Windermere, FL Homes for Sale under $2,000,000

Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.As

Marcelo Brandao HOME N OFFICES INTERNATIONAL

Located within the prestigious gated community of Balmoral Estates, this spectacular 6-bedroom, 5.5-bath 4 car garage luxury estate sits on an expansive 3⁄4-acre homesite and has been completely renovated with exceptional custom upgrades throughout. From the moment you arrive, the property makes a striking impression with a brand-new circular paver driveway centered around a dramatic custom water

Ryan Rogers REAL BROKER, LLC

Set behind the gates of Windermere Club, this lakefront residence delivers everyday comfort with a resort-style backdrop on beautiful Lake Crescent. Offering 4 bedrooms and 3 baths, the home is designed for easy living and effortless entertaining, with bright, open gathering spaces that keep the water views front and center. At the heart of the home, the kitchen pairs generous prep space with a

Simon Simaan THE SIMON SIMAAN GROUP

Experience the Florida lifestyle in this stunning FULLY FURNISHED 5-Bed/4-Bath pool home on over 1/2-acre, with a welcoming open floor plan spanning 4,500 square feet, spectacular Theater Room, custom upgrades and designer accents throughout, and new dual-zoned AC system in August 2025 including Nest smart thermostat. Situated across from the community park and tennis on one of the best

Frank Ferrell FERRELL REALTY, INC.

Nestled among the Butler Chain of Lakes in the charming Town of Windermere, this 4-bedroom, 3-bath pool home offers the perfect blend of comfort, space, and tranquility. Located within the sought-after Marina Bay community, the home features a warm and inviting atmosphere, a spacious floor plan designed for everyday living and entertaining, and an oversized lot that provides plenty of room to

W. Channing Harrison LAKESIDE REALTY WINDERMERE INC

MAJOR PRICE IMPROVEMENT!!! Welcome to a truly exceptional custom home in Keene's Pointe, one of Windermere’s most sought-after guard-gated communities. Built by W. J. Sauerwine and set on a beautifully landscaped .43-acre homesite with mature oak trees, this residence offers a rare combination of privacy, thoughtful design, and extensive modern upgrades.This 4-bedroom plus office, 4-bath home

Donna Calhoun KELLER WILLIAMS CLASSIC

Discover an exceptional expression of modern luxury in the heart of Windermere. Welcome to 11051 Hawkshead Court, gracefully positioned within the prestigious Reserve at Lake Butler Sound—an exclusive guard-gated enclave renowned for its elegance, privacy, and lakefront lifestyle. Set on an expansive half-acre homesite at the end of a cul-de-sac, this fully reimagined contemporary estate offers a

Ken Pozek REAL BROKER, LLC

Rare opportunity to own one of the most private lakefront settings on Lake Crescent in Windermere, featuring approximately 165 feet of shoreline, breathtaking water views, and a resort-style waterfront lifestyle on a private ski lake known for its exceptional water quality. This beautifully designed custom residence offers approximately 3,086 square feet, 4 bedrooms, and 4 bathrooms, thoughtfully

Jenny Ramirez COLDWELL BANKER REALTY

Stylish and elegant with contemporary touches, welcome home to a magnificent and expansive retreat situated on a 1-acre lot, with full-size lighted sport court with double pickleball courts (or tennis or basketball), set inside the gated enclave of Harbor Isle. This spectacular residence is unduplicated for its secluded setting – yet so close to everything – while offering an abundance of

Rob Rahter STOCKWORTH REALTY GROUP

The Ultimate Entertainer’s Dream Home. Welcome to this exceptional custom-built courtyard estate by Bill Sauerwine, offering 4 bedrooms, 4.5 bathrooms, and 4,549 square feet of luxurious living in the highly sought-after Windermere area. Designed for both grand entertaining and everyday comfort, this stunning residence centers around a private courtyard pool, creating a true indoor-outdoor

Sean Hooke LAKESIDE REALTY WINDERMERE INC

Situated within the beautiful gated community of Waterstone, this impeccably designed custom residence blends timeless architecture, refined finishes, and resort-inspired outdoor living into one extraordinary offering. Encompassing 3,396 square feet, the thoughtfully crafted floor plan features 4 bedrooms, 4 full bathrooms, and 1 half bath, all centered around a stunning private courtyard that

Jay Martin CORCORAN PREMIER REALTY

Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with soaring vaulted ceilings and a cozy wood-burning fireplace. The open-concept kitchen includes a large

Michael Julian JULIAN PROPERTIES, INC.

NEW PRICE – Exceptional value in Lake Butler Sound! Welcome to 11027 Hawkshead Court, a beautifully updated 4-bedroom plus a dedicated office, 4 bath residence offering approximately 3,500 square feet of living space on a private 0.4-acre corner lot in the heart of Windermere, complete with 24 hour roving security. With extensive renovations completed between 2022 and 2026, this move-in-ready

Justyna Tchorni KENNEDY REALTY GROUP LLC

Exceptional Contemporary Estate in the Heart of Windermere! Discover the perfect blend of modern design, timeless comfort, and unmatched location with this beautifully updated estate home, ideally situated on a 1-acre lot in the desirable Town of Windermere. Surrounded by multi-million-dollar residences, and just moments from the famed Butler Chain of Lakes, this property offers a rare

Michael Julian JULIAN PROPERTIES, INC.

Something unexpected! Something unique! An amazing space! Welcome to 6241 Blakeford Drive, where the charm, character, and glamour of this custom-built jewel box home are sure to impress. Designed to capture natural light and stunning water views, this residence offers a floor plan that is both functional and unforgettable. At the heart of the home is a spectacular Great Room featuring soaring

Angela Durruthy KEENE'S POINTE REALTY

BUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP on a .37 acre Lot. Cypress trees line the beautiful serene canal leading directly to the 12 lakes of the Butler Chain. PRIVATE FINANCING IS AVAILABLE - (ask for terms and conditions). Access the Butler chain of lakes from your back yard to Lake Down or Lake Wauseon. Renovate or Build your own modern upscale dream home. Town of Windermere

Bruce Higgins SAND DOLLAR REALTY GROUP INC

Experience refined, single-level living in this exceptional custom home located within Keene’s Pointe, Windermere’s premier guard-gated golf and lakefront community. Designed with both privacy and comfort in mind, this beautifully appointed residence offers 4 bedrooms, 4 full baths, a private office, and a resort-style pool and spa. At the front of the home, the dedicated office enjoys tranquil

Rob Rahter STOCKWORTH REALTY GROUP

PRICE IMPROVEMENT! Recently appraised - Pricing adjusted to reflect current appraised value. This beautiful and elegant courtyard-style estate, complete with a PRIVATE GUEST HOUSE/IN-LAW SUITE, offers the ideal retreat for multi-generational living within one of the most exclusive gated communities in the Town of Windermere. Designed for comfort, refinement, and privacy, this home embodies

Dianna Desboyaux DOUGLAS ELLIMAN