Explore Winter Garden, FL Homes for Sale Between $1,250,000 to $1,500,000

Homes for Sale in Winter Garden, FL Between $1,250,000 to $1,500,000

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Welcome to your dedicated resource for Homes for Sale Between $1,250,000 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 a local Winter Garden, FL agent, The Nest 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 $1,250,000 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 $1,250,000 to $1,500,000

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

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

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

5 Beds ⋅ 5 Baths ⋅ Sanctuary/Twin Waters SubDv. ⋅ 34787 Zip Code

Luxurious 5-bedroom 5-bathroom home with TWO MASTER SUITES. The primary suite is on the second floor. The second suite is located on the first floor. 8 x 48 Ceramic tile with warm wood-look throughout the entire home. Massive Kitchen Island. Quartz Waterfall for Kitchen Island. Farmhouse Undermount Cast Iron Kitchen Sink. Butler’s Pantry area and Large Walk-in pantry between the Kitchen and Dining Room. Solid wood 42-inch cabinets with undermount lighting and soft-close doors and drawers. Pot filler above the gas cooktop. Stainless steel appliances include a built-in oven and microwave. Custom-built-in wine storage, wine and beer refrigerators under the stairs. Outside Covered Patio on first floor and covered second floor patio overlooking the enormous pool and spa. Surround sound setup with Ceiling Speakers both on the interior of the home. Outdoor kitchen with sink, refrigerator, cooktop, gas, and charcoal grills. Natural Gas Community with underground natural gas for outdoor grill, kitchen cooktop, pool and spa heater. Community Pool with restrooms, Recreation Area with kids' playground, dock, and Lake Access to Lake Avalon.

16689 Toccoa Row, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Hawksmoor Ph 4 SubDv. ⋅ 34787 Zip Code

Come take a look at this beautiful modern elevation and spacious home. Hawksmoor community offers a luxury lifestyle nestled in Winter Garden's popular Horizon West area. This spacious home is located on the corner lot with fenced in backyard. This home offers plenty of comfort and upgraded features inside and outside. Some features in this home are the well maintained wooden floors, baseboards, backsplash features and stone countertops across the home with plenty more! The kitchen is upgraded with stainless steel kitchen aid and newer appliances alongside having a walk in pantry with cabinets all around! The open layout living room with high ceilings creates the opportunity to bring in natural light and energy to this home. The master bedroom is located on the first floor and it offers a spacious walk in closet inside the master bathroom. A powder restroom is also located on the first floor of home, game room and the laundry room with sink , washer & dryer appliances to remain. Upstairs offers four spacious bedrooms, a large family room area as well alongside Jack and Jill bathroom in between bedrooms. Finally, outside the patio is a smart screened patio where a stunning summer kitchen sits for hosting cookouts. Beautiful amenities complement the luxurious lifestyle this community boasts and include a stunning, resort-style pool, splash pad, clubhouse with outdoor summer kitchen & grill, yoga lawn, shaded playground, and network of walking trails. The community offers a gym with weight machines, dumbbells, and a few options for cardio. The clubhouse can also be rented for special events. Commuters convenience approximately minutes from the SR429. Hawksmoor convenient location within Winter Garden means dining, shopping and entertainment are never far away. Refrigerator in garage and water softener do not convey to property, all appliances are included. Call to schedule your private showing.

16894 Wingspread Loop, Winter Garden

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

Avalon Hills Sub SubDv. ⋅ 34787 Zip Code

Discover 5.1 beautiful acres in Avalon Hills, an exclusive community featuring just 16 premium luxury home 5 acre lots. No need to move almost an hour away just to find some land and more privacy when this gem is minutes to Windermere and everywhere you want to be. This vacant land represents the essence of premium real estate, nestled at the end of a one-way street ending in a serene cul-de-sac bordered by State conservation land that will never be developed. Imagine crafting your dream home on the premier lot, perched on a gentle hill overlooking the entire neighborhood. The elevation advantage allows for breathtaking sunset views that you can relish right from your front door. Numerous mature oak trees throughout the property offer splendid options for integrating them into your home's design. While maintaining the tranquil country atmosphere, you'll still enjoy all the advantages of a Winter Garden zip code while paying Lake County taxes and still be minutes to Windermere and surrounding areas. Nearby luxury estates ensure your new home will fit seamlessly into this elegant neighborhood. It gets better, you will have the freedom to choose any builder you prefer. Minutes to Windermere, Hamlin, Winter Garden Village, and the 429 Expressway to Disney, Downtown Orlando, and all major shopping, restaurants, and attractions. This lot is truly a rare find, as there's nothing quite like it currently on the market. Don't miss this chance to own your piece of paradise! all measurements and zoning restrictions to be verified by the buyer/ buyers agent.

10133 Colt Lane, Winter Garden

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