Windermere Real Estate - TC Orlando Homes

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. Windermere is best whether you want to relax or play, this community has amenities for you to enjoy.

Windermere, FL Real Estate Statistics

Total Homes for Sale:	0
Avg Home Price	$0
Highest Home Price	$0
Lowest Home Price	$0

Windemere

default

windermere-fl-2

windermere-fl-3

windermere-fl-2

windermere-fl-3

Search Windermere, FL Listings By Price

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

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.)

$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 magnificent estate is located on the eighth fairway of the Isleworth Golf and Country Club golf course. Step through the front doors and be captivated by the grandeur of the foyer, soaring ceilings, intricate architectural details, and breathtaking views of the golf course and Lake Bessie. Highlights of the first floor are the gourmet chef's kitchen with its top-of-the-line appliances, custom cabinetry, center island, and well-equipped butler's pantry. Adjacent to the kitchen is a breakfast nook and comfortable family room open to a generous covered lanai overlooking the lake. Also located on the home's first level are the beautiful formal dining, living room, laundry room, wine room, and the lavish primary suite with large closets and a spa-like bath for peaceful rest and relaxation.

A grand staircase and convenient elevator provide access to the second-floor hosting three large ensuite bedrooms, a grand office with custom woodwork and built-ins, a movie theatre, and extra bonus spaces for exercise and storage options. Several of the upstairs rooms have balconies to capture the amazing views.

Outside, a sprawling backyard oasis awaits a stunning swimming pool, lush landscaping, and an outdoor kitchen ideal for al fresco dining and entertaining. A private two-story guesthouse with its own living room and loft bedroom round out this must-see estate.

$8,975,000 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

Lake Butler Luxurious Lakefront Estate - Exquisite Custom-Built Residence!

Welcome to an opulent lakefront estate that epitomizes luxury living. This magnificent custom-built home, graces an enviable lakefront lot, offering unparalleled beauty and sophistication. Right across the estate of Versailles with a 90,000-square-foot (8,400 m2) house. It is under construction at 6121 Kirkstone Lane, Windermere, Florida, in the gated community of Lake Butler Sound in Orange County, Florida, United States. Named and modeled after the Palace of Versailles in France, the completed project would be one of the largest single-family homes in the United States.

Crafted with meticulous attention to detail and utilizing only the finest materials, this residence exudes elegance and class. The awe-inspiring two-story formal living room showcases floor-to-ceiling windows that frame breathtaking views of the tranquil lake.

Unparalleled in its offerings, the property boasts an array of amenities, including a resort-style salt-water pool, a fully equipped boat house, an expansive car garage for car enthusiasts, a private elevator, and a state-of-the-art generator for uninterrupted comfort.

Entertainment takes center stage with a professionally equipped theater and a lakefront billiard/game room, complete with a fully stocked bar. The residence boasts 5 lavishly designed bedrooms, with a generously sized bonus room/flex space that can easily transform into a sixth bedroom.

The gourmet kitchen is a chef's delight, boasting top-of-the-line appliances and a seamless flow to the lakefront family room. The family room is adorned with magnificent engineered doors that effortlessly pocket into the walls, leading to an immense screened porch with a cozy fireplace and a sophisticated refreshment bar—ideal for hosting grand gatherings or enjoying private moments in a mesmerizing setting.

Ascend the exquisite front and rear staircases to discover a welcoming lounge area, three opulent bedroom suites, and a capacious bonus room catering to various needs. For added convenience, the home offers three distinct laundry areas, each equipped with state-of-the-art washer and dryer units.
Undeniably an aspirational property, this estate promises a luxurious lifestyle and an opportunity to build cherished family memories. Don't hesitate; act now and seize the chance to acquire this remarkable dream home on the serene shores of the lake Butler.

$7,900,000 Active

6120 Kirkstone Lane Windermere, Florida

6 Beds 8 Baths 6,972 SqFt 1.280 Acres

One or more photo(s) has been virtually staged. Pre-Construction. To be built. New Street name. New photos/renderings capturing the actual design finishes included in plans! ATTENTION future home buyers who wish to build new but want to avoid the 6-8 months it takes to design a home and have it approved by the governing authority: Permits and Plans are in hand and ready to go on this beauty. The Seller scrupulously designed this home because it was his intent to build his primary residence here! Natural, Earthy, Modern/Cabo Coastal themed home with contemporary finishes exemplifying a distinguished character and a timeless sense of style and taste. Moreover, there is NO HOA! This home site is situated in a planned residential development. See attached Declaration. Gated community with 3 total homesites. Private, Rare, Exclusive Lakefront property in Windermere, Florida. Front and rear water views! Herein lies an opportunity like no other to build your dream home on 6.82 acres of LAKEFRONT property in Windermere, FL. Shoreline comprising approximately 300 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 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 design group, 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!

$7,440,000 Active

10988 Down Park Lane Windermere, Florida

4 Beds 6 Baths 8,446 SqFt 6.820 Acres

This Jones- Clayton built masterpiece set behind the guarded gated entrance of Reserve at Lake Butler Sound will leave you speechless around every corner. This custom one-of-a-kind estate was painstakingly designed to deliver an extremely functional and adaptable floor plan for any buyers needs with the highest of finished gathered from around the world. 142 ft on the shores of coveted Lake Butler, the jewel of the famed Butler Chain of Lakes. Walk your own private nature trail to your large, covered boat dock granting you access to 13 interconnected lakes boasting over 5,000 acres of navigable fresh water to enjoy and explore. The curb appeal on this home is second to none with imported stone front facade to replicate famed Casa Feliz designed by James Gamble Rogers in Winter Park... with the signature turret, bell tower and expansive front balcony. The floor plan checks every box with 2 owners suites, 2 bonus rooms (one on each floor), dedicated home theatre, in-law suite with kitchenette and full bath and separate entrance, Private office/ command center above garage with separate entrance & private bath, 2 full laundry rooms (both with 2 washer & dryers) wine room, all oversized secondary bedrooms and of course a PRIVATE ELEVATOR. The finishes throughout the home are second to none with reclaimed over 100-year-old barn wood for the floors and just too much to list here. Dream kitchen with AGA stove and range, Miele coffee maker, countless SUB-ZERO fridges, freezer and drawers. Downstairs bonus room and additional fully equipped home theatre. Sonos and Creston throughout entire estate and whole home water filtration. Dream back yard to truly embrace the Florida Lifestyle with huge, covered lanai with summer kitchen, wood burning fireplace and remote screen wall giving access to the Saltwater pool with beach entry, water slide and rock waterfall. Custom sport court and putting green also in the fully fenced back yard. The real shining star of the property is the just renovated dock that meanders through the Lake Butler Nature Preserve to your covered boat dock giving you post card sunset views every day of the week as well as access to the most sought-after chain of lakes in Florida. This buffer gives you rare privacy from all the boaters on the chain, a very welcome side effect to this Conservation area, offering the lake life with privacy rarely granted with Lake Front living. Reserve of Lake Butler Sound is 24/7 guarded entry community boasting some of the nicest estates in Central Florida, including Americas Largest Estate, the famed Versailles. Sought after K-12 public school district and minutes from Windermere Preparatory School and Foundation School campuses. Just a few miles from Disney's gates, countless shopping and dining choices and under 25-minute commute to Downtown Orlando. This estate truly checks all your must haves with a timeless and flexible floor plan. One lucky buyer will be able to call this work of art their home. Call for your private showing. OWNER FINANCING IS ALSO AVAILABLE.

$7,250,000 Active

11019 Bridge House Road R Windermere, Florida

7 Beds 11 Baths 9,376 SqFt 2.950 Acres

Welcome to this marvelous lakefront home at the desirable Keene’s Pointe community! Built by highly regarded custom home builders Goehring & Morgan on a 4-acre lot, this monumental home will give you the most incredible experience of living! Its elegant finishes, cathedral ceilings and luxurious decor will amaze you. Home located on the Butler chain of Lakes, specifically on Lake Tibet connecting to 11 other crystal lakes through well maintained canals. It's a boat paradise!!!!
At the entrance, you are greeted by a beautiful green area, a meticulously treated garden, palm trees, a spacious patio and a majestic architectural design that will leave you speechless!
With a unique floor plan that includes 6 bedrooms and 7 bathrooms, including the master bedroom with its own spiral staircase leading to the upstairs master retreat, you will fall in love with each and every detail presented here.
On the first floor, you will find the formal living room, a kitchen/family room combo, plus a summer kitchen that leads to the stunning pool area with a terrific view and your own private deck that gives you access to the Tibet Butler Lake. The second floor also features a great balcony, one of the many perfect places to relax and enjoy this movie-like life.
Keene’s Pointe is a gated and 24h guarded community that offers a variety of amenities such a Clubhouse, golf course, seasonal events and water activities. Just minutes to shopping malls, restaurants, schools and world-famous theme parks! Words are not enough to describe this tremendous opportunity! Schedule your showing today!

$7,150,000 Active

6125 Grosvenor Shore Drive Windermere, Florida

6 Beds 7 Baths 8,287 SqFt 4 Acres

Windermere Lakefront on Butler Chain of Lakes in guard-gated Keene’s Pointe Neighborhood. Entertainer’s paradise featuring over 10,000 square feet of Mediterranean luxury, flex spaces, custom bar, movie room, game room, and wine cellar. Private, sweeping veranda with tongue-in-groove ceiling, sprawling pool and spa, outdoor fireplace, and summer kitchen. Breathtaking views of Lake Tibet and tree-lined walkway to covered boat dock. If you’re looking for heaven in the form of a home, you’ve found it.

From the moment you arrive at this Watson Custom Home, you’re immersed in opulence. Manicured grounds encase a brick paver driveway leading to stone-front Mediterranean-style architecture. Regal wood doors open to a light-filled foyer that spills into a spacious living room featuring an ornamental fireplace and picture windows overlooking the scenic backyard. On the left of the foyer, the study features custom wood and wrought iron doors, wood coffer ceiling, built-in bookcase, and wood paneling. On the opposite side, the spacious dining room offers an intricate tray ceiling, recessed wall niche, an abundance of natural light, and opens to the butler’s pantry. The custom wine cellar with refrigerator and ample storage lives in an alcove behind an arched entryway adorned with ornate wrought iron doors and painted Italian vines. The inviting kitchen is positioned at the back of the home and features gorgeous wood cabinetry, an oversized center island, tile backsplash, gas stove, sub zero refrigeration, and breakfast nook that opens to the family room. Featuring wood coffered ceilings and doors to the veranda, the family room opens to one of the three flex spaces. The space features coffered ceilings with wood beams, enormous picture window with lake views, and access to a custom bar. Tucked away behind the bar is an exciting theater room. The primary suite encompasses the entire left side of the home and features tray ceiling, a reading nook with fireplace, picture window overlooking the pool, and French doors leading to the veranda. There’s also a private, outdoor patio area with spa, fireplace, sauna, direct access to the home gym, and screened in ceiling providing open air views. The stately primary bath features tray ceilings, regal chandelier, oversized shower, and wood cabinetry. There’s an additional bedroom with ensuite on the first floor and four additional bedrooms with ensuites can be found on the second floor by way of an elegant wood and wrought iron staircase. Also upstairs is a large flex space and balcony overlooking magnificent views of moss-covered trees and a scenic walkway to the lake. With its private, pristine views, the veranda is the perfect space for festive gatherings or a peaceful morning cup of coffee or sunset cocktail. The fenced backyard offers more space to play, stunning views, and access to the lakefront walkway. With its four car garage, custom woodwork, travertine flooring, crown molding, and Mediterranean touches throughout, this home is a true private oasis and symbolizes perfection for those seeking grandeur, privacy, space, and views all wrapped into one. It doesn’t get much better than this one-of-a-kind, sparkling gem.

Keene’s Pointe is home to the the exclusive 250-acre, Jack Nicklaus Golf Course & Golden Bear Club with pool, fitness center, tennis center, Pointe 18 Grille, & a variety of community events & activities. (Golden Bear Club Golf & Social Memberships available for additional fee)

$6,500,000 Active

9139 Tibet Pointe Circle Windermere, Florida

6 Beds 9 Baths 10,341 SqFt 2.070 Acres

$6,450,000 Active

5518 Worsham Court Windermere, Florida

5 Beds 8 Baths 8,100 SqFt 0.990 Acres

Windermere, FL Area Real Estate Market Report