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
$1,450,000
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 4 SubDv. ⋅ 34787 Zip Code
Captivating water and golf course views set the stage for a chic and distinguished single-story residence in Lakeshore Preserve. This better-than-new home boasts a great room floorplan with split bedroom layout, sliding pocket doors, an exceptional screened pool patio area with hybrid saltwater and chlorine pool with sun shelf and water features, plus tranquil lake beyond. Elegant white on white kitchen with stainless appliances, gas cooktop with hood, waterfall quartz island, and an abundance of cabinetry including a few lighted glass showplace cubicles with doors. Graced with wood-look tile flooring and transitional neutral grays and whites throughout this home offers a clean-look elegant canvas. Landscape lighting creates an elegant ambiance at night. Enjoy a nearly carefree lifestyle with exterior yard maintenance included in your monthly HOA fee. 1-gig high-speed internet is also included. Community features resort-style amenities including a waterfront community pool, cabanas, walking trails, and access to Lake Panther via a community ramp for canoes, kayaks, and other non-motorized watercraft. There’s also a community clubhouse with fitness center and activity spaces. Top-rated Panther Lake Elementary is located within the neighborhood and Horizon High School is across the street. Orange County National Golf Center is just minutes away. Enjoy nightly fireworks from the Magic Kingdom at Walt Disney World and easy access to the SR-429 to connect to downtown Orlando. Welcome to Horizon West’s best address for lifestyle, luxury, and livability.

15619 Giant Foxtail Court, Winter Garden
$1,399,999
4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 2 & 5 SubDv. ⋅ 34787 Zip Code
Welcome to this spacious 4-bedroom, 3.5-bath pool home offering 4,000 square feet in the highly sought-after Overlook at Hamlin community in Horizon West. Showcasing Lake Hancock views throughout the home and Disney fireworks in the distance, this property combines generous living space, impressive architecture, and an unbeatable location in one of Winter Garden's most desirable communities. From the moment you arrive, you'll appreciate the paver driveway, fresh landscaping, side-entry two-car garage, and curb appeal. Step inside to find a formal dining room and home office. Continue into the heart of the home where soaring ceilings and a dramatic two-story design create a bright, open atmosphere. The expansive family room showcases picturesque pool and lake views, while the open-concept layout flows seamlessly into the kitchen and casual dining area, making it ideal for everyday living and entertaining. The kitchen features granite countertops, light cabinetry, two oversized islands, abundant prep space, a walk-in pantry, and a butler's pantry ideal for a coffee station. Stainless steel appliances include a Monogram built-in oven and microwave, Monogram dishwasher, and a Monogram five-burner natural gas cooktop. The first-floor primary suite offers a private retreat with pool views, two walk-in closets, and an ensuite bath complete with dual vanities, a garden tub, and a large glass-enclosed shower. An impressive staircase with decorative iron balusters leads to the second floor, where an open overlook adds to the home's spacious feel. Upstairs you'll find three additional bedrooms, all with walk-in closets, two full bathrooms, a large loft perfect for a media room or secondary living area, and a versatile flex room that can serve as a home gym, study, playroom, hobby room, or potential fifth bedroom. Combined with the dedicated first-floor office, these flexible spaces provide exceptional versatility for remote work, multi-generational living, or growing households. Two upstairs bedrooms enjoy Lake Hancock views. Step outside to the expansive screened lanai with space for outdoor dining, relaxing, and entertaining. The saltwater pool and Lake Hancock views create an exceptional outdoor setting. Residents of Overlook at Hamlin enjoy access to a clubhouse, fitness center, resort-style pool, playgrounds, golf cart-friendly streets, and community lake access. Located just minutes from Hamlin Town Center, you'll enjoy convenient access to shopping, dining, waterfront restaurants, grocery stores, PopStroke, Cinépolis Luxury Cinemas, Urban Air, and everyday conveniences. A rare opportunity to own a spacious pool home with Lake Hancock views in the heart of Horizon West and Winter Garden's thriving Hamlin area.

15264 Shonan Gold Drive, Winter Garden
$1,399,900
5 Beds ⋅ 5 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code
Experience refined elegance in this beautifully maintained residence located in one of Winter Garden’s most desirable communities. Designed for modern living, the home offers bright open spaces, a stylish kitchen, and inviting bedrooms that blend comfort with sophistication. Step outside to a private, resort-style backyard with over $200,000 invested, creating an exceptional outdoor oasis perfect for entertaining or unwinding in total privacy. Ideally positioned near top-rated schools, upscale dining, shopping, major highways, Downtown Winter Garden, Disney attractions, and Orlando—this home delivers luxury, location, and lifestyle at its finest.

16548 Raven Rock Place, Winter Garden
$1,399,900
7 Beds ⋅ 5 Baths ⋅ Twinwaters Homeowners' Association, Inc. SubDv. ⋅ 34787 Zip Code
Discover Unmatched Elegance in the Coveted Twinwaters Subdivision! Welcome to your dream home, a breathtaking Winter Garden pool residence built in 2016, offering the perfect fusion of sophistication, luxury, and prime convenience. This property isn’t just a house – it’s your personal sanctuary. Grand Entrance That Stuns: Be greeted by an impressive 14-foot foyer adorned with a dazzling crystal chandelier. A beautifully crafted wooden staircase with iron balusters sets the tone for the home’s elevated style. From the moment you step inside, the open-concept layout invites you to explore spaces designed for both comfort and entertainment. Exquisite Interiors: Every detail exudes elegance. Stunning wood plank accent walls, gleaming 30-inch marble tiles, intricate tray ceilings, and granite countertops throughout create a refined yet warm atmosphere. Whether hosting friends or enjoying quiet family moments, this home is the ultimate setting. First Floor Features: Luxurious Master Suite: Tray ceiling, serene ambiance, and ample space for relaxation. Versatile Guest Suite: Ideal for guests or teens, offering privacy and comfort. Functional Spaces: A large and cozy family room, private office, formal living and dining areas, plus a service pantry with wine storage and a separate laundry room. Gourmet Kitchen: A chef’s paradise with a granite island and seating, deep basin sink, custom 50” solid wood cabinets with glass accents, glass tile backsplash, built-in oven and microwave, and a walk-in pantry. Second Floor Highlights: Expansive Upper Lounge: Large windows fill the space with natural light, making it perfect for relaxation. Bonus Room: Create your dream space—whether a music studio, movie theater, gym, or private office. Second Master Suite: Spacious and serene, with luxurious finishes. Four additional bedrooms, each offering comfort and versatility. Outdoor Oasis: Your backyard is a private paradise! A covered lanai overlooks lush landscaping, a pristine vinyl fence, and a sparkling pool. It’s the perfect retreat for relaxation or entertainment. Modern Conveniences: Solar-powered electricity for energy efficiency Whole-home water purification system Tankless water heater Crown molding throughout Tray ceilings and architectural enhancements that elevate the aesthetic Over 25k in Curtain Work Prime Location & Community Perks: Located in the sought-after Twinwaters community, enjoy access to a community pool and recreation area. Nearby, explore Winter Garden Village, Historic Downtown Winter Garden, Walt Disney World, and top-rated schools. Central Florida’s major highways, shopping, dining, and entertainment are all just minutes away. This home is truly one-of-a-kind.

16669 Varone Cove Court, Winter Garden
$1,399,000
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
$1,390,000
5 Beds ⋅ 4 Baths ⋅ Hillcrest SubDv. ⋅ 34787 Zip Code
A truly rare find in beautiful Downtown Winter Garden's highly coveted Golf Cart District, with NO HOA this exceptional 5-bedroom, 3.5-bath residence offers a once-in-a-lifetime opportunity to own a home where luxury, character, and location come together beautifully. Thoughtfully renovated from top to bottom, this one-of-a kind property combines timeless craftsmanship with modern elegance and resort-style outdoor living. Every inch of this home has been meticulously updated with high-end finished , including a stunning chef's kitchen featuring quartz countertops, a large center island, custom cabinetry with panel-ready appliances, double ovens, a wine refrigerator, a walk-in pantry, and gorgeous copper accents including a double farmhouse sink, matching range hood, pot filler, and faucet. The inviting living spaces showcase custom craftsman trim, elegant wainscoting, oversized baseboards, shiplap ceilings, a beautiful fireplace with a custom stone entertainment wall, a built-in library, designer lighting, and travertine flooring in the kitchen and bathrooms. Step outside into your own private backyard oasis where you'll find a heated, newly resurfaced pool and above-ground spa, a spacious paver pool deck, screened lanai, pergola with a fire pit, raised garden beds, and professionally designed landscaping surrounded by mature hedges, picket fencing, majestic oak trees, crepe myrtles, gardenias, and rose bushes, creating exceptional beauty and privacy. The expansive property also features a detached workshop, and an extra-long spacious driveway with abundant parking for all your toys!!This home offers peace of mind with countless recent upgrades, including a NEW ROOF with metal porch roofing, two NEW HVAC systems a NEW HOTWATER HEATER, NEW POOL PUMP, Ecobee smart thermostats, digital entry, a new pool bath, Centricon termite protection, and in-wall pest control tubing. Perfectly located just a short golf cart ride from Winter Garden's award-winning restaurants, charming boutiques, the famous Farmers Market, and the West Orange Trail, this is more than just a home—it's a lifestyle. Homes of this caliber, with this level of craftsmanship, outdoor amenities, and an unbeatable Downtown Winter Garden location, and NO HOA rarely come to market. Schedule your private showing today to experience everything this extraordinary property offers. If you are lucky enought to purchase this home you are not just getting a home, you're getting a rare opportunity in one of Central Florida's most desirable communities.

1324 Vic Kay Court, Winter Garden
$1,375,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 1a SubDv. ⋅ 34787 Zip Code
Now offered at $1,375,000 following a $124,000 price adjustment. This luxury residence presents an exceptional opportunity to own a beautifully designed home at its newly adjusted price. Rare opportunity to own an exceptional lakefront residence with a private dock and breathtaking panoramic water views in one of Winter Garden's premier resort-style communities. Offering approximately 4,663 square feet of living space, this impressive home features 4 bedrooms, 4 bathrooms, and a 3-car garage on a spectacular direct lakefront homesite. Designed to maximize the stunning waterfront setting, the home showcases soaring ceilings, elegant architectural details, expansive living spaces, and abundant natural light throughout. The gourmet kitchen features an oversized island, double ovens, walk-in pantry, and seamless flow into the main living areas, all positioned to capture beautiful lake views. The luxurious primary suite serves as a private retreat with direct access to a covered second-floor balcony overlooking the water. Additional indoor and outdoor living spaces, including a covered lanai, provide the perfect setting for entertaining or simply enjoying Florida's year-round lifestyle. Residents enjoy access to resort-style amenities including pools, clubhouse, fitness center, walking trails, and playgrounds. Conveniently located near shopping, dining, entertainment, and major roadways, this remarkable waterfront property offers luxury, privacy, and an unparalleled lakefront lifestyle.

8530 Bayview Crossing Drive, Winter Garden
$1,374,990
5 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2c-2 & 2c-3 SubDv. ⋅ 34787 Zip Code
Perfectly positioned on a PREMIER WATERFRONT LOT just under half an acre, this stunning 3,910-square-foot residence delivers luxury living at every turn. Tucked away at the end of a tranquil cul-de-sac and situated on one of the few homesites in the neighborhood with no neighbors in front or behind, the property offers an exceptional sense of privacy with beautiful views of Lake Noah. A grand foyer with a dramatic wrought iron staircase sets the tone for the sophisticated interiors, where CROWN MOLDING and WAINSCOTING elevate the home throughout. The GOURMET KITCHEN is both stylish and functional, featuring a center island, glass-front cabinetry, under-cabinet lighting, designer backsplash, stainless steel appliances, and a sleek flat cooktop. A butler’s pantry and formal dining room create the perfect setup for effortless entertaining. The luxurious primary suite features a CUSTOM CALIFORNIA CLOSET SYSTEM and a spa-inspired bath with dual vanities and an oversized walk-in shower complete with double shower heads, including a RAIN SHOWER. Spacious secondary bedrooms all offer walk-in closets, with two connected by a JACK-AND-JILL BATHROOM, while the oversized upstairs loft provides flexible living space ideal for a media room, game room, or lounge. Designed for both comfort and convenience, the home also includes a 3-car tandem garage with EPOXY FLOORINGS and HANGING STORAGE RACKS, a WHOLE-HOUSE GENERAC GENERATOR, a WHOLE-HOUSE HALO WATER FILTRATION SSTEM, NEW 80-GALLON WATER HEATER, security system with cameras throughout. The backyard is a true private retreat featuring a gas-heated saltwater pool and spa with water features, SUMMER KITCHEN, FIRE PIT, screened enclosure, OUTDOOR SONOS SURROUND SOUND SPEAKER SYSTEM, upgraded LIGHTING PACKAGE, and lush professional landscaping. Beyond the screen enclosure, the fully fenced yard offers additional green space rarely found in waterfront homes. One of the property’s most unique features is the ABILITY TO BUUILD A PRIVATE DOCK on Lake Noah, offering an incredible opportunity to embrace true waterfront living in one of Winter Garden’s premier communities. Conveniently located near top-rated schools, shopping, dining, Disney, and major roadways, this home effortlessly combines luxury, lifestyle, and location into one exceptional offering. Opportunities like this do not come along often.

9827 Beach Port Drive, Winter Garden
$1,350,000
5 Beds ⋅ 4 Baths ⋅ Valley View SubDv. ⋅ 34787 Zip Code
Virtually Staged. Rare opportunity in Winter Garden's coveted Lake Avalon: a fully fenced and gated 5-acre mini-ranch in the Valley View enclave, where genuine Lake Avalon water and conservation views meet true rural freedom — bring your horses, livestock, or recreational vehicles — just minutes from Hamlin Town Center, Walt Disney World, and SR-429. Spanning nearly 3,800 SF, this thoughtfully expanded 5BR/4BA estate includes a substantial permitted addition that created an ideal wing for multi-generational living or large-scale entertaining. At its center is a redesigned custom kitchen with imported Italian cabinetry, waterfall-edge countertops, premium Thermador appliances, and a built-in Dacor smart refrigerator. A separate enclosed prep kitchen with additional appliances and laundry hookups adds rare day-to-day functionality. The layout offers dual primary suites, formal and casual living spaces, oversized tile flooring, modern LED lighting, and remodeled baths — openness and privacy as you need them. Major systems deliver long-term peace of mind: a NEW ROOF (2022) NEW HVAC (2022), an 80-gallon commercial water heater (2022), a whole-home water softener, and a 24KW whole-house standby generator with transfer switch for full backup power. Zoning flexibility, sunset and lake views, and no cookie-cutter HOA rules — one of the last true large-lot enclaves this close to Winter Garden's growth corridor. Schedule your private tour today.

9508 Quiet Lane, Winter Garden
$1,349,000
5 Beds ⋅ 4 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Stunning family home with an option to purchase the fully renovated 3 bed, 2 bath home next door - perfect for inlaws home, investment property, or just extra family space (call agent for details)!! Experience the best of Historic Winter Garden living in this brand-new Craftsman-style home, ideally located just steps from downtown dining, shopping, entertainment, and the renowned West Orange Trail. Originally a charming 1950s bungalow, the 576 sq. ft. home has been completely renovated and thoughtfully expanded into a stunning 2,800 sq. ft. residence offering 5 bedrooms, 4 bathrooms, and exceptional modern upgrades throughout. Relax on the inviting front porch and enjoy the charm and atmosphere of this idyllic golf cart community. Inside, a bright and spacious open floor plan welcomes you with designer finishes, 10-foot ceilings, luxury waterproof vinyl plank flooring, plantation shutters, 8-foot doors, and elegant architectural details throughout. The heart of the home is the spectacular chef’s kitchen featuring premium LG stainless steel appliances, built-in oven and microwave, induction cooktop, wine fridge, oversized island with seating and storage, 42” refrigerator, and an enormous walk-in pantry complete with an additional retro-style refrigerator. The adjoining family room showcases a custom fireplace with built-in storage and two sets of French doors opening to a large covered lanai with summer kitchen, overlooking the beautifully landscaped and fully fenced backyard with additional deck space for entertaining and relaxing. The luxurious primary suite offers custom walk-in closets, a spa-inspired en-suite bath, and private French doors leading to a secluded patio and deck area. A separate lower-level wing includes two additional bedrooms, a full bath, and utility room, creating endless possibilities for an in-law suite, home office, theater room, or private guest retreat. Upstairs, you’ll find two spacious bedrooms, including one with en-suite bath, an additional full bath, linen storage, and generous extra storage space. Additional highlights include a covered carport with EV charging outlet, oversized driveway with parking for at least 6 cars, 2-zone A/C system, gutters with leaf guards, upgraded lighting, charming picket fencing, lush landscaping, and a 10x8 storage/workshop. Live the coveted Winter Garden lifestyle with golf cart access to charming boutiques, restaurants, breweries, parks, the weekly farmers market, Lake Apopka, splash pad, and more. This exceptional home perfectly combines historic charm with luxurious modern living in one of Central Florida’s most sought-after communities. Don’t miss this rare opportunity!

217 W Bay Street, Winter Garden
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