Homes for Sale Between $1,500,000 to $2,000,000 in Winter Garden, FL

16038 Johns Lake Overlook Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Hickory Hammock Ph 1d SubDv. ⋅ 34787 Zip Code

Commanding stunning views of Johns Lake, 16038 Johns Lake Overlook Dr rests in the desirable Hickory Hammock community of Winter Garden a lakefront enclave where natural beauty meets elevated, everyday luxury. This is more than a home; it's a lifestyle designed for those who appreciate space, comfort, and the calming presence of water just beyond their windows. Inside, 4,139 square feet unfold across a thoughtful, flexible layout with five bedrooms and five bathrooms. The main level anchors the home with two generous suites, including a refined primary and an oversized guest suite. Each offers serene water views, spa-inspired bathrooms, and a true sense of privacy that makes hosting effortless. Venture upstairs to discover a second secluded primary suite your personal sanctuary. Here, you can wake to panoramic lake views, relax in the garden bath, or step onto your private balcony to take in unforgettable sunsets over the water. The heart of the home is an open concept living area that flows seamlessly into a chef's dream kitchen. Premium appliances, gleaming granite countertops, and custom cabinetry create a space equally suited for quiet mornings and lively gatherings. When it's time to unwind, a dedicated theatre loft provides the perfect setting for movie nights and lazy weekend afternoons. Step outside, and the entertaining possibilities feel endless. The expansive outdoor living area boasts a full outdoor kitchen finished in Brazilian granite, a sparkling pool with an infinity edge hot tub, and multiple spaces for lounging and dining beneath the Florida sky. Just steps away, your covered private boat dock complete with boat and jet ski lifts opens the door to endless days of boating, fishing, and watersports on Johns Lake. For those who love to play, the backyard even includes a 5-hole putting green and a 2-hole chipping green, ideal for sharpening your short game without ever leaving home. Every detail here reflects a rare blend of craftsmanship, comfort, and connection to the water. Surrounded by natural beauty and premium amenities, this property delivers the kind of tranquil lakefront living that so many search for and so few ever find. Opportunities to own a home like this, in one of Winter Garden's most sought after communities, simply don't come along often. Come experience it for yourself, and imagine the life waiting here. Schedule your private showing today before this exceptional retreat is gone!

16038 Johns Lake Overlook Drive, Winter Garden

$1,999,000

6 Beds ⋅ 7 Baths ⋅ Avalon Ridge SubDv. ⋅ 34787 Zip Code

Built in 2024 and completely upgraded beyond builder standards, this 6-bedroom, 5-full-bath, 2-half-bath home in Avalon Ridge gives you the feel of a custom home without having to start from scratch. From the moment you walk in, you can see how much thought was put into every space. The home features custom woodwork, built-ins, upgraded flooring, designer lighting, window treatments, and fully customized closets throughout. The main floor is open, bright, and made for both everyday living and entertaining. A custom lounge near the entrance includes built-in cabinets, lighting, beverage refrigerators, extra storage, and a sitting area. The living room, dining area, and kitchen flow together and open to the covered outdoor space through large sliding glass doors. The kitchen features a large island, quartz countertops, stacked cabinets, stainless steel appliances, and plenty of storage. The same custom wood details continue into the surrounding living spaces, giving the entire first floor a finished and connected look. The primary suite is located downstairs and includes a large bathroom with dual sinks and a fully customized walk-in closet with glass doors, built-in shelving, display space, and a center island. Upstairs, there are additional bedrooms, a Jack-and-Jill bathroom, flexible rooms that can be used as guest rooms or offices, and a dedicated movie room with custom built-ins. Every closet in the home has been redone to create more usable storage. The home also includes upgraded vanities, trim, interior finishes, and wiring already in place for an electric vehicle charger. Complete plans for a custom pool are included with the sale, so the next owner can move forward with the project without having to begin the design process from the beginning, subject to approvals. Photos of pool virtually staged. Custom built-ins, installed light fixtures, window treatments, and curtains are included. Furniture and décor are not included in the list price and will be sold separately as a complete furniture package. This is a nearly new home with the upgrades, storage, and finished look that are hard to find in a standard new-construction home.

16077 Barkly Ridge Court, Winter Garden

$1,999,000

5 Beds ⋅ 5 Baths ⋅ Avalon Cove SubDv. ⋅ 34787 Zip Code

Experience lakefront living on Hickorynut Lake with expansive water and sunset views, a private covered dock, resort-style pool and exceptional indoor-outdoor living. This 5-bedroom, 5-bath residence combines direct access to a skiable lake with an impressive outdoor setting designed to make the most of the Florida lifestyle. The backyard is a standout, featuring an oversized heated saltwater pool, 8-person spa, fire feature, complete outdoor kitchen and expansive covered lanai with retractable screens. Beyond the pool, the private covered dock provides direct lake access. Enjoy boating, paddleboarding, fishing and waterskiing—or simply enjoying the sunset over the water. Inside, abundant natural light and lake views complement an open, spacious floor plan. The kitchen features an oversized island, Wolf gas range, double ovens, abundant cabinetry and an open connection to the main living areas. The first floor includes a private guest suite with full bath and walk-in closet, along with a separate bonus room offering flexible space for an office, fitness room, media room or additional living area. Upstairs, a spacious loft opens to a private balcony overlooking the lake. The primary suite captures panoramic water views and features a spa-inspired bath, oversized walk-in shower and large custom closet. Additional features include surround sound inside and out, custom window treatments, upgraded stair railings, designer lighting, a fully fenced oversized homesite and new exterior paint in 2026. Located in Winter Garden with convenient access to dining, shopping, golf, Orlando attractions, Disney and Orlando International Airport, this property brings together lakefront recreation, extensive outdoor living and a spacious, flexible interior—all in one exceptional waterfront setting.

9110 Morgana Court, Winter Garden

$1,975,000

5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34787 Zip Code

Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3,596 square feet of elegantly curated living space—where classic design meets modern sophistication. Buyers may personalize the home with a curated selection of upgrade options, including additional squarefootage, a custom pool and spa, summer kitchen, cabana, golf cart garage and storage, three-car garage, or a private garage apartment suite. Home plans, elevations, and design renderings are subject to change, with exterior finishes and roof materials influencing final elevation pricing. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.

1106 Sarah Mathews Drive, Oakland

$1,950,000

5 Beds ⋅ 6 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code

Prepare to be awed by this stunning estate from the Toll Brothers executive collection in the renowned community of Lakeshore Preserve. This home presents an ultra modern layout bringing you an environment that caters to both entertaining and every day life. The first floor is open and has 2 sets of triple pane sliding glass doors that fully open to your personal oasis. Beyond the covered lanai is a beautiful pool, spa and cabana area, perfect for a mid day swim or watching Disney fireworks at night. The kitchens, indoor and outdoor, and sure to impress even the most fastidious of chefs with the natural gas cooktop, multiple mounted range hoods, quartz countertops and more. This property is not only a "smart home" but also environmentally conscientious with newly installed solar panels and an electric car charger. All furniture is included with the sale of this home, the only thing you need is the keys to begin living your best central Florida life. Virtual Tour Available.

15680 Panther Lake Drive, Winter Garden

$1,899,999

4 Beds ⋅ 3 Baths ⋅ Oakland Hills SubDv. ⋅ 34787 Zip Code

Custom-built by Justice & Wood Builders, this 4-bedroom, 3-bathroom Modern Farmhouse sits on a rare 0.47-acre lot in Oakland Hills, an intimate community of just 17 homesites minutes from Historic Downtown Winter Garden. Towering, moss-draped oaks frame the property and set a peaceful tone from the moment you arrive. Inside, wide-plank wood floors and abundant natural light flow through an open-concept living space crowned by cathedral ceilings and exposed timber beams. The kitchen goes well beyond standard gourmet, with shaker cabinetry, quartz countertops, a massive blue-gray center island, a deep farmhouse sink, professional stainless steel appliances, and a natural gas range built for serious cooking. The bedrooms are generously sized and well separated. The upstairs bedroom is flexible enough to serve as a home office, gym, media room, or guest suite, and it has air-conditioned storage and a large walk-in attic. The bathrooms feature clean lines, modern fixtures, and custom tilework. The laundry room has extensive cabinetry, quartz counters, and a patterned tile backsplash. The three-car garage includes an EV adapter in the third bay. Out back, the fully fenced yard feels like your own resort, with a pool and spa surrounded by a spacious paver patio and a fire pit area for evenings outside. Downtown Winter Garden's Farmers Market, Plant Street Market, boutiques, and restaurants are minutes away by car or golf cart.

15210 E Oakland Avenue, Winter Garden

$1,895,000

6 Beds ⋅ 7 Baths ⋅ Avalon Rdg SubDv. ⋅ 34787 Zip Code

Virtually Staged. Built in 2024, this approximately 5,400-square-foot Winter Garden residence features six bedrooms, six bathrooms, a dedicated office, an expansive loft, a media room, and serene pond views, complemented by an extensively upgraded backyard with a custom summer kitchen. The main level includes the primary suite with two walk-in closets, a private guest suite with its own bathroom, and the office. Four additional bedrooms, the loft, media room, and a second laundry area are located upstairs, along with a covered balcony overlooking the pond. Soaring 12-foot ceilings, elegant tile flooring, and expansive living areas create a welcoming setting for everyday living and entertaining. The thoughtfully designed two-story layout balances open gathering spaces with private retreats. At the heart of the home, the gourmet kitchen features an impressive 10-by-7-foot island, quartz countertops, stacked cabinetry, and a spacious butler’s pantry. Generous preparation and serving areas make the kitchen equally suited to casual meals and larger gatherings. The main-level primary suite offers a peaceful retreat with two generously sized walk-in closets. Upstairs, the loft and dedicated media room provide flexible spaces for movie nights, recreation, and relaxing, while the covered balcony offers a quiet place to enjoy the pond views. Designed for outdoor entertaining, the fully fenced backyard features expansive paved terraces, tropical landscaping, contemporary stepping-stone pathways, and decorative stone accents. The custom summer kitchen anchors the space with a built-in grill, extensive preparation and serving surfaces, and an oversized dining island with bar seating. Multiple dining and lounge areas provide room for everything from intimate evenings to larger celebrations. A spacious covered patio extends the living space outdoors, creating a comfortable connection between the home and its thoughtfully enhanced grounds. The pond provides a scenic backdrop throughout the outdoor living areas. Residents enjoy community recreational amenities and scenic walking trails, with convenient access to SR 429, downtown Orlando, Walt Disney World, shopping, dining, and area schools. With its versatile layout, generous gathering spaces, and exceptional outdoor kitchen and entertaining areas, this home brings together comfort, thoughtful design, and the best of Florida living.

16143 Barkly Ridge Court, Winter Garden

$1,800,000

Overstreet Crate SubDv. ⋅ 34787 Zip Code

CITY OF WINTER GARDEN HAS APPROVED A NEW OVER LAY ALLOWING 10 UNITS PER GROSS ACRE HIGH DENSITY ZONING~THIS PART OF A BEAUTIFCATION OF EAST WINTER GARDEN AREA MAY ALLOW FOR ADDITTIONAL FINANCIAL INCENTIVES FOR THE DEVELOPER~THE PROPERTY IS 1.8 ACRES, ZONED FOR 10 UNITS PER ACRE, AND IS LOCATED ACROSS FROM THE AUTO AUCTION, ADJACENT TO THE CROWN, CORK AND SEAL, VERY CLOSE TO HIGH TECH INDUSTRIAL PARK, AND NEW APARTMENT COMPLEX OFF OF PLANT STREET. QUICK ACCESS TO THE 429 AND HWY 50, WITHIN 2 MILES FROM DOWNTOWN HISTORIC WINTER GARDEN. PROPERTY IS BEING SOLD "AS IS" SEE ATTACHMENTS FOR MORE INFORMATION~CITY OF WINTER GARDEN WILL LOOK AT DRAWINGS OF DEVELOPMENT PROPOSAL TO APPROVE ANY ZONING CHANGES~HIGHLY DESIRABLE HISTORIC WINTER GARDEN LOCATION~WINTER GARDEN EAST SIDE DEVELOPMENT OVERLAY IN PLACE.

1211 E Maple Street, Winter Garden

$1,799,000

4 Beds ⋅ 5 Baths ⋅ Oakland Parkb-2 SubDv. ⋅ 34787 Zip Code

Beautifully crafted by J&J Building, this exceptional 4-bedroom, 4.5-bath custom home combines thoughtful design, elegant finishes, and effortless indoor-outdoor living. Situated on a desirable corner lot, the home is filled with incredible natural light and offers a layout designed for both everyday comfort and entertaining. At the heart of the home, the stylish kitchen is complemented by a wet bar and a full scullery (back kitchen) with a second refrigerator, oven, sink and built-in pantry, creating the perfect blend of style and functionality. The main-level primary suite provides a private retreat, while three additional upstairs bedrooms each feature their own en-suite bathroom, offering comfort and privacy for family and guests alike. The downstairs office and upstairs loft area also provide flexible options to meet all your needs. The oversized attic storage with drop down stairs is perfect for all your seasonal items! Step outside to your own private oasis through the huge pocketing sliding glass doors, and enjoy the salt water pool, spa, and inviting outdoor living space with automated retractable screens—ideal for enjoying Florida living year-round. And the large garage has 2 EV plugs and 2 garage doors- 1 perfect for your golf cart! Just across the street, a beautiful pond provides a peaceful natural backdrop, with scenic sunset views and abundant wildlife adding to the home's special setting. Enjoy an exceptional lifestyle just steps from the West Orange Trail and within the Golf Cart District, offering convenient access to downtown Winter Garden's charming shops, restaurants, and vibrant community atmosphere. A rare opportunity to enjoy custom craftsmanship, beautiful surroundings, and an unbeatable location—all in one remarkable home.

900 Allendale Lane, Oakland

$1,749,000

5 Beds ⋅ 5 Baths ⋅ Garden West SubDv. ⋅ 34787 Zip Code

Welcome to this stunning custom home crafted by the renowned Pioneer Builders in 2022, nestled in one of Winter Garden's most coveted locations. Just steps from the beloved West Orange Trail and the charming Golf Cart District of Historic Downtown Winter Garden, this home offers the best of the Winter Garden lifestyle right at your doorstep. Whether you're pedaling the trail at sunrise or cruising downtown in your golf cart for dinner and live music, this location makes it easy to enjoy everything this vibrant community has to offer. From the moment you step inside, the quality and craftsmanship are undeniable. Engineered hardwood floors flow seamlessly throughout the home, while custom cabinetry adds timeless elegance to every space. The open living areas feature top-of-the-line Fisher & Paykel appliances, blending elevated design with everyday functionality. Plantation shutters throughout the main house add a classic, refined touch, while an automatic gate provides an added layer of privacy and convenience. The main level features a private ensuite bedroom and full bath, ideal for guests or multigenerational living, along with a convenient powder bath for visitors. Upstairs, the primary suite serves as a true retreat, complete with two oversized walk-in closets and a luxurious ensuite bath. Two additional bedrooms share a well-appointed Jack-and-Jill bathroom, while an upstairs laundry room adds everyday convenience. Added in 2024, the private apartment above the garage is a rare and exceptional bonus, complete with a kitchenette, dedicated office space, full bath, and in-unit laundry. Whether envisioned as a private guest suite, in-law quarters, a dedicated work-from-home retreat, or an income-producing rental, the possibilities are endless. Winter Garden's Golf Cart District is more than a novelty—it's a way of life. Residents enjoy cruising to the award-winning Farmers Market, exploring boutique shops and local restaurants, visiting breweries, and taking part in the community events that make Historic Downtown Winter Garden one of Central Florida's most vibrant destinations. The West Orange Trail, spanning more than 22 miles of scenic, paved pathways, is a paradise for cyclists, joggers, and walkers. With this home's prime proximity, outdoor recreation is always within easy reach. This is more than a home—it's a lifestyle. Don't miss the opportunity to own a distinctive property offering timeless finishes, versatile living spaces, added privacy, and an exceptional location in one of Central Florida's most sought-after communities.

728 Garden West Terrace, Winter Garden

$1,699,900

5 Beds ⋅ 4 Baths ⋅ Oakland Park B-2 SubDv. ⋅ 34787 Zip Code

Welcome home to calm, light-filled luxury on a peaceful pond in the sought-after golf cart district—just steps from the West Orange Trail and 3 miles to historic Downtown Winter Garden. This 4-bed, 3-bath custom home sits on a large lot and features an open, airy floor plan with upscale laminate flooring throughout. The gourmet kitchen is built to entertain: commercial-grade hood, gas range, Bosch appliances, pot filler, walk-in pantry, and appliance garage. Fully retractable sliding glass doors open the living area to the outdoors, with surround sound and custom-tinted windows adding comfort and privacy. One bedroom is on the main level; upstairs offers a Jack-and-Jill suite plus a private primary retreat with tray ceiling, spotlight accents, walk-in shower, soaking tub, and a stunning light-filled built-in closet. A rare bonus: a private in-law suite above the garage with its own kitchen, living area, bedroom, and stackable laundry—ideal for guests or multi-generational living. Outside, escape to your own oasis surrounded by bamboo, olive, lime, and persimmon trees, with a covered patio, full fencing, and even rocket launch views from your backyard. Unbeatable location. Unmatched lifestyle. Schedule your private showing today.

906 Allendale Lane, Oakland

$1,699,000

5 Beds ⋅ 5 Baths ⋅ Hull Island/Oakland SubDv. ⋅ 34787 Zip Code

Virtually Staged. Back on the market due to buyer financing falling through. Welcome to this exceptional lakefront retreat on the shores of Lake Apopka, where breathtaking water views, luxury upgrades, and exceptional outdoor living come together to create the ultimate Florida lifestyle. Offering 5 bedrooms, 4.5 bathrooms, and over 4,000 square feet of thoughtfully designed living space, including a convenient first-floor bedroom, this beautifully updated residence showcases extensive high-end improvements throughout, creating a move-in-ready experience for the next owner. From the moment you arrive, you'll appreciate the extensive upgrades throughout the home, including porcelain tile throughout the main living areas on the first floor, engineered white oak hardwood flooring throughout the second level, a custom wood and iron staircase, upgraded cabinetry, quartz countertops, designer finishes, and a beautifully appointed kitchen featuring premium KitchenAid appliances, a gas cooktop, and custom soft-close cabinetry. Designed for both everyday living and entertaining, the backyard is a true showpiece. Enjoy a resort-style saltwater pool and spa, gas-heated for year-round enjoyment, expansive outdoor living areas, and a fully equipped summer kitchen featuring premium Blaze appliances. Electric screens allow you to enjoy outdoor dining and entertaining comfortably while taking in the peaceful lakefront setting and stunning sunset views. Boating enthusiasts will appreciate the private dock complete with a 5,000-pound boat lift, offering direct access to Lake Apopka, one of Florida's largest lakes. With more than 30,000 acres of open water to explore, the lake offers endless opportunities for boating, fishing, watersports, and unforgettable sunset cruises. Known for its trophy bass fishing, abundant wildlife, and expansive waterfront views, Lake Apopka provides a rare opportunity to enjoy true lakefront living with the freedom and space that few Central Florida lakes can offer. This property delivers the waterfront lifestyle Florida is known for. Additional highlights include a convenient first-floor bedroom, a second-floor laundry room, solar panels that will be paid off at closing, natural gas service, a Culligan water filtration system, dual pool pumps, and city sewer, a significant advantage for a waterfront property. Ideally located just minutes from Downtown Winter Garden, shopping, dining, and major roadways, this exceptional lakefront residence offers the perfect balance of luxury, recreation, and everyday convenience. Exclusive Buyer Incentive! Take advantage of a seller-offered 2-1 interest rate buydown when financing through our preferred lender, Home First Lending, allowing qualified buyers to enjoy a lower interest rate during the first two years! Buyers may also qualify for a lender credit equal to 1% of the loan amount toward closing costs, plus a lender-paid appraisal. An incredible opportunity to make homeownership more affordable! Subject to lender approval, loan eligibility, and program terms.

1144 Hull Island Drive, Winter Garden

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