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3 beds New construction

Homes Under $500K in Chipley, FL

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19 of 139 Listings

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19 of 139 Listings

20Active

Homes Under $500K in Chipley, FL — Page 6

139 listings

Homes Under $500K in Chipley, FL

Hide Map

19 of 139 Listings

Map

Homes Under $500K in Chipley, FL

19 of 139 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

20Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced21Active

$309,459

3 bd · 2 ba · 1,760 sqft

2269 Shenandoah Boulevard, Chipley, FL

Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

Price Reduced19Active

$273,800

3 bd · 2 ba · 1,279 sqft

2272 Rockford Drive, Chipley, FL

Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

20Active

$274,252

3 bd · 2 ba · 1,650 sqft

3984 Quail Court, Chipley, FL

Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

Price Reduced21Active

$299,900

3 bd · 2 ba · 1,760 sqft

3892 Bricknell Avenue, Chipley, FL

Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

Price Reduced20Active

$283,900

3 bd · 2 ba · 1,528 sqft

3884 Bricknell Avenue, Chipley, FL

Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

19Active

$279,068

4 bd · 2 ba · 1,716 sqft

3989 Horizon Avenue, Chipley, FL

Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

Price Reduced19Active

$276,900

3 bd · 2 ba · 1,279 sqft

3900 Bricknell Avenue, Chipley, FL

Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

Price Reduced50Active

$209,900

3 bd · 2 ba · 1,248 sqft

1764 Clayton Road, Chipley, FL

Denise Myers · Elite Realty

18Active

$269,236

3 bd · 2 ba · 1,556 sqft

2209 Chase Street, Chipley, FL

Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

17Active

$271,312

3 bd · 2 ba · 1,556 sqft

2221 Chase Street, Chipley, FL

Sara Iaropoli · Deltona Marketing at Sunny Hills Inc

Price Reduced36Active

$275,000

3 bd · 3 ba · 1,625 sqft

3922 Vistula Drive, Chipley, FL

Whitby D Jerkins · Serhant

Price Reduced26Active

$179,900

3 bd · 2 ba · 1,568 sqft

4326 Moss Hill Road, Chipley, FL

Alyssa R Sato · Keller Williams Success Realty

30Active

$200,000

3 bd · 2 ba · 1,773 sqft

3515 Quail Ridge Drive, Chipley, FL

Chad Millner · Keller Williams Success Realty

Price Reduced46Active

$335,000

3 bd · 2 ba · 1,529 sqft

1730 Firetower Road, Chipley, FL

Eren S Sullivan · Counts Real Estate Group

Price Reduced45Active

$347,000

1 bd · 1 ba · 432 sqft

5491 Highway 77, Chipley, FL

Vic A Jed · CENTURY 21 Commander Realty

Price Reduced50Active

$349,900

4 bd · 2 ba · 1,624 sqft

3243 Quail Ridge Drive, Chipley, FL

Tiffany Hennessy · Hennessy Real Estate Group LLC

1…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: 2026-10-26 06:35:00 UTC

Chipley housing market

September 2026

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.

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.

Your local brokerage

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: 2026-10-26 06:35:00 UTC

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

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.