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 Dr Chipley, FL Set on a full acre in the desirable Lakepointe subdivision, this well-maintained home offe...	3 beds \| 2 baths \| 1,642 sq.ft.	$384,900	Airbnb cash on cash: 7.21% Traditional cash on cash: 3.05% Airbnb Rental Income: $4189 Traditional Rental Income: $1800 Airbnb ROI: 7.21% Traditional ROI: 3.05%
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 Ave Chipley, FL Welcome to peaceful country living, just minutes from the conveniences of downtown Chipley...	3 beds \| 2 baths \| 1,425 sq.ft.	$315,000	Airbnb cash on cash: 8.78% Traditional cash on cash: 4.06% Airbnb Rental Income: $4189 Traditional Rental Income: $1881 Airbnb ROI: 8.78% Traditional ROI: 4.06%
4367 Carey Blvd Chipley, FL Brand New Home in Sunny Hills, not far from the Florida Panhandle's best offerings of whit...	3 beds \| 2 baths \| 1,680 sq.ft.	$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 Ct Chipley, FL Seller offering $5,000 in closing cost assistance with accepted offer! RENOVATED DREAM! Th...	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%
3965 Crystal Lake Dr Chipley, FL Here's your chance to live on a slice of paradise! Enjoy relaxing on the deck to get some ...	3 beds \| N/A baths \| 2,290 sq.ft.	$580,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 2.14% Airbnb Rental Income: $4189 Traditional Rental Income: $2110 Airbnb ROI: 4.34% Traditional ROI: 2.14%
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%
4812 Derby Drive Chipley, FL 'CURRENTLY UNDER CONTRACT, SELLER WILL CONSIDER BACKUP OFFERS' One owner, custom built hom...	3 beds \| 2 baths \| 1,489 sq.ft.	$350,000	Airbnb cash on cash: 8.64% Traditional cash on cash: 6.2% Airbnb Rental Income: $4189 Traditional Rental Income: $2499 Airbnb ROI: 8.64% Traditional ROI: 6.2%
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 Rd Chipley, FL Get your slice of paradise on Paradise Lake Road. This beautiful, custom-built waterfront ...	3 beds \| 2 baths \| 1,392 sq.ft.	$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 Rd Chipley, FL Waterfront Retreat at Econfina Springs Wildlife Management - Nature Lover's / Sportsman's ...	3 beds \| 2 baths \| 1,484 sq.ft.	$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 Blvd Chipley, FL Oasis in the 'Hills! This property has everything you could ever need and is priced below ...	4 beds \| 2 baths \| 2,304 sq.ft.	$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 \| 1,980 sq.ft.	$479,900	Airbnb cash on cash: 5.79% Traditional cash on cash: 3.8% Airbnb Rental Income: $4189 Traditional Rental Income: $2409 Airbnb ROI: 5.79% Traditional ROI: 3.8%
1730 Firetower Rd Chipley, FL Getaway in the country! This 3br/2ba block home has so much to offer: Metal roof, HVAC 202...	3 beds \| 2 baths \| 2,030 sq.ft.	$385,000	Airbnb cash on cash: 7.5% Traditional cash on cash: 3.57% Airbnb Rental Income: $4189 Traditional Rental Income: $1882 Airbnb ROI: 7.5% Traditional ROI: 3.57%
2649 Bonnett Pond Rd Chipley, FL Looking for a hunting or fishing lodge? Investment rental property? You have found it!! No...	3 beds \| 2 baths \| 1,522 sq.ft.	$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 \| 1,980 sq.ft.	$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 CURRETLY UNDER CONTRACT, SELLER WILL CONSIDER TAKING A BACKUP CONTRACT Lakefront Living wi...	3 beds \| 2 baths \| 1,392 sq.ft.	$320,000	Airbnb cash on cash: 9.2% Traditional cash on cash: 5.18% Airbnb Rental Income: $4189 Traditional Rental Income: $2095 Airbnb ROI: 9.2% Traditional ROI: 5.18%
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 Rd Chipley, FL Looking for peaceful country living with room to roam? This inviting property offers the p...	2 beds \| 2 baths \| 1,080 sq.ft.	$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%
853 1st St Chipley, FL Brick home in the heart of Chipley and close to schools and shopping. Two spacious bedroom...	2 beds \| 2 baths \| 1,917 sq.ft.	$180,000	Airbnb cash on cash: 9.04% Traditional cash on cash: 8.85% Airbnb Rental Income: $2660 Traditional Rental Income: $1995 Airbnb ROI: 9.04% Traditional ROI: 8.85%
652 N 2nd St Chipley, FL Experience the perfect blend of small-town charm and expansive outdoor space with this stu...	3 beds \| 2 baths \| 2,284 sq.ft.	$319,900	Airbnb cash on cash: 8.55% Traditional cash on cash: 2.1% Airbnb Rental Income: $4189 Traditional Rental Income: $1362 Airbnb ROI: 8.55% Traditional ROI: 2.1%
0 New Prospect Rd Chipley, FL 0 New Prospect Rd, Chipley, FL 32428 \| Other	N/A beds \| N/A baths \| 1,146 sq.ft.	$294,500	Airbnb cash on cash: 9.69% Traditional cash on cash: 0.07% Airbnb Rental Income: $4189 Traditional Rental Income: $633 Airbnb ROI: 9.69% Traditional ROI: 0.07%

Vacation Rentals in Chipley

There are 82 vacation rental properties available for sale in the city of Chipley . The median list price of Airbnb properties available for sale in Chipley is $228,650 and the average price per square foot is $139. 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 82 Airbnb properties available for sale in Chipley.

In February 2026, the average Airbnb occupancy rate in Chipley is 35%.

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 Dr

Chipley, FL

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

$384,900

Airbnb cash on cash: 7.21%

Traditional cash on cash: 3.05%

Airbnb Rental Income: $4189

Traditional Rental Income: $1800

Airbnb ROI: 7.21%

Traditional ROI: 3.05%

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 Ave

Chipley, FL

3 beds | 2 baths | 1,425 sq.ft.

$315,000

Airbnb cash on cash: 8.78%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $4189

Traditional Rental Income: $1881

Airbnb ROI: 8.78%

Traditional ROI: 4.06%

4367 Carey Blvd

Chipley, FL

3 beds | 2 baths | 1,680 sq.ft.

$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 Ct

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%

3965 Crystal Lake Dr

Chipley, FL

3 beds | N/A baths | 2,290 sq.ft.

$580,000

Airbnb cash on cash: 4.34%

Traditional cash on cash: 2.14%

Airbnb Rental Income: $4189

Traditional Rental Income: $2110

Airbnb ROI: 4.34%

Traditional ROI: 2.14%

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%