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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. As of the 2010 census, the town population was 2,462.[6] It is part of the Orlando Metropolitan Statistical Area. It is best whether you want to relax or play, this community has amenities for you to enjoy.It is located on an isthmus between several lakes in the Lake Butler chain.As such, it is on the shortest road route between the east and west sides of the chain. In fact, the next crossing to the south is 7.5 miles (12.1 km) distant at Lake Buena Vista, where County Road 535 (CR 535) and Apopka-Vineland Road meet. The next crossing to the north is at Gotha, the north end of the chain of lakes, 2.25 miles (3.62 km) away. 2003 Annual Average Daily Traffic (AADT), much of which is commuters passing through, is 17,197 vehicles per day for Sixth Avenue (the east entrance), 18,362 on Main Street north of Sixth Avenue, and 9,484 on Main Street south of Sixth Avenue. It is one of the oldest communities in Orange County. By 1910, the Improvement Company had been formed, homes were built and thousands of acres of citrus planted all around the area.

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Available Homes for Sale in Windermere, FL

Perfectly positioned on 18 acres of meticulously manicured grounds, this walled and gated compound offers over 625 feet of picturesque and panoramic views on Lake Down of the Butler Chain of Lakes. The options available to further develop this property are endless in expanding/building more structures, various ways to subdivide, parcel into a family compound, or continue to enjoy it as one massive private gated lakefront estate as utilized currently. The magnificent sprawling primary residence pairs classic Georgian architecture with modern amenities to achieve the ultimate lakeside retreat encompassing almost 50,000 "total square feet under roof" in all buildings on the property. Employing the finest materials and finishes, the elegant entryway opens into a grand interior boasting a floating mahogany staircase, marble floors and paneled walls all framed by stunning Murano chandeliers. An art gallery leads into a spacious living room lined with mahogany walls and faces wide waterfront scenes. The gourmet kitchen is a chef’s delight featuring a salamander for warming and broiling, two double convection ovens, a large commercial icemaker and a commercial refrigerator and freezer. Downstairs also includes one of two owner's suites along with a spacious library-lounge or possible 6th bedroom suite. Two staircases or a commercial Thyssenkrupp elevator offer access to the second level featuring four more expansive bedroom suites, including the main owner's retreat, and an 85-foot parlor highlighted by 20-foot ceilings, bookshelves and a wet bar — the perfect venue for hosting family and friends. A screened porch captures spectacular southern lakefront views and the nightly Disney fireworks display. Connected by a breezeway, a grand rustic lodge comprised of 5,600 square feet and equipped with a large bar, catering kitchen, entertainment hall and locker facilities offer limitless potential. Just in front of the lodge, a shimmering Junior Olympic pool and spa complete with fountain and light features await. Additional outstanding appointments include a 3,800-square-foot storage building with 20-foot ceilings, staff quarters with 576 square feet of living space, a patio area and courtyard and a 4,000-square-foot paneled garage with separate office, guest apartment and 20-foot ceilings for the auto aficionado’s treasured collection with 3 separate garages including room for a full-size motor coach and 50+ car collection. Situated in one of Central Florida’s most sought-after locations, this truly exceptional estate epitomizes luxury, privacy and sophistication to offer an enviable lakefront lifestyle. *Further notes: Almost 500 live oak trees surround the perimeter of the grounds. Conveniently located just north of the center of town, a short distance to the Grove and Olympia High School as well as access to the 408 in less than 3 minutes. $30,000,000 Active

9508 Windy Ridge Road Windermere, Florida

7 Beds 16 Baths 29,739 SqFt 18.160 Acres

Sitting on one of the most magnificent and private lots in all of Windermere, with your own personal view of nightly Disney fireworks from both Magic Kingdom and Epcot, this 9,000+sf estate is like no other. Not only does the property cover over three acres and sit on a cul-de-sac, but it is the only lot in the community of Keene's Pointe surrounded on TWO sides by water, giving the owner the ultimate in privacy and seclusion. The home's floor-plan has been created in such a way to allow large gatherings in the main living areas, but also allows residents and guests to spread out to their own private areas and suites. The owners have made significant investments into the home since purchasing, including creating an incredible double master bath, which includes completely separate his and her bathrooms within the master suite. The home itself contains 6 bedrooms, 6 1/2 baths, theater, game room, bonus room, flex room, and an office overlooking the water. There is nothing more needed, nor left to the imagination. The exterior has one the most beautiful traditional designs you will find that includes a beautiful arched courtyard entry to a 4 car garage, multiple second story decks, outdoor living space, pool, spa, and magnificent covered dock with boat lift. The owners have also added an over-the-top summer kitchen with full bar and every outdoor cooking feature imaginable. There is no way to verbally describe this home properly. It must be seen and toured to be believed. $8,590,000 Active

6513 Rosella Court Windermere, Florida

6 Beds 7 Baths 9,089 SqFt 3.350 Acres

This stunning estate is the epitome of luxury Windermere lakefront living. Designed by legendary architect John Henry, this exquisite lakefront residence is perfectly positioned on Lake Down, part of the renowned Butler Chain of Lakes. Every inch of this stunning residence is built on a grand scale; from the six-car garage to the soaring 30-foot ceilings, the 12-seat home theater, a breakfast nook with seating for 10 and a private fitness center. This amazing estate boasts over 15,500 total square feet, including covered patios and outdoor living space. As you enter through the custom mahogany front doors, your eyes are immediately greeted by a two-story wall of windows with one-of-a-kind lake views. Owners will fall in love with the lavish master suite featuring a private sitting lounge and a magnificent spa bath. The kitchen is highlighted by top-of-the-line appliances, opulent granite surfaces, a huge center island and an amazing hidden pantry. Additional features include a private elevator, personal sauna, yoga/meditation room and a two-bedroom detached guesthouse. This home is all about luxury, convenience and lifestyle. While sitting on the covered lanai, peacefully gazing at the water, you will feel like you have left the city while you are actually just minutes from fine dining, incredible shopping and all of Central Florida's amazing theme parks $7,959,000 Active

5020 Down Point Lane Windermere, Florida

8 Beds 8 Baths 9,621 SqFt 2.010 Acres

Spectacular Tuscan Modern Custom-Built estate is a once in a lifetime opportunity inspired by the Italian Renaissance. One of the most exclusive private golf and country club communities in the world offers an exquisite location within the main gates of the beautiful award-winning community of Isleworth golf and country club. A fabulous double acre location along the front nine of Isleworth’s renowned championship golf course overlooking hole #3. The expansive estate showcases more than 12,500 square feet of living space. Beautifully updated and maintained, the residence displays double iron doors opening to a covered front entry/Porte Cochere, an extravagant fountain with a circular driveway. Upon entering the home, you are encountered with the stone and curved staircase and an exquisite, vaulted ceiling. The living room features a large, curved window through which professionally manicured gardens are viewed. The home features luxurious custom cabinets and exquisite crown moldings. The kitchen boasts professional appliances, granite countertops, a work island, and a beautiful accented high ceiling with direct access to the casual dining nook and formal dining room with a built-in hand-carved stone bar. Adjacent to the bar is a convenient wine cellar. The owner’s suite on the main level features dual spacious closets, access to the lanai, a luxurious bath with double vanities, a walk-in shower, an exquisite tub surrounded by stone columns, custom window treatments, and an elegant chandelier. The Home Theater resembles an old Hollywood vintage cinema with classic decorative moldings. The theater is part of the home’s game wing, including a billiard room, and an acoustically treated music recording studio. The intriguing design of an outdoor theater is an unusual twist that demonstrates this home’s artistic vision. The enclosed screened in patio is an indoor paradise including a Spa/Pool, descending movie screen, a stone fireplace, outdoor kitchen, and a cozy sitting area protected from the rain. Additional features include, Lutron HomeWorks, State-of-the-art Control4 Home automation system, an elevator, extra laundry room on the second floor, and an oversize six car garage. The property has a separate two-bedroom guest house and a second private patio above the cottage to complement the main home allowing privacy from the main home for your guests. $7,900,000 Active

5139 Isleworth Country Club Drive Windermere, Florida

7 Beds 8 Baths 13,973 SqFt 1.920 Acres

Stunning water views and **captivating sunsets** will take your breath away at this exquisite lakefront Estate. Perfectly situated on the shores of Lake Butler and the 15th hole of Isleworth's prestigious championship golf course you will enjoy 150 feet of lake frontage of the famed Butler Chain of Lakes. Inside, you will see what truly elevates this home. Distinctive details, an array of updated and amazing finishes and three magnificent floors with spaces for everyone in the family. On the main level: a gracious two-story foyer opens to an abundance of natural light and **unencumbered views of the lake** from each room. Striking chandeliers, a massive stone fireplace and private balcony complete the living room. A designer gourmet kitchen, complete with a large center island and luxury appliances such as Sub-Zero, Wolf and Bosch opens to the family room, dining room and breakfast nook overlooking long range water views. A butler's bar and laundry including a pet washing station complete this side of the main floor. Private and grand, the owner’s suite includes a **sitting room and balcony to watch the sunsets**. A hotel-rivaling bath with a back-lit granite jetted tub and truly impressive custom designed master closet are sure to please. The 2nd story offers the remaining 5 full bedroom suites including a **separate guest/in law’s wing** accessible by a half flight of stairs or entrance from the home’s PRIVATE ELEVATOR. Separated from the rest of the bedroom suites it includes a large private bedroom suite with standing shower and kitchenette. When it's time to truly relax and unwind, venture to the lower level which features every fun space imaginable: a GYM, overlooking the lake, bonus/recreation room, MOVIE ROOM with snack and beverage bar, WINE CELLAR and spectacular BILLIARD and CARD ROOM with FULL BAR . If this is not enough and you need to practice your golf swing enjoy the private GOLF SIMULATOR ROOM. Outside, enjoy the beautiful and **serene pool and spa**. If water sports or fishing is on the agenda the **private covered boat dock** has lifts to accommodates a boat and 2 jet skis. Take advantage of the more than 4,700 acres of 11 pristine interconnected lakes of the Butler Chain. All of this is located behind the manned gates of Isleworth, offering one of the most exclusive and private clubs and golf courses in the world and is known not only for its exclusivity but also its stellar service. Conveniently located in the Town of Windermere offering small town charm, weekly farmer’s markets and seasonal events yet minutes from world class shopping, dining and the theme parks. You can be at the airport in 20 minutes or the beach in just under an hour! Call today for a private tour! $7,775,000 Active

9832 Laurel Valley Drive Windermere, Florida

6 Beds 10 Baths 11,100 SqFt 0.700 Acres

Pre-Construction. To be built. Rare, Exclusive Lakefront property in Windermere, Florida. Front and rear water views! Gated community with only three home sites. TWO OPTIONS exist for this specific home site. Land Purchase at 2.895M or Pre-Construction Home at 7.5M. Herein lies an opportunity like no other to build your dream home on 6.82 acres of LAKEFRONT property in Windermere, FL. Shoreline comprising 524 feet fronting Lake Down on the Butler Chain of Lakes. Brand new developed privacy wall being erected fronting Maguire road. Privacy landscaping North of access road. Two newly added large retention pond fountains bring this property to life. The space directly south and directly west of the water feature pond presents any buyer with a unique opportunity to incorporate a golf-cart path for enjoying an added vineyard, garden, or outdoor recreation and entertainment area. New unmanned gate at entrance to be built. Come home to your piece of paradise in Central Florida. Live the “Lake Life” and enjoy over 5,000 acres of natural spring fed water by boat, paddle board, kayak, or jet ski.   With the plans and permits now in hand for a one of a kind 8,446 sq ft custom build, choose from an array of finishes to fit your aesthetic needs, or opt for pre-selected design finishes from the renowned designer Marc Michaels. Call to set up an appointment to build your dream lakefront home! Our team of real estate advisors will gladly assist! $7,500,000 Pending

10988 Down Yonder Lane Windermere, Florida

4 Beds 6 Baths 8,446 SqFt 6.820 Acres

Pre-Construction. To be built. Where Art Meets Architecture! Build your Custom Dream Home with state of the art energy efficiency engineering in the tranquility of the sought after Town of Windermere. Surrounded by the Butler Chain of Lakes. Award winning architects, JWB, and award winning builder, William Edward Construction. Per builder, lot can support a 10,000 - 15,000 square foot custom home. Price will vary as applicable. $7,500,000 Active

11035 Schooner Way Windermere, Florida

7 Beds 7 Baths 15,000 SqFt 1.050 Acres

This exquisite French chateau offers a prime location along the shores of Lake Bessie within the renowned Isleworth Golf & Country Club. Elegantly situated with a backdrop of water views, the expansive estate spans 12,353 square feet of living space across three levels, with luxury finishes. A circular drive and lovely custom French doors reveal a grand two-story foyer with a spiral tower staircase and captivating views toward the formal living room where floor-to-ceiling stacked picture windows perfectly frame the lake views. Beyond the formal dining room equipped with a private bar, the spacious kitchen boasts a warm mix of custom cabinetry and smooth granite, with appliances by Miele and Wolf—all overlooking a large family room with built-in media center and access to the terrace with motorized screens. The seven bedrooms within the home are generous in size, including the main owner’s suite complete with a sitting area, lake views, a bath and a two-story closet leading to the lower level. Perfect for entertaining, this recreational space within the home boasts a custom home theater, spacious game room, a temperature-controlled wine room, poker room, a guest suite with a sitting room and full bath, an elevator and direct access to the seven-car garage. The impeccable grounds take full advantage of the lakefront setting with an open-air pool and spa; ample deck space for lounging in the sun; a screened, covered terrace with summer kitchen; and a dedicated boat dock. Gracious lakefront living at its' finest! $7,435,000 Pending

5018 Latrobe Drive Windermere, Florida

7 Beds 10 Baths 12,353 SqFt 0.670 Acres

Majestic Lake Butler lakefront, Sunset views, Disney fireworks and the 15th hole of Isleworth's renowned championship golf course. As far as location goes, this home has it all. Breathtaking staircases, open floor plan and 2 story, direct lake views throughout the main floor. This one is a must see $7,000,000 Active

9838 Laurel Valley Drive Windermere, Florida

5 Beds 9 Baths 10,843 SqFt 0.540 Acres

UNIQUE ESTATE HOME SET ON 300 FEET OF LAKE BUTLER SHORELINE WITH 300’ SEAWALL. This private, gated lakefront home is set on 2.4 acres in old Windermere, with over 6,500 SF heated and over 10,600 SF covered and under roof; 5 bedrooms, 6.5 bathrooms, a resort style pool overlooking serene Lake Butler. CALLING ALL CAR COLLECTOR AND BOATING ENTHUSIASTS! This home has all of your needs covered with a 5-car garage and 2-car porte-cochere, plus 500-gallon fuel tank and 1000-gallon diesel tank with ability to fuel on the water or in your motor court - a feature you won't find at any other home on the Butler Chain. The “grandfathered” extra wide dock & boathouse features a sun deck, one boat slip and 2 jet ski with electric hoists. There is also a boathouse with bathroom and storage. The previous owner received Orange County approval for a future on-site guesthouse. Windermere is “The Town Among the Lakes,” and is known for its gorgeous estate homes, historic downtown featuring shops, dining, weekly farmer’s market, and excellent schools. Don’t miss this opportunity to own a large slice of Florida Paradise on the famed Lake Butler, which is a rare opportunity. Book your private tour today! $6,995,000 Active

11940 Lake Butler Boulevard Windermere, Florida

5 Beds 7 Baths 6,549 SqFt 2.410 Acres

Set within one of the most coveted streets in all of Windermere, this Mediterranean contemporary masterpiece combines grandeur and elegance for your enjoyment of living. Spanning over 5,600 square feet of living space and resting on a 1.09 acre lakefront lot, this estate is the quintessential dwelling place for life in 2022. Upon entering, an impressive two-story foyer and formal living space greet you and invite you in. From the very first step through the front door, you’ll notice that you’re standing on a piece of art. A custom SICIS Italian glass and metal mosaic adorns the floor and sets the tone for the entire experience. Revel in the breathtaking views of your resort-style pool and spa, overlooking the Wauseon Bay through your 650-gallon floating arched saltwater fish tank. The formal dining room features a custom tufted leather wall with handmade panels and bronze nail heads. It is complemented by beautiful crushed stone wallpaper and crowned with a dining dome showcasing another custom SICIS mosaic inset. The formal living room also displays a remarkable sculpted and carved paneled wall accentuated with ambient lighting. Continue your journey through the first floor to find your incredible gourmet kitchen accompanied with a wet bar, wine fridge, oversized pantry with a custom swinging door, Wolf and Sub-Zero appliance package, quartz countertops, custom cabinetry and two Swarovski Crystal Empire pendants illuminating the space perfectly. Sharing this wonderful space is your chic living room boasting mother-of-pearl wallpaper and an extraordinary fireplace wrapped with artistic wall panels designed by Alex Turco. The master bedroom resides downstairs and beckons you with its regal en suite, Christopher Guy lighting, separate dual vanities, standalone soaking tub and a striking Schonbek Da Vinci chandelier adorns the owner’s bath ceiling. Adjacent to the temperature-controlled wine cellar, you will find a first-floor laundry room with ample storage and an additional separate bedroom and full bath. A modern glass platinum stairway leads you to your second floor and continues to unfold a 195-square-foot clad wall with custom copper patinated iron finishes. This home also features a residential elevator finished with wood paneling interior and a stainless steel SICIS tile floor. The private cinema is unmatched and features eucalyptus wood custom millwork, a glass bar top with LED lights, Busby cabinetry, ample storage, Sub-Zero refrigerator, two under-counter wine refrigerators and seating for 10. All of this is crowned with a starry sky that envelops this magnificent space. Continue on the second floor to the home office with elegant custom wooden cabinetry displaying a double-sided fish tank that looks through to the game room. Soak up the picturesque Florida lake sunrises on your expansive private balcony overlayed with AstroTurf and enclosed with glass railing. Upstairs you also will find two additional bedrooms, three full baths and an additional laundry room, providing a more comfortable living space for your family or guests. Enjoy the lake life with a double-deck boathouse, summer kitchen and an abundance of space that exemplifies the epitome of Central Florida living. Auto enthusiasts benefit from the three-car air-conditioned garage with RaceDeck tile floors and additional custom storage system. An exclusive sanctuary, this home represents a refined, opulent lifestyle inside and out. $6,495,000 Active

801 W 2Nd Avenue Windermere, Florida

5 Beds 6 Baths 5,639 SqFt 1.090 Acres

Exquisite Mediterranean masterpiece, located in the 24-hour guard-gated community of Lake Butler Sound. This stunning residence features over 10,000 square feet of luxury living space and is perfectly positioned along the shores of Lake Butler on the famed Butler Chain of Lakes. This privately gated compound includes a resort pool with rock waterfalls, a lazy river, hot tub, summer kitchen and an outdoor living room with a gas fireplace. As you step through the front doors, your eyes are immediately greeted by soaring two-story ceilings and a wall of arched windows overlooking the pool and lake. Luxury and elegance resonate throughout the home with exquisite details that are truly second to none. The gourmet kitchen features a massive center island, top-of-the-line appliances, a double Sub-Zero refrigerator and a hidden pantry. The primary suite features a separate sitting area, two massive closets with custom cabinetry, and a spa bath with exquisite marble and onyx tile, a jetted tub, and oversized walk-in shower. There is also a first-floor home theater, massive game room, private wine cellar, fitness room and a home office/library. On the second floor, you will find a large outdoor balcony and three additional bedrooms, each of which would be considered an owner’s suite in any other home. With over 432 feet of shoreline and a private boat dock with a boat lift, there is sure to be endless hours of fun on the water. The car enthusiast will love the expansive motor court with a four-car garage and for the tech aficionado, the home is fitted with the state-of-the-art technology and home automation. This former celebrity-owned home is located just minutes from fine dining, world-class shopping and all of the area theme parks, the location of this spectacular residence simply can’t be beaten. $6,450,000 Active

11049 Bridge House Road Windermere, Florida

5 Beds 8 Baths 10,112 SqFt 2.900 Acres

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