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.

Single Family Homes for Sale in Chesapeake, VA

Search for Single Family Residential for Sale in Chesapeake, Virginia. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 158 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
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%
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%
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%
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%
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%
1703 Landsworth Street Chesapeake, VA Come see this wonderful 4-bedroom, 2-bathroom ranch home tucked away at the end of a quiet...	4 beds \| 2 baths \| 2,000 sq.ft.	$349,999	Airbnb cash on cash: 3.02% Traditional cash on cash: 5.46% Airbnb Rental Income: $2255 Traditional Rental Income: $2490 Airbnb ROI: 3.02% Traditional ROI: 5.46%
1028 Pleasant Ridge Drive Chesapeake, VA Welcome to 1028 Pleasant Ridge Drive, where space, privacy, and comfort come together on a...	4 beds \| 3 baths \| 3,694 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.99% Airbnb Rental Income: $null Traditional Rental Income: $2791 Airbnb ROI: N/A Traditional ROI: 1.99%
1204 Fontana Avenue Chesapeake, VA Make this your first stop! This charming all-brick ranch sits on nearly a quarter-acre lot...	3 beds \| 1 baths \| 1,441 sq.ft.	$345,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 3.7% Airbnb Rental Income: $1824 Traditional Rental Income: $1896 Airbnb ROI: 1.96% Traditional ROI: 3.7%
2708 Horseshoe Drive Chesapeake, VA Completely renovated all-brick ranch offering timeless charm & modern updates throughout! ...	4 beds \| 2 baths \| 1,724 sq.ft.	$485,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.13% Airbnb Rental Income: $null Traditional Rental Income: $2311 Airbnb ROI: N/A Traditional ROI: 3.13%
4207 Neptune Avenue Chesapeake, VA You deserve MORE in a Home and THIS one delivers! This is REALLY (4) Beds & (3) Baths! Thi...	3 beds \| 2 baths \| 1,472 sq.ft.	$374,900	Airbnb cash on cash: 1.62% Traditional cash on cash: 3.75% Airbnb Rental Income: $1824 Traditional Rental Income: $2079 Airbnb ROI: 1.62% Traditional ROI: 3.75%
508 Mooney Road Chesapeake, VA Move-in ready Chesapeake ranch with major system updates buyers will appreciate. A new HVA...	3 beds \| 2 baths \| 1,400 sq.ft.	$299,900	Airbnb cash on cash: 2.51% Traditional cash on cash: 4.9% Airbnb Rental Income: $1824 Traditional Rental Income: $2004 Airbnb ROI: 2.51% Traditional ROI: 4.9%
1535 Lyons Avenue Chesapeake, VA Charming ranch home with 3 bedrooms and 1.5 bathrooms, new LVP flooring and paint, and ove...	3 beds \| 2 baths \| 1,620 sq.ft.	$325,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 5.56% Airbnb Rental Income: $1824 Traditional Rental Income: $2324 Airbnb ROI: 2.31% Traditional ROI: 5.56%
909 Portland Street Chesapeake, VA NEWER HVAC, UPDATED KITCHEN, NEW PLUMBING, EV CHARGING STATION! And the YARD!! Welcome Hom...	4 beds \| 3 baths \| 2,196 sq.ft.	$420,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 3.36% Airbnb Rental Income: $1692 Traditional Rental Income: $2177 Airbnb ROI: 0.93% Traditional ROI: 3.36%
3916 Port Road Chesapeake, VA Welcome home to this beautifully maintained property featuring a spacious, well appointed ...	3 beds \| 2 baths \| 1,800 sq.ft.	$365,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 3.46% Airbnb Rental Income: $1788 Traditional Rental Income: $1868 Airbnb ROI: 1.8% Traditional ROI: 3.46%
3036 Bomar Drive Chesapeake, VA Updated ranch in Western Branch with open floor plan. Kitchen has beautiful granite counte...	3 beds \| 2 baths \| 1,462 sq.ft.	$350,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 4.55% Airbnb Rental Income: $1495 Traditional Rental Income: $2185 Airbnb ROI: 1.12% Traditional ROI: 4.55%
2307 Tybee Loop Chesapeake, VA Welcome to this beautifully upgraded Dogwood, built by Wirth, at 2307 Tybee Loop, built in...	4 beds \| 3 baths \| 2,808 sq.ft.	$600,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 2.67% Airbnb Rental Income: $3254 Traditional Rental Income: $2729 Airbnb ROI: 2.3% Traditional ROI: 2.67%
3727 Hardwick Terrace Chesapeake, VA Welcome Home to this charming and up to date ranch in the desirable Point Elizabeth sectio...	4 beds \| 2 baths \| 1,834 sq.ft.	$469,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 3.4% Airbnb Rental Income: $2079 Traditional Rental Income: $2397 Airbnb ROI: 1.46% Traditional ROI: 3.4%
1114 Ferebee Avenue Chesapeake, VA Welcome home to this well-maintained 3-bedroom, 2-bath ranch in the established community ...	3 beds \| 2 baths \| 1,368 sq.ft.	$310,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 4.6% Airbnb Rental Income: $1840 Traditional Rental Income: $1959 Airbnb ROI: 2.49% Traditional ROI: 4.6%
4310 Cromwell Avenue Chesapeake, VA This charming 3 bedroom, 1 bath home offers an open floor plan with cathedral ceilings whi...	3 beds \| 1 baths \| 864 sq.ft.	$276,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 3.73% Airbnb Rental Income: $1824 Traditional Rental Income: $1532 Airbnb ROI: 2.96% Traditional ROI: 3.73%
549 Broad Bend Circle Chesapeake, VA Don't miss your opportunity to grab the home of your dreams! You will love lounging on the...	3 beds \| 3 baths \| 2,294 sq.ft.	$432,500	Airbnb cash on cash: 0.94% Traditional cash on cash: 3.87% Airbnb Rental Income: $1866 Traditional Rental Income: $2553 Airbnb ROI: 0.94% Traditional ROI: 3.87%
1323 Ormer Road Chesapeake, VA Welcome home to this beautifully maintained 3-bedroom, 2-full-bath ranch in the heart of C...	3 beds \| 2 baths \| 1,248 sq.ft.	$320,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 4.33% Airbnb Rental Income: $1824 Traditional Rental Income: $1972 Airbnb ROI: 2.2% Traditional ROI: 4.33%
1817 Sparrow Road Chesapeake, VA Opportunity awaits in this Chesapeake home with plenty of potential to make it your own. F...	4 beds \| 2 baths \| 1,092 sq.ft.	$310,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 4.78% Airbnb Rental Income: $2255 Traditional Rental Income: $2024 Airbnb ROI: 3.64% Traditional ROI: 4.78%
804 Greenspring Court Chesapeake, VA Tucked away on a quiet wooded cul-de-sac in Brandermill, this quality-built 4-bedroom, 2-b...	4 beds \| 2 baths \| 1,813 sq.ft.	$479,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.33% Airbnb Rental Income: $null Traditional Rental Income: $2401 Airbnb ROI: N/A Traditional ROI: 3.33%
825 Loblolly Court Chesapeake, VA Crafted with forever-home intention and workmanship, where refined design and quiet luxury...	4 beds \| 2 baths \| 1,700 sq.ft.	$529,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.69% Airbnb Rental Income: $null Traditional Rental Income: $2325 Airbnb ROI: N/A Traditional ROI: 2.69%
1210 Welles Court Chesapeake, VA Conveniently located in the heart of Chesapeake's Greenbrier area, this attractive 3 bedro...	3 beds \| 2 baths \| 1,417 sq.ft.	$365,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 3.59% Airbnb Rental Income: $1824 Traditional Rental Income: $1997 Airbnb ROI: 1.65% Traditional ROI: 3.59%
4528 Davids Mill Drive Chesapeake, VA Come see this beautiful one-level brick home that offers an excellent blend of comfort, en...	4 beds \| 3 baths \| 2,439 sq.ft.	$535,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 4.75% Airbnb Rental Income: $3254 Traditional Rental Income: $3434 Airbnb ROI: 2.92% Traditional ROI: 4.75%
624 Rock Drive Chesapeake, VA Make this your first stop! This beautifully updated brick ranch in the desirable Oak Manor...	4 beds \| 2 baths \| 2,460 sq.ft.	$439,900	Airbnb cash on cash: 2.06% Traditional cash on cash: 3.89% Airbnb Rental Income: $2337 Traditional Rental Income: $2513 Airbnb ROI: 2.06% Traditional ROI: 3.89%
4108 Santa Maria Drive Chesapeake, VA Welcome to this charming, all brick Ranch located in the highly sought after Chadswyck Ter...	3 beds \| 2 baths \| 1,391 sq.ft.	$399,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 3.24% Airbnb Rental Income: $1788 Traditional Rental Income: $1994 Airbnb ROI: 1.39% Traditional ROI: 3.24%
1089 Saint Julian Drive Chesapeake, VA Wonderfully updated and absolutely meticulously maintained and spotless ranch style home w...	4 beds \| 2 baths \| 1,233 sq.ft.	$374,900	Airbnb cash on cash: 2.96% Traditional cash on cash: 3.84% Airbnb Rental Income: $2337 Traditional Rental Income: $2068 Airbnb ROI: 2.96% Traditional ROI: 3.84%
2406 Drum Creek Road Chesapeake, VA Well-maintained 4-bedroom, 2.5 bath all-brick ranch situated on a beautifully landscaped 1...	4 beds \| 3 baths \| 1,612 sq.ft.	$399,000	Airbnb cash on cash: 2.12% Traditional cash on cash: 5.03% Airbnb Rental Income: $2079 Traditional Rental Income: $2632 Airbnb ROI: 2.12% Traditional ROI: 5.03%
809 Grantham Lane Chesapeake, VA Welcome home to this beautifully updated ranch in the highly desirable Hickory School Dist...	4 beds \| 2 baths \| 2,081 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.99% Airbnb Rental Income: $null Traditional Rental Income: $2501 Airbnb ROI: N/A Traditional ROI: 2.99%
609 Crystal Avenue Chesapeake, VA Welcome home to this charming all-brick ranch offering the ease of one-level living! Move-...	3 beds \| 2 baths \| 1,716 sq.ft.	$310,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 5.63% Airbnb Rental Income: $1824 Traditional Rental Income: $2275 Airbnb ROI: 2.39% Traditional ROI: 5.63%
832 Parapet Road Chesapeake, VA Nestled in Chesapeake's established Camelot neighborhood, this beautifully updated vinyl a...	4 beds \| 2 baths \| 1,762 sq.ft.	$379,999	Airbnb cash on cash: 2.81% Traditional cash on cash: 3.8% Airbnb Rental Income: $2337 Traditional Rental Income: $2112 Airbnb ROI: 2.81% Traditional ROI: 3.8%
1920 Ames Circle W Chesapeake, VA Look no further than this charming, beautifully remodeled mini-homestead ranch in the midd...	4 beds \| 2 baths \| 1,735 sq.ft.	$414,900	Airbnb cash on cash: 4.41% Traditional cash on cash: 4.01% Airbnb Rental Income: $3254 Traditional Rental Income: $2370 Airbnb ROI: 4.41% Traditional ROI: 4.01%
MM Myrtle Chesapeake, VA A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style ...	4 beds \| 2 baths \| 2,183 sq.ft.	$539,900	Airbnb cash on cash: 0.93% Traditional cash on cash: 3.16% Airbnb Rental Income: $2079 Traditional Rental Income: $2673 Airbnb ROI: 0.93% Traditional ROI: 3.16%
1107 Sean Drive Chesapeake, VA Don't miss your chance to own this beautiful and tastefully updated home in Deep Creek. Th...	4 beds \| 2 baths \| 1,950 sq.ft.	$372,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 4.85% Airbnb Rental Income: $2337 Traditional Rental Income: $2433 Airbnb ROI: 2.92% Traditional ROI: 4.85%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chesapeake, VA

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%

858 Waters Road

Chesapeake, VA

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%

2218 Vicker Avenue

Chesapeake, VA

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%

540 Aylesbury Drive

Chesapeake, VA

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%

905 Shillelagh Road

Chesapeake, VA

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

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

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

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%