Windermere Homes for Sale

Windermere Homes for Sale

Welcome to Windermere, Florida – a picturesque gem nestled in Orange County that perfectly blends small-town charm with modern conveniences. Known for its stunning lakes, lush landscapes, and welcoming community, Windermere is a sought-after destination for families, retirees, and anyone looking to embrace the Florida lifestyle.

Windermere is renowned for its beautiful homes and serene surroundings. The real estate market here offers a diverse range of properties, from luxurious waterfront estates to cozy single-family homes. As you explore the homes for sale, you’ll discover a variety of architectural styles, including Mediterranean, contemporary, and traditional designs, all set against the backdrop of Florida’s natural beauty.

One of the highlights of living in Windermere is its close-knit community atmosphere. The town is home to several parks, recreational areas, and scenic walking trails, making it easy to enjoy the great outdoors. The charming downtown area features quaint shops, delightful eateries, and vibrant local events that foster a sense of belonging among residents.

Windermere’s prime location also provides easy access to the bustling attractions of Orlando, including world-famous theme parks, shopping destinations, and cultural venues, all just a short drive away. With top-rated schools and a family-friendly environment, Windermere is not just a place to live; it’s a place to thrive.

If you’re searching for your dream home in a tranquil yet vibrant community, look no further than Windermere, where you’ll find the perfect blend of comfort, beauty, and opportunity. Explore our listings today and take the first step toward making Windermere your new home!

Newest Windermere Homes for Sale

11103 Bridge House Road, Windermere
$6,750,000
5 Beds ⋅ 8 Baths ⋅ Reserve At Lake Butler Sound 45/120 SubDv. ⋅ 34786 Zip Code
Elegance defines this lakefront estate perched along the shores of Lake Butler, set behind the guarded-gates of the coveted Reserve at Lake Butler Sound—one of Windermere’s signature communities. This commanding residence offers 5 bedrooms, including 4 in the main house and a private guest-house suite that also features a show-stopping movie theatre and a downstairs entertainment room complete with bar and stage. A dramatic foyer introduces the formal living room, where soaring arched windows frame serene lakefront views beyond the resort-style pool and tropical surroundings. The upscale ambiance is elevated by a floor-to-ceiling custom stone fireplace, classic columns, tile flooring, and a seamless flow into the polished formal dining room, enhanced by an air-conditioned, glass-enclosed wine wall. The chef’s kitchen showcases rich wood cabinetry, a marble-topped island with seating, and ornate pendant lighting. Dark stone countertops, a custom tile backsplash, Wolf appliances, gas cooktop, Sub-Zero refrigerator, and built-in vegetable steamer create a refined and highly functional workspace, all enriched by natural light and warm architectural details. The breakfast area and spacious family room open to the outdoor living spaces through fully retractable L-shaped doors. The primary suite features new carpeting, a sitting area, French doors to the pool patio, and a luxurious bath with soaking tub, generous walk-in shower with triple showerheads, and a spiral staircase leading to a flex space transformed into an oversized closet. Also on the main level are an office, half bath, laundry room, and mudroom. A dramatic staircase leads to the second-floor family room and three additional bedroom suites. Outdoor living includes a covered family room with fireplace, tranquil koi pond surrounded by lush landscaping, tiled pool decking, heated saltwater pool and spa, and a covered boat dock on Lake Butler. Additional features include Savant whole-home music, a Generac generator powering 75% of the home, and distinguished neighborhood with roving security, community park, fishing pier, and back gate access to SR 535 and Windermere Prep. Home furnishings available separately.

11103 Bridge House Road, Windermere
105 Forest Street, Windermere
$2,700,000
5 Beds ⋅ 6 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Virtually Staged. Pre-Construction. To be built. Experience bespoke living without the guesswork. Perfectly positioned on an expansive ~0.38-acre corner homesite in the heart of historic downtown Windermere, this pre-construction luxury estate offers a fully curated, turnkey vision where every architectural nuance and designer finish has already been expertly selected. Spanning 4,430 heated square feet (5,961 total under roof), this two-story transitional masterpiece balances warm natural textures with crisp, modern lines. The striking exterior pairs smooth stucco, organic stone cladding, bronze-framed windows, and a generous three-car garage. Inside, a two-story foyer and engineered hardwood floors lead to an expansive gathering room anchored by wood-wrapped ceiling beams, a paneled feature wall, and a gas fireplace set into a custom plaster surround. Culinary enthusiasts will fall in love with the chef’s kitchen, detailed with semi-custom cabinetry, light oak accents, reeded woodwork, solid stone surfaces, a substantial statement island, a custom plaster range hood, and a hidden walk-in pantry. The main level also hosts the owner’s retreat—a restful sanctuary complete with exposed ceiling beams, a morning beverage bar, an oversized custom closet, and a spa-grade bath equipped with a freestanding soaking tub, dual stone vanities, and a walk-in shower. Every square foot is thoughtfully calibrated for versatile modern living and entertaining. The main level balances productivity and wellness with a private executive study and a dedicated home fitness room, while an expansive second-story loft and media/flex theater provide effortless spaces for relaxation and hosting. Daily convenience is elevated through bespoke utility spaces, including a custom mudroom, an oversized laundry suite, and a dedicated pet spa complete with a built-in wash station. Outside, the living space expands onto an all-season covered lanai finished with rich wood ceiling details, natural stone accents, a full summer kitchen, and dedicated lounge and dining zones designed for year-round entertaining. Enjoy Windermere’s quintessential golf cart lifestyle: ride to weekly farmers' markets, stroll canopy-lined streets along the lakes, and take advantage of deeded Butler Chain of Lakes access, local tennis courts, golf clubs, top-tier schools, and world-class dining.

105 Forest Street, Windermere
11209 Macaw Court, Windermere
$2,695,000
5 Beds ⋅ 7 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
An extraordinary expression of craftsmanship and architectural distinction, this custom Unnerstall residence was originally conceived as the builder's personal home, where exceptional attention to detail and thoughtful design are evident throughout. Beautifully positioned along the 4th hole of the Golden Bear Club's Jack Nicklaus Signature Golf Course, the estate captures sweeping fairway and tranquil water views within the guard-gated community of Keene's Pointe. Spanning 6,105 square feet of air-conditioned living space, the thoughtfully designed floor plan offers 5 bedrooms, 6 full bathrooms, 1 half bath, and an impressive collection of spaces tailored to today's luxury lifestyle. Soaring ceilings, elegant travertine flooring, exquisite Venetian plaster finishes, and distinctive architectural details create an atmosphere of timeless sophistication, while expansive windows invite natural light and showcase the picturesque surroundings. At the heart of the home, a beautifully appointed gourmet kitchen features rich custom cabinetry, stone countertops, professional-style appliances, and an expansive center island. Opening to a dramatic two-story family room, this inviting space creates a seamless flow for everything from intimate gatherings to grand-scale entertaining. Two dedicated offices, including a richly appointed executive study with custom built-ins and a fireplace, has exceptional flexibility, while a private fitness room and sun-filled bonus/game room provide additional spaces for recreation and relaxation. The expansive main-level primary suite is a sanctuary of comfort and elegance, featuring generous dual walk-in closets and a remarkable spa-inspired bathroom with a soaring two-story ceiling, architectural detailing, dual vanities, and a luxurious soaking tub. A second main-floor bedroom suite offers an ideal retreat for extended-stay guests, while three additional en-suite bedrooms provide beautifully appointed accommodations and privacy throughout the upper level. Beyond the interiors, the home's outdoor living spaces rival those of a private resort. An expansive covered lanai with automated retractable screens transitions effortlessly to a sparkling pool and spa, surrounded by lush, mature landscaping that creates a sense of seclusion while preserving the stunning golf course views. A distinctive copper-roofed gazebo, complete with a summer kitchen and bar, provides an unforgettable setting for alfresco dining, entertaining, and enjoying Florida's beautiful year-round climate. Additional appointments include an expansive paver driveway, a three-car garage with a dedicated golf cart entrance, and an array of custom finishes that reflect the home's exceptional quality and craftsmanship. Set amid the natural beauty of Keene's Pointe, with its winding streets, mature trees, and picturesque golf and water views, this remarkable residence offers an exceptional combination of architectural character, versatile living spaces, and the effortless elegance of the Windermere lifestyle.

11209 Macaw Court, Windermere
7230 Sangalla Drive, Windermere
$1,100,000
4 Beds ⋅ 4 Baths ⋅ Casa De Lago Rep SubDv. ⋅ 34786 Zip Code
Original-owner David Weekley Mediterranean in gated Casa Del Lago, on the coveted east side of Windermere near Isleworth and Keenes Pointe, minutes from Walt Disney World and an easy walk to Sunset Park Elementary.From the moment you step inside, rich hardwood floors draw you through the study, formal dining room, family room, and primary suite, giving the home a warmth and continuity rarely found at this price point. The gourmet kitchen is the heart of it all, with 42" cabinetry, granite counters, a cooktop crowned by a designer vent hood, and stainless GE appliances, all open to the family room so no one misses the conversation. Sliders lead to an expansive covered lanai and a generous backyard with plenty of room for a pool, a garden, or simply space to breathe. A 3-car garage handles vehicles, toys, and storage with ease. Cared for by a single owner since David Weekley handed over the keys, this home delivers the Windermere address buyers are searching for. Gated privacy, top-rated schools, and Winter Garden Village shopping and dining are all minutes away, with quick access to the 429 and the charm of Downtown Windermere.

7230 Sangalla Drive, Windermere
703 E 6th Avenue, Windermere
$3,450,000
4 Beds ⋅ 5 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code
Exceptional waterfront living on the prestigious Butler Chain of Lakes. Discover an extraordinary expression of waterfront luxury in the charming Town of Windermere, where timeless Tuscan and Mediterranean architecture meets the elegance of refined Florida living. Ideally along the shores of Lake Down, part of the desired Butler Chain of Lakes, this exceptional residence offers a rare opportunity to experience breathtaking water views, sophisticated interiors and an unparalleled boating lifestyle. From moment you arrive, exquisite stone detailing and custom wrought-iron double entry doors establish a sense of architectural distinction. Beyond the grand entrance, soaring ceilings, expansive living spaces, and thoughtfully curated design elements create an atmosphere of understated elegance and effortless sophistication. Designed for grand-scale entertaining and intimate gatherings, the home's gracious formal dining room provides an elegant setting for memorable occasions. At the heart of the residence, an expansive great room seamlessly integrates a gourmet kitchen, casual dining area, custom bar and inviting natural gas fireplace. Framed by captivating waterfront views, this exceptional gathering space offers the ideal balance of luxury, comfort and functionality. The main-level primary suite serves as a private sanctuary, offering serene views of Lake Down and a beautifully appointed en-suite bath featuring dual vanities, two spacious walk-in closets, a luxurious jetted soaking tub and an oversized travertine shower. An additional main-level bedroom provides exceptional versatility, ideally suited for guest accommodations, a private executive office, fitness studio or creative retreat. Upstairs, two generously proportioned bedrooms provide additional privacy and comfort. Thoughtfully reconfigured from the home's original three-bedroom upper-level layout, one of these bedrooms has been transformed into an exceptionally spacious retreat, complete with its private balcony. Abundant storage throughout the residence, a spacious laundry room with a recently updated washer and dryer, and a three-car garage further enhance the home's everyday convenience. Beyond the interiors, an extraordinary outdoor oasis awaits. An expansive covered and screened lanai, custom swimming pool, lush, mature landscaping and picturesque waterfront surroundings create a private resort-inspired setting. Whether hosting elegant outdoor gatherings, enjoying a leisurely afternoon poolside, or simply taking in the tranquil beauty of the lake, every moment invites relaxation and enjoyment. For boating enthusiasts, the property's enclosed boathouse offers a distinctive waterfront amenity, featuring a protected boat area and an inviting screened retreat. With direct access to the 13 interconnected lakes of the Butler Chain, an exceptional lifestyle of boating, waterskiing, wakeboarding, paddleboarding and waterfront exploration awaits just beyond your doorstep. Adding to its appeal is the timeless charm of Windermere itself. Enjoy the town's celebrated weekly farmers market, boutique shops, inviting restaurants, local brewery, wine market and cherished community events. All this is complemented by convenient access to Orlando's premier shopping, acclaimed dining destinations, world-renowned attractions and Orlando International Airport.

703 E 6th Avenue, Windermere
5638 Nectarine Drive, Windermere
$1,550,000
5 Beds ⋅ 5 Baths ⋅ Lake Cawood Cove SubDv. ⋅ 34786 Zip Code
BEAUTIFUL LAKE CAWOOD VIEWS AND WATER ACCESS SET THE SCENE FOR THIS NEWLY BUILT WINDERMERE HOME! Situated on a PREMIUM LOT in Lake Cawood Cove, this residence welcomes you with a SPACIOUS COVERED FRONT PORCH, thoughtfully selected upgrades, and an elegant, spacious design. This Ashton Woods DUVAL FLOOR PLAN offers approximately 3,612 square feet of living space, 5 BEDROOMS, 4 FULL BATHROOMS, 1 HALF BATHROOM, and a 3-CAR TANDEM GARAGE, with the opportunity to build your own PRIVATE BOAT DOCK. Inside, 10-FOOT FIRST-FLOOR CEILINGS, 9-FOOT SECOND-FLOOR CEILINGS, and 8-FOOT DOORS enhance the spacious feel. LUXURY VINYL PLANK FLOORING extends throughout the living areas, bedrooms, and staircase, while the bathrooms and laundry room feature tile flooring. At the heart of the home, the GOURMET KITCHEN showcases UPGRADED CABINETRY EXTENDING TO THE CEILING, creating a beautifully finished appearance with abundant storage. A SPACIOUS ISLAND with additional cabinetry on the back, an upgraded appliance package, and a customized pantry layout combine style with everyday functionality. The kitchen connects seamlessly to the breakfast area and an impressive GREAT ROOM WITH A SOARING 2-STORY CEILING. Windows welcome natural light and capture views toward the lake, creating an inviting setting for everyday living and entertaining. A separate dining room provides additional space for special gatherings. The FIRST-FLOOR BEDROOM SUITE includes a closet and private full bathroom, offering a comfortable retreat for guests. Upstairs, the spacious PRIMARY SUITE features a TRAY CEILING, a LARGE WALK-IN CLOSET, separate vanities, and a walk-in shower. An additional bedroom suite includes its own full bathroom, while two more bedrooms share another full bathroom. A versatile LOFT offers space for a lounge, study, or recreation area, and the conveniently located upstairs laundry room completes the second floor. Carefully selected enhancements include UPGRADED BATHROOM TILE with wall tile extending to the ceiling, LIGHTING UPGRADES, and wood stair railings. Additional features include sound insulation in selected walls, FOAM INSULATION in the block walls of the living space and garage, and prewiring for ceiling fans, security, and two additional wireless access points. An UPGRADED FRENCH DOOR opens to the COVERED LANAI, where beautiful water views and a conservation area toward Lake Cawood create a peaceful, natural backdrop. At the rear of the home, BEAUTIFUL SUNSET VIEWS OVER THE WATER provide a picturesque setting for relaxing evenings and outdoor gatherings. SUMMER KITCHEN PLUMBING AND ELECTRICAL PROVISIONS provide the flexibility to personalize your outdoor entertaining space. Enjoy convenient access to Windermere Preparatory School, Windermere High School, Publix, Aldi, shopping, dining, Winter Garden Village, the 429 Expressway, and Central Florida’s world-famous theme parks. With its premium setting, distinctive finishes, and generous living spaces, this newly built residence offers an exceptional opportunity to enjoy the Windermere lifestyle. Schedule your private showing today! VIDEO, 3D TOUR, AND FLOOR PLAN LINKS ABOVE.

5638 Nectarine Drive, Windermere
11066 Ullswater Lane, Windermere
$3,600,000
5 Beds ⋅ 7 Baths ⋅ Reserve At Lake Butler Sound SubDv. ⋅ 34786 Zip Code
Experience luxury living in the heart of Orlando, with a 24-hour guard-gated Reserve at Lake Butler Sound in Windermere! Situated on an expansive 0.83-acre homesite, this stunning Mediterranean-inspired estate offers over 7,200 square feet of elegant living space, featuring 5 bedrooms, 6.5 bathrooms, and a spacious 4-car garage. Impressive architectural details, soaring ceilings, elegant finishes, and generous living areas create the perfect blend of sophistication and comfort. The beautifully designed kitchen opens to inviting gathering spaces, while the luxurious primary suite offers a private retreat. Step outside to your own resort-style oasis featuring a sparkling pool, outdoor kitchen, and expansive grounds ideal for entertaining. Ideally located near premier shopping, dining, golf, and world-class attractions. A rare opportunity to own an exceptional estate in one of Windermere's most sought-after communities. Schedule your private showing today!

11066 Ullswater Lane, Windermere
6206 Golden Dewdrop Trail, Windermere
$580,000
3 Beds ⋅ 3 Baths ⋅ Windermere Lndgs Ph 02 SubDv. ⋅ 34786 Zip Code
Welcome to 6206 Golden Dewdrop Trail in Windermere Landings — an opportunity to live in Windermere, one of Central Florida's most exclusive and sought-after addresses. Set among the Butler Chain of Lakes, Windermere is known for its privacy, tree-canopied streets, and lake lifestyle, yet it's just minutes to Restaurant Row, Winter Garden, and world-class attractions. This 3-bedroom, 2.5-bath, two-story home offers 1,984 square feet with an open main level and ceramic tile throughout the first floor: living and dining areas flow into a kitchen with granite counters, wood cabinetry, stainless appliances, and an island with seating. There's also a downstairs nook and a powder room on the first floor. Plantation shutters on all the windows and upgraded light fixtures run throughout the home. Upstairs, the primary suite has wood flooring and a double-vanity bath; two more bedrooms, a full bath, laundry, and a loft nook complete the level. Out back, a covered porch and paver patio overlook the privacy-fenced yard — ideal for enjoying Florida evenings at home. Windermere Landings offers a pool, clubhouse, and playground, all within this coveted Windermere location.

6206 Golden Dewdrop Trail, Windermere
8325 Vivaro Isle Way, Windermere
$799,900
4 Beds ⋅ 3 Baths ⋅ Windermere Isle SubDv. ⋅ 34786 Zip Code
Virtually Staged. **POND VIEWS & DISNEY FIREWORKS!** Prepare to be impressed by this beautifully appointed 4-bedroom, 3-bath home in sought-after Windermere Isle, offering an inviting blend of stylish living, thoughtful upgrades, and a picturesque pond backdrop with a fountain and conservation views. Designed for both everyday comfort and entertaining, the open floor plan is enhanced by a decorative coffered ceiling in the dining room and a custom built-in entertainment feature that adds architectural interest and a polished focal point to the family room. The kitchen is equally impressive with granite countertops, tile backsplash, stainless steel appliances, abundant cabinetry, and a large center island, complemented by an adjacent informal dining area for casual meals. Everyday functionality is thoughtfully incorporated with a built-in drop zone just inside the garage entry, conveniently positioned near the walk-in pantry and kitchen. A first-floor bedroom with a full bath nearby provides wonderful flexibility for guests, while a creative nook beneath the stairs features a built-in desk, storage, and chalkboard wall, offering a fun space for homework, crafts, or play. Upstairs, **laminate flooring** extends throughout the stairs and entire second floor, where a spacious loft provides another inviting gathering space. The primary suite offers a relaxing retreat with two large walk-in closets and a beautifully appointed bath featuring dual vanities, a freestanding soaking tub, and glass-enclosed shower. The outdoor setting truly sets this home apart. A screened lanai with summer kitchen overlooks the fenced backyard and tranquil pond with fountain, creating the perfect backdrop for dining, entertaining, or simply unwinding while enjoying Disney fireworks in the distance. The home is also equipped with solar panels, while the two-car garage features an EV charger and overhead storage. Upgraded landscaping enhances the home’s curb appeal. 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, beautiful pond setting, and desirable community amenities, this exceptional home offers an outstanding opportunity to enjoy the Windermere lifestyle!

8325 Vivaro Isle Way, Windermere
5021 Carillon Lane, Windermere
$625,000
4 Beds ⋅ 3 Baths ⋅ Summerport SubDv. ⋅ 34786 Zip Code
Welcome to this beautiful home in a highly desirable community known for its top-rated schools and beautifully maintained surroundings. Lush landscaping, graceful palm trees, and a covered front porch create a warm welcome. Inside, the foyer opens to a formal dining room with an elegant chandelier and a home office enclosed by glass French doors. Neutral tones, arched walkways, and wood laminate flooring are found throughout the main living areas. The spacious, open floor plan flows into the kitchen featuring shaker cabinets, granite countertops, a decorative backsplash, stainless steel appliances, a wine rack, and a large custom pantry with built-in storage. A dedicated laundry area with folding space adds convenience. The light-filled living room opens to a breakfast nook with a stylish rattan light fixture, bay window seating, and sliding glass doors leading to the pool. The private primary suite features double-door entry, a custom walk-in closet with extensive built-ins, and a spa-inspired bathroom with dual vanities, a large soaking tub, and a separate glass-enclosed shower. Three additional bedrooms and two full guest bathrooms with tub/shower combinations provide plenty of space for family and guests. Step outside to your own tropical retreat, complete with a screened-in pool, shaded gazebo, and vinyl fencing for added privacy. Updates include HWT 2023, HVAC 2019, and roof replacement in 2020. Conveniently located near entertainment, shopping and dining at Winter Garden Village, Walt Disney World, and major roadways including Florida's Turnpike, this home offers both comfort and accessibility. Schedule your private showing today!

5021 Carillon Lane, Windermere
5231 Lemon Twist Lane, Windermere
$559,900
4 Beds ⋅ 4 Baths ⋅ Summerport Ph 03 SubDv. ⋅ 34786 Zip Code
?? REMODELED HOME IN WINDERMERE! HIGHLY MOTIVATED SELLER! ?? 5231 Lemon Twist Ln, Windermere ??? 4 Bedrooms | ?? 2.5 Bathrooms Discover a spacious home that combines comfort and style. Featuring a remodeled kitchen, updated bathrooms, and carpet-free flooring throughout, this home is ready for you to make it your own. All appliances are included! Generous living spaces plenty of room to relax, entertain, and create lasting memories. Don’t miss this opportunity to call Windermere home! The seller is highly motivated and welcomes! ?? Contact me to schedule your showing and submit!

5231 Lemon Twist Lane, Windermere
8582 Powder Ridge Trail, Windermere
$630,000
4 Beds ⋅ 4 Baths ⋅ Windermere Trls Ph 3b SubDv. ⋅ 34786 Zip Code
Virtually Staged. EXCELLENT OPPORTUNITY TO LIVE OR INVEST! This impressive Kipling model with lake views offers an exceptional combination of comfort, upgrades, and flexibility. The property features fully paid-off solar panels, a whole-house water filtration system, and electrical connections in the parking area with the option to install EV chargers. The main home has been thoughtfully updated. All bathrooms have been renovated, including 3 smart toilets with heated seats. The flooring throughout the main home has been replaced with high-quality waterproof luxury vinyl, providing a modern, seamless look that is both stylish and easy to maintain. The primary bedroom features a private balcony, offering an inviting additional space to relax and unwind. The kitchen features stainless steel KitchenAid appliances, granite countertops, backsplash, and LED-lit cabinetry. The spacious loft above the garage provides even more versatility and additional living space. The main home is currently VACANT and easy to show. Only the attached in-law suite is currently rented on a month-to-month basis, and the property can be delivered completely vacant at closing, ready for its new owners to move in. One of the property's greatest advantages is the in-law suite with a private entrance, making it ideal for extended family, guests, or as an opportunity to generate additional rental income. The parking area also offers the option to add a separate washer and dryer for the future occupant or guest of the in-law suite. This flexibility makes the property an excellent option for first-time homebuyers, families looking for additional space, or investors seeking additional income potential. Outside, the property features fencing and paver walkways, creating welcoming spaces to enjoy the outdoors. Strategically located just minutes from Disney, restaurants, shopping, and Central Florida's major attractions, this property combines location, upgrades, and multiple possibilities under one roof. Ready for its next owner!

8582 Powder Ridge Trail, Windermere
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