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
5217 Askew Road Chesapeake, VA Solid brick & vinyl ranch in desirable Willow Lakes, Western Branch! This 3BR/2.5BA home s...	3 beds \| 3 baths \| 1,606 sq.ft.	$236,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 6.75% Airbnb Rental Income: $1278 Traditional Rental Income: $2150 Airbnb ROI: 1.04% Traditional ROI: 6.75%
302 Honey Locust Way Chesapeake, VA Welcome to one of Riverwalks finest victorian style homes. As a previous Homearama winner ...	4 beds \| 3 baths \| 3,100 sq.ft.	$675,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 3.42% Airbnb Rental Income: $2019 Traditional Rental Income: $3277 Airbnb ROI: 0.59% Traditional ROI: 3.42%
1813 Sunsprite Loop Chesapeake, VA This Beautiful 4 bedroom 2 1/2 bath traditional style home located in the Landing at Grass...	4 beds \| 3 baths \| 2,446 sq.ft.	$590,999	Airbnb cash on cash: -0.18% Traditional cash on cash: 2.6% Airbnb Rental Income: $1614 Traditional Rental Income: $2693 Airbnb ROI: -0.18% Traditional ROI: 2.6%
4110 Everett Street Chesapeake, VA PRIDE OF OWNERSHIP!!! Spacious four bedroom home with two and a half bathrooms with open f...	4 beds \| 3 baths \| 1,800 sq.ft.	$414,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 4.06% Airbnb Rental Income: $1244 Traditional Rental Income: $2370 Airbnb ROI: 0.15% Traditional ROI: 4.06%
641 Gallbush Road Chesapeake, VA Come View your new home in HICKORY! Spacious 4 bedroom 2 1/2 baths. Open floor plan featur...	4 beds \| 3 baths \| 2,200 sq.ft.	$520,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.8% Airbnb Rental Income: $null Traditional Rental Income: $2385 Airbnb ROI: N/A Traditional ROI: 2.8%
1114 Hoover Avenue Chesapeake, VA Welcome home! This inviting property features a spacious layout with plenty of room to spr...	3 beds \| 2 baths \| 1,332 sq.ft.	$284,850	Airbnb cash on cash: 1.61% Traditional cash on cash: 4.53% Airbnb Rental Income: $1432 Traditional Rental Income: $1790 Airbnb ROI: 1.61% Traditional ROI: 4.53%
1016 Thoroughgood Way #307 Chesapeake, VA Beautifully maintained, one-owner, 3rd-floor condo with elevator access in a secure-entry ...	2 beds \| 2 baths \| 1,255 sq.ft.	$245,000	Airbnb cash on cash: 0% Traditional cash on cash: 6.28% Airbnb Rental Income: $888 Traditional Rental Income: $2004 Airbnb ROI: 0% Traditional ROI: 6.28%
331 Appaloosa Trail Chesapeake, VA Welcome home to a home where comfort, style, and space come together beautifully! This cha...	4 beds \| 3 baths \| 2,148 sq.ft.	$484,999	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.85% Airbnb Rental Income: $1614 Traditional Rental Income: $2673 Airbnb ROI: 0.5% Traditional ROI: 3.85%
404 Vespasian Circle Chesapeake, VA Welcome to 404 Vespasian Circle, a stunning all-brick home located in the highly sought-af...	5 beds \| 3 baths \| 3,446 sq.ft.	$759,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.17% Airbnb Rental Income: $null Traditional Rental Income: $2956 Airbnb ROI: N/A Traditional ROI: 2.17%
608 September Lane Chesapeake, VA Rare attached private in-law suite with a full kitchen! Need multi generational living, it...	5 beds \| 4 baths \| 3,029 sq.ft.	$712,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.02% Airbnb Rental Income: $null Traditional Rental Income: $3312 Airbnb ROI: N/A Traditional ROI: 3.02%
2218 Vicker Avenue Chesapeake, VA Fully remodeled in 2018. This contemporary open floor plan has 2 large living areas and 26...	4 beds \| 2 baths \| 2,692 sq.ft.	$425,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 4.8% Airbnb Rental Income: $2070 Traditional Rental Income: $2730 Airbnb ROI: 1.8% Traditional ROI: 4.8%
918 Seabreeze Court Chesapeake, VA Charming 2-bedroom townhome in the highly desirable Greenbrier area! The main level featur...	2 beds \| 2 baths \| 950 sq.ft.	$254,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 4.37% Airbnb Rental Income: $1127 Traditional Rental Income: $1651 Airbnb ROI: 0.62% Traditional ROI: 4.37%
205 Fresno Drive Chesapeake, VA Absolutely Stunning! Location, Location, Location! Gorgeous 3 bed 2.5 bath home completely...	3 beds \| 3 baths \| 1,700 sq.ft.	$499,900	Airbnb cash on cash: 1.11% Traditional cash on cash: 3.25% Airbnb Rental Income: $1840 Traditional Rental Income: $2343 Airbnb ROI: 1.11% Traditional ROI: 3.25%
915 Harbour N Drive Chesapeake, VA Rare to find an end unit townhome on 0.16 Acre lot in Great Bridge area minutes to freeway...	5 beds \| 3 baths \| 1,916 sq.ft.	$268,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.29% Airbnb Rental Income: $null Traditional Rental Income: $2608 Airbnb ROI: N/A Traditional ROI: 8.29%
3536 Riverwood Crescent Chesapeake, VA Updated farmhouse charm on nearly 4 acres! This traditional home offers 3 bedrooms, 3 full...	3 beds \| 3 baths \| 2,464 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.81% Airbnb Rental Income: $null Traditional Rental Income: $2621 Airbnb ROI: N/A Traditional ROI: 1.81%
2852 Greenview Road Chesapeake, VA Move-in ready 4BR/3BA in sought-after Western Branch! Features include in-ground pool, out...	4 beds \| 3 baths \| 2,546 sq.ft.	$500,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 3.93% Airbnb Rental Income: $2795 Traditional Rental Income: $2844 Airbnb ROI: 2.43% Traditional ROI: 3.93%
717 Inlet Quay #H Chesapeake, VA Move-in ready and ideally located in the heart of Chesapeake! This well-maintained home fe...	2 beds \| 2 baths \| 1,120 sq.ft.	$220,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 5.48% Airbnb Rental Income: $1127 Traditional Rental Income: $1690 Airbnb ROI: 0.96% Traditional ROI: 5.48%
536 Cristfield Road Chesapeake, VA If owning a stunning former model home, with all the bells and whistles, is on your radar....	3 beds \| 3 baths \| 2,003 sq.ft.	$454,500	Airbnb cash on cash: 1.71% Traditional cash on cash: 3.59% Airbnb Rental Income: $2162 Traditional Rental Income: $2412 Airbnb ROI: 1.71% Traditional ROI: 3.59%
434 Granada Drive Chesapeake, VA Welcome home to this beautiful 4-bedroom, 2 bath ranch tucked away on a quiet cul-de-sac i...	4 beds \| 2 baths \| 2,500 sq.ft.	$580,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 2.68% Airbnb Rental Income: $1073 Traditional Rental Income: $2557 Airbnb ROI: -0.74% Traditional ROI: 2.68%
2417 Baum Road Chesapeake, VA Escape to your own private three-acre retreat in the highly sought-after Hickory School Di...	4 beds \| 4 baths \| 3,985 sq.ft.	$895,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.92% Airbnb Rental Income: $null Traditional Rental Income: $3393 Airbnb ROI: N/A Traditional ROI: 1.92%
540 Aylesbury Drive Chesapeake, VA Welcome home to this beautifully maintained 4-bedroom property in the heart of Great Bridg...	4 beds \| 2 baths \| 1,602 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $2257 Airbnb ROI: N/A Traditional ROI: 3.26%
1314 20th Street Chesapeake, VA Well kept & maintained three bedroom ranch with central air, spacious kitchen, living room...	3 beds \| 1 baths \| 960 sq.ft.	$210,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 4.02% Airbnb Rental Income: $1432 Traditional Rental Income: $1607 Airbnb ROI: 0.99% Traditional ROI: 4.02%
1508 Wood Avenue Chesapeake, VA Welcome to 1508 Wood Avenue! This charming 4-bedroom, 2 bath ranch house is move-in ready,...	4 beds \| 2 baths \| 1,739 sq.ft.	$355,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 5.53% Airbnb Rental Income: $2070 Traditional Rental Income: $2565 Airbnb ROI: 2.44% Traditional ROI: 5.53%
1004 Wymers CT Chesapeake, VA Spacious 5-bedroom ranch with finished room over the garage offers a unique natural settin...	5 beds \| 2 baths \| N/A	$485,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.01% Airbnb Rental Income: $null Traditional Rental Income: $2761 Airbnb ROI: N/A Traditional ROI: 4.01%
1904 Keeter RN Chesapeake, VA Exceptional opportunity in sought-after Logans Mill in the heart of Greenbrier. This two-s...	4 beds \| 3 baths \| N/A	$430,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 5.38% Airbnb Rental Income: $2070 Traditional Rental Income: $3045 Airbnb ROI: 1.64% Traditional ROI: 5.38%
1972 Beechwood Road Chesapeake, VA This charming four-bedroom Stephen Alexander Walnut model in the desirable Summer Park com...	4 beds \| 3 baths \| 3,114 sq.ft.	$689,900	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.83% Airbnb Rental Income: $1614 Traditional Rental Income: $3186 Airbnb ROI: -0.33% Traditional ROI: 2.83%
748 Greenwing Drive Chesapeake, VA Welcome to luxury living in the heart of Chesapeake! This stunning all-brick 2-story home ...	4 beds \| 3 baths \| 3,128 sq.ft.	$699,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 2.39% Airbnb Rental Income: $2116 Traditional Rental Income: $2938 Airbnb ROI: 0.3% Traditional ROI: 2.39%
1413 Walnut Avenue Chesapeake, VA Water views, modern updates, and no HOA! Welcome to Norfolk Highlands, where this charming...	2 beds \| 2 baths \| 1,028 sq.ft.	$284,900	Airbnb cash on cash: 1.43% Traditional cash on cash: 4.74% Airbnb Rental Income: $1402 Traditional Rental Income: $1868 Airbnb ROI: 1.43% Traditional ROI: 4.74%
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: 1.56% Traditional cash on cash: 4.8% Airbnb Rental Income: $1398 Traditional Rental Income: $1866 Airbnb ROI: 1.56% Traditional ROI: 4.8%
2041 Lockard Avenue Chesapeake, VA Great starter home! This charming 3-bedroom, 1-bath ranch offers comfortable single-level ...	3 beds \| 1 baths \| 1,000 sq.ft.	$227,900	Airbnb cash on cash: 2.11% Traditional cash on cash: 5.35% Airbnb Rental Income: $1398 Traditional Rental Income: $1675 Airbnb ROI: 2.11% Traditional ROI: 5.35%
1937 Flintshire Drive Chesapeake, VA Welcome to Summer Park at Parkview! This spacious 4-bedroom, 2.5-bath home offers a bright...	4 beds \| 3 baths \| 2,750 sq.ft.	$595,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 2.88% Airbnb Rental Income: $1614 Traditional Rental Income: $2762 Airbnb ROI: -0.01% Traditional ROI: 2.88%
1361 Cypress Place Chesapeake, VA Welcome to 1361 Cypress Place, a beautifully updated contemporary home in the heart of Gre...	3 beds \| 3 baths \| 1,750 sq.ft.	$425,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.41% Airbnb Rental Income: $1398 Traditional Rental Income: $2202 Airbnb ROI: 0.33% Traditional ROI: 3.41%
1453 Whittamore Road Chesapeake, VA 3% Builder-paid Buyer Incentive to be used at Buyer's discretion with Builder's preferred ...	5 beds \| 3 baths \| 2,660 sq.ft.	$719,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.82% Airbnb Rental Income: $null Traditional Rental Income: $2795 Airbnb ROI: N/A Traditional ROI: 2.82%
1523 Pucknall Drive Chesapeake, VA Easy living awaits in this 3-bedroom, 2.5-bath condo in the heart of Greenbrier. The livin...	3 beds \| 3 baths \| 1,870 sq.ft.	$349,900	Airbnb cash on cash: 2.73% Traditional cash on cash: 4.54% Airbnb Rental Income: $2162 Traditional Rental Income: $2209 Airbnb ROI: 2.73% Traditional ROI: 4.54%
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.	$615,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 3% Airbnb Rental Income: $2861 Traditional Rental Income: $2830 Airbnb ROI: 1.89% Traditional ROI: 3%
1603 Seaboard Avenue Chesapeake, VA Two-story traditional in Chesapeake's Quincy Place. 3 beds, 1.5 baths, ~1,360 sq ft. The n...	3 beds \| 2 baths \| 1,360 sq.ft.	$239,500	Airbnb cash on cash: 2.17% Traditional cash on cash: 6.07% Airbnb Rental Income: $1432 Traditional Rental Income: $1887 Airbnb ROI: 2.17% Traditional ROI: 6.07%
237 Cedar Road Chesapeake, VA Rarely does a property like this hit the market in Great Bridge! Sitting on a gated half-a...	5 beds \| 3 baths \| 3,851 sq.ft.	$730,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.33% Airbnb Rental Income: $null Traditional Rental Income: $2913 Airbnb ROI: N/A Traditional ROI: 2.33%
1013 Angora Court Chesapeake, VA Recently Updated & Move-In Ready!Welcome home to this beautifully refreshed property featu...	3 beds \| 2 baths \| 1,724 sq.ft.	$400,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.75% Airbnb Rental Income: $1398 Traditional Rental Income: $2190 Airbnb ROI: 0.51% Traditional ROI: 3.75%
2845 Lambert Trail Chesapeake, VA Beautifully updated ranch-style home situated on a spacious lot in Chesapeake's sought-aft...	3 beds \| 2 baths \| 1,900 sq.ft.	$379,900	Airbnb cash on cash: 1.21% Traditional cash on cash: 4.31% Airbnb Rental Income: $1626 Traditional Rental Income: $2269 Airbnb ROI: 1.21% Traditional ROI: 4.31%
3408 Winterhawk Court Chesapeake, VA Nestled in a fun-friendly quiet cul-de-sac, this well-maintained ranch offers comfortable ...	3 beds \| 2 baths \| 1,368 sq.ft.	$399,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 3.16% Airbnb Rental Income: $1304 Traditional Rental Income: $1978 Airbnb ROI: 0.28% Traditional ROI: 3.16%

Real Estate investment in Chesapeake, VA

There are 558 properties for sale in the city of Chesapeake . The median list price in Chesapeake is $417,547 and the average price per square foot is $184. In July 2026, the average monthly cash on cash return in Chesapeake is 4.00%. The average monthly rental income in Chesapeake is $2,568.

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

There are 558 investment properties available for sale in Chesapeake.

In 2026, the best neighborhood to buy investment property is Indian River.

The ROI for Long-Term is higher than the Short-Term in Chesapeake with average rental income of $2,568.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake, VA

5217 Askew Road

Chesapeake, VA

3 beds | 3 baths | 1,606 sq.ft.

$236,000

Airbnb cash on cash: 1.04%

Traditional cash on cash: 6.75%

Airbnb Rental Income: $1278

Traditional Rental Income: $2150

Airbnb ROI: 1.04%

Traditional ROI: 6.75%

302 Honey Locust Way

Chesapeake, VA

4 beds | 3 baths | 3,100 sq.ft.

$675,000

Airbnb cash on cash: 0.59%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $2019

Traditional Rental Income: $3277

Airbnb ROI: 0.59%

Traditional ROI: 3.42%

1813 Sunsprite Loop

Chesapeake, VA

4 beds | 3 baths | 2,446 sq.ft.

$590,999

Airbnb cash on cash: -0.18%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $1614

Traditional Rental Income: $2693

Airbnb ROI: -0.18%

Traditional ROI: 2.6%

4110 Everett Street

Chesapeake, VA

4 beds | 3 baths | 1,800 sq.ft.

$414,900

Airbnb cash on cash: 0.15%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $1244

Traditional Rental Income: $2370

Airbnb ROI: 0.15%

Traditional ROI: 4.06%

641 Gallbush Road

Chesapeake, VA

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

$520,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.8%

Airbnb Rental Income: $null

Traditional Rental Income: $2385

Airbnb ROI: N/A

Traditional ROI: 2.8%

1114 Hoover Avenue

Chesapeake, VA

3 beds | 2 baths | 1,332 sq.ft.

$284,850

Airbnb cash on cash: 1.61%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $1432

Traditional Rental Income: $1790

Airbnb ROI: 1.61%

Traditional ROI: 4.53%

1016 Thoroughgood Way #307

Chesapeake, VA

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

$245,000

Airbnb cash on cash: 0%

Traditional cash on cash: 6.28%

Airbnb Rental Income: $888

Traditional Rental Income: $2004

Airbnb ROI: 0%

Traditional ROI: 6.28%

331 Appaloosa Trail

Chesapeake, VA

4 beds | 3 baths | 2,148 sq.ft.

$484,999

Airbnb cash on cash: 0.5%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $1614

Traditional Rental Income: $2673

Airbnb ROI: 0.5%