Recently Sold in Winter Garden, FL

4 Beds ⋅ 6 Baths ⋅ Isles Lake Hancock Ph 02 48 06 SubDv. ⋅ 34787 Zip Code

Fall in love with this extraordinary fully renovated lakefront estate by Davila Homes, an award-winning builder known for visionary design and unmatched craftsmanship. Located in the exclusive Isle of Lake Hancock—a private, gated enclave of just 34 homes—this is a rare opportunity to own a true masterpiece with lake views in both the front and back. From the moment you enter the soaring double-height foyer, you’re greeted with sleek elegance and modern sophistication. A striking round glass staircase leads to a stylish loft, while the open-concept main floor flows effortlessly through light-filled living spaces that embrace Florida’s indoor-outdoor lifestyle. The primary suite is a showstopper—massive in scale with a walk-in closet you’ll never want to leave and a spa-inspired bathroom that feels like a private retreat. The home also features a private gym, a versatile bonus room for entertaining, and designer finishes in every corner and a rare to find eight car garage. Step outside to a resort-style lakeside lanai, complete with a screen-enclosed pool and panoramic water views. Whether you're sipping coffee at sunrise or hosting sunset gatherings, the setting is pure magic. Set on the pristine Lake Hancock chain, this is a water lover’s dream—ideal for boating, wakeboarding, and skiing with access to two world-class slalom courses. Just minutes away, Hamlin Town Center offers future dock access to shops, dining, and entertainment. And with Disney, Winter Garden, and Windermere close by, you’re at the center of it all—yet worlds away. Homes in this community almost never hit the market—and certainly not like this. If you’ve been waiting for something extraordinary, this is it. Schedule your private showing today.

14645 Isleview Drive, Winter Garden

$4,300,000

6 Beds ⋅ 6 Baths ⋅ 34787 Zip Code

Own your own Country House in the city! This unique, one-of-a-kind generational lakefront compound situated on 17+ acres is a ranch-style estate designed and inspired by Frank Lloyd Wright. This private country home is on Johns Lake, a 138-acre lake famous for bass fishing, boating and water sports. Your journey begins along a hidden, quarter-plus mile drive lined with a canopy of majestic live oaks, leading through lush tropical landscaping to a secluded country estate in the city. This compound combines 3 separate living quarters (approx. 10,000 s.q ft.) - the main home, guest cottage and mother-in-law / staff apartment in the stable block. The main pool home boasts granite countertops in the kitchen, double ovens, gas cooktop, and a work-island with direct access to the dining room. The living and dining room features a wall-to-wall picture window bathing the space with natural light and phenomenal views of the gardens and Johns Lake. The first level owners suite is highlighted by a floating copper wood-burning fireplace, expansive closets and spa-inspired bath, walk-in shower and a private office with lake views. Two spacious bedrooms, balcony and a loft are located on the 2nd level. The retractable sliding glass doors in the living room open to a screen enclosed oasis featuring a lanai, sun deck, deep, oversized pool with spa and lakefront views. The cozy and quaint cottage with detached garage is across the pond, a short walk from the main house boasting 3 bedrooms and 2 bathrooms, a full kitchen with stainless steel appliances, counter and cabinet space, and a bonus room currently used as a library and a sitting room. The fully equipped mother-in-law or staff quarters is ideal for accommodating visiting family, offering a college student independence, or providing friends with a comfortable retreat. This space offers the blend of privacy, featuring its own entrance, kitchen and bath. This compound offers so many different possibilities: a horse ranch, skeet and pistol shooting, football/ soccer/baseball/sports field/ zip lining, ATVs and private shooting berm. The shoreline of this home is a sandy beach, great for the little ones, offering a long new boat dock, with gazebo and sunning deck, ladders to allow access in and out of the lake, as well as boat hook up; an ideal set up for multi-generational living! This property offers so many features, we can’t list them all here, one more spectacular feature is the fact that you can even land a helicopter on site! You won’t find another home like this in the bustling city of Orlando, in such a wonderful location and only 20 minutes to a private airport, OIA, Disney, Universal and Shopping! This home is being sold AS-IS. Don’t miss this rare and fantastic opportunity to bring your personal touch and vision to this country estate on the water, with the serenity of lakeside living.

17017 Marsh Road, Winter Garden

$3,894,945

6 Beds ⋅ 7 Baths ⋅ Briley Farm - Phase 1b SubDv. ⋅ 34787 Zip Code

Pre-Construction. To be built. Briley Farm rests comfortably on 111 acres of lush landscape in the beautiful town of Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! Each residence will be meticulously designed to complement its natural surroundings, with spacious floor plans that flow from room to room, planned to be airy yet cozy and ready for your personal touch. At Briley Farm, you'll find a seamless combination of residential luxury and convenience, with homes built for enjoying the best of indoor and outdoor living. Briley Farm boasts serene scenery as a picturesque back drop for new home construction, while still near shopping, restaurants, and major highways. At Briley Farm you'll discover comfortable countryside living under a canopy of welcoming trees, set to embody the lifestyle for which you've been searching, all nestled away from life's demands.

517 N Pollard Street, Oakland

$3,470,000

5 Beds ⋅ 6 Baths ⋅ Briley Farm - Phase 1b SubDv. ⋅ 34787 Zip Code

Pre-Construction. To be built. Pre Construction. To be Built. Briley Farm rests comfortably on 111 acres of lush landscape in the beautiful town of Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! Each residence will be meticulously designed to complement its natural surroundings, with spacious floor plans that flow from room to room, planned to be airy yet cozy and ready for your personal touch. At Briley Farm, you'll find a seamless combination of residential luxury and convenience, with homes built for enjoying the best of indoor and outdoor living. Briley Farm boasts serene scenery as a picturesque back drop for new home construction, while still near shopping, restaurants, and major highways. At Briley Farm you'll discover comfortable countryside living under a canopy of welcoming trees, set to embody the lifestyle for which you've been searching, all nestled away from life's demands.

521 N Pollard Street, Oakland

$3,170,000

6 Beds ⋅ 6 Baths ⋅ Isles Lake Hancock SubDv. ⋅ 34787 Zip Code

Get ready to be impressed by this exceptional lakefront residence at 14511 Isleview Dr in Winter Garden, fully renovated by the renowned Davila Homes. Set directly on the pristine shores of Lake Hancock, this luxury property offers breathtaking water views and a private dock, perfect for boating, sunset lounging, or embracing the ultimate Florida lifestyle. This thoughtfully designed home features 5 spacious bedrooms, including a private mother-in-law suite ideal for multigenerational living or guests. A dedicated home office provides the perfect space for remote work or quiet study, while a fully equipped home gym adds to the home’s functional appeal. At the heart of the home is a stunning chef’s kitchen, complete with top-of-the-line appliances, custom cabinetry, and premium finishes—designed to impress both everyday cooks and seasoned entertainers alike. With refined modern design, high-end finishes, and meticulous attention to detail throughout, this residence offers an unmatched blend of luxury, comfort, and lakefront living in one of Winter Garden’s most desirable locations.

14511 Isleview Drive, Winter Garden

$3,150,000

6 Beds ⋅ 8 Baths ⋅ Shorefront Cove SubDv. ⋅ 34787 Zip Code

Under Construction. Exquisite Luxury Estate in Shorefront Cove at Horizon West. Presenting a rare opportunity to own a premier residence in the sought-after Shorefront Cove community of Winter Garden’s Horizon West. This elegant two-story estate offers 6,442 square feet of impeccably designed living space, showcasing refined luxury, modern convenience, and breathtaking views of Huckleberry Lake. Boasting 6 spacious bedrooms, 6 full bathrooms, and 2 half baths, this home features dual primary suites, one on the main level and one on the upper level, bonus room, wet bar, theater, large lanai, and 4-car garage offering ample storage and convenience. This residence provides easy access to major highways, premier shopping, dining, entertainment, and top-rated schools, all within one of Central Florida's most desirable communities. Call today to schedule a private tour.

14182 Larkspur Lake Drive, Winter Garden

$3,133,000

5 Beds ⋅ 6 Baths ⋅ Lago Vista Sub #A SubDv. ⋅ 34787 Zip Code

This privately gated elegant European architectural style custom home has been completely renovated. Beautifully sited on over five acres, directly on Johns Lake, with over 1,200 feet of lake frontage. Upon entering the home the solid mahogany front doors create a stately impression. The natural light from the clerestory windows visually link the living and dining room; highlighting the intricate stone work and beautiful ceiling detail. The plan flows smoothly into the family room, a space planned for spectacular water views and natural light, beautifully finished with a working bar and custom built-ins. The chefs kitchen offers modern convenience with granite countertops, gas cook top, custom Busby cabinetry, walk in pantry, limestone flooring, and top of the line appliances. The open arrangement and warm hues create an inviting space for friends and family to gather. With multiple access points the screened & covered lanai adds living space and features open bar/summer kitchen. The sparkling infinity pool and spa are nicely finished with and offers amazing water views. A short walk from the pool to the boat dock captures stunning sunset views with boat lift and dock. A perfect retreat the master suite captures prime views and permits access to outdoors through double sets of French doors. Massive walk in closet, garden tub, large shower, and his and hers vanities highlight the master bath. The secondary bedrooms are designed for growing families. The separate guest house/office offer flex space.

13352 Lago Vista Drive, Winter Garden

$3,050,000

7 Beds ⋅ 8 Baths ⋅ Acreage SubDv. ⋅ 34787 Zip Code

Exceptional custom estate on approximately 1.61 acres in Downtown Winter Garden's desirable Golf Cart District, just minutes from Historic Plant Street, the West Orange Trail, shopping, dining, and entertainment. This extensively renovated residence offers over 7,700 square feet of living space with 7 bedrooms, 6 full baths, 2 half baths, spacious living and entertaining areas, a chef's kitchen with premium appliances, marble countertops, wine bar, and an open-concept design. The resort-style outdoor living area features a heated saltwater pool, covered lanai, summer kitchen with pizza oven and built-in grill, and an NBA regulation half basketball court. A detached guest house with a full kitchen provides ideal space for guests, multigenerational living, or a private office. Additional features include a gated circular driveway, oversized 3-car garage with workshop, golf cart garage, mature oak trees, and no HOA. Conveniently located near SR-429, Florida's Turnpike, Winter Garden Village, downtown Orlando, area attractions, and Orlando International Airport.

900 W Plant Street, Winter Garden

$3,050,000

5 Beds ⋅ 6 Baths ⋅ Signature Lakes Prcl 01c SubDv. ⋅ 34787 Zip Code

Luxury meets laid-back lake living on Lake Hancock in Winter Garden, inside the sought-after Independence community with parks, trails, and a true neighborhood feel. Custom built by Brierhill Homes, recognized as MCBC Builder of the Year, and professionally designed/furnished by Gilmore Design Co., this exceptional direct lakefront residence sits on one of the area’s largest lots—with an oversized, fully fenced backyard—perfect for entertaining—where you can enjoy stunning sunsets over the water and catch the Disney fireworks on select nights. Arrive via an impressive circular drive and step into a striking entry featuring a custom front door, polished natural stone flooring, and a dramatic stone accent wall—framed by a deep, covered front porch with a rich wood-plank ceiling that immediately sets the tone. It’s a welcoming space that’s perfect for a small seating area to enjoy morning coffee or greet guests in style. Inside, the home is bright, elevated, and designed for both entertaining and everyday comfort, highlighted by a timeless coastal-modern palette with white oak flooring, a beautiful white oak staircase with integrated LED lighting under each step, and custom ceiling details throughout (including soffit/tray accents and integrated lighting). The layout offers 5 bedrooms, each with a private en-suite bathroom and walk-in closet, and each bedroom includes blackout honeycomb shades for comfort and privacy—including a stunning first-floor primary suite with serene lake and backyard views, plus a dedicated first-floor guest suite. You’ll also love the private office and a media room that easily works as a flex space (playroom, gym, second lounge, or homework room). At the heart of the home, the chef’s kitchen showcases Thermador appliances and a show-stopping double island topped with Cambria quartz with subtle gold veining, plus a custom chevron-designed backsplash with under-cabinet LED lighting that highlights the detail beautifully. The kitchen flows seamlessly into the main living space for true indoor-outdoor living. A wall of living room sliding glass doors opens wide, creating one expansive space that connects the interior to the lanai, pool, and lake beyond. Enjoy built-in Sonos sound in the living room and kitchen, with audio extended to the outdoor kitchen as well—plus the flex/media space is pre-wired if additional speakers are desired. The living room also features a sleek gas fireplace framed in natural stone, flanked by custom built-ins for a clean, designer finish. Out back, unwind in your private retreat with a heated pool and spa, generous covered areas, and a summer kitchen made for sunset dinners. The first-floor lanai (including the summer kitchen) and the second-floor balcony are both fully encapsulated with motorized screens controlled by remote—perfect for effortless, bug-free evenings and both outdoor living areas feature a warm wood-plank ceiling accent that brings a high-end, resort feel. Additional highlights include a whole-home water softener/filtration system (low/zero maintenance), a built-in security system with exterior cameras, built-in Sonos audio, and whole-home smart lighting with keypad controls and scene presets—plus an oversized 3-car garage. Select furniture may be purchased separately upon request.

14730 Avenue Of The Rushes, Winter Garden

$2,835,000

5 Beds ⋅ 4 Baths ⋅ Acreage SubDv. ⋅ 34787 Zip Code

Welcome to “Home Again Ranch,” your extraordinary 12+ acre farm that is around the corner from Windermere and tucked away on a quiet cul-de-sac road. You don’t need to drive hours to experience country living at its finest. This is a once in a lifetime opportunity to own a large parcel of land zoned agricultural with NO HOA in the heart of one of Central Florida’s most desirable residential areas. The charming main residence has close to 4,000 square feet under air, and includes 5 bedrooms, 4 bathrooms, bonus room, an attached two car garage, 75’ porch overlooking your private pond with dock, and a swimming pool. There is an air-conditioned steel building for your equipment, storage, or extra living space. Horses and livestock can be housed comfortably in their own barn and graze in the corrals. Bring your vision to life whether it be farming, equestrian, or just wanting a great sense of privacy away from the hustle and bustle. The residence is zoned for Lake Whitney Elementary and Sunridge Middle School which are “A” rated schools. Location can’t be beat. Just 20 minutes to Disney World & Universal Studios, 5 minutes to Downtown Windermere, 10 minutes to historic downtown Winter Garden, and 30 minutes to Orlando International Airport. Don’t miss out on this incredible life-changing residence!

12151 Walker Pond Rd, Winter Garden

$2,800,000

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

Welcome to 15699 Panther Lake Dr, a breathtaking lakefront residence. This fully furnished home has been meticulously upgraded with nearly $1 million in custom improvements, creating a one-of-a-kind luxury retreat. As you step inside, you’re greeted by a sophisticated open-concept design filled with natural light and panoramic lake views. The chef’s kitchen boasts a grand center island, premium cabinetry, and top-of-the-line stainless steel appliances—perfect for both everyday living and entertaining. The primary suite is an oasis of elegance featuring a spa-inspired bathroom and a custom-designed, oversized walk-in closet that is truly a dream come true. This boutique-style dressing room showcases floor-to-ceiling glass-front cabinetry, custom drawers with brass hardware, built-in shelving, and thoughtfully designed lighting. With its plush seating area and display shelving for luxury items, it offers the perfect blend of function and sophistication. Spacious guest bedrooms and thoughtfully appointed living areas provide comfort and style for family and friends. For those who work remotely, the home also includes a dedicated office with its own private entry—an ideal space for productivity, privacy, or meeting clients without disturbing the rest of the household. Step outdoors to a resort-style backyard that feels like your private escape. The infinity-edge pool overlooks serene water views, while the summer kitchen, fire pit, and expansive lounging areas create the ultimate space for relaxation and gatherings. Whether hosting a sunset dinner or unwinding by the fire, every detail of this outdoor paradise has been designed for luxury living. Residents of Lakeshore Preserve enjoy exclusive amenities, including a clubhouse, fitness center, resort-style pool, playgrounds, and kayak access. The community is ideally located near top-rated schools, world-famous theme parks, major highways, and premier shopping and dining destinations. This rare opportunity to own a fully customized, move-in ready lakefront masterpiece won’t last long—schedule your private tour today!

15699 Panther Lake Drive, Winter Garden

$2,775,000

5 Beds ⋅ 5 Baths ⋅ Deer Island SubDv. ⋅ 34787 Zip Code

Experience over an acre of elevated direct sunset lakefront luxury living on the naturally spring-fed waters of John’s Lake. Offered publicly for the first time, this fully custom estate represents a rare convergence of beauty, privacy and enduring design. Nearly 5,000 square feet of interior living space unfold effortlessly into an additional 1,000 square feet of exceptionally well-appointed enclosed outdoor living, creating seamless indoor to outdoor living. Positioned within the private gated enclave of Deer Island and presented in impeccable condition since its 2015 construction, the home reflects meticulous care and pride of ownership. Thoughtfully designed for a life well lived by owners and guests alike, every detail was executed with intention. Arrival is elegant and memorable, welcomed by a central fountain and expansive motor court leading to an oversized three-car garage, while two bedrooms on the main level, including the primary and guest suite, provide comfort, privacy and effortless livability for generations. Designed for entertaining, walls of fully retractable sliding glass doors dissolve the boundary between indoors and out, allowing the living and great rooms to open to the terrace beyond. The covered outdoor lounge, finished with a wood-paneled ceiling, gas fireplace and fully equipped outdoor kitchen, extends daily living outdoors. The infinity pool and spa, framed by gas fire bowls, merge seamlessly with the lake view itself, while a dedicated pool access bath enhances convenience. Privately positioned to capture sweeping lake views, the primary suite opens directly to the lanai and features dual walk-in closets. Its bath is anchored by a freestanding copper soaking tub, hammered copper sinks set within custom vanities, and a full stone walk-in shower with multiple showerheads and built-in bench. The kitchen features custom wood cabinetry, oversized island, induction cooktop, separate built-in refrigerator and freezer, professional-grade appliances, and walk in pantry. Architectural details include travertine flooring, coffered and tray ceilings, refined millwork and wrought iron staircase. All closets feature custom built-ins. The second-floor media room may also serve as a spacious fifth bedroom with private balcony overlooking the lake. Beyond the terrace, tiered gardens descend toward the shoreline, where Four Seasons marble statuary is thoughtfully placed throughout the grounds, like a work of art set within the landscape. A private putting green, fire pit and manicured lawn enhance the setting. The composite dock includes dual lifts for boat and jet ski, water and electric service, and upper level sun deck positioned for sunset views. John’s Lake spans over 2,500 acres and is known for exceptional clarity, ideal for skiing, boating, water sports and fishing. Deer Island offers gated entry with waterside tennis, pickleball and basketball courts. The home is serviced by a private well. Less than one mile from the Florida Turnpike and 25 minutes to downtown Orlando. Contact for your private viewing.

17737 Deer Isle Circle, Winter Garden

Recently Sold Listings in Winter Garden, FL

Be the First to Know About New Winter Garden Homes

Winter Garden Real Estate Map Search

All Recently Sold in Winter Garden, FL

Zen Home Group

Search

Resources

About