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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1349 Great Bridge Boulevard Chesapeake, VA Welcome home to this beautifully updated 3-bedroom, 2-bath gem offering the perfect blend ...	3 beds \| 2 baths \| 1,360 sq.ft.	$315,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 4.35% Airbnb Rental Income: $1311 Traditional Rental Income: $1920 Airbnb ROI: 0.92% Traditional ROI: 4.35%
812 Hardwood Drive Chesapeake, VA Welcome to this beautifully maintained 4-bedroom, 3 full bath ranch in the highly desirabl...	4 beds \| 3 baths \| 1,921 sq.ft.	$440,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 3.94% Airbnb Rental Income: $2199 Traditional Rental Income: $2573 Airbnb ROI: 1.68% Traditional ROI: 3.94%
2809 Halsey Street Chesapeake, VA Welcome to this beautifully renovated 3-bedroom, 2-bathroom gem in the heart of Chesapeake...	3 beds \| 2 baths \| 1,040 sq.ft.	$314,999	Airbnb cash on cash: 1.29% Traditional cash on cash: 4.36% Airbnb Rental Income: $1432 Traditional Rental Income: $1914 Airbnb ROI: 1.29% Traditional ROI: 4.36%
1000 York Drive Chesapeake, VA Here is the cutest 4-bedroom ranch you'll find in Greenbrier, tucked on a quiet cul-de-sac...	4 beds \| 3 baths \| 1,682 sq.ft.	$435,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 3.84% Airbnb Rental Income: $2199 Traditional Rental Income: $2400 Airbnb ROI: 1.98% Traditional ROI: 3.84%
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.	$435,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 4.67% Airbnb Rental Income: $2070 Traditional Rental Income: $2730 Airbnb ROI: 1.74% Traditional ROI: 4.67%
2501 Cayce Drive Chesapeake, VA Charming 3-bedroom, 1-bath home offering 825 square feet of comfortable living space on a ...	3 beds \| 1 baths \| 825 sq.ft.	$245,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 4.26% Airbnb Rental Income: $1398 Traditional Rental Income: $1522 Airbnb ROI: 1.9% Traditional ROI: 4.26%
3313 Dodd Drive Chesapeake, VA Welcome Home! Step into this stunning home featuring soaring ceilings and a chef inspired ...	4 beds \| 3 baths \| 2,862 sq.ft.	$550,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 3.9% Airbnb Rental Income: $1614 Traditional Rental Income: $3014 Airbnb ROI: 0.28% Traditional ROI: 3.9%
207 McCosh Drive Chesapeake, VA Come check out this beautiful all brick ranch style home right in the heart of Chesapeake ...	3 beds \| 2 baths \| 1,410 sq.ft.	$358,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 3.88% Airbnb Rental Income: $1311 Traditional Rental Income: $2013 Airbnb ROI: 0.58% Traditional ROI: 3.88%
4925 Vico Drive Chesapeake, VA Well-maintained 3-bedroom, 2-bath single-level ranch on a cul-de-sac in the sought-after W...	3 beds \| 2 baths \| 1,630 sq.ft.	$400,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 3.16% Airbnb Rental Income: $1278 Traditional Rental Income: $1974 Airbnb ROI: 0.23% Traditional ROI: 3.16%
526 Wittington Drive Chesapeake, VA Meticulously maintained ranch on large corner lot in the heart of Great Bridge. Enjoy Rela...	4 beds \| 3 baths \| 2,500 sq.ft.	$584,900	Airbnb cash on cash: -0.8% Traditional cash on cash: 2.78% Airbnb Rental Income: $965 Traditional Rental Income: $2567 Airbnb ROI: -0.8% Traditional ROI: 2.78%
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.	$460,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.16% Airbnb Rental Income: $null Traditional Rental Income: $2257 Airbnb ROI: N/A Traditional ROI: 3.16%
1737 Sparrow Road Chesapeake, VA Well-maintained and ideally located close to shopping, restaurants, schools, and everyday ...	3 beds \| 2 baths \| 1,215 sq.ft.	$344,500	Airbnb cash on cash: 0.88% Traditional cash on cash: 3.5% Airbnb Rental Income: $1398 Traditional Rental Income: $1824 Airbnb ROI: 0.88% Traditional ROI: 3.5%
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%
1004 Wymers Court Chesapeake, VA Spacious 5-bedroom ranch with finished room over the garage offers a unique natural settin...	5 beds \| 2 baths \| 2,073 sq.ft.	$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.	$749,900	Airbnb cash on cash: 0.27% Traditional cash on cash: 2.43% Airbnb Rental Income: $1942 Traditional Rental Income: $2938 Airbnb ROI: 0.27% Traditional ROI: 2.43%
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%
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.	$300,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 6.17% Airbnb Rental Income: $2070 Traditional Rental Income: $2480 Airbnb ROI: 2.82% Traditional ROI: 6.17%
2041 Lockard Avenue Chesapeake, VA Great investment opportunity! This 3 bedroom, 1 bath ranch comes with a tenant in place th...	3 beds \| 1 baths \| 1,000 sq.ft.	$230,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 5.29% Airbnb Rental Income: $1398 Traditional Rental Income: $1675 Airbnb ROI: 2.08% Traditional ROI: 5.29%
2718 Gum Road Chesapeake, VA Welcome to 2718 Gum Road in Chesapeake! This spacious 4-bedroom, 2.5-bath home offers the ...	4 beds \| 3 baths \| 2,856 sq.ft.	$585,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 3.08% Airbnb Rental Income: $2795 Traditional Rental Income: $2780 Airbnb ROI: 1.91% Traditional ROI: 3.08%
3941 Sextant Street Chesapeake, VA Welcome home to 3941 Sextant St in Chesapeake! This charming ranch-style home offers the p...	4 beds \| 2 baths \| 1,485 sq.ft.	$329,500	Airbnb cash on cash: 4.95% Traditional cash on cash: 4.98% Airbnb Rental Income: $2861 Traditional Rental Income: $2206 Airbnb ROI: 4.95% Traditional ROI: 4.98%
1328 Keaton Way Chesapeake, VA Discover this stunning, updated ranch nestled in the vibrant heart of Western Branch! This...	3 beds \| 2 baths \| 1,450 sq.ft.	$360,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 4.11% Airbnb Rental Income: $1278 Traditional Rental Income: $2107 Airbnb ROI: 0.47% Traditional ROI: 4.11%
1519 Rodgers Street Chesapeake, VA Welcome to this stunningly remodeled home in the heart of South Norfolk Historic District,...	3 beds \| 2 baths \| 1,474 sq.ft.	$319,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 4.65% Airbnb Rental Income: $1432 Traditional Rental Income: $2022 Airbnb ROI: 1.26% Traditional ROI: 4.65%
1103 Santeetlah Ave Chesapeake, VA Welcome home to this charming brick ranch in sought after Indian River Estates! Offering 4...	4 beds \| 1 baths \| 1,325 sq.ft.	$324,999	Airbnb cash on cash: 2.87% Traditional cash on cash: 3.98% Airbnb Rental Income: $2070 Traditional Rental Income: $1875 Airbnb ROI: 2.87% Traditional ROI: 3.98%
3232 White Cedar Drive Chesapeake, VA Nestled on a desirable corner lot in the heart of Deep Creek, this charming ranch offers t...	4 beds \| 2 baths \| 1,834 sq.ft.	$419,900	Airbnb cash on cash: 0.8% Traditional cash on cash: 3.97% Airbnb Rental Income: $1614 Traditional Rental Income: $2404 Airbnb ROI: 0.8% Traditional ROI: 3.97%
2113 Hollins Court Chesapeake, VA Must See First! Welcome to this beautifully maintained all-brick ranch home tucked away on...	3 beds \| 2 baths \| 1,618 sq.ft.	$390,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 3.63% Airbnb Rental Income: $1398 Traditional Rental Income: $2076 Airbnb ROI: 0.62% Traditional ROI: 3.63%
1632 Head Of River Road Chesapeake, VA Welcome to 1632 Head of River Rd. This ranch sits on a half acre lot, complete with a fenc...	3 beds \| 2 baths \| 1,440 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.89% Airbnb Rental Income: $null Traditional Rental Income: $1943 Airbnb ROI: N/A Traditional ROI: 2.89%
1819 Martin Avenue Chesapeake, VA THIS IS A PLACE YOU CAN CALL HOME. Solid brick home in a cul-de-sac offering durability, t...	3 beds \| 2 baths \| 1,250 sq.ft.	$210,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 7.92% Airbnb Rental Income: $1432 Traditional Rental Income: $2085 Airbnb ROI: 2.49% Traditional ROI: 7.92%
566 River Creek Road Chesapeake, VA Take a look at this charming 3 bedroom, 1.5 bath ranch! This home has been updated kitchen...	3 beds \| 2 baths \| 1,379 sq.ft.	$340,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 3.25% Airbnb Rental Income: $1432 Traditional Rental Income: $1734 Airbnb ROI: 0.97% Traditional ROI: 3.25%
711 Waterstock Court Chesapeake, VA Hickory School District - Prime Location!!! Conveniently located near the bypass and shopp...	3 beds \| 2 baths \| 1,791 sq.ft.	$480,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 2.81% Airbnb Rental Income: $1290 Traditional Rental Income: $2242 Airbnb ROI: -0.21% Traditional ROI: 2.81%
909 Portland Street Chesapeake, VA Welcome Home to 909 Portland Street in Chesapeake! This spacious and beautifully maintaine...	4 beds \| 3 baths \| 2,196 sq.ft.	$420,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 3.36% Airbnb Rental Income: $1244 Traditional Rental Income: $2177 Airbnb ROI: -0.02% Traditional ROI: 3.36%
416 Keith Court Chesapeake, VA Welcome home to this adorable 3-bedroom brick ranch offering classic charm and everyday co...	3 beds \| 1 baths \| 1,050 sq.ft.	$220,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 5.64% Airbnb Rental Income: $1398 Traditional Rental Income: $1691 Airbnb ROI: 2.21% Traditional ROI: 5.64%
2307 Tybee Loop Chesapeake, VA Welcome to this beautifully upgraded Dogwood, built by Wirth, at 2307 Tybee Loop, built in...	4 beds \| 3 baths \| 3,261 sq.ft.	$600,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 2.67% Airbnb Rental Income: $2861 Traditional Rental Income: $2729 Airbnb ROI: 1.72% Traditional ROI: 2.67%
1021 Fentress Road Chesapeake, VA Rare Double Lot in a Highly Sought-After School District! Discover unparalleled outdoor sp...	3 beds \| 2 baths \| 1,414 sq.ft.	$429,900	Airbnb cash on cash: 0.11% Traditional cash on cash: 2.91% Airbnb Rental Income: $1290 Traditional Rental Income: $2011 Airbnb ROI: 0.11% Traditional ROI: 2.91%
1119 Kings Mill Court Chesapeake, VA ASSUMABLE VA LOAN- For those who qualify. Welcome home to this beautiful 3-bedroom, 2-bath...	3 beds \| 2 baths \| 1,600 sq.ft.	$375,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.6% Airbnb Rental Income: $1311 Traditional Rental Income: $2057 Airbnb ROI: 0.33% Traditional ROI: 3.6%
2305 Shorebird Court Chesapeake, VA Located in one of the most desirable parts of Deep Creek and within the highly sought-afte...	4 beds \| 2 baths \| 1,688 sq.ft.	$465,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 3.67% Airbnb Rental Income: $1614 Traditional Rental Income: $2493 Airbnb ROI: 0.6% Traditional ROI: 3.67%
2701 Omar Street Chesapeake, VA A charming three-bedroom, two-bath single-story residence situated on a corner lot. The pr...	3 beds \| 2 baths \| 1,200 sq.ft.	$285,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 5.83% Airbnb Rental Income: $1432 Traditional Rental Income: $2171 Airbnb ROI: 1.48% Traditional ROI: 5.83%
3924 Port Road Chesapeake, VA This modern brick ranch showcases a truly unique family touch, thoughtfully built and lovi...	4 beds \| 2 baths \| 1,600 sq.ft.	$300,000	Airbnb cash on cash: 5.55% Traditional cash on cash: 5.71% Airbnb Rental Income: $2861 Traditional Rental Income: $2241 Airbnb ROI: 5.55% Traditional ROI: 5.71%
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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chesapeake, VA

1349 Great Bridge Boulevard

Chesapeake, VA

3 beds | 2 baths | 1,360 sq.ft.

$315,000

Airbnb cash on cash: 0.92%

Traditional cash on cash: 4.35%

Airbnb Rental Income: $1311

Traditional Rental Income: $1920

Airbnb ROI: 0.92%

Traditional ROI: 4.35%

812 Hardwood Drive

Chesapeake, VA

4 beds | 3 baths | 1,921 sq.ft.

$440,000

Airbnb cash on cash: 1.68%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $2199

Traditional Rental Income: $2573

Airbnb ROI: 1.68%

Traditional ROI: 3.94%

2809 Halsey Street

Chesapeake, VA

3 beds | 2 baths | 1,040 sq.ft.

$314,999

Airbnb cash on cash: 1.29%

Traditional cash on cash: 4.36%

Airbnb Rental Income: $1432

Traditional Rental Income: $1914

Airbnb ROI: 1.29%

Traditional ROI: 4.36%

1000 York Drive

Chesapeake, VA

4 beds | 3 baths | 1,682 sq.ft.

$435,000

Airbnb cash on cash: 1.98%

Traditional cash on cash: 3.84%

Airbnb Rental Income: $2199

Traditional Rental Income: $2400

Airbnb ROI: 1.98%

Traditional ROI: 3.84%

2218 Vicker Avenue

Chesapeake, VA

4 beds | 2 baths | 2,692 sq.ft.

$435,000

Airbnb cash on cash: 1.74%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $2070

Traditional Rental Income: $2730

Airbnb ROI: 1.74%

Traditional ROI: 4.67%

2501 Cayce Drive

Chesapeake, VA

3 beds | 1 baths | 825 sq.ft.

$245,000

Airbnb cash on cash: 1.9%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $1398

Traditional Rental Income: $1522

Airbnb ROI: 1.9%

Traditional ROI: 4.26%

3313 Dodd Drive

Chesapeake, VA

4 beds | 3 baths | 2,862 sq.ft.

$550,000

Airbnb cash on cash: 0.28%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $1614

Traditional Rental Income: $3014

Airbnb ROI: 0.28%

Traditional ROI: 3.9%

207 McCosh Drive

Chesapeake, VA

3 beds | 2 baths | 1,410 sq.ft.

$358,000

Airbnb cash on cash: 0.58%

Traditional cash on cash: 3.88%

Airbnb Rental Income: $1311

Traditional Rental Income: $2013

Airbnb ROI: 0.58%