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Homes Under $500K in Chipley, FL — Page 5

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3 beds New construction

Homes Under $500K in Chipley, FL

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22 of 128 Listings

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22 of 128 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

40Active
$439,000
3 bd · 3 ba · 2,525 sqft
1453 Hwy 277, Chipley, FL
Sheila L Barbee · Barbee Realty Inc
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.

54Active
$450,000
4 bd · 4 ba · 3,745 sqft
700 2nd Street, Chipley, FL
Justin Raley · Think Real Estate
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
Price Reduced74Active
$424,900
4 bd · 3 ba · 2,938 sqft
1712 Shamrock Lane, Chipley, FL
Denise Myers · Elite Realty
Price Reduced46Active
$399,999
4 bd · 3 ba · 2,860 sqft
1012 Carlisle Road, Chipley, FL
Seamus J O'neill · SOUTHERN WAY REALTY, INC.
Price Reduced42Active
$269,485
4 bd · 2 ba · 2,897 sqft
807 Maple Street, Chipley, FL
Paul T LaCourse · Anchor Realty Florida
Price Reduced54Active
$375,000
2 bd · 2 ba · 1,500 sqft
434 Tinker Lane, Chipley, FL
Leigh Clark · Elite Realty
Price Reduced40Active
$225,000
3 bd · 2 ba · 1,404 sqft
2442 Pinewood Drive, Chipley, FL
Jessica J Albritton · Beachy Beach Real Estate
Price Reduced45Active
$336,000
4 bd · 4 ba · 3,494 sqft
656 4th Street, Chipley, FL
Seamus J O'neill · SOUTHERN WAY REALTY, INC.
75Active
$489,000
4 bd · 3 ba · 2,899 sqft
1186 Pine Forest Road, Chipley, FL
Skye D Goldstein · EXP Realty LLC
39Active
$285,000
3 bd · 2 ba · 1,939 sqft
2199 Sunny Hills Boulevard, Chipley, FL
Paul D Gibney · Corcoran Reverie SRB
21Active
$125,000
4 bd · 2 ba · 1,371 sqft
1304 Kay Avenue, Chipley, FL
Dana L Panichella · American Gold Realty
18Active
$293,344
4 bd · 2 ba · 1,728 sqft
2205 Chase Street, Chipley, FL
Sara Iaropoli · Deltona Marketing at Sunny Hills Inc
20Active
$278,848
4 bd · 2 ba · 1,728 sqft
2212 Chase Street, Chipley, FL
Sara Iaropoli · Deltona Marketing at Sunny Hills Inc
Price Reduced37Active
$266,999
4 bd · 2 ba · 1,768 sqft
872 1st Street, Chipley, FL
Seamus J O'neill · SOUTHERN WAY REALTY, INC.
Price Reduced21Active
$184,900
3 bd · 1 ba · 1,198 sqft
226 Highway 77, Chipley, FL
Wanda Raney · 850 Sunshine Realty
Price Reduced19Active
$99,000
1 bd · 1 ba · 616 sqft
1160 Chance Road, Chipley, FL
Joel Jadofsky · Keller Williams Realty Emerald
Price Reduced24Active
$189,000
4 bd · 2 ba · 2,299 sqft
768 Main Street, Chipley, FL
Gary L Johns · AMERICAN REALTY of Bay Co, Inc

1…4 5 6

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 2026-10-03 14:34:10 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 2026-10-03 14:34:10 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

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%

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas