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.

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ALL HOMES FOR SALE

Available Homes for Sale in Windermere, FL

Welcome to your own slice of paradise in Florida! Nestled on 4.743 acres of pristine land, this one-of-a-kind family compound offers unparalleled luxury and breathtaking views of Lake Butler on the Butler Chain of Lakes. With over 700 ft of lake frontage, sandy beaches, boat ramps, and docks, this estate is truly a waterfront oasis.

The family compound consists of two exquisite residences. The primary residence, located at 11900 Lake Butler Boulevard, boasts 11,253 sq ft of living space with 6 bedrooms and 6 bathrooms, providing ample room for relaxation and entertainment. This residence also features an attached guest house for added convenience and comfort.

The second residence, situated at 11910 Lake Butler Boulevard, features two separate two-bedroom homes with patios and balconies overlooking the lush tropical gardens. Each home includes its own gourmet kitchen and summer kitchen. The residence is also equipped with an elevator, ensuring easy access to all levels and adding an extra touch of luxury.

Indulge in the ultimate luxury with amenities such as a private theatre, gym, steam room, and sauna. Pamper yourself in the salon, or challenge friends to a game in the spacious game room. The summer kitchen, outfitted with top-of-the-line appliances, is perfect for outdoor entertaining with views of both sunrise and sunset over the lake.

For the culinary enthusiast, the gourmet kitchen boasts a large walk-in pantry and is equipped with everything you need to create culinary masterpieces. After dinner, retreat to the large wine cellar, complete with its own ducted cooling system, to savor your favorite vintages.

Outside, the meticulously landscaped grounds frame the spectacular views, creating a serene and tranquil atmosphere. Relax on the patio, take a dip in the pool, or stroll down to the sandy beach for a day of fun in the sun.

One of the standout features of this property is the private moat and drawbridge, leading to your own dock and boat ramp. This unique element adds an extra layer of exclusivity and charm to the estate.

This property also includes an additional parcel of land that encompasses the second residence, providing even more space and privacy for you and your guests.

Don't miss this opportunity to own a piece of paradise in Florida. With its incredible detail and craftsmanship, unmatched amenities, and prime location on the Butler Chain of Lakes, this family compound is truly a once-in-a-lifetime opportunity. Schedule your private showing today and start living the life of luxury you deserve.

$22,000,000 Active

11900 & 11910 Lake Butler Lake Butler Boulevard Windermere, Florida

6 Beds 6 Baths 11,253 SqFt 3.750 Acres

Under Construction. One or more photo(s) has been virtually staged. Welcome to your opulent retreat nestled in the heart of elegance! Building by Supreme International Construction one of the most reputed builder in Windermere. who is known for luxury homes. This palatial estate boasts an expansive 20,445 Square feet of luxurious living space, offering unparalleled comfort and sophistication at every turn. Step inside and indulge in the epitome of lavish living.
Entertain in style with your very own private bowling alley and arcade where evenings are spent in friendly competition and laughter echoes through the halls a heaven for all , where endless hours of entertainment await.

For those moments of quiet reflection, escape into the tranquility of the library, a sanctuary of knowledge and serenity. Lose yourself in the pages of your favorite novels or simply bask in the ambiance of this refined space.

Indulge in ultimate relaxation with your own massage room. Step outside to your sunken gazebo, a picturesque oasis surrounded by lush landscaping, perfect for intimate gatherings or peaceful solitude.

Take a dip in your choice of pools-whether indoors in the serene ambiance of your indoor pool, or outdoors under the sun in the sparkling waters of your outdoors under the sun in the sparkling waters of your outdoor pool. With options for every mood and occasion, luxury living has never been more inviting.

For young and young at heart, a hidden hide-and-seek room adds an element of whimsy and surprise. And for the ultimate in convenience and luxury, ascend to the rooftop helipad and take flight to any destination in style.

With every conceivable amenity at your fingertips, this estate epitomizes extravagance beyond compare, Don't miss your chance to own a residence that embodies the essence of refined living.

$15,950,000 Active

9621 Windy Ridge Road Windermere, Florida

9 Beds 16 Baths 20,445 SqFt 2.500 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 offer 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.

$13,900,000 Active

4200 Down Point Lane Windermere, Florida

6 Beds 9 Baths 14,435 SqFt 1.600 Acres

$13,250,000 Active

9832 Laurel Valley Drive Windermere, Florida

6 Beds 10 Baths 11,100 SqFt 0.600 Acres

Keene's Pointe - Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and media room, 2 offices, 6 full/2 half baths and 6 bedrooms - one of which could serve as a in-law suite with separate entrance from the outside. From the moment you enter this impeccably designed home ALL ON ONE FLOOR, you are greeted with style and elegance. Featuring built in cabinets, shelving, and wall panels, powered blinds and drapes, lighting controls, designer features and modern decor. The formal living and piano room spotlights a lighted onyx wall and two-sided gas fireplace opening up to the family room and formal dining which leads to the kitchen and media room. The primary suite with two spacious closets and spa-like bath is located privately away from the secondary bedrooms. The house was designed to maximize views of the lake and access to the enclosed lanai which has a sitting room with fireplace, dining area, half bath and kitchen with grill, sink, ice maker and refrigeration. This home has 7 garages, a 4-car garage with EV charging station and air conditioning adjoins the house and a separate 3-car garage on the opposite side of the courtyard which could also be renovated into a separate guest house if needed. There is plenty of deck space around the pool and spa for entertaining and the spacious back yard leads the way to the covered boat dock with boat and jet ski lifts. Located in Windermere, Florida, with top-rated public and private schools, shopping, dining, close to tourist attractions and expressways. This home is your dream come true!

$11,999,999 Active

6149 Grosvenor Shore Dr Windermere, Florida

6 Beds 8 Baths 6,783 SqFt 2.650 Acres

Stunning modern masterpiece situated in Windermere's Reserve on Lake Butler Sound's most coveted waterfront lot. Known as "Overjoy" for its location on the sparkling waters of Lake Butler with unprecedented long lake views. Built by renowned builder Jones Clayton Construction and designed by coveted architect Mark Nasrallah, this collaboration is simply epic! The 14' glass double entry doors welcome you into this open floor plan, featuring 5 bedrooms, 7 full and 2 half baths with expansive unobstructed 140' lake views. This world class Aurora Award winning estate incorporates signature art deco design finishes and innovative architectural design. The main living area features a fireplace with Swarovski crystal insets, a Biazzi glass mosaic inset into the Benjamin grade Jerusalem limestone flooring, coffered ceiling with nine art deco-inspired custom chandeliers that complement the living room with extravagant floor to ceiling glass walls which offer inspiring views of the lake and 38' x 38' infinity edge pool and heated spa. The kitchen and family room are a work of art with cobalt blue ceiling insets that complement the blue Bahia granite countertops. Enjoy the efficiency of the kitchen and the clean lines of the Aigner cabinetry. The stunning first floor master suite offers Calcutta gold marble flooring, floor to ceiling glass walls, his and her two story dressing areas with a massage area, steam shower, sitting area, balcony and outdoor glass garden. A lovely private guest room is also conveniently located on the main floor. The floating glass 4 person elevator transports you to the second level where you'll enjoy the state of the art home theater with sueded walls and Kaleidescape media system. The third level provides three additional en suite bedrooms with views of the lake, plus a spacious loft and second laundry room. The expansive travertine driveway, air conditioned three car garage (not included in living SF amount), 2,800 feet of pool decking, and 1,000 feet of sun decking offers the ultimate in resort style living nestled among palm trees and endless vistas with panoramic views. This Central Florida estate is unmatched and perfectly located only 30 minutes to Orlando International Airport, 15 minutes to Disney, and just minutes from world famous golf courses, shopping & simply the best dining the Orlando area has to offer bar none!

$11,995,000 Active

11301 Bridge House Road Windermere, Florida

5 Beds 9 Baths 9,267 SqFt 0.930 Acres

Located in the prestigious Town of Windermere, this spectacular 1.2-acre property on the renowned Lake Butler Blvd. offers the rare chance to build a truly custom estate home that defines luxury. This stunning two-story modern architectural masterpiece will feature over 14,000 SF of exceptional living and entertaining space, designed with both comfort and elegance in mind.

With six spacious bedrooms and nine luxurious bathrooms, the estate is designed to impress. Three primary suites ensure the utmost in privacy and sophistication, including a grand first-floor suite that boasts dual walk-in closets, a sauna, and your very own Turkish Hammam. Each bedroom is designed with en-suite bathrooms and private balconies, providing breathtaking views and tranquil retreats. The guest suite also offers an expansive outdoor entertainment deck with gorgeous lake views.

Entertainment is endless in this home. The main floor will house a custom game room, while the upper level will feature a state-of-the-art 14-seat theater room. The outdoor space is equally spectacular, with over 1,000 SF of alfresco living areas, including a summer kitchen, overlooking a private pool and spa paradise. Imagine your own custom-designed water and fire features, creating an oasis more enchanting than the fountains of Bellagio.

Designed and built by the esteemed Supreme International Construction, this estate will be constructed with the finest materials, featuring solid concrete and steel for unmatched durability. Every finish, from the flooring to fixtures, will be high-end and tailored to your preferences, making this home a true one-of-a-kind sanctuary. Additional highlights include a glass elevator leading to an elevated floating catwalk, a magnificent great room with soaring ceilings, an office/library, a 5-car garage, and water fountain features.

The estate will be fully furnished with exquisite high-end furniture and finishes, personally curated to create an atmosphere of luxury and comfort. You’ll even receive a luxury vehicle to match the style of this magnificent home, making your move completely stress-free. Simply bring your clothes, and you’ll be ready to indulge in this unparalleled lifestyle from day one.
This exquisite home offers unobstructed views of Lake Butler and exclusive access to the Town of Windermere's resident boat ramp.

If you’re seeking unparalleled luxury, modern design, and a lifestyle of elegance, look no further. Your dream home is waiting. Contact us today for more details.

$9,998,500 Active

11947 Lake Butler Boulevard Windermere, Florida

6 Beds 9 Baths 14,364 SqFt 1.200 Acres

$8,650,000 Active

5507 Worsham Court Windermere, Florida

5 Beds 11 Baths 10,200 SqFt 0.980 Acres

$7,999,000 Pending

9313 Tibet Pointe Circle Windermere, Florida

6 Beds 8 Baths 8,792 SqFt 2.880 Acres

Under contract-accepting backup offers. Stunning Butler Chain masterpiece, built by Goehring & Morgan, located in the 24-hour guard gated community of Keene’s Pointe. This home is perfectly positioned along the shores of Lake Tibet with approximately 135 feet of lake frontage and one of a kind unobstructed lake views. As you pull down the stately 140-foot-long driveway the car enthusiast is sure to love the expansive motor court and 5 car garage. Stepping through the front doors your eyes are immediately greeted by a bright open floorplan with a wall of windows overlooking the lake and pool. The chef’s kitchen features a huge center island with a prep sink, top of the line appliances, 3 ovens, a massive hidden pantry, and a large breakfast nook with corner windows. The expansive primary bedroom suite features its own private entrance & garden, a separate sitting area overlooking the pool, and a spa bath with a large walk-in shower with multiple shower heads, a jetted tub, and a full sauna. Additional amenities include a study with built in bookshelves, a first-floor game room and theater, wine cellar, and a dedicated bar area. An exquisite, curved staircase leads to the second floor which features additional bedrooms and baths, a loft area, second laundry area, and a home gym / flex space above the garages. Open the corner sliders in the game room, lower the retractable screens and the expansive outdoor covered lanai is seamlessly blended with the indoor spaces which is perfect for entertaining. Additional exterior amenities include a massive resort style pool with multiple rock waterfalls, a beach area, hot tub, and even a water slide. There is also a summer kitchen, fire pit, and of course a covered boat dock with plenty of room for your boat and multiple jet skis. Keene's Pointe features an 18-hole Jack Nicklaus-designed golf course, an amazing private country club with two restaurants, pool, fitness center and tennis courts. Located just minutes from fine dining, world-class shopping and all the area attractions, this location quite simply can't be beat. Don’t miss your opportunity to own this one-of-a-kind Keene’s Pointe residence.

$6,995,000 Pending

6131 Grosvenor Shore Drive Windermere, Florida

7 Beds 9 Baths 8,596 SqFt 3.750 Acres

One or more photo(s) has been virtually staged. Welcome to this stunning estate, a masterpiece of design and functionality, where every detail has been meticulously crafted to create the perfect family retreat. Within the Isleworth Golf and Country Club community, this expansive property boasts over 8,000 square feet of luxurious living space, featuring a complete remodel with structural add-ons that have added over 2,000 square feet to the original footprint. The home is equipped with five ensuite bedrooms, each with its own full bathroom, providing privacy and comfort for every member of the family. Totaling seven full bathrooms and one-half bath, along with space for a state-of-the-art gym and an office, this home ensures ample space and convenience for guests and residents alike. An open family entertainment space, equipped with a fully functional wet bar, seamlessly flows into an outdoor kitchen, making the indoor-outdoor living a breeze is complete with a sparkling pool, hot tub, and a large sunken fire pit area. The formal living room welcomes you with large windows infusing natural light and showcasing a stunning glass wine room. The primary bedroom has been transformed with an expansion that includes oversized his and her closet suites, offering ample storage and a luxurious dressing experience. This estate is not just a home; it's a lifestyle. From the carefully designed living spaces to the luxurious amenities, every aspect of this property has been tailored to create the ultimate family paradise.

$6,900,000 Active

5518 Worsham Court Windermere, Florida

5 Beds 8 Baths 8,203 SqFt 0.990 Acres

Welcome to this stunning ultra-modern home located in the prestigious gated community of Windermere, FL. This architectural masterpiece boasts 4 spacious bedrooms and 5 luxurious bathrooms.

Upon entering, you are greeted by a grand living area designed for both comfort and elegance, perfect for hosting gatherings with friends and family. The open-concept space seamlessly flows to an expansive covered patio, featuring an outdoor grill and ample space for alfresco dining and parties, providing the perfect setting for memorable entertaining.

Situated on the lake, this home offers breathtaking views that can be enjoyed from multiple vantage points throughout the property. The backyard sanctuary includes a pristine pool, enhancing your outdoor living experience.

Additional features of this exceptional residence include a 3-car garage and exquisite luxury details meticulously thought out in every corner of the home. From high-end finishes to premium fixtures, no detail has been overlooked.

This is not just a home; it’s a statement of modern elegance and luxury living. Discover your next sanctuary in one of Windermere’s most coveted neighborhoods.

Contact us today for a private showing and experience firsthand why this home is truly a masterpiece.

$6,500,000 Active

12264 Montalcino Circle Windermere, Florida

4 Beds 8 Baths 7,875 SqFt 1.370 Acres