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

Nestled on 18 acres of pristine lakefront property, this exceptional estate offers a sanctuary of unparalleled beauty. With approximately 627 feet of frontage on Lake Down in the coveted Butler Chain of Lakes,
it presents breathtaking panoramic views and the added enchantment of nightly fireworks displays from Walt Disney World®. Behind walled and gated grounds, this expansive compound allows for limitless development possibilities. Expand and build additional structures, subdivide, or create a private family enclave—the choice is yours.
The primary residence, blending classic Georgian architecture with modern amenities, embodies nearly 50,000 square feet of heightened luxury.
Every detail exudes timeless elegance, from the incredible entryway to the mahogany-lined living room overlooking the water.
With one of two owner's suites on the main level, along with a versatile space that can serve as a library lounge or sixth-bedroom suite, this estate offers flexibility.
As is appropriate for an estate of this level of grandeur, access the upper floors with your choice of one of two elegant staircases, or your own private Thyssenkrupp elevator. Upstairs, discover four expansive bedroom suites, including the lavish main owner's retreat. The 85-foot parlor with 20-foot ceilings, bookshelves, and a wet bar is ideal for hosting gatherings surrounded by truly timeless estate design that blends the classic and the contemporary.
A screened porch captures the spectacular southern lakefront views, including the nightly fireworks displays from Walt Disney World®, adding a touch of magic.
A grand rustic lodge connected by a breezeway offers entertainment possibilities, while a Junior Olympic pool and spa await outdoor relaxation.
A Garage for 50+ cars offers your the opportunity to pursue and cultivate your dream collection
The gourmet kitchen is a chef's dream, featuring top-of-the-line appliances including a salamander, double convection ovens, a commercial ice maker, and a commercial refrigerator and freezer.
The kitchen ensures that this home is both your palace and a spectacular venue for hosting everything from an intimate gathering to a showcase gala.
Additional features include storage space, staff quarters, a patio area, and a paneled garage with a separate office and guest apartment. Situated in a highly sought-after area of Central Florida, this extraordinary estate offers an enviable lakefront lifestyle. Nearby amenities, schools, and easy access to major routes make it a rare opportunity for refined living.
You can pay $3,750,000 cash with 50% seller financing for a 1/4 partnership interest (3-month ownership and use) for a set 8-year period with full-service management and concierge services, and with the option to leverage the asset by submitting time in the home to the THIRDHOME exchange to exchange for one of 15,000 luxury homes in 100 different countries. Owner financing up to 50% with negotiated terms. Furniture is not including the price. See the link below for the video:
https://youtu.be/MpU1bVdW_ZQ

$30,000,000 Active

9508 Windy Ridge Road Windermere, Florida

7 Beds 16 Baths 29,739 SqFt 18.170 Acres

Welcome to 6004 Cartmel Lane, a truly magnificent lakefront estate in highly coveted Windermere, Central Florida. Nestled on the pristine shores of Lake Butler (largest on the Butler Chain of Lakes) and ideally situated on a secluded cul-de-sac within the exclusive 24/7 guard-gated community of The Reserve of Lake Butler Sound, this awe-inspiring architectural masterpiece sits on a double lot of 4.78 acres and with over 540 feet of water frontage, provides both scenic beauty and privacy. Comprised of 20,240 sqft under air (30,949 gross), with high end features abound, this stunning and unique residence is designed to take full advantage of the Florida lifestyle seamlessly blending the indoor with the outdoor. As soon as you step inside the entry way, the double heighted soaring ceilings of the foyer and formal lounge immediately sets the scene of grandeur. The gourmet kitchen is a chef’s dream with large islands, walk-in oversized pantry, high-end appliances, and breakfast bar seating enhanced by a full caterers’ kitchen (with separate access). The interior amenities include a two-lane bowling alley, sports bar, karaoke, home theater, music loft, games arcade, recreation (or meditation room), fully equipped fitness gym and sauna & steam room. Also complementing the residence is a home office, a ventilated cigar lounge & temperature-controlled wine vault, multiple casual living and lavish entertaining lounge spaces and a formal dining room with additional independent dining area. The outdoor area highlights include a spectacular resort style saltwater pool with a spa, a grotto and a slide as well as swim up hibachi grill & bar, flood lit tennis and basketball court, a sand volleyball court, a playhouse with power, splashpad and zip line, vegetable garden, two firepit areas, two outdoor kitchens, a well-equipped boat dock with upper sun deck including paddleboard/canoe launch and lush mature landscaped gardens. There are a total of 9 bedrooms and 13 full and 4 half bathrooms. The luxurious owner’s suite is a dedicated wing set out on the first level and is a private paradise oasis consisting of an expansive bedroom with cozy retreat/sitting area, convenient coffee bar, two separate showers and two separate toilets, a large outdoor shower, a huge two-storey wardrobe, a beauty/hair salon, its own laundry room plus a recreational/exercise room with dual access. There are two themed bedrooms which are on either side of a distinguished bespoke two-storey playroom and two further individual guest ensuite bedrooms. There are two separate guest/staff quarters - each has two individual bedrooms and ensuite bathrooms, a living area as well as a kitchenette and dedicated outdoor terrace. Additional features include a residential elevator, multiple fireplaces, wet bars, laundry rooms, state of the art technology, illumination & security, ample storage space and multiple balconies with sweeping views to avail of the breathtaking sights and spectacular sunsets. There is extensive garage space for 8 vehicles with an additional motor court and ample bay parking areas. Strategically located within minutes of top-rated public and private schools, award-winning shopping and dining, world-renowned theme parks and attractions as well as having easy access to major highways and Orlando International Airport.

$30,000,000 Active

6004 Cartmel Lane Windermere, Florida

9 Beds 17 Baths 20,240 SqFt 4.780 Acres

Sophisticated elegance masterfully packaged into a custom-crafted lakefront mansion built specifically for the ultimate sports enthusiast, situated behind the secured manned gates of Central Florida’s most exclusive address. Featuring a 6,060 square foot air-conditioned full-sized basketball court, this incredible Isleworth estate surpasses all expectations with state-of-the-art technology, chic modern styling, and epic recreational offerings. Recently built to the highest standards, this residence combines modern luxury with today’s demanding lifestyles. Encompassing nearly 15,000 square feet in size, including 6,060 for the basketball court, the other 9,000 square feet of living space spans formal and living areas, 5 bedrooms, 8 baths, exercise room with sauna, theater, office, recreation room, and two-story master closets, washer and dryer in master – plus hidden shoe and memorabilia closets. Offering sweeping sunset and nightly Disney fireworks views from its perch above Lake Blanche on the famed Butler Chain of Lakes, the setting is serene and peaceful. Outdoor living areas are generously appointed and include a summer kitchen with WOLF appliances inside and out plus retractable invisible screens. The sparkling swimming pool and spa deliver a refreshing private resort experience. Located within the gates of the 600-acre Isleworth community, surrounding the Butler Chain of Lakes, this residential enclave sets the standard of excellence for Central Florida living. On-site home services are available for a carefree lifestyle. Isleworth Golf and Country Club, which is located within the community, offers various membership opportunities, and is recognized as one of the Top 100 Platinum Clubs of the World offering the ultimate in amenities and concierge living. (Full-size basketball court could be easily converted into a show garage for car collectors.) Interior photos provided to qualified buyers.

$16,500,000 Active

9306 Blanche Cove Drive Windermere, Florida

5 Beds 8 Baths 14,856 SqFt 3.720 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

This stunning estate, complete with top-tier amenities and meticulously maintained to perfection, is a turnkey sale, inviting immediate occupancy and delight for its discerning new owner. The home is primed with all the essential features and adorned with tasteful furnishings, beautiful art, and notable pieces such as a Yamaha Baby Grand Disklavier Piano. Attention to detail is paramount, with no facet left unaddressed. The well-appointed theater, featuring an array of autographed Star Wars memorabilia, is a true testament to the estate's refinement. A recent renovation in March 2022 by Paradise Pools by Design has transformed the pool and spa into a pristine oasis. The home boasts a whole house generator, a comprehensive automation system with a Lutron Lighting System, Nuvo Sound System, and state-of-the-art security and alarm systems, all accessible via wireless controls for convenience. This seamless transition into a comfortable lifestyle is further enhanced by the captivating sunset views overlooking Lake Bessie and the 8th fairway of the esteemed Isleworth Golf and Country Club. This turnkey luxury estate offers a complete sanctuary ready for immediate enjoyment. Your personal belongings are the only missing piece in this extraordinary equation, as everything else stands poised and ready for its new residents.

$8,475,000 Active

5200 Isleworth Country Club Dr Windermere, Florida

5 Beds 8 Baths 9,482 SqFt 0.790 Acres

Welcome to this magnificent lakefront estate in the Isleworth Country Club Community. This exceptional property offers the epitome of luxury living, combining a classic Pellegrini Home with impeccable craftsmanship, and panoramic views. With 11,021 square feet of living space on an oversized 1.16 acre lot, this estate has an unparalleled level of grandeur and elegance.
Inside is a captivating grand dual staircase with a seamless open entry to views that blend the glamorous infinity pool into the pristine open lake. The open-concept floor plan allows for seamless flow between the spacious living areas, ideal for entertaining guests or simply enjoying time with family. The soaring ceilings, expansive windows, and skylights flood the interior with natural light, creating an airy and uplifting atmosphere.
The gourmet kitchen boasts top-of-the-line appliances, custom cabinetry, and a large center island that serves as a gathering point. Adjacent to the kitchen, the formal dining room provides an elegant space with a full bar for more intimate gatherings.
The estate features five generously-sized bedrooms, including a lavish primary suite that exudes tranquility and opulence. This includes a spa-like ensuite bathroom with a luxurious soaking tub, a spacious walk-in shower, and dual vanities. Each additional bedroom offers ample space, en-suite bathrooms, and walk-in closets, ensuring privacy and comfort for all residents.
Outdoors, the estate presents an oasis of relaxation and entertainment. The expansive backyard showcases a beautifully designed patio area for lounging or al fresco dining. With the backdrop of sweeping vistas, including breathtaking views of Lake Chase, there is a true sense of serenity and escape.
Additional features of this remarkable estate include a home office/library, a state-of-the-art media room, a fitness center, several bars and a spacious garage sufficient to hold a car collection.
Whether you seek tranquility, luxury, or both, this extraordinary residence delivers an unparalleled lifestyle that exceeds expectations.

$8,300,000 Active

6432 Deacon Circle Windermere, Florida

5 Beds 9 Baths 11,021 SqFt 1.160 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

Stunning lakefront home in the highly desired, gated/24 hour guarded community of Keene’s Pointe. This home was thoughtfully built by highly regarded custom home builder Goehring & Morgan. No detail was spared on this private 4-acre estate home located on Lake Tibet Butler of the famed Butler Chain of Lakes. From the moment you enter you are surrounded by elegant finishes, beautifully detailed ceilings and floors and luxurious decor. The functional floor plan offers 6 en-suite bedrooms - two on the first floor and three on the second floor and the first floor primary suite with spacious bath, walk-in closet and its own spiral staircase leading to the upstairs master retreat - currently used as a second closet, it can also be converted back to a library/office/den. Also on the first floor, you will find the formal living/dining room, a kitchen/family room combo, butler's pantry, one of two laundry rooms, a wine cellar and gym. The gym is located off the primary suite corridor and can also be converted to a 4th garage pleasing the car enthusiasts. Both the living and family rooms open up to the stunning covered lanai with fireplace and summer kitchen that leads to the stunning pool area with a beautiful view, gazebo, fire pit, sports court, and your own private dock that gives you access to the lake. The second floor also features a media/game room and spacious balcony, one of the many perfect places to relax and enjoy the lake view. Keene’s Pointe is also home to The Golden Bear Club a membership-only club featuring golf, tennis, fitness, dining and swimming. Among Windermere's best private and public schools and just minutes to shopping, restaurants, and world-famous theme parks!

$6,999,000 Active

6125 Grosvenor Shore Dr Windermere, Florida

6 Beds 7 Baths 8,037 SqFt 4 Acres

Welcome to this exquisite high-end luxury lakefront home at 6013 Greatwater Drive, located on a premium lot on a cul-de-sac in the exclusive, 24 hour guarded Keenes Pointe neighborhood of Windermere, Florida. This property boasts a prime location on Lake Tibet Butler, offering breathtaking views from most any room in the home, as well as unmatched tranquility.

Beyond your brick-paver circular driveway, you'll step inside the grand entrance and immediately notice the jaw-dropping attention to detail and superior craftsmanship throughout, adorned with high-end fixtures and architectural surprises at every turn. This stunning residence offers five bedrooms, each complete with their own California closets, providing ample storage space, organization, and a touch of luxury to every bedroom. Additionally, there are 5 full bathrooms and two half bathrooms, ensuring convenience and privacy for everyone. The impressive primary suite presents many unique features, including a natural gas fireplace, electric window shades, his and hers closets, as well as an exquisite ensuite bathroom.

The kitchen is a true culinary masterpiece, featuring top-of-the-line Wolf appliances, ensuring that every meal is prepared with precision and style. It even boasts "hidden" luxuries like the enormous Subzero refrigerator, dishwasher, warming drawer, ice maker and more. Two wet bars- one off the living room, and one in the game room complete the entertainment appeal of this prestigious home. Speaking of entertainment, this legacy property has taken it to the next level with a dedicated movie theater providing the ultimate cinematic experience right at home. The downstairs game room, complete with a bar and dedicated space for three TVs, is an ideal space for hosting gatherings and enjoying quality time with friends and family. Plus, it connects to the aw-inspiring screened-in outdoor summer kitchen and pool area overlooking the lake.

Outside, unwind in the waterfall accented infinity-edge saltwater pool, perfect for enjoying the Florida sunshine and cooling off on hot summer days. Adjacent to the pool, you'll find a luxurious saltwater spa, offering a serene retreat for relaxation and rejuvenation. The entire estate is enveloped in carefully curated Florida-friendly landscaping, creating a true Florida paradise that follows through all the way to your private dock. Two boat lifts allow for easy access to Lake Tibet Butler, just one of the pristine lakes on the Butler chain of lakes, making it a superb recreational destination.

Car enthusiasts will appreciate the four-plus car garage, providing ample space for vehicles and storage. There's even a designated golf-cart bay!
Keenes Pointe also boasts many of its own luxuries, including a private boat ramp and playground. Residents here also have the opportunity to join the Golden Bear Club, a private country club with world renowned designer golf course and luxury clubhouse.

Don't miss the opportunity to experience the true Florida lifestyle and luxury living at its finest in this exceptional lakefront home! Watch the virtual tours for a more in depth look at this fantastic estate!

$6,999,000 Active

6013 Greatwater Drive Windermere, Florida

5 Beds 7 Baths 7,607 SqFt 3.560 Acres

Spectacular modern property in the Beautiful gated community of Isleworth. Designed with a concrete structure, luxurious finishes, and numerous windows, this residence is bathed in natural light, creating a pleasant atmosphere. Security is paramount in this exclusive enclave, offering 24-hour protection and access to one of the state's premier golf clubs. Upon entering the community, prepare to be captivated by the imposing presence of the property, boasting over 10,000 square feet of architectural grandeur. This residence features multiple entrances, including a private suite with a discreet entrance for esteemed guests or beloved family members. Every corner of this property showcases high ceilings, including meticulously designed closets, emphasizing a commitment to a lifestyle of unparalleled elegance. The expansive pool gracefully envelops the exterior with outdoor shower and is complemented by a summer kitchen, creating a welcoming atmosphere synonymous with the charm of Florida living. The master suite, conveniently located on the first floor, includes a sauna and two direct accesses to the pool area, promising a perfect blend of comfort and luxury. The kitchen, designed with a fully modern open concept and adorned with top-tier luxury appliances, sets the stage for creating and savoring unforgettable moments. Prepare to be amazed by the luxurious features and impeccable finishes that define this residence, promising to exceed the expectations of even the most discerning individuals. Welcome.

$6,500,000 Active

5190 Latrobe Drive Windermere, Florida

5 Beds 7 Baths 7,191 SqFt 0.730 Acres

One or more photo(s) has been virtually staged. Under Construction. Stunning custom lakefront home located on Lake Down, one of the famed Butler Chain of Lakes in Windermere. This Element modern custom home offers a transitional 4 bedroom, 4 full and 2 half bath floor plan, with a two-story foyer. The first floor boasts an open and spacious great room, kitchen and dining room with unobstructed views of the lake in all directions. In addition, there is a spacious pantry, office, guest en-suite, laundry and storage, large game room and primary suite with spacious bathroom and walk-in closet. The second floor has a second game room/loft and two en-suites with panoramic views of the lake. Energy-efficient double pane windows and doors, decorative glass entry door, sliding and modern barn doors, tankless water heaters, spray foam insulation, multi-zone AC, detailed ceilings, quartz countertops, walk-in pantry, oversized built-in closets, Thermador appliances, seamless glass shower enclosure, and designer lighting complement this home. The resort-like lifestyle continues outdoors with the pool and spa, summer kitchen and outdoor fireplace under almost 1,500 sf of covered living space with retractable screens. This home is situated on 2.80 acres at the end of a private cul-de-sac with nearly 200 feet of seawall. Beautiful unobstructed lake and sunrise views and a premium landscape package. A split 4-car garage (2 on each side), and covered boat dock complete this stunning home. Located in Windermere, one of the most desired areas, with unspoiled panoramas of stately pine and oak trees, high elevation and eleven interconnecting lakes. Close to A-rated public schools, private schools, parks, town events and farmer's market, golf courses, expressways, restaurants, amenities and shopping, Disney World and Universal Studios. Call today for your private tour. The plan and specifications are subject to change at the owner/builder's discretion. Photos are builder renderings and may differ from actual floor plan or features.

$6,490,000 Active

10821 Bayshore Dr Windermere, Florida

4 Beds 6 Baths 5,275 SqFt 2.800 Acres

$6,299,000 Pending

11205 Bridge House Road Windermere, Florida

6 Beds 8 Baths 8,330 SqFt 1 Acres