Properties For Sale in Windermere

Presenting Windy Ridge Estate on 18 gated acres with 614 feet of pristine frontage on Lake Down, Butler Chain of Lakes. Manicured grounds, panoramic water views, and over 50,000 SF across multiple structures create an unrivaled lakefront compound. The walled entry opens to a grand foyer with a f...

Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere’s largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 feet of lake frontage, a private island with moat and drawbridge, sandy beaches, two story double...

One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry Irwin and built by Ballard Construction, with inte...

Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, craftsmanship, and quiet luxury. European-inspired stonework, dramatic gabled rooflines, and a custom metal arched front door se...

Experience luxury lakefront living on a grand scale in this custom-built Modern Mediterranean estate on Lake Tibet, part of the pristine Butler Chain of Lakes. The three-story residence spans 9,571 square feet of living space on over 2.2 acres in the guard-gated community of Keene’s Pointe in sou...

Luxury living perfectly positioned along the 6th fairway in the world-renowned guard-gated community of Isleworth. This exceptional estate offers over 6,900 square feet of completely remodeled space which includes over 2,400 square foot addition upstairs thoughtfully reimagined by acclaimed arch...

Luxury Living at its finest in one of Windermere's most unique Waterfront properties, with 2+ acres in the exclusive Keene's Pointe community. Soak up the Florida sunshine in the very private garden oasis boasting 2 Resort Style pools with waterfalls, grotto and waterslide, outdoor kitchen and fi...

Under Construction. Brand New Construction in the Heart of Downtown Windermere – Currently Under Construction! Walking distance to downtown events, the farmers market, food trucks, and the local brewery. Historic Windermere is golf cart friendly and known for its outdoor lifestyle with parks, ...

One or more photo(s) has been virtually staged. Presenting a newly remodeled luxury estate ideally positioned along Isleworth’s renowned championship golf course, showcasing stunning views of the signature 3rd hole. This exceptional residence offers approximately 4739 square feet of refined livin...

Discover “Bella Olivia”: a grand mediterranean estate perched high above Lake Olivia showcasing sweeping lake views, private gates, and an expansive luxury residence spanning over 8,900 square feet of living space across 7 bedrooms, including two primary suites, two guest apartments, garage space...

Within the gates of the Waterstone community, this exceptional lakefront estate offers approximately 5,895 square feet of refined living space, seamlessly blending modern elegance with timeless sophistication. The thoughtfully designed floor plan features five bedrooms, five full bathrooms, and t...

Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned on Lake Burden within the exclusive gated community of Casa Del Lago in Windermere. This elegant two-story residence combines refined design, functionality, and breathtaking pa...

Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction | To Be Built | Designed for Unparalleled Luxury Discover an extraordinary opportunity to own a masterfully designed luxury residence in this Windermere community. This exquisite estate, crafted by the renowned Supreme...

Welcome to luxury living in the guarded, gated community of Waterstone in Windermere, Florida. This exceptional residence at 6219 Tiroco Way blends elegance, comfort, and modern efficiency, featuring solar power and an impressive floor plan designed for both everyday living and entertaining. The...

Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafs, parks, tennis courts, and yea...

Under contract-accepting backup offers. Now it's your turn to live on the 18th hole of the Golden Bear Club golf course in a fully updated custom home, located on one of the most desirable streets in Keene's Pointe. This house with a timeless design inside and out, has five bedrooms (two down and...

Experience elevated lakefront living in this one-of-a-kind estate, offering breathtaking views of Lake Bessie and unforgettable Florida sunsets. A private gated entry welcomes you to this exceptional residence, featuring 3 bedrooms and 3.5 bathrooms, plus a private in-law suite with its own full...

Looking for a move-in ready lakefront custom home in Windermere? Then look no further. This 6 bedroom, 4 full bath home with huge bonus room, pool and spa, sits on tranquil Little Lake Sawyer. With the lagoon style pool and enormous lot overlooking your own private dock, the backyard will become ...

Luxury Lakefront Home in Downtown Windermere. New Price - No HOA - Private Lake Bessie. Now offered at a newly adjusted price, this exceptional luxury lakefront home in Windermere, Florida presents one of the most compelling waterfront opportunities currently available in Downtown Windermere.If y...

Discover the perfect blend of elegance, comfort, and modern convenience in this exceptional 5-bedroom, 3.5-bathroom home in the highly sought-after Windermere Isle community. ENJOY NIGHTLY DISNEY FIREWORKS FROM THE FRONT YARD OR FROM THE UPSTAIRS FRONT BEDROOMS. A charming covered front porch inv...

Welcome to an exceptional opportunity in one of Central Florida's most sought-after areas. This ginormous 4 bedroom, 2.5 bath, two story home offers 2,947 square feet of versatile living space designed for comfort, entertaining, and everyday luxury. The layout is ideal, featuring a private den/of...

Under contract-accepting backup offers. Brand New Roof Just Installed!!! Step inside this home from anywhere! To experience a fully immersive walk-through of this home click on the Video or Virtual Tour button on this page. Nestled within the highly desirable Preston Square community, this elegan...