Windermere FL Homes for Sale - Explore Windermere Real Estate

Experience luxury living in the heart of Orlando, with a 24-hour guard-gated Reserve at Lake Butler Sound in Windermere! Situated on an expansive 0.83-acre homesite, this...

Welcome to 6206 Golden Dewdrop Trail in Windermere Landings — an opportunity to live in Windermere, one of Central Florida's most exclusive and sought-after addresses. Se...

Welcome to this beautiful home in a highly desirable community known for its top-rated schools and beautifully maintained surroundings. Lush landscaping, graceful palm tr...

?? REMODELED HOME IN WINDERMERE! HIGHLY MOTIVATED SELLER! ?? 5231 Lemon Twist Ln, Windermere ??? 4 Bedrooms | ?? 2.5 Bathrooms Discover a spacious home that combin...

Virtually Staged. EXCELLENT OPPORTUNITY TO LIVE OR INVEST! This impressive Kipling model with lake views offers an exceptional combination of comfort, upgrades, and flex...

Very nice two story executive home in the gated community of Lakes of Windermere. Location provides easy access to Disney employees parking, shopping in Windermere. The ...

Under Construction. Seller is selling as is buyer to take over and find new builder....Great piece of land with the best location with main exterior done !!!!

Virtually Staged. Move in. Reimagine. Or build new. Welcome to the Lake Down Shores lifestyle, where one-acre homesites and private community access to the Windermere Cha...

NEWLY BUILT HOME WITH LAKE CAWOOD ACCESS ON APPROXIMATELY 1.70 ACRES! Discover refined lake living in this Ashton Woods Duval residence in Lake Cawood Cove, Windermere, w...

Finding a MODERN, CUSTOM-BUILT LAKEFRONT HOME in Windermere, set on 1.15 ACRES with NO HOA or CDD, is an increasingly rare opportunity. Add exceptional PRIVACY, your own ...

Fully remodeled modern kitchen, Remodeled guest bath, Roof replaced in 2026, so no big-ticket surprises, TWO primary suites, each with a walk-in closet and a double-vanit...

Virtually Staged. Experience extraordinary luxury and cutting-edge technology at 4205 Clarice Court in Windermere! This impressive 7-bedroom, 8.5-bathroom estate offers 7...

WATER VIEW! DISNEY FIREWORKS! 4,999 SQ FT OF LIVING SPACE! TWO PRIMARY SUITES, ONE ON EACH FLOOR! 3 CAR GARAGE! Located in the desirable Enclave community of Windermer...

Virtually Staged. Under Construction. Estimated completion: January 2027. Commanding architecture, soaring interiors and access to Lake Sawyer define this new contemporar...

Gorgeous 3 bedroom 2 bathroom home in the desirable subdivision of Lakes of Windermere. The open concept makes the living spaces feel larger and much more inviting. This...

AVAILABLE FOR SALE OR LEASE. Keene's Pointe, 24-hour gated/attended golf community. Tucked adjacent to the Butler Chain of Lakes this home offers 4 bedrooms, 3 baths, fo...

Virtually Staged. Set behind the gates of Casa Del Lago, 7231 Sangalla Drive offers a fresh interpretation of Windermere living, pairing nearly 4,000 square feet of inter...

NEW PRICE! MOVE-IN READY WINDERMERE HOME WITH PEACEFUL CONSERVATION VIEWS + $12,000 DECOR/RATE BUY DOWN CREDIT! Discover the perfect blend of comfort, style, and locati...

Virtually Staged. Welcome to this exceptional, energy-efficient modern residence built in 2017, perfectly positioned with tranquil lake views in one of the area’s most de...

ONE-STORY, NEW CONSTRUCTION, MODERN FARMHOUSE ELEGANCE ON 1.3 PRIVATE ACRES IN WINDERMERE. Experience an unparalleled synthesis of modern luxury and tranquil, natural bea...

Gracious Golf-Course Living in Keene’s Pointe . Welcome to an exceptional retreat in the prestigious, 24-hour guard-gated community where refined interiors, resort-style ...

Welcome to 9602 Maywood Drive, a privately gated lakefront estate on Windermere's prestigious Butler Chain of Lakes. The home was reimagined through a renovation of more ...

ELEGANCE, PRIVACY & EXCEPTIONAL OUTDOOR LIVING IN GATED WESTOVER RESERVE. Beautifully maintained custom residence set on approximately half an acre in one of Windermere’s...

Virtually Staged. WHIMSICAL POOL HOME | Welcome to the highly desired community of the Lakes Of Windermere. Enjoy the beauty of park-side living and the comfort of your o...

Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive...

Virtually Staged. This home can be purchased with NO INCOME VERIFICATION needed! Seller's preferred lender is willing to contribute 1% of the loan amount toward the buyer...

Set behind the guarded gates of Keene's Pointe, lies this masterfully crafted 7-bedroom, 8-bath lakefront estate by Stonebridge Custom Homes presenting an extraordinary o...

Set within the Gardens of Isleworth, an intimate enclave of custom homes surrounded by lush gardens, water features, bridges and walking paths, this elegant single-story ...

Keene’s Pointe – 24-hour gated/attended community in Windermere, Florida. Experience refined luxury in this exceptional golf-front estate perfectly positioned along the 1...

SINGLE STORY LIVING and PRIVATE PEDESTRIAN-GATED ACCESS to WINDERMERE PREPARATORY SCHOOL from within the community distinguish this custom Waterstone home. Built in 2014 ...

Welcome to 12721 Jacob Grace Court, an exceptional residence nestled within the highly sought-after gated enclave of Tildens Grove in Windermere. Ideally positioned on a ...

WINDERMERE OPPORTUNITY! Welcome to this beautiful 4-bedroom, 2.5-bath home offering 2,214 sq. ft. in the desirable Westside Village community. Built in 2018, this home of...

Welcome to 6126 Payne Stewart Drive, a beautifully renovated golf villa in Isleworth, just steps from the club house. This 2,848-square-foot home offers three bedrooms, e...

Set along the front nine of Isleworth’s championship golf course, the 4,739-square-foot residence has been beautifully reimagined, pairing a grand architectural presence ...

This 4-bedroom, 2-bath pool home in the gated community of Eden Isle offers approximately 2,020 square feet of single-story living with an open floor plan, high ceilings,...

Set on 0.54 acre at the end of a quiet cul-de-sac in the Reserve at Lake Butler Sound, 6533 Cartmel Lane offers single-story living within one of Windermere’s established...

The best sought-after Windermere location! This beautiful Lakes of Windermere 4 bedroom 2.5 bath home was just updated this summer with NEW ROOF, NEW APPLIANCES, NEW CARP...

Set on nearly an acre within the prestigious guard-gated community of Bellaria, this remarkable estate combines grand-scale living, exceptional flexibility, and an unbeat...

Located directly on Lake Tibet within the guard-gated community of Keene’s Pointe, this extensively updated Stonebridge custom residence blends Mediterranean-inspired arc...

Located in the desirable Windermere Trails and less than 15 minutes from Magic Kingdom, this immaculate four-bedroom 3.5-bath pool home offers an exceptional combination ...

Virtually Staged. NEW ROOF COMING SOON! Welcome to 13535 Bramham Lane, a spacious and airy 3-bedroom, 2-bath, single-story home offering plenty of room to spread out and ...

Experience the charm of Old Windermere at 104 E 1st Ave, ideally situated in the heart of one of Central Florida’s most sought-after communities. Set on an oversized 0.45...

This spacious Single-Family Home is located at the Windermere Ashlin Park, 4 bedrooms 3 full bathrooms. ?Large kitchen, bar kitchen island with basin, equipped with stain...

The best family living location! Welcome home to this fabulous 5 bedrooms, 3 full baths, 2 car garage located in the peaceful community of Vineyards in Windermere Florid...

Charming 1 Bedroom 1 Bath Craftsman Cottage on a spacious lot in Downtown Windermere * Whole House Natural Gas Generator keeps the lights and hot water on during all stor...

Virtually Staged. Space, flexibility, and a fantastic Windermere location! Set on a prime CUL-DE-SAC LOT in the GATED Lakes of Windermere-Peachtree community, this spacio...

Experience elevated Florida living in this extraordinary 4,585-square-foot estate, ideally positioned in the heart of Windermere and just 2 miles from Magic Kingdom. Buil...

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...

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...

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

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...

WATER-VIEW SETTING + NIGHTLY MAGIC KINGDOM FIREWORKS + PRIME WINDERMERE LOCATION! Welcome to 12909 Cragside Lane, a beautifully renovated 4-bedroom, 2.5-bath, 2,460-squa...

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...

Opportunity awaits at 9764 Gotha Road! This 2-bedroom, 1-bathroom home offers 1,216 square feet of living space, a private fenced yard, and NO HOA. Whether you're searchi...

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...

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...

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...

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...

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

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...

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...

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, ...

SELLER IS OFFERING A $10,000 CREDIT TO THE BUYER that can be used toward a rate buy-down, closing costs, or paying off the solar panels. Welcome to 8291 Procida Isle Lane...

Completely renovated Gotha/Windermere retreat with NO HOA—bring your boat, RV, or camper! This rare property features a light-filled 3BR/2BA main home with living, dining...

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...

Welcome to this beautifully fully renovated Windermere home, where every room has been thoughtfully updated to create a fresh, modern, move-in-ready living experience. Lo...

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

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...

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 this beautiful, unique, and modern luxury home, built in 2023 and nestled on a generously sized, secluded lot in the highly sought-after and exclusive City of ...

This beautifully renovated 3-bedroom, 2.5-bath luxury home in a prime Windermere location offers the perfect blend of modern elegance, comfort, and peaceful Florida livin...

Beautiful 4 bedrooms, 2.5 bathrooms single-family home in the desirable Windermere area. This spacious home features a thoughtfully designed floor plan with the primary b...

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

Welcome to lakefront living in Windermere! Set along the shores of Lake Burden, this impressive 6-bedroom, 6.5-bath home offers more than 5,100 square feet of living spac...

A rare opportunity in Windermere for the buyer who values space, privacy and flexibility. Set on approximately 1.15 acres with no HOA, 4282 McKinnon Road offers nearly...

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...

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 ...

Virtually Staged. Owner is ready to move on... BOAT INCLUDED IN PURCHASE PRICE: Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an ex...

Virtually Staged. Introducing an exceptional two-story luxury residence in Palms of Windermere, a sought-after, upscale, and intimiate community in the heart of Orange Co...

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...

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...

Welcome to this beautiful maintained traditional-style home in the highly desirable Town of Windermere, Florida, just minutes from the renewed Butler-Chain of Lakes. Nest...

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...

Spectacular Private Lakefront Estate on Lake Olivia, Windermere Near The Grove Shops & Restaurants. Enter through custom Iron gates to this extraordinary Mediterranean es...

Welcome to this beautifully maintained 4-bedroom, 4.5-bath residence situated on a premium 9,055-square-foot corner lot in the highly desirable Wickham Park community of ...

Move-In Ready! Beautifully Updated Home in the Highly Desirable Windermere Area! Welcome to this beautifully refreshed 4-bedroom, 2.5-bath home located in the sought-a...

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...

Located along the 2nd tee of Isleworth's renowned championship golf course, this beautiful golf-front estate offers an exceptional location within the gates. The five-be...

Virtually Staged. Under Construction. SWEETWATER H - Our beautiful huge 2 story home, located on a conservation lot, with 6 Bedrooms and 4.5 Baths. This great floor plan ...

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...

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...

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...

Virtually Staged. Discover this beautifully maintained 3-bedroom, 2-bath corner-lot home in Windermere. Surrounded by tree-lined streets and a welcoming neighborhood atm...

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 ...

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...

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...

Price Improvement! Amazing opportunity to own this beautiful two-story single-family home located in the highly sought-after Lake Sawyer Enclave at Berkshire Park. Built ...

Virtually Staged. One or more photo(s) was virtually staged. *** BRAND NEW ROOF AUG 2026 *** This is your opportunity to own a home in Keene's Pointe, a 24-hour guard-gat...

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...

Discover refined living in one of Windermere's most sought-after communities. This exceptional 5-bedroom, 5-bath residence in Summerport perfectly blends timeless eleganc...