Wintermere Pointe Homes for Sale

2242 Wintermere Pointe Drive, Winter Garden

If you’ve been searching for a spacious Winter Garden home with a private pool, peaceful conservation views and room for everyone, this former model may be exactly what you’ve been waiting for! With 5 bedrooms, 4 full bathrooms and the potential for a 6th bedroom, this home combines privacy, flexibility and Florida indoor-outdoor living in a way that’s increasingly difficult to find. Situated on a peaceful wooded conservation lot, the home has been thoughtfully updated with a renovated kitchen, LVP flooring throughout the first floor, and new carpet and paint upstairs. Generous living and dining areas provide plenty of room for everyday living and entertaining, while the family room features easy access to the screened pool and deck. The spacious primary suite includes a private sitting area and built-in shelving, creating a comfortable retreat. Upstairs, the oversized bonus room with its own adjoining full bathroom offers exceptional flexibility and could serve as a second primary suite, private guest quarters, media room or game room. Need even more space? The downstairs office could potentially be converted into a 6th bedroom, making this floor plan adaptable to a variety of needs. Step outside to one of the home's most appealing features—the screened-in pool and deck overlooking the wooded conservation area. With no immediate rear neighbor, it's a private setting for morning coffee, afternoons by the pool, entertaining friends or simply relaxing at the end of the day. Located in the beautiful gated Wintermere Pointe community, this home brings together the space, privacy and flexibility along with a private pool and conservation setting that can be difficult to find. Call and schedule your private showing today!

2242 Wintermere Pointe Drive, Winter Garden

Listing courtesy of NEXTHOME BEST RESULTS REAL ESTATE. 352-740-7600

$925,000

5 Beds ⋅ 3 Baths ⋅ O6436619 MLS

5 bedrooms. 3 full baths. Nearly 3,740 SF. 3-car garage. Private screened pool. Gated community. Newer roof and A/C. Minutes from Winter Garden Village, AdventHealth, SR-429, the Florida Turnpike, Historic Downtown Winter Garden, and convenient to Walt Disney World. This is the combination buyers spend months trying to find. Set behind the gates of Wintermere Pointe, 2491 Prairie View Drive brings together a flexible five-bedroom floor plan, multiple living and entertaining spaces, private outdoor living, and a connected Winter Garden location with shopping, dining, healthcare, major roadways, and entertainment within easy reach. Step inside and the scale is immediately apparent. Soaring ceilings rise above formal living and dining rooms, leading to a spacious family room anchored by a striking dual staircase. Large sliding glass doors frame the greenery and blue waters of the pool beyond. At the center of the home, the updated gourmet-style kitchen offers stainless steel appliances, abundant cabinetry and counter space, a prep island, casual seating, and views toward the pool and backyard — creating a natural flow between cooking, gathering, and outdoor entertaining. A first-floor bedroom and nearby full pool bath provide valuable flexibility for guests, extended family, multigenerational living, or a private office. Upstairs, two separate loft areas provide space for a media room, game room, second living area, or quiet retreat. The larger opens directly onto an expansive second-story balcony overlooking the pool. An oversized bonus bedroom above the garage, incorporated as a builder upgrade, joins two additional bedrooms and a shared full bath. The naturally bright primary suite features dual walk-in closets and an ensuite with separate vanities, soaking tub, and walk-in shower. Outside, the Florida lifestyle takes over. A private screened pool and covered lanai extend the living space outdoors, with additional yard beyond the enclosure and the second-story balcony above. A generous driveway and three-car garage provide valuable parking and storage, while a newer roof and A/C add two significant improvements already in place. Wintermere Pointe offers the privacy of an established gated community with Winter Garden Village, AdventHealth, shopping, dining, and everyday conveniences nearby. Quick access to SR-429 and the Florida Turnpike keeps Central Florida connected, with Historic Downtown Winter Garden and Walt Disney World conveniently accessible. What makes this home compelling isn't any one feature. It's how rarely they come together. Nearly 3,740 SF. Five bedrooms. First-floor guest space. Two lofts. Oversized bonus bedroom. Expansive balcony. Private screened pool and lanai. Three-car garage. Newer roof and A/C. Gated community. Prime Winter Garden location. You don't have to choose between space and location, indoor and outdoor living, or rooms for everyone and places to come together. It's already here. If this is the combination you've been waiting to find, 2491 Prairie View Drive deserves to be seen.

2491 Prairie View Drive, Winter Garden

Listing courtesy of COMPASS FLORIDA LLC. 407-203-9441

2157 Wintermere Pointe Drive, Winter Garden

$765,000

5 Beds ⋅ 4 Baths ⋅ TB8532509 MLS

Welcome to this beautifully renovated residence offering an additional den, approximately 3,197 square feet of comfortable living space, and a two-car garage. Set on an oversized 0.29-acre lot in the gated Wintermere Pointe community, this home blends generous living areas with thoughtful, contemporary upgrades. Inside, you’re greeted by a bright, open layout finished with fresh neutral colors, crown molding, updated lighting, and attractive flooring throughout the main living areas. The floor plan provides multiple spaces for entertaining, dining, working from home, or simply relaxing. The completely redesigned kitchen serves as the heart of the home, featuring:Extensive shaker-style cabinetry, Dramatic stone countertops, Classic subway-tile backsplash, Under-cabinet lighting, Stainless-steel appliances, Double wall ovens, Contemporary range hood, Oversized waterfall island with abundant workspace and storage, built-in window seat with additional cabinetry, Separate beverage area with wine storage and beverage refrigerators. The kitchen opens naturally to the expansive living and dining areas, creating an inviting atmosphere for everyday living and gatherings. Large windows and sliding glass doors bring in natural light and offer easy access to the outdoor living space and spacious backyard. The first-floor den provides a versatile area that can serve as a home office, study, media room, or guest retreat. With five bedrooms and four bathrooms, the home offers comfortable accommodations and a layout designed for both privacy and flexibility. The upstairs layout includes a spacious bonus area that can easily be converted into a movie theater room. With existing built-in cabinetry and space for a refrigerator or beverage center, it’s an ideal setup for a private entertainment space, gaming room, or family media lounge. This home is located in one of Winter Garden’s highly regarded school zones, serving: Lake Whitney Elementary School, SunRidge Middle School, West Orange High School. Families appreciate the strong academic reputation and convenient proximity to these schools. This area is Prime Winter Garden Location. Just minutes from Winter Garden Village, shopping, dining, entertainment, and major roadways—including SR 429, Florida’s Turnpike, and SR 408—this move-in-ready home offers space, style, and accessibility in one of Winter Garden’s established gated communities. Schedule Your Private Showing Come experience the comfort, upgrades, and welcoming atmosphere of this beautifully updated Winter Garden home.

2157 Wintermere Pointe Drive, Winter Garden

Listing courtesy of SOUTH EARTH REALTY LLC. 8134180030

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The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of the Dayton Area Board of Realtors® MLS IDX Database. Real estate listings from the Dayton Area Board of Realtors® MLS IDX Database held by brokerage firms other than Coldwell Banker Realty are marked with the IDX logo and are provided by the Dayton Area Board of Realtors® MLS IDX Database. Information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in. Copyright© 2026 Dayton Area Board of Realtors®

Wintermere Pointe - Winter Garden Florida Homes for Sale

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Wintermere Pointe Homes for Sale

Wintermere Pointe - Winter Garden Florida Homes for Sale

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