Location: Winter Garden
Do Not Show Listings
13856 GLYNSHEL DR, WINTER GARDEN, FL 34787
$850,00044 Days on yellowkey MLS ID: O6416757
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3538 Built: 2003Monthly Fee: $167 Tax: $11,261 (2025)Community: GlynwoodSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,261
Elementary School: SunRidge Elementary
High School: West Orange High
Tax Year: 2025
Middle School: SunRidge Middle
Remarks: Located in the highly desirable gated community of Glynwood in Winter Garden, this spacious 5-bedroom, 4-bath pool home offers over 3,500 square feet of living space on a private cul-de-sac lot. The versatile floor plan features a first-floor owner's suite, dedicated office/den, formal and casual living areas, and an upstairs bonus/media room with an additional bedroom and bath—ideal for guests, multi-generational living, or a home theater. The screened pool and spa create a private backyard retreat, while the 3-car garage (AC by Modern Wall Unit and Upgraded Garage Floor Coating) provides ample storage and parking. Residents enjoy access to community amenities including a pool, tennis courts, playground, and gated entry. Conveniently located near Winter Garden Village, historic downtown Winter Garden, major highways, shopping, dining, and area attractions.
Listing is courtesy of: CHOICEPOINTE REALTY, INC. (888-246-5758)
Listing Agent: Mary Dees (407-468-8285)
16802 OAKBORO ST, WINTER GARDEN, FL 34787
$500,0008 Days on yellowkey MLS ID: O6425489
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1705 Built: 2020Monthly Fee: $257 Tax: $7,269 (2025)Community: Waterleigh Ph 3B 3C & 3DSpa: NoSingle Family
Taxes:$7,269
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: Welcome to this beautifully maintained Laurel floor plan, featuring fresh professional exterior paint (2026), 3 bedrooms, 2 bathrooms, and an open-concept layout thoughtfully designed for comfortable everyday living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring stainless steel appliances, a breakfast bar, a walk-in pantry, and an adjoining dining area that flows seamlessly into the living room. Elegant ceramic tile extends throughout the main living areas, while the abundant natural light create a bright, inviting atmosphere. The private primary suite offers a generous walk-in closet and an ensuite bath with dual vanities and a large walk-in shower. Two additional bedrooms are thoughtfully positioned toward the front of the home, providing flexibility for guests, a home office, or hobbies. Enjoy Florida living year-round on the private brick-paver patio, with additional upgrades including an epoxy-coated garage floor, overhead storage racks, seamless gutters, upgraded front elevation with brick accents, and a rear-entry garage for enhanced curb appeal. Located in the Waterleigh master-planned community, residents enjoy resort-style amenities including multiple pools, fitness centers, walking trails, parks, playgrounds, sports courts, community gardens, and scenic lakes. Conveniently located near Horizon West, Hamlin Town Center, New Publix, shopping, dining, major roadways, Walt Disney World, and everything Winter Garden has to offer. Don't miss the opportunity to own this move-in-ready home in one of Central Florida's most desirable communities.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Rick Brown (407-393-5901)
2010 BOSS HEWETT ST, WINTER GARDEN, FL 34787
$1,500,00021 Days on yellowkey MLS ID: O6423216
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3781 Built: 2022Monthly Fee: $165 Tax: $11,186 (2025)Community: Hull Island/Oakland Ph 2Single Family
Taxes:$11,186
Elementary School: Tildenville Elem
Middle School: Lakeview Middle
Remarks: Welcome to this stunning, like-new home that perfectly blends luxury, comfort, and modern design in the highly desirable community of Hull Island. Boasting five spacious bedrooms and four full bathrooms, this thoughtfully designed residence offers an ideal layout for both everyday living and entertaining. This home offers two spacious owner’s suites, one conveniently located on the first floor and another upstairs, making it ideal for multigenerational living, extended guests, or added privacy. Step inside to soaring high ceilings and an open-concept floor plan filled with natural light. The heart of the home is the gourmet gas kitchen, featuring 42-inch cabinetry, elegant quartz countertops, a large center island, built-in convection oven, stainless steel appliances and premium finishes throughout. A dedicated beverage station with a separate bar refrigerator provides the perfect space for entertaining guests. Upstairs, you'll find an expansive loft that offers endless possibilities as a media room, game room, home office, or additional living space. Outside, enjoy your own private backyard retreat complete with a sparkling pool, ideal for relaxing or hosting family and friends year-round. The garage is equipped with overhead storage shelving, providing ample space to keep seasonal items and equipment neatly organized. With its spacious layout, upscale finishes, abundant storage, and exceptional amenities, this beautifully maintained home is truly move-in ready and offers the perfect combination of elegance, functionality, and Florida living at its finest. This community features a pool pool, nature trails, playground, dog park, and private dock. Conveniently located near shopping, dining, main highway and more.
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Vilmari Caraballo (407-583-9870)
8506 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787
$1,299,00029 Days on yellowkey MLS ID: O6421255
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3966 Built: 2016Monthly Fee: $380 Tax: $11,330 (2025)Community: Waterleigh Ph 1ASpa: YesSingle Family
Taxes:$11,330
Elementary School: None
Remarks: LAKEFRONT living with TWO PRIMARY SUITES, this one has it all. Tucked into the highly desirable Phase 1 of Waterleigh, this Emerald Homes former model sits right on HICKORYNUT LAKE with unobstructed water views, plus two of the three secondary bedrooms enjoy DISNEY FIREWORKS VIEWS every night. Featuring 5 bedrooms, 5 bathrooms, a tile roof, and an oversized 3 car garage. Inside you'll find wood look tile floors, a flex space perfect for an office or playroom, and a formal dining room. The kitchen features quartz countertops and stainless steel appliances. The casual dining nook overlooks the lake, making every morning coffee feel like a getaway. The first primary suite sits on the main level near the pool bath, with a walk-in closet, soaking tub, and dual sinks with quartz counters, ideal for guests or multigenerational living. Upstairs, the second primary suite steals the show with an elevated lake view, an oversized walk-in closet, and a spa-style bath with dual vanities and a separate water closet. A spacious loft offers an additional living space or game room. Outside, the pool deck sets the stage for sunset evenings by the pool and hot tub overlooking the lake. Waterleigh's HOA takes care of your landscaping and lawn maintenance, and the community offers a resort-style clubhouse pool, mini golf, beach volleyball, walking trails, and a dog park nearby, all just minutes from the 429 and Disney. Schedule your private tour today.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
1642 CHANDELLE LN, WINTER GARDEN, FL 34787
$689,90028 Days on yellowkey MLS ID: G5114093
REDUCED by $20,000 (2.8%) on 07/20/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2918 Built: 2006Monthly Fee: $167 Tax: $8,474 (2025)Community: Belle Meade-Ph I B D & GSpa: NoSingle Family
Taxes:$8,474
Elementary School: Whispering Oak Elem
Remarks: Welcome to this beautifully maintained 5-bedroom, 3-bathroom single-story home in the highly sought-after gated community of Belle Meade — zoned for Whispering Oak Elementary (10/10 GreatSchools rating, top 5% of all schools in Florida), SunRidge Middle, and West Orange High School. With 2,918 square feet of thoughtfully designed living space, a 3-car garage, and a fenced corner lot spanning 0.27 acres, this home offers the space, privacy, and top-tier school access today's families are searching for. Major systems have already been taken care of for you — enjoy true peace of mind with a brand new roof (February 2024), backed by a CertainTeed SureStart warranty that's fully transferable to the new owner, and a brand new Trane 5-ton AC system (2025) with a 10-year warranty through 2035. No surprise repairs, no looming replacements — just move in and relax. Inside, soaring cathedral and vaulted ceilings, tray ceilings, crown molding, and wood flooring create an elegant, open feel throughout. A separate laundry room adds everyday convenience, and the fifth bedroom functions as a versatile den/utility space — ideal for a home office, playroom, or guest suite. The primary suite is a true retreat, featuring dual walk-in closets, dual vanities, a spa-style soaking tub, a separate standing shower, and a private water closet. Step outside to your fully screened and covered patio — perfect for entertaining or simply enjoying Florida's year-round sunshine, rain or shine — overlooking the private, fenced backyard. Belle Meade is a secure, gated community known for its lush landscaping, sidewalks, welcoming neighbors, and an on-site dog park. You're just minutes from Winter Garden Village at Fowler Groves — Central Florida's premier outdoor shopping and dining destination — and a short drive from historic Downtown Winter Garden's Plant Street, home to the award-winning Saturday Farmers Market, Crooked Can Brewing Company, and some of the area's best restaurants. Lake Apopka and several highly rated golf courses, including West Orange Country Club and Orange County National Golf Center (home to PGA Tour and LIV Golf events), are also just minutes away. Commuters and theme park lovers alike will appreciate the unbeatable location: Walt Disney World is approximately 15–25 minutes away via SR 429, with Universal Studios and SeaWorld each roughly 20–30 minutes via the Florida Turnpike. Downtown Orlando is approximately 20–25 minutes away via SR 408 or SR 50, and Orlando International Airport is about 30–35 minutes via the Turnpike. This is a rare opportunity to own a move-in ready home with major systems already updated, zoned for one of Florida's top-rated elementary schools, in one of Winter Garden's most desirable gated communities. Schedule your private showing today!
Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)
Listing Agent: Nikhil Vashist (352-901-3786)
17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787
$620,00030 Days on yellowkey MLS ID: G5114379
REDUCED by $10,000 (1.6%) on 07/05/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2692 Built: 2017Monthly Fee: $215Community: Waterside/Johns Lake Ph 2ASingle Family
Taxes:$0
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: Motivated Seller! Don't miss your opportunity with this Winter Garden home - offering elegance, convenience and affordability. Situated inside the desirable Waterside community, you will find this beautifully designed residence, blending timeless sophistication with modern comfort, offering an open floor plan, designer finishes, and exceptional indoor-outdoor living. From the moment you arrive, the charming covered front porch, mature landscaping, and inviting curb appeal set the tone. Inside, you're greeted by wide-plank luxury vinyl flooring, soaring ceilings, crown molding, and sun-filled living spaces designed for both everyday living and effortless entertaining. The gourmet kitchen is a true showpiece featuring granite countertops, an oversized center island with seating, farmhouse sink, shaker cabinetry, stainless steel appliances, gas cooktop, double ovens, subway tile backsplash, a custom, handmade hood and designer pendant lighting. Flowing seamlessly into the spacious dining area and family room, this home is ideal for gathering with family and friends. Large sliding glass doors open to an expansive covered lanai with a stunning wood-finished ceiling, creating the perfect space to dine outdoors or just relax. The fully fenced backyard provides privacy, while maintaining a low-maintenance lifestyle. As you journey to the second level, you are greeting by a spacious loft, creating a retreat for unwinding and more closet space. Two large, additional bedrooms and a full bathroom are set off from the primary suite. Escape to your luxurious primary suite, offering a spacious walk-in closet and a beautifully upgraded spa-inspired bath, complete with a custom dual-sink vanity with quartz countertops, elegant gold fixtures, an oversized walk-in shower, and designer tile extending to the ceiling. Additional highlights include double-pane windows, custom window treatments, upgraded light fixtures, abundant storage, an oversized laundry room and pantry and thoughtful designer touches throughout. Residents enjoy outstanding resort-style amenities including a lakeside community pool, clubhouse, fitness center, playground, unfenced dog park and community dock. Ideally located in the heart of Winter Garden, this exceptional home is just minutes from shopping, dining, entertainment, theme parks, major highways, and top-rated schools. This isn't just a home; it's a lifestyle. Book your showing today!
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (352-394-5900)
Listing Agent: Wendy Moore (678-575-5596)
17035 HARBOR OAK PKWY, WINTER GARDEN, FL 34787
$485,00058 Days on yellowkey MLS ID: O6411409
REDUCED by $14,999 (3.0%) on 07/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1692 Built: 2017Monthly Fee: $215 Tax: $3,704 (2025)Community: Waterside/Johns Lake Ph 2ASingle Family
Taxes:$3,704
High School: None
Middle School: None
Remarks: Motivated sellers! Welcome to this highly sought-after home in the infamous Waterside Johns Lake. This adorable 3-bedroom, 2-bath home is truly a gem! This freshly painted home has delightful curb appeal, featuring an oasis of flowers and shrubs and a charming porch, perfect for sitting out and savoring life as it passes. This open floor plan is enhanced by modern high-end finishes throughout. The kitchen boasts of like-new cabinets, quartz countertops, stainless steel appliances, a walk-in pantry, and an oversized kitchen island that overlooks the family room, with the dining area conveniently located just off the kitchen, great for entertaining! The ceramic tile runs throughout with luxury Vinal plank fitted floors in two of the bedrooms. The living areas flow seamlessly together, creating an inviting space for everyday use. The primary suite offers both comfort and convenience, complete with a generous walk-in closet, dual vanities, quartz counters, and a walk-in shower. The laundry room is spacious and comes with a separate washer and dryer. The garage is located next to the laundry room, providing direct access into your home. Sliding doors open onto your own screened-in patio, perfect for enjoying the evenings or grilling out. This home has a newer roof 2025, a new tankless water heater 2026. Waterside at Johns Lake offers resort-style amenities, including a fully equipped gym, large well maintained swimming pool and a club house, this is all located just over the street for your convenience. There is easy access to all major highways including 429 and Florida's Turnpike for seamless access to downtown Orlando, area theme parks, and Orlando International Airport. Schedule your showing today! This won't last long.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Heidi Pfeffer-Morgan (407-408-6101)
15717 E OAKLAND AVE, WINTER GARDEN, FL 34787
$1,795,00022 Days on yellowkey MLS ID: O6419032
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3515 Built: 1997 Tax: $6,623 (2025)Community: OaklandSingle Family
Taxes:$6,623
Remarks: Welcome to this exceptional ONE-OWNER CUSTOM HOME, sitting on a ONE-ACRE HOMESITE in one of Oakland’s most sought-after locations. Offering 3,515 square feet of living space (4,890 total square feet), this thoughtfully designed 4-bedroom, 3.5-bath residence combines timeless Old Florida charm with OUTSTANDING QUALITY CONSTRUCTION, FEATURING ALL-STEEL CONSTRUCTION—INCLUDING STEEL ROOF TRUSSES—for exceptional durability and peace of mind. A circular driveway and side-entry OVERSIZED TWO-CAR GARAGE create impressive curb appeal, while double front doors welcome you into a spacious, OPEN FLOOR PLAN with 17.5' VAULTED CEILINGS in living area and 10' CEILING HEIGHT in bedrooms.This home has been designed for both everyday living and entertaining. At the heart of the home is a stunning DOUBLE-SIDED FIREPLACE with Tennessee Stone which creates a beautiful focal point between the formal living room and the inviting family room. The living areas flows seamlessly into the kitchen, separated only by a short wall between the kitchen and dining room that preserves the home’s open, airy feel. The EXPANSIVE KITCHEN is designed to bring everyone together, featuring TWO SINKS, a WRAPAROUND BREAKFAST BAR with seating for up to eight, a center ISLAND WITH COOKTOP, generous eat-in dining area, WALK-IN PANTRY with custom built-in shelving, and abundant countertop workspace. The open layout allows the kitchen, dining, and living areas to remain connected, making this home ideal for entertaining, holidays, and family gatherings. The desirable THREE-WAY SPLIT FLOOR PLAN offers both privacy and flexibility. Two secondary bedrooms and a full bath are located toward the front of the home, while a separate guest wing features an additional bedroom, full bath, oversized laundry room with storage, and a convenient half bath. Privately tucked away on the opposite side of the home, the spacious primary suite offers two walk-in closets and an ensuite bath with a walk-in shower. Double glass doors open to an expansive screened lanai that extends the living space outdoors, complete with a summer kitchen and peaceful views of the lush backyard. Additional updates include a tile roof (2015), HVAC ductwork (2020), exterior stucco upgrades and fresh paint (2021), one water heater replaced in 2018 and the second in February 2025, Connection to city water in 2019, The well was retained exclusively for lawn irrigation. Perfectly located with convenient access to the Florida Turnpike, Highway 50, shopping, dining, and area attractions. This meticulously maintained custom home offers the rare combination of quality construction, timeless design, generous living spaces, and an unbeatable Oakland location. This is Florida living at its finest.
Listing is courtesy of: CARIS REALTY AND INVESTMENTS INC (407-595-0009)
Listing Agent: Janelle Conway (407-595-0009)
8150 RED STOPPER LN, WINTER GARDEN, FL 34787
$429,90022 Days on yellowkey MLS ID: O6416867
REDUCED by $10,000 (2.3%) on 07/24/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1738 Built: 2018Monthly Fee: $315 Tax: $7,091 (2025)Community: SummerlakeTownhouse
Taxes:$7,091
Elementary School: Summerlake Elementary
Remarks: Virtually Staged. OBTAINABLE LUXURY IN SUMMERLAKE! This MOVE-IN-READY, Energy Star Certified townhome offers the perfect blend of style, comfort, luxury and convenience with 3 bedrooms, 2.5 baths, a 2-car garage, and 1,738 square feet of thoughtfully designed living space. Recently refreshed with NEW interior PAINT and NEW CARPETING, this home welcomes you from the moment you step onto the covered front porch. Inside, the open-concept floor plan is enhanced by contemporary wood-look tile flooring throughout the first level, creating a warm and inviting atmosphere. The spacious living and dining areas flow seamlessly into the beautifully appointed kitchen featuring granite countertops, rich 42-inch wood cabinetry, stainless steel appliances, a large center island with sink and breakfast bar, walk-in pantry, and a convenient built-in desk workspace. Whether preparing meals or entertaining guests, the open design keeps everyone connected. Step outside to your private, partially fenced courtyard with brick pavers—an ideal setting for morning coffee, outdoor dining, or relaxing after a busy day. The courtyard leads directly to the detached 2-car garage for added convenience. Upstairs, you'll find all three bedrooms, the laundry area, and new carpeting throughout. The spacious primary suite easily accommodates a king-size bed and features a large walk-in closet and an en-suite bath with dual granite vanities, a garden tub, and separate shower. Two additional bedrooms share a full bath with granite countertops. Located in the highly desirable Summerlake community, residents enjoy outstanding resort-style amenities including a community pool, clubhouse with fitness center and recreation room, pickleball/tennis and basketball courts, playgrounds, zip line, parks, dog park, and scenic walking trails. The home is conveniently located near Summerlake Elementary School and a neighborhood park. Summerlake, Hamlin and Horizon schools were all A rated for the 2024/2025 school year!! As an added entertainment bonus, enjoy spectacular nightly Disney fireworks from designated viewing areas throughout the community. Just minutes from Hamlin Town Center, Cinépolis Luxury Cinemas, Orange County National Golf Center & Lodge, shopping, dining, and major roadways. This luxurious, beautifully updated home offers an exceptional opportunity to enjoy one of Horizon West's most sought-after communities. Experience the perfect combination of modern comfort, recent updates, and an outstanding Florida lifestyle. Lawn maintenance is included. Exterior scheduled to be painted!
Listing is courtesy of: UPSIDE REAL ESTATE INC (407-308-5750)
Listing Agent: Ann Wargo (407-616-3041)
769 HOME GROVE DR, WINTER GARDEN, FL 34787
$524,50020 Days on yellowkey MLS ID: O6420766
0 Days Off yellowkey (back on 7/25/2026)
REDUCED by $5,500 (1.0%) on 07/24/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2305 Built: 2005Monthly Fee: $99 Tax: $4,372 (2025)Community: Regency Oaks Ph 02 A-CSingle Family
Taxes:$4,372
Remarks: Under contract-accepting backup offers. Price Improvement! Seller says Sell it! Offering $5,000 Buyers Incentive at closing. Welcome to established Regency Oaks subdivision in Stonecrest, in the heart of Winter Garden! Situated on a desirable corner lot, this screened-in POOL home offers an incredibly flexible floor plan designed to fit today's lifestyle. Listed as a 3-bedroom home, it also features a spacious flex room overlooking the pool and backyard, along with a separate oversized bonus room that can easily serve as an additional bedroom, home office, media room, playroom, fitness studio, guest retreat, or additional living space. The split-bedroom layout provides privacy, while the primary suite features a walk-in closet, garden tub, and separate shower. Fresh interior paint and updated laminate flooring enhance the home's inviting feel. Step outside to your private backyard oasis complete with a sparkling pool, mature shade trees, a side yard for gardening and a pool safety fence—creating the perfect setting for entertaining or relaxing while enjoying Florida's indoor-outdoor lifestyle. Recent improvements include a new roof (2023), 2017 air handler, 2018 A/C condenser, and a recently serviced irrigation system for added peace of mind. Residents of Regency Oaks enjoy low monthly HOA fees and outstanding community amenities including scenic walking trails around a picturesque pond with benches, a clubhouse, community pool, and two neighborhood parks/playgrounds. Ideally located walking distance of Winter Garden Village at The Grove and just minutes from Historic Downtown Winter Garden, the West Orange Trail, major highways, shopping, dining, entertainment, top rated schools and Central Florida's world-famous attractions. Orlando International Airport and Florida's east coast beaches are both approximately an hour away.
Listing is courtesy of: METRO CITY REALTY (407-237-3331)
Listing Agent: Beatrice Miranda (407-592-4448)
15587 HAMLIN BLOSSOM AVE, WINTER GARDEN, FL 34787
$619,90034 Days on yellowkey MLS ID: O6418163
1 Days Off yellowkey (back on 7/25/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1860 Built: 2015Monthly Fee: $235 Tax: $7,423 (2025)Community: Hickory Hammock Ph 2ASingle Family
Taxes:$7,423
Remarks: Under contract-accepting backup offers. SHOW STOPPER! Welcome to 15587 Hamlin Blossom - in the highly sought-after gated community of HICKORY HAMMOCK. A rare find, this Ashford model by M/I Homes is one of only six Ashford floor plans built in the community. Every detail of the 1860 sq. ft has been thoughtfully designed and meticulously cared-for, creating a TURNKEY experience unlike any other. Start off on your paver driveway and enjoy the handpicked lush new landscaping and welcoming porch-sitting area where you can immediately enjoy the outdoor Florida lifestyle. NEW EXTERIOR PAINT. Once inside you are greeted with perfection. NEW luxury vinyl flooring in each bedroom. NO CARPETS throughout the entire SINGLE STORY home. A foyer that immediately impresses with crafted lighting fixtures and perfectly placed decor. SPLIT FLOOR PLAN creates privacy for the two bedrooms and bath in the front of the home. Double vanity with UPGRADED lighting and hardware to elevate the bathroom space. The OPEN FLOORPLAN and dining room/living room combo is perfect for entertaining guests. Create the ideal ambiance with your ALEXA-enabled recessed lighting. A chef’s dream kitchen with BRAND NEW refrigerator, NEW dishwasher, and NEW garbage disposal. The primary suite is perfectly appointed with classic upgrades and reading nook. The HIGHLIGHT of the home is the wraparound paver patio with outdoor living/dining room space and OUTDOOR KITCHEN all under a screen enclosure overlooking a fully fenced, newly landscaped outdoor and garden area. Other upgrades include NEW washer/dryer, NEW HVAC components, NEW TESLA charging station. Hickory Hammock is a special enclave of Winter Garden that overlooks John’s Lake. Residents enjoy water views, private fishing pier, tennis courts, beach volleyball courts, nature trails, resort-sized swimming pool, fitness center, clubhouse, and nature trails. Located in the heart of Winter Garden and Horizon West, this home is approximately 5 minutes from SR 429, 10 minutes from Hamlin Town Center, 10 minutes from Downtown Winter Garden, and approximately 25 minutes from Walt Disney World. Residents enjoy convenient access to shopping, dining, entertainment, top-rated schools, major employment centers, and everything that makes Winter Garden one of Central Florida's most desirable places to live. Contact list agent for full list of upgrades AND seller’s complete maintenance schedule/records. Homes this well cared for do not come on the market often. See it for yourself today!
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Michelle Zimmerman (732-616-6019)
6323 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787
$560,00049 Days on yellowkey MLS ID: O6415343
REDUCED by $10,000 (1.8%) on 06/19/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2177 Built: 2018Monthly Fee: $425 Tax: $8,526 (2025)Community: Hamlin ReserveSingle Family
Taxes:$8,526
Elementary School: Independence Elementary
Middle School: Bridgewater Middle
Remarks: Looking for a move-in ready home near Hamlin in Winter Garden with a private backyard and low-maintenance interior? This 3-bedroom, 2.5-bath residence in Hamlin Reserve offers exactly that. A covered brick paver patio overlooks an expansive, fenced backyard, offering rare outdoor space for relaxing, entertaining, or simply enjoying more privacy. Inside, wood-look tile and luxury vinyl flooring run throughout, with no carpet anywhere in the home. The kitchen features black cabinetry, quartz countertops, and stainless steel appliances, opening into a flexible living and dining layout with strong natural light. Upstairs, the primary suite includes a walk-in closet and private bath, with additional bedrooms suited for family, guests, or a home office. Hamlin Reserve is one of Winter Garden's most convenient communities, with a pool, park, playground, and dog park, minutes from Hamlin, SR 429, shopping, dining, and medical facilities. The property is zoned for Independence Elementary, Bridgewater Middle, and Horizon High School. Schedule your showing to see the layout, storage, and outdoor space in person.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Jessica Souza Meuli (305-527-9574)
17631 LAKE STAR RD, WINTER GARDEN, FL 34787
$830,1865 Days on yellowkey MLS ID: TB8532670
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3004 Built: 2026Monthly Fee: $84 Tax: $11,000 (2025)Community: Northlake At OvationSingle Family
Taxes:$11,000
Remarks: Under Construction. Welcome to Northlake at Ovation! This gorgeous new construction home is located in the highly desirable Horizon West area of Winter Garden. This beautiful two story home features 3 bedrooms, 3 baths and flexible loft space. The open kitchen boasts plenty of upgrades from the AW Collection Milan such as beautiful 42 inch cabinets, tiled backsplash, and stainless steel appliances. Large island with upgraded quartz countertops perfect for gatherings that is open to the family room with soaring two story ceiling with plenty of windows bringing in natural light throughout. Main living space features wood look tile flooring and bedrooms with upgraded carpet for comfort, plus 8' interior and exterior doors throughout the home. Enjoy the amenities with a swim in the community pool, clubhouse, shaded playground, and dog park. This home is conveniently located to top rated schools, shopping, grocery stores, Horizon West restaurants, and Walt Disney World. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.
Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC (813-918-4491)
Listing Agent: Reed Williams (813-918-4491)
6274 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$1,016,0605 Days on yellowkey MLS ID: G5115512
0 Days Off yellowkey (back on 7/24/2026)
Bed: 6 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4236 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Remarks: Virtually Staged. Pre-Construction. To be built. Welcome to the Arlington with Bonus! This stunning 4236 square foot, two-story floor plan boasts 6 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends. The garage includes an extra hobby/work space for all your creative projects. Step outside and unwind under the inviting covered patio, or head upstairs to discover a generously sized bonus room, ideal for a playroom, home office, or media space. Don’t miss out on the opportunity to make this beautiful home your own!
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
13852 JOMATT LOOP, WINTER GARDEN, FL 34787
$1,030,0005 Days on yellowkey MLS ID: O6427925
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4000 Built: 2016Monthly Fee: $75 Tax: $7,387 (2025)Community: Cypress Reserve Ph 1Spa: YesSingle Family
Taxes:$7,387
Remarks: Welcome to luxury living at its finest! Perfectly positioned on the largest homesite in the community, this exceptional 4 bedroom home, fully equipped with oversized loft and theatre/bonus room, sits on a premium 1/3-acre oversized lot with tranquil green space views, offering both privacy and room to enjoy Florida living. From the moment you arrive, you’ll be impressed by the freshly painted exterior, upgraded landscaping, elegant stone accents, and expansive paver driveway. Inside, thoughtful upgrades and quality craftsmanship are showcased throughout, including 8-foot interior doors, crown molding, custom window casings and sills, upgraded wood flooring, premium carpeting, and designer tray ceilings in both the dining room and the luxurious owner’s suite. The heart of the home is the stunning gourmet kitchen, featuring upgraded cabinetry, a California-style countertop, a vented exterior range hood, motion-activated faucet, and abundant space for entertaining and everyday living. The spacious owner’s retreat provides a peaceful escape with its elegant tray ceiling and spa-like atmosphere, while the open-concept layout is designed for both comfort and entertaining. This home is full of valuable efficiency upgrades, including a radiant barrier roof for exceptionally low energy costs, gutters, and numerous quality enhancements that provide peace of mind for years to come. This is a rare opportunity to own one of the community’s most desirable homesites, combining luxury finishes, energy efficiency, and an unbeatable oversized lot with beautiful green space views. A truly exceptional home, with LOW HOA and A RATED SCHOOL-ZONES that is as impressive inside as it is out. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Jenna Palmero (407-697-8727)
15190 SUNRISE GROVE CT, WINTER GARDEN, FL 34787
$435,0005 Days on yellowkey MLS ID: O6427822
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1902 Built: 2018Monthly Fee: $346 Tax: $5,755 (2025)Community: Hickory Hammock Phase 2BTownhouse
Taxes:$5,755
Middle School: Horizon West Middle School
Remarks: Welcome to this beautifully maintained end-unit townhome in the highly sought-after Hickory Hammock at Johns Lake! Filled with natural light from additional windows and offering extra green space rarely found with townhome living, this move-in-ready home combines comfort, style, and an unbeatable Winter Garden location. The open-concept floor plan features a spacious great room, dining area, and a well-appointed kitchen with granite countertops, stainless steel appliances, and abundant cabinet space—perfect for everyday living and entertaining. Upstairs, the private primary suite provides a relaxing retreat, while two additional bedrooms and an upstairs laundry room offer comfort and convenience for family and guests. Enjoy peaceful mornings or relaxing evenings on the covered patio overlooking lush green space. Hickory Hammock is a gated, virtual guard community surrounded by Johns Lake, Lake Burnett, and Lake Claire, offering resort-style amenities including a community pool, clubhouse, fitness center, tennis courts, sand volleyball, dog park, playgrounds, parks, and a community fishing pier. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, SR-429, the Florida Turnpike, top-rated schools, shopping, dining, and Central Florida's world-famous attractions, this home offers the perfect blend of convenience and lifestyle. Don't miss this exceptional opportunity—schedule your private showing today!
Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)
Listing Agent: Corey Smallman (407-744-2765)
16130 WIND VIEW LN, WINTER GARDEN, FL 34787
$550,0005 Days on yellowkey MLS ID: O6412051
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2031 Built: 2016Monthly Fee: $344 Tax: $9,012 (2025)Community: Waterleigh Ph 1BSingle Family
Taxes:$9,012
Elementary School: Panther Lake Elementary
Remarks: Welcome to your beautiful water-view home in the highly sought-after Waterleigh community! This stunning property offers the convenience of single-story living with 4 bedrooms, 3 full bathrooms and picturesque water views. Perfectly positioned with a large green space in front and stunning pond and lake views in the back, this home features a gated backyard offering added privacy and convenient outdoor access. End your evenings by enjoying a glimpse of Disney's nightly fireworks right from your own backyard. Inside, you'll find numerous recent updates, including a new HVAC system, brand-new carpet, a new refrigerator, new dishwasher, new garbage disposal, and a new washer and dryer, making this home truly move-in ready! One of the many perks of living in Waterleigh is that lawn care is included in the HOA, allowing you to spend more time enjoying the exceptional resort-style amenities. Residents have access to resort-style pools, state-of-the-art fitness centers, beautiful clubhouses, mini golf, a dog park, expansive sports fields, multiple playgrounds, beach volleyball, tennis courts, a community dock, and scenic walking trails and picnic areas, creating the perfect setting for an active and relaxing lifestyle. Ideally located in the heart of Horizon West, just minutes from Walt Disney World with quick access to SR-429, this home offers easy commuting throughout Central Florida while being zoned for highly rated schools. This is a rare opportunity to own a beautifully updated home with exceptional views in one of Horizon West's most desirable communities. Schedule your private showing today!
Listing Agent: Erica Jefferson (414-248-9118)
9718 QUIET LN, WINTER GARDEN, FL 34787
$1,300,0007 Days on yellowkey MLS ID: O6427038
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2738 Built: 2001Monthly Fee: $17 Tax: $5,389 (2025)Community: Valley ViewSpa: YesSingle Family
Taxes:$5,389
Elementary School: Lost Lake Elem
High School: East Ridge High
Middle School: Windy Hill Middle
Remarks: Under contract-accepting backup offers. Tucked away on a quiet country lane, hidden behind lush mature landscaping and embraced by five private acres, this exceptional Konkol Custom Homes estate at 9718 Quiet Lane is more than a home. It is a sanctuary. A place where mornings begin with birdsong, afternoons are spent watching butterflies drift through the wildflower garden, and evenings end around the fire pit beneath a canopy of stars. Designed for both everyday living and effortless entertaining, this beautifully maintained residence offers a desirable three-way split floor plan with four bedrooms on the main level. Thoughtfully designed desk areas in each of the secondary bedrooms provide dedicated spaces for studying, working from home, or creative pursuits, making the home as functional as it is beautiful. The owner's retreat serves as a peaceful haven, complete with a private office, gym, or nursery, an expansive walk-in closet, and a beautifully updated spa-inspired bath. At the heart of the home, the thoughtfully renovated kitchen overlooks the inviting family room and fireplace, showcasing stunning leathered quartzite countertops, adding warmth, texture, and timeless sophistication throughout the living spaces. The renovated secondary bath with polished quartzite offers both style and convenience for family and guests alike. Upstairs, a generous bonus room with a full bath offers endless possibilities as a fifth bedroom, home theater, game room, craft studio, or private guest suite. An oversized walk-in floored attic provides exceptional storage today while offering exciting potential for future expansion. Step outside and discover where this property truly comes alive. The screened saltwater pool and heated spa create a private resort overlooking the peaceful acreage beyond. Wander through vibrant wildflower gardens, gather around the fire pit with family and friends, or simply unwind while birds, butterflies, and bunny rabbits make their daily appearances. Every inch of the grounds has been thoughtfully cultivated to create a setting that feels worlds away from the pace of everyday life. Additional features include a circular driveway, side-entry garage, storage shed, and complete privacy from the street. Yet despite its secluded ambiance, this remarkable estate enjoys one of Winter Garden's most sought-after locations, perfectly situated between Historic Downtown Winter Garden and Hamlin with convenient access to State Road 429 and everything Central Florida has to offer. If you've been searching for a place to escape the hustle and bustle without sacrificing convenience, welcome home to your own private refuge.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Matthew Mckee (407-948-0658)
11025 SUSPENSE DR, WINTER GARDEN, FL 34787
$419,90058 Days on yellowkey MLS ID: G5113196
REDUCED by $15,100 (3.5%) on 06/14/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1636 Built: 2017Monthly Fee: $263 Tax: $5,322 (2025)Community: Storey Grove Ph 1B-1Townhouse
Taxes:$5,322
Remarks: Beautifully maintained and thoughtfully upgraded townhome in the Storey Grove community of Winter Garden. This 3-bedroom, 2.5-bath residence features an open-concept floor plan, quartz countertops, stainless steel appliances, a spacious primary suite, and a private two-car garage. Recent improvements include a whole-home water softener system, whole-home electrical surge protection, and two dedicated electric vehicle charging stations. Residents have access to community amenities including a pool, fitness center, walking trails, playgrounds, and parks. Conveniently located near shopping, dining, entertainment, major roadways, and area attractions.
Listing is courtesy of: SCATES REALTY & INVESTMENT PRO (352-404-8960)
Listing Agent: Carla Connelly (352-805-8650)
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
Taxes:$11,924
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)
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