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
905 Rosana Court Chesapeake, VA Stop and look at this beautiful quality home in the heart of the desired Great Bridge area...	4 beds \| 3 baths \| 2,317 sq.ft.	$550,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 2.93% Airbnb Rental Income: $1240 Traditional Rental Income: $2619 Airbnb ROI: -0.53% Traditional ROI: 2.93%
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.	$665,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 3.49% Airbnb Rental Income: $1763 Traditional Rental Income: $3277 Airbnb ROI: 0.27% Traditional ROI: 3.49%
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: 0.56% Traditional cash on cash: 2.6% Airbnb Rental Income: $2107 Traditional Rental Income: $2693 Airbnb ROI: 0.56% 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: 1.11% Traditional cash on cash: 4.06% Airbnb Rental Income: $1692 Traditional Rental Income: $2370 Airbnb ROI: 1.11% Traditional ROI: 4.06%
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: 2.87% Traditional cash on cash: 4.53% Airbnb Rental Income: $1840 Traditional Rental Income: $1790 Airbnb ROI: 2.87% Traditional ROI: 4.53%
829 Donnington Drive Chesapeake, VA Welcome home to this beautifully updated 4-bedroom, 2.5-bath ranch in the desirable Ethrid...	4 beds \| 3 baths \| 2,651 sq.ft.	$609,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $3289 Airbnb ROI: N/A Traditional ROI: 3.75%
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.	$244,500	Airbnb cash on cash: 1.27% Traditional cash on cash: 6.3% Airbnb Rental Income: $1239 Traditional Rental Income: $2004 Airbnb ROI: 1.27% Traditional ROI: 6.3%
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: 1.41% Traditional cash on cash: 3.85% Airbnb Rental Income: $2107 Traditional Rental Income: $2673 Airbnb ROI: 1.41% Traditional ROI: 3.85%
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.	$540,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 2.63% Airbnb Rental Income: $1240 Traditional Rental Income: $2321 Airbnb ROI: -0.29% Traditional ROI: 2.63%
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.	$754,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.19% Airbnb Rental Income: $null Traditional Rental Income: $2956 Airbnb ROI: N/A Traditional ROI: 2.19%
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: 2.19% Traditional cash on cash: 4.8% Airbnb Rental Income: $2255 Traditional Rental Income: $2730 Airbnb ROI: 2.19% 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: 2.15% Traditional cash on cash: 4.37% Airbnb Rental Income: $1569 Traditional Rental Income: $1651 Airbnb ROI: 2.15% 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: 1.73% Traditional cash on cash: 3.25% Airbnb Rental Income: $2189 Traditional Rental Income: $2343 Airbnb ROI: 1.73% 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%
3618 Point Elizabeth Drive Chesapeake, VA Welcome to luxury living in this stunning all-brick home with an incredible backyard sanct...	4 beds \| 3 baths \| 3,000 sq.ft.	$650,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 2.99% Airbnb Rental Income: $2079 Traditional Rental Income: $2978 Airbnb ROI: 0.62% Traditional ROI: 2.99%
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: 0.69% Traditional cash on cash: 1.81% Airbnb Rental Income: $2428 Traditional Rental Income: $2621 Airbnb ROI: 0.69% 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: 1.15% Traditional cash on cash: 3.93% Airbnb Rental Income: $2079 Traditional Rental Income: $2844 Airbnb ROI: 1.15% 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.	$210,000	Airbnb cash on cash: 2.91% Traditional cash on cash: 5.78% Airbnb Rental Income: $1569 Traditional Rental Income: $1690 Airbnb ROI: 2.91% Traditional ROI: 5.78%
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: 1.43% Traditional cash on cash: 3.59% Airbnb Rental Income: $2021 Traditional Rental Income: $2412 Airbnb ROI: 1.43% Traditional ROI: 3.59%
2828 Seven Eleven Road Chesapeake, VA Welcome to your private country retreat! Nestled on 3 beautiful acres in the desirable Gra...	4 beds \| 3 baths \| 2,192 sq.ft.	$644,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.38% Airbnb Rental Income: $null Traditional Rental Income: $2627 Airbnb ROI: N/A Traditional ROI: 2.38%
4209 Quailshire Court Chesapeake, VA Opportunity awaits in Western Branch! Nestled in a quiet cul-de-sac, this home offers soli...	4 beds \| 3 baths \| 2,272 sq.ft.	$350,000	Airbnb cash on cash: 5.19% Traditional cash on cash: 6.55% Airbnb Rental Income: $3254 Traditional Rental Income: $2968 Airbnb ROI: 5.19% Traditional ROI: 6.55%
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%
500 Landmark Court Chesapeake, VA Nestled on a spacious, landscaped corner lot in sought-after Cedar Crossing, this updated ...	4 beds \| 3 baths \| 2,103 sq.ft.	$470,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 4.51% Airbnb Rental Income: $1240 Traditional Rental Income: $2932 Airbnb ROI: -0.23% Traditional ROI: 4.51%
905 Shillelagh Road Chesapeake, VA Welcome home to this charming four-bedroom ranch featuring a spacious, open floor plan des...	4 beds \| 2 baths \| 1,877 sq.ft.	$374,900	Airbnb cash on cash: 2.13% Traditional cash on cash: 4.62% Airbnb Rental Income: $2107 Traditional Rental Income: $2441 Airbnb ROI: 2.13% Traditional ROI: 4.62%
106 Greenbrier Road Chesapeake, VA Cute 1 story cottage in the heart of Greenbrier Chesapeake on almost an acre of private wo...	3 beds \| 1 baths \| 1,100 sq.ft.	$288,500	Airbnb cash on cash: 2.83% Traditional cash on cash: 3.75% Airbnb Rental Income: $1866 Traditional Rental Income: $1616 Airbnb ROI: 2.83% Traditional ROI: 3.75%
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: 2.02% Traditional cash on cash: 5.38% Airbnb Rental Income: $2255 Traditional Rental Income: $3045 Airbnb ROI: 2.02% 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: 0.31% Traditional cash on cash: 2.83% Airbnb Rental Income: $2107 Traditional Rental Income: $3186 Airbnb ROI: 0.31% 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.	$698,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 2.4% Airbnb Rental Income: $2337 Traditional Rental Income: $2938 Airbnb ROI: 0.59% Traditional ROI: 2.4%
801 Poindexter Street #318 Chesapeake, VA Come See This One Level Studio Condo That Offers Comfortable Low Maintenance Living With T...	1 beds \| 1 baths \| 980 sq.ft.	$155,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 8.75% Airbnb Rental Income: $1027 Traditional Rental Income: $1684 Airbnb ROI: 1.88% Traditional ROI: 8.75%
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: 3.76% Traditional cash on cash: 5.35% Airbnb Rental Income: $1824 Traditional Rental Income: $1675 Airbnb ROI: 3.76% 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.	$575,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.02% Airbnb Rental Income: $2107 Traditional Rental Income: $2762 Airbnb ROI: 0.79% Traditional ROI: 3.02%
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: 1.22% Traditional cash on cash: 3.41% Airbnb Rental Income: $1824 Traditional Rental Income: $2202 Airbnb ROI: 1.22% 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%
424 Pines Of Warrick Drive Chesapeake, VA Welcome to this remarkable Pines of Warrick home in highly sought-after Great Bridge-affec...	4 beds \| 3 baths \| 2,366 sq.ft.	$560,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 3.33% Airbnb Rental Income: $1240 Traditional Rental Income: $2809 Airbnb ROI: -0.42% Traditional ROI: 3.33%
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: 2.37% Traditional cash on cash: 4.54% Airbnb Rental Income: $2021 Traditional Rental Income: $2209 Airbnb ROI: 2.37% 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: 2.46% Traditional cash on cash: 3% Airbnb Rental Income: $3254 Traditional Rental Income: $2830 Airbnb ROI: 2.46% 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.	$234,500	Airbnb cash on cash: 3.77% Traditional cash on cash: 6.21% Airbnb Rental Income: $1840 Traditional Rental Income: $1887 Airbnb ROI: 3.77% Traditional ROI: 6.21%
712 Appalachian Court Chesapeake, VA Move right into this beautifully upgraded, detached single-family home that perfectly pair...	3 beds \| 3 baths \| 2,389 sq.ft.	$615,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 2.34% Airbnb Rental Income: $2021 Traditional Rental Income: $2540 Airbnb ROI: 0.52% Traditional ROI: 2.34%
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%
2720 Deerfield Crescent Chesapeake, VA Experience refined living in the sought after Western Branch area, where timeless design m...	4 beds \| 3 baths \| 2,574 sq.ft.	$550,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 3.11% Airbnb Rental Income: $2079 Traditional Rental Income: $2586 Airbnb ROI: 1.08% Traditional ROI: 3.11%

Real Estate investment in Chesapeake, VA

There are 543 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 $185. In August 2026, the average monthly cash on cash return in Chesapeake is 4.00%. The average monthly rental income in Chesapeake is $2,537.

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

There are 543 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 $2,537.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake, VA

905 Rosana Court

Chesapeake, VA

4 beds | 3 baths | 2,317 sq.ft.

$550,000

Airbnb cash on cash: -0.53%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $1240

Traditional Rental Income: $2619

Airbnb ROI: -0.53%

Traditional ROI: 2.93%

302 Honey Locust Way

Chesapeake, VA

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

$665,000

Airbnb cash on cash: 0.27%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $1763

Traditional Rental Income: $3277

Airbnb ROI: 0.27%

Traditional ROI: 3.49%

1813 Sunsprite Loop

Chesapeake, VA

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

$590,999

Airbnb cash on cash: 0.56%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $2107

Traditional Rental Income: $2693

Airbnb ROI: 0.56%

Traditional ROI: 2.6%

4110 Everett Street

Chesapeake, VA

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

$414,900

Airbnb cash on cash: 1.11%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $1692

Traditional Rental Income: $2370

Airbnb ROI: 1.11%

Traditional ROI: 4.06%

1114 Hoover Avenue

Chesapeake, VA

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

$284,850

Airbnb cash on cash: 2.87%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $1840

Traditional Rental Income: $1790

Airbnb ROI: 2.87%

Traditional ROI: 4.53%

829 Donnington Drive

Chesapeake, VA

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

$609,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.75%

Airbnb Rental Income: $null

Traditional Rental Income: $3289

Airbnb ROI: N/A

Traditional ROI: 3.75%

1016 Thoroughgood Way #307

Chesapeake, VA

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

$244,500

Airbnb cash on cash: 1.27%

Traditional cash on cash: 6.3%

Airbnb Rental Income: $1239

Traditional Rental Income: $2004

Airbnb ROI: 1.27%

Traditional ROI: 6.3%

331 Appaloosa Trail

Chesapeake, VA

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

$484,999

Airbnb cash on cash: 1.41%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $2107

Traditional Rental Income: $2673

Airbnb ROI: 1.41%