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Homes Under $300K in Chipley, FL
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Start here

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  • The buying timeline

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  • Get pre-approved

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101 listings
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3 bedsNew constructionWith a pool

Homes Under $300K in Chipley, FL

Homes Under $300K in Chipley, FL

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24 of 101 Listings
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Homes Under $300K in Chipley, FL

24 of 101 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 5288 Highway 77 — photoNew38Active

    $121,000

    2 bd · 2 ba · 924 sqft

    5288 Highway 77, Chipley, FL

    Sheran Whitaker · New Town Realty

  2. 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

  3. 4533 Hancock Court — photo30Active

    $268,000

    2 bd · 2 ba · 1,337 sqft

    4533 Hancock Court, Chipley, FL

    Melissa Barbee · Barbee Beach House Realty

  4. 1621 Richmond Street — photo28Active

    $228,990

    3 bd · 2 ba · 1,416 sqft

    1621 Richmond Street, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  5. 837 Maple Street — photo35Active

    $199,990

    4 bd · 2 ba · 1,500 sqft

    837 Maple Street, Chipley, FL

    Elaine G Fenster · Coastal Palms Real Estate

  6. 825 Jones Court — photo30Active

    $179,900

    3 bd · 1 ba · 964 sqft

    825 Jones Court, Chipley, FL

    Tonia Hathaway · CENTURY 21 Commander Realty

  7. 972 Sewell Farms Road — photo34Active

    $169,999

    3 bd · 1 ba · 1,054 sqft

    972 Sewell Farms Road, Chipley, FL

    Chris C Allen · Real Broker LLC

  8. 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

  9. 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

  10. 3569 Westbrook Drive — photo23Active

    $248,000

    3 bd · 2 ba · 1,294 sqft

    3569 Westbrook Drive, Chipley, FL

    Gina Williams · Chipola Realty, Chipley Office

  11. 633 3rd Street — photo28Active

    $119,999

    3 bd · 2 ba · 1,823 sqft

    633 3rd Street, Chipley, FL

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

  12. 760 Brown Street — photo49Active

    $189,999

    3 bd · 2 ba · 1,479 sqft

    760 Brown Street, Chipley, FL

    Casey Owens · Elite Realty

  13. 2060 Apollo Drive — photo50Active

    $262,000

    4 bd · 2 ba · 1,673 sqft

    2060 Apollo Drive, Chipley, FL

    Jamie L Zapata · Legacy Premier Agency

  14. 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

  15. 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

  16. 1714 Dora Lane — photo37Active

    $258,990

    4 bd · 2 ba · 1,773 sqft

    1714 Dora Lane, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  17. 3885 Airmont Drive — photo22Active

    $197,990

    2 bd · 2 ba · 1,272 sqft

    3885 Airmont Drive, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  18. 3977 Horizon Avenue — photo27Active

    $216,990

    3 bd · 2 ba · 1,290 sqft

    3977 Horizon Avenue, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  19. 1299 Birwood Court — photo29Active

    $184,990

    3 bd · 2 ba · 1,114 sqft

    1299 Birwood Court, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  20. 2294 Geraldine Circle — photo37Active

    $259,990

    4 bd · 2 ba · 1,773 sqft

    2294 Geraldine Circle, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  21. 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

  22. 3571 Westbrook Drive — photo28Active

    $228,990

    3 bd · 2 ba · 1,416 sqft

    3571 Westbrook Drive, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  23. 2307 Shenandoah Boulevard — photo27Active

    $217,990

    3 bd · 2 ba · 1,290 sqft

    2307 Shenandoah Boulevard, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  24. 4130 Flint Avenue — photo29Active

    $170,990

    2 bd · 2 ba · 937 sqft

    4130 Flint Avenue, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

12…5

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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

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: 2026-08-31 19:09:50 UTC
    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    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%