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Homes Under $500K in Winter Springs, FL
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94 listings
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3 bedsWith a pool

Homes Under $500K in Winter Springs, FL

Homes Under $500K in Winter Springs, FL

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24 of 94 Listings
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Homes Under $500K in Winter Springs, FL

24 of 94 Listings

Your Winter Springs agent

MG

Mk Alliance Group

HomeSmart

Lic. #SL3351719

HomeSmartCall Mk
  1. 702 Glasgow Ct — photoNew46Active

    $299,990

    4 bd · 3 ba · 1,878 sqft

    702 Glasgow Ct, Winter Springs, FL

    Jen King · KELLER WILLIAMS HERITAGE REALTY

  2. 466 Tradition Ln — photoNew1Active

    $289,000

    2 bd · 3 ba · 1,275 sqft

    466 Tradition Ln, Winter Springs, FL

    Theresa Hopcraft · SOVEREIGN REALTY INVESTMENTS LLC

  3. 600 Casa Park N Ct. — photoNew27Active

    $219,900

    2 bd · 1 ba · 980 sqft

    600 Casa Park N Ct., Winter Springs, FL

    Carmen Vazquez · REALTY TECH INC

  4. 1056 Condor Pl — photo31Active

    $449,900

    3 bd · 2 ba · 1,524 sqft

    1056 Condor Pl, Winter Springs, FL

    Mark D'Italia · PROPERTY LOGIC RE

  5. 161 Bear Springs Dr — photo29Active

    $500,000

    3 bd · 3 ba · 1,704 sqft

    161 Bear Springs Dr, Winter Springs, FL

    Jason Moulton · SHAHRAM SONDI + CO.

  6. 425 S Hawthorn Cir — photo34Active

    $260,000

    3 bd · 2 ba · 948 sqft

    425 S Hawthorn Cir, Winter Springs, FL

    James Clark · CENTURY 21 ALTON CLARK

  7. 733 Lakeview Dr — photo24Active

    $365,000

    3 bd · 2 ba · 1,597 sqft

    733 Lakeview Dr, Winter Springs, FL

    Karen Albright · OPENDOOR BROKERAGE LLC

  8. 135 Cortez Ct — photo18Active

    $314,900

    3 bd · 2 ba · 1,098 sqft

    135 Cortez Ct, Winter Springs, FL

    Laura Johnston · RE/MAX DOWNTOWN

  9. 491 Harbor Winds Ct — photoOpen house Sat, Oct 24 · 10:00 AM34Active

    $335,000

    3 bd · 3 ba · 1,680 sqft

    491 Harbor Winds Ct, Winter Springs, FL

    Mayrin Varkey · AVANTI WAY REALTY LLC

  10. 1361 San Diego Ct — photo16Active

    $349,900

    3 bd · 2 ba · 1,153 sqft

    1361 San Diego Ct, Winter Springs, FL

    Rob Jones · OFFERPAD BROKERAGE FL, LLC

  11. 499 Club Dr — photo36Active

    $205,000

    2 bd · 2 ba · 1,224 sqft

    499 Club Dr, Winter Springs, FL

    Chris Winn · BLOOM HOME GROUP REALTY LLC

  12. 3600 Biscayne Dr — photoOpen house Sat, Oct 24 · 1:00 PM40Active

    $449,000

    4 bd · 2 ba · 2,498 sqft

    3600 Biscayne Dr, Winter Springs, FL

    Melissa Stalzer · LPT REALTY, LLC

  13. 113 Lido Rd — photo25Active

    $350,000

    4 bd · 2 ba · 1,312 sqft

    113 Lido Rd, Winter Springs, FL

    Nicole Dege · REDFIN CORPORATION

  14. 140 Bombay Ave — photoPrice Reduced24Active

    $345,000

    3 bd · 2 ba · 1,373 sqft

    140 Bombay Ave, Winter Springs, FL

    Janet Garay · FLORIDA REALTY OF MIAMI CORP

  15. 627 Clearn Ct — photo29Active

    $485,000

    5 bd · 4 ba · 1,986 sqft

    627 Clearn Ct, Winter Springs, FL

    Kristine McKinley · RE/MAX TOWN & COUNTRY REALTY

  16. 1013 Walnut Creek CV — photo3Active

    $499,900

    3 bd · 2 ba · 1,947 sqft

    1013 Walnut Creek CV, Winter Springs, FL

    Julie Bailey · HOME SOLD NETWORK LLC

  17. 408 Lancers Dr — photo57Active

    $349,000

    3 bd · 2 ba · 1,406 sqft

    408 Lancers Dr, Winter Springs, FL

    Renee Kumar LLC · LA ROSA REALTY LLC

  18. 1436 Winter Wharf Ln — photo86Active

    $399,000

    3 bd · 4 ba · 1,932 sqft

    1436 Winter Wharf Ln, Winter Springs, FL

    Johnna Brizendine · COLDWELL BANKER REALTY

  19. 711 Thistle Pl — photoPrice ReducedOpen house Sat, Oct 24 · 11:00 AM54Active

    $279,900

    3 bd · 2 ba · 960 sqft

    711 Thistle Pl, Winter Springs, FL

    Kim Laney · FLORIDA REALTY INVESTMENTS

  20. 725 Adidas Rd — photo42Active

    $365,000

    2 bd · 2 ba · 1,289 sqft

    725 Adidas Rd, Winter Springs, FL

    Becky Johnson · EXP REALTY LLC

  21. 855 Benchwood Dr — photoPrice Reduced35Active

    $490,000

    4 bd · 3 ba · 2,268 sqft

    855 Benchwood Dr, Winter Springs, FL

    Thomas Nickley, Jr · KELLER WILLIAMS REALTY AT THE PARKS

  22. 1120 Dappled Elm Ln — photo44Active

    $419,900

    3 bd · 2 ba · 1,510 sqft

    1120 Dappled Elm Ln, Winter Springs, FL

    Dave Vobornik · ABSOLUTE REALTY GROUP, LLC

  23. 131 Kristi Ann Ct — photoPrice Reduced34Active

    $206,499

    2 bd · 2 ba · 898 sqft

    131 Kristi Ann Ct, Winter Springs, FL

    Megan Bish · 407 PROPERTIES

  24. 45 Hayes Rd — photo27Active

    $465,000

    3 bd · 3 ba · 1,732 sqft

    45 Hayes Rd, Winter Springs, FL

    Dejahne Johnson · SET HOMES REALTY LLC

12…4

About Homes Under $500K in Winter Springs, FL

Homes Under $500K in Winter Springs, FL: 94 active listings as of October 23, 2026, 19:04 UTC.

Property types among these 94 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
Single Family Residence5255.3%
Townhouse3133.0%
Condominium99.6%

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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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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.
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    Your Winter Springs agent

    MG

    Mk Alliance Group

    HomeSmart

    Lic. #SL3351719

    HomeSmartCall Mk

    Winter Springs, FL community profile

    Population
    40,563
    Median income
    $85,011
    Housing units
    17,247
    People per sq. mi.
    2,169.1
    Area
    18.7 sq. mi.

    Source: HJN community data

    Winter Springs housing market

    September 2026

    Winter Springs 12-month median sale price trend

    Selling at 97.6% of asking price

    Buyers here are paying below asking. MLS · 42 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 30, 2026

    Median sale price
    $426,250$316,250–$599,375 typical range
    Price per sq. ft.
    $226
    Sales
    54
    Paid in cash
    25.9%

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

    Median list price
    $388,750
    Homes for sale
    124
    Median days on market
    32 days

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

    Year-over-year
    0.5%

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

    Median home size
    1,910 sq. ft.