Winter Garden Real Estate

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

Welcome to your dedicated resource for Homes for Sale Between $2,000,000 to $2,500,000 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 $2,000,000 to $2,500,000 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 $2,000,000 to $2,500,000

880 W Plant Street, Winter Garden
$2,500,000
34787 Zip Code
Introducing a once-in-a-generation opportunity on Winter Garden's coveted Plant Street in Downtown Winter Garden's Golf Cart District. Opportunities like this on Plant Street don't come around often - and rarely at this scale. This offering combines four contiguous parcels totaling 2.73 acres of Low Density Residential land - less than one mile from shops, restaurants, and Downtown Winter Garden's weekly Farmers Market. Within walking distance, enjoy access to the 22-mile West Orange Trail, where 55,000 to 60,000 pedestrians, cyclists, and skaters traverse every single month. Assembled acreage of this size and location rarely comes available in Winter Garden. Whether you're a builder or developer looking to create a boutique residential enclave, or a private buyer dreaming of a custom estate just steps from downtown, this property offers the space, setting, and zoning flexibility to make it happen. Live where golf carts double as the neighborhood's favorite mode of transportation, where tree-lined streets lead straight into historic downtown, and where the West Orange Trail connects you to miles of biking and walking through Central Florida's most charming small town. Contact us for a private viewing today! **Existing structure is currently tenant-occupied. Appointments are required to access the property. Do not visit the property without a confirmed appointment.**

880 W Plant Street, Winter Garden
15505 Shorebird Lane, Winter Garden
$2,500,000
6 Beds ⋅ 7 Baths ⋅ Lakeshore Preserve Ph 4 SubDv. ⋅ 34787 Zip Code
This extraordinary lake-view residence redefines luxury, comfort, and sophistication in the heart of Winter Garden. Located in the highly sought-after Lakeshore Preserve community, this stunning home impresses from the moment you arrive with an elegant paved driveway, beautifully manicured landscaping, and grand double entry doors leading into a dramatic two-story foyer with soaring ceilings and an unforgettable first impression. Designed for exceptional living and entertaining, the home features a sophisticated open-concept floor plan filled with abundant natural light and breathtaking lake views that create a serene and picturesque atmosphere throughout the property. The elegant dining area showcases stunning views of the pool and lake, creating the perfect setting for memorable gatherings with family and friends. The gourmet kitchen is truly a chef’s dream, featuring granite countertops, a spacious center island with seating, stainless steel appliances, designer tile backsplash, and a large walk-in pantry with custom built-in shelving. Overlooking the expansive living room, the space is enhanced by tray ceiling details and elegant recessed lighting, offering both warmth and sophistication. Sliding glass doors seamlessly connect the indoor and outdoor living spaces, opening to a spectacular pool deck and outdoor gourmet area designed for the ultimate Florida lifestyle. Relax while enjoying peaceful water views from your private backyard oasis — the perfect place to entertain, unwind, and enjoy Florida sunsets over the lake. The luxurious primary suite serves as a private retreat, featuring a spa-inspired bathroom with modern square sinks, a soaking tub, and a spacious walk-in rain shower. A separate laundry room provides ample cabinetry and additional storage for convenience and organization. Residents of Lakeshore Preserve enjoy outstanding resort-style amenities, including a clubhouse, resort-style swimming pool, fitness center, yoga room, playgrounds, dog park, sand volleyball court, fishing pier, and community canoes and kayaks. The HOA also maintains the community common areas, allowing for a truly low-maintenance lifestyle. Ideally located just minutes from Orange County National Golf Center, Walt Disney World Resort, premier shopping, dining, top-rated schools, and major highways, this impeccably maintained lakefront-inspired home offers the perfect combination of luxury, convenience, and lifestyle. A rare opportunity to own an exceptional lake-view home in one of Winter Garden’s most desirable communities.

15505 Shorebird Lane, Winter Garden
13377 Lake Butler Boulevard, Winter Garden
$2,500,000
34787 Zip Code
Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with approximately 844 linear feet of lakefront property on Lake Roper. Home could also be rebuilt as a multigen and could be larger if needed with ample room for multiple garage spaces as well (example of possible home and floor plan attached in photos). This is a RARE OPPORTUNITY to acquire this much lakefront property and land but be in close proximity to city center, major thoroughfares, restaurants, theme parks, international airports. Example photos of possible home and floor plan provided by custom home builder, David Konkol Custom Homes.

13377 Lake Butler Boulevard, Winter Garden
13377 Lake Butler Boulevard, Winter Garden
$2,500,000
4 Beds ⋅ 5 Baths ⋅ 34787 Zip Code
Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with approximately 844 linear feet of lakefront property on Lake Roper. Home could also be built as a multigen and could be larger if needed with ample room for multiple garage spaces as well. This is a RARE OPPORTUNITY to acquire this much lakefront property and land but be in close proximity to city center, major thoroughfares, restaurants, theme parks, international airports. Value is in the land -- get a free house!

13377 Lake Butler Boulevard, Winter Garden
907 Celadon Street, Winter Garden
$2,495,000
6 Beds ⋅ 6 Baths ⋅ Oakland Parka SubDv. ⋅ 34787 Zip Code
Lake Apopka view. Protected Conservation. Detached Guest apartment. Apartment over garage. In-Law suite. Multi-generational living. EV charging station. All this perfectly describes the unique differences of 907 Celadon. The main home highlights include a massive open floor plan, oversized Chef's kitchen, first-floor primary en suite, outdoor summer kitchen, two rooms directly off the foyer offering flexibility for an executive office, or two home offices, or one room as the downstairs en suite for guests or aging family members. The nearly 41-foot screened porch, with built in summer kitchen. The Detached Guest House is 907 Sq Ft, and open studio layout, one bedroom, kitchenette, full bath. Provides flexibility as the in-law suite. Chef's Kitchen offers generous workspace for more than one cook. Kitchen-Aid ovens and built-in ice maker by Manitowoc. Expansive sliding glass doors open the great room to the green conservation and Lake Apopka views. A long back yard overlooking a deep conservation vista. The first-floor primary en suite occupies its own wing at the rear and right side of the home. A door from the kitchen closes the wing from the rest of the first floor, while the bedroom opens directly to the lanai. The bathroom features frameless shower, free standing soak tub, and dual sinks across from each other. A custom walk-in closet dressing room —with extensive built-ins, a center island and chandelier complete the wing. Upstairs, three bedrooms and an oversized loft provide the flexibility for a home theater, gaming and homework stations. Daily routines are easier here. Bright blue ockers off the mudroom keep backpacks, sports equipment, shoes and bags organized, while the large laundry room includes a specialty built-in dog wash station. Connected to the main residence by a covered breezeway, the 907 Sq ft detached guesthouse/ADU sits above a 3-car garage and includes a kitchenette, full bath and closet. The garage also includes a golf-cart bay, and EV charging station. The guest house is currently used as a private executive office. Oakland Park and Winter Garden's golf-cart approved community zones is one of the signature advantages, offering easy access to Historic Downtown Winter Garden—Plant Street, the Farmers Market, dining and Crooked Can—just a golf cart ride from home. Direct access to the West Orange Trail offers 22 miles for walking, jogging and biking, plus community pools and green spaces.

907 Celadon Street, Winter Garden
1134 Prado Lane, Oakland
$2,495,000
5 Beds ⋅ 8 Baths ⋅ Grove/Oakland SubDv. ⋅ 34787 Zip Code
Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stunning 4,433 square foot Citrus floorplan by Element Home Builders delivers an extraordinary standard of luxury estate living. Every detail speaks to a level of craftsmanship and thoughtfulness that simply cannot be replicated. Five generously sized bedrooms, each with its own private ensuite bath, provides unmatched comfort and privacy for family and guests alike. Two additional powder baths serve the main living areas, while a dedicated pool bath keeps the outdoor experience seamless. At the heart of the home, a dramatic double island kitchen commands attention — equal parts showpiece and hardworking hub — crowned by soaring coffered ceilings that lend architectural depth and timeless elegance throughout. Step outside to your own private resort, where a sparkling pool and spa, summer kitchen, and covered lanai with roll-down screens create the ultimate Florida lifestyle — open-air breezes or a fully enclosed retreat, all at the touch of a button. Beyond your front door, The Grove places you steps from The Harvest District's boutique shops and restaurants, with exclusive access to the resort amenities at nearby Briley Farm — all reachable by foot or golf cart.

1134 Prado Lane, Oakland
17902 Seidner Road, Winter Garden
$2,470,000
Lake Avalon Groves Rep SubDv. ⋅ 34787 Zip Code
The most amazing site for a huge estate home in Orange County! This gem is minutes to Windermere, the new Hamlin town center and everywhere you want to be. This 10 acre property in the Lake Avalon rural settlement, sits on the highest elevation in West Orange County, which affords it incredible views in every direction. You can see all the way to Orlando, Windermere, and the nightly Walt Disney World fireworks. The property comes with a contract in place for reclaimed water for irrigation, a clean well on the property for drinking water, and electricity is already in place. This lot is a rare find! All high and dry, zoned A and ready for your custom home.

17902 Seidner Road, Winter Garden
7747 Green Mountain Way, Winter Garden
$2,400,000
6 Beds ⋅ 7 Baths ⋅ Summerlake Pd Ph 3a SubDv. ⋅ 34787 Zip Code
Welcome to an exceptional waterfront residence on beautiful Lake Hancock in Winter Garden. Offering over 5,100 square feet of living space, this impressive 6-bedroom, 6.5-bath home features a 3-car garage and direct lake frontage. Designed for both everyday comfort and effortless entertaining, the home welcomes you with a dramatic two-story family room, expansive living areas, and two primary suites—one conveniently located on each level. At the heart of the home, the gourmet kitchen features granite countertops, an oversized curved island, double ovens, a cooktop, and an open dining area ideal for gathering with family and friends. Upstairs, additional bedrooms and a generous game room provide exceptional flexibility for family, guests, a media space, or recreation. Step outside to the screened lanai, complete with a summer kitchen, and take in the serene views of Lake Hancock. In the evenings, enjoy views of Disney’s fireworks from the comfort of your own home—an unforgettable touch to this exceptional Florida lifestyle. With generous indoor and outdoor living spaces and a remarkable waterfront setting, this Winter Garden home offers an ideal combination of space, comfort, and lakefront living. Schedule your private showing today and experience it for yourself.

7747 Green Mountain Way, Winter Garden
7301 Wild Blackberry Trail, Winter Garden
$2,400,000
6 Beds ⋅ 5 Baths ⋅ Signature Lks-Pcl 01d Ph 02 - Independence SubDv. ⋅ 34787 Zip Code
Virtually Staged. This statuesque Mediterranean home is perfectly placed along Hancock Lake for maximum lakefront enjoyment. Your private covered dock protects a 20’ +/- boat w/lift as well as the lifts for 2 jet skis. Motor boat or pontoon around the lake, bring your favorite fishing rod or ski on one of the nicest skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, one of a few lakefront properties in the neighborhood that have one, manicured gardening beds for your green thumb and room for outdoor activities and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry and a delightful custom salt pool showcasing a water slide, fiber optic lighting, solar heated spa and pool ledge. Enjoy the lake views then after sunset, pull down the projector screen for your favorite flick before watching the nightly fireworks show from the Disney park. The home's exterior and interior were freshly painted. Notice the wide baseboards and crown trim throughout. Spectacular front entrance with impressive light fixtures that accentuate the formal living and dining areas and frame your first glimpse of the lake. Impressive, upgraded Double Pane Low E sliding doors showcase the patio and lake then pocket to merge your spaces. The Kitchen is equipped with multiple food prep areas, generous walk-in pantry, and a central island workstation with seating for informal gatherings. A hallway behind the Kitchen shares the cabana bath and another first floor bedroom or den or office with a sliding door to the patio and a sizable walk-in closet. The first level’s primary suite has private patio access too and a lovely bay window styled seating area. (The previous owners used this primary as a media room complete with surround sound that remains intact). The loft also has new sliding doors to the screened balcony area overlooking the patio and lake along with projection equipment and bar/kitchen ideal for entertaining. The upper level contains a large ensuite with a private balcony, another ensuite, two bedrooms that share a hall bath and another bedroom with a private balcony overlooking the patio. The security system is located in the upstairs laundry room. Both A/C Systems, all patio doors, exterior balcony railings secured and LR/DR bamboo engineered hardwood flooring are updates you'll appreciate. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy. Plans for the new satellite elementary campus of Windemere Preparatory School are underway that will be located less than 2 miles from this home. ***Photos of fireworks and formal dining area are THE ONLY PHOTOS virtually staged.

7301 Wild Blackberry Trail, Winter Garden
15633 Panther Lake Drive, Winter Garden
$2,395,000
4 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code
**Organic Modern Design. Intelligently Connected. Effortlessly Luxurious.** Discover extraordinary lakefront living in Winter Garden's Lakeshore Preserve community. Reimagined with nearly $1 million in renovations, this stunning residence blends sophisticated design, intelligent technology, and five-star resort-inspired living. Featured in *The Local Magazine's 2026 Home Issue*, the home showcases organic modern design with European and Mediterranean influences. Limewash walls, graceful archways, wide-plank flooring, custom millwork, and designer lighting create a warm, sophisticated atmosphere. A sculptural staircase with sweeping curved walls and a dramatic cascading chandelier makes an unforgettable statement. The beautifully appointed kitchen features custom cabinetry, premium JennAir appliances, a double-stacked quartz island, quartz backsplash, and beverage refrigeration. A walk-in pantry and drop zone add functionality. The primary suite offers a spa-inspired bath with a freestanding soaking tub, programmable shower, and custom California Closets. Additional highlights include a designer laundry room, upstairs entertainment loft, and equipped home gym with sauna. What truly sets this home apart is its seamless integration of technology. Control4 automation connects customizable Philips Hue lighting, Sonos audio, motorized shades, smart thermostats, security, and other features, making everyday luxury feel effortless. Outdoors, an infinity-edge pool with cascading waterfall overlooks Panther Lake. A two-level pool deck, covered entertaining areas, outdoor fireplace, integrated speakers, and motorized lanai screens create a private resort experience. Architectural lighting and a mosquito misting system add comfort and ambiance. Additional features include a whole-house generator, climate-controlled garages, EV charging, extensive security, and a professional smart-home technology transfer service for the new owner. Lakeshore Preserve offers included lawn care and a convenient location near Walt Disney World and SR 429

15633 Panther Lake Drive, Winter Garden
1146 Prado Lane, Oakland
$2,360,990
5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34787 Zip Code
Under Construction. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floor plan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Heath Stone also features a 2-car detached garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30,000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Hearth Stone model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.

1146 Prado Lane, Oakland
14656 Pylon Court, Winter Garden
$2,300,000
7 Beds ⋅ 7 Baths ⋅ Isles/Lk Hancock Ph Iii SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful lake-view home in the desirable, gated Isles of Lake Hancock community in Horizon West / Winter Garden! This spacious 7-bedroom, 6.5-bathroom home offers approximately 4,634 square feet of living space on an oversized 0.43-acre lot, with beautiful lake views from both the front and back of the property. The first floor features a spacious primary suite with a sitting area and his-and-hers walk-in closets, three additional bedrooms with bathrooms, and a separate office perfect for working from home, and a formal dining area for family meals and entertaining.The split-bedroom floor plan offers added privacy and flexibility. Upstairs, you'll find three more bedrooms, two bathrooms, and a den, providing plenty of space for family and guests. The home also offers two separate garage spaces, with one currently enclosed and used as a gym that can be converted back into a garage if desired. Enjoy Florida living with a screened-in pool, summer kitchen, solar panels, and beautiful sunset views over the lake. Residents of this gated community enjoy tennis courts, playground and a private boat ramp. Lake Hancock is a nationally recognized water-skiing destination that hosts world-class tournaments. Located in the sought-after Horizon West / Winter Garden area, the community offers convenient access to Walt Disney World, shopping, dining, upscale golf courses, top-rated schools, and SR-429. With plenty of space, beautiful lake views, and a great location, this home has so much to enjoy. Schedule your private showing today!

14656 Pylon Court, Winter Garden
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