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
4207 Coffman Boulevard Chesapeake, VA Well-maintained home, on over half an acre lot in desirable Chadswyck Terrace. Inviting la...	4 beds \| 2 baths \| 1,468 sq.ft.	$394,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 3.74% Airbnb Rental Income: $3776 Traditional Rental Income: $2193 Airbnb ROI: 5.81% Traditional ROI: 3.74%
858 Waters Road Chesapeake, VA Over $42,420 in Renovations! Beautiful Ranch with screened porch, detached garage, and cir...	4 beds \| 2 baths \| 1,736 sq.ft.	$525,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 2.74% Airbnb Rental Income: $3336 Traditional Rental Income: $2321 Airbnb ROI: 3.29% Traditional ROI: 2.74%
4126 Scotfield Drive Chesapeake, VA In a quiet cul-de-sac, this brick-front home features high ceilings in the entryway, a for...	4 beds \| 3 baths \| 2,136 sq.ft.	$469,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 3.92% Airbnb Rental Income: $3776 Traditional Rental Income: $2660 Airbnb ROI: 4.6% Traditional ROI: 3.92%
1308 Sunnybrook Terrace Chesapeake, VA Welcome to 1308 Sunnybrook Terrace! This well-maintained 4-bedroom, 3-full-bath home offer...	4 beds \| 3 baths \| 2,200 sq.ft.	$350,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 6.21% Airbnb Rental Income: $3776 Traditional Rental Income: $2850 Airbnb ROI: 6.54% Traditional ROI: 6.21%
4100 Scotfield Drive Chesapeake, VA A Beautiful Brick Home nestled in the sought after Scotfield Woods community of Western Br...	4 beds \| 3 baths \| 2,452 sq.ft.	$599,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.1% Airbnb Rental Income: $3776 Traditional Rental Income: $2830 Airbnb ROI: 3.33% Traditional ROI: 3.1%
3944 Port Road Chesapeake, VA This lovely 3 bedroom/1 bath abode is fresh, charming and a perfect fit for the whole fami...	3 beds \| 1 baths \| 1,275 sq.ft.	$315,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 3.58% Airbnb Rental Income: $2290 Traditional Rental Income: $1710 Airbnb ROI: 3.62% Traditional ROI: 3.58%
539 Schaefer Avenue Chesapeake, VA Built in 2017 and thoughtfully maintained, this spacious 4-bedroom, 2.5-bath Chesapeake ho...	4 beds \| 3 baths \| 2,225 sq.ft.	$489,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 3.55% Airbnb Rental Income: $3776 Traditional Rental Income: $2615 Airbnb ROI: 4.3% Traditional ROI: 3.55%
723 Aguila Drive Chesapeake, VA Beautifully updated four bed, two and a half bath home located in the heart of Las Gaviota...	4 beds \| 3 baths \| 2,600 sq.ft.	$600,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 2.49% Airbnb Rental Income: $3336 Traditional Rental Income: $2539 Airbnb ROI: 2.58% Traditional ROI: 2.49%
813 Mullen Road Chesapeake, VA New Construction in Great Bridge high school district, near interstates, dining, shopping....	4 beds \| 3 baths \| 1,800 sq.ft.	$439,900	Airbnb cash on cash: 2.77% Traditional cash on cash: 1.78% Airbnb Rental Income: $2716 Traditional Rental Income: $1667 Airbnb ROI: 2.77% Traditional ROI: 1.78%
2121 Speedy Avenue Chesapeake, VA Dazzling one story home Nestled in the back of the neighborhood on a no outlet road with e...	4 beds \| 3 baths \| 1,543 sq.ft.	$390,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 4.06% Airbnb Rental Income: $2999 Traditional Rental Income: $2219 Airbnb ROI: 4.31% Traditional ROI: 4.06%
3931 Port Road Chesapeake, VA 4 bedroom ranch offering an open layout. This home features a converted garage that provid...	4 beds \| 2 baths \| 1,275 sq.ft.	$254,500	Airbnb cash on cash: 9.85% Traditional cash on cash: 6.33% Airbnb Rental Income: $3776 Traditional Rental Income: $2112 Airbnb ROI: 9.85% Traditional ROI: 6.33%
5001 Clifton Street Chesapeake, VA Rare package deal opportunity in highly sought-after Western Branch! This move-in ready 3-...	3 beds \| 1 baths \| 960 sq.ft.	$200,000	Airbnb cash on cash: 6.49% Traditional cash on cash: 6% Airbnb Rental Income: $2279 Traditional Rental Income: $1618 Airbnb ROI: 6.49% Traditional ROI: 6%
2024 Lisbon Road Chesapeake, VA SELLER WILL PAY 2% TOWARD BUYER'S CLOSING COSTS OR RATE BUY DOWN WITH ACCEPTABLE OFFER! En...	4 beds \| 3 baths \| 1,924 sq.ft.	$404,900	Airbnb cash on cash: 5.72% Traditional cash on cash: 3.16% Airbnb Rental Income: $3776 Traditional Rental Income: $1985 Airbnb ROI: 5.72% Traditional ROI: 3.16%
732 Washington Drive Chesapeake, VA Gorgeous open floor custom built ranch w/twelve ft ceilings in family & dining room, nine ...	4 beds \| 2 baths \| 2,863 sq.ft.	$639,900	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.92% Airbnb Rental Income: $3336 Traditional Rental Income: $2378 Airbnb ROI: 2.27% Traditional ROI: 1.92%
1530 Jolliff Road Chesapeake, VA Ready Soon! Your New Home in Western Branch! Exceptional new construction on a spacious ha...	4 beds \| 3 baths \| 2,320 sq.ft.	$599,900	Airbnb cash on cash: 3.12% Traditional cash on cash: 2.95% Airbnb Rental Income: $3776 Traditional Rental Income: $2860 Airbnb ROI: 3.12% Traditional ROI: 2.95%
303 Diamond Avenue Chesapeake, VA Welcome to your new home!Offering peace of mind and modern comfort, this home features a b...	3 beds \| 2 baths \| 1,500 sq.ft.	$325,000	Airbnb cash on cash: 3.01% Traditional cash on cash: 2.93% Airbnb Rental Income: $2063 Traditional Rental Income: $1505 Airbnb ROI: 3.01% Traditional ROI: 2.93%
843 Quail Avenue Chesapeake, VA **Excellent investment opportunity! This tenant-occupied home is situated on a quiet stree...	4 beds \| 1 baths \| 905 sq.ft.	$199,000	Airbnb cash on cash: 9.95% Traditional cash on cash: 5.96% Airbnb Rental Income: $2999 Traditional Rental Income: $1555 Airbnb ROI: 9.95% Traditional ROI: 5.96%
744 Partridge Avenue Chesapeake, VA **Excellent investment opportunity! This tenant-occupied home is situated on a quiet stree...	4 beds \| 1 baths \| 1,166 sq.ft.	$199,000	Airbnb cash on cash: 9.84% Traditional cash on cash: 6.35% Airbnb Rental Income: $2999 Traditional Rental Income: $1652 Airbnb ROI: 9.84% Traditional ROI: 6.35%
404 Redbrick Drive Chesapeake, VA Beautifully renovated 4-bedroom, 3 bath home in Chesapeake featuring two primary suites, i...	4 beds \| 3 baths \| 2,010 sq.ft.	$449,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 3.46% Airbnb Rental Income: $2999 Traditional Rental Income: $2267 Airbnb ROI: 3.56% Traditional ROI: 3.46%
716 Hillwell Road #B Chesapeake, VA You know that feeling when a house just makes sense? This one has it. Three bedrooms, two ...	3 beds \| 2 baths \| 1,356 sq.ft.	$359,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 3.5% Airbnb Rental Income: $2544 Traditional Rental Income: $1841 Airbnb ROI: 3.76% Traditional ROI: 3.5%
1949 Paw Paw Place Chesapeake, VA The Marigold is a thoughtfully designed rear-load home that blends convenience, elegance, ...	4 beds \| 3 baths \| 2,703 sq.ft.	$649,900	Airbnb cash on cash: 2.75% Traditional cash on cash: 2.43% Airbnb Rental Income: $3776 Traditional Rental Income: $2764 Airbnb ROI: 2.75% Traditional ROI: 2.43%
1956 Paw Paw Place Chesapeake, VA The Marigold is a thoughtfully designed rear-load home that blends convenience, elegance, ...	4 beds \| 3 baths \| 2,703 sq.ft.	$663,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 2.33% Airbnb Rental Income: $3776 Traditional Rental Income: $2764 Airbnb ROI: 2.65% Traditional ROI: 2.33%
1952 Paw Paw Place Chesapeake, VA Welcome to our Olive model! Featuring an open floor plan, gourmet kitchen, tile backsplash...	4 beds \| 3 baths \| 2,232 sq.ft.	$594,900	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.57% Airbnb Rental Income: $3776 Traditional Rental Income: $2626 Airbnb ROI: 3.17% Traditional ROI: 2.57%
1944 Paw Paw Place Chesapeake, VA The Marigold is a thoughtfully designed rear-load home that blends convenience, elegance, ...	4 beds \| 3 baths \| 2,703 sq.ft.	$654,900	Airbnb cash on cash: 2.7% Traditional cash on cash: 2.39% Airbnb Rental Income: $3776 Traditional Rental Income: $2764 Airbnb ROI: 2.7% Traditional ROI: 2.39%
1953 Paw Paw Place Chesapeake, VA Welcome to our Olive model! Featuring an open floor plan, gourmet kitchen, tile backsplash...	4 beds \| 3 baths \| 2,232 sq.ft.	$594,900	Airbnb cash on cash: 3.16% Traditional cash on cash: 2.56% Airbnb Rental Income: $3776 Traditional Rental Income: $2626 Airbnb ROI: 3.16% Traditional ROI: 2.56%
4733 Sondej Avenue Chesapeake, VA Project property. Sold as is. 3 Bedroom 1 bathroom, 1 living area, kitchen and small laund...	3 beds \| 1 baths \| 988 sq.ft.	$330,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 2.3% Airbnb Rental Income: $2290 Traditional Rental Income: $1664 Airbnb ROI: 2.47% Traditional ROI: 2.3%
1529 Lauren Ashleigh Drive Chesapeake, VA Seller is offering a contribution toward a 2-1 interest rate buydown! Subject to lender ap...	4 beds \| 3 baths \| 3,629 sq.ft.	$670,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 2.42% Airbnb Rental Income: $3776 Traditional Rental Income: $2781 Airbnb ROI: 2.7% Traditional ROI: 2.42%
1505 Sparrow Rd Chesapeake, VA Corner lot 3-4 bedroom home on .25 acres featuring a horseshoe driveway plus a paved drive...	4 beds \| 1 baths \| 1,264 sq.ft.	$327,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.06% Airbnb Rental Income: $2999 Traditional Rental Income: $1884 Airbnb ROI: 5.44% Traditional ROI: 4.06%
708 Wimbley Lane Chesapeake, VA Beautiful Cape Cod ranch on a cul-de-sac lot featuring 4 bedrooms, 2 full baths, and a 2-c...	4 beds \| 2 baths \| 2,366 sq.ft.	$537,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 2.92% Airbnb Rental Income: $3336 Traditional Rental Income: $2522 Airbnb ROI: 3.06% Traditional ROI: 2.92%
605 Wingfield Avenue Chesapeake, VA Welcome to this charming two-story Cape Cod offering 4 bedrooms and a spacious open floor ...	4 beds \| 1 baths \| 1,484 sq.ft.	$279,900	Airbnb cash on cash: 6.58% Traditional cash on cash: 4.61% Airbnb Rental Income: $2999 Traditional Rental Income: $1791 Airbnb ROI: 6.58% Traditional ROI: 4.61%
4199 Taught Line Loop Chesapeake, VA Opportunity awaits in Chesapeake at Goose Creek! This spacious 4-bedroom, 2.5-bath detache...	4 beds \| 3 baths \| 2,160 sq.ft.	$299,900	Airbnb cash on cash: 7.94% Traditional cash on cash: 6.51% Airbnb Rental Income: $3776 Traditional Rental Income: $2554 Airbnb ROI: 7.94% Traditional ROI: 6.51%
1885 Paw Paw Place Chesapeake, VA The Persimmon is a stunning two story floor plan featuring a first floor bedroom and optio...	4 beds \| 3 baths \| 2,619 sq.ft.	$611,214	Airbnb cash on cash: 3.02% Traditional cash on cash: 2.7% Airbnb Rental Income: $3776 Traditional Rental Income: $2775 Airbnb ROI: 3.02% Traditional ROI: 2.7%
1011 Cedar Tree Court Chesapeake, VA Welcome to the popular Campbell model by Kirbor Homes, where thoughtfully designed spaces ...	4 beds \| 3 baths \| 2,632 sq.ft.	$684,824	Airbnb cash on cash: 1.58% Traditional cash on cash: 1.49% Airbnb Rental Income: $3336 Traditional Rental Income: $2539 Airbnb ROI: 1.58% Traditional ROI: 1.49%
423 Las Gaviotas Boulevard Chesapeake, VA Welcome to 423 Las Gaviotas Blvd., located in the desirable Las Gaviotas golf course commu...	4 beds \| 3 baths \| 2,585 sq.ft.	$565,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 2.78% Airbnb Rental Income: $3336 Traditional Rental Income: $2539 Airbnb ROI: 2.88% Traditional ROI: 2.78%
145 Hurdle Drive Chesapeake, VA Welcome to this spacious 4-bed, 2-bath home situated on a beautiful half-acre lot in the h...	4 beds \| 2 baths \| 1,852 sq.ft.	$459,900	Airbnb cash on cash: 4.56% Traditional cash on cash: 4.12% Airbnb Rental Income: $3336 Traditional Rental Income: $2399 Airbnb ROI: 4.56% Traditional ROI: 4.12%
4748 Barn Swallow Drive Chesapeake, VA Welcome home to this beautifully updated property located in the Jolliff Woods neighborhoo...	4 beds \| 3 baths \| 2,837 sq.ft.	$565,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 3.44% Airbnb Rental Income: $3776 Traditional Rental Income: $2892 Airbnb ROI: 3.56% Traditional ROI: 3.44%
116 Ash Hill Landing Chesapeake, VA This 4-bedroom, 2.5-bath home offers 2,326 sq ft on a 0.29-acre corner lot at the end of a...	4 beds \| 3 baths \| 2,326 sq.ft.	$525,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 3.03% Airbnb Rental Income: $3336 Traditional Rental Income: $2539 Airbnb ROI: 3.14% Traditional ROI: 3.03%
709 Aguila Drive Chesapeake, VA Stunning 4-bedroom home in the highly coveted Las Gaviotas community, overlooking the golf...	4 beds \| 3 baths \| 2,600 sq.ft.	$599,900	Airbnb cash on cash: 2.6% Traditional cash on cash: 2.51% Airbnb Rental Income: $3336 Traditional Rental Income: $2539 Airbnb ROI: 2.6% Traditional ROI: 2.51%
4025 Ahoy Drive Chesapeake, VA Stunning NEW CONSTRUCTION home with downstairs bedroom/Office w/bath. Primary bedroom plus...	4 beds \| 3 baths \| 2,180 sq.ft.	$449,900	Airbnb cash on cash: 5.49% Traditional cash on cash: 5.2% Airbnb Rental Income: $3776 Traditional Rental Income: $2837 Airbnb ROI: 5.49% Traditional ROI: 5.2%
2428 Armor Lane Chesapeake, VA Well cared for brick ranch style home in the heart of Georgetown. This home shows pride of...	4 beds \| 2 baths \| 1,614 sq.ft.	$399,900	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.98% Airbnb Rental Income: $2999 Traditional Rental Income: $2252 Airbnb ROI: 4.13% Traditional ROI: 3.98%

Vacation Rentals in Chesapeake

There are 41 vacation rental properties available for sale in the city of Chesapeake . The median list price of Airbnb properties available for sale in Chesapeake is $417,547 and the average price per square foot is $198. The cash on cash return on vacation rentals in Chesapeake is 2.00%. The average monthly short term rental income in Chesapeake is $2,210.

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

There are 41 Airbnb properties available for sale in Chesapeake.

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

In November 2026, the average Airbnb occupancy rate in Chesapeake is 35%.

In 2026, the highest Airbnb occupancy rate in Chesapeake are in Indian River (38%), Greenbrier West (33%) and Greenbrier West (34%).

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

4207 Coffman Boulevard

Chesapeake, VA

4 beds | 2 baths | 1,468 sq.ft.

$394,000

Airbnb cash on cash: 5.81%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $3776

Traditional Rental Income: $2193

Airbnb ROI: 5.81%

Traditional ROI: 3.74%

858 Waters Road

Chesapeake, VA

4 beds | 2 baths | 1,736 sq.ft.

$525,000

Airbnb cash on cash: 3.29%

Traditional cash on cash: 2.74%

Airbnb Rental Income: $3336

Traditional Rental Income: $2321

Airbnb ROI: 3.29%

Traditional ROI: 2.74%

4126 Scotfield Drive

Chesapeake, VA

4 beds | 3 baths | 2,136 sq.ft.

$469,000

Airbnb cash on cash: 4.6%

Traditional cash on cash: 3.92%

Airbnb Rental Income: $3776

Traditional Rental Income: $2660

Airbnb ROI: 4.6%

Traditional ROI: 3.92%

1308 Sunnybrook Terrace

Chesapeake, VA

4 beds | 3 baths | 2,200 sq.ft.

$350,000

Airbnb cash on cash: 6.54%

Traditional cash on cash: 6.21%

Airbnb Rental Income: $3776

Traditional Rental Income: $2850

Airbnb ROI: 6.54%

Traditional ROI: 6.21%

4100 Scotfield Drive

Chesapeake, VA

4 beds | 3 baths | 2,452 sq.ft.

$599,000

Airbnb cash on cash: 3.33%

Traditional cash on cash: 3.1%

Airbnb Rental Income: $3776

Traditional Rental Income: $2830

Airbnb ROI: 3.33%

Traditional ROI: 3.1%

3944 Port Road

Chesapeake, VA

3 beds | 1 baths | 1,275 sq.ft.

$315,000

Airbnb cash on cash: 3.62%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $2290

Traditional Rental Income: $1710

Airbnb ROI: 3.62%

Traditional ROI: 3.58%

539 Schaefer Avenue

Chesapeake, VA

4 beds | 3 baths | 2,225 sq.ft.

$489,000

Airbnb cash on cash: 4.3%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $3776

Traditional Rental Income: $2615

Airbnb ROI: 4.3%

Traditional ROI: 3.55%

723 Aguila Drive

Chesapeake, VA

4 beds | 3 baths | 2,600 sq.ft.

$600,000

Airbnb cash on cash: 2.58%

Traditional cash on cash: 2.49%

Airbnb Rental Income: $3336

Traditional Rental Income: $2539

Airbnb ROI: 2.58%