Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Save search

Map layers

Safety

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Homes Under $400K in Chipley, FL
Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

115 listings
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save search
3 bedsNew construction

Homes Under $400K in Chipley, FL

Homes Under $400K in Chipley, FL

Hide Map
23 of 115 Listings
Map

Homes Under $400K in Chipley, FL

23 of 115 Listings

  1. 4293 Rio Drive — photoNew2

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$289,768

3 bd · 2 ba · 1,381 sqft

4293 Rio Drive, Chipley, FL

Jonathan Minerick · HomeCoin.com

  • 4210 Auburndale Drive — photo20Active

    $282,852

    3 bd · 2 ba · 1,650 sqft

    4210 Auburndale Drive, Chipley, FL

    Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

  • 2216 Chase Street — photo20Active

    $276,692

    3 bd · 2 ba · 1,650 sqft

    2216 Chase Street, Chipley, FL

    Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

  • 3888 Bricknell Avenue — photo19Active

    $278,700

    3 bd · 2 ba · 1,279 sqft

    3888 Bricknell Avenue, Chipley, FL

    Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

  • 4208 Auburndale Drive — photo1Active

    $283,412

    3 bd · 2 ba · 1,556 sqft

    4208 Auburndale Drive, Chipley, FL

    Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

  • 1209 Campbellton Avenue — photo7Active

    $25,000

    2 bd · 1 ba · 650 sqft

    1209 Campbellton Avenue, Chipley, FL

    Cindy R Birge · Elite Realty

  • 2212 Chase Street — photo20Active

    $278,848

    4 bd · 2 ba · 1,728 sqft

    2212 Chase Street, Chipley, FL

    Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

  • 3880 Bricknell Avenue — photo1Active

    $299,900

    3 bd · 2 ba · 1,760 sqft

    3880 Bricknell Avenue, Chipley, FL

    Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

  • 4182 Quincy Avenue — photo24Active

    $162,888

    3 bd · 2 ba · 1,114 sqft

    4182 Quincy Avenue, Chipley, FL

    Octavia P Valencia · WJH Brokerage FL LLC

  • 616 Main Street — photo38Active

    $150,000

    4 bd · 2 ba · 1,852 sqft

    616 Main Street, Chipley, FL

    Cindy R Birge · Elite Realty

  • 3359 Cardinal Place — photo17Active

    $187,000

    3 bd · 2 ba · 1,406 sqft

    3359 Cardinal Place, Chipley, FL

    Kingslee N Chamberlain · Gulf Life Real Estate Inc

  • 1508 Aldoro Circle — photo19Active

    $350,000

    3 bd · 2 ba · 2,000 sqft

    1508 Aldoro Circle, Chipley, FL

    Rebecca Weeks · Elite Realty

  • 1258 Hampshire Boulevard — photo108Active

    $289,900

    3 bd · 2 ba · 1,712 sqft

    1258 Hampshire Boulevard, Chipley, FL

    Denise Myers · Elite Realty

  • 2007 Ambassador Court — photoPrice Reduced39Active

    $285,900

    2 bd · 2 ba · 1,333 sqft

    2007 Ambassador Court, Chipley, FL

    Debbie Morton · Bay Living Inc.

  • 3982 Horizon Avenue — photo51Active

    $365,000

    3 bd · 2 ba · 1,725 sqft

    3982 Horizon Avenue, Chipley, FL

    Summer Thomas · Elite Realty

  • 3380 Safari Court — photo59Active

    $329,900

    4 bd · 3 ba · 2,132 sqft

    3380 Safari Court, Chipley, FL

    Leigh Hawkins · Prothro Real Estate & Associates

  • 871 S 8th Street — photo33Active

    $329,999

    3 bd · 2 ba · 1,962 sqft

    871 S 8th Street, Chipley, FL

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

  • 3370 Peppervine Pl — photo51Active

    $385,000

    4 bd · 3 ba · 2,140 sqft

    3370 Peppervine Pl, Chipley, FL

    Wendy Russell · Homesmart

  • 498 Quail Hollow Boulevard — photo31Active

    $299,900

    3 bd · 2 ba · 1,980 sqft

    498 Quail Hollow Boulevard, Chipley, FL

    Melana Weems · Realty Check Real Estate Services

  • 2902 River Lake Drive — photoPrice Reduced40Active

    $324,900

    3 bd · 2 ba · 1,632 sqft

    2902 River Lake Drive, Chipley, FL

    Vanessa Weltlin · Latitudes Realty

  • 2143 Sunny Hills Boulevard — photo21Active

    $269,999

    3 bd · 2 ba · 1,411 sqft

    2143 Sunny Hills Boulevard, Chipley, FL

    Chad Millner · Keller Williams Success Realty

  • 3433 Cardinal Place — photo7Active

    $168,000

    3 bd · 2 ba · 1,012 sqft

    3433 Cardinal Place, Chipley, FL

    Merrie D Allen · Anchor Realty Florida

  • 1990 Ambassador Court — photoPrice Reduced25Active

    $254,400

    3 bd · 2 ba · 1,300 sqft

    1990 Ambassador Court, Chipley, FL

    Steven Koleno · Beycome of Florida LLC

  • 12…5

    About Homes Under $400K in Chipley, FL

    Homes Under $400K in Chipley, FL: 115 active listings as of November 15, 2026, 18:08 UTC.

    Property types among these 115 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
    Single Family Residence9683.5%
    Manufactured Home1916.5%

    Explore Chipley homes

    By price

    • Homes Under $200K
    • Homes Under $300K
    • Homes Under $400K

    By bedrooms

    • 3 Bedroom Homes
    • 4 Bedroom Homes

    By type

    • Single-Family Homes

    By feature

    • New Construction Homes
    Realty.com

    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

    Equal Housing OpportunityEqual Housing Lender

    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.

    © 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

    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: 2026-11-13 23:37:01 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 2026-11-11 15:35:47 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.
    Forgotten Coast (REALTOR Association of Franklin & Gulf Counties)
    Property information provided by the RAFGC MLS – a service of the REALTOR® Association of Franklin & Gulf Counties, Inc. ©2026

    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

    September 2026

    Chipley 12-month median sale price trend

    Selling at 98.7% of asking price

    Buyers here are paying below asking. MLS · 30 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 30, 2026

    Median sale price
    $150,000$18,500–$235,000 typical range
    Price per sq. ft.
    $143
    Sales
    86
    Paid in cash
    65.1%

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

    Median list price
    $265,990
    Homes for sale
    115

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

    Year-over-year
    87.5%

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

    Median home size
    1,582 sq. ft.