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Vacation Homes for Sale in Windermere, FL

26 homes
New
mls-logo
$480,000
3 bd
|
2.5 ba
|
2,001 sq ft
|
Townhouse

13727 Bressler Aly, Windermere, FL 34786

Modern Elegance in Vineyards of Horizon West – Upgraded & Move-In Ready! Welcome to 13727 Bressler Alley, a stunning townhome in the highly sought-after Vineyards of Horizon West community in Wind...
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New
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$875,000
5 bd
|
3.5 ba
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3,465 sq ft
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House

8330 Vivaro Isle Way, Windermere, FL 34786

Discover the perfect blend of elegance, comfort, and modern convenience in this exceptional 5-bedroom, 3.5-bathroom home in the highly sought-after Windermere Isle community. A charming covered front...
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New
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$949,000
4 bd
|
3.5 ba
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2,642 sq ft
|
House

13413 Hopkinton Ct, Windermere, FL 34786

Newly Renovated Home near Disney!Stunning cul-de-sac Windermere residence, just minutes away from the enchanting world of Disney! 4 spacious bedrooms offering comfort and privacy for the whole family...
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New
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$654,000
4 bd
|
2 ba
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2,521 sq ft
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House

13226 Zori Ln, Windermere, FL 34786

Stunning Home in Prime Windermere Location! Welcome to this beautifully maintained Windermere gem, perfectly situated in a sought-after neighborhood with easy access to top-rated schools, Windermere ...
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$375,000
3 bd
|
2.5 ba
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1,232 sq ft
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Condo

14157 Oasis Cove Blvd Unit 104, Windermere, FL 34786

WHAT A MATICULOUS BEAUTY WITH A WATER VIEW IN BEAUTIFUL OASIS COVE AT LAKESIDE IN WINDERMERE. THE WATER VIEW IS NOT ONLY A VIEW BUT WATER FRONTAGE. The property has three bedrooms, two and a half b...
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Price drop
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$1,275,000
6 bd
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6.5 ba
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5,149 sq ft
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House

7587 Lake Albert Dr, Windermere, FL 34786

One or more photo(s) has been virtually staged. **WELCOME HOME** Lake Burden South **POOL HOME** full of gorgeous upgrades that include a SUMMER KITCHEN complete with bar seating, TWO STORY LIVING RO...
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$5,000,000
6 bd
|
7 ba
|
6,855 sq ft
|
House

4089 Isabella Cir, Windermere, FL 34786

Welcome to 4089 Isabella Cir. A Home Like No Other, Exquisite Custom Luxury in Casabella, Windermere, FL Step into unparalleled luxury with this completely reimagined six-bedroom, six-bathroom est...
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Price drop
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$2,675,000
4 bd
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3 ba
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3,150 sq ft
|
House

4108 Downeast Ln, Windermere, FL 34786

IMPROVED PRICE — (Reduced $625,0000: The price adjustment is generating strong interest. Acting now ensures you don’t miss out on this unique Butler Chain of Lakes opportunity.) Welcome to 4108 Downe...
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$824,900
3 bd
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2 ba
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2,447 sq ft
|
House

9605 Hollyglen Pl, Windermere, FL 34786

One or more photo(s) has been virtually staged. Welcome to the distinguished lakefront community of WINDERMERE DOWNS, located along the tranquil shores of LAKE DOWN, the third-largest lake on the ren...
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$2,750,000
5 bd
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5.5 ba
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5,660 sq ft
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House

6874 Valhalla Way, Windermere, FL 34786

This turn-key, custom-built golf course home is perfectly located in the sought after guard gated golf community of Keene's Pointe. This stunning 5 bedroom, 5.5 bath, oversized 3 car garage home on ...
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$1,799,000
5 bd
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4.5 ba
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4,347 sq ft
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House

6220 Cartmel Ln, Windermere, FL 34786

Exquisite renovated home in the 24-hour guard gated community of Reserve at Lake Butler Sound. This beautiful Windermere home has been remodeled from the imported porcelain tile and hand scraped hard...
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$925,000
3 bd
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3 ba
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2,345 sq ft
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House

12435 Montalcino Cir, Windermere, FL 34786

One or more photo(s) has been virtually staged. Stunning 3-Bedroom Home with Lush Landscaping and Modern Upgrades! Welcome to this gorgeous 2,300+ square foot home offering a perfect blend of comf...
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Price drop
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$1,950,000
4 bd
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3.5 ba
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3,866 sq ft
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House

11036 Schooner Way, Windermere, FL 34786

Newly renovated, this jewel on the Butler Chain of Lakes sits on over an acre within the golf cart zone of the sought-after Town of Windermere. In the mature community of Marina Bay Estates, this two...
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$1,250,000
6 bd
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4.5 ba
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4,563 sq ft
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House

8358 Lookout Pointe Dr, Windermere, FL 34786

Nestled in the highly sought-after Windermere Trails community, this exquisite home offers a blend of modern upgrades, functional spaces, and picturesque views of Lake Reams. Boasting 6 bedrooms, 4.5...
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Price drop
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$549,000
4 bd
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2.5 ba
|
2,342 sq ft
|
House

5014 Wise Bird Dr, Windermere, FL 34786

Fabulous Summerport Home with cute front porch perfect for morning coffee!! This home has been used as a vacation home with little wear or tear. Formal Living and Dining room with upgraded lighting. ...
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Price drop
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$1,394,000
4 bd
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3.5 ba
|
2,791 sq ft
|
House

109 E 12th Ave, Windermere, FL 34786

Welcome to this fully renovated four-bedroom, three-and-a-half-bath home in the heart of Windermere, just steps from Lake Bessie and surrounded by lush, mature landscaping on a spacious corner lot wi...
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$6,500,000
5 bd
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6 ba
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7,405 sq ft
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House

9301 Tibet Pointe Cir, Windermere, FL 34786

Elegant and timeless, this custom Lakefront Estate built by Stonebridge Homes presents like a model as it has been a vacation retreat for the current original owners and it looks as new as the day t...
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Price drop
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$2,900,000
6 bd
|
5.5 ba
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4,599 sq ft
|
House

1003 Oakdale St, Windermere, FL 34786

BIKE WEEK SPECIAL - Buy this home & get your choice of any 2025 Road Glide or Street Glide - Never Lived In Since Completely Remodeled and Expanded - Total of 6 Bedrooms - 5 Full Baths - 1 Pool or Gu...
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