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
1310 Virginia Avenue Chesapeake, VA Come visit this awesome, newly renovated home in Ardmore! The spacious living room opens u...	4 beds \| 3 baths \| 1,750 sq.ft.	$359,900	Airbnb cash on cash: 7.26% Traditional cash on cash: 3.96% Airbnb Rental Income: $3999 Traditional Rental Income: $2028 Airbnb ROI: 7.26% Traditional ROI: 3.96%
4176 Williamson Street Chesapeake, VA Charming and cozy, this small bungalow offers the perfect blend of modern updates and conv...	3 beds \| 2 baths \| 1,404 sq.ft.	$258,900	Airbnb cash on cash: 8.82% Traditional cash on cash: 6.83% Airbnb Rental Income: $3346 Traditional Rental Income: $2112 Airbnb ROI: 8.82% Traditional ROI: 6.83%
4631 Captain Carter Circle Chesapeake, VA Welcome to this beautiful, 2-story home featuring 4-bedrooms, 2.5-bathrooms. As you approa...	4 beds \| 3 baths \| 2,250 sq.ft.	$445,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 5.32% Airbnb Rental Income: $4041 Traditional Rental Income: $3130 Airbnb ROI: 5.44% Traditional ROI: 5.32%
2904 Kilbride Drive Chesapeake, VA Investors Opportunity! This 3- bedroom 1 bathroom bungalow is fantastic addition to any po...	3 beds \| 1 baths \| 950 sq.ft.	$220,000	Airbnb cash on cash: 9.81% Traditional cash on cash: 5% Airbnb Rental Income: $3268 Traditional Rental Income: $1534 Airbnb ROI: 9.81% Traditional ROI: 5%
1519 Scoonie Pointe Drive #116 Chesapeake, VA Eagle Point is a gated community for 55 and over at Cahoon Plantation: It features a 1ST F...	3 beds \| 3 baths \| 1,870 sq.ft.	$375,000	Airbnb cash on cash: 7.7% Traditional cash on cash: 4% Airbnb Rental Income: $4428 Traditional Rental Income: $2200 Airbnb ROI: 7.7% Traditional ROI: 4%
4117 Pinta Drive Chesapeake, VA Wow! This gorgeous 4-bedroom home in desirable Western Branch feels like new! Brand new HV...	4 beds \| 2 baths \| 1,848 sq.ft.	$399,900	Airbnb cash on cash: 6.45% Traditional cash on cash: 4.42% Airbnb Rental Income: $4041 Traditional Rental Income: $2418 Airbnb ROI: 6.45% Traditional ROI: 4.42%
2344 Paramont Avenue Chesapeake, VA This is the one you have been waiting for! Well cared for home with tons of charm. Nicely ...	3 beds \| 2 baths \| 1,641 sq.ft.	$325,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 4.46% Airbnb Rental Income: $3268 Traditional Rental Income: $2024 Airbnb ROI: 6.13% Traditional ROI: 4.46%
3005 Barn Way Chesapeake, VA This stunning ranch has been tastefully updated with new paint, updated lighting, and new ...	4 beds \| 3 baths \| 1,500 sq.ft.	$374,900	Airbnb cash on cash: 5.36% Traditional cash on cash: 4.36% Airbnb Rental Income: $3341 Traditional Rental Income: $2243 Airbnb ROI: 5.36% Traditional ROI: 4.36%
2805 Princeton Avenue Chesapeake, VA Welcome to 2805 Princeton Ave. in beautiful Chesapeake, VA! This charming 2-bedroom, home ...	2 beds \| 1 baths \| 1,040 sq.ft.	$244,900	Airbnb cash on cash: 8.28% Traditional cash on cash: 5.38% Airbnb Rental Income: $3130 Traditional Rental Income: $1749 Airbnb ROI: 8.28% Traditional ROI: 5.38%
3000 Stratford Drive Chesapeake, VA Look no further for your oasis.. This place is ready to be called HOME in the sought-after...	4 beds \| 3 baths \| 2,631 sq.ft.	$520,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 3.83% Airbnb Rental Income: $3885 Traditional Rental Income: $2799 Airbnb ROI: 4.34% Traditional ROI: 3.83%
1530 Jackson Avenue Chesapeake, VA Discover an updated 1922 classic home featuring 3 bedrooms and 2.5 baths across 1,820 sq f...	3 beds \| 3 baths \| 1,820 sq.ft.	$275,000	Airbnb cash on cash: 7.92% Traditional cash on cash: 7.36% Airbnb Rental Income: $3346 Traditional Rental Income: $2455 Airbnb ROI: 7.92% Traditional ROI: 7.36%
1327 HAZEL AVE Chesapeake, VA Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,176 sq.ft.	$291,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 4.8% Airbnb Rental Income: $3268 Traditional Rental Income: $1866 Airbnb ROI: 7.24% Traditional ROI: 4.8%
2 Harbor Watch Drive #702 Chesapeake, VA A completely renovated 3-bedroom, 2-bath first-floor condo, just under 1,800 sqft, located...	3 beds \| 2 baths \| 1,740 sq.ft.	$299,000	Airbnb cash on cash: 7.33% Traditional cash on cash: 5.57% Airbnb Rental Income: $3471 Traditional Rental Income: $2208 Airbnb ROI: 7.33% Traditional ROI: 5.57%
100 Foster Court Chesapeake, VA Experience carefree living in this stunning 3 BR 2 BA single-family detached condo. This l...	3 beds \| 2 baths \| 1,450 sq.ft.	$299,900	Airbnb cash on cash: 6.75% Traditional cash on cash: 4.94% Airbnb Rental Income: $3268 Traditional Rental Income: $2022 Airbnb ROI: 6.75% Traditional ROI: 4.94%
3004 Sunrise Avenue Chesapeake, VA Investment opportunity. Most likely will require cash or 203k loan. Also potential VA loan...	3 beds \| 2 baths \| 1,400 sq.ft.	$250,000	Airbnb cash on cash: 8.33% Traditional cash on cash: 6.34% Airbnb Rental Income: $3268 Traditional Rental Income: $2063 Airbnb ROI: 8.33% Traditional ROI: 6.34%
1316 18th Street Chesapeake, VA Better than renting... this 3 bedroom home with a yard is great for a busy lifestyle.Â Fr...	3 beds \| 3 baths \| 1,384 sq.ft.	$269,000	Airbnb cash on cash: 8.03% Traditional cash on cash: 6.06% Airbnb Rental Income: $3346 Traditional Rental Income: $2099 Airbnb ROI: 8.03% Traditional ROI: 6.06%
1308 Seaboard Avenue Chesapeake, VA Stop by and tour this home nestled in Chesapeake, Virginia. The primary bedroom is located...	4 beds \| 3 baths \| 2,002 sq.ft.	$383,000	Airbnb cash on cash: 6.79% Traditional cash on cash: 5.38% Airbnb Rental Income: $3999 Traditional Rental Income: $2638 Airbnb ROI: 6.79% Traditional ROI: 5.38%
306 Cotton Mill Court Chesapeake, VA Move-in ready! Come see this gorgeously updated 4 bed/2 bath ranch & make it âhome!â T...	4 beds \| 2 baths \| 1,600 sq.ft.	$365,000	Airbnb cash on cash: 5.45% Traditional cash on cash: 5.08% Airbnb Rental Income: $3341 Traditional Rental Income: $2470 Airbnb ROI: 5.45% Traditional ROI: 5.08%
731 OSBORN Avenue Chesapeake, VA Come see this adorable, unique and charming 3 bedroom, 2 bath home centrally located in Ch...	3 beds \| 2 baths \| 1,300 sq.ft.	$265,000	Airbnb cash on cash: 7.87% Traditional cash on cash: 6.03% Airbnb Rental Income: $3268 Traditional Rental Income: $2076 Airbnb ROI: 7.87% Traditional ROI: 6.03%
1512 Chesapeake Avenue Chesapeake, VA This charming Chesapeake neighborhood offers convenient access to military bases, shopping...	4 beds \| 2 baths \| 2,226 sq.ft.	$340,000	Airbnb cash on cash: 7.73% Traditional cash on cash: 5.33% Airbnb Rental Income: $3999 Traditional Rental Income: $2377 Airbnb ROI: 7.73% Traditional ROI: 5.33%
703 Stalham Road Chesapeake, VA Please bring your buyers to see this beautiful, quaint 3 bedroom, 2 bathroom ranch style p...	3 beds \| 2 baths \| 1,300 sq.ft.	$310,000	Airbnb cash on cash: 6.57% Traditional cash on cash: 5.27% Airbnb Rental Income: $3268 Traditional Rental Income: $2154 Airbnb ROI: 6.57% Traditional ROI: 5.27%
1310 Commerce Avenue Chesapeake, VA Rich LVP creates a warm, polished canvas where your fresh start awaits you! Fall in love w...	3 beds \| 3 baths \| 1,472 sq.ft.	$304,000	Airbnb cash on cash: 7.02% Traditional cash on cash: 4.14% Airbnb Rental Income: $3346 Traditional Rental Income: $1774 Airbnb ROI: 7.02% Traditional ROI: 4.14%
2613 DEERFIELD Crescent Chesapeake, VA Stunning 4-bedroom ranch in West Branch! This home features a spacious open floor plan wit...	4 beds \| 2 baths \| 2,186 sq.ft.	$430,000	Airbnb cash on cash: 5.51% Traditional cash on cash: 4.21% Airbnb Rental Income: $3885 Traditional Rental Income: $2525 Airbnb ROI: 5.51% Traditional ROI: 4.21%
1312 22nd Street Chesapeake, VA WELCOME HOME! This charming home in the heart of South Norfolk is waiting for you. Fresh p...	3 beds \| 2 baths \| 1,290 sq.ft.	$230,000	Airbnb cash on cash: 9.89% Traditional cash on cash: 7.01% Airbnb Rental Income: $3346 Traditional Rental Income: $1972 Airbnb ROI: 9.89% Traditional ROI: 7.01%
757 Sherman Drive Chesapeake, VA Discover this updated and inviting 3-bedroom, 2-bath ranch home. Featuring an open main li...	3 beds \| 2 baths \| 1,570 sq.ft.	$315,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 4.77% Airbnb Rental Income: $3471 Traditional Rental Income: $2055 Airbnb ROI: 6.96% Traditional ROI: 4.77%
508 Stalham Road Chesapeake, VA Great ranch home in the heart of Chesapeake. Quaint living room open to the kitchen with b...	3 beds \| 1 baths \| 950 sq.ft.	$242,000	Airbnb cash on cash: 8.9% Traditional cash on cash: 4.79% Airbnb Rental Income: $3268 Traditional Rental Income: $1596 Airbnb ROI: 8.9% Traditional ROI: 4.79%
1405 Perry Street Chesapeake, VA Just bring your things and move-in! Home has 3 bedrooms, 2 baths with an open concept livi...	3 beds \| 2 baths \| 1,188 sq.ft.	$269,000	Airbnb cash on cash: 8.17% Traditional cash on cash: 5.48% Airbnb Rental Income: $3346 Traditional Rental Income: $1918 Airbnb ROI: 8.17% Traditional ROI: 5.48%
3309 Indigo Road Chesapeake, VA Welcome Home! This charming ranch home is nestled on a quiet street, in a beautiful neighb...	3 beds \| 2 baths \| 1,341 sq.ft.	$325,000	Airbnb cash on cash: 6.16% Traditional cash on cash: 4.57% Airbnb Rental Income: $3268 Traditional Rental Income: $2050 Airbnb ROI: 6.16% Traditional ROI: 4.57%
140 Springer Ln #234 Chesapeake, VA Gated Community! Elevator! Move In Ready! Peaceful, quiet, and serene living is what you w...	2 beds \| 3 baths \| 1,771 sq.ft.	$275,000	Airbnb cash on cash: 9.21% Traditional cash on cash: 6.47% Airbnb Rental Income: $3780 Traditional Rental Income: $2249 Airbnb ROI: 9.21% Traditional ROI: 6.47%
1113 Fenton Quay Chesapeake, VA Welcome to Greenwood at Greenbrier! This 3 bedroom, 2.5 bath residence sits on a corner lo...	3 beds \| 3 baths \| 1,881 sq.ft.	$412,500	Airbnb cash on cash: 4.73% Traditional cash on cash: 3.89% Airbnb Rental Income: $3471 Traditional Rental Income: $2376 Airbnb ROI: 4.73% Traditional ROI: 3.89%
2309 Drum Creek Road Chesapeake, VA Experience modern elegance in this beautifully renovated 3-bedroom, 2-bath brick ranch loc...	3 beds \| 2 baths \| 1,771 sq.ft.	$419,900	Airbnb cash on cash: 3.55% Traditional cash on cash: 3.5% Airbnb Rental Income: $2824 Traditional Rental Income: $2145 Airbnb ROI: 3.55% Traditional ROI: 3.5%
1001 Still Harbor Circle Chesapeake, VA This beautifully updated 3-bedroom, end-unit townhome offers modern comforts and serene wa...	3 beds \| 2 baths \| 1,216 sq.ft.	$295,000	Airbnb cash on cash: 7.51% Traditional cash on cash: 4.59% Airbnb Rental Income: $3471 Traditional Rental Income: $1894 Airbnb ROI: 7.51% Traditional ROI: 4.59%
417 Broad Bend Circle Chesapeake, VA Single Family home in the desirable Riverwalk Community. Open floor plan with primary bedr...	2 beds \| 3 baths \| 2,094 sq.ft.	$405,000	Airbnb cash on cash: 5.47% Traditional cash on cash: 4.12% Airbnb Rental Income: $3780 Traditional Rental Income: $2448 Airbnb ROI: 5.47% Traditional ROI: 4.12%
3128 Camelot Boulevard Chesapeake, VA	4 beds \| 3 baths \| 1,819 sq.ft.	$340,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 5.98% Airbnb Rental Income: $3341 Traditional Rental Income: $2576 Airbnb ROI: 6.04% Traditional ROI: 5.98%
2109 Lockard Avenue Chesapeake, VA Discover this ideal ranch located in Chesapeake, nestled in the desirable Norfolk Highland...	3 beds \| 2 baths \| 1,352 sq.ft.	$314,900	Airbnb cash on cash: 6.46% Traditional cash on cash: 4.6% Airbnb Rental Income: $3268 Traditional Rental Income: $1984 Airbnb ROI: 6.46% Traditional ROI: 4.6%
2602 Omar Street Chesapeake, VA Lifetime warrantied Pergo flooring flows throughout this bright and airy home with cozy ca...	4 beds \| 2 baths \| 1,770 sq.ft.	$312,000	Airbnb cash on cash: 8.44% Traditional cash on cash: 5.45% Airbnb Rental Income: $3999 Traditional Rental Income: $2267 Airbnb ROI: 8.44% Traditional ROI: 5.45%
2801 Estella Way Chesapeake, VA A slice of paradiseâ¦secluded and quiet. Enjoy maintenance-free living in this stunning ...	3 beds \| 3 baths \| 1,400 sq.ft.	$299,000	Airbnb cash on cash: 6.79% Traditional cash on cash: 5.09% Airbnb Rental Income: $3268 Traditional Rental Income: $2057 Airbnb ROI: 6.79% Traditional ROI: 5.09%
3910 River Breeze Circle Chesapeake, VA Discover this charming 4-bedroom, 2.5-bath detached condo located in the desirable River B...	4 beds \| 3 baths \| 1,880 sq.ft.	$335,000	Airbnb cash on cash: 7.98% Traditional cash on cash: 5.14% Airbnb Rental Income: $4041 Traditional Rental Income: $2284 Airbnb ROI: 7.98% Traditional ROI: 5.14%
812 Orville Avenue Chesapeake, VA Welcome to 812 Orville Ave, a charming and meticulously maintained home nestled in the hea...	3 beds \| 1 baths \| 1,387 sq.ft.	$285,000	Airbnb cash on cash: 7.6% Traditional cash on cash: 4.93% Airbnb Rental Income: $3346 Traditional Rental Income: $1882 Airbnb ROI: 7.6% Traditional ROI: 4.93%
3912 Starboard Road Chesapeake, VA Discover a charming 4-bedroom, 2 bathroom home nestled in the heart of Chesapeake, VA. Thi...	4 beds \| 2 baths \| 1,323 sq.ft.	$279,000	Airbnb cash on cash: 9.91% Traditional cash on cash: 6.16% Airbnb Rental Income: $4041 Traditional Rental Income: $2194 Airbnb ROI: 9.91% Traditional ROI: 6.16%

Vacation Rentals in Chesapeake

There are 152 vacation rental properties available for sale in the city of Chesapeake . The median list price of Airbnb properties available for sale in Chesapeake is $399,000 and the average price per square foot is $190. The cash on cash return on vacation rentals in Chesapeake is 6.00%. The average monthly short term rental income in Chesapeake is $3,341.

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

There are 152 Airbnb properties available for sale in Chesapeake.

In 2024, the best neighborhood to buy short term rental property is Greenbrier West.

In December 2024, the average Airbnb occupancy rate in Chesapeake is 61%.

In 2024, the highest Airbnb occupancy rate in Chesapeake are in Greenbrier West (58%), South Norfolk (53%) and South Norfolk (53%).

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

1310 Virginia Avenue

Chesapeake, VA

4 beds | 3 baths | 1,750 sq.ft.

$359,900

Airbnb cash on cash: 7.26%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $3999

Traditional Rental Income: $2028

Airbnb ROI: 7.26%

Traditional ROI: 3.96%

4176 Williamson Street

Chesapeake, VA

3 beds | 2 baths | 1,404 sq.ft.

$258,900

Airbnb cash on cash: 8.82%

Traditional cash on cash: 6.83%

Airbnb Rental Income: $3346

Traditional Rental Income: $2112

Airbnb ROI: 8.82%

Traditional ROI: 6.83%

4631 Captain Carter Circle

Chesapeake, VA

4 beds | 3 baths | 2,250 sq.ft.

$445,000

Airbnb cash on cash: 5.44%

Traditional cash on cash: 5.32%

Airbnb Rental Income: $4041

Traditional Rental Income: $3130

Airbnb ROI: 5.44%

Traditional ROI: 5.32%

2904 Kilbride Drive

Chesapeake, VA

3 beds | 1 baths | 950 sq.ft.

$220,000

Airbnb cash on cash: 9.81%

Traditional cash on cash: 5%

Airbnb Rental Income: $3268

Traditional Rental Income: $1534

Airbnb ROI: 9.81%

Traditional ROI: 5%

1519 Scoonie Pointe Drive #116

Chesapeake, VA

3 beds | 3 baths | 1,870 sq.ft.

$375,000

Airbnb cash on cash: 7.7%

Traditional cash on cash: 4%

Airbnb Rental Income: $4428

Traditional Rental Income: $2200

Airbnb ROI: 7.7%

Traditional ROI: 4%

4117 Pinta Drive

Chesapeake, VA

4 beds | 2 baths | 1,848 sq.ft.

$399,900

Airbnb cash on cash: 6.45%

Traditional cash on cash: 4.42%

Airbnb Rental Income: $4041

Traditional Rental Income: $2418

Airbnb ROI: 6.45%

Traditional ROI: 4.42%

2344 Paramont Avenue

Chesapeake, VA

3 beds | 2 baths | 1,641 sq.ft.

$325,000

Airbnb cash on cash: 6.13%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $3268

Traditional Rental Income: $2024

Airbnb ROI: 6.13%

Traditional ROI: 4.46%

3005 Barn Way

Chesapeake, VA

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

$374,900

Airbnb cash on cash: 5.36%

Traditional cash on cash: 4.36%

Airbnb Rental Income: $3341

Traditional Rental Income: $2243

Airbnb ROI: 5.36%