Windermere Homes for Sale in Windermere - 68 homes

Remarks: Fully Renovated Windermere Home. Move-In Ready! Discover 735 Oakdale St, a beautifully updated 3-bedroom, 2.5-bathroom home in the heart of Windermere Town. Over the past four years, no detail has been overlooked: new roof, new gutters, marble flooring, resurfaced pool, new fence and shed, windows, two independent HVAC systems, water filtration system, water heater, well pump, renovated bathrooms, and a striking new façade with marble ledger panel. The backyard features new concrete slabs, perfect for entertaining or relaxing. Inside, the home is filled with natural light thanks to beautiful skylights, creating a warm, inviting atmosphere. Enjoy a functional kitchen, dedicated dining room, living room with cozy fireplace and a den, along with a spacious and versatile bonus room ready to become a music room, home office, playroom, media room, or craft studio, with and additional room for extra storage. The master bedroom is conveniently located downstairs, while the other two spacious bedrooms are upstairs, one featuring a private balcony overlooking the pool and backyard, perfect for morning coffee or morning sunrises. Nestled among sparkling lakes, this home offers a serene, private feel while keeping you close to convenience: just minutes to Restaurant Row, Winter Garden Village, boat ramps, tennis courts, farmers markets, food truck nights, and Orlando’s top theme parks. Enjoy the perfect balance of calm and accessibility in a lively, welcoming community. This isn’t just a house, it’s a place to create memories, pursue a charming lifestyle, and live fully. 735 Oakdale St is ready to welcome you home.

Listing is courtesy of: ALTIS REALTY (407-401-7447)

Listing Agent: Nicoletta Buonaccordo (321-297-8266)

Remarks: Under contract-accepting backup offers. Discover this spacious 2-bedroom, 2.5-bath townhome in the desirable Lake Reams Townhomes community in Windermere. Nestled among beautiful natural surroundings, tree-lined streets, sidewalks, and mature canopied trees, this home offers both comfort and convenience in a charming setting. The thoughtfully designed floor plan features kitchen with granite countertops, 42” cabinets and one year old appliances including the washer and dryer. Both bedrooms are located upstairs, each with its own private full bathroom with updated countertops, mirrors and light fixtures, providing ideal functionality and privacy. A convenient half bath is located on the main level for guests. The home offers abundant storage space throughout and includes one-year-old appliances, including the washer and dryer. Roof was replaced three years ago and for added peace of mind is the responsibility of the HOA along with exterior maintenance and repairs. Enjoy outdoor living with a spacious yard and the rare benefit of a detached two-car garage. Residents also have access to a community pool and beautifully maintained common areas. Ideally located just minutes from the Disney Cast Member entrance and Walt Disney World parks, this property is also close to the scenic Tibet-Butler Nature Preserve. Easy access to all shopping, dining and world-class attractions that Orlando has to offer. Ideal as a primary residence, private vacation retreat, or rental property, this home combines location, lifestyle, and practicality in one exceptional opportunity. Schedule your private showing today.

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: Mae Stigell (631-377-1205)

Remarks: Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction | To Be Built | Designed for Unparalleled Luxury Discover an extraordinary opportunity to own a masterfully designed luxury residence in this Windermere community. This exquisite estate, crafted by the renowned Supreme Construction, offers a perfect blend of sophistication, innovation, and timeless elegance. Property Highlights: • Total Living Area: 3,889 Sq. Ft. | Total Building Area: 5,516 Sq. Ft. • 4 Bedrooms | 4 Full Baths | 1 Powder Room | 1 Pool Bath • Expansive Living Spaces with High Ceilings & Open Floor Plan • Great Room | Dining Room | Gourmet Kitchen with Nook & Pantry • Private Elevator & Multiple Open Decks • 2-Car Garage First-Floor Features: • Grand Foyer with Staircase & High Ceilings • Great Room & Elegant Dining Room • Chef’s Gourmet Kitchen with custom cabinetry, quartz countertops, Subzero appliances, and a spacious island • Guest Suite with Private Bath & Walk-in Closet • Laundry Room & Powder Bath • Pool Bath (Outdoor Access) Second-Floor Features: • Lavish Master Suite with Private Balcony, Spa-Inspired Bath & Custom Walk-in Closet • Two Additional Bedrooms with Walk-in Closets & Shared Designer Bathroom • Two Expansive Open Decks for Outdoor Enjoyment Luxury Amenities & Smart Home Features: • State-of-the-Art Smart Home Integration • Hurricane Impact Windows for Safety & Efficiency • Custom California Closets in All Bedrooms • Heat & Glow Fireplaces in the Living Room & Master Suite • Large Format Porcelain Tile & High-End Finishes Throughout • Flat Tile Roof & Metal Truss Construction for Durability Outdoor Oasis & Entertainment Haven: • Resort-Style Custom Pool & Spa (Separate Permit) • Sunken Outdoor Kitchen & Lounge Area for Elevated Entertaining • Landscaped Backyard with Ample Space for Relaxation & Gatherings Prime Windermere Location – Unmatched Lifestyle & Convenience: • Minutes from Isleworth, Home to Celebrities & Sports Icons • Access to the Pristine Butler Chain of Lakes – Ideal for Boating & Water Sports • A-Rated Schools, Parks, & Year-Round Community Activities • Close to Luxury Shopping, Fine Dining, Golf Courses & Entertainment • Easy Access to Disney, Universal, and Orlando’s Top Attractions This exceptional luxury estate embodies a lifestyle of sophistication, exclusivity, and modern convenience. Secure this once-in-a-lifetime opportunity to own a masterpiece of design and craftsmanship in the heart of Windermere. For more details, floor plans, and customization options, contact us today!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Matthew Hughes (407-619-4717)

Remarks: One or more photo(s) has been virtually staged. Lake View Home with Private Pool & Fireworks Views – Minutes from Walt Disney World Imagine living in a home that perfectly combines comfort, elegance, and practicality in one of the most desirable areas of Windermere. This beautiful residence offers stunning lake views and magical nightly fireworks views from Walt Disney World, creating a truly unique living experience. From the moment you arrive, the well-maintained landscaping and inviting front porch set a warm and welcoming tone. The home features 4 bedrooms and 3 full bathrooms, with a thoughtfully designed open-concept layout that seamlessly connects the living room, kitchen, and dining area. The gourmet kitchen is a true highlight, equipped with stainless steel appliances, custom cabinetry, quartz countertops, a double oven, and a spacious pantry—perfect for those who love cooking and entertaining. Sliding glass doors open to the outdoor space, where a private pool and summer kitchen are currently being completed and will be ready within one month, creating the perfect setting for relaxing or entertaining guests while enjoying the lake view. The primary suite is spacious and comfortable, featuring vinyl flooring, a generous walk-in closet, and a beautifully designed bathroom with dual vanities. The additional bedrooms also feature vinyl flooring, providing both comfort and easy maintenance throughout the home. The two-car garage offers ample space and convenience. Located in the desirable Windermere Isle community, residents enjoy resort-style amenities including a community pool, cabana, playground, and scenic walking trails. The home is also located near top-rated schools, as well as shopping, restaurants, and all the attractions and magic of Walt Disney World just minutes away. If you are looking for quality of life, a prime location, and a beautiful home for your family, this is the perfect opportunity. Schedule your private showing today and come fall in love with this exceptional home.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Jennifer Olmeda (407-547-9242)

Remarks: Welcome to this exquisite and impeccably maintained home filled with natural light and elegant open spaces. As you step inside, you are greeted by a soaring ceiling in the grand foyer that immediately sets the tone for the home’s impressive design. The first floor features a versatile bedroom with a full bath, perfect for guests or multi-generational living, along with a formal dining room that can easily serve as a home office. The beautifully remodeled kitchen is a true showpiece, boasting 42” warm white -colored cabinetry, granite countertops. A walk-in pantry, vented built-in microwave, and two full double ovens provide both convenience and functionality. The spacious island is illuminated with elegant pendant lighting, while a butler’s pantry conveniently located between the kitchen and garage adds extra storage and practicality. The home also features brand-new flooring, adding a fresh and modern touch throughout. The main living areas are finished with neutral tile, while the stairwell and entire second floor—including all bedrooms—showcase new Lifeproof wood-look luxury vinyl flooring. The expansive owner’s suite serves as a private retreat, offering two large walk-in closets, a relaxing soaking tub, separate shower, and dual vanities. Each additional bedroom also includes walk-in closets and TV cable feed-throughs for added convenience. Upstairs you’ll also find a spacious bonus/media room pre-wired for A/V components, perfect for movie nights, gaming, or entertaining. Step outside to your private outdoor oasis, featuring a screened lanai and sparkling saltwater pool with a sun shelf, surrounded by elegant glass mosaic tiles in soothing ocean-blue tones. The property has also been recently enclosed with a newly installed vinyl privacy fence, creating the perfect setting for relaxing afternoons or weekend barbecues. This home is not only beautiful but also energy efficient, featuring R-38 insulation, a 15 SEER HVAC system, and a hybrid water heater, helping keep utility costs low while earning an ENERGY STAR rating. Located in the highly desirable Windermere Trails community, surrounded by scenic green spaces and ponds, and just minutes from shopping, dining, and top attractions. Residents enjoy exceptional amenities including a lakeside pool with splash pad, playgrounds, and a running and biking trail. Don’t miss the opportunity to make this stunning home yours. Schedule your private showing today and experience the lifestyle it offers.

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Andrea Munoz (407-989-2021)

Remarks: Under contract-accepting backup offers. Don’t let the 1962 build date keep you from considering this 4 Bedroom 3 Bath home that received a major renovation to the Electrical, Water Heater & Bath Updates in 2016 * New HVAC 2017 and a New Roof in 2018 made obtaining low cost Tower Hill property insurance easy * in 2025 the luxurious Kitchen was updated with a Thermador Natural Gas Range & top of the line Stainless Appliances with Waterfall Porcelain Tops and all Travertine Stone Backsplash with Marble Inlay Deco Panel – This impressive Craftsman 1 story solid block home offers a very spacious and well laid out floorplan with the Primary Suite overlooking the Pool with a Private Covered Porch – The main house also has a covered porch providing 2 entertaining and BBQ options – The huge 32 x 21 Garage is the perfect setup for family vehicles, golf cart and water toys – The separate 22 x 12 pool cabana provides an inviting space for relaxation and gatherings this ultimate Man Cave or She Shed is limited to your imagination and family’s needs * This very large totally fenced private shaded lot with mature landscaping enjoys the convenience of being within walking distance or just a short golf cart ride to Charming Downtown Windermere, offering Boutique Shopping, Dining, Community Events, Award Winning Schools, Weekly Farmers Market & the Monthly Food Truck Friday Night * No HOA or dues * Oversized windows bring in Natural Light and views to the Landscaped Yard * A Public Dock and Beach on Lake Down are a short walk away, offering opportunities for Fishing, Picnics, Sunset Views, and Water Activities on the Lake Butler Chain of Lakes - a defining feature of Windermere living * With close proximity to Winter Garden Village, Restaurant Row, and all of the Area Attractions you are truly in the Heart of it All.

Listing is courtesy of: VINTAGE REALTY GROUP LLC (407-217-5458)

Listing Agent: Darrell Nunnelley (407-467-8069)

Remarks: LOCATION, LOCATION, LOCATION! Welcome to this stunning bungalow-style single-family home located in the highly sought-after Windermere Trails community—where lifestyle, convenience, and charm meet at your front door. Built by Meritage Homes (consistently ranked among the best builders in Florida), this residence features the desirable Angelou floor plan offering 3 bedrooms, 2.5 bathrooms, a spacious loft, and 1,876 square feet of thoughtfully designed living space. The open-concept kitchen and living area create a warm, inviting flow—perfect for everyday living and entertaining. Upstairs, you’ll find a versatile loft, a spacious primary suite, and two additional bedrooms with a full bathroom conveniently located between them. Wood flooring throughout the main living areas and a wooden staircase. Step outside and enjoy Florida living at its finest. From the large front porch, take in breathtaking sunsets and the Magic Kingdom nightly fireworks, while the extra-wide private balcony offers peaceful sunrise views. The rear-entry 2-car attached garage and low-maintenance yard provide both functionality and ease of ownership. *** Owned solar panel system (paid in full—no lease) designed to offset most or all of your monthly electric bill.*** The location is truly unbeatable. The home is walking distance to Bay Lake Elementary, as well as top-rated daycare and middle schools—offering unmatched peace of mind for families. Everyday conveniences such as grocery stores, dining, gyms, and shopping are also just steps away, including the newly opened Lakeside Village shopping plaza. Windermere Trails residents enjoy resort-style amenities including a large community pool, playground, dog park, scenic lakes and preserves, and miles of biking and jogging trails surrounded by beautiful retention ponds and local wildlife—perfect for morning walks and outdoor living.

Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)

Listing Agent: Renan Serretiello (407-415-7317)

Remarks: Under contract-accepting backup offers. Don't miss an Opportunity to own this Great Craftsman Home overlooking a serene Wooded View, located in the community of Lakes of Windermere. Impeccably maintained and Move-in ready, this 4-bedroom, 2.5-bath home offers numerous Upgrades and Touches throughout. Such as all new kitchen appliances, newly painted interior, new A/C, Hardwood flooring, Water Softener, Built-Ins, and Newer Roof. Three stylish transom windows located in the Living Room allow lots of Natural Light. Granite counters and solid wood cabinetry in the kitchen. Butler's pantry off the Dining Room. A relaxing spa is located on the screened-in Lanai with custom pavers. This home has paid attention to detail, finish, form, and function. The Lakes of Windermere community is known for promoting a well-maintained, safe, and family-friendly environment with many acres of natural beauty amidst great live oaks, pine trees, and beautiful natural habitats. The oak tree-lined community and combination of outdoor amenities rival the best of Orlando’s communities. Our neighborhood features include: A picturesque pier located on Lake Sawyer is perfect for fishing, relaxing, or nightly star gazing. This community features a large pool and sun deck perfect for those hot summer days. There is also a kitchen available for use by reservation. Tennis. Volleyball. Basketball. Gazebo. 3 Playgrounds. Whatever your favorite activity is, the Lakes of Windermere will have a place for you to enjoy the beautiful sunshine of Central Florida. (Room measurements are approximate, Buyer to verify) Home Warranty to be provided by Seller.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Sean Flatley (609-208-8204)