Winter Garden Real Estate

Homes for Sale in Winter Garden, FL Between $1,000,000 to $1,500,000

Welcome to your dedicated resource for Homes for Sale Between $1,000,000 to $1,500,000 in Winter Garden, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Winter Garden, FL agents, Zen Home Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $1,000,000 to $1,500,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Winter Garden, FL Homes for Sale Between $1,000,000 to $1,500,000

$1,500,000
5 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code
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.

2010 Boss Hewett Street, Winter Garden
$1,499,999
4 Beds ⋅ 3 Baths ⋅ J L Dillard Sub 3 SubDv. ⋅ 34787 Zip Code
Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.

241 N Dillard Street, Winter Garden
$1,465,000
4 Beds ⋅ 5 Baths ⋅ Winter Garden Shores 2nd Add SubDv. ⋅ 34787 Zip Code
Discover elevated living and the Winter Garden lifestyle in downtown's newest custom residence! Ideally positioned off the shores of Lake Apopka and within the beloved golf cart district, this exceptional home offers effortless access to Plant Street’s charming shops, restaurants, Farmers Market, Crooked Can Brewery, Plant Street Market, The Garden Theater & the West Orange Trail. Thoughtfully designed by locals with a deep appreciation for the character of this historic city, this exquisite 4 bedroom, 4.5-bath home blends timeless charm with refined modern finishes throughout. Majestic oaks beautifully frame the home’s craftsman-inspired architecture, while the expansive front porch invites relaxation. Inside, an open-concept design and modern kitchen are curated for both everyday comfort and endless entertaining. Inviting living spaces are complemented by elevated finishes, a wine bar, custom built-ins, a butler’s pantry & outdoor kitchen. Creatively designed to include a drop zone with a one-of-a-kind dog wash station. All bedrooms feature ensuites and custom closets. Refined outdoor living abounds on the back porch with a custom summer kitchen. Just a short golf cart ride to Pickle Ball at Veterans, Splash Pad on Plant, a swim at Farnsworth Pool or exploring nature at Newton Park. Don't miss this one-of-a-kind opportunity!

412 N Boyd Street, Winter Garden
$1,400,000
4 Beds ⋅ 4 Baths ⋅ Hull Island At Oakland SubDv. ⋅ 34787 Zip Code
Welcome to this extraordinary custom lakefront estate offering breathtaking views of Lake Apopka and the ultimate Florida waterfront lifestyle. Designed with luxury and functionality in mind, this one-of-a-kind home showcases premium upgrades, exceptional craftsmanship, and direct lake access. The heart of the home is a chef-inspired kitchen featuring a natural gas cooktop, double ovens, expansive center island, abundant counter space, separate breakfast dinette, and a custom walk-in pantry with floor-to-ceiling shelving. The kitchen opens seamlessly to the spacious family room with soaring 12-foot ceilings and triple sliding glass doors that frame spectacular lake views and fill the home with natural light. Step outside to your private waterfront oasis where a covered, screened lanai overlooks professionally landscaped grounds and unforgettable sunsets. The impressive 20' x 60' brick paver patio leads to a private dock with an electric covered boat lift, providing direct access to Lake Apopka. Enjoy fishing from your dock, boating the scenic Harris Chain of Lakes via the Apopka-Beauclair Canal, or spending the day exploring the waterfront restaurants, shops, and attractions of historic downtown Mount Dora and Tavares. The thoughtfully designed floor plan includes a formal dining room with soaring ceilings and a private office with double doors, ideal for working from home. The luxurious primary suite is a true retreat with panoramic lake views, spa-inspired bath featuring a frameless floor-to-ceiling tiled double shower with dual shower heads and built-in bench, soaking tub, dual vanities, and custom walk-in closets. A hidden Murphy door provides private access to two secondary bedrooms and a full bath, creating the perfect guest or family wing. The oversized fourth bedroom offers an ensuite bath and walk-in closet, ideal for guests or multigenerational living. Additional premium features include a 24kW natural gas whole-house generator, electric vehicle charging station, water softener, security system, surround sound, insulated garage doors and ceiling, garage utility sink, overhead storage, and a spacious laundry room with built-in cabinetry, extensive counter space, and utility sink. The oversized three-car garage and expansive six-car brick paver driveway provide ample parking and storage. Located in the sought-after gated community of Hull Island, residents enjoy resort-style amenities including a community pool, gazebo, playground, bark park, and exclusive private access to the 150-acre Oakland Nature Preserve with miles of scenic trails. Nestled in the charming Town of Oakland, this exceptional home is just minutes from Winter Garden Village, historic Downtown Winter Garden, the award-winning Winter Garden Farmers Market, the West Orange Trail, Downtown Clermont, shopping, dining, major hospitals, Orlando's world-famous attractions, Orlando International Airport, and major highways. Florida's beautiful east and west coast beaches are approximately one hour away.

1112 Hull Island Drive, Oakland
$1,399,000
6 Beds ⋅ 6 Baths ⋅ Waterside/Johns Lake Ph 1 SubDv. ⋅ 34787 Zip Code
An Irreplaceable Gated Estate: Unmatched Scale, Double-Lot Privacy, & Private Oasis Behind the gates of the highly coveted Waterside community, 16614 Harbor Sail Way breaks the mold of standard luxury builds. This is not a high-density, cookie-cutter residence; it is an established, substantial family estate defined by an extraordinary sense of space, meticulous craftsmanship, and structural authority. Positioned beautifully on an expansive, premium lot that nearly doubles the community average, this rare property offers a refined lifestyle designed for those who value space to breathe, long-term permanence, and effortless entertaining. While typical Mansfield floor plans in the neighborhood occupy a standard lot, this home’s visionary owners secured the adjacent parcel, resulting in a commanding 14,973-square-foot footprint. This unique layout introduces a majestic private turning circle with dedicated parking for an additional six vehicles (bringing total driveway capacity to ten)—ideal for hosting executive gatherings or multi-generational families. Beyond the striking courtyard entry, the residence spans an impressive 4,882 square feet of meticulously maintained living space, delivering structural scale that effortlessly handles the demands of modern family life. The heart of the home centers on a dramatic great room bathed in natural light, seamlessly connecting to a gourmet kitchen equipped with premium finishes and gas cooking. Every corner of the main level emphasizes functional luxury, including a private home office, formal dining room, a secluded guest suite, and a magnificent primary sanctuary. Ascending to the second level reveals a sprawling, open flex room suspended over the main living area that opens to a fully enclosed, private balcony, creating an incredible architectural anchor. This level features four additional large bedrooms and media room, offering families the chance to spend time together, or unwind in complete peace. For ultimate daily convenience, a built-in central vacuum system services the ground floor of the home. While neighboring homes may provide "room for a future pool," this estate delivers the ultimate outdoor lifestyle immediately. The west-facing backyard is a private, sun-drenched sanctuary featuring a spectacular custom salt-water pool and integrated spa. Surrounded by extended paver decking and lush, manicured grassed areas made possible by the expanded double-lot footprint, this outdoor space offers complete privacy with no direct rear neighbors—perfect for enjoying vibrant Central Florida sunsets. Living in Waterside means enjoying a resort-style lifestyle with access to a premier clubhouse, fitness center and community pool. You are uniquely positioned just minutes from Horizon West’s top-rated schools (Hamlin Elementary/Middle), West Orange (High), the charm of downtown Winter Garden, major executive corridors (SR-429, Turnpike), and premier dining and shopping. This is more than a home; it is a strategic asset of scarcity, privacy, and generational quality. Schedule your private tour to experience it firsthand.

16614 Harbor Sail Way, Winter Garden
$1,395,000
4 Beds ⋅ 3 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Virtually Staged. One or more photo(s) was virtually staged. Newly remodeled in 2026 and presented in like-new condition, this exceptional single-story lakefront home blends an elevated luxe coastal feel with relaxed Florida waterfront living. Set on a rare oversized lot along skiable Huckleberry Lake, the property offers exceptional privacy and space, with approximately 40 feet of separation between neighboring homes. The light and inviting interior features (4) four bedrooms, (3) three full baths, and a spacious open-concept floor plan. The beautifully updated kitchen showcases quartz countertops and flows seamlessly into the main living and entertaining areas. A generously sized open flex room offers additional versatility as a formal dining room, home office, formal living room, or sitting room and can easily be enclosed for additional privacy. Step outside to a large fenced backyard with a private pool and spa, all overlooking Huckleberry Lake. Enjoy direct lake frontage and water access, with the opportunity for a private dock, subject to applicable HOA approval and permitting. The (3) three-car garage includes a Tesla EV charger, and the expansive driveway accommodates up to (6) six additional vehicles. Lakeview Pointe offers a community dock on Huckleberry Lake, resort-style pool with splash area, and fully equipped fitness center. The HOA also takes care of the home's exterior lawn maintenance, giving you more time to enjoy the lake, pool, and Florida lifestyle. Ideally located in Winter Garden's Horizon West area, with easy access to SR 429 and minutes from shopping, dining, entertainment, and everyday conveniences. The property is currently zoned for A-rated Summerlake Elementary, Hamlin Middle School, and Horizon High School. Nearby early-learning options include Primrose School of Horizon West, The Learning Experience - Horizon West, and KLA Schools of Horizon West. Walt Disney World is approximately 20 minutes away. Buyers should independently verify current school assignments and grades. A rare opportunity to own a beautifully remodeled single-story pool home on skiable Huckleberry Lake, combining privacy, flexible living spaces, an oversized lakefront lot, and true Florida waterfront living.

14048 Larkspur Lake Drive, Winter Garden
$1,389,000
5 Beds ⋅ 5 Baths ⋅ Avalon Cove SubDv. ⋅ 34787 Zip Code
Nestled within one of Central Florida's most exclusive neighborhoods this stunning home offers the perfect blend of luxury, comfort, and effortless entertaining. Located on a quiet cul-de-sac street boasting 5 bedrooms, 4.5 baths, a large loft and open floor plan this home is designed for everyday living and seamless hosting! Step outside to your private resort style salt water pool and enjoy nightly views of the Disney fireworks lighting up the sky! The upgraded "picture frame" pool screen design offers an uninterrupted view of the serene pond and the diverse wildlife that visits it! On the main level you will find the PRIMARY SUITE COMPLETE WITH A LUXURIOUS SPA LIKE BATH AND HUGE walk-in closet, a guest bedroom with its own full bath, the glass enclosed wine room and a convenient half bath for guests. The GOURMET KITCHEN flows to the expansive great room where 4 large sliders can open to the covered patio for the "outside inside" living!! Upstairs, in addition to the large loft are 2 bedrooms that share a full bath and another private en-suite bedroom. Recent upgrades include beams on the main level ceiling, beautiful built-in wall unit in the loft, outdoor kitchen and outdoor lighting. Located just minutes from Walt Disney World, premier shopping, dining, and everyday conveniences, and approximately 30 minutes to Orlando International Airport, this beautiful home is perfect for that unbeatable central Florida lifestyle!

9103 Morgana Court, Winter Garden
$1,350,000
6 Beds ⋅ 5 Baths ⋅ Waterside/Johns Lk-Ph 1 SubDv. ⋅ 34787 Zip Code
With a whisper of Tuscan charm, Waterside on Johns Lake is a private GATED community featuring this impressive 6 BEDROOM (w/additional 7th room) 4.5 BATHROOM estate. As you pull up you will be welcomed by curb appeal, thoughtful landscaping, entry courtyard, 2 CAR GARAGE, and separate BOAT/TOY GARAGE. Inside the ceilings soar: with lots of NATURAL LIGHT, specialty molding, WOOD BEAMS, iron railings, built-ins, and a balance of both open concept & compartmentalized spaces. Downstairs you will find the 2-story ceiling Living Room, both FORMAL & CASUAL DINING space, Laundry Quarters, Butlers Pantry, Nanny's Workspace, Office, IN-LAW SUITE, and Primary Bedroom with SPA STYLE ENSUITE featuring a massive RAINSHOWER, GARDEN TUB, DOUBLE WALK IN CLOSETS, and separate vanities. And let's take a moment to discuss the CHEF'S KITCHEN that you will no longer have to envy, because as the new owner of this home you can whip up family meals or dinner party delights using your KITCHENAID 5 BURNER RANGE, convenient POT-FILLER set into glass tile backsplash, INDUSTRIAL DOUBLE REFFIGERATOR, oversized kitchen island, coffee bar, desert bar, KITCHENAID DOUBLE WALL OVEN, built-in Convection Oven/Microwave, and walk-in Pantry. Up the stairway lined with ironwork and over the landing, you reach the SUPERSIZED LOFT before leading to the 4 MORE BEDROOMS and 2 bathrooms. Currently one of the bedrooms is being used as an in-home gym and another as a craft room. The other 2 are joined by a JACKNJILL BATHROOM, perfect for kiddos or SECONDARY IN-LAW SUITE/Living space combo. With so much space, this home will suit most any lifestyle needs. For outdoor living you will find a LARGE YARD off a COVERED LANAI with NO REAR NEIGHBORS and privacy bushes. Space for a future pool and outdoor entertaining customized just how you like it. For existing outdoor recreation, Waterside on Johns Lake offers a clubhouse, fitness center, community pool, trails, playgrounds, and a community dock perfect for watching cotton candy sunsets. Zoned for A rated public schools & nearby private school options. Nearby there is an abundance of restaurants, shopping, convenience, and the sought after Downtown Winter Garden lifestyle. Come see this spacious estate that you will want to call home soon.

16730 Rusty Anchor Road, Winter Garden
$1,349,000
4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 2 & 5 SubDv. ⋅ 34787 Zip Code
Ideally located in the highly sought-after Hamlin area of Winter Garden, this beautifully maintained pool home offers the perfect combination of comfort, convenience, and Florida living with beautiful lake Hancock views. Enjoy easy access to shopping, dining, entertainment, major roadways, outdoor recreation, and the many attractions and amenities throughout Winter Garden and Horizon West. Designed for effortless everyday living and entertaining, the residence features bright, spacious interiors that flow seamlessly into the outdoor living area. The private saltwater pool can be heated using either solar energy or gas, providing flexibility and year-round enjoyment. Fully paid-off solar panels offer an exceptional advantage, with no solar lease or financing obligation for the new owner. Additional improvements include one brand-new air-conditioning system, a second A/C system replaced less than three years ago, and a whole-home water softener and filtration system with reverse osmosis for drinking water. Fresh landscaping enhances the home’s curb appeal and creates a welcoming first impression. With its energy-efficient features, valuable recent upgrades, resort-style outdoor space, and desirable location, this move-in-ready property presents an exceptional opportunity to enjoy the best of the Winter Garden lifestyle.

15240 Shonan Gold Drive, Winter Garden
$1,349,000
5 Beds ⋅ 5 Baths ⋅ Hawksmoor-Phase 1 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully upgraded home in Winter Garden, where thoughtful design, exceptional upgrades, and resort-style outdoor living come together. From the moment you enter, you’ll appreciate the attention to detail, quality finishes, and extensive improvements throughout. The heart of the home is the fully upgraded gourmet kitchen, featuring upgraded cabinetry, an oversized island, upgraded backsplash, upgraded pendant lighting, and a custom pantry. The movie room takes entertaining to the next level with a built-in wet bar featuring upgraded cabinetry, creating the perfect space for movie nights, game days, and gatherings. The home features CoreTec luxury vinyl plank flooring throughout and on the stairs, complemented by upgraded stair handrails and wrought-iron banisters. Additional comfort and convenience upgrades include an Ecowater water softener, Grundfos circulating pump, purified cold-water filtration at the kitchen sink, and Nu-Calgon UV light sanitizers for both air-handler coils. Step outside to your own private oasis featuring an impressive in-ground pool and outdoor living package by Kura Pools, complete with an 8' x 8' spa, heater, chiller, and screened enclosure. The backyard has been enhanced with newly planted hibiscus and Christmas palms, while an AI-powered Govee outdoor lighting system lets you illuminate and customize the outdoor space for any season or occasion. Additional upgrades include a dedicated 600V electrical panel for pool equipment, an included Tesla EV charger, garage door openers, a laundry room tub, upgraded pedestal in the first-floor powder room, plantation-style shutters on the main floor family room and primary suite, and manual roller shades in select areas. Security and convenience are also top priorities with an Amazon Ring security system featuring indoor and outdoor cameras throughout the home. This exceptional property combines luxury, functionality, entertainment, and outdoor living in one of Winter Garden’s desirable communities. With an extensive list of upgrades already completed, this home offers an opportunity to enjoy a truly turnkey lifestyle with little left to do but move in and enjoy.

17077 Wingspread Loop, Winter Garden
$1,349,000
7 Beds ⋅ 4 Baths ⋅ Mcallister Lndg SubDv. ⋅ 34787 Zip Code
Welcome to an extraordinary Winter Garden retreat where luxury, flexibility, and resort-style living come together in one remarkable residence. Situated on a premium corner lot, this expansive 7-bedroom, 4-bath home offers over-the-top living spaces designed for entertaining, multi-generational living, and creating unforgettable memories. Step inside to soaring ceilings, abundant natural light, and an open-concept floor plan that effortlessly blends elegance with everyday comfort. The chef-inspired kitchen serves as the heart of the home, featuring an oversized island, breakfast bar, abundant cabinetry, and seamless flow into the spacious family room and café dining area. The thoughtfully designed layout includes both the owner's suite and a guest bedroom on the main level, providing ideal accommodations for extended family or visitors. Upstairs, a sprawling game room, dedicated home theater, and additional bedrooms create the ultimate entertainment hub for family and guests alike. Outside, your private backyard oasis awaits. Relax by the sparkling in-ground pool, entertain under the covered lanai, or host gatherings in the fully equipped summer kitchen. The fully fenced yard provides privacy while maximizing enjoyment of Florida's year-round sunshine. Perfectly positioned just minutes from Historic Downtown Winter Garden, Orlando's world-famous attractions, premier dining, shopping, and entertainment, this exceptional home offers the lifestyle today's buyers are seeking—space to gather, room to grow, and amenities that make every day feel like a vacation.

1698 Juniper Hammock Street, Winter Garden
$1,300,000
5 Beds ⋅ 4 Baths ⋅ Lakeview Reserve 46/149 SubDv. ⋅ 34787 Zip Code
PRICE IMPROVEMENT! Refined Waterfront Living in Winter Garden’s Coveted Golf Cart District! Set within one of Downtown Winter Garden’s most desirable gated enclaves, this exceptional waterfront residence offers a rare blend of sophistication, privacy, and effortless Florida living—perfectly positioned in the highly sought-after golf cart district. Designed to maximize light and livability, the interiors are bright and inviting. Recent enhancements include new exterior paint (2026), a tankless water heater (2026), and a added ensuite bathroom (2026) making two primary suites on the second floor. Generous storage is thoughtfully integrated with expansive closet space, while a whole-home water softener and purification system, including an under-sink filter, ensures elevated everyday comfort. At the heart of the home, the gourmet kitchen is both functional and beautifully appointed, featuring dual sinks, a dedicated prep island, and upgraded soft-close cabinetry. The oversized three-car garage provides ample room for vehicles, storage, or recreational needs. Outdoors, the lifestyle truly unfolds. A recently resurfaced covered boat dock—complete with lift, lighting, fan, and sink—offers direct access to one of Florida’s largest spring-fed lakes, part of the Harris Chain and extending to the St. Johns River and Atlantic Ocean. The expansive grounds are enriched by mature, fruit-bearing trees including mango, avocado, star fruit, and citrus, creating a lush, private retreat. Surrounded by natural beauty, the property attracts an impressive array of wildlife. Unforgettable sunrises and sunsets can be enjoyed from multiple vantage points, including the living spaces, patio, dock, and three north-facing bedrooms with water views. This is a home that seamlessly balances elegance and ease—offering a rare opportunity to experience serene waterfront living in one of Winter Garden’s most iconic settings.

243 Zachary Wade Street, Winter Garden
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