Windermere Homes for Sale

Windermere Homes for Sale

Located in Orange County, Florida, Windermere is a charming town known for its picturesque landscapes and luxurious homes. Nestled amidst the beautiful Butler Chain of Lakes, this affluent suburb is a popular choice for those seeking an upscale and tranquil living environment.

Windermere offers a wide range of homes for sale, catering to different preferences and budgets. Whether you're in search of a spacious single-family home, a stylish townhouse, or a luxurious estate, you'll find a variety of options to choose from. The real estate market in Windermere is known for its high-end properties, featuring stunning architectural designs, modern amenities, and expansive outdoor spaces.

Living in Windermere offers residents a host of benefits. The town boasts excellent schools, making it an ideal location for families. The community is also known for its strong sense of community spirit, with various events and activities organized throughout the year. Windermere's proximity to Orlando's world-class entertainment and attractions adds to its appeal, allowing residents to enjoy the best of both worlds.

If you're looking for a place that combines natural beauty, upscale living, and a welcoming community, Windermere is the perfect choice. With its stunning homes for sale and idyllic surroundings, this city offers a lifestyle that is both luxurious and serene.

Newest Windermere Homes for Sale

14551 Yellow Butterfly Road, Windermere
$784,900
5 Beds ⋅ 4 Baths ⋅ Stillwater Xings Prcl Sc-13 1 SubDv. ⋅ 34786 Zip Code
Welcome to this beautifully maintained and thoughtfully updated home, ideally situated along a quiet bend of Yellow Butterfly Road in the desirable Summerport community. Backing to a peaceful natural setting with trees, a scenic walking path, and pond views, this property combines privacy, comfort, and convenience. Step outside and enjoy the fenced backyard, attractive landscaping, young orange and mango trees, and an expansive brick-paver patio—an inviting setting for relaxing, entertaining, or simply enjoying Florida's beautiful weather. Inside, the home features spacious living areas, including a versatile first-floor den that can serve as a home office, study, or flex space. Imagine coming home for the holidays, gathering with loved ones, and enjoying the warm glow of the fireplace at the flick of a switch—a cozy touch that makes this home especially inviting. The attached three-car tandem garage offers generous parking capacity and additional flexibility for storage. Upstairs, five generously sized bedrooms are thoughtfully arranged for comfort and privacy. The expansive primary suite features two walk-in closets, while two additional bedrooms share a Jack-and-Jill bathroom with separate vanities. Another bedroom features its own en-suite bathroom, and the oversized fifth bedroom, overlooking the trees and pond, provides endless possibilities as a playroom, game room, or additional living space. Conveniently located near SR 535, Hamlin's shopping and dining destinations, scenic walking trails, and Summerport's community amenities, this home provides easy access to the area's finest shopping, dining, recreation, and everyday conveniences. Keene's Crossing Elementary School is within easy reach via the walking path behind the home. Bridgewater Middle School, Windermere High School, Windermere Preparatory School, Foundation Academy, and other educational options are also nearby. Lovingly cared for by its owners, this home is being presented for sale due to a family relocation out of state. A wonderful opportunity to make this exceptional Summerport property your own! Seller is open to considering flexible buyer credits toward closing costs or a mortgage rate buydown for purchase proposals at or near the asking price.

14551 Yellow Butterfly Road, Windermere
104 E 11th Avenue, Windermere
$862,500
3 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Photos coming soon! Welcome to your new home in the historic, golf-cart-friendly Town of Windermere! Nestled on a 0.29-acre corner lot shaded by mature trees, this charming 1-story block home offers 3 bedrooms, 2 bathrooms, and 1,834 square feet of flexible living space on one of Windermere’s beloved dirt roads. Step inside to find an open-concept floor plan designed for effortless entertaining. The oversized main living room serves as a blank canvas, highlighted by a cozy fireplace that anchors the gathering area. Transition seamlessly into the expansive kitchen—a chef’s dream packed with extensive prep space. The hallway in the center of the house leads to the bedrooms and a full guest bathroom, while the rear primary suite serves as a quiet retreat complete with an en-suite bathroom. The entire home is fully wired for AT&T high-speed fiber internet, making remote work a breeze. Your private oasis awaits outside. Enjoy a dedicated 36’ x 40' sports court equipped with a basketball hoop, ping pong table, and pickleball net — the ultimate setup for weekend matches and entertaining. Afterward, unwind on your screened back porch. Experience additional peace of mind with an extensive list of structural and mechanical updates: Water Treatment & Softener System (08/2026, incl. transferable warranty) Well Pump (07/2024) Exterior Paint (01/2023) New Attic Insulation (2023) Electric Water Heater (03/2022) New Electric Panel ( 03/2023) Metal Roof (11/2017) HVAC System (06/2014) Double Pane Windows (2012) ?Living in the heart of Windermere means you are just a short walk or golf-cart ride from boutique shopping, weekly farmers markets, and local dining. Best of all, residents enjoy exclusive access to private neighbourhood boat ramps to launch into the pristine Butler Chain of Lakes, as well as nearby tennis courts and waterfront parks. Zoned for top-rated public schools including Windermere Elementary. ?Don't miss this rare opportunity to live the ultimate lake-community lifestyle! Seller offers up to 2% buyer credit or towards rate buy-down!!!

104 E 11th Avenue, Windermere
8736 Peachtree Park Court, Windermere
$875,000
4 Beds ⋅ 3 Baths ⋅ Peachtree Park SubDv. ⋅ 34786 Zip Code
Welcome to this beautifully updated home in the desirable Windermere area, just minutes from Walt Disney World! Featuring a convenient downstairs bedroom and full bathroom. The main living area showcases a stunning custom fireplace, while the kitchen features high-end Café appliances, including an induction range, and a custom pantry. Additional upgrades include all new hurricane-impact windows, automatic shades throughout, a water softener, and fresh interior and exterior paint. Upstairs, you'll find the spacious primary suite with a custom California Closet, 2 additional bedrooms, a loft with a custom glass half wall. The garage features epoxy flooring and EV charging. Enjoy a fenced backyard with no rear neighbors and beautiful natural surroundings, plus a neighborhood playground. Conveniently located near Disney, shopping, dining, and major roadways, this home offers an incredible combination of upgrades, comfort, and location!

8736 Peachtree Park Court, Windermere
9100 Palm Tree Drive, Windermere
$579,000
3 Beds ⋅ 2 Baths ⋅ Silver Woods Ph 01 SubDv. ⋅ 34786 Zip Code
Welcome to this inviting 3-bedroom, 2-bathroom pool home, situated on a corner lot with a circular driveway in the established community of Silver Woods. A spacious foyer opens into the living room, flowing seamlessly into the adjoining dining area for easy everyday living and entertaining. The conveniently located kitchen connects to the family room, where wood-look tile and vaulted ceilings create a warm, open gathering space. The split-bedroom floor plan offers privacy for the primary suite, complete with a walk-in closet and attached bathroom. Two additional bedrooms and a full bathroom are located on the opposite side of the home, providing flexibility for guests, a home office, or everyday needs. French doors from the family room open to the patio and in-ground pool, creating a welcoming setting for outdoor dining, weekend gatherings, or simply relaxing in the Florida sunshine. A fenced backyard completes the outdoor space. Recent updates - New Porcelain Tile floor throughout, New Hurricane strength garage door, New cabinetry in garage and laundry room, Custom closets in Primary, Roof 2021, Windows 2020, HVAC 2019. Silver Woods offers low HOA fees and community tennis courts, along with a convenient Windermere location near shopping, dining, and Dr. Phillips’ Restaurant Row. Enjoy access to major roadways and popular Central Florida destinations, including Universal Orlando Resort and Walt Disney World. This home brings together comfortable living, outdoor enjoyment, and everyday convenience!

9100 Palm Tree Drive, Windermere
10628 Reams Road, Windermere
$479,000
4 Beds ⋅ 3 Baths ⋅ Windermere Trls Ph 1c SubDv. ⋅ 34786 Zip Code
Welcome to Windermere Trails! This beautiful 4-bedroom, 2.5-bath, two-story home offers the perfect combination of comfort, style, and convenience in one of Central Florida's most desirable locations. Step inside to discover a spacious, open-concept floor plan designed for both everyday living and entertaining. The kitchen features granite countertops, stainless steel appliances, ample cabinetry, and a seamless flow into the living and dining areas. Wood flooring enhances the main living spaces, while generously sized bedrooms provide plenty of room to unwind. Enjoy the convenience of an attached two-car garage, interior laundry, and a private outdoor patio perfect for relaxing after a long day. Ideally located just minutes from Walt Disney World, Disney Springs, shopping, dining, and entertainment, with convenient access to major roadways and everything the growing Horizon West area has to offer. This home delivers the space, location, and lifestyle you've been looking for. Schedule your private showing today!

10628 Reams Road, Windermere
8205 Stonemason Court, Windermere
$2,650,000
6 Beds ⋅ 6 Baths ⋅ Keenes Pointe Unit 3 SubDv. ⋅ 34786 Zip Code
Distinctive craftsmanship, open-concept interiors and expansive outdoor living distinguish this custom six-bedroom, six-full-bath residence in Keene’s Pointe. Built in 2016 on a nearly ½-acre homesite, the residence unfolds around a spacious great room appointed with custom dining and entertainment cabinetry. The main level encompasses the primary retreat, a guest bedroom with an ensuite bath, a full pool bath, an office, a kitchen, a generous breakfast nook and a walk-in pantry. Upstairs, three bedrooms with ensuite baths accompany a sixth bedroom suited to use as a studio, playroom or flexible living space, along with a spacious loft featuring a hospitality bar. A mini elevator provides a practical way to transport items between floors, simplifying housekeeping. Custom millwork lends continuity throughout the interiors, from integrated bedroom desks and storage drawers to the great-room entertainment center and a full-wall display case in the study/office. Thoughtfully designed dining cabinetry accommodates table linens, dinnerware, silverware and décor, complemented by a substantial custom china cabinet for glassware near the corner wine room. An integrated buffet offers an elegant setting for serving or displaying fresh flowers and collectibles. Solid-wood interior doors and elaborate custom cabinetry in every closet and the oversized walk-in pantry carry this attention to detail throughout the home. Double-pane windows and sliding doors complement a modern, outward-swinging steel double entry door edged in wood. Additional appointments include upgraded Monogram stainless steel kitchen appliances, whole-house water purification and softening, tankless natural gas water heaters, Lutron lighting controls in the main living areas and a dedicated irrigation well. The generous covered outdoor living area extends the entertaining experience with a complete summer kitchen, including a dishwasher, dinnerware storage, a gas grill and a double-burner cooktop integrated into an oversized island. Positioned beside an oversized conversation pit, the island anchors a lounge-like setting for outdoor gatherings. The private backyard brings together a pool, spa and expansive paver deck in an inviting setting for outdoor entertaining. Just steps from the primary retreat, the spa offers a convenient escape, while an illuminated firepit gathering area provides another setting for evenings outdoors. A mini half-court basketball practice area introduces a recreational dimension, balancing spaces for relaxation, gathering and activity. Located in the highly sought after guard gated lakefront and golf course community of Keene’s Pointe and home of the Golden Bear Club, a private golf and tennis club, residents enjoy a host of amenities including a community boat ramp and a range of parks and playgrounds. Come live the Keene’s Pointe lifestyle!

8205 Stonemason Court, Windermere
6620 Sawyer Shores Lane, Windermere
$930,000
4 Beds ⋅ 4 Baths ⋅ Sawyer Shores Sub SubDv. ⋅ 34786 Zip Code
Welcome to a rare opportunity to enjoy waterfront living in Windermere! Enjoy canal-front living with access to Lake Sawyer and Little Lake Sawyer from this 4 bedrooms, 3.5 bath Windermere home on over half an acre. Mature trees and a wooded waterway create an inviting backdrop for this home's updated interiors and flexible layout. Inside, welcoming details include crown, decorative wall treatments, and built-in living room shelving. The updated kitchen features white cabinetry, stone countertops, a patterned tile backsplash, under cabinet lighting, stainless steel appliances, and a double-oven range. A generous dining room provides plenty of space for gatherings. Two owner's suites - one upstairs and one downstairs - offer flexibility for guests or multi-generational living. Updated bathrooms feature distinctive tilework and double-sink vanities. Upstairs, a spacious air-conditioned sunroom overlooking the backyard adds versatile living space for relaxing, hobbies, or a home gym. French doors connect the living and dining areas to the downstairs screened porch, while a covered patio provides another spot for outdoor entertaining. The spacious fenced backyard features a swim spa with an adjoining deck, plus a private dock and boat ramp for enjoying the lakes. Major updates include a roof replacement and exterior paint in 2020, upstairs AC and water heater in 2023, an irrigation system installation and asphalt driveway expansion in 2024, a renovated primary shower in 2025, and downstairs AC in 2026. An attached garage completes this property.

6620 Sawyer Shores Lane, Windermere
3165 Butler Bay Drive N, Windermere
$3,995,000
7 Beds ⋅ 8 Baths ⋅ Butler Bay SubDv. ⋅ 34786 Zip Code
Set behind the gates of Windermere Club, this extraordinary lakefront estate presents a rare opportunity to experience refined luxury on the shores of Lake Crescent. Situated on a pristine one-acre homesite, this custom-built residence was thoughtfully crafted in 2015 to blend contemporary sophistication with timeless architectural elegance. Fresh exterior and interior paint enhance the home's striking architectural presence and timeless appeal. Encompassing nearly 9,000 square feet of impeccably designed living space, the home features seven bedrooms, seven full baths and one half bath, offering an exceptional balance of grandeur and comfort. Soaring 12-foot ceilings on the main level, 10-foot ceilings upstairs and elegant eight-foot doors enhance the home's impressive architectural scale. Expansive windows and doors frame breathtaking panoramic lake views, flooding the interiors with natural light and creating a seamless connection between indoor and outdoor living. The dramatic great room showcases polished travertine flooring, designer lighting fixtures and stunning vistas at every turn. Designed to inspire culinary excellence, the gourmet kitchen is appointed with professional-grade appliances, a handcrafted wine display, an oversized granite island and an expansive walk-in pantry. Adjacent gathering spaces include an elegant dining room and a welcoming family room. Outdoor living is equally impressive, featuring a resort-style heated swimming pool with a new pool pump, a fully equipped summer kitchen and expansive entertaining areas overlooking the water. An automated mosquito misting system enhances year-round enjoyment of the outdoor spaces. The residence offers first-floor and second-floor primary suites, four additional en-suite guest bedrooms, a private office, a theater room, a sophisticated bar and spacious balconies that capture spectacular sunrise views across the lake. The luxurious primary bath offers a steam room in the shower, creating a spa-inspired retreat within the comfort of home. Thoughtfully equipped with modern efficiencies, the property includes a 25-kW solar energy system with bidirectional metering, two 80-gallon solar-assisted water heaters, a whole-home water purification system, four HVAC systems, a recently installed septic drain field, an underground propane tank and a three-car garage. A private dock provides direct access to Lake Crescent, completing this exceptional waterfront lifestyle. Spanning approximately 187 acres, spring-fed Lake Crescent offers an exceptional setting for boating, waterskiing, fishing and watersports. Unlike the busier Butler Chain of Lakes, Lake Crescent provides a more intimate waterfront experience, combining recreational freedom with the tranquility and privacy of an exclusive lakefront retreat. Ideally situated within reach of Windermere and Winter Garden's premier shopping, dining and recreational destinations, this remarkable estate embodies the very finest in Central Florida lakefront real estate.

3165 Butler Bay Drive N, Windermere
5509 Marleon Drive, Windermere
$3,350,000
5 Beds ⋅ 6 Baths ⋅ Lake Davis Reserve SubDv. ⋅ 34786 Zip Code
Timeless elegance and distinctive lakefront luxury unite in perfect harmony in this custom-built waterfront masterpiece. Designed to capture the beauty of its stunning setting, the inviting living room welcomes with rich terracotta tile flooring, custom tray ceilings accented with exposed wood beams, an adjacent dining room, and a stunning fireplace, creating an elegant and sophisticated gathering space. Expansive sliding glass doors frame breathtaking lake views and seamlessly connect the interior to the outdoor living area, pool, cabana with summer kitchen, and waterfront beyond. Thoughtfully designed for both grand entertaining and everyday living, the main living areas offer an effortless transition between formal spaces and the casual dining area, chef's kitchen, and expansive family room, all framed by dramatic sliding pocket doors that invite panoramic water views indoors. Kitchen highlights include stainless steel GE Monogram appliances, a gas cooktop, custom tile backsplash, and a stunning hand-hammered copper farmhouse sink that serves as both a functional centerpiece and a striking design statement. The spacious primary suite is a private retreat featuring soaring ceilings, abundant natural light, a cozy sitting area, a flex space ideal for a second office or nursery, and direct access to the outdoor living areas for the perfect blend of luxury and lakefront tranquility. The primary bath features dual vanities, a jetted soaking tub, and a dramatic walk-in shower with natural stone finishes, arched wrought-iron windows, and multiple body sprays to create an exceptional spa-like retreat. An executive office and full pool bath are conveniently located just outside the primary suite. A first-floor guest suite provides a welcoming retreat for visitors. Upstairs, three generously sized ensuite bedrooms accompany a large secondary family room with sliding glass doors that open to a private balcony overlooking the estate grounds and waterfront. Outside, a private resort oasis awaits, featuring a saltwater pool with a sun shelf, deck jets, and a sheer-descent waterfall - along with a spa, expansive travertine pool decking, retractable screens, outdoor dining spaces, and a fully equipped summer kitchen. A separate cabana elevates the outdoor experience with a grill, hibachi grill, two beverage refrigerators, bar seating, and storage rooms. The private dock is boat-ready with an electric lift, while two floating jet ski docks ensure effortless access to water toys. Gated neighborhood with just 18 home sites and walking distance to Windermere Prep.

5509 Marleon Drive, Windermere
2925 Butler Bay Drive N, Windermere
$2,200,000
5 Beds ⋅ 5 Baths ⋅ Butler Bay SubDv. ⋅ 34786 Zip Code
Virtually Staged. LUXURY LAKEFRONT ESTATE | 0.64-ACRE LOT | PRIVATE DOCK | PRIVATE POOL | OUTDOOR SUMMER KITCHEN | 3-CAR GARAGE Experience luxury living at its finest in this stunning contemporary lakefront estate, set on an impressive 0.64-acre lot. Featuring two levels of thoughtfully designed living space, this exceptional residence combines elegant architecture, upscale finishes, and breathtaking panoramic lake views. Upon entering through the beautiful solid wood double doors, you are welcomed by an impressive formal living room and a spacious formal dining area. Large panoramic windows frame the spectacular lake views, bringing natural light into the home and creating a seamless connection with the surrounding landscape. A beautifully appointed private office provides the perfect setting for working from home. The gourmet kitchen is truly a chef's dream, featuring high-quality custom cabinetry, quartz countertops, an oversized island, a spacious pantry, and generous workspace. Designed for both everyday living and entertaining, the kitchen flows effortlessly into the inviting family room, complete with custom built-in shelving and a gas fireplace. The luxurious primary suite is a private retreat, featuring elegant wood flooring, separate walk-in closets, and magnificent views of the pool and lake. The spa-inspired primary bathroom offers a large soaking tub and an expansive walk-in shower with dual showerheads. The lower level features three generously sized bedrooms, including one private en-suite bedroom. The remaining two bedrooms share a beautifully designed Jack-and-Jill bathroom, providing comfort and functionality for family members and guests. Additional interior highlights include a fully equipped laundry room with custom cabinetry and a convenient half bathroom with direct access to the pool area. The three-car side-entry garage features built-in storage cabinets, an electric vehicle charging station, and durable epoxy flooring. Step outside and discover your own private paradise! The covered lanai overlooks the beautiful pool and surrounding lake views, creating the perfect setting for relaxation and entertaining. The fully equipped outdoor summer kitchen features a sink, refrigerator, and built-in grill, making outdoor dining and entertaining effortless. Adding to this exceptional property is a private covered dock, offering a unique opportunity to enjoy the waterfront lifestyle. This remarkable lakefront estate brings together space, privacy, luxury, and spectacular views in one extraordinary property. A rare opportunity to own a truly exceptional home where every detail has been thoughtfully designed to elevate everyday living. SCHEDULE YOUR PRIVATE SHOWING TODAY AND EXPERIENCE THIS EXTRAORDINARY LAKEFRONT LIFESTYLE!

2925 Butler Bay Drive N, Windermere
13555 Gorgona Isle Drive, Windermere
$899,000
6 Beds ⋅ 4 Baths ⋅ Windermere Isle SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to Windermere Isle, where spacious living, thoughtful design, and an exceptional location come together in this impressive 6-bedroom, 4-bathroom home offering 4,199 square feet of living space, plus a spacious upstairs loft! Designed with both everyday comfort and entertaining in mind, this beautiful two-story residence features an open and versatile floor plan with two bedrooms conveniently located on the first floor. Beautiful wood flooring leads to the second floor, while wood-look tile flooring flows throughout the main living areas, creating a warm and cohesive feel. An abundance of windows fills the home with natural light. The spacious family room opens seamlessly to the beautifully appointed kitchen, featuring quartz countertops, rich dark cabinetry, stainless steel appliances, a gas cooktop, built-in double ovens, a stylish tile backsplash, and an oversized center island with seating, perfect for casual meals and gathering with friends and family. A generous dining area provides additional space for everyday meals, while a separate formal dining room offers an inviting setting for special occasions. Additional highlights include an expansive walk-in pantry and a conveniently located built-in workspace with abundant cabinetry and countertop space. The first floor also offers two bedrooms, providing flexibility for guests, a home office, or multigenerational living. Upstairs, the spacious loft creates an impressive second living area, ideal for a media room, game room, or comfortable gathering space. Four additional bedrooms provide plenty of room for everyone, and quartz countertops in all bathrooms add a cohesive finishing touch. Step outside through the sliding glass doors to a generously sized covered patio overlooking the fenced backyard, offering a wonderful setting for outdoor dining, entertaining, or simply enjoying the Florida weather. As an added bonus, enjoy views of Disney fireworks from your own backyard! Additional features include a two-car garage with overhead storage racks, two air-conditioning systems, and solar panels that will be paid off by the seller at closing, providing an appealing energy-efficient benefit. Residents of Windermere Isle enjoy a resort-style community swimming pool with poolside cabana and playground, while HOA fees include lawn care, cable TV, and internet. Conveniently located near Walt Disney World, world-class shopping, dining, and major roadways. With its generous living spaces, versatile floor plan, and desirable community amenities, this exceptional home offers an outstanding opportunity to enjoy the Windermere lifestyle!

13555 Gorgona Isle Drive, Windermere
11545 Brickyard Pond Lane, Windermere
$2,200,000
8 Beds ⋅ 9 Baths ⋅ Lake Burden South Ph I SubDv. ⋅ 34786 Zip Code
Experience Lakefront Luxury in the Heart of Windermere! Nestled on a peaceful cul-de-sac in the desirable Lake Burden South community, this stunning two-story residence offers an exceptional blend of elegance, privacy, and Florida living. Situated on an expansive 0.75-acre lakefront lot, the home features 8 spacious bedrooms, 8 full bathrooms, 1 half bathroom, and a thoughtfully designed layout filled with natural light and beautiful waterfront views. Step inside to discover soaring ceilings, elegant finishes, and inviting living spaces. The gourmet kitchen features quartz countertops, stainless steel appliances, generous cabinetry, and a spacious center island, perfect for everyday living and entertaining. Two primary suites provide added comfort and flexibility. The true highlight awaits outdoors, where a private pool, fully equipped summer kitchen, and expansive entertaining areas create your own lakefront retreat. Enjoy breathtaking water views and unforgettable Florida sunsets from the upstairs balcony. Additional features include a three-car garage and solar energy system. Residents of Lake Burden South enjoy access to community amenities, including a swimming pool, tennis courts, playgrounds, and scenic walking paths. Ideally located in sought-after Windermere, just minutes from excellent shopping, dining, and Walt Disney World, this remarkable property offers the perfect balance of peaceful lakefront living and everyday convenience.

11545 Brickyard Pond Lane, Windermere
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