Airbnb Properties for Sale in Chesapeake, VA

Looking for a vacation rental investment in Chesapeake, VA with high ROI ?

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

Airbnb For Sale in Chesapeake, VA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1408 Ashton Street Chesapeake, VA This updated 4-bed, 3-bath Chesapeake home features new laminate and carpet flooring throu...	4 beds \| 3 baths \| 1,900 sq.ft.	$369,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 5.21% Airbnb Rental Income: $3312 Traditional Rental Income: $2539 Airbnb ROI: 5.3% Traditional ROI: 5.21%
4019 Sea Cliff Road Chesapeake, VA Welcome to 4019 Sea Cliff Rd , a beautifully refreshed home in a highly sought-after area ...	4 beds \| 2 baths \| 1,751 sq.ft.	$350,000	Airbnb cash on cash: 5.73% Traditional cash on cash: 4.74% Airbnb Rental Income: $3312 Traditional Rental Income: $2246 Airbnb ROI: 5.73% Traditional ROI: 4.74%
1409 Debbs Lane Chesapeake, VA Nicely maintained ranch home in popular Greenbrier. Lots to like here including three dece...	3 beds \| 2 baths \| 1,500 sq.ft.	$367,500	Airbnb cash on cash: 3.91% Traditional cash on cash: 3.77% Airbnb Rental Income: $2762 Traditional Rental Income: $2065 Airbnb ROI: 3.91% Traditional ROI: 3.77%
2115 Rocky Point Run #A Chesapeake, VA Welcome home to a well-kept first-floor condominium in the centrally located Greenbrier ar...	2 beds \| 1 baths \| 822 sq.ft.	$196,500	Airbnb cash on cash: 5.45% Traditional cash on cash: 5.18% Airbnb Rental Income: $2005 Traditional Rental Income: $1431 Airbnb ROI: 5.45% Traditional ROI: 5.18%
4044 River Breeze Circle Chesapeake, VA This beautiful well maintained home offers 4 bedrooms, 2.5 bathrooms, with the primary bed...	4 beds \| 3 baths \| 1,913 sq.ft.	$339,000	Airbnb cash on cash: 5.91% Traditional cash on cash: 5.44% Airbnb Rental Income: $3312 Traditional Rental Income: $2421 Airbnb ROI: 5.91% Traditional ROI: 5.44%
3721 Bay Crescent Chesapeake, VA Single Family unit welcomes you into an inviting open concept living space, with beautiful...	4 beds \| 3 baths \| 1,913 sq.ft.	$360,000	Airbnb cash on cash: 5.51% Traditional cash on cash: 5.03% Airbnb Rental Income: $3312 Traditional Rental Income: $2410 Airbnb ROI: 5.51% Traditional ROI: 5.03%
1457 Leckford Drive Chesapeake, VA Beautiful and move-in ready condo in desirable Brighton Park at Greenbrier! This light-fil...	3 beds \| 3 baths \| 1,338 sq.ft.	$285,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 5.63% Airbnb Rental Income: $2762 Traditional Rental Income: $2109 Airbnb ROI: 5.64% Traditional ROI: 5.63%

Vacation Rentals in Chesapeake

There are 7 vacation rental properties available for sale in the city of Chesapeake . The median list price of Airbnb properties available for sale in Chesapeake is $446,000 and the average price per square foot is $202. The cash on cash return on vacation rentals in Chesapeake is 1.00%. The average monthly short term rental income in Chesapeake is $1,632.

Chesapeake, VA Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 7 Airbnb properties available for sale in Chesapeake.

In 2025, the best neighborhood to buy short term rental property is Greenbrier West.

In October 2025, the average Airbnb occupancy rate in Chesapeake is 32%.

In 2025, the highest Airbnb occupancy rate in Chesapeake are in Greenbrier West (35%), Indian River (36%) and Indian River (31%).

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

Your search for investment property begins and ends here

Airbnb For Sale in Chesapeake, VA

1408 Ashton Street

Chesapeake, VA

4 beds | 3 baths | 1,900 sq.ft.

$369,000

Airbnb cash on cash: 5.3%

Traditional cash on cash: 5.21%

Airbnb Rental Income: $3312

Traditional Rental Income: $2539

Airbnb ROI: 5.3%

Traditional ROI: 5.21%

4019 Sea Cliff Road

Chesapeake, VA

4 beds | 2 baths | 1,751 sq.ft.

$350,000

Airbnb cash on cash: 5.73%

Traditional cash on cash: 4.74%

Airbnb Rental Income: $3312

Traditional Rental Income: $2246

Airbnb ROI: 5.73%

Traditional ROI: 4.74%

1409 Debbs Lane

Chesapeake, VA

3 beds | 2 baths | 1,500 sq.ft.

$367,500

Airbnb cash on cash: 3.91%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $2762

Traditional Rental Income: $2065

Airbnb ROI: 3.91%

Traditional ROI: 3.77%

2115 Rocky Point Run #A

Chesapeake, VA

2 beds | 1 baths | 822 sq.ft.

$196,500

Airbnb cash on cash: 5.45%

Traditional cash on cash: 5.18%

Airbnb Rental Income: $2005

Traditional Rental Income: $1431

Airbnb ROI: 5.45%

Traditional ROI: 5.18%

4044 River Breeze Circle

Chesapeake, VA

4 beds | 3 baths | 1,913 sq.ft.

$339,000

Airbnb cash on cash: 5.91%

Traditional cash on cash: 5.44%

Airbnb Rental Income: $3312

Traditional Rental Income: $2421

Airbnb ROI: 5.91%

Traditional ROI: 5.44%

3721 Bay Crescent

Chesapeake, VA

4 beds | 3 baths | 1,913 sq.ft.

$360,000

Airbnb cash on cash: 5.51%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $3312

Traditional Rental Income: $2410

Airbnb ROI: 5.51%

Traditional ROI: 5.03%

1457 Leckford Drive

Chesapeake, VA

3 beds | 3 baths | 1,338 sq.ft.

$285,000

Airbnb cash on cash: 5.64%

Traditional cash on cash: 5.63%

Airbnb Rental Income: $2762

Traditional Rental Income: $2109

Airbnb ROI: 5.64%

Traditional ROI: 5.63%

Vacation Rentals in Chesapeake

Chesapeake, VA Short Term Rentals FAQs for Buyers, Sellers and Investors

How many Airbnb properties are available for sale in Chesapeake?

Which neighborhoods in Chesapeake to invest in 2025 for short term rentals?

What is the average Airbnb occupancy rate in Chesapeake, VA?

Where is the highest occupancy rate for Airbnb in Chesapeake, VA?

How to get Chesapeake, VA Airbnb data?

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