Windermere, FL Homes for Sale & Local Guide

Windermere is one of the nicest small towns in Florida. Windermere Single-Family homes are surrounded by beautiful lakes, golf courses, fine dining, scenic views, and highly-rated schools. It is a town in Orange County, Florida, United States and is located on the secondary roads about 15 miles west-southwest of downtown Orlando on the Butler Chain of Lakes.

These lakes are popular places for waters skiing, boating and fishing. Windermere is a residential community with a population in 2022 of less than 4,000. Even though it is a very small town, the greater Windermere area has been steadily growing. In the years before the giant freezes of the 1890s and the 1980s, this small town was in the heart of one of the largest citrus regions in the world.

Founded in 1889, Windermere is one of the oldest communities in Orange County. By 1910, the Windermere Improvement Company had been formed, homes were built and thousands of acres of citrus planted all around the area. Many of these old homes and buildings have been preserved and add to the charm of this little place nestled among the old oaks and clear lakes of Central Florida. The quiet neighborhoods of Windermere are located on an isthmus between Lake Down and Lake Butler. The downtown area has a small town feel.

Windemere, FL Homes For Sale Statistics

View Market Report

Windemere

default

windermere-fl-2

windermere-fl-3

windermere-fl-2

windermere-fl-3

Search Windermere, FL Listings By Price

$200,000 TO $300,000

$300,000 TO $400,000

$400,000 TO $500,000

$500,000 TO $700,000

ALL HOMES FOR SALE

Available Homes for Sale in Windermere, FL

Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere’s largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 feet of lake frontage, a private island with moat and drawbridge, sandy beaches, two story double residence guest house, and a majestic and stunning grand mansion with additional guest retreat, all spanning more than 14,444 square feet of living space and 11 bedrooms across both residences. Welcome to this one-of-a-kind haven of privacy and prominence showcasing the best of Central Florida living. Set on a rare 3.75 acres commanding enviable views on the northern shore of Lake Butler, every detail has been thoughtfully designed to celebrate both refinement and tranquility. The impressive palatial main residence boasts 10,649 square feet of living space with 6 bedrooms plus a one-bedroom guest retreat and an array of curated spaces. The Spanish Eclectic interior fuses classic craftsmanship with modern sophistication, creating an inviting and awe-inspiring escape from the ordinary. On entrance be greeted by sweeping floor to ceiling windows to allow breathtaking water vistas, double-sided gas fireplace, a grand colonnade hallway, and architectural details throughout. The gourmet chef’s kitchen features top of the line appliances, gas range with multiple burners, ovens, island with second sink, and walk-in pantry. A sports bar games room and showstopping home theater provide an abundance of entertaining options. Other notable amenities include a Castilian wine cellar, bay windows, two wet bars, private salon, elevator, gym, steam room and sauna. Outdoors, a generous summer kitchen with automatic roller screens provide an outdoor oasis for al fresco dining, cooking, or relaxing. The zero-entry infinity pool and vast resort decking provide a breathtaking vantage point for panoramic views of Lake Butler’s radiant sunsets, while the shaded Zen garden and white sandy beach offer a tranquil retreat for quiet reflection. With many distinct outdoor venues, serenity is never far away. The estate’s private island, accessed by an electric drawbridge, and a boat ramp provide unmatched exclusivity to Lake Butler and the world-famous Butler Chain of Lakes. The two-story detached guest house offers 3,795 sq feet of living space across two, 2-bedroom apartment homes, each with kitchens, laundry rooms, an elevator, and attached two-car garage. Built for a large multi-generational family, guest quarters, or on-site caretakers, the possibilities are endless. Truly a picture-perfect unmistakable showplace offering the very best for the most discriminating buyer.

$20,000,000 Active

11900 Lake Butler Boulevard Windermere, Florida

7 Beds 9 Baths 10,649 SqFt 3.75 Acres

Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry Irwin and built by Ballard Construction, with interior designs by Faith Fournet, the property has been fully transformed and thoughtfully curated over the last three years to deliver exceptional comfort, sophistication and panache at every turn. The two-story estate is set on a pristine 1.02-acre golf-front home site along Isleworth's famed championship golf course and from the moment you enter, you'll be captivated by the artistry in design and modern innovation. The interiors span more than 9,500 square feet living and 13,000 under roof, blending 5 bedrooms, 5.5 baths and an array of indoor and outdoor living areas with uncompromisingly luxurious finishes designed for effortless entertaining and quiet moments alike. At the heart of the home, the showstopping glass-enclosed wine room—temperature-controlled and with a 2,400-bottle capacity—is a collector's dream and the ultimate conversation piece. The primary suite is a sanctuary unto itself, featuring a magnificent two-story closet and dedicated dressing room with a bar. Indulge in true tranquility within the home’s private wellness suite, complete with exercise room, a rejuvenating steam room, dry sauna and invigorating cold plunge tub. Additional interior highlights include the grand kitchen with Cristallo quartzite lighted countertops; a fully custom lounge with full bar; an upper-level game room with bar; an oversized, air-conditioned garage accommodating up to 8 vehicles; two laundry rooms; and more. Outdoor spaces are equally impressive, with an expansive lanai and balcony, a custom swimming pool with fire pits, meticulously landscaped yard adorned with integrated lighting, sound and lush, native greenery and putting green —all overlooking panoramic views of Isleworth’s championship golf course. Whether hosting guests or enjoying a peaceful evening at home, this estate offers a rare opportunity to live a life of unmatched beauty, comfort, and distinction in one of Central Florida's most desirable enclaves.

$14,250,000 Active

5525 Isleworth Country Club Dr Windermere, Florida

5 Beds 6 Baths 9,511 SqFt 1.02 Acres

Nestled along almost 1,000’ of the highly sought after Butler Chain of Lakes in Windermere, this exquisite Mediterranean estate beckons with unrivaled opulence. Beyond a private gate, a 2-acre peninsula reveals a masterpiece of architectural brilliance designed by Nasrallah and built by Ray Coudriet. The grand entry sets the tone, with a majestic staircase, a 25+ft hand-painted rotunda ceiling, and a stunning 10-ft Waterford chandelier. Every inch of this residence exudes sophistication, from the marble floors and corbels to the intricately carved fireplace mantels or even the ornate door hinges. Boasting 5 spacious bedroom suites, four with outdoor walk-outs, in the main home, complemented by a separate guest/staff apartment, this estate offers flexibility and privacy. A resort-style pool, cabana, along with a boathouse, dock and paver paths meandering through the property, create an outdoor haven for entertaining and relaxation. The guest quarters or a private office that takes in views from 3 sides. Architectural marvels abound, with handcrafted coffered ceilings, exposed wood beams, and a gourmet kitchen featuring a red brick barreled ceiling and appliances by Wolf and Sub-Zero. Hosting events is effortless with a separate full caterer's kitchen. The primary suite offers serene panoramic water views, complemented by an extraordinary dressing room and bathroom. For wine connoisseurs, a climate-controlled 3,000+ bottle wine cellar awaits. Verandas and terraces afford fresco dining, bar area and sweeping views, enhancing the outdoor experience. Work in the masterful office with birds’ eye 180-degree water views or step into the game room for a game of pool or a sunset view off the balcony. A large travertine parking area for events and a 4-car garage adds practicality to this extraordinary property. This masterpiece transcends the ordinary, offering a lifestyle of unparalleled luxury and sophistication. Seize the opportunity to make this stunning estate your own.

$11,900,000 Active

4200 Down Point Lane Windermere, Florida

6 Beds 9 Baths 14,435 SqFt 1.6 Acres

Experience luxury lakefront living on a grand scale in this custom-built Modern Mediterranean estate on Lake Tibet, part of the pristine Butler Chain of Lakes. The three-story residence spans 9,571 square feet of living space on over 2.2 acres in the guard-gated community of Keene’s Pointe in sought-after Windermere. Built by Goehring & Morgan, this architectural masterpiece offers refined craftsmanship, exquisite details and seamless indoor-outdoor living with stunning water views from almost every space. The 26-foot grand entry sets the tone for soaring handcrafted coffered ceilings, travertine marble and mahogany wood floors, custom cabinetry, designer interior and exterior finishes and an open floor plan. Inside you'll find six bedrooms, five en suite, nine baths, formal living and dining rooms, wine cellar, family room, captivating saltwater aquarium, game room, lounge/loft, two offices, a mudroom, and a home theater constructed of concrete block to also serve as a safe room. The chef’s kitchen is outfitted with Sub-Zero and Dacor appliances, Esmeralda Brazil granite countertops, LED lighting, a large walk-in pantry, a prep kitchen with additional appliances and a built-in Miele coffee station with beverage refrigerator. The owner’s retreat features a private sitting room, fireplace, wet bar, oversized custom closet, spa-like bath and a covered balcony with breathtaking lake views. A spiral staircase leads to the third floor, the highest elevation in Keene’s Pointe, where you’ll find a private study and an observation deck. Massive sliding doors open to a spectacular outdoor living space with retractable screens, tongue-and-groove ceilings, fireplace, TV and a full summer kitchen with Viking gas grill, sink and refrigerator. The resort-style saltwater pool features a Beadcrete finish, sun shelf, lazy river, slide, grotto, swim-up table and stools, island planter with palm trees, spa and dramatic water, fire and lighting effects. A putting green and built-in trampoline complete the backyard oasis. One of only two, two-story docks in Keene’s Pointe, the home's private boathouse includes two boat slips with lifts and touchless covers, plus a floating dock for jet skis. Additional features include an elevator, in-floor vacuum system, attached in-law suite with private entry plumbed for a future kitchen, two garages with room for five cars and a gated dog run. The barrel tile roof, stone entry columns, motor court with fountains and professionally designed landscaping further elevate the estate. Keene’s Pointe offers access to the Butler Chain of Lakes, a 250-acre Jack Nicklaus Signature golf course, the Golden Bear Club, resort-style pool, tennis courts, fitness center, multiple playgrounds and a clubhouse for private events. Windermere offers small-town charm with proximity to downtown Orlando, fine dining, world-class shopping, championship golf courses, top-rated schools, international and private airports, and theme parks.

$9,500,000 Active

6137 Grosvenor Shore Drive Windermere, Florida

6 Beds 9 Baths 9,571 SqFt 2.2 Acres

Welcome to this grand residence nestled on a sprawling 1.17 acre lot originally hand selected by golf legend Arnold Palmer. Perfectly positioned to capture breathtaking views of the first and tenth holes, this remarkable estate provides a lifestyle of unmatched elegance and comfort.

Meticulously maintained, this grand estate encompasses 11,403 square feet of living space thoughtfully designed to provide both functionality and style. No space has been overlooked, from the ideally located gourmet kitchen to the well appointed laundry room. This home boast seven generously sized bedrooms along with ten full and three half baths each crafted with exquisite attention to detail. With two additional bonus rooms—one of which could easily serve as an eighth bedroom—and a dedicated office, this estate provides unparalleled flexibility to accommodate your every need.

Venture outside to discover your private sanctuary—a stunning outdoor oasis perfect for hosting lavish events or enjoying tranquil moments surrounded by lush landscaping and sweeping panoramic views. The expansive grounds are enhanced by a separate guest house with two complete living spaces and a six-car garage tailored for the car enthusiast.

From the well designed interiors to the manicured exteriors, this estate represents the pinnacle of refined living. Its distinctive lot combines spaciousness, privacy, and stunning vistas to create a one-of-a-kind retreat.

$8,775,000 Active

5271 Isleworth Country Club Drive Windermere, Florida

7 Beds 13 Baths 11,403 SqFt 1.17 Acres

$8,499,000 Active

9832 Laurel Valley Drive Windermere, Florida

6 Beds 10 Baths 11,100 SqFt 0.6 Acres

PRICE IMPROVEMENT!!
Perfectly sited on pristine Lake Tibet in Keene's Pointe Country Club, this stunning lakefront Stonebridge custom home has been completely
updated. The modern exterior color brightens the façade and creates a unique transitional style. The wrought iron and glass doors add a refined entry. Opening to the two-story formal areas featuring timeless elements of stone flooring, elegant ceiling details, clerestory windows, and expansive lake views set a modern tone. At the center of the home, the kitchen is a chef's dream; stone flooring and a massive working island, state-of-the-art appliances combine function and beauty with double ovens, exotic granite, stunning glazed custom cabinetry, and a huge walk-in pantry. The gourmet kitchen opens naturally to the family gathering areas, complete with sparkling lake views. A fireplace shares the media wall with a built-in entertainment center, while French doors give access to the outdoors. Just off the family area, the game room is finished with a beautiful bar area. The state-of-the-art home theatre is located just off the game room. Entertain outdoors in true Florida style; the outdoor gourmet area was added in 2019, including a large bbq grill area, massive dining/working island, wine cooler, XL Fridge as well as a pizza oven. The free-form pool, heated spa, and boat dock with lift. The master suite is private with huge master closet and beautifully finished master bath. All secondary bedrooms are ensuite. All baths have been updated. The entire
home has been freshly painted and all carpet has been replaced. The detached guest house is great for extended family.

$8,490,000 Active

9343 Tibet Pointe Circle Windermere, Florida

7 Beds 10 Baths 8,362 SqFt 1.54 Acres

Experience luxury living at its finest in the high end gated community of Isleworth. Nestled on the 6th fairway of Isleworth’s world-renowned golf course, this beautifully redesigned estate offers over 6,900 square feet of exquisite living space, featuring 5 bedrooms and 6.5 bathrooms. Completely reimagined by renowned architect Mark Nasrallah, the home blends modern elegance with resort-style comfort. From the moment you arrive, you’re welcomed by a striking 10-foot-tall custom pivot door and an open-concept layout flooded with natural light and elegant design elements—truly an entertainer’s dream. The main living area features lavish, exotic flooring that is both elegant and inviting. A sleek, contemporary fireplace creates a stylish yet cozy setting for everyday living and entertaining. The chef’s kitchen is the heart of the home, complete with high-end appliances, custom European cabinetry, designer countertops, and an oversized island. A hidden pantry with a secondary prep area is ideal for hosting and everyday functionality. A temperature-controlled wine cellar adds an elegant touch of sophistication—perfect for showcasing and preserving your finest vintages. The spacious downstairs primary suite is a private retreat, where every detail goes above and beyond. From custom chandeliers and stunning LED lighting to a spa-inspired bathroom featuring an elegant soaking tub, a massive walk-in shower, and a tropical outdoor shower, this space feels like a luxury resort. The designer walk-in closet is sure to impress with its custom lighting and exquisite finishes. A versatile bonus room off the suite offers endless possibilities and opens directly to the stunning pool deck overlooking the golf course. A massive sliding glass door allows for a seamless indoor-outdoor living experience, making entertaining effortless and luxurious. Nearby, a private office features floor-to-ceiling glass, built-in cabinetry, refined finishes, and abundant natural light—creating a bright and inspiring workspace. As you ascend the custom floating staircase, you’re greeted by lush built-in planters below, evoking a tranquil island-inspired ambiance. The upper level continues to impress with a secondary primary suite, complete with a luxurious bathroom and spacious walk-in closet. Another upstairs bedroom includes its own en-suite bathroom and walk-in closet. The expansive game room is perfect for family fun or entertaining guests and opens to a grand balcony with panoramic golf course views. The home theater is modern and inviting, showcasing custom LED lighting, two-tiered seating, and state-of-the-art sound for a true cinematic experience. Step outside to your personal oasis—featuring a sleek pool with a heated spa, surround sound throughout the exterior, an outdoor kitchen, wet bar, and lush, professionally designed landscaping. This smart home is fully integrated with a Crestron system that controls lighting, security, audio, climate, and more—all at your fingertips. For added peace of mind, the property is equipped with a backup generator to ensure uninterrupted comfort. Located in one of Central Florida’s most exclusive communities, this property offers not only unmatched amenities and top-tier finishes, but also an extraordinary lifestyle of luxury and leisure. Contact us today to schedule your private tour and experience the pinnacle of Isleworth living.

$8,325,000 Active

5074 Isleworth Country Club Drive Windermere, Florida

5 Beds 7 Baths 6,937 SqFt 0.54 Acres

$7,500,000 Pending

5507 Worsham Court Windermere, Florida

5 Beds 11 Baths 10,200 SqFt 0.98 Acres

Step into timeless elegance, luxury, and sophisticated living. Located in the exclusive man-gated community of Lake Butler Sound—one of Central Florida’s most prestigious communities. From the moment you enter, you're greeted by high-end finishes, open-concept living space, and meticulous attention to detail. This stunning residence offers nearly 9,000 sqft of elevated living space featuring 5 spacious bedrooms, 8 luxurious bathrooms, and your very own private detached guest suite offering unparalleled comfort, perfect for having guests and upscale hosting. Enjoy cinematic experiences in your private movie theatre, with reclined seating, host unforgettable gatherings in the state-of-the-art entertainment center, and set the perfect ambiance with built-in speakers flowing music throughout the residence. This home is beautifully designed with an indoor-outdoor flow, making it an entertainer's dream. Step outside to a serene koi pond, lush landscaping, heated pool and your very own dock with direct water access to the Butler Chain of Lakes. This rare estate offers a combination of space, style, and status—a truly unmatched opportunity in Windermere.

$7,500,000 Active

11103 Bridge House Road Windermere, Florida

5 Beds 8 Baths 8,443 SqFt 1.74 Acres

Under contract-accepting backup offers. Nestled within the highly sought after, guard-gated community of Lake Butler Sound, this breathtaking lakefront estate has been completely remodeled with designer interior and exterior finishes, offering an unparalleled blend of sophistication and modern luxury. Positioned on an expansive corner lot, this home boasts breathtaking panoramic lake views from nearly every room, creating a serene and picturesque setting for the most discerning buyer. Step inside to discover impeccable craftsmanship and exquisite architectural details throughout. The primary suite is a private retreat, featuring an elegant sitting area, a two-story custom closet, and a spa-inspired bath with an oversized soaking tub, a luxurious walk-in shower overlooking a private courtyard, and exquisite designer finishes that elevate the experience of relaxation. The gourmet kitchen is a chef’s dream, outfitted with top-of-the-line appliances, a large center island with a separate prep sink, a hidden pantry, stunning marble countertops and a marble back splash that showcase both beauty and function. This culinary space seamlessly flows into the open living and entertaining areas, where you’ll find a first-floor home theater, a wine cellar, a home gym/ 6th bedroom, and a stunning game room with dramatic arched ceilings and a wall of windows that frame breathtaking lakefront vistas. The second-floor features three luxurious en-suite bedrooms, a spacious lounge area, and a sprawling balcony that overlooks the resort-style pool and the shimmering waters of Lake Butler. The outdoor spaces are equally captivating, with lush landscaping, multiple covered patio areas for alfresco dining, a summer kitchen, a triple gas fire pit, and an extraordinary resort-style pool complete with a hot tub, stair-stepped waterfall feature, and a travertine marble patio. At the water’s edge, an expansive private boat dock provides direct access to the renowned Butler Chain of Lakes, perfect for boating, fishing, and water sports enthusiasts. With every detail thoughtfully curated and no expense spared, this remodeled masterpiece is the pinnacle of lakefront luxury living.

$7,150,000 Pending

6126 Kirkstone Lane Windermere, Florida

5 Beds 7 Baths 8,691 SqFt 1.42 Acres

$6,800,000 Active

9259 Tibet Pointe Cir Windermere, Florida

5 Beds 6 Baths 6,257 SqFt 2.21 Acres