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3 bedsNew constructionWith a pool
Homes Under $500K in Chipley, FL — Page 2
130 listings

Homes Under $500K in Chipley, FL

Homes Under $500K in Chipley, FL

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22 of 130 Listings
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Homes Under $500K in Chipley, FL

22 of 130 Listings

  1. 2722 Pioneer Road — photo60Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$399,900

3 bd · 2 ba · 1,772 sqft

2722 Pioneer Road, Chipley, FL

Cindy R Birge · Elite Realty

  • 2235 Voltaire Drive — photo13Active

    $214,990

    3 bd · 2 ba · 1,290 sqft

    2235 Voltaire Drive, Chipley, FL

    Octavia P Valencia · WJH Brokerage FL LLC

  • 1853 Sunny Hills Boulevard — photo27Active

    $249,990

    4 bd · 2 ba · 1,684 sqft

    1853 Sunny Hills Boulevard, Chipley, FL

    Octavia P Valencia · WJH Brokerage FL LLC

  • 3278 Elkcam Boulevard — photo11Active

    $299,900

    4 bd · 2 ba · 1,801 sqft

    3278 Elkcam Boulevard, Chipley, FL

    Steven Koleno · Beycome of Florida LLC

  • 1191 Florence Court — photo26Active

    $254,900

    3 bd · 2 ba · 1,300 sqft

    1191 Florence Court, Chipley, FL

    Steven Koleno · Beycome of Florida LLC

  • 346 Bolick Road — photo12Active

    $56,000

    3 bd · 2 ba · 1,248 sqft

    346 Bolick Road, Chipley, FL

    Stacy Borges · Indian Springs Real Estate

  • 3276 Elkcam Boulevard — photo11Active

    $299,900

    4 bd · 2 ba · 1,801 sqft

    3276 Elkcam Boulevard, Chipley, FL

    Steven Koleno · Beycome of Florida LLC

  • 2205 Sunny Hills Boulevard — photo37Active

    $246,900

    3 bd · 2 ba · 1,300 sqft

    2205 Sunny Hills Boulevard, Chipley, FL

    Steven Koleno · Beycome of Florida LLC

  • 3782 Airmont Drive — photoPrice Reduced38Active

    $257,900

    3 bd · 2 ba · 1,424 sqft

    3782 Airmont Drive, Chipley, FL

    LARS E Langlo · EXP Realty LLC

  • 704 Main Street — photo34Active

    $175,000

    3 bd · 2 ba · 1,644 sqft

    704 Main Street, Chipley, FL

    Tiffany M Davies · Coldwell Banker Realty

  • 2924 Paradise Lakes Road — photo25Active

    $399,900

    4 bd · 3 ba · 1,765 sqft

    2924 Paradise Lakes Road, Chipley, FL

    Kelli White Garrett · CENTURY 21 Commander Realty

  • 3885 Airmont Drive — photo15Active

    $197,990

    3 bd · 2 ba · 1,272 sqft

    3885 Airmont Drive, Chipley, FL

    Octavia P Valencia · WJH Brokerage FL LLC

  • 2294 Geraldine Circle — photo32Active

    $259,990

    4 bd · 2 ba · 1,773 sqft

    2294 Geraldine Circle, Chipley, FL

    Octavia P Valencia · WJH Brokerage FL LLC

  • 1379 Joe Neel Road — photo30Active

    $309,000

    4 bd · 4 ba · 2,380 sqft

    1379 Joe Neel Road, Chipley, FL

    Dustin Ballard · Real Broker LLC

  • 4541 Hancock Court — photoPrice Reduced50Active

    $339,000

    3 bd · 2 ba · 1,705 sqft

    4541 Hancock Court, Chipley, FL

    The Wheeler Sauls Collective · Salty Marlin Realty LLC

  • 4533 Hancock Court — photoPrice Reduced30Active

    $260,000

    2 bd · 2 ba · 1,337 sqft

    4533 Hancock Court, Chipley, FL

    Melissa Barbee · Barbee Beach House Realty

  • 4152 Leisure Lakes Drive — photo52Active

    $369,900

    4 bd · 3 ba · 2,916 sqft

    4152 Leisure Lakes Drive, Chipley, FL

    Scott A Childs · Beachy Beach Real Estate

  • 837 Maple Street — photoPrice Reduced36Active

    $194,990

    4 bd · 2 ba · 1,500 sqft

    837 Maple Street, Chipley, FL

    Elaine G Fenster · Coastal Palms Real Estate

  • 620 4th Street — photoPrice Reduced50Active

    $475,000

    4 bd · 3 ba · 3,756 sqft

    620 4th Street, Chipley, FL

    Seamus J O'neill · SOUTHERN WAY REALTY, INC.

  • 2403 Windbrook Street — photo30Active

    $244,900

    3 bd · 2 ba · 1,580 sqft

    2403 Windbrook Street, Chipley, FL

    Pamela K Hawkins · DR Horton Realty of Emerald Coast, LLC

  • 4059 Falcon Drive — photo31Active

    $371,400

    5 bd · 3 ba · 2,516 sqft

    4059 Falcon Drive, Chipley, FL

    Pamela K Hawkins · DR Horton Realty of Emerald Coast, LLC

  • 2014 Ambassador Court — photo34Active

    $361,400

    5 bd · 3 ba · 2,516 sqft

    2014 Ambassador Court, Chipley, FL

    Pamela K Hawkins · DR Horton Realty of Emerald Coast, LLC

  • 123…6

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    Central Panhandle Association of REALTORS
    IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by the MLS.
    Listing information ©2026 Central Panhandle Association of Realtors®. All Rights Reserved. Last Updated: 2026-09-28 14:34:04 UTC
    Emerald Coast Association of REALTORS
    The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker's logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Data last updated 2026-09-10 14:42:46 UTC
    IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS.

    Chipley, FL community profile

    Population
    3,938
    Median income
    $46,610
    Housing units
    1,766
    People per sq. mi.
    12.8
    Area
    306.9 sq. mi.

    Source: HJN community data

    Chipley housing market

    August 2026

    Chipley 12-month median sale price trend

    Selling at 97.5% of asking price

    Buyers here are paying below asking. MLS · 33 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 28, 2026

    Median sale price
    $74,000$22,000–$230,625 typical range
    Price per sq. ft.
    $137
    Sales
    78
    Paid in cash
    73.1%

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -50.7%