Windermere Pool Homes For Sale 

This stunning Ashton Woods home in the highly sought-after Wickham Park community of Windermere truly shows like a model. Built in 2012, this beautifully maintained singl...

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

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...

Virtually Staged. Welcome to this beautifully maintained 2,683-square-foot home located in the highly desirable Lakes of Windermere community! Offering the perfect blend ...

Welcome to this beautifully maintained two-story home in the highly sought-after Lakes of Windermere, offering 5 bedrooms, 3.5 bathrooms, a private screened pool, and a b...

Welcome to this beautifully maintained one-story home in the highly desirable Summerport community of Windermere! Offering 3 bedrooms, 2 bathrooms, and a versatile office...

PRICED UNDER APPRAISED VALUE! Nestled behind the gated enclave of Eden Isle in Summerport, this stunning five-bedroom, three-bath residence blends modern updates with gen...

Short Sale. Super Rare Opportunity! Tucked away in one of Windermere’s most desirable areas is the beautiful home on over 1 half acre homesite on a corner lot with no rea...

Welcome to this stunning former model home located in highly desirable Windermere! From the moment you step inside you will be greeted by it's open space layout for livi...

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 to this exceptional two-story luxury home in one of Windermere's most sought-after communities. Situated on a beautifully landscaped 0.38-acre lot, this meticulou...

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...

Incredible Opportunity to own a pool home with a huge lot in a fantastic neighborhood * The 1st picture is the proposed new elevation * Call for details about the propose...

Virtually Staged. **Back on the market! 25k price improvement and a new roof being added! Buyers financing fell through.** Located within Lake Butler Estates, one of Wind...

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 quaint...

NEW TILE ROOF INSTALLED PRIOR TO CLOSING! Located in Glenmuir, one of Windermere's most sought-after gated communities, this beautifully maintained pool home offers 4 bed...

Experience the perfect blend of elegance, comfort, and modern convenience in this exceptional 5-bedroom, 4-bathroom home in the highly sought-after Windermere Isle commun...

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

In Windermere homes can be renovated. Locations like this cannot be recreated. Set on more than half an acre with tranquil water views and exceptional privacy, this beaut...

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...

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...

Reduced 50k! Seller motivated! Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled Windermere home offers a 4-bedroom, ...

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...

One or more photos has been virtually staged. Welcome to this updated and meticulously maintained home in the intimate, 64-home community of Estates of Windermere, where ...

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...

Tucked away within the private gates of Casa Del Lago, one of Windermere’s most desirable communities, this exceptional home offers a rare opportunity to enjoy luxury liv...

Experience refined Florida living in this extensively upgraded estate nestled in the sought-after Windermere–Gotha enclave. Set on a rare and private 0.55-acre homesite w...

This exceptional, fully renovated residence offers the perfect blend of contemporary design, luxury finishes, smart technology, and resort-style living. Every detail has ...

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...

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

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...

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...

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...

Spectacular residence tucked away on a quiet cul-de-sac in the heart of Windermere. Situated on a sprawling nearly one-acre lot, this beautifully remodeled home offers an...

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,...

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...

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 over 5,300 square feet ...

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....

Exceptional value in Lake Butler Sound! Welcome to 11027 Hawkshead Court, a beautifully updated luxury home in Windermere, FL offering 4 bedrooms, a dedicated office, 4 b...

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 ...

Situated within the beautiful gated community of Waterstone, this impeccably designed custom residence blends timeless architecture, refined finishes, and resort-inspired...

Welcome to The Reserve at Lake Butler Sound, one of Windermere's most prestigious 24-hour guard-gated luxury communities, where estate homes, tree-lined streets, and acce...

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...

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...

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...

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

SIGNIFICANT PRICE IMPROVEMENT! MOTIVATED SELLER! Welcome to a truly exceptional custom home in Keene's Pointe, one of Windermere’s most sought-after guard-gated communiti...

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 ar...

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...

Discover an exceptional expression of modern luxury in the heart of Windermere. Welcome to 11051 Hawkshead Court, gracefully positioned within the prestigious Reserve at ...

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 ¾-acre homesite a...

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

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, sp...

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

A Masterpiece of Luxury Living in Windermere Welcome to an extraordinary custom estate in the prestigious gated community of Estancia at Windermere, where timeless eleg...

Elegant and spacious home in the highly sought after Estancia at Windermere community, offering the perfect blend of luxury, comfort, and prime Central Florida living. Bu...

Luxury Lakefront Estate – Windermere, FL Discover a truly extraordinary lakefront residence located at one of Windermere's most prestigious addresses. Situated on a sp...

Virtually Staged. This custom-built residence by Rick Watson is located in the sought-after community of Keene’s Pointe, positioned on a private lot overlooking the Jack ...

One or more photo(s) has been virtually staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita, Lake Access & an Exceptional Seller ...

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...

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...

One or more photo(s) has been virtually staged. Pre-Construction. To be built. One or more photo(s) has been virtually staged. UNIQUE CANAL-FRONT PROPERTY ON LAKE SAWYER ...

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...

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...

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...

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...

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...

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...

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 ...

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

Extraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! SPECTACULAR LAKE VIEWS, PRIVACY, SPORTS COURT, AND GAZEBO ON LAKE ROPER - A WATER...

Virtually Staged. Buyer walked days before closing due to personal reasons! All inspections and milestones clean/clear!! - This exceptional Florida residence is perfectly...

BREATHTAKING WINDERMERE ESTATE!!! Situated on nearly 1.5 acres in the gated/guarded community of Bellaria, this custom built 4BR/4.5BA pool residence is the pinnacle of ...

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...

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

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

Welcome to this spectacular 5-bedroom, 5-bathroom custom home offering over 8,000 square feet of thoughtfully designed luxury living—spared no expense and crafted to perf...

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...

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

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...

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...

Extraordinary Lake Butler views abound from this classically elegant yet recently updated Chaine du Lac estate residence. Cradled in a private cove on Windermere’s signat...

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

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...

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 ...

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

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...

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...

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

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...

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...

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

Welcome to an extraordinary lakefront estate on the prestigious shores of Lake Butler with 182 feet of water frontage, where timeless architecture, exceptional craftsmans...

PRICE Improvenent!! Perfectly sited on pristine Lake Tibet in Keene's Pointe Country Club, this stunning lakefront Stonebridge custom home has been completely updated. ...

Under Construction. Currently under construction in the renowned golf course community of Isleworth, this exceptional residence by Goehring & Morgan, thoughtfully designe...

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...

An extraordinary brand-new contemporary lakefront estate on prestigious LAKE BUTLER, part of the renowned Butler Chain of Lakes, offering an exceptional blend of architec...

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

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...

Under Construction. Under Construction. Experience unmatched privacy, prestige, and personalization with this brand-new mansion on 2.5 pristine acres in the heart of Wind...

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...

Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere’s largest and most prestigious Lake Butler, offering captivating un...

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 ...