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Buy

Start here

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  • Before you start looking
  • The buying timeline

Afford it

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Sell

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  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

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  • Find a seller's agent
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3 bedsNew constructionWith a pool
5 Bedroom Homes in Chipley, FL
6 listings

5 Bedroom Homes in Chipley, FL

5 Bedroom Homes in Chipley, FL

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6 Listings
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5 Bedroom Homes in Chipley, FL

6 Listings

  1. 4059 Falcon Drive — photo31Active

    $371,400

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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

  • 4010 Linwood Drive — photoPrice Reduced37Active

    $289,900

    5 bd · 3 ba · 2,043 sqft

    4010 Linwood Drive, Chipley, FL

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

  • 3783 Payne Lake Road — photo80Active

    $400,000

    5 bd · 4 ba · 3,100 sqft

    3783 Payne Lake Road, Chipley, FL

    Nathan R Lawrence · Legacy Premier Agency LLC

  • 1994 Ambassador Court — photoPrice Reduced37Active

    $282,653

    5 bd · 3 ba · 2,043 sqft

    1994 Ambassador Court, Chipley, FL

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

  • 1798 Normandy Drive — photoPrice Reduced37Active

    $259,573

    5 bd · 3 ba · 2,043 sqft

    1798 Normandy Drive, Chipley, FL

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

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    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

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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: 2026-09-01 18:40:21 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 2026-09-01 15:30:27 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%