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Homes Under $400K in Chipley, FL — Page 4

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3 beds New construction

Homes Under $400K in Chipley, FL

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24 of 119 Listings

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24 of 119 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

30Active
$99,900
3 bd · 2 ba · 1,104 sqft
529 N 5th Street, Chipley, FL
Nathan Lawrence · Legacy Premier Agency
32Active
$224,998
3 bd · 2 ba · 1,219 sqft
4183 Luar, Chipley, FL
John R Cunningham · Realty Destination LLC
Price Reduced45Active
$344,900
3 bd · 2 ba · 1,852 sqft
4122 Highland Avenue, Chipley, FL
Cindy R Birge · Elite Realty

22Active
$134,999
3 bd · 2 ba · 1,056 sqft
3382 Lakeshore Drive, Chipley, FL
Seamus J O'neill · SOUTHERN WAY REALTY, INC.
Price Reduced33Active
$139,999
3 bd · 2 ba · 913 sqft
2493 Trailblazer Lane, Chipley, FL
Seamus J O'neill · SOUTHERN WAY REALTY, INC.
Price Reduced38Active
$215,000
3 bd · 2 ba · 1,620 sqft
1804 Ulmer Lane, Chipley, FL
Caitlin F Domer · CENTURY 21 Commander Realty
32Active
$224,998
3 bd · 2 ba · 1,219 sqft
4183 Luar Avenue, Chipley, FL
John Cunningham · Realty Destination LLC
Price Reduced34Active
$274,999
3 bd · 2 ba · 1,502 sqft
1975 Ambassador Court, Chipley, FL
Seamus J O'neill · SOUTHERN WAY REALTY, INC.
51Active
$299,000
3 bd · 2 ba · 1,918 sqft
1130 Timberlane Road, Chipley, FL
Hubert Albisa · Beach Realty of Florida
Price Reduced31Active
$259,900
3 bd · 2 ba · 1,568 sqft
1214 Johnson Avenue, Chipley, FL
Cindy R Birge · Elite Realty
29Active
$199,900
3 bd · 2 ba · 1,800 sqft
1744 Highway 90, Chipley, FL
Sharon Gavin · Creek to Coast Realty, LLC
Price Reduced35Active
$324,900
3 bd · 2 ba · 1,903 sqft
1277 South Boulevard, Chipley, FL
Katherine Cave · Epique Realty Inc
Price Reduced22Active
$330,000
3 bd · 2 ba · 1,368 sqft
3047 Everest Drive, Chipley, FL
Amanda Creamer · World Impact Real Estate
2Active
$79,900
3 bd · 3 ba · 2,283 sqft
1908 Gravel Pit Road, Chipley, FL
Mari Monroe-Garcia · Legacy Premier Agency
Price Reduced37Active
$279,355
5 bd · 3 ba · 2,043 sqft
1994 Ambassador Court, Chipley, FL
Pamela K Hawkins · DR Horton Realty of Emerald Coast, LLC
19Active
$279,900
3 bd · 2 ba · 1,500 sqft
2148 Jensen Place, Chipley, FL
Cari Henry · CENTURY 21 Commander Realty
21Active
$283,956
4 bd · 2 ba · 1,716 sqft
2225 Chase Street, Chipley, FL
Sara Iaropoli · Deltona Marketing at Sunny Hills Inc
1Active
$275,952
3 bd · 2 ba · 1,650 sqft
2081 Babcock Street, Chipley, FL
Sara Iaropoli · Deltona Marketing at Sunny Hills Inc
34Active
$225,000
3 bd · 2 ba · 1,392 sqft
783 West Boulevard, Chipley, FL
Bettie L Slay · Bettie's Country Realty
Price Reduced34Active
$249,990
4 bd · 2 ba · 1,684 sqft
4135 Aquarius Drive, Chipley, FL
Octavia Valencia · WJH Brokerage FL LLC
Price Reduced36Active
$229,999
4 bd · 3 ba · 1,430 sqft
940 Jamie Drive, Chipley, FL
Seamus J O'neill · SOUTHERN WAY REALTY, INC.
Price Reduced20Active
$340,000
3 bd · 2 ba · 1,980 sqft
498 Quail Hollow Blvd, Chipley, FL
Holly DiMemmo · LPT REALTY, LLC
45Active
$199,900
3 bd · 2 ba · 2,084 sqft
2414 Highway 77, Chipley, FL
Cindy R Birge · Elite Realty
Price Reduced36Active
$329,999
4 bd · 2 ba · 1,823 sqft
3995 Quail Avenue, Chipley, FL
Kelly N Lathem · Corcoran Reverie

1…3 4 5

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: 2026-10-05 15:31:53 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 2026-09-28 06:35:14 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.
Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Chipley housing market

August 2026

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%

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

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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

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.

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: 2026-10-05 15:31:53 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 2026-09-28 06:35:14 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.
Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Chipley housing market

August 2026

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%