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3 bedsNew constructionWith a pool
Homes Under $300K in Chipley, FL
93 listings

Homes Under $300K in Chipley, FL

Homes Under $300K in Chipley, FL

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22 of 93 Listings
Map

Homes Under $300K in Chipley, FL

22 of 93 Listings

  1. 3885 Airmont Drive — photoNew15

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$197,990

3 bd · 2 ba · 1,272 sqft

3885 Airmont Drive, Chipley, FL

Octavia P Valencia · WJH Brokerage FL LLC

  • 4184 Quincy Avenue — photoNew15Active

    $196,990

    3 bd · 2 ba · 1,272 sqft

    4184 Quincy Avenue, Chipley, FL

    Octavia P Valencia · WJH Brokerage FL LLC

  • 2294 Geraldine Circle — photoNew32Active

    $269,990

    4 bd · 2 ba · 1,773 sqft

    2294 Geraldine Circle, Chipley, FL

    Octavia P Valencia · WJH Brokerage FL LLC

  • 1717 Vicki Court — photo35Active

    $254,990

    4 bd · 2 ba · 1,684 sqft

    1717 Vicki Court, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 5288 Highway 77 — photo38Active

    $121,000

    2 bd · 2 ba · 924 sqft

    5288 Highway 77, Chipley, FL

    Sheran Whitaker · New Town Realty

  • 4586 Porter Pond Road — photo34Active

    $169,900

    3 bd · 1 ba · 1,088 sqft

    4586 Porter Pond Road, Chipley, FL

    Dale D Gumm · Anchor Realty Florida

  • 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

  • 825 Jones Court — photo30Active

    $179,900

    3 bd · 1 ba · 964 sqft

    825 Jones Court, Chipley, FL

    Tonia Hathaway · CENTURY 21 Commander Realty

  • 837 Maple Street — photo36Active

    $199,990

    4 bd · 2 ba · 1,500 sqft

    837 Maple Street, Chipley, FL

    Elaine G Fenster · Coastal Palms Real Estate

  • 2774 Rolling Pines Road — photo23Active

    $224,900

    2 bd · 2 ba · 1,176 sqft

    2774 Rolling Pines Road, Chipley, FL

    Trudy VanHorn · Berkshire Hathaway HomeServices Beach Properties of Florida

  • 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

  • 760 Brown Street — photo49Active

    $189,999

    3 bd · 2 ba · 1,479 sqft

    760 Brown Street, Chipley, FL

    Casey Owens · Elite Realty

  • 2060 Apollo Drive — photo50Active

    $262,000

    4 bd · 2 ba · 1,673 sqft

    2060 Apollo Drive, Chipley, FL

    Jamie L Zapata · Legacy Premier Agency

  • 2186 Hague Lane — photo56Active

    $244,900

    3 bd · 2 ba · 1,331 sqft

    2186 Hague Lane, Chipley, FL

    Christina Melvin · ERA Neubauer Real Estate, Inc

  • 2246 Orange Hill Road — photoPrice Reduced41Active

    $239,900

    3 bd · 1 ba · 1,350 sqft

    2246 Orange Hill Road, Chipley, FL

    Tina P Dixon · Triple Crown Realty Team

  • 1714 Dora Lane — photo37Active

    $258,990

    4 bd · 2 ba · 1,773 sqft

    1714 Dora Lane, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 3977 Horizon Avenue — photo27Active

    $216,990

    3 bd · 2 ba · 1,290 sqft

    3977 Horizon Avenue, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 1299 Birwood Court — photo29Active

    $184,990

    3 bd · 2 ba · 1,114 sqft

    1299 Birwood Court, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 4301 Country Club Boulevard — photo37Active

    $262,990

    4 bd · 2 ba · 1,773 sqft

    4301 Country Club Boulevard, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 3571 Westbrook Drive — photo28Active

    $228,990

    3 bd · 2 ba · 1,416 sqft

    3571 Westbrook Drive, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 2307 Shenandoah Boulevard — photo27Active

    $217,990

    3 bd · 2 ba · 1,290 sqft

    2307 Shenandoah Boulevard, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 4130 Flint Avenue — photo29Active

    $170,990

    2 bd · 2 ba · 937 sqft

    4130 Flint Avenue, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 12…4

    Explore Chipley homes

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    • New construction
    • With a pool
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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 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: 2026-09-02 20:39:42 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 2026-09-03 17:05:54 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

    June 2026

    Chipley 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 22 sales · as of Jun 30, 2026

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

    Median sale price
    $47,000$18,000–$188,225 typical range
    Price per sq. ft.
    $118
    Sales
    76
    Paid in cash
    75.0%

    Homes on the market · MLS, as of Jun 30, 2026

    Median days on market
    83 days

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

    Year-over-year
    -71.8%