Real Estate Investment Properties for Sale in Chesapeake, VA

Looking for investment property in Chesapeake, VA with high ROI ?

Explore a variety of short-term homes & houses in Chesapeake, VA. Invest wisely with VRBO & Chesapeake, VA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Chesapeake, VA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1439 Thistlewood Lane Chesapeake, VA Beautifully maintained and updated Condo in the highly sought after adult active 55+ commu...	2 beds \| 2 baths \| 1,727 sq.ft.	$425,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 2.31% Airbnb Rental Income: $2309 Traditional Rental Income: $2208 Airbnb ROI: 1.12% Traditional ROI: 2.31%
4308 Colindale Road #206 Chesapeake, VA Move in ready - Beautiful 2nd floor condo. Walk into an open floor plan with new LVP in th...	2 beds \| 2 baths \| 1,367 sq.ft.	$234,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 6.81% Airbnb Rental Income: $1309 Traditional Rental Income: $2040 Airbnb ROI: 1.67% Traditional ROI: 6.81%
829 Donnington Drive Chesapeake, VA Beautiful 4-bed, 2.5 bath ranch-style home located in Ethridge Woods, a residential neighb...	4 beds \| 3 baths \| 2,651 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.98% Airbnb Rental Income: $null Traditional Rental Income: $3289 Airbnb ROI: N/A Traditional ROI: 3.98%
1016 Thoroughgood Way #307 Chesapeake, VA Make this your first stop! Beautifully maintained, low maintenance, open concept, Third fl...	2 beds \| 2 baths \| 1,255 sq.ft.	$247,500	Airbnb cash on cash: 2.33% Traditional cash on cash: 6.32% Airbnb Rental Income: $1510 Traditional Rental Income: $2004 Airbnb ROI: 2.33% Traditional ROI: 6.32%
801 Poindexter Street #314 Chesapeake, VA Spacious, move-in ready condo just minutes from Norfolk Naval Base, Portsmouth Shipyard, a...	1 beds \| 1 baths \| 1,135 sq.ft.	$183,000	Airbnb cash on cash: 2.19% Traditional cash on cash: 7.14% Airbnb Rental Income: $1185 Traditional Rental Income: $1661 Airbnb ROI: 2.19% Traditional ROI: 7.14%
828 Woodstream Way Chesapeake, VA Welcome to this beautifully maintained home in the sought-after Hickory High School distri...	4 beds \| 3 baths \| 2,785 sq.ft.	$594,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $2971 Airbnb ROI: N/A Traditional ROI: 3.29%
936A Shoal Creek Trail Chesapeake, VA Prepare to fall in love with this fantastic end unit townhome with garage! Two spacious pr...	2 beds \| 2 baths \| 1,589 sq.ft.	$299,900	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.71% Airbnb Rental Income: $1502 Traditional Rental Income: $1999 Airbnb ROI: 1.4% Traditional ROI: 4.71%
800 Monroe Court Chesapeake, VA Nestled in the heart of Greenbrier, this end-unit condo sits on a tranquil cul-de-sac with...	3 beds \| 3 baths \| 2,225 sq.ft.	$398,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 4.21% Airbnb Rental Income: $2762 Traditional Rental Income: $2385 Airbnb ROI: 3.49% Traditional ROI: 4.21%
805 Glen Oak Cove Chesapeake, VA Move in condition! Lovely, well cared for home.Updates:2025:New remodeled Bath (Tub, Vanit...	3 beds \| 2 baths \| 1,485 sq.ft.	$356,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 4.11% Airbnb Rental Income: $1632 Traditional Rental Income: $2083 Airbnb ROI: 1.38% Traditional ROI: 4.11%
5029 Pughsville Road Chesapeake, VA Easy access to all of Hampton Roads with Solar, Fenced Yard, Storage & No HOA! Welcome to ...	3 beds \| 3 baths \| 1,902 sq.ft.	$399,900	Airbnb cash on cash: 0.66% Traditional cash on cash: 4.14% Airbnb Rental Income: $1482 Traditional Rental Income: $2349 Airbnb ROI: 0.66% Traditional ROI: 4.14%
1016 Thoroughgood Way #201 Chesapeake, VA Make this your first stop! Beautifully maintained, low maintenance, open concept, second f...	2 beds \| 2 baths \| 1,169 sq.ft.	$248,900	Airbnb cash on cash: 2.31% Traditional cash on cash: 5.83% Airbnb Rental Income: $1510 Traditional Rental Income: $1898 Airbnb ROI: 2.31% Traditional ROI: 5.83%
2910 Kilbride Drive Chesapeake, VA Welcome to this renovated and well-maintained brick Ranch in Chesapeake. Many major update...	3 beds \| 1 baths \| 950 sq.ft.	$293,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 4.07% Airbnb Rental Income: $1780 Traditional Rental Income: $1697 Airbnb ROI: 2.61% Traditional ROI: 4.07%
2404 Livesay Road Chesapeake, VA Great starter home, just for you. Convenient to interstate, main roads, shopping and schoo...	4 beds \| 2 baths \| 1,145 sq.ft.	$259,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 6.68% Airbnb Rental Income: $2122 Traditional Rental Income: $2191 Airbnb ROI: 4.18% Traditional ROI: 6.68%
508 Rue Saint La Rogue Chesapeake, VA Welcome to 508 Rue Saint La Rogue, Chesapeake! Located in the desirable **Les Chateau...	2 beds \| 3 baths \| 1,158 sq.ft.	$214,990	Airbnb cash on cash: 2.77% Traditional cash on cash: 7.12% Airbnb Rental Income: $1502 Traditional Rental Income: $1950 Airbnb ROI: 2.77% Traditional ROI: 7.12%
1209 Clearwater Lane Chesapeake, VA Charming 2 story home in Etheridge Lakes. Formal Living Room and Dining Room with moldings...	4 beds \| 3 baths \| 2,226 sq.ft.	$539,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $2714 Airbnb ROI: N/A Traditional ROI: 3.3%
627 Luray Terrace Chesapeake, VA Discover storybook charm and modern luxury in this Glenwood home on a picturesque corner l...	4 beds \| 4 baths \| 1,973 sq.ft.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.24% Airbnb Rental Income: $null Traditional Rental Income: $2906 Airbnb ROI: N/A Traditional ROI: 4.24%
1209 Bingham Arch Chesapeake, VA Privacy meets convenience in this light-filled ranch bordered by wooded preserves front an...	4 beds \| 3 baths \| 2,200 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.56% Airbnb Rental Income: $null Traditional Rental Income: $2582 Airbnb ROI: N/A Traditional ROI: 2.56%
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: 2.72% Traditional cash on cash: 4.8% Airbnb Rental Income: $1780 Traditional Rental Income: $1866 Airbnb ROI: 2.72% Traditional ROI: 4.8%
1363 Cypress Place Chesapeake, VA Welcome home to Cypress Place! Nestled in the heart of Chesapeake, this home offers endles...	4 beds \| 3 baths \| 2,054 sq.ft.	$385,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 4.61% Airbnb Rental Income: $2405 Traditional Rental Income: $2480 Airbnb ROI: 2.76% Traditional ROI: 4.61%
1316 Debbs Lane Chesapeake, VA Gorgeous updated ranch in Greenbrier! Kitchen updated in 2023 with new cabinets, granite c...	3 beds \| 2 baths \| 1,431 sq.ft.	$384,900	Airbnb cash on cash: 3.71% Traditional cash on cash: 3.56% Airbnb Rental Income: $2762 Traditional Rental Income: $2059 Airbnb ROI: 3.71% Traditional ROI: 3.56%
415 Triton Trace Chesapeake, VA Closing cost assistance available andÂ seller is offering a 1-year home warranty V...	4 beds \| 3 baths \| 1,845 sq.ft.	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.15% Airbnb Rental Income: $null Traditional Rental Income: $2508 Airbnb ROI: N/A Traditional ROI: 4.15%
3424 Brandywine Drive Chesapeake, VA Don't miss this beautiful 4-bedroom, 2-bath home in Western Branch school district. Renova...	4 beds \| 2 baths \| 1,276 sq.ft.	$324,900	Airbnb cash on cash: 2.24% Traditional cash on cash: 4.61% Airbnb Rental Income: $1837 Traditional Rental Income: $2067 Airbnb ROI: 2.24% Traditional ROI: 4.61%
3408 Albury Court Chesapeake, VA Welcome to this spacious 4-bedroom, 2.5 bath beauty in a prime Chesapeake location! With o...	4 beds \| 3 baths \| 3,000 sq.ft.	$529,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.68% Airbnb Rental Income: $1837 Traditional Rental Income: $2848 Airbnb ROI: 0.64% Traditional ROI: 3.68%
300 Grain Way Chesapeake, VA Escape to your own slice of tranquility in this beautifully maintained 4-bedroom home, ne...	4 beds \| 2 baths \| 1,800 sq.ft.	$427,500	Airbnb cash on cash: 1.89% Traditional cash on cash: 4.68% Airbnb Rental Income: $2122 Traditional Rental Income: $2700 Airbnb ROI: 1.89% Traditional ROI: 4.68%
1421 Chesapeake Avenue Chesapeake, VA Perfect blend of timeless character and modern updates with this beautiful historic home. ...	3 beds \| 3 baths \| 2,070 sq.ft.	$348,500	Airbnb cash on cash: 0.73% Traditional cash on cash: 4.79% Airbnb Rental Income: $1355 Traditional Rental Income: $2267 Airbnb ROI: 0.73% Traditional ROI: 4.79%
567 Waters Road Chesapeake, VA Welcome to 567 Waters Road in Chesapeake, VA, where comfort, space, and modern living come...	4 beds \| 3 baths \| 2,100 sq.ft.	$550,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.11% Airbnb Rental Income: $1811 Traditional Rental Income: $2655 Airbnb ROI: 0.51% Traditional ROI: 3.11%
1113 Edinburgh Parkway Chesapeake, VA Welcome Home! Charming and move-in ready, this elegant home offers modern comfort with tim...	4 beds \| 3 baths \| 2,416 sq.ft.	$639,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.7% Airbnb Rental Income: $null Traditional Rental Income: $2869 Airbnb ROI: N/A Traditional ROI: 2.7%
3236 Bruin Drive Chesapeake, VA Location, location, location! Nestled on a quiet street in Western Branch, this home gives...	4 beds \| 2 baths \| 2,010 sq.ft.	$460,000	Airbnb cash on cash: 1% Traditional cash on cash: 4.26% Airbnb Rental Income: $1837 Traditional Rental Income: $2745 Airbnb ROI: 1% Traditional ROI: 4.26%
4309 Hillingdon Bend #303 Chesapeake, VA Welcome to Unit 303 at Kings Pointe, a perfect blend of comfort and convenience! Located j...	2 beds \| 2 baths \| 1,367 sq.ft.	$229,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 6.39% Airbnb Rental Income: $1309 Traditional Rental Income: $1899 Airbnb ROI: 1.79% Traditional ROI: 6.39%
1201 Country Road Chesapeake, VA Welcome to this inviting 3-bedroom, 2.5-bath home offering modern comfort and style with 9...	3 beds \| 3 baths \| 1,568 sq.ft.	$322,500	Airbnb cash on cash: 0.94% Traditional cash on cash: 4.22% Airbnb Rental Income: $1355 Traditional Rental Income: $1935 Airbnb ROI: 0.94% Traditional ROI: 4.22%
1016 Thoroughgood Way #101 Chesapeake, VA	2 beds \| 2 baths \| 1,166 sq.ft.	$230,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 6.19% Airbnb Rental Income: $1510 Traditional Rental Income: $1856 Airbnb ROI: 2.57% Traditional ROI: 6.19%
745 Lacy Oak Drive Chesapeake, VA Beautifully updated condo in excellent condition, offering modern upgrades and a thoughtfu...	2 beds \| 3 baths \| 1,870 sq.ft.	$328,999	Airbnb cash on cash: 1.21% Traditional cash on cash: 5.27% Airbnb Rental Income: $1502 Traditional Rental Income: $2317 Airbnb ROI: 1.21% Traditional ROI: 5.27%
553 Waters Road Chesapeake, VA Welcome Home! This Chesapeake gem sits on a spacious corner lot with 4 large bedrooms and ...	4 beds \| 3 baths \| 2,387 sq.ft.	$550,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.41% Airbnb Rental Income: $1811 Traditional Rental Income: $2807 Airbnb ROI: 0.51% Traditional ROI: 3.41%
1423 Otterbourne Circle Chesapeake, VA Beautifully maintained condo in the heart of Greenbrier! Thoughtfully updated throughout, ...	3 beds \| 3 baths \| 1,881 sq.ft.	$398,000	Airbnb cash on cash: 3.54% Traditional cash on cash: 5.01% Airbnb Rental Income: $2762 Traditional Rental Income: $2662 Airbnb ROI: 3.54% Traditional ROI: 5.01%
709 Phalarope Street Chesapeake, VA Welcome to this beautiful home in sought-after Culpepper Landing! Featuring elegant Torino...	4 beds \| 3 baths \| 3,662 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.87% Airbnb Rental Income: $null Traditional Rental Income: $2872 Airbnb ROI: N/A Traditional ROI: 2.87%
3549 Clover Meadows Drive Chesapeake, VA Super cute and move-in ready! This updated 2 bedrooms, 2 bath first-floor condo in Western...	2 beds \| 2 baths \| 960 sq.ft.	$169,000	Airbnb cash on cash: 3.31% Traditional cash on cash: 8.2% Airbnb Rental Income: $1309 Traditional Rental Income: $1689 Airbnb ROI: 3.31% Traditional ROI: 8.2%
933 Saddleback Trail Road Chesapeake, VA Welcome to this stellar 4-bedroom, 2-bath ranch in the heart of Chesapeake, offering 1,830...	4 beds \| 2 baths \| 1,830 sq.ft.	$495,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 4.16% Airbnb Rental Income: $1811 Traditional Rental Income: $2850 Airbnb ROI: 0.85% Traditional ROI: 4.16%
4195 Taughtline Loop Chesapeake, VA Welcome to this beautiful 3-bedroom, 2.5-bath condo in Goose Creek Estates, located in the...	3 beds \| 3 baths \| 2,062 sq.ft.	$364,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 4.51% Airbnb Rental Income: $1536 Traditional Rental Income: $2517 Airbnb ROI: 0.34% Traditional ROI: 4.51%
632 Sweet Leaf Place Chesapeake, VA Fabulous remodeled "Gourmet Chef's" kitchen. Granite/Designer Glass back splash/ Beautiful...	3 beds \| 3 baths \| 2,352 sq.ft.	$439,900	Airbnb cash on cash: 0.3% Traditional cash on cash: 4.16% Airbnb Rental Income: $1398 Traditional Rental Income: $2565 Airbnb ROI: 0.3% Traditional ROI: 4.16%
903 Lee Shore Court Chesapeake, VA The desirable Estates of Greenbrier sell quickly so don't miss out on buying this beautifu...	3 beds \| 3 baths \| 2,184 sq.ft.	$519,999	Airbnb cash on cash: -0.05% Traditional cash on cash: 3.1% Airbnb Rental Income: $1398 Traditional Rental Income: $2506 Airbnb ROI: -0.05% Traditional ROI: 3.1%

Real Estate investment in Chesapeake, VA

There are 517 properties for sale in the city of Chesapeake . The median list price in Chesapeake is $450,000 and the average price per square foot is $205. In November 2025, the average monthly cash on cash return in Chesapeake is 4.00%. The average monthly rental income in Chesapeake is $2,576.

Chesapeake, VA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 517 investment properties available for sale in Chesapeake.

In 2025, the best neighborhood to buy investment property is Greenbrier West.

The ROI for Long-Term is higher than the Short-Term in Chesapeake with average rental income of $2,576.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake, VA

1439 Thistlewood Lane

Chesapeake, VA

2 beds | 2 baths | 1,727 sq.ft.

$425,000

Airbnb cash on cash: 1.12%

Traditional cash on cash: 2.31%

Airbnb Rental Income: $2309

Traditional Rental Income: $2208

Airbnb ROI: 1.12%

Traditional ROI: 2.31%

4308 Colindale Road #206

Chesapeake, VA

2 beds | 2 baths | 1,367 sq.ft.

$234,000

Airbnb cash on cash: 1.67%

Traditional cash on cash: 6.81%

Airbnb Rental Income: $1309

Traditional Rental Income: $2040

Airbnb ROI: 1.67%

Traditional ROI: 6.81%

829 Donnington Drive

Chesapeake, VA

4 beds | 3 baths | 2,651 sq.ft.

$585,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.98%

Airbnb Rental Income: $null

Traditional Rental Income: $3289

Airbnb ROI: N/A

Traditional ROI: 3.98%

1016 Thoroughgood Way #307

Chesapeake, VA

2 beds | 2 baths | 1,255 sq.ft.

$247,500

Airbnb cash on cash: 2.33%

Traditional cash on cash: 6.32%

Airbnb Rental Income: $1510

Traditional Rental Income: $2004

Airbnb ROI: 2.33%

Traditional ROI: 6.32%

801 Poindexter Street #314

Chesapeake, VA

1 beds | 1 baths | 1,135 sq.ft.

$183,000

Airbnb cash on cash: 2.19%

Traditional cash on cash: 7.14%

Airbnb Rental Income: $1185

Traditional Rental Income: $1661

Airbnb ROI: 2.19%

Traditional ROI: 7.14%

828 Woodstream Way

Chesapeake, VA

4 beds | 3 baths | 2,785 sq.ft.

$594,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.29%

Airbnb Rental Income: $null

Traditional Rental Income: $2971

Airbnb ROI: N/A

Traditional ROI: 3.29%

936A Shoal Creek Trail

Chesapeake, VA

2 beds | 2 baths | 1,589 sq.ft.

$299,900

Airbnb cash on cash: 1.4%

Traditional cash on cash: 4.71%

Airbnb Rental Income: $1502

Traditional Rental Income: $1999

Airbnb ROI: 1.4%

Traditional ROI: 4.71%

800 Monroe Court

Chesapeake, VA

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

$398,000

Airbnb cash on cash: 3.49%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $2762

Traditional Rental Income: $2385

Airbnb ROI: 3.49%