Airbnb Properties for Sale in Chipley, FL

Looking for a vacation rental investment in Chipley, FL with high ROI ?

Explore a range of newly added short-term rental homes in Chipley, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Chipley, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3047 Everest Drive Chipley, FL Motivated seller, Move-in ready and recent updates, this 3-bedroom, 2-bath home is nestled...	3 beds \| 2 baths \| 1,368 sq.ft.	$330,000	Airbnb cash on cash: 8.24% Traditional cash on cash: 4.83% Airbnb Rental Income: $4189 Traditional Rental Income: $2244 Airbnb ROI: 8.24% Traditional ROI: 4.83%
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.	$400,000	Airbnb cash on cash: 6.9% Traditional cash on cash: 5.13% Airbnb Rental Income: $4189 Traditional Rental Income: $2636 Airbnb ROI: 6.9% Traditional ROI: 5.13%
1730 Firetower Road Chipley, FL Seller offering $5,000 in Closing Costs assistance and Fidelity National Home Warranty. Es...	3 beds \| 2 baths \| 1,529 sq.ft.	$335,000	Airbnb cash on cash: 8.75% Traditional cash on cash: 5.35% Airbnb Rental Income: $4189 Traditional Rental Income: $2232 Airbnb ROI: 8.75% Traditional ROI: 5.35%
2474 Tiller Cemetery Drive Chipley, FL 35 acres, Heated pool, Ponds, abundant wildlife, and room to breathe. This isn't just a pr...	4 beds \| 3 baths \| 1,941 sq.ft.	$599,900	Airbnb cash on cash: 4.93% Traditional cash on cash: 2.42% Airbnb Rental Income: $4916 Traditional Rental Income: $2503 Airbnb ROI: 4.93% Traditional ROI: 2.42%
1186 Pine Forest Road Chipley, FL Tucked away on a generous 17.5-acre parcel, this charming 2,899 SF, 4-bedroom, 2.5-bath ho...	4 beds \| 3 baths \| 2,899 sq.ft.	$529,900	Airbnb cash on cash: 5.82% Traditional cash on cash: 4.01% Airbnb Rental Income: $4916 Traditional Rental Income: $3014 Airbnb ROI: 5.82% Traditional ROI: 4.01%
3256 Highway 77 Chipley, FL Located on 48.42 acres, this spacious 3-bedroom, 2-bathroom home offers 2,385 sq ft of com...	3 beds \| 2 baths \| 2,385 sq.ft.	$559,900	Airbnb cash on cash: 4.91% Traditional cash on cash: 2.65% Airbnb Rental Income: $4189 Traditional Rental Income: $2121 Airbnb ROI: 4.91% Traditional ROI: 2.65%
2527 Frost Lane Chipley, FL Welcome to 2527 Frost Lane in Chipley, a spacious 2-bedroom, 2-bathroom home offering 2,63...	2 beds \| 2 baths \| 2,634 sq.ft.	$429,900	Airbnb cash on cash: 3.69% Traditional cash on cash: 3.58% Airbnb Rental Income: $2702 Traditional Rental Income: $2021 Airbnb ROI: 3.69% Traditional ROI: 3.58%
1712 Shamrock Lane Chipley, FL Seller is offering a home warranty with an acceptable offer for added buyer peace of mind!...	4 beds \| 3 baths \| 2,938 sq.ft.	$439,900	Airbnb cash on cash: 7.86% Traditional cash on cash: 5.56% Airbnb Rental Income: $4916 Traditional Rental Income: $2961 Airbnb ROI: 7.86% Traditional ROI: 5.56%
498 QUAIL HOLLOW Boulevard Chipley, FL New stairs/decks recently added! Welcome to this exceptional custom-built home, where thou...	3 beds \| 2 baths \| 1,980 sq.ft.	$369,900	Airbnb cash on cash: 7.43% Traditional cash on cash: 4.43% Airbnb Rental Income: $4189 Traditional Rental Income: $2259 Airbnb ROI: 7.43% Traditional ROI: 4.43%
3421 Quail Ridge Drive Chipley, FL This has to be one of the nicest waterfront houses in Leisure Lakes, and the only one with...	3 beds \| 3 baths \| 1,890 sq.ft.	$449,900	Airbnb cash on cash: 5.87% Traditional cash on cash: 4.42% Airbnb Rental Income: $4189 Traditional Rental Income: $2693 Airbnb ROI: 5.87% Traditional ROI: 4.42%
3251 Hill Lane Chipley, FL Discover this beautifully maintained 4-bedroom, 2-bathroom home offering 2,046 heated and ...	4 beds \| 2 baths \| 2,046 sq.ft.	$349,999	Airbnb cash on cash: 9.82% Traditional cash on cash: 5.14% Airbnb Rental Income: $4916 Traditional Rental Income: $2370 Airbnb ROI: 9.82% Traditional ROI: 5.14%
849 S 8th Street Chipley, FL Rare find in the heart of Chipley! This spacious 3-bedroom, 2-bath ranch-style brick home ...	3 beds \| 2 baths \| 2,806 sq.ft.	$349,900	Airbnb cash on cash: 8.42% Traditional cash on cash: 5.38% Airbnb Rental Income: $4189 Traditional Rental Income: $2302 Airbnb ROI: 8.42% Traditional ROI: 5.38%
2902 River Lake Drive Chipley, FL Quiet, secluded 3 bedroom 2 bath country style home on 4.5 beautiful acres. 16x18 Covered ...	3 beds \| 2 baths \| 1,632 sq.ft.	$335,000	Airbnb cash on cash: 8.42% Traditional cash on cash: 5.37% Airbnb Rental Income: $4189 Traditional Rental Income: $2339 Airbnb ROI: 8.42% Traditional ROI: 5.37%
661 US-90 Chipley, FL Discover the perfect blend of modern comfort and peaceful country living in this beautiful...	4 beds \| 3 baths \| 2,348 sq.ft.	$459,900	Airbnb cash on cash: 7.54% Traditional cash on cash: 4.55% Airbnb Rental Income: $4916 Traditional Rental Income: $2621 Airbnb ROI: 7.54% Traditional ROI: 4.55%
1277 South Boulevard Chipley, FL Preferred Lender credit $2,000 towards closing costs Beautifully renovated 3BR/2BA hom...	3 beds \| 2 baths \| 1,903 sq.ft.	$324,900	Airbnb cash on cash: 8.38% Traditional cash on cash: 4.83% Airbnb Rental Income: $4189 Traditional Rental Income: $2217 Airbnb ROI: 8.38% Traditional ROI: 4.83%
4122 Highland Avenue Chipley, FL Welcome to this well-maintained home located in the desirable Sunny Hills community, offer...	3 beds \| 2 baths \| 1,852 sq.ft.	$349,900	Airbnb cash on cash: 8.36% Traditional cash on cash: 4.29% Airbnb Rental Income: $4189 Traditional Rental Income: $1964 Airbnb ROI: 8.36% Traditional ROI: 4.29%
2970 Woodymarion Drive Chipley, FL Welcome to your own private waterfront retreat on beautiful Spring Pond. Situated on a 4.7...	3 beds \| 2 baths \| 2,072 sq.ft.	$579,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 3.37% Airbnb Rental Income: $4189 Traditional Rental Income: $2622 Airbnb ROI: 4.63% Traditional ROI: 3.37%
3445 Cardinal Place Chipley, FL This 3-year old home still shines like new in the security gated lake subdivision of Leisu...	3 beds \| 2 baths \| 1,379 sq.ft.	$349,900	Airbnb cash on cash: 8.35% Traditional cash on cash: 4.43% Airbnb Rental Income: $4189 Traditional Rental Income: $2011 Airbnb ROI: 8.35% Traditional ROI: 4.43%
1995 Ambassador Court Chipley, FL Nestled in the quiet community of Sunny Hills, this 2 bedroom ranch home sits on a generou...	2 beds \| 2 baths \| 1,180 sq.ft.	$199,000	Airbnb cash on cash: 8.63% Traditional cash on cash: 6.13% Airbnb Rental Income: $2702 Traditional Rental Income: $1592 Airbnb ROI: 8.63% Traditional ROI: 6.13%
1788 Gap Boulevard Chipley, FL Peaceful Waterfront Retreat on 14.79 Acres Escape to your own private slice of paradise wi...	3 beds \| 2 baths \| 1,414 sq.ft.	$319,000	Airbnb cash on cash: 9.47% Traditional cash on cash: 5.46% Airbnb Rental Income: $4189 Traditional Rental Income: $2101 Airbnb ROI: 9.47% Traditional ROI: 5.46%
4152 Leisure Lakes Drive Chipley, FL Priced to sell and move-in ready, this spacious home on nearly 3 peaceful acres is an incr...	4 beds \| 3 baths \| 2,916 sq.ft.	$369,900	Airbnb cash on cash: 8.9% Traditional cash on cash: 6.36% Airbnb Rental Income: $4916 Traditional Rental Income: $3026 Airbnb ROI: 8.9% Traditional ROI: 6.36%

Vacation Rentals in Chipley

There are 21 vacation rental properties available for sale in the city of Chipley . The median list price of Airbnb properties available for sale in Chipley is $199,780 and the average price per square foot is $114. The cash on cash return on vacation rentals in Chipley is 10.00%. The average monthly short term rental income in Chipley is $4,189.

Chipley, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 21 Airbnb properties available for sale in Chipley.

In 2026, the best neighborhood to buy short term rental property is Chipley.

In September 2026, the average Airbnb occupancy rate in Chipley is 41%.

Airbnb data on vacation rentals in Chipley, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Chipley, FL market insights, guest information and booking details, seasonality trends and historical Chipley, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Chipley, FL

3047 Everest Drive

Chipley, FL

3 beds | 2 baths | 1,368 sq.ft.

$330,000

Airbnb cash on cash: 8.24%

Traditional cash on cash: 4.83%

Airbnb Rental Income: $4189

Traditional Rental Income: $2244

Airbnb ROI: 8.24%

Traditional ROI: 4.83%

3034 Paradise Lakes Road

Chipley, FL

3 beds | 2 baths | 1,392 sq.ft.

$400,000

Airbnb cash on cash: 6.9%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $4189

Traditional Rental Income: $2636

Airbnb ROI: 6.9%

Traditional ROI: 5.13%

1730 Firetower Road

Chipley, FL

3 beds | 2 baths | 1,529 sq.ft.

$335,000

Airbnb cash on cash: 8.75%

Traditional cash on cash: 5.35%

Airbnb Rental Income: $4189

Traditional Rental Income: $2232

Airbnb ROI: 8.75%

Traditional ROI: 5.35%

2474 Tiller Cemetery Drive

Chipley, FL

4 beds | 3 baths | 1,941 sq.ft.

$599,900

Airbnb cash on cash: 4.93%

Traditional cash on cash: 2.42%

Airbnb Rental Income: $4916

Traditional Rental Income: $2503

Airbnb ROI: 4.93%

Traditional ROI: 2.42%

1186 Pine Forest Road

Chipley, FL

4 beds | 3 baths | 2,899 sq.ft.

$529,900

Airbnb cash on cash: 5.82%

Traditional cash on cash: 4.01%

Airbnb Rental Income: $4916

Traditional Rental Income: $3014

Airbnb ROI: 5.82%

Traditional ROI: 4.01%

3256 Highway 77

Chipley, FL

3 beds | 2 baths | 2,385 sq.ft.

$559,900

Airbnb cash on cash: 4.91%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $4189

Traditional Rental Income: $2121

Airbnb ROI: 4.91%

Traditional ROI: 2.65%

2527 Frost Lane

Chipley, FL

2 beds | 2 baths | 2,634 sq.ft.

$429,900

Airbnb cash on cash: 3.69%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $2702

Traditional Rental Income: $2021

Airbnb ROI: 3.69%

Traditional ROI: 3.58%

1712 Shamrock Lane

Chipley, FL

4 beds | 3 baths | 2,938 sq.ft.

$439,900

Airbnb cash on cash: 7.86%

Traditional cash on cash: 5.56%

Airbnb Rental Income: $4916

Traditional Rental Income: $2961

Airbnb ROI: 7.86%