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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 lakefront property with meticulously manicured grounds, this walled and gated compound includes apprx 614 feet of pristine lake frontage 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 nightly fireworks displays from Walt Disney World®. 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. $24,995,000 Active

9508 Windy Ridge Road Windermere, Florida

7 Beds 16 Baths 29,739 SqFt 18.170 Acres

Stunning modern masterpiece situated in Windermere's Reserve at Lake Butler Sound's most coveted 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

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. Per builder, lot can support a 10,000 - 15,000 square foot custom home. Price will vary as applicable. Possible assemblage with adjacent lot making it 2 acres. $8,250,000 Active

11035 Schooner Way Windermere, Florida

7 Beds 7 Baths 15,000 SqFt 1.050 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! $8,250,000 Active

11940 Lake Butler Boulevard Windermere, Florida

5 Beds 7 Baths 6,549 SqFt 2.410 Acres

Lease Purchase OPPORTUNITY! Love it or Lease it Rent to Own Luxury Home. Here is the opportunity to do a lease purchase on a Luxury Home. Incredible gated community with security and renowned fame. 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 stunning back-lit onyx 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. Land Purchase at 2.795M or Pre-Construction Home at 7.5M Rare, Exclusive Lakefront property in Windermere, Florida. Front and rear water views! Gated community with only three home sites. 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. 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 currently being installed. 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. 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.   Call to set up an appointment to build your dream lakefront home! Our team of real estate advisors will gladly assist! $7,500,000 Active

10988 Down Yonder Lane Windermere, Florida

4 Beds 6 Baths 8,446 SqFt 6.820 Acres

Windermere - Lakefront - Butler Chain of Lakes, Lake Tibet - Keenes Pointe - 24 Hr Guard Gated Golf Course Community... Explore this Stonebridge Custom Homes, 6 bedroom, 8 bathroom Estate, boasting more than 10,000 square feet of Resort Style Entertainment, Solitude, and an abundance of Luxury Finishes. As you approach the estate, pause and take in the handcrafted stonework and manicured grounds with fountain and beautiful vines reminiscent of European architecture. As you enter the grand atrium you will be drawn into the glass wall showcasing the spectacular Florida Pines along the lakefront. The interior features a large theater, an adjacent full and professional bar, which is just steps from the lakeside outdoor space with two swimming pools, spa, enclosed grotto behind flowing waterfalls, a water slide, fountains, and abundant lanai living. The outdoor kitchen, dining & living space boasts a fireplace, with optimal privacy, overlooking the lush landscape and lake. The professionally equipped main kitchen with butler pantry and wine cellar will accommodate large groups while still offering quaint family time in the bonus games room with billiard/snooker, table tennis and media seating area. The master suite is on the first floor, with private dressing room and is accompanied by a large private executive office with separate screened lanai. The master bathroom includes indoor and outdoor showers and jetted tub. A second floor private owners lounge with balcony view of lake Tibet and the evening fireworks display at Disney World are all contained in the owners wing of the house. Every bedroom is ensuite and very spacious. Bedroom 2 is on the first floor. Bedrooms 3,4,5 & 6 are on the second floor. Dining Room, Wine Cellar, and Library are all centralized to the main atrium and kitchen facilities. Enjoy quiet evenings in the library by the fire, or musical entertainment in the formal living rooms showcasing the swimming pools and the long view down the private boat dock with patio space and a lift designed for large heavy modern surf boats or cruisers as well as dual jet ski lifts. This home offers the luxurious style and space with a warm inviting ambiance not found in many estates of this stature. Keene's Point offers the private Golden Bear Club Golf Course, Restaurant, Tennis, Fitness, Pool and many playground park areas throughout. Windermere is nestled among the lakes and trees, with a small home town feel and has restaurants, cafe's, boutique shopping and many community events such as Farmers Market, Art Festivals, Food Truck Night, Golf Cart Christmas Parade, Light up Windermere, and Windermere Run Among the Lakes 10k. Furnishings available. Schedule your private virtual or in person viewing today. $7,495,000 Active

6507 Rosella Court Windermere, Florida

6 Beds 8 Baths 10,485 SqFt 2.190 Acres

Pre-Construction. To be built. Featuring an exceptional setting along the shores of beautiful Lake Bessie with gorgeous sunset views, this five-bedroom estate will be built on a pristine 0.67-acre home site within the renowned Isleworth Golf & Country Club. Leading custom luxury home builder Stonebridge Homes has partnered with Design Specifications interior design firm to present an ultra-modern estate of more than 7,600 square feet of living space featuring an array of chic and beautiful living spaces. Stunning white large-format porcelain floors will complement the oversized windows and all-glass railings both inside and out, setting the tone for modernity and sophistication throughout. Interior highlights will include formal living and dining rooms, each with two-story ceilings; an expansive main-level owner’s suite; a second owner’s suite on the upper level; a spacious, modern kitchen with a glass-enclosed, temperature-controlled wine storage; a game room; study; upper-level balcony; an elevator; four-car garage; and more. For seamless and beautiful indoor-outdoor living, the expansive lakefront terrace will showcase a sparkling pool, a custom fire pit, summer kitchen, plenty of lounging areas and a swinging daybed creating a luxurious outdoor haven overlooking spectacular lake and sunset views. $7,388,000 Active

9736 Chestnut Ridge Drive Windermere, Florida

5 Beds 7 Baths 7,625 SqFt 0.670 Acres

Pre-Construction. To be built. Your contemporary work of art awaits. Located in the Town of Windermere on the famed Lake Butler Blvd. is a beautiful 1.2-acre plot of land just waiting for this stunning two-story masterpiece. This custom estate home will be over 14,000 SF of luxury living and entertaining, with six bedrooms, and nine bathrooms. There will be three primary suites, with one located on the first floor and the other three upstairs. Each of the bedrooms will have en-suite bathrooms and private balconies. The main floor primary suite is stunning and features dual walk-in closets, sauna, and your personal Turkish Hammam. The guest suite features an expansive outdoor entertainment deck with lake water views. The entertaining possibilities are endless with a custom game room on the main floor, state of the art, 14-seat theatre room upstairs, and over 1,000 SF of outdoor living with summer kitchen overlooking your personal pool & spa paradise. Who needs the fountains of Bellagio when you have your own custom water and fire features displaying the impeccable landscape and backyard oasis? This custom estate home to be built by Supreme International Construction, will be solid concrete and steel construction of only the finest materials. All of the finishes will be high-level showroom finishes of your choice. Additional features include a glass elevator with an elevated floating catwalk, elevated great room, office/library, high ceilings on both floors, 5-car garage, water fountain, views of Lake Butler, and access to the Town of Windermere resident boat ramp. If you are looking for luxury style living, this is it! Contact us today. $7,035,000 Active

11947 Lake Butler Boulevard Windermere, Florida

6 Beds 9 Baths 14,364 SqFt 1.200 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

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 $6,750,000 Active

5020 Down Point Lane Windermere, Florida

8 Beds 8 Baths 9,621 SqFt 2.010 Acres

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