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

Registered offenders on the map

Save search

Registered offenders on the map

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
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

Registered offenders on the map

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 $500K in Chipley, FL — Page 3
128 listings

Homes Under $500K in Chipley, FL

Homes Under $500K in Chipley, FL

Hide Map
23 of 128 Listings
Map

Homes Under $500K in Chipley, FL

23 of 128 Listings

  1. 3445 Cardinal Place — photo59Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$349,900

3 bd · 2 ba · 1,379 sqft

3445 Cardinal Place, Chipley, FL

Harvey B Webb · Counts Real Estate Group

  • 2186 Hague Lane — photoPrice Reduced56Active

    $238,900

    3 bd · 2 ba · 1,331 sqft

    2186 Hague Lane, Chipley, FL

    Christina Melvin · ERA Neubauer Real Estate, Inc

  • 1299 Birwood Court — photo29Active

    $184,990

    3 bd · 2 ba · 1,114 sqft

    1299 Birwood Court, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 3885 Airmont Drive — photo22Active

    $197,990

    3 bd · 2 ba · 1,272 sqft

    3885 Airmont Drive, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 2294 Geraldine Circle — photo37Active

    $259,990

    4 bd · 2 ba · 1,773 sqft

    2294 Geraldine Circle, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 1714 Dora Lane — photo37Active

    $262,990

    4 bd · 2 ba · 1,773 sqft

    1714 Dora Lane, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 4301 Country Club Boulevard — photo37Active

    $264,990

    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

  • 4130 Flint Avenue — photo29Active

    $170,990

    2 bd · 2 ba · 937 sqft

    4130 Flint Avenue, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 2307 Shenandoah Boulevard — photo27Active

    $219,990

    3 bd · 2 ba · 1,290 sqft

    2307 Shenandoah Boulevard, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 1710 Vicki Court — photo37Active

    $265,990

    4 bd · 2 ba · 1,773 sqft

    1710 Vicki Court, Chipley, FL

    Octavia Valencia · WJH Brokerage FL LLC

  • 672 Main Street — photoPrice Reduced40Active

    $266,900

    3 bd · 2 ba · 1,740 sqft

    672 Main Street, Chipley, FL

    Raul Hernandez · Legacy Premier Agency

  • 2121 Angora Drive — photo45Active

    $289,000

    3 bd · 2 ba · 1,642 sqft

    2121 Angora Drive, Chipley, FL

    LaNessa C Alexander · Counts Real Estate Group Inc

  • 4114 Irene Lane — photoPrice Reduced27Active

    $254,900

    4 bd · 2 ba · 1,799 sqft

    4114 Irene Lane, Chipley, FL

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

  • 3993 Oxford Avenue — photoPrice Reduced27Active

    $254,900

    4 bd · 2 ba · 1,799 sqft

    3993 Oxford Avenue, Chipley, FL

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

  • 1500 Peel Road — photo45Active

    $150,000

    3 bd · 2 ba · 1,224 sqft

    1500 Peel Road, Chipley, FL

    Kim D Francks · ERA American Real Estate

  • 3918 Bricknell Avenue — photoPrice Reduced27Active

    $194,900

    3 bd · 2 ba · 1,259 sqft

    3918 Bricknell Avenue, Chipley, FL

    Carly J Harless · Beachy Beach Real Estate

  • 3783 Payne Lake Road — photo80Active

    $389,000

    5 bd · 4 ba · 3,100 sqft

    3783 Payne Lake Road, Chipley, FL

    Nathan R Lawrence · Legacy Premier Agency 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

  • 2007 Ambassador Court — photoPrice Reduced39Active

    $279,900

    2 bd · 2 ba · 1,333 sqft

    2007 Ambassador Court, Chipley, FL

    Debbie Morton · Bay Living Inc.

  • 1324 Coggin Avenue — photo44Active

    $259,900

    4 bd · 3 ba · 2,736 sqft

    1324 Coggin Avenue, Chipley, FL

    Cindy R Birge · Elite Realty

  • 4069 Ramus Drive — photo27Active

    $252,900

    4 bd · 2 ba · 1,458 sqft

    4069 Ramus Drive, Chipley, FL

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

  • 4066 Ramus Drive — photoPrice Reduced29Active

    $217,400

    3 bd · 2 ba · 1,281 sqft

    4066 Ramus Drive, Chipley, FL

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

  • 1234…6

    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: 2026-09-29 23:20:26 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 2026-09-30 16:26:19 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 31, 2026

    Median sale price
    $113,250$25,250–$238,519 typical range
    Price per sq. ft.
    $137
    Sales
    94
    Paid in cash
    63.8%

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

    Year-over-year
    -50.7%