Windermere Pool Homes For Sale 

Windermere Gem: Updated & Move-In Ready! Discover the perfect blend of modern luxury and prime location in the highly sought-after Windermere area. This beautifully up...

Welcome home. This wonderfully kept move-in ready 3 bedroom, 2 bathroom pool home is located in one of SouthWest Orlando's sought after communities, Silver Woods. It feat...

Gorgeous former model home situated on an oversized corner lot with a beautiful private swimming pool! Designed for comfortable living and entertaining, this spacious hom...

Welcome to this spacious pond-front home in Providence, featuring a private screened pool and peaceful water views. Major updates include the roof, A/C system, and water ...

Discover the charm of this water front, 4 bedroom 3.5 bath home located in the desirable Summerport community. This unique property is nestled in the cul de sac for compl...

Welcome home, to a bright and spacious 4 bedroom, 3 full and 2 half baths home in a highly desirable Windermere area. With no HOA where you can bring your boat or RV an...

Virtually Staged. Lake View Home with Private Pool & Fireworks Views – Minutes from Walt Disney World Imagine living in a home that perfectly combines comfort, eleganc...

Windermere Custom Interior Pool Home, 4 bedroom, 2 Primary Suites, 3 full Bathrooms New Exterior and Interior paint 2026, New Hardwood Bamboo Floors 2025, Crown Molding, ...

Welcome to this beautifully maintained and freshly painted 4-bedroom, 2.5-bath pool home with a versatile bonus room, situated on an oversized corner lot in the gated com...

Welcome to this exquisite and impeccably maintained home filled with natural light and elegant open spaces. As you step inside, you are greeted by a soaring ceiling in th...

Virtually Staged. Enjoy the best of Central Florida living in a highly sought-after neighborhood, just minutes from local schools, shopping, great restaurants, and magic ...

Keene's Pointe - 24-hour gated/attended community in Windermere, Florida. 4 bedroom/3 bath home with formal living and dining rooms, kitchen and great room. This furnis...

Located in desirable Windermere Trails and less than 15 minutes from Magic Kingdom, this immaculate 4 bedroom 3 1/2 bath pool home offers an exceptional combination of st...

WELCOME HOME ! WELL MAINTAINED , LARGE, 5 BEDROOM, 4 BATH HOME . ALSO INCLUDES OFFICE, MOVIE ROOM , STORAGE ROOM AND LOFT. OVERSIZE 3 CAR GARAGE,BRICK PAVER DRIVEWAY AND ...

Welcome to a rare opportunity in the highly sought-after The Manors at Butler Bay, in the heart of Windermere. This custom-built home is situated on nearly three-quarters...

This house is the perfect blend of luxury, comfort and modern convenience. From the moment you arrive, you're welcomed by a charming brick paver front porch that leads in...

Experience ELEVATED LUXURY LIVING in this exceptional WINDERMERE TRAILS ESTATE, where timeless elegance, and RESORT-STYLE AMENITIES combine to create an unforgettable pla...

Welcome to this incredible investment opportunity located in one of the most desirable areas in Central Florida. This beautiful property offers the perfect combination of...

Auction Property. A Windermere address. A 24-hour guard-gated community. A home with the scale to make a statement. Tucked along a quiet cul-de-sac in the Reserve at Lake...

Nestled within the highly sought-after Windermere Downs community this Lake-Access Residence, sitting on .74 acres, offers the ultimate Florida lifestyle surrounded by ca...

Beautifully upgraded 4-bedroom residence featuring a thoughtfully designed floor plan, custom finishes, and exceptional indoor-outdoor living. The main level offers a pr...

One or more photos has been virtually staged. ** Check out the photos to see the new improvements just completed in the kitchen and bonus room! ** Welcome to this update...

Price Improvement! Located behind the gates of the prestigious Reserve at Belmere in sought-after Windermere, this exceptional Mediterranean-inspired estate offers a rar...

Luxurious contemporary residence featuring 5 bedrooms, including the primary suite on the main floor. The main level with porcelain tile and marble staircase add sophisti...

One or more photo(s) has been virtually staged. Nestled within the prestigious Enclave at Windermere, this stunning Mediterranean-style residence delivers the Florida lux...

Welcome to this exceptional luxury residence offering 5 spacious bedrooms, 4 beautifully appointed bathrooms, and 3,929 square feet of refined living space on an expansiv...

Beautifully remodeled 5-bedroom residence on a rare nearly one-acre homesite in the heart of Windermere, offering exceptional privacy, a sparkling pool and spa, expansive...

PRICE IMPROVEMENT!!!! UPDATED PHOTOS! Rare opportunity to purchase in the Windermere's Windsor Hill community on a quiet cul-de-sac. This spacious 5-bedroom home offers o...

SELLER MOTIVATED!!! A custom home in the desirable Casa del Lago community. The Spanish-style exterior and elegant, clean transitional interior will surely catch your att...

Nestled on a rare half-acre lot in one of Windermere’s most sought-after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers the ultimate move-in-ready,...

Virtually Staged. Nestled in the heart of Windermere, and featuring more than $300,000 in recent improvements including a brand new roof September 2026, this character-ri...

Stunning Two-Story Pool Home in Prime Windermere Location Welcome to this exceptional two-story residence located in the highly desirable Windermere area, offering the p...

Virtually Staged. Welcome to an exceptional opportunity in the exclusive gated enclave of Balmoral, home to just 32 distinctive custom residences, where privacy, timeless...

Virtually Staged. Set on just over an acre in Windermere, this updated 5-bedroom, 3-bath pool home offers 3,356 square feet of living space, plus a separate flex/bonus ro...

Located within the guard gated community of Reserve at Lake Sound in Windermere, this beautifull 5-bedroom, 5-bath residence offers the perfect blend of elegance, comfort...

Luxury Pond-View Home in Keene’s Pointe – Windermere Located in the highly sought-after gated golf community of Keenes Pointe, this beautiful 5-bedroom, 4-bathroom resid...

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....

An exceptional residence where refined design and effortless living converge. Meticulously remodeled throughout, the home welcomes you with bespoke modern woodwork gracin...

5 Bed 6 bath custom built home in gated community, 1.02 acre lot with private well for all water supply, NO water or sewer bill. Private Basketball court, overside Pool a...

Back on market due to buyer non-performance. Exceptional value in Lake Butler Sound! Welcome to 11027 Hawkshead Court, a beautifully updated luxury home in Windermere, FL...

Welcome to this impeccably designed, all-on-one-floor luxury custom home located in one of the most sought-after gated communities of Windermere, Casa Del Lago, where tim...

Perfectly positioned on the 8th fairway of the renowned Golden Bear Golf Course in Keene's Pointe, this stunning Victorian estate offers timeless elegance, exceptional cr...

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 a...

Welcome to this iconic Arthur Rutenberg custom estate offering 5 bedrooms, 4.5 baths, plus a private executive office with approximately 4,219 sq ft of refined living spa...

Exceptional Contemporary Estate in the Heart of Windermere! Discover the perfect blend of modern design, timeless comfort, and unmatched location with this beautifully...

Back on market due to buyer non-performance WITH PRICE ADJUSTMENT!! Discover an exceptional expression of modern luxury in the heart of Windermere. Welcome to 11051 Hawks...

Experience refined, single-level living in this exceptional custom home located within Keene’s Pointe, Windermere’s premier guard-gated golf and lakefront community. Desi...

PRICE IMPROVEMENT! Rarely available property featuring a separate GUEST HOUSE! Recently appraised - Pricing adjusted to reflect current appraised value. This beautiful an...

Set along the shores of Lake Bessie in the heart of Downtown Windermere, this contemporary lakefront residence pairs clean architectural design with effortless single-sto...

Stunning Lakefront Mediterranean Retreat on Lake Whitney! Discover this spacious, breathtaking lakefront home nestled along the banks of Lake Whitney. Enjoy spectacular v...

Welcome to 4282 McKinnon Rd, a beautifully updated Windermere estate offering exceptional space, privacy, and flexibility on approximately 1.15 acres—with NO HOA. Featuri...

Welcome to Keene’s Pointe - 24-hour gated/attended golf community situated around The Golden Bear Club, an 18-hole Jack Nicklaus golf course featuring golf, tennis, fitne...

Exceptional Keene's Pointe Pool Home with Rare Multi-Generational Layout with a Pond View! Welcome to this exceptional 5-bedroom, 4.5-bath residence nestled on one of...

Lakefront living on the Butler Chain of Lakes in the heart of Windermere. This rare offering on Lake Down presents 100 feet of direct frontage, expansive water views and ...

Set within the private gates of Weatherstone on Lake Olivia, this stunning spring fed lakefront residence offers a rare opportunity to enjoy refined living along the peac...

Completely renovated in 2025. State-of-the-art showpiece located in the beautiful Estates at Lake Clarice. This updated residence offers an effortless blend of generous l...

Positioned on a corner homesite along the 18th hole of the Golden Bear Club within the guard-gated community of Keene's Pointe, this thoughtfully updated custom home offe...

Nestled within the exclusive gated enclave of Weatherstone on Lake Olivia, one of Windermere’s most private and sought-after lakefront communities, this extraordinary est...

MULTI-GENERATIONAL LUXURY LAKEFRONT LIVING. Welcome to 1629 Hempel Avenue, a private lakefront retreat set on more than one gated acre along Lake Olivia, an approximatel...

A rare opportunity to own one of just 18 custom estate homes in this exclusive Windermere enclave of Lake Davis Reserve. Set on more than half an acre, this impressive fi...

Expansive golf course and water views abound from this impressive Keene’s Pointe estate residence, located on the 3rd green of the renowned Jack Nicklaus Signature Golf C...

Set on an elevated corner homesite within Isleworth, this four-bedroom residence presents a unique opportunity to secure a coveted address in one of Central Florida's mos...

Exceptional custom estate in the exclusive guard-gated community of Bellaria featuring 6 bedrooms, 7 full bathrooms, 1 half bath, and a floor plan designed for both every...

Located in one of Windermere’s most sought-after luxury GATED communities with 24-HOUR SECURITY-SCREENED ENTRY, Casabella, this exceptional custom-enhanced ESTATE showcas...

Exceptional Waterview Estate in Keenes Pointe / Resort-Style Outdoor Living. Located on a quiet cul-de-sac in the exclusive guard-gated community of Keenes Pointe, thi...

Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage and no HOA in Sunset Bay. Built in 1983, this 5 bedroom, 4 bath pool home offers...

Welcome to Isleworth Golf & Country Club. This home features a grand entrance that welcomes you with a spacious open foyer featuring a custom bar and a dramatic two-stor...

Virtually Staged. Luxury Lakefront Living with No HOA on an Oversized Lot! Welcome to this exceptional 6-bedroom lakefront estate situated on an oversized lot with no ...

Virtually Staged. Welcome to 12102 Montalcino Circle, an exceptional custom built waterfront estate located in one of Windermere's most sought after gated communities, Ca...

Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course view...

Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa.  Featuring timeless elegance, this beautiful four-bedroom, ...

Welcome to an exceptional luxury residence in the prestigious gated community of Casabella in Windermere. Set on a private 0.71-acre homesite, this stunning Toll Brothers...

Incredible 1st Floor Inlaw Apartment with Full Bath, Sitting Room with Fireplace & Bedroom with Large Walk in Closet * Purchase before October 31, 2026 and receive a full...

Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of fron...

Spectacular Private Gated Lakefront Estate on Lake Olivia in Windermere - From the moment you enter through the custom iron gates, you are welcomed into a private lakefro...

Welcome to the exclusive gates of Isleworth, golf front estate offers over 7,600 square feet of refined luxury living overlooking the fairway of the renowned Isleworth Go...

EXCEPTIONAL LAKEFRONT LUXURY ESTATE IN CASABELLA AT WINDERMERE Discover an extraordinary luxury residence in the prestigious gated community of Casabella at Windermere...

Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating...

Welcome to 4302 Isabella Circle, an exceptional 5-bedroom, 6.5-bath residence offering 5,362 square feet of living space on an expansive 0.88-acre homesite within the gat...

Under Construction. Experience unparalleled luxury in this custom-built Davila Homes estate, ideally located in the heart of Windermere. Showcasing the highly sought-afte...

Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms and more than 5,300 squ...

Welcome to an exceptional opportunity within the gates of Isleworth, one of Central Florida’s most Acclaimed private golf communities. Perfectly positioned along a tranqu...

Welcome to this beautifully furnished luxury residence in the guard-gated community of Casabella in Windermere. Situated on a private half-acre homesite, this impressive ...

Price Adjustment! Lakefront Living in the Heart of Windermere – A Rare Opportunity for Multigenerational Luxury Situated along the tranquil, open waters of Wauseo...

Experience refined luxury living in this extraordinary 5,004-square-foot garden villa estate nestled within Isleworth Golf & Country Club. This impeccably designed reside...

Experience refined luxury in this extraordinary custom estate overlooking the 17th tee of the Jack Nicklaus Signature Golden Bear Club, nestled within the prestigious gua...

Discover “Bella Olivia”: a grand mediterranean estate perched high above Lake Olivia showcasing sweeping lake views, private gates, and an expansive luxury residence span...

Welcome to 9721 Carillon Park Dr, Windermere, FL 34786, a stunning estate inside the guard-gated community of Keene’s Pointe. This extraordinary residence offers 8,305 ...

Nestled behind the gates in the heart of Windermere, this exceptional lakefront estate commands sweeping views across the renowned Butler Chain of Lakes. Designed for ref...

Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country...

Virtually Staged. Set within the gates of renowned Isleworth, this beautifully reimagined golf-front estate presents an exceptional opportunity to experience refined Cent...

Lakefront, Luxurious, home with Private Pool in Windermere. A True Paradise! Discover this rare gem in the heart of Windermere, located in the gated community of Casa De...

Virtually Staged. Pre-Construction. To be built. This is where high-end living meets possibility. A lakefront estate currently under construction in Windermere, set on th...

Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000...

Set beneath a canopy of majestic live oaks along the shores of the Butler Chain of Lakes, this timeless estate has been comprehensively reimagined to blend enduring archi...

Virtually Staged. An exceptional new construction offering within The Gardens of Isleworth, this newly completed residence by premier custom homebuilder Goehring & Morgan...

Positioned along the back nine of Isleworth’s renowned championship golf course, this exceptional estate spans nearly 7,000 square feet and has been thoughtfully reimagin...

Virtually Staged. Welcome to an extraordinary new construction waterfront estate built by Element Home Builders, located in the prestigious 24-hour guard gated community ...

A rare architectural statement on Lake Down, this extraordinary contemporary waterfront estate redefines luxury living in the heart of Windermere. Positioned on the pres...

Stately and elegant lakefront estate showcasing the best of Isleworth West. This grand home spans more than 7,000 square feet with 5 bedrooms- of which, four are on the g...

Set along the pristine shores of Lake Tibet Butler, this exceptional estate within Keene's Pointe is a masterclass in timeless design, refined craftsmanship, and elevated...

Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyon...

A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of Isleworth. Completely r...

DRAMATIC PRICE IMPROVEMENT on this exceptional 5+ acre LAKE DOWN development opportunity, offering 300 feet of pristine shoreline on the coveted BUTLER CHAIN of Lakes and...

Virtually Staged. A true Lake Butler trophy estate. Set within the world-famous gates of Isleworth and commanding panoramic western sunset water views of Lake Butler from...

Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, c...

BRAND NEW ESTATE. A truly exceptional one-of-one on the shores of Lake Down, boasting over 12,000SF, 6BR's, 6/5BA's, and unmatched multigenerational flexibility. Designed...

Commanding a rare 2.75-acre lakefront setting on the coveted Butler Chain of Lakes, this extraordinary Windermere estate is a true work of art. Recently completed after a...

Experience luxury lakefront living on a grand scale in this exquisite estate on Lake Tibet, part of the pristine Butler Chain of Lakes in Windermere. This custom-built ma...

Virtually Staged. Pre-Construction. To be built. Poised on a remarkable .69-acre homesite along the shores of Lake Bessie, this exceptional new residence offers a rare op...

Timeless elegance and extraordinary privacy define this magnificent lakefront estate within the renowned Isleworth Golf & Country Club. Gracefully positioned on Lake Bla...

A rare legacy estate of extraordinary scale and architectural significance, this magnificent lakefront compound spans over 22,000 square feet across more than 11 private ...