Real Estate Investment Properties for Sale in Chipley, FL

Looking for investment property in Chipley, FL with high ROI ?

Explore a variety of short-term homes & houses in Chipley, FL. Invest wisely with VRBO & Chipley, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Chipley, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
561 Lakepointe Drive Chipley, FL Looking to live in the highly sought after area of Lake Pointe Subdivsion! This is your ch...	3 beds \| 2 baths \| 1,642 sq.ft.	$392,700	Airbnb cash on cash: 1.71% Traditional cash on cash: 3.03% Airbnb Rental Income: $1801 Traditional Rental Income: $1800 Airbnb ROI: 1.71% Traditional ROI: 3.03%
1421 Gainer Road Chipley, FL Welcome to this beautiful brick home perfectly situated just minutes from Walmart, I-10, a...	3 beds \| 3 baths \| 2,399 sq.ft.	$399,900	Airbnb cash on cash: 1.84% Traditional cash on cash: 5.42% Airbnb Rental Income: $1801 Traditional Rental Income: $2655 Airbnb ROI: 1.84% Traditional ROI: 5.42%
3068 Woodymarion Drive Chipley, FL Waterfront living can become your reality!! Escape to tranquility in this beautiful 3-bedr...	3 beds \| 2 baths \| 1,650 sq.ft.	$285,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 7.11% Airbnb Rental Income: $1801 Traditional Rental Income: $2314 Airbnb ROI: 3.38% Traditional ROI: 7.11%
1380 Watts Avenue Chipley, FL Welcome to this charming, move-in ready three-bedroom home perfectly situated on a corner ...	3 beds \| 2 baths \| 1,480 sq.ft.	$234,900	Airbnb cash on cash: 3.72% Traditional cash on cash: 7.08% Airbnb Rental Income: $1801 Traditional Rental Income: $2058 Airbnb ROI: 3.72% Traditional ROI: 7.08%
4367 Carey Boulevard Chipley, FL Brand New Home in Sunny Hills, not far from the Florida Panhandle's best offerings of whit...	3 beds \| 3 baths \| 1,680 sq.ft.	$299,999	Airbnb cash on cash: 2.4% Traditional cash on cash: 5.03% Airbnb Rental Income: $1801 Traditional Rental Income: $2056 Airbnb ROI: 2.4% Traditional ROI: 5.03%
4478 Hancock Court Chipley, FL R E N O V A T E D D R E A M!This 2 bed, 2 bath 1374 square foot home has charm, character,...	2 beds \| 2 baths \| 1,374 sq.ft.	$235,000	Airbnb cash on cash: 7.31% Traditional cash on cash: 6.06% Airbnb Rental Income: $2660 Traditional Rental Income: $1750 Airbnb ROI: 7.31% Traditional ROI: 6.06%
3375 Crystal Lake Drive Chipley, FL Welcome to 3375 Crystal Lake Drive, a rare opportunity to own a serene waterfront retreat ...	3 beds \| 3 baths \| 1,572 sq.ft.	$369,900	Airbnb cash on cash: 1.96% Traditional cash on cash: 5.98% Airbnb Rental Income: $1801 Traditional Rental Income: $2706 Airbnb ROI: 1.96% Traditional ROI: 5.98%
4936 Grassy Pond Road Chipley, FL Welcome to Monarch Ranch in Grassy Pond Ranches: Private Oasis with Two Homes, Equestrian ...	3 beds \| 3 baths \| 2,496 sq.ft.	$699,900	Airbnb cash on cash: 0.54% Traditional cash on cash: 8.26% Airbnb Rental Income: $1801 Traditional Rental Income: $6352 Airbnb ROI: 0.54% Traditional ROI: 8.26%
4131 Merrifield Court Chipley, FL Introducing this splendid newly constructed 2,000 square foot residence, perfectly positio...	3 beds \| 3 baths \| 2,000 sq.ft.	$314,900	Airbnb cash on cash: 3.09% Traditional cash on cash: 7.07% Airbnb Rental Income: $1801 Traditional Rental Income: $2491 Airbnb ROI: 3.09% Traditional ROI: 7.07%
3835 Highway 77 Chipley, FL Welcome to this custom-built brick home, occupied by the original owner and builder, nestl...	5 beds \| 2 baths \| 2,410 sq.ft.	$610,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.86% Airbnb Rental Income: $null Traditional Rental Income: $2971 Airbnb ROI: N/A Traditional ROI: 3.86%
2789 Summer Drive Chipley, FL Luxury Lakefront Retreat on 3.6 Acres \| 2789 Summer Drive, Chipley, FLWelcome to your priv...	3 beds \| 3 baths \| 2,324 sq.ft.	$750,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 3.53% Airbnb Rental Income: $1801 Traditional Rental Income: $3582 Airbnb ROI: 0.29% Traditional ROI: 3.53%
1509 Southern Way Chipley, FL Tucked away on 10 acres of serene, wooded privacy, this beautifully renovated double-wide ...	3 beds \| 3 baths \| 1,440 sq.ft.	$270,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 6.02% Airbnb Rental Income: $1801 Traditional Rental Income: $1942 Airbnb ROI: 3.55% Traditional ROI: 6.02%
1701 Nearing Hills Circle Chipley, FL Situated on a large lot this beautiful cedar home has a feel about it that feels like you ...	3 beds \| 2 baths \| 2,911 sq.ft.	$389,500	Airbnb cash on cash: 1.99% Traditional cash on cash: 5.09% Airbnb Rental Income: $1801 Traditional Rental Income: $2445 Airbnb ROI: 1.99% Traditional ROI: 5.09%
1733 Salem Drive Chipley, FL Fresh, Fabulous, and Full of Fun - Your Dream Home Awaits! Welcome to your perfect blend o...	2 beds \| 2 baths \| 1,241 sq.ft.	$184,900	Airbnb cash on cash: 9.91% Traditional cash on cash: 7.35% Airbnb Rental Income: $2660 Traditional Rental Income: $1578 Airbnb ROI: 9.91% Traditional ROI: 7.35%
804 8th Street Chipley, FL Discover the perfect blend of charm and convenience with this delightful Florida cottage, ...	3 beds \| 2 baths \| 1,428 sq.ft.	$169,000	Airbnb cash on cash: 5.69% Traditional cash on cash: 9.32% Airbnb Rental Income: $1801 Traditional Rental Income: $1897 Airbnb ROI: 5.69% Traditional ROI: 9.32%
576 Martin Luther King Drive Chipley, FL Welcome home to this charming 3-bedroom, 1-bath brick home in the city of Chipley, conveni...	3 beds \| 1 baths \| 1,343 sq.ft.	$174,999	Airbnb cash on cash: 6.04% Traditional cash on cash: 6.93% Airbnb Rental Income: $1801 Traditional Rental Income: $1459 Airbnb ROI: 6.04% Traditional ROI: 6.93%
3515 Quail Ridge Drive Chipley, FL Back on the market with price improvement, $29,000 less than recent bank valuation! This L...	3 beds \| 2 baths \| 1,773 sq.ft.	$210,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 9.63% Airbnb Rental Income: $1801 Traditional Rental Income: $2293 Airbnb ROI: 4.7% Traditional ROI: 9.63%
1764 Clayton Road Chipley, FL Just What You've Been Looking For - Fully Furnished & Move-In Ready! This charming double-...	3 beds \| 2 baths \| 1,248 sq.ft.	$260,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 5.28% Airbnb Rental Income: $1801 Traditional Rental Income: $1676 Airbnb ROI: 3.8% Traditional ROI: 5.28%
3034 Paradise Lakes Road Chipley, FL Get your slice of paradise on Paradise Lake Road. This beautiful, custom-built waterfront ...	3 beds \| 2 baths \| 1,392 sq.ft.	$450,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 3.14% Airbnb Rental Income: $1801 Traditional Rental Income: $2083 Airbnb ROI: 1.31% Traditional ROI: 3.14%
632 Hideaway Drive Chipley, FL This property located at 632 Hideaway, is nestled in a quiet little area within the City L...	3 beds \| 2 baths \| 1,056 sq.ft.	$155,000	Airbnb cash on cash: 6.85% Traditional cash on cash: 8.38% Airbnb Rental Income: $1801 Traditional Rental Income: $1539 Airbnb ROI: 6.85% Traditional ROI: 8.38%
2004 Old Bonifay Road Chipley, FL Welcome to 2004 Old Bonifay Road -- a newly updated 3-bedroom, 2-bathroom home situated on...	3 beds \| 2 baths \| 1,296 sq.ft.	$219,900	Airbnb cash on cash: 4.69% Traditional cash on cash: 6.55% Airbnb Rental Income: $1801 Traditional Rental Income: $1700 Airbnb ROI: 4.69% Traditional ROI: 6.55%
261 Hero Road Chipley, FL PRICE REDUCTION!!! Rare Opportunity!!! 39 acres in a rural setting, featuring a single wid...	3 beds \| 2 baths \| 1,252 sq.ft.	$265,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 4.85% Airbnb Rental Income: $1801 Traditional Rental Income: $1591 Airbnb ROI: 3.73% Traditional ROI: 4.85%
1371 Deadening Road Chipley, FL Waterfront Retreat at Econfina Springs Wildlife Management - Nature Lover's / Sportman's D...	3 beds \| 2 baths \| 1,484 sq.ft.	$350,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 5.2% Airbnb Rental Income: $1801 Traditional Rental Income: $2189 Airbnb ROI: 2.53% Traditional ROI: 5.2%
3803 Crystal Lake Drive Drive Chipley, FL Welcome to 3803 Crystal Lake Drive, a premier lakefront property offering refined living. ...	3 beds \| 4 baths \| 3,744 sq.ft.	$899,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 3.27% Airbnb Rental Income: $1801 Traditional Rental Income: $3880 Airbnb ROI: 0.2% Traditional ROI: 3.27%
490 Quail Hollow Boulevard Chipley, FL Oasis in the 'Hills! This property has everything you could ever need. The over 2,300sf pr...	4 beds \| 2 baths \| 2,304 sq.ft.	$450,000	Airbnb cash on cash: 7.88% Traditional cash on cash: 3.77% Airbnb Rental Income: $4916 Traditional Rental Income: $2175 Airbnb ROI: 7.88% Traditional ROI: 3.77%
1544 Highway 277 Chipley, FL BACK ON THE MARKET - NO FAULT OF SELLER - Just a few miles outside of town, this beautiful...	3 beds \| 3 baths \| 1,716 sq.ft.	$324,900	Airbnb cash on cash: 2.7% Traditional cash on cash: 4.92% Airbnb Rental Income: $1801 Traditional Rental Income: $1992 Airbnb ROI: 2.7% Traditional ROI: 4.92%
2094 Morven Street Chipley, FL Fantastic Opportunity in Desirable Sunny Hills Community! Welcome to this beautifully main...	3 beds \| 2 baths \| 1,498 sq.ft.	$239,900	Airbnb cash on cash: 3.87% Traditional cash on cash: 6.15% Airbnb Rental Income: $1801 Traditional Rental Income: $1831 Airbnb ROI: 3.87% Traditional ROI: 6.15%
894 Haley Drive Chipley, FL Incredible Dual Property Opportunity with POOL & Workshop - Only $399,000!!!! 894 Haley...	3 beds \| 3 baths \| 2,389 sq.ft.	$399,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 4.99% Airbnb Rental Income: $1801 Traditional Rental Income: $2606 Airbnb ROI: 1.54% Traditional ROI: 4.99%
3359 Antler Trail Chipley, FL 'CURRENTLY UNDER CONTRACT, SELLER WILL CONSIDER BACKUP OFFERS' This gorgeous rustic home l...	3 beds \| 2 baths \| 1,785 sq.ft.	$389,900	Airbnb cash on cash: 1.89% Traditional cash on cash: 4.09% Airbnb Rental Income: $1801 Traditional Rental Income: $2114 Airbnb ROI: 1.89% Traditional ROI: 4.09%
1904 Sunny Hills Boulevard Chipley, FL New Construction in Sunny Hills! This beautiful home features an open floor plan with natu...	3 beds \| 2 baths \| 1,189 sq.ft.	$215,000	Airbnb cash on cash: 4.93% Traditional cash on cash: 7.35% Airbnb Rental Income: $1801 Traditional Rental Income: $1805 Airbnb ROI: 4.93% Traditional ROI: 7.35%
5080 Pine Ridge Dr Chipley, FL Experience the ultimate of tranquil living in this custom-built waterfront home, perfectly...	3 beds \| 3 baths \| 1,831 sq.ft.	$439,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 5.18% Airbnb Rental Income: $1801 Traditional Rental Income: $2830 Airbnb ROI: 1.48% Traditional ROI: 5.18%

Real Estate investment in Chipley, FL

There are 31 properties for sale in the city of Chipley . The median list price in Chipley is $260,000 and the average price per square foot is $149. In September 2025, the average monthly cash on cash return in Chipley is 6.00%. The average monthly rental income in Chipley is $1,992.

Chipley, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 31 investment properties available for sale in Chipley.

In 2025, the best neighborhood to buy investment property is Chipley.

The ROI for Long-Term is higher than the Short-Term in Chipley with average rental income of $1,992.

Your search for investment property begins and ends here

Investment Property for Sale in Chipley, FL

561 Lakepointe Drive

Chipley, FL

3 beds | 2 baths | 1,642 sq.ft.

$392,700

Airbnb cash on cash: 1.71%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $1801

Traditional Rental Income: $1800

Airbnb ROI: 1.71%

Traditional ROI: 3.03%

1421 Gainer Road

Chipley, FL

3 beds | 3 baths | 2,399 sq.ft.

$399,900

Airbnb cash on cash: 1.84%

Traditional cash on cash: 5.42%

Airbnb Rental Income: $1801

Traditional Rental Income: $2655

Airbnb ROI: 1.84%

Traditional ROI: 5.42%

3068 Woodymarion Drive

Chipley, FL

3 beds | 2 baths | 1,650 sq.ft.

$285,000

Airbnb cash on cash: 3.38%

Traditional cash on cash: 7.11%

Airbnb Rental Income: $1801

Traditional Rental Income: $2314

Airbnb ROI: 3.38%

Traditional ROI: 7.11%

1380 Watts Avenue

Chipley, FL

3 beds | 2 baths | 1,480 sq.ft.

$234,900

Airbnb cash on cash: 3.72%

Traditional cash on cash: 7.08%

Airbnb Rental Income: $1801

Traditional Rental Income: $2058

Airbnb ROI: 3.72%

Traditional ROI: 7.08%

4367 Carey Boulevard

Chipley, FL

3 beds | 3 baths | 1,680 sq.ft.

$299,999

Airbnb cash on cash: 2.4%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $1801

Traditional Rental Income: $2056

Airbnb ROI: 2.4%

Traditional ROI: 5.03%

4478 Hancock Court

Chipley, FL

2 beds | 2 baths | 1,374 sq.ft.

$235,000

Airbnb cash on cash: 7.31%

Traditional cash on cash: 6.06%

Airbnb Rental Income: $2660

Traditional Rental Income: $1750

Airbnb ROI: 7.31%

Traditional ROI: 6.06%

3375 Crystal Lake Drive

Chipley, FL

3 beds | 3 baths | 1,572 sq.ft.

$369,900

Airbnb cash on cash: 1.96%

Traditional cash on cash: 5.98%

Airbnb Rental Income: $1801

Traditional Rental Income: $2706

Airbnb ROI: 1.96%

Traditional ROI: 5.98%

4936 Grassy Pond Road

Chipley, FL

3 beds | 3 baths | 2,496 sq.ft.

$699,900

Airbnb cash on cash: 0.54%

Traditional cash on cash: 8.26%

Airbnb Rental Income: $1801

Traditional Rental Income: $6352

Airbnb ROI: 0.54%