Windermere Real Estate

Welcome to Windermere, a picturesque subdivision nestled in the heart of Orange County, Florida. Known for its charming small-town atmosphere and stunning natural beauty, Windermere offers a unique blend of luxury living and serene landscapes. This idyllic community is surrounded by shimmering lakes and lush greenery, making it a perfect haven for outdoor enthusiasts and families alike.

Windermere is renowned for its upscale homes that boast modern designs and spacious layouts, catering to a variety of lifestyles. Whether you’re seeking a cozy single-family residence or a grand estate, this subdivision has something to offer for everyone. The tree-lined streets and well-manicured lawns create a welcoming environment that encourages community engagement and fosters lasting friendships among neighbors.

One of the highlights of living in Windermere is its proximity to exceptional recreational opportunities. The area is dotted with parks, walking trails, and waterfront access, perfect for weekend picnics or leisurely strolls. Residents can enjoy the stunning views of the Butler Chain of Lakes, which provides ample opportunities for boating, fishing, and water sports.

Windermere also boasts a vibrant local culture, with charming boutiques, cafes, and restaurants that reflect the community's character. The renowned Windermere Farmers Market is a must-visit, offering fresh produce and artisanal goods every weekend.

With its blend of natural beauty, luxurious living, and a strong sense of community, Windermere is not just a place to live; it’s a lifestyle waiting to be embraced. Experience the charm and elegance of this enchanting subdivision, where every day feels like a vacation.

Newest Listings in Windermere

$1,995,000

6 Beds ⋅ 6 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code

Welcome to 4282 McKinnon Rd, a beautifully updated Windermere estate offering exceptional space, privacy, and flexibility on approximately 1.15 acres—with NO HOA. Featuring 6 bedrooms, 6 baths, nearly 5,900 square feet of living space, a private pool, and 3-car garage, this custom home combines an impressive floor plan with extensive recent improvements. Move-in ready and refreshed inside and out, the home features new windows and doors, new interior and exterior paint, new flooring, new AC systems, a new water heater, and a beautifully renovated pool. The thoughtfully designed floor plan is a standout, beginning with a spacious first-floor primary suite offering privacy and convenience. Also on the main level is a separate guest suite, ideal for visitors or multigenerational living, along with a private dedicated office for working from home. Generous living and entertaining spaces are filled with natural light, while the spacious kitchen offers abundant cabinetry, a center island, walk-in pantry, breakfast bar, and casual dining area. Upstairs, a junior primary suite with a private balcony creates another inviting retreat. Additional bedrooms provide plenty of room for family and guests, while the large bonus room over the garage offers endless possibilities as a home theater, game room, fitness studio, playroom, or additional living space. Step outside to enjoy the Florida lifestyle from the covered lanai and renovated private pool, surrounded by an expansive homesite and mature landscaping. With over an acre to enjoy and NO HOA, there is a rare sense of freedom, privacy, and breathing room. Offering extensive updates, multiple bedroom suites, a private office, oversized bonus room, pool, 3-car garage, over an acre of land, and NO HOA, 4282 McKinnon Rd delivers an exceptional combination of space and versatility in sought-after Windermere.

4282 Mckinnon Road, Windermere

$2,099,000

6 Beds ⋅ 6 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code

Seller is offering up to $40,000 toward Buyer’s allowable closing costs, prepaids, and/or rate buy-down with acceptable offer. Pool Possibility! The accompanying video has been digitally altered to illustrate what the property could look like with a pool added. The property currently does not include a pool; however, there is potential to add one.... Come experience the character and charm of Historic Olde Windermere in a home that simply cannot be duplicated. Thoughtfully custom-built, this one-owner Transitional Craftsman residence blends timeless architecture with exceptional livability, just steps from downtown's quaint lifestyle, multiple parks, weekly farmers market, tennis courts, playgrounds, and resident-only access to the Butler Chain of Lakes. From the moment you arrive, handcrafted timber details, natural stone accents, and inviting front porch creates a sense of warmth rarely found in newer construction. Inside, soaring wood ceilings, exposed pecky cypress beams, custom built-ins, and a dramatic floor-to-ceiling stone fireplace make this house both elegant and welcoming. Designed for everyday living as much as entertaining, the chef's kitchen features premium JennAir appliances, a striking stone cooking alcove, ceiling-height cabinetry, expansive island, generous walk-in pantry, and seamless connection to the dining and family rooms. The flexible floor plan offers six bedrooms and six baths, including two private owner's suites on the main level, making the home ideal for multi-generational living, long-term guests or one of many private spaces. Upstairs, 4 spacious secondary bedrooms and a large over-garage flex room provide endless possibilities as a home fitness studio, media room, hobby space, or home office. Outdoor living is equally impressive with a large covered porch, a wood-burning fireplace, outdoor kitchen, cabana bath, Tiki hut, circular fire pit, designed for year-round enjoyment. The backyard offers ample room to design the custom pool, allowing the next owner to create a backyard tailored to their lifestyle rather than inheriting someone else's design. Additional highlights include a newer roof (2024), commercial grade fire suppression, an oversized three-car garage with exceptional storage and workspace, and the opportunity to add a front gate for enhanced privacy off Main St. Storm hardy with underground electrical utility lines and public water. This is a home has been meticulously maintained and for buyers who appreciate exceptional craftsmanship, enduring quality, and the unique lifestyle that only Historic Windermere offers. Take a short stroll to the Downtown Redevelopment Project and shop at Victoria Jewelers, Ace Hardware, Solvino Wine Bar and Fresco's, one of Dr. Phillips' favorite Italian restaurants, adding even more charm and convenience to this incredible location.

713 Main Street, Windermere

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