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Windermere Homes for Sale

The Butler Chain of Lakes in Windermere is one of Florida’s most popular areas for lakefront property. Located just 12 miles southwest of Orlando, Windermere is a suburban community in close proximity to theme parks. The town is home to Isleworth Golf Club and Keene’s Pointe Golf Club. Yellow Dog Eats, 33 & Melt and Dexter’s of Windermere are some of the popular restaurants in the area. Local parks include Lake Down Park, Palmer Park, Central Park, Fernwood Park, and Park Among the Lakes. Windermere Preparatory School, Premier Academy, and Family Christian School are highly rated private schools.

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Explore all properties for sale in Windermere, FL in the greater Orlando area listed below. As you search through listings please be sure to contact us with any questions or to schedule a viewing.

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9508 Windy Ridge Road Windermere FL 34786

Price$28,500,000

Est. Mortgage: $/month

MLS Number O5746245

  • Single Family Residential
  • Area 34786 - Windermere
  • Square Feet 51,000
  • Year Built 2011
  • Parking Spaces 10

Listing Courtesy of STOCKWORTH REALTY GROUP

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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9912 Lake Louise Drive Windermere FL 34786

Price$23,000,000

Est. Mortgage: $/month

MLS Number O5714911

  • Single Family Residential
  • Area 34786 - Windermere
  • Square Feet 25,466
  • Year Built 1999
  • Parking Spaces 40

Listing Courtesy of EXP Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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9927 Giffin Court Windermere FL 34786

Price$21,990,000

Est. Mortgage: $/month

MLS Number O5752654

  • Single Family Residential
  • Area 34786 - Windermere
  • Address 9927 Giffin Court
  • Square Feet 31,000
  • Year Built 1990

Listing Courtesy of THE AGENCY COLLECTIVE

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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12488 Park Avenue Windermere FL 34786

Price$16,600,000

Est. Mortgage: $/month

MLS Number O5757261

  • Single Family Residential
  • Area 34786 - Windermere
  • Address 12488 Park Avenue
  • Square Feet 13,425
  • Year Built 1996

Listing Courtesy of REGAL R.E. PROFESSIONALS LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5115 Fairway Oaks Drive Windermere FL 34786

Price$9,790,000

Est. Mortgage: $/month

MLS Number O5433535

  • Single Family Residential
  • Area 34786 - Windermere
  • Square Feet 15,063
  • Year Built 2015
  • Parking Spaces 5

Listing Courtesy of ISLEWORTH REALTY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5372 Isleworth Country Club Drive Windermere FL 34786

MLS Number O5700351

  • Single Family Residential
  • Area 34786 - Windermere
  • Square Feet 13,230
  • Year Built 2004
  • Parking Spaces 3

Listing Courtesy of REGAL R.E. PROFESSIONALS LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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11055 Bridge House Road Windermere FL 34786

Price$6,750,000

Est. Mortgage: $/month

MLS Number O5711522

  • Single Family Residential
  • Area 34786 - Windermere
  • Square Feet 10,452
  • Year Built 2008
  • Parking Spaces 4

Listing Courtesy of LAKESIDE REALTY WINDERMERE INC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5318 Isleworth Country Club Drive Windermere FL 34786

MLS Number O5713515

  • Single Family Residential
  • Area 34786 - Windermere
  • Square Feet 12,298
  • Year Built 2006
  • Parking Spaces 4

Listing Courtesy of ISLEWORTH REALTY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5139 Fairway Oaks Drive Windermere FL 34786

Price$5,685,000

Est. Mortgage: $/month

MLS Number O5775789

  • Single Family Residential
  • Area 34786 - Windermere
  • Square Feet 11,163
  • Year Built 2009
  • Parking Spaces 4

Listing Courtesy of ISLEWORTH REALTY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5020 Down Point Lane Windermere FL 34786

Price$4,949,000

Est. Mortgage: $/month

MLS Number O5701437

  • Single Family Residential
  • Area 34786 - Windermere
  • Address 5020 Down Point Lane
  • Square Feet 9,621
  • Year Built 2005

Listing Courtesy of REGAL R.E. PROFESSIONALS LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6342 Deacon Circle Windermere FL 34786

Price$4,900,000

Est. Mortgage: $/month

MLS Number O5735188

  • Single Family Residential
  • Area 34786 - Windermere
  • Address 6342 Deacon Circle
  • Square Feet 7,008
  • Year Built 1991

Listing Courtesy of ISLEWORTH REALTY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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9520 Windy Ridge Road Windermere FL 34786

Price$4,900,000

Est. Mortgage: $/month

MLS Number O5752665

  • Land
  • Area 34786 - Windermere
  • Co Listing Office Id 50198
  • Subdivision Acreage & Unrec
  • Gated Community

Exceptional lakefront opportunity. May be developed into a cluster of multiple luxury homes or build your dream mansion behind the secured walls of Windermere’s largest estate. Perched above Lake Down with a downward slope to the water affording maximum lakefront views and nightly fireworks displays from Walt Disney World®. The property’s large rectangle shape creates a spectacular private retreat inside this exclusive compound residence. There is already a 3,800 sq foot storage building with 20 ft ceilings on the property including a caretaker's area with 576 sq ft. of living space, a patio area, and courtyard. The size and uniquely high elevation of this coveted address with southern exposure is simply unduplicated on the Butler Chain of Lakes. No time frame to build, no HOA approval, prime location in East Windermere, plus shopping and excellent schools. * Seller unified parcels after purchase. Parcel ID reflects entire 18-acre estate but only the lot noted by red lines is offered for sale at this price. Entire walled compound including main house, 5,600 sq ft grand lodge with catering kitchen and large entertainment hall, a 4,000 sq ft paneled garage with 20 ft. ceilings for car collectors, a separate office with guest apartment, and a massive 50 meter pool is being offered for sale separately. *

Listing Courtesy of STOCKWORTH REALTY GROUP

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details