Location: Winter Garden
Do Not Show Listings
14411 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787
$885,00054 Days on yellowkey MLS ID: O6413972
REDUCED by $10,000 (1.1%) on 07/24/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4010 Built: 2005Monthly Fee: $182 Tax: $11,924 (2025)Community: Bay Isle 48 17Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,924
Elementary School: SunRidge Elementary
High School: West Orange High
Tax Year: 2025
Middle School: SunRidge Middle
Remarks: Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
6131 ELFIN HERB WAY, WINTER GARDEN, FL 34787
$435,00054 Days on yellowkey MLS ID: O6414015
REDUCED by $15,000 (3.3%) on 07/24/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1714 Built: 2020Monthly Fee: $289 Tax: $5,990 (2025)Community: Hamilton GardensTownhouse
Taxes:$5,990
Elementary School: None
High School: Horizon High School
Middle School: None
Remarks: Welcome to 6131 Elfin Herb Way, a beautifully maintained home offering comfort, functionality, and a desirable location. Situated on a prime corner lot, this inviting residence features a spacious and thoughtfully designed floor plan with abundant natural light throughout. At the heart of the home, you will find a cute, private courtyard tucked between the main house and the garage, the perfect unique spot for relaxing or enjoying your morning coffee. The well-appointed kitchen flows seamlessly into the living and dining areas, creating an ideal space for everyday living and entertaining. The primary suite provides a private retreat, while the additional bedrooms offer flexibility for family, guests, or a home office. Its amenities include a beach-style pool, cabana, dog park, playground, and nature gardens. Hamilton Gardens is conveniently located near Hamlin Town Center, restaurants, and shopping. Conveniently located in the heart of Hamlin, the most desirable area of Horizon West, you are just minutes away from shopping, dining, top-rated schools, major roadways, and local attractions. Don't miss this opportunity to own a wonderful home in a sought-after community. Schedule your private showing today!
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Rosana Almeida (407-468-5600)
14501 GROVE RESORT AVE #3523, WINTER GARDEN, FL 34787
$200,00062 Days on yellowkey MLS ID: O6411650
0 Days Off yellowkey (back on 7/24/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1265 Built: 2018 Tax: $6,847 (2025)Community: Grove Resort & SpaSpa: YesCondo
Taxes:$6,847
High School: None
Remarks: BACK ON THE MARKET! Previous Buyer's Home Sale Fell Through – Here's Your Second Chance! DIRECT, UNOBSTRUCTED SURFARI WATER PARK VIEWS! Perched on a high floor in **Building #3—the resort's most sought-after building—**this exceptional condo enjoys one of the best locations in all of The Grove Resort. Just steps from Surfari Water Park, the Springs pools, Flip-Flops Family Fun Center & Arcade, restaurants, bars, and private Lake Austin, you'll be in the center of all the resort's world-class amenities while enjoying breathtaking, unobstructed water park views from your private balcony. This is the Disney-area vacation condo you've been waiting for! Back on the market through no fault of the property, this highly desirable residence offers one of the best locations in the entire resort. This beautifully furnished Palm model features 2 bedrooms, 2 bathrooms, 1,265 square feet, and comfortably accommodates up to 8 guests. The open-concept floor plan includes a modern kitchen with granite countertops, stainless steel appliances, and an in-unit laundry room. The split-bedroom design offers privacy, while the spacious primary suite features a king bed, walk-in closet, dual vanities, soaking tub, and separate shower. The guest suite offers two queen beds with direct access to the guest bath. Added Value: The Palm model offers the lowest HOA fee of any 2-bedroom floor plan in the resort, making it one of the best ownership values at The Grove. Located at the award-winning 4-Star Grove Resort & Spa Orlando, a Disney Good Neighbor® Hotel less than 5 miles from Walt Disney World® Resort, owners and guests enjoy complimentary Disney shuttle service and an unmatched collection of resort amenities, including: • Surfari Water Park with lazy river, water slides, and FlowRider® Double Surf Simulator • Multiple resort-style pools • Two on-site restaurants and bars • Full-service spa and fitness center • Lake Austin with fishing and watersports • Flip-Flops Family Fun Center & Arcade Whether you're searching for the perfect family vacation home, a high-demand short-term rental investment, or both, this fully furnished, turn-key condo-hotel is ready to enjoy immediately. The on-site rental management program allows the property to generate rental income while you're away—helping offset ownership costs while you create magical Disney memories for years to come. Back on the market only because the previous buyer's home sale fell through—not because of the property. Opportunities to own a direct, unobstructed water park view in Building #3 rarely become available. Schedule your showing today before it's gone again!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Joseph Mooradian (954-466-5669)
7840 WINTER WREN ST, WINTER GARDEN, FL 34787
$519,90029 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
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
$440,00033 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)
14501 GROVE RESORT AVE #3205, WINTER GARDEN, FL 34787
$325,000986 Days on yellowkey MLS ID: O6157343
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1265 Built: 2018 Tax: $4,196 (2023)Community: Grove Resort And Spa HotelCondo
Taxes:$4,196
Tax Year: 2023
Remarks: Luxury vacation rental within The Grove Resort and Spa. Beautifully furnished with modern furniture and fixtures that make for a one-of-a-kind vacation property, this fully furnished 2-bedroom, 2-bath unit can sleep up to 8 people (room with1 king bed, room with 2 full beds and queen sleeper sofa) and has a gourmet kitchen with stainless steel appliances and quartz counters. The Grove Resort and Spa offers concierge service and has several bars, restaurants, multiple pools and spas, a lazy river, water park, surfing simulator with an instructor, day spa, fishing dock, and paddle boats on Lake Austin. The resort is within several minutes of Disney World with shuttle services to the parks. This is one of Orlando's most luxurious vacation rental resorts.
Listing is courtesy of: ALL SELLERS & BUYERS REALTY INC (407-766-9940)
Listing Agent: Jamie Ampel (407-766-9940)
15665 CITRUS HARVEST RD, WINTER GARDEN, FL 34787
$699,90088 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
$869,990306 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
Tax Year: 2024
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)
14099 LOCHEND WAY, WINTER GARDEN, FL 34787
$468,00089 Days on yellowkey MLS ID: O6404015
REDUCED by $11,900 (2.5%) on 07/24/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1720 Built: 2024Monthly Fee: $150 Tax: $6,752 (2025)Community: Westhaven/OvationTownhouse
Taxes:$6,752
Remarks: Welcome to luxury living at its finest! Nestled in the prestigious West Haven at Ovation community in Winter Garden, this almost brand new 3-bedroom, 2.5-bathroom townhome is the epitome of modern elegance. As you step inside, you're greeted by an inviting open floor plan boasting an abundance of natural light and high-end finishes throughout. The spacious living area is perfect for entertaining guests or simply relaxing with your loved ones. Prepare to be dazzled by the gourmet kitchen, complete with sleek stainless steel appliances, granite countertops, stylish cabinetry, a convenient center island, refrigerator, washer and dryer. Upstairs, you'll find three generously sized bedrooms, including a luxurious master suite with a walk-in closet and a spa-like ensuite bathroom featuring dual vanities, a soaking tub, and a separate shower. Additional highlights of this stunning townhome include a private outdoor patio, perfect for enjoying your morning coffee or hosting al fresco dinners, as well as a two-car garage for your convenience. Conveniently located near top-rated schools, shopping, dining, and entertainment options, this is truly an opportunity not to be missed. Schedule your showing today and experience the pinnacle of luxury living in Winter Garden!
Listing is courtesy of: INTERNATIONAL REAL ESTATE LLC (407-760-5150)
Listing Agent: Anahi Rosario (407-721-9777)
7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787
$535,00083 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 Agent: Mark Gardner (689-248-8585)
15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787
$765,000125 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)
10294 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787
$449,90076 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
$515,00041 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)
455 WESTPOINT GARDEN CIR, WINTER GARDEN, FL 34787
$330,00019 Days on yellowkey MLS ID: O6423147
2 Days Off yellowkey (back on 7/24/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1588 Built: 2006Monthly Fee: $123 Tax: $4,229 (2025)Community: Westpoint TownhomesTownhouse
Taxes:$4,229
Remarks: Beautiful End-Unit Townhome in the Heart of Winter Garden! Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom end-unit townhome, offering the perfect combination of comfort, functionality, and location. The open-concept layout creates a bright and inviting living space, while the kitchen features solid wood cabinetry, a spacious countertop, and a full appliance package, making meal preparation and entertaining effortless. Upstairs, you'll find three generously sized bedrooms, including a comfortable primary suite with a private full bathroom, plus an additional full bath to serve the remaining bedrooms. A convenient half bath is located on the first floor for guests. This home also includes an attached one-car garage and a large screened-in rear lanai, perfect for enjoying Florida's outdoor lifestyle year-round. As shown in the photo, the covered and screened patio provides an ideal space for relaxing, dining outdoors, or entertaining while overlooking the backyard. Located in the Westpoint Townhomes community, the HOA helps maintain the neighborhood and offers a low-maintenance lifestyle. The property is just minutes from Historic Downtown Winter Garden, the West Orange Trail, Winter Garden Village at Fowler Groves, Publix, ALDI, restaurants, shopping, medical facilities, and provides easy access to SR-429, Florida's Turnpike, and Highway 50, making commuting throughout Central Florida convenient. The home is also zoned for Tildenville Elementary, Lakeview Middle, and West Orange High Schoo
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Elisa Seixas, Pa (321-663-0519)
3399 BUOY CIR, WINTER GARDEN, FL 34787
$1,204,90035 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
$475,000102 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!
434 VALLEY VIEW DR, WINTER GARDEN, FL 34787
$950,00013 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
$647,00056 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 is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Val Restrepo (321-332-8092)
9225 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787
$1,150,0006 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
$1,350,00027 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)
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