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  • Mortgage calculator
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3 bedsWith a pool
Homes Under $500K in Winter Springs, FL
95 listings

Homes Under $500K in Winter Springs, FL

Homes Under $500K in Winter Springs, FL

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24 of 95 Listings
Map

Homes Under $500K in Winter Springs, FL

24 of 95 Listings

  1. 3600 Biscayne Dr — photoNew40

Your Winter Springs agent

MG

Mk Alliance Group

HomeSmart

Lic. #SL3351719

HomeSmartCall Mk
Active

$449,000

4 bd · 2 ba · 2,498 sqft

3600 Biscayne Dr, Winter Springs, FL

Melissa Stalzer · LPT REALTY, LLC

  • 140 Bombay Ave — photo24Active

    $355,000

    3 bd · 2 ba · 1,373 sqft

    140 Bombay Ave, Winter Springs, FL

    Janet Garay · FLORIDA REALTY OF MIAMI CORP

  • 113 Lido Rd — photoNewOpen house Sun, Oct 11 · 1:00 PM25Active

    $350,000

    4 bd · 2 ba · 1,312 sqft

    113 Lido Rd, Winter Springs, FL

    Nicole Dege · REDFIN CORPORATION

  • 627 Clearn Ct — photoNew29Active

    $485,000

    5 bd · 4 ba · 1,986 sqft

    627 Clearn Ct, Winter Springs, FL

    Kristine McKinley · RE/MAX TOWN & COUNTRY REALTY

  • 141 N Edgemon Ave — photo12Active

    $199,000

    3 bd · 1 ba · 945 sqft

    141 N Edgemon Ave, Winter Springs, FL

    Zach Mitchell · SAND DOLLAR REALTY GROUP INC

  • 1013 Walnut Creek CV — photo2Active

    $499,900

    3 bd · 2 ba · 1,947 sqft

    1013 Walnut Creek CV, Winter Springs, FL

    Julie Bailey · HOME SOLD NETWORK LLC

  • 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

  • 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

  • 711 Thistle Pl — photo50Active

    $284,900

    3 bd · 2 ba · 960 sqft

    711 Thistle Pl, Winter Springs, FL

    Kim Laney · FLORIDA REALTY INVESTMENTS

  • 725 Adidas Rd — photo42Active

    $365,000

    2 bd · 2 ba · 1,289 sqft

    725 Adidas Rd, Winter Springs, FL

    Becky Johnson · EXP REALTY LLC

  • 855 Benchwood Dr — photo35Active

    $499,000

    4 bd · 3 ba · 2,268 sqft

    855 Benchwood Dr, Winter Springs, FL

    Thomas Nickley, Jr · KELLER WILLIAMS REALTY AT THE PARKS

  • 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

  • 813 Leopard Trail — photo28Active

    $399,900

    3 bd · 2 ba · 1,550 sqft

    813 Leopard Trail, Winter Springs, FL

    Ian Anderson · EXP Realty LLC

  • 131 Kristi Ann Ct — photo34Active

    $206,999

    2 bd · 2 ba · 898 sqft

    131 Kristi Ann Ct, Winter Springs, FL

    Megan Bish · 407 PROPERTIES

  • 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

  • 700 Castlewood Dr — photoPrice Reduced22Active

    $269,900

    3 bd · 2 ba · 1,366 sqft

    700 Castlewood Dr, Winter Springs, FL

    Mel Bernstein · PREMIER SOTHEBYS INT'L REALTY

  • 728 Ridgewood Way — photoPrice Reduced25Active

    $269,900

    3 bd · 2 ba · 1,366 sqft

    728 Ridgewood Way, Winter Springs, FL

    Mel Bernstein · PREMIER SOTHEBYS INT'L REALTY

  • 130 Rhoden Ln — photo29Active

    $220,000

    2 bd · 2 ba · 896 sqft

    130 Rhoden Ln, Winter Springs, FL

    Kelly Popchock · KELLER WILLIAMS REALTY AT THE PARKS

  • 414 Horizon Dr — photo55Active

    $309,000

    3 bd · 2 ba · 1,101 sqft

    414 Horizon Dr, Winter Springs, FL

    Sara Nicholas, PA · CHARLES RUTENBERG REALTY ORLANDO

  • 205 Inkwood Ct — photo37Active

    $429,000

    3 bd · 2 ba · 1,748 sqft

    205 Inkwood Ct, Winter Springs, FL

    Travous Dever · THE KEYES COMPANY

  • 512 Pinebranch Cir — photo45Active

    $330,000

    2 bd · 3 ba · 1,558 sqft

    512 Pinebranch Cir, Winter Springs, FL

    Steven Luppert · COMPASS FLORIDA LLC

  • 1010 W Pebble Beach Cir — photo42Active

    $499,999

    3 bd · 3 ba · 1,732 sqft

    1010 W Pebble Beach Cir, Winter Springs, FL

    Stephanie Cusack · EXP REALTY LLC

  • 654 Cypress Ln — photo34Active

    $325,000

    3 bd · 2 ba · 1,201 sqft

    654 Cypress Ln, Winter Springs, FL

    Wayne Mottley · ELEGANT REALTY LLC

  • 288 Ringwood Dr — photoPrice Reduced52Active

    $450,000

    3 bd · 2 ba · 1,700 sqft

    288 Ringwood Dr, Winter Springs, FL

    Cynthia Luedke · KELLER WILLIAMS ADVANTAGE REALTY

  • 12…4

    Explore Winter Springs homes

    By price

    • Homes Under $300K
    • Homes Under $400K
    • Homes Under $500K

    By bedrooms

    • 3 Bedroom Homes
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    By type

    • Single-Family Homes
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    By feature

    • Homes with a Pool
    Realty.com

    L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

    Equal Housing OpportunityEqual Housing Lender

    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.

    © 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

    Your Winter Springs agent

    MG

    Mk Alliance Group

    HomeSmart

    Lic. #SL3351719

    HomeSmartCall Mk

    Listing data & MLS disclosures

    Daytona Beach Area Association of REALTORS
    IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
    Information is deemed reliable but not guaranteed.
    Listing information ©2026 Daytona Beach Area Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-09-27 20:04:45 UTC
    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.

    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 · This period is still settling

    Winter Springs 12-month median sale price trend

    Selling at 97.6% of asking price

    Buyers here are paying below asking. MLS · 45 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 15, 2026

    Median sale price
    $407,500$316,250–$536,250 typical range
    Price per sq. ft.
    $226
    Sales
    30
    Paid in cash
    20.0%

    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
    33 days

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

    Year-over-year
    -8.4%

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

    Median home size
    1,910 sq. ft.