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Windermere, FL Homes for Sale — Page 3 | Realty.com
Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
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  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

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  • Commercial

232 listings

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3 bedsWith a pool

Homes for Sale in Windermere, FL

Homes for Sale in Windermere, FL

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24 of 232 Listings
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Homes for Sale in Windermere, FL

24 of 232 Listings

  1. 13019 Garridan Ave — photo57Active

    $620,000

    4 bd · 4 ba · 2,461 sqft

    13019 Garridan Ave, Windermere, FL

    Monica Urrutia · LA ROSA REALTY LLC

  2. 11267 Grander Dr — photo34Active

    $435,000

    3 bd · 3 ba · 1,743 sqft

    11267 Grander Dr, Windermere, FL

    Nathalya Ferreira da Silva · AUTHENTIC REAL ESTATE TEAM

  3. 17538 Black Rail St — photo72Active

    $1,189,000

    5 bd · 5 ba · 4,999 sqft

    17538 Black Rail St, Windermere, FL

    Juliana Franco Alva · KARDOSH REALTY

  4. 6518 Sawyer Shores Ln — photo19Active

    $2,190,000

    5 bd · 6 ba · 3,582 sqft

    6518 Sawyer Shores Ln, Windermere, FL

    Daniel Pavel · WRA BUSINESS & REAL ESTATE

  5. 13125 Penshurst Ln — photoPrice Reduced42Active

    $574,900

    3 bd · 2 ba · 1,948 sqft

    13125 Penshurst Ln, Windermere, FL

    Jason Nagassar · CASTLE REALTY PROFESSIONAL GROUP LLC

  6. 9615 Windy Ridge Rd — photo41Active

    $5,300,000

    6 bd · 8 ba · 9,669 sqft

    9615 Windy Ridge Rd, Windermere, FL

    Traci Cleveland · KELLER WILLIAMS CLASSIC

  7. 8867 Herencia Aly — photo35Active

    $405,000

    3 bd · 3 ba · 1,382 sqft

    8867 Herencia Aly, Windermere, FL

    Jiu Wei · AAA GLOBAL VENTURES PA

  8. 5944 Caymus Loop — photo45Active

    $1,050,000

    4 bd · 3 ba · 2,984 sqft

    5944 Caymus Loop, Windermere, FL

    Teresa Stewart · SOUTHERN REALTY GROUP LLC

  9. 8276 Maritime Flag St #1204 — photoPrice Reduced31Active

    $319,900

    3 bd · 2 ba · 1,455 sqft

    8276 Maritime Flag St #1204, Windermere, FL

    Erica Diaz · HOMEVEST REALTY

  10. 7231 Sangalla Dr — photo67Active

    $1,348,000

    5 bd · 5 ba · 3,835 sqft

    7231 Sangalla Dr, Windermere, FL

    Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

  11. 8576 Powder Ridge Trl — photoPrice Reduced28Active

    $597,000

    4 bd · 4 ba · 2,661 sqft

    8576 Powder Ridge Trl, Windermere, FL

    Sara Alves Subira · WRA BUSINESS & REAL ESTATE

  12. 12785 Westside Village Loop — photoPrice Reduced42Active

    $769,000

    4 bd · 4 ba · 2,996 sqft

    12785 Westside Village Loop, Windermere, FL

    Lisa Gould · KELLER WILLIAMS WINTER PARK

  13. 11963 Vermillion Ave — photo35Active

    $430,000

    3 bd · 3 ba · 1,676 sqft

    11963 Vermillion Ave, Windermere, FL

    Alejandra Silva · METROPOLITAN R.E SOLUTIONS INC

  14. 8168 Boat Hook Loop #302 — photoPrice Reduced54Active

    $293,997

    2 bd · 2 ba · 1,161 sqft

    8168 Boat Hook Loop #302, Windermere, FL

    Omar Andreasen · BLUE KEY PROPERTY MANAGEMENT

  15. 6533 Cartmel Ln — photo52Active

    $1,598,000

    4 bd · 4 ba · 3,751 sqft

    6533 Cartmel Ln, Windermere, FL

    Carolina Medeiros · PREMIER SOTHEBYS INT'L REALTY

  16. 8179 Maritime Flag St #206 — photo47Active

    $350,000

    3 bd · 2 ba · 1,332 sqft

    8179 Maritime Flag St #206, Windermere, FL

    Patricia Zimath, LLC · CHARLES RUTENBERG REALTY ORLANDO

  17. 8229 Tibet Butler Dr — photo56Active

    $1,999,000

    4 bd · 4 ba · 3,912 sqft

    8229 Tibet Butler Dr, Windermere, FL

    Teresa Stewart · SOUTHERN REALTY GROUP LLC

  18. 9602 Maywood Dr — photo93Active

    $4,350,000

    5 bd · 5 ba · 5,305 sqft

    9602 Maywood Dr, Windermere, FL

    Tiphany Weeks · DIAMOND REAL ESTATE GROUP

  19. 6858 Merrick Landing Blvd — photoPrice Reduced38Active

    $595,000

    3 bd · 2 ba · 2,115 sqft

    6858 Merrick Landing Blvd, Windermere, FL

    Wilfred Sierra Sosa · RE/MAX PRIME PROPERTIES

  20. 7030 Mapperton Dr — photo61Active

    $649,000

    4 bd · 3 ba · 2,455 sqft

    7030 Mapperton Dr, Windermere, FL

    Keith Conklin, LLC · FOLIO REALTY LLC

  21. 104 E 1st Ave — photo53Active

    $1,280,000

    4 bd · 3 ba · 2,441 sqft

    104 E 1st Ave, Windermere, FL

    Fernanda Negromonte · NOVA REAL ESTATE SERVICES INC

  22. 8524 Vivaro Isle Way — photo35Active

    $950,000

    4 bd · 3 ba · 2,680 sqft

    8524 Vivaro Isle Way, Windermere, FL

    Vincent Cordaro · SERHANT

  23. 5092 Isleworth Country Club Dr — photo63Active

    $8,500,000

    4 bd · 5 ba · 7,100 sqft

    5092 Isleworth Country Club Dr, Windermere, FL

    Michelle Corbin · ISLEWORTH REALTY LLC

  24. 11727 Delwick Dr — photoPrice Reduced37Active

    $845,000

    4 bd · 3 ba · 2,704 sqft

    11727 Delwick Dr, Windermere, FL

    Catherine Lambert PA · BHHS FLORIDA REALTY

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Listing data & MLS disclosures

Stellar MLS
Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Nearby areas

ZIP codes

  • 34747 (1,279)
  • 34746 (864)
  • 33837 (766)
  • 34787 (753)
  • 33896 (605)
  • 34771 (456)
  • 33897 (451)
  • 34748 (415)

Cities

  • Orlando (3,935)
  • Kissimmee (2,981)
  • Davenport (1,787)
  • St. Cloud (1,007)
  • Winter Garden (729)
  • Clermont (728)
  • Apopka (488)
  • Leesburg (415)

Windermere, FL community profile

Population
3,301
Median income
$148,077
Housing units
1,328
People per sq. mi.
115
Area
28.7 sq. mi.

Source: HJN community data

Windermere housing market

October 2026

Windermere 12-month median sale price trend

Selling at 96.8% of asking price

Buyers here are paying below asking. MLS · 54 sales · as of Oct 30, 2026

Homes that sold · County records, as of Oct 27, 2026

Median sale price
$631,034$548,956–$1,030,000 typical range
Price per sq. ft.
$278
Sales
65
Paid in cash
53.9%

Homes on the market · MLS, as of Oct 18, 2026–Oct 30, 2026

Median list price
$1,139,950
Homes for sale
222
Median days on market
44 days

Price trend · Assessor repeat sales, as of Oct 31, 2026

Year-over-year
-24.1%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size
2,645 sq. ft.