Windermere Real Estate

Welcome to Windermere, Florida—a picturesque and vibrant subdivision nestled in the heart of Orange County. Known for its stunning lakes, lush landscapes, and charming small-town atmosphere, Windermere offers a unique blend of tranquility and community spirit that makes it one of Central Florida's most sought-after locales.

As you stroll through the tree-lined streets, you’ll discover a delightful mix of contemporary and traditional homes, each with its own character and charm. Windermere is renowned for its family-friendly environment, featuring top-rated schools, beautiful parks, and an array of recreational activities that cater to residents of all ages. Whether you enjoy boating on the pristine lakes or exploring the scenic trails, there’s no shortage of outdoor adventures to be had.

In addition to its natural beauty, Windermere boasts a vibrant local culture with quaint boutiques, gourmet restaurants, and lively community events. The annual Windermere Art Festival and Farmers Market are just a couple of the highlights that bring residents together, fostering a strong sense of belonging and camaraderie.

Conveniently located just a short drive from Orlando, Windermere offers easy access to world-class attractions, shopping, and dining, all while maintaining its serene, suburban charm. If you’re looking for a place that combines luxury living with a close-knit community, look no further than Windermere. Discover your dream home in this enchanting subdivision and experience the best that Florida has to offer!

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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