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Windermere Real Estate Search

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Windermere Listings

9508 Windy Ridge Road, Windermere image
9508 Windy Ridge Road, Windermere $30,000,000

Showcasing Central Florida’s most iconic lakefront estate: an 18-acre compound with 614 feet of pristine frontage on Lake Down on The Butler Chain of Lakes. The Windy Rid...

  • 7 Beds
  • 14 Baths
  • N/A SubDv.
  • 34786 Zip Code
5603 Marleon Drive, Windermere image
5603 Marleon Drive, Windermere $27,000,000

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 ...

  • 7 Beds
  • 10 Baths
  • Na SubDv.
  • 34786 Zip Code
11900 Lake Butler Boulevard, Windermere image
11900 Lake Butler Boulevard, Windermere $17,250,000 ▼

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

  • 7 Beds
  • 9 Baths
  • Metcalf Park Rep SubDv.
  • 34786 Zip Code
6119 Grosvenor Shore Drive, Windermere image
6119 Grosvenor Shore Drive, Windermere $15,900,000

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...

  • 7 Beds
  • 9 Baths
  • Keene's Point SubDv.
  • 34786 Zip Code
12488 Park Avenue, Windermere image
12488 Park Avenue, Windermere $15,500,000

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...

  • 10 Beds
  • 17 Baths
  • Chaine Du Lac SubDv.
  • 34786 Zip Code
3057 Porto Lago Court, Windermere image
3057 Porto Lago Court, Windermere $13,995,000

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...

  • 6 Beds
  • 11 Baths
  • Lake Down Pointe 50 42 SubDv.
  • 34786 Zip Code
9621 Windy Ridge Road, Windermere image
9621 Windy Ridge Road, Windermere $12,999,999 ▼

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...

  • 9 Beds
  • 16 Baths
  • Windsor Hill SubDv.
  • 34786 Zip Code
9832 Laurel Valley Drive, Windermere image
9832 Laurel Valley Drive, Windermere $12,750,000 ▼

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...

  • 6 Beds
  • 10 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9312 Blanche Cove Dr, Windermere image
9312 Blanche Cove Dr, Windermere $12,350,000

Set along beautiful Lake Blanche within the gates of Isleworth, this extraordinary modern estate is a grand haven of remarkable scale and design. Spanning more than 11,00...

  • 7 Beds
  • 10 Baths
  • Isleworth 5th Amd SubDv.
  • 34786 Zip Code
728 Forest Street, Windermere image
728 Forest Street, Windermere $10,200,000

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...

  • 6 Beds
  • 9 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
4226 Downeast Lane, Windermere image
4226 Downeast Lane, Windermere $9,750,000 ▼

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...

  • 34786 Zip Code
4226 Downeast Lane, Windermere image
4226 Downeast Lane, Windermere $9,750,000 ▼

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...

  • 5 Beds
  • 3 Baths
  • Na SubDv.
  • 34786 Zip Code
12422 Park Avenue, Windermere image
12422 Park Avenue, Windermere $8,695,000

WELCOME TO PARK AVENUE. This tremendous opportunity offers 2.19 acres of sprawling possibilities over 2 parcels with Southeastern exposure and sweeping lake views. Nestle...

  • Chaine Du Lac SubDv.
  • 34786 Zip Code
9317 Gladys Garden Court, Windermere image
9317 Gladys Garden Court, Windermere $7,999,000

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

  • 6 Beds
  • 9 Baths
  • Gardens/Isleworth SubDv.
  • 34786 Zip Code
9343 Tibet Pointe Circle, Windermere image
9343 Tibet Pointe Circle, Windermere $7,795,000 ▼

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

  • 7 Beds
  • 10 Baths
  • Keenes Pointe Unit 03 46/104 SubDv.
  • 34786 Zip Code
724 W 2nd Avenue, Windermere image
724 W 2nd Avenue, Windermere $7,500,000

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

  • 6 Beds
  • 8 Baths
  • Windermere SubDv.
  • 34786 Zip Code
5074 Isleworth Country Club Drive, Windermere image
5074 Isleworth Country Club Drive, Windermere $7,250,000 ▼

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

  • 5 Beds
  • 7 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9349 Tibet Pointe Circle, Windermere image
9349 Tibet Pointe Circle, Windermere $6,995,000 ▼

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...

  • 5 Beds
  • 8 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
9061 Ron Den Lane, Windermere image
9061 Ron Den Lane, Windermere $6,900,000

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

  • 5 Beds
  • 7 Baths
  • Down Acres Estates SubDv.
  • 34786 Zip Code
8342 Boyla Court, Windermere image
8342 Boyla Court, Windermere $6,700,000

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

  • 8 Beds
  • 10 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
9316 Gladys Garden Ct, Windermere image
9316 Gladys Garden Ct, Windermere $6,500,000

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

  • 5 Beds
  • 7 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
6462 Deacon Cir, Windermere image
6462 Deacon Cir, Windermere $6,499,999 ▼

Within the gates of Isleworth Golf & Country Club, along the shores of Lake Chase, this exceptional lakefront offers a refined and contemporary waterfront lifestyle. Idea...

  • 5 Beds
  • 6 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9725 Chestnut Ridge Drive, Windermere image
9725 Chestnut Ridge Drive, Windermere $6,000,000 ▼

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

  • 7 Beds
  • 7 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
800 W 2nd Avenue, Windermere image
800 W 2nd Avenue, Windermere $5,999,000

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...

  • 5 Beds
  • 5 Baths
  • Aladar On Lake Butler SubDv.
  • 34786 Zip Code
5138 Fairway Oaks Dr, Windermere image
5138 Fairway Oaks Dr, Windermere $5,500,000

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...

  • 4 Beds
  • 5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
12264 Montalcino Circle, Windermere image
12264 Montalcino Circle, Windermere $5,490,000 ▼

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...

  • 4 Beds
  • 7 Baths
  • Casa Del Lago Rep SubDv.
  • 34786 Zip Code
5199 Latrobe Dr, Windermere image
5199 Latrobe Dr, Windermere $5,300,000

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

  • 6 Beds
  • 7 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9721 Carillon Park Drive, Windermere image
9721 Carillon Park Drive, Windermere $5,000,000 ▼

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 ...

  • 6 Beds
  • 9 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
5070 Down Point Lane, Windermere image
5070 Down Point Lane, Windermere $4,995,000

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...

  • 6 Beds
  • 7 Baths
  • Sunset Bay SubDv.
  • 34786 Zip Code
9575 Westover Roberts Road, Windermere image
9575 Westover Roberts Road, Windermere $4,850,000 ▼

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

  • 7 Beds
  • 8 Baths
  • Gotha Town SubDv.
  • 34786 Zip Code
12540 Park Avenue, Windermere image
12540 Park Avenue, Windermere $4,599,000

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...

  • 5 Beds
  • 6 Baths
  • Chaine Du Lac SubDv.
  • 34786 Zip Code
12418 Park Avenue, Windermere image
12418 Park Avenue, Windermere $4,395,000

WELCOME TO PARK AVENUE. An extraordinary opportunity awaits on 1 acre of prime lakefront with coveted southeastern exposure and sweeping panoramic views. Perfectly positi...

  • Chaine Du Lac SubDv.
  • 34786 Zip Code
9144 Isleworth Gardens Drive, Windermere image
9144 Isleworth Gardens Drive, Windermere $4,300,000 ▼

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

  • 3 Beds
  • 5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
4906 Aviva Garden Court, Windermere image
4906 Aviva Garden Court, Windermere $4,190,000 ▼

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...

  • 3 Beds
  • 5 Baths
  • Gardens/Isleworth Un #2 SubDv.
  • 34786 Zip Code
6120 Greatwater Dr, Windermere image
6120 Greatwater Dr, Windermere $3,999,999 ▼

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

  • 5 Beds
  • 6 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
11002 Lake Butler Boulevard, Windermere image
11002 Lake Butler Boulevard, Windermere $3,999,999 ▼

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

  • 5 Beds
  • 8 Baths
  • Metcalf Park Rep SubDv.
  • 34786 Zip Code
212 W 1st Avenue, Windermere image
212 W 1st Avenue, Windermere $3,900,000 ▲

Pre-Construction. To be built. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity to live in the Town of Wind...

  • 5 Beds
  • 5 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
5151 Latrobe Dr, Windermere image
5151 Latrobe Dr, Windermere $3,900,000 ▼

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...

  • 4 Beds
  • 5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
11539 Lake Butler Boulevard, Windermere image
11539 Lake Butler Boulevard, Windermere $3,800,000

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...

  • 5 Beds
  • 5 Baths
  • Lake Butler Estates SubDv.
  • 34786 Zip Code
12623 Park Avenue, Windermere image
12623 Park Avenue, Windermere $3,800,000

Experience Unparalleled Luxury in Chaine Du Lac Nestled within the sought- after gated community of Chaine Du Lac, this extraordinary custom estate redefines luxury livi...

  • 5 Beds
  • 7 Baths
  • Chaine De Lac SubDv.
  • 34786 Zip Code
9648 Mccormick Place, Windermere image
9648 Mccormick Place, Windermere $3,800,000

Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fair...

  • 3 Beds
  • 4 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9960 6th Street, Windermere image
9960 6th Street, Windermere $3,750,000

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

  • 5 Beds
  • 6 Baths
  • Gotha Town SubDv.
  • 34786 Zip Code
4812 Alexandra Garden Court, Windermere image
4812 Alexandra Garden Court, Windermere $3,699,000

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

  • 3 Beds
  • 5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9731 Chestnut Ridge Drive, Windermere image
9731 Chestnut Ridge Drive, Windermere $3,400,000

Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transi...

  • 4 Beds
  • 4 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
5001 Latrobe Drive, Windermere image
5001 Latrobe Drive, Windermere $3,299,999 ▼

One or more photo(s) has been virtually staged. Traditional five-bedroom four and a half bath pool home with an open layout in Isleworth Golf & Country Club. Perfectly po...

  • 5 Beds
  • 5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
13431 Bellaria Circle, Windermere image
13431 Bellaria Circle, Windermere $3,250,000

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 ...

  • 4 Beds
  • 5 Baths
  • Bellaria SubDv.
  • 34786 Zip Code
13448 Bellaria Circle, Windermere image
13448 Bellaria Circle, Windermere $3,200,000 ▼

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

  • 6 Beds
  • 7 Baths
  • Bellaria SubDv.
  • 34786 Zip Code
13161 Lake Butler Boulevard, Windermere image
13161 Lake Butler Boulevard, Windermere $3,200,000

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...

  • 5 Beds
  • 5 Baths
  • Lake Roper Pointe SubDv.
  • 34786 Zip Code
4819 Alexandra Garden Court, Windermere image
4819 Alexandra Garden Court, Windermere $3,200,000

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

  • 4 Beds
  • 5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
5145 Latrobe Drive, Windermere image
5145 Latrobe Drive, Windermere $2,999,999 ▼

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...

  • 4 Beds
  • 5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
5073 Latrobe Dr, Windermere image
5073 Latrobe Dr, Windermere $2,999,000

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...

  • 4 Beds
  • 6 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
6417 Lake Burden View Drive, Windermere image
6417 Lake Burden View Drive, Windermere $2,960,000

Located within the prestigious guard gated community of Keene’s Pointe, this extraordinary estate offers a rare combination of luxury, privacy, and breathtaking views. Po...

  • 5 Beds
  • 6 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
4301 Down Point Lane, Windermere image
4301 Down Point Lane, Windermere $2,950,000

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...

  • 5 Beds
  • 4 Baths
  • Down Point Sub SubDv.
  • 34786 Zip Code
6130 Grosvenor Shore Drive, Windermere image
6130 Grosvenor Shore Drive, Windermere $2,950,000 ▼

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...

  • 4 Beds
  • 5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
7545 Ficquette Road, Windermere image
7545 Ficquette Road, Windermere $2,950,000 ▼

Back On The Market! Huge Price Improvement! Approx 20 Acres in a very sought after area of Horizon West by many builders. This land is undeveloped and ready for you to pu...

  • 34786 Zip Code
4303 Isabella Circle, Windermere image
4303 Isabella Circle, Windermere $2,899,000

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...

  • 7 Beds
  • 6 Baths
  • Casabella SubDv.
  • 34786 Zip Code
9656 Weatherstone Court, Windermere image
9656 Weatherstone Court, Windermere $2,850,000 ▼

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...

  • 6 Beds
  • 7 Baths
  • Weatherstone On Lake Olivia SubDv.
  • 34786 Zip Code
13250 Bellaria Circle, Windermere image
13250 Bellaria Circle, Windermere $2,800,000

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...

  • 6 Beds
  • 8 Baths
  • Bellaria SubDv.
  • 34786 Zip Code
4205 Clarice Estates Drive, Windermere image
4205 Clarice Estates Drive, Windermere $2,550,000

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...

  • 4 Beds
  • 5 Baths
  • Estates At Lake Clarice SubDv.
  • 34786 Zip Code
1629 Hempel Avenue, Windermere image
1629 Hempel Avenue, Windermere $2,500,000

Welcome to 1629 Hempel Avenue, a private lakefront retreat set on more than one gated acre along Lake Olivia, an approximately 88-acre, spring-fed lake with private acces...

  • 6 Beds
  • 4 Baths
  • Gotha Town SubDv.
  • 34786 Zip Code
6606 Sawyer Shores Lane, Windermere image
6606 Sawyer Shores Lane, Windermere $2,500,000

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 ...

  • 5 Beds
  • 4 Baths
  • Sawyer Shores Sub SubDv.
  • 34786 Zip Code
6288 Blakeford Drive, Windermere image
6288 Blakeford Drive, Windermere $2,474,000 ▼

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...

  • 5 Beds
  • 7 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
9648 Weatherstone Court, Windermere image
9648 Weatherstone Court, Windermere $2,450,000 ▼

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...

  • 6 Beds
  • 4 Baths
  • Weatherstone On Lake Olivia SubDv.
  • 34786 Zip Code
5624 W Lake Butler Road, Windermere image
5624 W Lake Butler Road, Windermere $2,375,000 ▼

Opportunities like this in Windermere rarely reach the open market and are often treasured for generations.Welcome to an extraordinary lakefront estate in the highly cove...

  • 4 Beds
  • 4 Baths
  • Kelso On Lake Butler SubDv.
  • 34786 Zip Code
9620 Maywood Drive, Windermere image
9620 Maywood Drive, Windermere $2,349,000 ▼

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 ...

  • 4 Beds
  • 3 Baths
  • Lake Down Shores SubDv.
  • 34786 Zip Code
1316 Estancia Woods Loop, Windermere image
1316 Estancia Woods Loop, Windermere $2,290,000 ▼

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...

  • 5 Beds
  • 7 Baths
  • Estancia/Windermere SubDv.
  • 34786 Zip Code
2068 Roberts Point Drive, Windermere image
2068 Roberts Point Drive, Windermere $2,250,000 ▼

Virtually Staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita and Lake Access. A rare opportunity in one of Windermere’s mos...

  • 5 Beds
  • 4 Baths
  • Waterford Pointe Ph 02 Rep SubDv.
  • 34786 Zip Code
6102 S Hampshire Court, Windermere image
6102 S Hampshire Court, Windermere $2,240,000 ▼

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 ...

  • 4 Beds
  • 6 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
4224 Clarice Estates Drive, Windermere image
4224 Clarice Estates Drive, Windermere $2,195,000 ▼

Welcome to The Estates at Lake Clarice—one of Windermere's best-kept secrets. If your dream home checklist includes private lake views, breathtaking sunsets, peace and...

  • 5 Beds
  • 4 Baths
  • Estates At Lake Clarice SubDv.
  • 34786 Zip Code
713 Main Street, Windermere image
713 Main Street, Windermere $2,175,000 ▼

Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of His...

  • 6 Beds
  • 6 Baths
  • Windermere SubDv.
  • 34786 Zip Code
436 E 7th Avenue, Windermere image
436 E 7th Avenue, Windermere $2,175,000 ▼

Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence de...

  • 4 Beds
  • 5 Baths
  • Windermere Town Rep SubDv.
  • 34786 Zip Code
1118 Estancia Woods Loop, Windermere image
1118 Estancia Woods Loop, Windermere $2,099,995 ▼

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...

  • 5 Beds
  • 5 Baths
  • Estancia/Windermere SubDv.
  • 34786 Zip Code
1238 Lake Whitney Drive, Windermere image
1238 Lake Whitney Drive, Windermere $2,099,900

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

  • 4 Beds
  • 6 Baths
  • Reserve At Belmere Ph 02 48 144 SubDv.
  • 34786 Zip Code
6560 Lake Burden View Drive, Windermere image
6560 Lake Burden View Drive, Windermere $1,890,000 ▼

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...

  • 4 Beds
  • 4 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
13420 Bonica Way, Windermere image
13420 Bonica Way, Windermere $1,875,000 ▼

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...

  • 5 Beds
  • 4 Baths
  • Tildens Grove SubDv.
  • 34786 Zip Code
2958 Marquesas Court, Windermere image
2958 Marquesas Court, Windermere $1,855,000 ▼

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

  • 5 Beds
  • 5 Baths
  • Lake Crescent Reserve SubDv.
  • 34786 Zip Code
9057 Balmoral Mews Square, Windermere image
9057 Balmoral Mews Square, Windermere $1,854,000 ▼

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...

  • 6 Beds
  • 6 Baths
  • Balmoral SubDv.
  • 34786 Zip Code
6110 Keenes Pointe Drive, Windermere image
6110 Keenes Pointe Drive, Windermere $1,850,000 ▼

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. Sa...

  • 4 Beds
  • 4 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
11226 Macaw Court, Windermere image
11226 Macaw Court, Windermere $1,825,000

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 f...

  • 4 Beds
  • 5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
6241 Blakeford Drive, Windermere image
6241 Blakeford Drive, Windermere $1,795,000

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...

  • 4 Beds
  • 4 Baths
  • Keene's Pointe SubDv.
  • 34786 Zip Code
12001 Lake Butler Boulevard, Windermere image
12001 Lake Butler Boulevard, Windermere $1,775,000

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

  • 3 Beds
  • 3 Baths
  • Lake Butler Estates SubDv.
  • 34786 Zip Code
2503 Butler Bay Drive N, Windermere image
2503 Butler Bay Drive N, Windermere $1,750,000 ▼

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...

  • 4 Beds
  • 3 Baths
  • Butler Bay SubDv.
  • 34786 Zip Code
3013 Seigneury Drive, Windermere image
3013 Seigneury Drive, Windermere $1,750,000 ▼

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 doubl...

  • 4 Beds
  • 5 Baths
  • Harbor Isle SubDv.
  • 34786 Zip Code
212 W 1st Avenue, Windermere image
212 W 1st Avenue, Windermere $1,650,000 ▲

Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity in the Town of Windermere. Boasting approximately 65 feet ...

  • Windermere Town SubDv.
  • 34786 Zip Code
2617 Butler Bay Drive N, Windermere image
2617 Butler Bay Drive N, Windermere $1,649,000

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...

  • 4 Beds
  • 4 Baths
  • Butler Bay SubDv.
  • 34786 Zip Code
11923 Lake Butler Boulevard, Windermere image
11923 Lake Butler Boulevard, Windermere $1,630,000

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 p...

  • 3 Beds
  • 2 Baths
  • Lake Butler Estates SubDv.
  • 34786 Zip Code
12417 Montalcino Circle, Windermere image
12417 Montalcino Circle, Windermere $1,595,000

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...

  • 4 Beds
  • 4 Baths
  • Casa Del Lago-Replat SubDv.
  • 34786 Zip Code
6533 Cartmel Ln, Windermere image
6533 Cartmel Ln, Windermere $1,595,000

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...

  • 5 Beds
  • 4 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
11832 Waterstone Loop Drive, Windermere image
11832 Waterstone Loop Drive, Windermere $1,595,000

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

  • 4 Beds
  • 5 Baths
  • Waterstone SubDv.
  • 34786 Zip Code
33 Main Street, Windermere image
33 Main Street, Windermere $1,575,000

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...

  • 4 Beds
  • 2 Baths
  • Davis Shores SubDv.
  • 34786 Zip Code
13124 Filly Court, Windermere image
13124 Filly Court, Windermere $1,575,000 ▼

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 ...

  • 5 Beds
  • 3 Baths
  • Farms SubDv.
  • 34786 Zip Code
11027 Hawkshead Court, Windermere image
11027 Hawkshead Court, Windermere $1,569,000 ▼

Exceptional value in Lake Butler Sound! Welcome to 11027 Hawkshead Court, a beautifully updated 4-bedroom plus an office, 4 bath residence offering 3,500 square feet on a...

  • 5 Beds
  • 4 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
10948 Down Park Lane, Windermere image
10948 Down Park Lane, Windermere $1,545,000 ▼

LAST REMAINING LOT OF THE FOUR IN THIS EXCLUSIVE PRIVATE ESTATE LAKEFRONT COMMUNITY! Rare opportunity to build your dream home in the highly sought after Town of Winderme...

  • Lake Down Estates SubDv.
  • 34786 Zip Code
11035 Schooner Way, Windermere image
11035 Schooner Way, Windermere $1,500,000

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....

  • 4 Beds
  • 3 Baths
  • Marina Bay Estates SubDv.
  • 34786 Zip Code
9527 Queensbury Court, Windermere image
9527 Queensbury Court, Windermere $1,499,900

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 of flexible livi...

  • 5 Beds
  • 6 Baths
  • Windsor Hill SubDv.
  • 34786 Zip Code
20 Oakdale Street, Windermere image
20 Oakdale Street, Windermere $1,499,000

Welcome to 20 Oakdale Street, an exceptional waterfront luxury residence in the highly sought-after Town of Windermere with direct access to Lake Down and the Butler Chai...

  • 3 Beds
  • 3 Baths
  • Davis Shores SubDv.
  • 34786 Zip Code
11339 Camden Park Drive, Windermere image
11339 Camden Park Drive, Windermere $1,490,000

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...

  • 5 Beds
  • 4 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
12718 Windermere Isles Place, Windermere image
12718 Windermere Isles Place, Windermere $1,480,000 ▼

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...

  • 5 Beds
  • 4 Baths
  • Isles Windermere SubDv.
  • 34786 Zip Code
11015 Hawkshead Court, Windermere image
11015 Hawkshead Court, Windermere $1,450,000 ▼

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...

  • 5 Beds
  • 5 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
9548 Crown Prince Lane, Windermere image
9548 Crown Prince Lane, Windermere $1,450,000

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,...

  • 4 Beds
  • 4 Baths
  • Windsor Hill SubDv.
  • 34786 Zip Code
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  • Altamonte Springs
  • Baldwin Park
  • Celebration
  • Clermont
  • College Park
  • Colonial Town
  • Debary
  • Deltona
  • Downtown Orlando
  • Hunters Creek
  • Lake Mary
  • Longwood
  • Maitland
  • Oviedo
  • Thorton Park
  • SODO (S. of Downtown)
  • Windermere
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