Location: Winter Garden
Do Not Show Listings
16802 OAKBORO ST, WINTER GARDEN, FL 34787
$500,0006 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,269
Elementary School: Water Spring Elementary
High School: Horizon High School
Tax Year: 2025
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
$1,500,00019 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
High School: West Orange High
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
$1,299,00027 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
$689,90026 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
Middle School: SunRidge Middle
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
$620,00028 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)
132 ZACHARY WADE ST, WINTER GARDEN, FL 34787
$515,00031 Days on yellowkey MLS ID: O6411394
REDUCED by $10,000 (1.9%) on 07/22/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1708 Built: 2002Monthly Fee: $67 Tax: $3,813 (2025)Community: Lakeview Reserve 46/149Spa: NoSingle Family
Taxes:$3,813
Remarks: Located in the Golf Cart District and less than one mile from Historic Downtown Winter Garden and directly across from the West Orange Trail, this beautifully maintained 3 bedroom, 2 bath home in the Gated Community of Lakeview Reserve offers the perfect blend of location, comfort, and updates. The desirable split floor plan features spacious living and dining areas with an open concept kitchen at the heart of the home. Large windows throughout provide abundant natural light, while the kitchen offers a cozy breakfast nook and overlooks the backyard. The primary suite is a private retreat featuring a custom wood accent wall, soaking tub, and separate walk in shower. Two additional bedrooms are situated on the opposite side of the home, providing privacy for family or guests. Step outside to enjoy the spacious fenced backyard and screened lanai, perfect for relaxing or entertaining. Recent updates include a new roof (2018), exterior paint (2018), fence (2022), screened lanai (2022), gutters (2022), new sod (2025), and brand new carpet. Residents of Lakeview Reserve enjoy the security of a gated entrance, a covered community dock with scenic lakefront seating, and a prime location near shopping, dining, and all that Downtown Winter Garden has to offer. Top rated elementary and middle schools are within walking distance, making this move in ready home an exceptional opportunity in one of Central Florida's most sought after communities.
Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)
Listing Agent: Jennifer Mitchell (803-414-1133)
17035 HARBOR OAK PKWY, WINTER GARDEN, FL 34787
$485,00056 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)
5973 CYPRESS HILL RD, WINTER GARDEN, FL 34787
$734,90057 Days on yellowkey MLS ID: O6412179
REDUCED by $5,100 (0.7%) on 07/21/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3532 Built: 2017Monthly Fee: $195 Tax: $9,630 (2025)Community: IndependneceSingle Family
Taxes:$9,630
Elementary School: Independence Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Welcome to 5973 Cypress Hill Road, an exceptional 5-bedroom, 3.5-bathroom home offering nearly 3,500 square feet of thoughtfully designed living space in the highly sought-after Independence community of Winter Garden. Located in the heart of Horizon West, one of Central Florida's fastest-growing and most desirable areas, this move-in-ready home combines spacious living, resort-style amenities, top-rated schools, and unbeatable convenience. Seller is willing to help with buyers closing costs Step inside and discover a versatile floor plan designed for today's lifestyle. Multiple living spaces, including a formal living room, family room, and great room, provide the flexibility needed for entertaining, working from home, multigenerational living, or simply enjoying time with family. The spacious first-floor primary suite offers a private retreat away from the secondary bedrooms, while each of the five bedrooms features its own walk-in closet, abundant natural light, and comfortable carpeting. With room for everyone and everything, this home delivers the space buyers are searching for. At the heart of the home, the kitchen features stainless steel appliances, ample cabinetry, tile flooring, and generous workspace for meal preparation and entertaining. The washer, dryer, and all kitchen appliances convey with the sale, making your transition seamless. Step outside to the screened lanai and enjoy Florida living year-round. Whether you're enjoying your morning coffee, hosting weekend barbecues, or unwinding after a long day, this outdoor living space provides the perfect setting. Additional highlights include a newer HVAC system, a two-car garage, ceramic tile flooring in the main living areas, and abundant storage throughout the home. Residents of Independence enjoy access to an impressive collection of community amenities, including resort-style swimming pools, a fitness center, parks, playgrounds, walking trails, sports courts, and year-round community events. The location places you just minutes from Hamlin Town Center, downtown Winter Garden, shopping, dining, entertainment, major highways, and world-renowned attractions including Walt Disney World. Families will appreciate the home's location within the highly regarded school zones for Independence Elementary, Bridgewater Middle School, and Windermere High School. If you've been searching for a spacious Winter Garden home for sale with a downstairs primary suite, walk-in closets in every bedroom, resort-style community amenities, and convenient access to everything Central Florida has to offer, 5973 Cypress Hill Road deserves a spot at the top of your list. Schedule your private showing today and experience the Independence lifestyle for yourself. All information provided is deemed reliable but not guaranteed. All buyers should verify all information provided
Listing is courtesy of: NEARBY REALTY (407-349-7533)
Listing Agent: Michael Ellingson (970-978-8101)
11031 JACKSON CV, WINTER GARDEN, FL 34787
$715,00011 Days on yellowkey MLS ID: O6425544
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2931 Built: 2023Monthly Fee: $300 Tax: $10,935 (2025)Community: Waterleigh Ph 4B & 4CSingle Family
Taxes:$10,935
Remarks: Virtually Staged. Experience the highly sought-after KENTON FLOOR PLAN in the award-winning WATERLEIGH community, just MINUTES FROM DISNEY! Ideally situated on a QUIET CUL-DE-SAC with NO THROUGH TRAFFIC, this beautifully upgraded 4 BEDROOM, 3 BATHROOM home offers WOOD-LOOK TILE throughout the main living areas and LUXURY VINYL PLANK upstairs. Enjoy the unique opportunity to WATCH ROCKET LAUNCHES from your own backyard. A welcoming foyer with TRAY CEILING opens to a versatile FLEX ROOM, perfect for a home office or formal dining room. The OPEN-CONCEPT design centers around a stunning GOURMET KITCHEN featuring 42" UPGRADED SHAKER CABINETS WITH CROWN MOLDING, QUARTZ COUNTERTOPS, UPGRADED TILE BACKSPLASH, 7' ISLAND, STAINLESS STEEL APPLIANCES, VENT HOOD, WALL OVEN & MICROWAVE COMBO, 5-BURNER COOKTOP, OVERSIZED SINGLE-BASIN SINK, WALK-IN PANTRY, plus a built-in COFFEE BAR/DROP ZONE. The spacious family room overlooks the covered lanai and backyard. A FIRST-FLOOR BEDROOM & FULL BATH provide the perfect guest or multigenerational suite. Upstairs, the PRIMARY SUITE features a TRAY CEILING, spa-inspired bath with GARDEN TUB, GLASS-ENCLOSED SHOWER, DUAL QUARTZ VANITIES, and an OVERSIZED WALK-IN CLOSET. A large LOFT offers the perfect space for a media room or playroom. Bedrooms 3 and 4 share a bath with DOUBLE SINKS, while the oversized laundry room includes a UTILITY SINK, WASHER & DRYER. Additional upgrades include BLOCK-ON-BLOCK CONSTRUCTION, WHOLE-HOUSE WATER FILTRATION, REVERSE OSMOSIS SYSTEM, UPGRADED LIGHTING & FANS, VIDEO DOORBELL, LOW-E DOUBLE-PANE WINDOWS, R-30 INSULATION, and RECLAIMED WATER IRRIGATION for outstanding energy efficiency. Enjoy MAINTENANCE-FREE LIVING with lawn care included and access to 4 RESORT-STYLE POOLS, 3 CLUBHOUSES, FITNESS CENTERS, TENNIS COURTS, FISHING PIER, PLAYGROUNDS, PARKS, WALKING TRAILS, and more. WATER SPRING ELEMENTARY and WATER SPRING MIDDLE SCHOOL are just a SHORT WALK AWAY, making everyday routines incredibly convenient. Zoned for HORIZON HIGH SCHOOL and ideally located near shopping, dining, Disney, and with easy access to 429, 417 & 408, this home offers the perfect blend of luxury, convenience, and lifestyle.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Sabrina Freeman (407-446-5541)
5079 PALMETTO PARK DR, WINTER GARDEN, FL 34787
$930,00017 Days on yellowkey MLS ID: G5114492
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3866 Built: 2017Monthly Fee: $190 Tax: $6,877 (2026)Community: Orchard Hills Ph 3Single Family
Taxes:$6,877
Elementary School: Keene Crossing Elementary
Tax Year: 2026
Remarks: Welcome to this beautifully maintained 5-bedroom, 3.5-bath home with a spacious 3-car garage, offering the perfect blend of comfort, style, energy efficiency, and location. From the moment you step inside, you’ll appreciate the soaring ceilings, open living spaces, and thoughtful upgrades throughout. The custom stone fireplace, bring an inviting ambiance to those cozy evenings or when entertaining guests year round. At the heart of the home is the gourmet kitchen, featuring granite countertops, built-in appliances, abundant cabinetry, and plenty of space for cooking and entertaining. The adjoining living area is highlighted by a built-in fireplace, creating a warm and inviting focal point for family gatherings. One of the home’s standout features is the fully owned solar system, helping keep monthly electric costs exceptionally low—averaging approximately $33 per month. The exterior has been recently painted, adding fresh curb appeal. Step outside to the expansive backyard designed with possibilities in mind. The generous outdoor space offers ample room to add a pool whilst still leaving plenty of space for a dedicated grilling and outdoor dining area. Whether you're hosting summer barbecues, family gatherings or relaxing with friends, the spacious yard provides the ideal setting for creating your own private outdoor retreat. The modern floor plan offers five bedrooms and 3.5 bathrooms, providing flexibility for families, guests, or a home office, along with a generous 3-car garage for vehicles and additional storage. Ideally located in one of Winter Garden’s most desirable communities, this home is zoned for highly rated schools and offers convenient access to Walt Disney World, SR-429, downtown Orlando, and Orlando International Airport (MCO), making commuting, travel, shopping, dining, and entertainment easily accessible. If you’re looking for a move-in-ready home with premium features, exceptional energy savings, generous living space, and an outstanding location, this home is ready to welcome you.
Listing is courtesy of: FLORIDA PLUS REALTY, LLC (352-901-9100)
Listing Agent: Claire Brooks (407-967-5829)
1808 WESTERN TRAILWAY DR, WINTER GARDEN, FL 34787
$599,00020 Days on yellowkey MLS ID: S5152973
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1860 Built: 2019Monthly Fee: $165 Tax: $8,389 (2025)Community: Hull Island/OaklandSpa: NoSingle Family
Taxes:$8,389
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home offering over 1,800 square feet of thoughtfully designed living space in the highly sought-after Hull Island community of Oakland. Tasteful décor and stylish finishes create a warm, inviting atmosphere, while the open-concept floor plan features a spacious kitchen with stainless steel appliances, a large center island with counter seating, and seamless flow into the living and dining areas—perfect for everyday living and entertaining. Step outside to your private backyard featuring maintenance-free turf, providing a lush, green outdoor space you can enjoy year-round without the upkeep. Residents also enjoy access to the community pool, scenic walking trails, and direct access to the West Orange Trail, with beautiful Lake Apopka just a couple of blocks away. Best of all, you’ll enjoy all these incredible amenities while benefiting from a LOW HOA FEE! Whether you’re purchasing your first home, growing your family, or right-sizing after the kids have moved out, this home offers the perfect combination of comfort, convenience, and low-maintenance living. Hull Island is a welcoming, family-oriented community for all ages, conveniently located near charming downtown Winter Garden, shopping, dining, parks, and major roadways. Don’t miss your opportunity to make this move-in-ready home your own!
Listing is courtesy of: FLORIDA IN MOTION REALTY INC (407-947-2757)
Listing Agent: Susan Koptieff (407-334-7770)
15717 E OAKLAND AVE, WINTER GARDEN, FL 34787
$1,795,00020 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)
14014 SCARLET ASTER ALY, WINTER GARDEN, FL 34787
$469,00024 Days on yellowkey MLS ID: O6418814
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1808 Built: 2024Monthly Fee: $350 Tax: $6,350 (2025)Community: Harvest/OvationSpa: NoTownhouse
Taxes:$6,350
Remarks: Rare Dual Owner's Suite Townhome — Priced to Move, Near Disney This 3-bedroom, 3-bath, 1,808 sq ft Newton model townhome in Harvest at Ovation is one of the best values in the community right now. Built in 2024 and less than 2 years old, it shows like a model and is ready for immediate move-in, while comparable new construction in the area runs 7+ months out. What sets this home apart is its dual owner's suite layout, a rare find at this price point, with one suite offering a private balcony retreat overlooking the pond, with peaceful water views and nightly glimpses of Magic Kingdom fireworks. Step outside to your own covered patio, a comfortable outdoor living space perfect for everyday relaxation and entertaining. Upgraded flooring and fixtures run throughout, adding a polished, elevated feel without the premium price tag typically attached to that level of finish. Enjoy a community pool and playground, less than 10 minutes from Walt Disney World in one of Central Florida's fastest-growing corridors. With Winter Garden's shopping and dining nearby, this home offers exceptional value for buyers and investors who know the market. This home also includes a transferable 2-10 Pinnacle home warranty (active through May 2027) with zero service history, giving buyers added peace of mind on top of the builder's coverage. Priced competitively for a fast sale. Schedule your showing today.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jarrett Brown (407-787-7589)
8150 RED STOPPER LN, WINTER GARDEN, FL 34787
$429,90020 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)
914 TROWMAN ALY, WINTER GARDEN, FL 34787
$625,00062 Days on yellowkey MLS ID: O6410871
REDUCED by $24,000 (3.7%) on 07/14/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1642 Built: 2022Monthly Fee: $356 Tax: $6,421 (2025)Community: Oakland ParkSingle Family
Taxes:$6,421
Remarks: Looking for a move-in ready home in Winter Garden with modern upgrades, an ideal location, and a true sense of community? Welcome to this beautifully maintained 3-bedroom, 3-bathroom home in the highly desirable Oakland Park neighborhood. Designed for today's lifestyle, this home features a bright open-concept floor plan, abundant natural light, spacious living areas, and a functional layout that's perfect for both everyday living and entertaining. Premium upgrades include gas appliances, elegant plantation shutters, and stylish finishes throughout, offering a turnkey, low-maintenance home you can enjoy from day one. Located in one of Winter Garden's most sought-after golf cart communities, Oakland Park offers resort-style amenities, scenic trails, parks, green spaces, and top-rated schools, creating the perfect setting for an active, connected lifestyle. Just minutes from Historic Downtown Winter Garden, you'll have easy access to the nationally recognized farmers market, local restaurants, boutique shopping, coffee shops, seasonal festivals, live entertainment, and the West Orange Trail. Whether you're searching for a close knit neighborhood, a home near downtown Winter Garden, or a community with exceptional amenities, this property checks every box. Don't miss this opportunity to own a beautifully upgraded home in one of Central Florida's most desirable communities.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
16185 TALIESIN ST, WINTER GARDEN, FL 34787
$649,99074 Days on yellowkey MLS ID: O6407177
REDUCED by $10,010 (1.5%) on 06/25/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2372 Built: 2020Monthly Fee: $127 Tax: $6,048 (2025)Community: HawksmoorSpa: NoSingle Family
Taxes:$6,048
Remarks: Virtually Staged. Beautifully maintained 4-bedroom, 3-bathroom two-story home located in the highly desirable Winter Garden area. Featuring over $58,000 in builder upgrades and premium features, including a premium corner lot, this home offers the perfect blend of comfort, style, and functionality. Fully paid solar panels and a fully owned whole-house water filtration system add even more value and energy efficiency. From the charming front porch and landscaped entry to the thoughtfully designed interior, every detail has been carefully selected. The open-concept first floor features tile flooring throughout the main living areas and is filled with natural light, creating a bright and airy feel. The spacious living and dining areas flow seamlessly into the gourmet kitchen, complete with stainless steel appliances, elegant upgraded cabinetry, quartz countertops, designer backsplash, and generous counter space, making it ideal for everyday living and entertaining. A first-floor bedroom and full bathroom provide the perfect setup for guests, multi-generational living, or a private home office. Upstairs, a spacious loft offers a great flex space for a media room, game room, or additional living area. The expansive primary suite serves as a relaxing retreat with a tray ceiling, large walk-in closet, and private bath featuring dual sinks. Additional bedrooms provide comfortable space and ample storage. Additional upgrades include upgraded lighting fixtures, enhanced tile and carpet flooring, 8-foot first-floor doors, added laundry room cabinetry, and an attached two-car garage with epoxy flooring, custom cabinetry, and an additional refrigerator. Residents enjoy access to fantastic community amenities including a clubhouse, resort-style pool, park, playground, and sidewalks throughout the neighborhood. Conveniently located just minutes from Hamlin Town Center, shopping, dining, entertainment, Walt Disney World, and major highways with easy access to Orlando and surrounding areas. This exceptional home combines modern upgrades, energy-efficient features, functional living spaces, and an unbeatable location. Schedule your private showing today.
4620 GLIDING WAVE ST, WINTER GARDEN, FL 34787
$539,000185 Days on yellowkey MLS ID: O6370772
REDUCED by $36,000 (6.3%) on 06/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2184 Built: 2021Monthly Fee: $136 Tax: $8,224 (2025)Community: Lakeview Preserve Ph 2Single Family
Taxes:$8,224
Elementary School: Lost Lake Elem
High School: East Ridge High
Middle School: Windy Hill Middle
Remarks: A STUNNING, ENERGY-EFFICIENT HOME LOCATED IN ONE OF WINTER GARDEN’S MOST DESIRABLE GATED COMMUNITIES. Located at the highly desirable gated community of Lakeview Preserve, this 2021-built residence offers a rare combination of modern design, comfort, and quality of life in one of Central Florida’s fastest-growing and most appreciated areas. The home features 3 bedrooms and 2 bathrooms with a fully open and integrated floor plan that creates spacious, functional living areas filled with natural light, ideal for both everyday living and entertaining. A key highlight of this property is the installed solar panel system, providing meaningful energy savings, increased efficiency, and lower monthly utility costs, adding immediate value while aligning comfort with sustainability. Lakeview Preserve is a distinctive community surrounded by nature and thoughtfully designed to deliver leisure, security, and well-being. In addition to being a gated and well-maintained neighborhood, the community offers a full range of amenities, including a swimming pool, fitness center, clubhouse for various activities and events, a splash pad, lake access with designated kayaking areas, and inviting outdoor spaces that promote a relaxed and family-friendly atmosphere. The location is strategic, with convenient access to major roadways, highly rated schools, shopping, dining, and all that Winter Garden has to provide, making this property an excellent choice for both homeowners and investors seeking long-term value, strong demand, and consistent appreciation.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Simone De Souza Nunes Silva (689-837-5076)
769 HOME GROVE DR, WINTER GARDEN, FL 34787
$524,50018 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
Elementary School: SunRidge Elementary
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)
14378 BLACK LAKE PRESERVE ST, WINTER GARDEN, FL 34787
$764,90052 Days on yellowkey MLS ID: O6414181
0 Days Off yellowkey (back on 6/9/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3167 Built: 2015Monthly Fee: $140 Tax: $6,855 (2025)Community: Black Lake PreserveSpa: NoSingle Family
Taxes:$6,855
Remarks: Under contract-accepting backup offers. Luxury At its Finest. This Beautiful Immaculate Open Concept 4 bedrooms, 4 baths residence featuring a spacious loft with a full bath. Loft on 2 nd Floor can potentially be used as a 5th bedroom. Ideal for guests retreat, home office, media lounge, media room or additional entertainment for the entire family. The Amazing Gourmet Chefs kitchen with under cabinet lighting Gas stove, double oven showcases an extra large extended island perfect for entertaining. Complemented by elegant finishes. Open concept living spaces and exceptional comfort throughout the home in its entirety. French Doors gives access to the resort style pool with 4 therapy jets, bubblers on the sun shelf, custom hand rail with multi led lights with a Wet Edge Pool Interior. Elegant Pavers. The Pool is 3 ft on the shallow end and 6 ft on the deep end and measures 15 x 31. This home is taken care with lots of Pride and Tender Loving care. This home sits on a corner Lot with lots of privacy for all entertainment and relaxation. Garage has overhead racks for extra storage. This is a very small community that is peaceful and tranquil for great evening walks. By Appointment Only. Thank You.
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Tracy Hampstead (407-803-3137)
15587 HAMLIN BLOSSOM AVE, WINTER GARDEN, FL 34787
$619,90032 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)
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