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3 bedsWith a pool
39 listings

Homes Under $500K in Windermere, FL

Homes Under $500K in Windermere, FL

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24 of 39 Listings
Map

Homes Under $500K in Windermere, FL

24 of 39 Listings

  1. 8867 Herencia Aly — photo35Active

$405,000

3 bd · 3 ba · 1,382 sqft

8867 Herencia Aly, Windermere, FL

Jiu Wei · AAA GLOBAL VENTURES PA

  • 8276 Maritime Flag St #1204 — photo31Active

    $324,900

    3 bd · 2 ba · 1,455 sqft

    8276 Maritime Flag St #1204, Windermere, FL

    Erica Diaz · HOMEVEST REALTY

  • 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

  • 8168 Boat Hook Loop #302 — photo54Active

    $299,997

    2 bd · 2 ba · 1,161 sqft

    8168 Boat Hook Loop #302, Windermere, FL

    Omar Andreasen · BLUE KEY PROPERTY MANAGEMENT

  • 8179 Maritime Flag St #206 — photo46Active

    $350,000

    3 bd · 2 ba · 1,332 sqft

    8179 Maritime Flag St #206, Windermere, FL

    Patricia Zimath, LLC · CHARLES RUTENBERG REALTY ORLANDO

  • 11446 Jasper Kay Terrace #202 — photo32Active

    $295,000

    2 bd · 2 ba · 1,161 sqft

    11446 Jasper Kay Terrace #202, Windermere, FL

    Elly Kennedy · KELLER WILLIAMS REALTY AT THE PARKS

  • 13535 Bramham Ln — photo53Active

    $489,900

    3 bd · 2 ba · 1,820 sqft

    13535 Bramham Ln, Windermere, FL

    Scarlett Williams, PA · CENTURY 21 CARIOTI

  • 12934 Vennetta Way — photoOpen house Sat, Oct 17 · 11:00 AM46Active

    $369,000

    3 bd · 3 ba · 1,680 sqft

    12934 Vennetta Way, Windermere, FL

    Karen Grau · REVEL REALTY LLC

  • 8608 Brookvale Dr — photo46Active

    $379,900

    3 bd · 3 ba · 1,480 sqft

    8608 Brookvale Dr, Windermere, FL

    Carola Garcia De Montenegro · AGENT TRUST REALTY CORPORATION

  • 12333 Via Derna Pl — photo53Active

    $449,000

    3 bd · 3 ba · 1,919 sqft

    12333 Via Derna Pl, Windermere, FL

    Marco Romero · KARDOSH REALTY

  • 13424 Hopkinton Ct — photo38Active

    $500,000

    4 bd · 2 ba · 2,190 sqft

    13424 Hopkinton Ct, Windermere, FL

    Jenny Wemert · WEMERT GROUP REALTY LLC

  • 12417 Cruxbury Dr — photoPrice Reduced60Active

    $359,000

    2 bd · 3 ba · 1,311 sqft

    12417 Cruxbury Dr, Windermere, FL

    Christopher Govatos · CHARLES RUTENBERG REALTY ORLANDO

  • 9764 Gotha Rd — photo16Active

    $450,000

    2 bd · 1 ba · 1,216 sqft

    9764 Gotha Rd, Windermere, FL

    Erica Diaz · HOMEVEST REALTY

  • 13048 Garridan Ave — photo24Active

    $445,000

    3 bd · 3 ba · 1,748 sqft

    13048 Garridan Ave, Windermere, FL

    Isabel Sirizzotti · SUNNY 365 REALTY GROUP

  • 8168 Boat Hook Loop #303 — photo20Active

    $320,000

    3 bd · 2 ba · 1,442 sqft

    8168 Boat Hook Loop #303, Windermere, FL

    Jay Stewart · SOUTHERN REALTY GROUP LLC

  • 7430 Bentonshire Ave — photoOpen house Sun, Oct 18 · 1:00 PM59Active

    $354,900

    2 bd · 3 ba · 1,412 sqft

    7430 Bentonshire Ave, Windermere, FL

    Chris Bunnell · EXP REALTY LLC

  • 11425 Brownstone St — photoPrice Reduced35Active

    $410,000

    3 bd · 3 ba · 1,881 sqft

    11425 Brownstone St, Windermere, FL

    Nicole Dege · REDFIN CORPORATION

  • 8860 Herencia Aly — photoPrice Reduced30Active

    $398,000

    3 bd · 3 ba · 1,547 sqft

    8860 Herencia Aly, Windermere, FL

    Babi Hennemann · WRA BUSINESS & REAL ESTATE

  • 7752 Rigby St — photoPrice Reduced23Active

    $395,000

    3 bd · 3 ba · 1,335 sqft

    7752 Rigby St, Windermere, FL

    Ayoub Aitelhaj · ATLIS REALTY GROUP LLC

  • 12914 Vennetta Way — photoPrice Reduced50Active

    $379,900

    3 bd · 3 ba · 1,644 sqft

    12914 Vennetta Way, Windermere, FL

    Lucy Gacioch · BHHS FLORIDA REALTY

  • 12744 Langstaff Dr — photoPrice Reduced33Active

    $394,900

    3 bd · 3 ba · 1,369 sqft

    12744 Langstaff Dr, Windermere, FL

    Veronica Martinez · MY REALTY GROUP, LLC.

  • 8386 Iron Mountain Trl — photoPrice Reduced49Active

    $438,000

    4 bd · 3 ba · 1,631 sqft

    8386 Iron Mountain Trl, Windermere, FL

    Hilda Teran Nava · MY REALTY GROUP, LLC.

  • 11429 Brownstone St — photoPrice Reduced40Active

    $429,000

    4 bd · 3 ba · 1,910 sqft

    11429 Brownstone St, Windermere, FL

    Jenny Wemert · WEMERT GROUP REALTY LLC

  • 14030 Sparkling Cove Ln #603 — photoPrice Reduced35Active

    $324,900

    2 bd · 3 ba · 1,232 sqft

    14030 Sparkling Cove Ln #603, Windermere, FL

    Shane Jordan · COLDWELL BANKER REALTY

  • 12

    About Homes Under $500K in Windermere, FL

    Homes Under $500K in Windermere, FL: 39 active listings as of October 16, 2026, 20:10 UTC.

    Property types among these 39 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
    Property typeListingsShare
    Townhouse2666.7%
    Condominium923.1%

    Explore Windermere homes

    By price

    • Homes Under $500K
    • Homes Under $600K
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    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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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

    Your Windermere agent

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    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

    September 2026 · This period is still settling

    Windermere 12-month median sale price trend

    Selling at 97.1% of asking price

    Buyers here are paying below asking. MLS · 44 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 29, 2026

    Median sale price
    $780,000$532,450–$1,219,535 typical range
    Price per sq. ft.
    $303
    Sales
    51
    Paid in cash
    47.1%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $1,090,000
    Homes for sale
    248
    Median days on market
    31 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    -20.4%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

    Median home size
    2,645 sq. ft.
    Homes Under $500K in Windermere, FL