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3 bedsNew constructionWith a pool
108 listings

Homes Under $400K in Winter Park, FL

Homes Under $400K in Winter Park, FL

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24 of 108 Listings
Map

Homes Under $400K in Winter Park, FL

24 of 108 Listings

  1. 7560 Aloma Pines Ct — photo23
Active

$365,000

3 bd · 3 ba · 1,866 sqft

7560 Aloma Pines Ct, Winter Park, FL

Jessica Macias · KELLER WILLIAMS ADVANTAGE III

  • 2500 Lee Rd #123 — photoNew32Active

    $169,900

    1 bd · 1 ba · 645 sqft

    2500 Lee Rd #123, Winter Park, FL

    Scott Sheldon · HOME WISE REALTY GROUP, INC.

  • 188 Sandlewood #1 — photo25Active

    $290,000

    2 bd · 3 ba · 1,133 sqft

    188 Sandlewood #1, Winter Park, FL

    Tom Noelke · NOELKE REALTY

  • 5405 Justine Way — photoNew21Active

    $399,900

    3 bd · 2 ba · 1,247 sqft

    5405 Justine Way, Winter Park, FL

    Yanira Suarez · LPT REALTY, LLC

  • 200 Saint Andrews Blvd #704 — photo40Active

    $159,000

    1 bd · 1 ba · 793 sqft

    200 Saint Andrews Blvd #704, Winter Park, FL

    Alexis Jacobsen · EXP REALTY LLC

  • 1187 Sawmill Court — photo5Active

    $5,000

    3 bd · 2 ba · 1,229 sqft

    1187 Sawmill Court, Winter Park, FL

    Jaime L Boone · Jaime L Boone LLC

  • 7498 Aloma Pines Ct — photo39Active

    $364,900

    3 bd · 3 ba · 1,872 sqft

    7498 Aloma Pines Ct, Winter Park, FL

    Marian Coaxum · KELLER WILLIAMS REALTY AT THE PARKS

  • 1695 Lee Rd #C206 — photo24Active

    $140,000

    2 bd · 1 ba · 881 sqft

    1695 Lee Rd #C206, Winter Park, FL

    Ingrid Garcia Rodriguez · INVESTMENT REALTY

  • 173 Scottsdale Sq #173 — photo13Active

    $100,000

    1 bd · 1 ba · 785 sqft

    173 Scottsdale Sq #173, Winter Park, FL

    Paola Jimenez · AXEN REALTY, LLC

  • 1250 S Denning Dr #119 — photo31Active

    $265,000

    2 bd · 2 ba · 908 sqft

    1250 S Denning Dr #119, Winter Park, FL

    Justin McCarthy · FANNIE HILLMAN & ASSOCIATES

  • 192 Balfour Dr #2 — photo52Active

    $319,000

    2 bd · 2 ba · 1,287 sqft

    192 Balfour Dr #2, Winter Park, FL

    Tricia Ramsby · BHHS FLORIDA REALTY

  • 602 Trinidad Ct #602 — photo31Active

    $227,000

    2 bd · 2 ba · 1,120 sqft

    602 Trinidad Ct #602, Winter Park, FL

    Clara Herrera · CLARA HERRERA REALTY

  • 7348 Grand Ave — photo16Active

    $285,000

    3 bd · 2 ba · 1,509 sqft

    7348 Grand Ave, Winter Park, FL

    Joseph Doher · BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  • 7453 Daniel Webster Dr #a5 — photo20Active

    $150,000

    2 bd · 2 ba · 1,063 sqft

    7453 Daniel Webster Dr #a5, Winter Park, FL

    Laila Dkhissi · LA ROSA REALTY PREMIER LLC

  • 1306 S Pennsylvania Ave #5 — photo33Active

    $359,000

    2 bd · 1 ba · 830 sqft

    1306 S Pennsylvania Ave #5, Winter Park, FL

    Lisa Gould · KELLER WILLIAMS WINTER PARK

  • 2463 Grand Teton Cir #2463 — photo19Active

    $249,000

    3 bd · 3 ba · 1,720 sqft

    2463 Grand Teton Cir #2463, Winter Park, FL

    Jessica Polanco · MAINFRAME REAL ESTATE

  • 5080 Seminole Ave — photo33Active

    $299,900

    3 bd · 2 ba · 1,078 sqft

    5080 Seminole Ave, Winter Park, FL

    David Johnston · CREEGAN GROUP

  • 7302 Swallow Run #7302 — photo24Active

    $134,900

    2 bd · 2 ba · 756 sqft

    7302 Swallow Run #7302, Winter Park, FL

    Katie Nguyen · THE NAVY HOUSE

  • 2383 Sun Valley Cir #2383 — photo33Active

    $234,900

    2 bd · 2 ba · 1,295 sqft

    2383 Sun Valley Cir #2383, Winter Park, FL

    Carmen Aridas · RE/MAX PRIME PROPERTIES

  • 7476 Woodburn Ct #38 — photo28Active

    $170,000

    2 bd · 3 ba · 1,031 sqft

    7476 Woodburn Ct #38, Winter Park, FL

    Habib Fahs · COLDWELL BANKER REALTY

  • 2302 Barbados Dr — photo35Active

    $295,000

    2 bd · 2 ba · 1,544 sqft

    2302 Barbados Dr, Winter Park, FL

    George Freelove · KELLER WILLIAMS REALTY AT THE PARKS

  • 2136 Linden Rd — photo13Active

    $365,000

    3 bd · 2 ba · 1,185 sqft

    2136 Linden Rd, Winter Park, FL

    Patty Hru · PAM REAL ESTATE

  • 2626 Ambergate Rd — photo20Active

    $380,000

    3 bd · 1 ba · 1,143 sqft

    2626 Ambergate Rd, Winter Park, FL

    Brett Winters · OLDE TOWN BROKERS INC

  • 3651 N Goldenrod Rd #C109 — photo18Active

    $165,000

    2 bd · 2 ba · 840 sqft

    3651 N Goldenrod Rd #C109, Winter Park, FL

    Valerie Wanzer · REAL ESTATE PROFESSIONALS SE

  • 12…5

    About Homes Under $400K in Winter Park, FL

    Homes Under $400K in Winter Park, FL: 108 active listings as of October 1, 2026, 20:45 UTC.

    Property types among these 108 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
    Condominium7468.5%
    Single Family Residence1816.7%
    Townhouse1312.0%

    Homes Under $400K in nearby cities

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    • Homes Under $400K in ORLANDO
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    • Homes Under $400K in KISSIMMEE
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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

    Space Coast MLS (Space Coast 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 Space Coast MLS, Inc®. All Rights Reserved. Last Updated: 2026-09-29 11:01:04 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 Park, FL community profile

    Population
    31,855
    Median income
    $98,252
    Housing units
    15,404
    People per sq. mi.
    1,409.5
    Area
    22.6 sq. mi.

    Source: HJN community data

    Winter Park housing market

    September 2026 · This period is still settling

    Winter Park 12-month median sale price trend

    Selling at 97.9% of asking price

    Buyers here are paying below asking. MLS · 73 sales · as of Sep 29, 2026

    Homes that sold · County records, as of Sep 16, 2026

    Median sale price
    $632,500$389,375–$1,088,750 typical range
    Price per sq. ft.
    $379
    Sales
    60
    Paid in cash
    50.0%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

    Median list price
    $630,000
    Homes for sale
    383
    Median days on market
    17 days

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

    Year-over-year
    40.9%

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

    Median home size
    1,731 sq. ft.
    Homes Under $400K in Winter Park, FL