Windermere Town Single Family Homes For Rent in Windermere - 3 homes

Remarks: One or more photo(s) has been virtually staged. Available for lease, this refined single-story pool residence is located in the Town of Windermere, just moments from Main Street and the downtown district’s dining, shopping, and community amenities. Positioned on an oversized corner lot beneath mature oak trees, the property offers a private and well-composed setting with thoughtful indoor and outdoor spaces. The residence features four bedrooms, including two primary suites, and three full bathrooms. The kitchen is designed with both style and functionality in mind, offering stainless steel appliances, dual refrigerators, a professional gas range, granite countertops, a subway tile backsplash, and a breakfast bar that connects seamlessly to the main living area. The adjacent living space is highlighted by Saltillo tile flooring, a wood-accented ceiling, expansive windows, and skylights that fill the home with natural light. One primary suite includes an ensuite bathroom with dual vanities, a soaking tub, and a separate shower, along with a spacious walk-in closet and dressing area. Sliding glass doors provide access to a private patio overlooking the pool. Outdoor living is further enhanced by a screened lagoon-style lap pool with a newer heater, paver decking, and multiple patio areas designed for relaxation and entertaining.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Rob Gaudreau (407-579-2737)

Remarks: Welcome to the famed Butler Chain of Lakes waterfront lifestyle! Experience luxury living with small town charm in this Town of Windermere residence boasting breathtaking water views with access to 12 connected lakes. Three of the four bedrooms offer lake views, two with sitting areas and one with access to the patio. You will enjoy the mesmerizing lake vistas from every angle. Step outside into your own paradise, complete with a sparkling pool and a private covered dock to use for easy lake access. Whether you enjoy water skiing, fishing, or simply cruising along the tranquil waters, this property is a water enthusiast's dream come true. This gem also boasts the advantage of a walkable downtown area, allowing you to immerse yourself in the charm of the community. Don't miss the vibrant weekly Friday farmers market, 4th Fridays Food Trucks, coffee shop, hometown diner and local brewery - easily walk or bike from your front door. The town offers ten public parks, three public piers, boat ramps, tennis courts, basketball courts and a library. Luxury living, unmatched natural beauty, and a welcoming small town atmosphere await you in this remarkable home. Don't let this opportunity slip away. Schedule your private showing today and start enjoying the lakefront living lifestyle.

Listing is courtesy of: REVEL REALTY LLC (407-876-6448)

Listing Agent: Rebekkah Boskovich (321-438-3307)

Remarks: One or more photo(s) has been virtually staged. Luxury Lakefront Executive Rental in Downtown Windermere on Lake Bessie. Now offered at a newly adjusted price, this rare 5-bedroom lakefront home presents one of the most compelling rental opportunities in Windermere.Set on Lake Bessie, this renovated residence offers panoramic water views, flexible living spaces, and true indoor-outdoor Florida living, a feature not commonly found in the current rental inventory. Many competing properties offer limited outdoor space or no water access; this home provides a lakefront setting with room to relax and entertain. The open-concept floor plan features a chef’s kitchen with gas range, custom cabinetry, and premium finishes, flowing into spacious living and dining areas. Two first-floor ensuite bedrooms offer ideal flexibility for guests, home office, or multigenerational living. The second-floor primary suite provides a private retreat with elevated lake views. Outdoor features include a screened porch, landscaped yard, fire-pit area, and koi pond, creating a peaceful setting for everyday living or entertaining. Located in Downtown Windermere, this home offers golf-cart-friendly access to local shops, weekly farmers markets, and community events, with convenient proximity to Orlando’s major employment centers, top-rated schools, and world-class attractions including Disney and Universal. Rarely available as a rental, this lakeview property combines location, space, and lifestyle in one of Central Florida’s most sought-after communities. Schedule your private showing today.

Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)

Listing Agent: Karen O'Neil (407-789-5565)