrooms, ample storage throughout, modern neutral finishes, and dual HVAC systems for added comfort and efficiency. Located in the highly sought-after Winter Garden area, you'll enjoy easy access to shopping, dining, entertainment, and major roadways including SR-429, Florida's Turnpike, and Highway 50. Historic Downtown Winter Garden, Winter Garden Village, Horizon West, and Disney are all just a short drive away. The community also offers convenient access to parks, walking trails, and everything that has made Winter Garden one of Central Florida's most desirable places to call home. If you've been searching for a spacious, move-in-ready waterfront home with upscale finishes and an exceptional location, this one deserves a spot at the top of your list.
Listing is courtesy of: ACME REAL ESTATE FLORIDA LLC (407-601-4958)
Listing Agent: Heather Unger, Pa (407-810-6304)
12050 BRACCO ST, WINTER GARDEN, FL 34787
$475,000100 Days on yellowkey MLS ID: O6398494
REDUCED by $14,900 (3.0%) on 07/16/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1770 Built: 2023Monthly Fee: $110 Tax: $7,195 (2025)Community: Highland RidgeSingle Family
Taxes:$7,195
Remarks: Modern Living Meets Prime Location in Horizon West! Welcome to this stunning 2023-built Meritage Home in the sought-after Highland Ridge community. This energy-efficient "Bungalow" style residence features 3 bedrooms, 2.5 bathrooms, and a versatile second-floor loft—perfect for a home office or media room. The open-concept main floor boasts a gourmet kitchen with a large quartz island, sleek cabinetry, and stainless steel appliances, all flowing into a bright living area bathed in natural light thanks to its desirable Southern exposure. Energy Efficiency: Built with Meritage’s signature spray-foam insulation and Energy Star appliances, ensuring year-round comfort and significantly lower utility bills. Community & Location: Enjoy resort-style amenities including a pool, cabana, pickleball courts, and playground. Ideally located just minutes from Walt Disney World via Western Way and walking distance to the vibrant Flamingo Crossings Town Center for dining, shopping, and entertainment. Quick access to SR-429 makes commuting a breeze. Don’t miss your chance to own a like-new home in Winter Garden’s fastest-growing corridor!
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Rosana Almeida (407-468-5600)
1005 CHASE DR, WINTER GARDEN, FL 34787
$599,99960 Days on yellowkey MLS ID: O6411451
REDUCED by $1 (0.0%) on 07/09/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2319 Built: 2005Monthly Fee: $68 Tax: $7,087 (2025)Community: Island Pointe SubSingle Family
Taxes:$7,087
Remarks: One or more photo(s) has been virtually staged. This is the one in Winter Garden's Golf Cart District. SELLER BONUS: from now until July 31st, the seller will credit up to $5,000 toward a privacy fence on any full-price contract. A fully renovated 4-bed, 2.5-bath home on a corner lot in the golf cart community of Island Pointe, and it is move-in ready. The 2025 updates cover everything: new roof, new AC, updated electrical, updated plumbing, new tile downstairs, LVP upstairs, and a brand new kitchen with stone countertops and modern cabinetry. Double-height ceilings and natural light greet you at the entry, and the kitchen flows right into the living space so the home feels open and connected. The kitchen has stone countertops, soft-close cabinets, a farmhouse deep sink, and real counter space that works for everyday life. The primary suite is its own retreat, with two walk-in closets, a glass walk-in shower, and a soaking tub. Three additional bedrooms give you room to grow. Outside you get a 3-car garage, a corner lot, and a quiet cul-de-sac, all inside the Island Pointe golf cart community. HOA runs $68 a month. Hop on your golf cart and you are minutes from Plant Street, the Saturday farmers market, the West Orange Trail, and some of the best restaurants and coffee in downtown Winter Garden.
Listing Agent: Elizabeth Lofholm (906-221-4905)
434 VALLEY VIEW DR, WINTER GARDEN, FL 34787
$950,00011 Days on yellowkey MLS ID: O6425087
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2765 Built: 2000Monthly Fee: $83 Tax: $4,087 (2025)Community: Courtlea Oaks Ph 01ASingle Family
Taxes:$4,087
Remarks: Under contract-accepting backup offers. Nestled in the highly coveted Courtlea Oaks community, within Winter Garden’s sought-after golf cart district, this beautifully updated home offers the perfect blend of timeless charm and modern luxury. Enjoy the lifestyle that has made historic downtown Winter Garden one of Central Florida’s most beloved destinations—just minutes away you’ll find award-winning restaurants, boutique shopping, the renowned Saturday Farmers Market, live entertainment, festivals, and miles of the West Orange Trail. Situated on an oversized .33-acre homesite, this exceptional residence offers 2,765 square feet with three bedrooms, two-and-a-half baths, and thoughtfully designed living spaces filled with architectural character. From the moment you enter, you’ll be welcomed by soaring ceilings, rich hardwood flooring, custom board-and-batten millwork, crown molding, and a stunning two-story foyer that creates an unforgettable first impression. At the heart of the home is a beautifully renovated kitchen featuring custom white cabinetry, a center island, farmhouse sink, professional-style gas range with pot filler, stainless steel appliances, and generous workspace—perfectly designed for both everyday living and effortless entertaining. The kitchen flows seamlessly into the spacious family room and sun-filled dining area overlooking the backyard oasis. Upstairs, the expansive loft provides exceptional flexibility as a media room, home office, fitness space, or could easily accommodate a fourth bedroom. The secondary bedrooms are generously sized, including one with a charming custom-built window desk. The beautifully updated bathrooms continue the home’s timeless design with quality finishes throughout. Step outside to your own private retreat featuring a sparkling pool, expansive brick paver deck, lush landscaping, and plenty of room for entertaining or simply relaxing under the Florida sun. Homes in Courtlea Oaks are rarely available. Combining an exceptional location, beautiful updates, timeless architecture, and one of Winter Garden’s most desirable lifestyles, this is a home you’ll be proud to call your own.
Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)
Listing Agent: Jennifer Coon (321-948-8056)
11165 GREEN CITRON ALY, WINTER GARDEN, FL 34787
$647,00054 Days on yellowkey MLS ID: O6413226
REDUCED by $1,000 (0.2%) on 07/24/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2043 Built: 2024Monthly Fee: $89 Tax: $8,682 (2025)Community: Northlake/Ovation Ph 1Single Family
Taxes:$8,682
Remarks: Welcome to this stunning, nearly new home, just two years old and thoughtfully designed for modern living. Perfectly positioned directly across from a beautiful conservation area and just steps from the community amenities center, this exceptional residence offers the ideal blend of comfort, convenience, and style. As you enter through the inviting front porch, you'll find a private first-floor bedroom and full bathroom—perfect for guests, in-laws, or a home office. The heart of the home features a gourmet kitchen that seamlessly flows into the spacious open-concept living and dining areas, creating the perfect space for entertaining and everyday living. Step through elegant French doors to enjoy the extended covered lanai and side yard, offering plenty of outdoor living space. The oversized driveway and two-car garage provide ample parking and storage. Upstairs, you'll discover two additional bedrooms, a full bathroom, and an expansive primary suite designed as a true retreat. The luxurious primary bathroom features dual vanities, an oversized walk-in shower, and a spacious walk-in closet. Located within a highly sought-after school district and just minutes from Orlando Health Hospital, Hamlin Town Center, and Flamingo Crossings Town Center, this home offers unparalleled convenience to shopping, dining, entertainment, and major roadways. This move-in-ready gem truly has everything you've been looking for. Schedule your private showing today and experience the lifestyle this exceptional home has to offer!
Listing Agent: Val Restrepo (321-332-8092)
9225 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787
$1,150,0004 Days on yellowkey MLS ID: O6427589
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3897 Built: 2017Monthly Fee: $158 Tax: $15,124 (2025)Community: Watermark Ph 1BSingle Family
Taxes:$15,124
Remarks: Welcome to 9225 Holliston Creek Place, an exceptional pool home nestled on a premium corner lot in one of Winter Garden's most sought-after communities. From the moment you arrive, the lush landscaping, side-entry garage, and beautifully maintained exterior set the tone for everything this home has to offer. Step inside and you are immediately greeted by soaring ceilings, an abundance of natural light, and a thoughtfully designed open floor plan that flows seamlessly from the formal living and dining areas into the heart of the home. The spacious kitchen is a true entertainer's dream, featuring generous counter space, ample cabinetry, and a layout that opens directly to the main living area — perfect for gatherings of any size. The dedicated home office is one of the standout features of this property — large, well-appointed, and completely separate from the living spaces, giving you the ideal work-from-home setup or the flexibility to use as a fifth bedroom, playroom, or media room. The primary suite is a private retreat, offering a generous layout, spa-like en suite bathroom with dual vanities, soaking tub, and walk-in shower. Secondary bedrooms are well-sized and thoughtfully positioned for privacy. Step outside and discover your own backyard oasis. The screened pool and lanai area is designed for true Florida living — whether you are taking a morning swim, hosting a weekend cookout, or simply unwinding at the end of the day. The summer kitchen is fully equipped and perfectly positioned to make outdoor entertaining effortless, with everything you need just steps from the pool deck. Being on a corner lot provides additional yard space, extra privacy, and enhanced curb appeal that interior lots simply cannot match. Located in a vibrant, well-established Winter Garden community with easy access to top-rated schools, SR-429, the 408, shopping, dining, and all of Central Florida's best attractions — this one truly checks every box.
Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)
Listing Agent: Michael Bouchard (407-443-1284)
7467 JOHN HANCOCK DR, WINTER GARDEN, FL 34787
$1,350,00025 Days on yellowkey MLS ID: O6421848
1 Days Off yellowkey (back on 7/15/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3964 Built: 2019Monthly Fee: $215 Tax: $16,560 (2025)Community: West Lake Hancock EstatesSpa: YesSingle Family
Taxes:$16,560
Elementary School: Independence Elementary
Remarks: Luxury, comfort, and an unbeatable location come together in this exceptional home in the highly sought-after Horizon West community. Perfectly positioned just minutes from Disney, shopping, dining, major highways, and top-rated schools, this move-in-ready residence offers the ideal combination of elegance, functionality, and the Florida lifestyle you’ve been looking for. Designed for both everyday living and entertaining, the home features 4 spacious bedrooms, 3 full bathrooms, a half bath, a dedicated office, a versatile bonus room, and a 3-car garage. The open-concept kitchen showcases a large center island, stainless steel appliances, and seamlessly connects to the spacious living areas. What truly sets this home apart is its stunning outdoor oasis. Since its original purchase, the owners have transformed the backyard into a private resort featuring a beautiful custom pool, an expansive covered lanai, and a fully equipped summer kitchen, creating the perfect setting for weekend barbecues, family gatherings, or simply relaxing while enjoying the peaceful pond views. Thoughtfully upgraded and impeccably maintained, this home is truly turnkey, allowing its next owners to move in and immediately enjoy one of Central Florida’s most desirable lifestyles. Whether you’re looking for your primary residence or a place where family and friends can create unforgettable memories, this property delivers the perfect blend of luxury, comfort, convenience, and quality of life.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Diogo Mac Knight (407-364-7522)
15456 GILLIGAN CT, WINTER GARDEN, FL 34787
$550,000361 Days on yellowkey MLS ID: A4660262
0 Days Off yellowkey (back on 7/2/2026)
REDUCED by $25,000 (4.3%) on 06/12/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2571 Built: 2020Monthly Fee: $102 Tax: $8,702 (2024)Community: Winding Bay Ph 1BSingle Family
Taxes:$8,702
Remarks: Disney fireworks views, single-story living, low HOA — just 3.9 miles from Disney. Welcome to Winding Bay in Winter Garden, where location, lifestyle, and long-term value come together in one beautifully maintained home. This pristine 3-bedroom, 3.5-bath residence with a flexible bonus room offers the perfect setup for everyday living, visiting guests, remote work, or a potential future sleeping space with proper modification and verification. From the moment you arrive, the home makes a statement with its brick-paved driveway, stone-accented façade, and inviting curb appeal. Inside, the bright open floor plan is designed for comfort and function, featuring a dedicated built-in desk area, an oversized mudroom, an adjacent laundry room, custom cabinetry, and generously sized guest suites. The heart of the home is the chef-inspired eat-in kitchen, complete with 42-inch soft-close cabinetry, quartz countertops, designer backsplash, vented range hood, built-in microwave, massive walk-in pantry, and an oversized island with seating for up to eight — ideal for entertaining, hosting family, or gathering after a day at the parks. The open dining and family room are filled with natural light and flow seamlessly to the custom-designed backyard, where you can relax and enjoy direct views of Disney fireworks from home — a rare and memorable feature that truly sets this property apart. Winding Bay offers a peaceful, pride-of-ownership atmosphere with no short-term rentals permitted, helping preserve the neighborhood feel while still keeping you minutes from Disney, dining, shopping, schools, and major conveniences. Residents also enjoy a community pool, dog park, and a low HOA of just $102/month. Move-in ready, meticulously maintained, and positioned in one of Winter Garden’s most desirable communities, this home is ideal for owner-occupants, Disney professionals, second-home buyers, or anyone seeking proximity to the magic without the noise, crowds, or rental turnover. Private showings available by appointment.
Listing is courtesy of: NEXTHOME CASA BELLA ELITE (813-726-5646)
Listing Agent: Loren Rosenthal (813-726-5646)
15741 SWEET LEMON WAY, WINTER GARDEN, FL 34787
$1,149,00041 Days on yellowkey MLS ID: O6417058
REDUCED by $16,000 (1.4%) on 07/24/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3624 Built: 2020Monthly Fee: $55 Tax: $12,068 (2025)Community: Highlands/SummerlakeSpa: NoSingle Family
Taxes:$12,068
Remarks: ***PRICED TO SELL!*** WELCOME to this stunning and highly desirable two-story Xavier floor plan by K. Hovnanian Homes, perfectly positioned on a premium homesite with no rear neighbors, offering exceptional privacy and a peaceful backyard retreat. Located in the heart of Horizon West, just minutes from Hamlin Town Center, this exceptional residence combines luxury, functionality, and modern Florida living. Boasting 5 bedrooms and 4.5 bathrooms, this thoughtfully designed floor plan offers plenty of space for family and guests. The first floor features beautiful luxury vinyl plank flooring throughout and includes a dedicated home office with elegant French doors, ideal for remote work or a private study. A formal dining room provides the perfect setting for hosting gatherings, while the gourmet kitchen serves as the heart of the home with stunning cabinetry, premium finishes, a large center island, and an inviting breakfast area that seamlessly opens to the spacious great room. A generously sized guest suite is conveniently located on the first floor, featuring tranquil views of the pool and backyard. Its private bath also provides direct access to the outdoor living area, making it ideal for guests and poolside entertaining. Step outside to your own private backyard oasis. Designed for relaxation and entertainment, the heated saltwater pool features a beautiful waterfall fountain, an oversized sun shelf, and expansive deck space for lounging and enjoying Florida's year-round sunshine. The covered lanai is already equipped with water, sewer, and gas connections, providing the perfect foundation to create your dream outdoor summer kitchen. Upstairs, the luxurious primary suite offers a peaceful retreat with dual walk-in closets and a spacious en-suite bath. Additional bedrooms and living space provide flexibility for growing families, guests, or hobbies. Additional upgrades include a two-car garage with high-quality epoxy flooring, full gutters for added protection and functionality, and serene views beyond the preserve area. With no direct rear neighbors, this home offers a rare combination of privacy, natural beauty, and convenience. Don't miss this incredible opportunity to own a piece of paradise in one of Horizon West's most sought-after locations. Schedule your private showing today!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Cristiane Carneiro Spindola Rocha Lima (407-766-9333)
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