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Windermere is a town in west Orange County, Florida. It is considered part of the Orlando Metropolitan Statistical Area and known for its amazing lakes and being the community of the rich and famous. A highly sought after place to live, Windermere has a noble history that gives the town its modern charm. Founded in 1887, Windermere prides itself on many historical sites such as its Town Hall, Cal Palmer Memorial Building and the Parramore House aka Historic 1890 Windermere Schoolhouse. In 1925, Windermere was incorporated as a town. While its population has exploded over the last three decades, Windermere continues to retain many of its original roads and homes to honor its proud history. The Town of Windermere was recently voted the "Number One Top Choice Towns for Families with Children in the Sunshine State." The prestigious award was given by Neighborhood Scout, which combines data from the national, regional and local sources.

Windermere is a great place to live, raise a family, enjoy your career, or even choose to retire. It offers many housing options for all ages and interests and has become known for its famous sports, movie and television celebrities who call Windermere home, including:  Shaquille O'Neal, Wesley Snipes, Tiger Woods, Bubba Watson, Vince Carter, Joey Fatone, Johnny Damon, Delta Burke, Rick Goings, Ken Griffey Jr, Grant Hill, Philip Michael Thomas, Jim Courier and many more.

Windermere offers many forms of housing including luxury, waterfront, golf front, single-family homes, townhomes, condos, and villas. Prices range from $300K to over $20 million offering opportunities for all types of buyers. Some of the most desirable and elite communities in Central Florida are located in Windermere including Bellaria, Butler Bay, Casa Del Lago, Casabella, Cassabella At Windermere, Chaine Du Lac, Diamondhead, Estates At Lake Clarise, Gotha Town, Harbor Island, Isleworth, Keenes Pointe, Kelso On Lake Butler, Lake Burden, Lake Cypress Cove, Lake Davis Estates, Lake Davis Reserve, Lake Down Shores, Lakes of Windermere, Oxford Moor, Metcalf Park, Reserve At Lake Butler Sound, Sawyer Sound, Summerport Beach, Waterford Pointe, Waterstone, Weatherstone On Lake Olivia and many more.

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Newest Windermere Homes for Sale

732 W 2nd Avenue, Windermere image
732 W 2nd Avenue, Windermere $4,750,000

Perfection on Lake Butler, this beautiful custom home is lakefront living at it’s best! From the open plan kitchen/lounge/dining area that takes in the beauty of the lake...

  • 5 Beds
  • 4.5 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
11800 Vinci Drive, Windermere image
11800 Vinci Drive, Windermere $1,799,900

Prepare to be impressed with this custom courtyard style home built by Silliman Homes. Spacious and open floor plan boasts this southern California style home that offers...

  • 4 Beds
  • 4.5 Baths
  • Keenes Pointe Un #11 SubDv.
  • 34786 Zip Code
6387 Southbridge Street, Windermere image
6387 Southbridge Street, Windermere — 6387 $410,000

Dreams do come true! Whether looking for a vacation home, investment property, or fortunate enough to live in Central Florida year round, just step through the beautiful ...

  • 3 Beds
  • 2.5 Baths
  • Southbridge Village SubDv.
  • 34786 Zip Code
11613 Water Run Alley, Windermere image
11613 Water Run Alley, Windermere — Na $415,000

Welcome to the desirable & sought after town of Windermere. Once you step inside this home, you will feel the love this well-maintained & pristine home has received. This...

  • 3 Beds
  • 2.5 Baths
  • Ashlin Park Ph 2 SubDv.
  • 34786 Zip Code
5837 Caymus Loop, Windermere image
5837 Caymus Loop, Windermere $919,000 ▼

This amazing 5 bedroom, 3 bathroom home located in the prestigious Keene's Pointe won’t stay long. The home is located in a breathtaking, guard-gated golf community on t...

  • 5 Beds
  • 3 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
2613 Coral Stone Court, Windermere image
2613 Coral Stone Court, Windermere $1,190,000

Windermere Custom 2-story Residence located in The Estates at Windermere offers a coveted combination of being in a highly desirable gated community with less than 70 hom...

  • 5 Beds
  • 3.5 Baths
  • Estates At Windermere SubDv.
  • 34786 Zip Code
5054 Sawyer Cove Way, Windermere image
5054 Sawyer Cove Way, Windermere $3,000,000

Welcome Home to your MODERN CUSTOM HOME! This spectacular and rare single story Cam Bradford home is located in the exclusive Sawyer Sound neighborhood. Gorgeous WALL TO...

  • 5 Beds
  • 6.5 Baths
  • Sawyer Sound SubDv.
  • 34786 Zip Code
11373 Arborside Bend Way, Windermere image
11373 Arborside Bend Way, Windermere $519,000

Completely Renovated, ready to move in! Beautiful single story 4 bedroom 2 bathroom home located in a gated community in the heart of Windermere! From the moment you en...

  • 4 Beds
  • 2 Baths
  • Glenmuir 48 39 SubDv.
  • 34786 Zip Code
11630 Via Lucerna Circle, Windermere image
11630 Via Lucerna Circle, Windermere $655,000

Belmer Village is a highly sought after community, Community has a gated entrance, club house, tennis courts pool,basketball court, The family room and kitchen is on th...

  • 4 Beds
  • 3.5 Baths
  • Belmere Village G-5 SubDv.
  • 34786 Zip Code
6146 Golden Dewdrop Trail, Windermere image
6146 Golden Dewdrop Trail, Windermere $1,100,000

Come & see your dream home today!, Beautiful Sunrise and Sunset over pond view. Disney fireworks! Great friendly neighborhood. Upgrades include LED lights and crystal cha...

  • 8 Beds
  • 5 Baths
  • Windermere Lndgs Fd-1 SubDv.
  • 34786 Zip Code
8566 Crescendo Avenue, Windermere image
8566 Crescendo Avenue, Windermere $565,000

Energy efficient Bungalow style house is located in the desirable community of Windermere Trails, a few miles to Disney and close to attractions, shopping center, low HOA...

  • 4 Beds
  • 2.5 Baths
  • Windermere Trls Ph 3b SubDv.
  • 34786 Zip Code
9100 Down Crest Way, Windermere image
9100 Down Crest Way, Windermere $1,125,000

One or more photo(s) has been virtually staged. Welcome home to the gated community of Lake Down Crest. This 4-bedroom, 3.5-bathroom pool home is ready for new owners. Im...

  • 4 Beds
  • 3.5 Baths
  • Lake Down Crest SubDv.
  • 34786 Zip Code
11428 Center Lake Drive, Windermere image
11428 Center Lake Drive, Windermere — N/A $479,000

LOCATION...LOCATION---LOCATION. COMPLETELY RENOVATED TOWNHOME SOUGHT AFTER LAKE BURDEN COMMUNITY IN WINDERMERE. STUNNING VIEW OF THE POIND. VERY INVITING FRONT PORCH. OP...

  • 3 Beds
  • 2.5 Baths
  • Lake Burden South Ph 2 SubDv.
  • 34786 Zip Code
1913 Westover Reserve Boulevard, Windermere image
1913 Westover Reserve Boulevard, Windermere $779,900

GORGEOUS 4BR/3BA - Rarely available beautiful jewel on a tree lined street in amazing location. Move-in and relax. No Inventory Area - Best LOCATION of Windermere that m...

  • 4 Beds
  • 3 Baths
  • Westover Reserve Ph 02 SubDv.
  • 34786 Zip Code
611 Magnolia Street, Windermere image
611 Magnolia Street, Windermere $1,785,000

Amazing opportunity to own this custom build Akers home in the heart of the Town of Windermere - NO HOA fees. The property offers endless upgraded features, this 2 story...

  • 5 Beds
  • 4.5 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
5033 Tildens Grove Boulevard, Windermere image
5033 Tildens Grove Boulevard, Windermere $2,259,300

Welcome to this magnificent Royal Mediterranean Revival-style executive home located in the guard-gated Windermere, Florida community of Tildens Grove. Within minutes of ...

  • 5 Beds
  • 4.5 Baths
  • Tildens Grove Ph 01 47/65 SubDv.
  • 34786 Zip Code
8441 Bowden Way, Windermere image
8441 Bowden Way, Windermere $899,999

Charming 3 bedroom 2.5 bath +Flex Space in sought after Keene's Pointe. This Windermere home is open, bright, and inviting. The kitchen is a chef's dream with plenty of p...

  • 3 Beds
  • 2.5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
11018 Bridge House Road, Windermere image
11018 Bridge House Road, Windermere $2,299,000

Impressive - on 1 beautifully landscaped and fenced lot. 6217 Sq.ft of living area all one ONE FLOOR with a 4-car garage! This former model home with circular drive of...

  • 4 Beds
  • 4.5 Baths
  • Reserve At Lake Butler Sound 45/120 SubDv.
  • 34786 Zip Code
11049 Bagley Alley, Windermere image
11049 Bagley Alley, Windermere $500,000

Welcome to this 3bedroom, 2.5 bathroom, two-story home in the community of Westside Village in Windemere . This home features an open concept with a living, kitchen, and ...

  • 3 Beds
  • 2.5 Baths
  • Westside Village SubDv.
  • 34786 Zip Code
11554 Claymont Cir, Windermere image
11554 Claymont Cir, Windermere $899,900

KEENES POINTE!!! WINDERMERE. Stunning three bedroom, two bath single story raised home in one of the most sought-after 24-hour GUARD GATED community. Located on a SEMI CU...

  • 3 Beds
  • 2 Baths
  • Keenes Pointe Unit 4 (Sec 31) SubDv.
  • 34786 Zip Code
6874 Valhalla Way, Windermere image
6874 Valhalla Way, Windermere $1,790,000

KEENE'S POINTE GOLF FRONT! Custom home with FIRST FLOOR MAIN SUITE and a TWO ROOM - PARENT/IN-LAW/TEENAGEER/GUEST/OR HOME OFFICE SUITE, located on the 14th tee of the Gol...

  • 5 Beds
  • 5.5 Baths
  • Keenes Pointe 46/104 SubDv.
  • 34786 Zip Code
6520 Golden Dewdrop Trail, Windermere image
6520 Golden Dewdrop Trail, Windermere $499,000

Live facing the park in one of Windermere's most desired neighborhoods in Windermere, this house shows like a model home. This home is nestled on a quiet street overlooki...

  • 3 Beds
  • 2.5 Baths
  • Windermere Lndgs Ph 2 SubDv.
  • 34786 Zip Code
5139 Isleworth Country Club Drive, Windermere image
5139 Isleworth Country Club Drive, Windermere $8,900,000

Spectacular Tuscan Modern Custom-Built estate is a once in a lifetime opportunity inspired by the Italian Renaissance. One of the most exclusive private golf and country ...

  • 7 Beds
  • 7.5 Baths
  • Isleworth 01 Amd SubDv.
  • 34786 Zip Code
13029 Penshurst Lane, Windermere image
13029 Penshurst Lane, Windermere $520,000

Ready to Move In, Bright, Upgraded split floorplan Home! Room for a POOL in the fenced backyard! NO Rear Neighbors! The welcoming foyer, dining and living room with doubl...

  • 3 Beds
  • 2 Baths
  • Lakes/Windermere Ph 03 P & Q SubDv.
  • 34786 Zip Code
11461 Claymont Circle, Windermere image
11461 Claymont Circle, Windermere $899,000

MOVE IN READY FOR A NEW OWNER,THE HOME IS LIGHT AND BRIGHT , UPDATED WITH GREAT APPLIANCES, ALONG WITH NEWER PAINT THE COMMUNITY OF KEENS POINTE OFFERS MANY AMENTIES. TH...

  • 3 Beds
  • 3 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code

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