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
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: 7.11% Traditional cash on cash: 3.03% Airbnb Rental Income: $4189 Traditional Rental Income: $1800 Airbnb ROI: 7.11% 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: 7.15% Traditional cash on cash: 5.42% Airbnb Rental Income: $4189 Traditional Rental Income: $2655 Airbnb ROI: 7.15% Traditional ROI: 5.42%
1264 Plum Avenue Chipley, FL Welcome to peaceful country living, just minutes from the conveniences of downtown Chipley...	3 beds \| 2 baths \| N/A	$325,000	Airbnb cash on cash: 8.62% Traditional cash on cash: 3.97% Airbnb Rental Income: $4189 Traditional Rental Income: $1881 Airbnb ROI: 8.62% Traditional ROI: 3.97%
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 \| N/A	$299,999	Airbnb cash on cash: 9.44% Traditional cash on cash: 5.03% Airbnb Rental Income: $4189 Traditional Rental Income: $2056 Airbnb ROI: 9.44% 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 \| N/A	$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: 7.7% Traditional cash on cash: 5.98% Airbnb Rental Income: $4189 Traditional Rental Income: $2706 Airbnb ROI: 7.7% Traditional ROI: 5.98%
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: 9.8% Traditional cash on cash: 7.07% Airbnb Rental Income: $4189 Traditional Rental Income: $2491 Airbnb ROI: 9.8% Traditional ROI: 7.07%
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: 7.44% Traditional cash on cash: 5.09% Airbnb Rental Income: $4189 Traditional Rental Income: $2445 Airbnb ROI: 7.44% 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%
3034 Paradise Lakes Road Chipley, FL Get your slice of paradise on Paradise Lake Road. This beautiful, custom-built waterfront ...	3 beds \| 2 baths \| N/A	$395,000	Airbnb cash on cash: 7% Traditional cash on cash: 3.71% Airbnb Rental Income: $4189 Traditional Rental Income: $2083 Airbnb ROI: 7% Traditional ROI: 3.71%
1371 Deadening Road Chipley, FL Waterfront Retreat at Econfina Springs Wildlife Management - Nature Lover's / Sportsman's ...	3 beds \| 2 baths \| N/A	$325,000	Airbnb cash on cash: 9.31% Traditional cash on cash: 5.67% Airbnb Rental Income: $4189 Traditional Rental Income: $2189 Airbnb ROI: 9.31% Traditional ROI: 5.67%
490 Quail Hollow Boulevard Chipley, FL Oasis in the 'Hills! This property has everything you could ever need and is priced below ...	4 beds \| 2 baths \| N/A	$440,000	Airbnb cash on cash: 8.08% Traditional cash on cash: 3.87% Airbnb Rental Income: $4916 Traditional Rental Income: $2175 Airbnb ROI: 8.08% Traditional ROI: 3.87%
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: 7.33% Traditional cash on cash: 4.09% Airbnb Rental Income: $4189 Traditional Rental Income: $2114 Airbnb ROI: 7.33% Traditional ROI: 4.09%
5192 Pine Ridge Drive Chipley, FL Gorgeous lakefront, brick home sitting on over 4 acres in desirable community! We have the...	3 beds \| 2 baths \| N/A	$489,900	Airbnb cash on cash: 5.66% Traditional cash on cash: 3.71% Airbnb Rental Income: $4189 Traditional Rental Income: $2409 Airbnb ROI: 5.66% Traditional ROI: 3.71%
1730 Firetower Road Chipley, FL Getaway in the country! This 3br/2ba block home has so much to offer: Metal roof, HVAC 202...	3 beds \| 2 baths \| N/A	$400,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 3.4% Airbnb Rental Income: $4189 Traditional Rental Income: $1882 Airbnb ROI: 7.19% Traditional ROI: 3.4%
2649 Bonnett Pond Road Chipley, FL Looking for a hunting or fishing lodge? Investment rental property? You have found it!! No...	3 beds \| 2 baths \| N/A	$360,000	Airbnb cash on cash: 8.08% Traditional cash on cash: 3.82% Airbnb Rental Income: $4189 Traditional Rental Income: $1864 Airbnb ROI: 8.08% Traditional ROI: 3.82%
4505 Leisure Lakes Drive Chipley, FL Enjoy serene country living in the gated Leisure Lakes community with this stunning 2021 w...	3 beds \| 2 baths \| N/A	$325,000	Airbnb cash on cash: 8.75% Traditional cash on cash: 6.08% Airbnb Rental Income: $4189 Traditional Rental Income: $2487 Airbnb ROI: 8.75% Traditional ROI: 6.08%
3965 Stillwater Drive Chipley, FL Lakefront Living with Endless Possibilities! Nestled on the shores of stunning Lucas Lake-...	3 beds \| 2 baths \| N/A	$340,000	Airbnb cash on cash: 8.6% Traditional cash on cash: 4.83% Airbnb Rental Income: $4189 Traditional Rental Income: $2095 Airbnb ROI: 8.6% Traditional ROI: 4.83%
1771 Sorrells Road Chipley, FL Welcome home to peaceful country living with modern comfort and small-town charm! This bea...	3 beds \| 2 baths \| N/A	$325,000	Airbnb cash on cash: 9.38% Traditional cash on cash: 5.88% Airbnb Rental Income: $4189 Traditional Rental Income: $2234 Airbnb ROI: 9.38% Traditional ROI: 5.88%
2437 Gilberts Mill Road Chipley, FL Looking for peaceful country living with room to roam? This inviting property offers the p...	2 beds \| 2 baths \| N/A	$209,900	Airbnb cash on cash: 8.49% Traditional cash on cash: 7.5% Airbnb Rental Income: $2660 Traditional Rental Income: $1831 Airbnb ROI: 8.49% Traditional ROI: 7.5%
3289 Lucas Lake Road Chipley, FL Welcome to 3289 Lucas Lake Rd, the 7 acre homestead on Stewart Lake that meets all of the ...	3 beds \| 2 baths \| N/A	$475,000	Airbnb cash on cash: 5.75% Traditional cash on cash: 4.2% Airbnb Rental Income: $4189 Traditional Rental Income: $2615 Airbnb ROI: 5.75% Traditional ROI: 4.2%

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 $235,000 and the average price per square foot is $136. The cash on cash return on vacation rentals in Chipley is 11.00%. 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 November 2025, the average Airbnb occupancy rate in Chipley is 52%.

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

561 Lakepointe Drive

Chipley, FL

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

$392,700

Airbnb cash on cash: 7.11%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $4189

Traditional Rental Income: $1800

Airbnb ROI: 7.11%

Traditional ROI: 3.03%

1421 Gainer Road

Chipley, FL

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

$399,900

Airbnb cash on cash: 7.15%

Traditional cash on cash: 5.42%

Airbnb Rental Income: $4189

Traditional Rental Income: $2655

Airbnb ROI: 7.15%

Traditional ROI: 5.42%

1264 Plum Avenue

Chipley, FL

3 beds | 2 baths | N/A

$325,000

Airbnb cash on cash: 8.62%

Traditional cash on cash: 3.97%

Airbnb Rental Income: $4189

Traditional Rental Income: $1881

Airbnb ROI: 8.62%

Traditional ROI: 3.97%

4367 Carey Boulevard

Chipley, FL

3 beds | 3 baths | N/A

$299,999

Airbnb cash on cash: 9.44%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $4189

Traditional Rental Income: $2056

Airbnb ROI: 9.44%

Traditional ROI: 5.03%

4478 Hancock Court

Chipley, FL

2 beds | 2 baths | N/A

$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: 7.7%

Traditional cash on cash: 5.98%

Airbnb Rental Income: $4189

Traditional Rental Income: $2706

Airbnb ROI: 7.7%

Traditional ROI: 5.98%

4131 Merrifield Court

Chipley, FL

3 beds | 3 baths | 2,000 sq.ft.

$314,900

Airbnb cash on cash: 9.8%

Traditional cash on cash: 7.07%

Airbnb Rental Income: $4189

Traditional Rental Income: $2491

Airbnb ROI: 9.8%

Traditional ROI: 7.07%

1701 Nearing Hills Circle

Chipley, FL

3 beds | 2 baths | 2,911 sq.ft.

$389,500

Airbnb cash on cash: 7.44%

Traditional cash on cash: 5.09%

Airbnb Rental Income: $4189

Traditional Rental Income: $2445

Airbnb ROI: 7.44%