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3 bedsWith a pool
5 Bedroom Homes in Windermere, FL
48 listings

5 Bedroom Homes in Windermere, FL

5 Bedroom Homes in Windermere, FL

Show Map
24 of 48 Listings
Map

5 Bedroom Homes in Windermere, FL

24 of 48 Listings

  1. 6850 Valhalla Way — photo57Active

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLCCall Veronica

$2,790,000

5 bd · 7 ba · 5,225 sqft

6850 Valhalla Way, Windermere, FL

Shane Croft · COLDWELL BANKER REALTY

  • 6024 Greatwater Dr — photo85Active

    $3,250,000

    5 bd · 6 ba · 6,370 sqft

    6024 Greatwater Dr, Windermere, FL

    Alice Anne Jackson · CORCORAN PREMIER REALTY

  • 2925 Butler Bay Dr N — photoOpen house Sat, Nov 14 · 1:00 PM63Active

    $2,200,000

    5 bd · 5 ba · 3,839 sqft

    2925 Butler Bay Dr N, Windermere, FL

    Fernanda Pizzamiglio · WRA BUSINESS & REAL ESTATE

  • 11209 Macaw Ct — photo56Active

    $2,695,000

    5 bd · 7 ba · 6,105 sqft

    11209 Macaw Ct, Windermere, FL

    Jay Martin · CORCORAN PREMIER REALTY

  • 11103 Bridge House Rd — photo80Active

    $6,750,000

    5 bd · 8 ba · 9,403 sqft

    11103 Bridge House Rd, Windermere, FL

    Rob Rahter · STOCKWORTH REALTY GROUP

  • 105 Forest St — photo47Active

    $2,700,000

    5 bd · 6 ba · 4,430 sqft

    105 Forest St, Windermere, FL

    Tiffany Pantozzi · ALIGN REAL ESTATE LLC

  • 5638 Nectarine Dr — photo68Active

    $1,550,000

    5 bd · 5 ba · 3,612 sqft

    5638 Nectarine Dr, Windermere, FL

    Aziz Elbrak · LA ROSA REALTY LLC

  • 11066 Ullswater Ln — photo38Active

    $3,600,000

    5 bd · 7 ba · 7,223 sqft

    11066 Ullswater Ln, Windermere, FL

    Steven Tavarez · MILA REALTY

  • 5650 Nectarine Dr — photo67Active

    $1,475,000

    5 bd · 5 ba · 3,612 sqft

    5650 Nectarine Dr, Windermere, FL

    Aziz Elbrak · LA ROSA REALTY LLC

  • 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

  • 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

  • 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

  • 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

  • 6120 Greatwater Dr — photo74Active

    $3,999,000

    5 bd · 6 ba · 5,580 sqft

    6120 Greatwater Dr, Windermere, FL

    Teresa Stewart · SOUTHERN REALTY GROUP LLC

  • 101 Lee St — photoPrice Reduced63Active

    $1,300,000

    5 bd · 4 ba · 4,186 sqft

    101 Lee St, Windermere, FL

    Julie Bettosini, PA · STOCKWORTH REALTY GROUP

  • 6614 Bridgewater Village Rd — photo43Active

    $689,900

    5 bd · 3 ba · 3,006 sqft

    6614 Bridgewater Village Rd, Windermere, FL

    Khristian Padilla · MY REALTY GROUP, LLC.

  • 4243 Isabella Cir — photo81Active

    $3,290,000

    5 bd · 7 ba · 5,502 sqft

    4243 Isabella Cir, Windermere, FL

    John Silva · JOHN SILVA REALTY & ASSOCIATES

  • 8142 Tibet Butler Dr — photo79Active

    $2,685,000

    5 bd · 7 ba · 5,747 sqft

    8142 Tibet Butler Dr, Windermere, FL

    Rob Rahter · STOCKWORTH REALTY GROUP

  • 5373 Isleworth Country Club Dr — photo62Active

    $7,200,000

    5 bd · 6 ba · 5,993 sqft

    5373 Isleworth Country Club Dr, Windermere, FL

    Rob Rahter · STOCKWORTH REALTY GROUP

  • 2540 Hempel Cove Ct — photoPrice Reduced70Active

    $1,299,000

    5 bd · 3 ba · 3,356 sqft

    2540 Hempel Cove Ct, Windermere, FL

    Tiffany Pantozzi · ALIGN REAL ESTATE LLC

  • 5526 Marleon Dr — photo98Active

    $2,500,000

    5 bd · 5 ba · 4,661 sqft

    5526 Marleon Dr, Windermere, FL

    Benjamin Attwood · SERHANT

  • 4302 Isabella Cir — photoPrice Reduced90Active

    $3,580,000

    5 bd · 7 ba · 5,362 sqft

    4302 Isabella Cir, Windermere, FL

    Sean Rozanski · JC FLORIDA REALTY LLC

  • 1480 Hempel Ave — photoPrice Reduced43Active

    $1,648,000

    5 bd · 5 ba · 4,219 sqft

    1480 Hempel Ave, Windermere, FL

    Adriana Sanchez · AGENT TRUST REALTY CORPORATION

  • 3986 Isabella Cir — photo29Active

    $3,599,000

    5 bd · 7 ba · 5,342 sqft

    3986 Isabella Cir, Windermere, FL

    Ricardo Konageski da Fonseca · WRA BUSINESS & REAL ESTATE

  • 12

    Explore Windermere homes

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    • Homes Under $500K
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    By bedrooms

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    By type

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    • Homes with a Pool
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    Your Windermere agent

    VF

    Veronica Figueroa

    The Figueroa Team LLC. eXp Realty, LLC

    The Figueroa Team LLC. eXp Realty, LLCCall Veronica

    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.

    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 · This period is still settling

    Windermere 12-month median sale price trend

    Selling at 96.9% of asking price

    Buyers here are paying below asking. MLS · 52 sales · as of Oct 30, 2026

    Homes that sold · County records, as of Oct 19, 2026

    Median sale price
    $634,017$549,951–$996,250 typical range
    Price per sq. ft.
    $272
    Sales
    52
    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
    -23.7%

    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.