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 322 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
3212 Guenevere Drive Chesapeake, VA Welcome home to this 1751 square foot ranch on a huge corner lot! This 3 bedroom/2 bathroo...	3 beds \| 2 baths \| 1,751 sq.ft.	$325,000	Airbnb cash on cash: 3.57% Traditional cash on cash: 5.16% Airbnb Rental Income: $2305 Traditional Rental Income: $2216 Airbnb ROI: 3.57% Traditional ROI: 5.16%
1310 Virginia Avenue Chesapeake, VA Come visit this awesome, newly renovated home in Ardmore! The spacious living room opens u...	4 beds \| 3 baths \| 1,750 sq.ft.	$359,900	Airbnb cash on cash: 7.26% Traditional cash on cash: 3.96% Airbnb Rental Income: $3999 Traditional Rental Income: $2028 Airbnb ROI: 7.26% Traditional ROI: 3.96%
4176 Williamson Street Chesapeake, VA Charming and cozy, this small bungalow offers the perfect blend of modern updates and conv...	3 beds \| 2 baths \| 1,404 sq.ft.	$258,900	Airbnb cash on cash: 8.82% Traditional cash on cash: 6.83% Airbnb Rental Income: $3346 Traditional Rental Income: $2112 Airbnb ROI: 8.82% Traditional ROI: 6.83%
2706 Fenway Avenue Chesapeake, VA What's not to love? 3 bedroom, 2 bathroom ranch home situated in quiet neighborhood on .67...	3 beds \| 2 baths \| 1,200 sq.ft.	$324,900	Airbnb cash on cash: 3.54% Traditional cash on cash: 4.66% Airbnb Rental Income: $2305 Traditional Rental Income: $2073 Airbnb ROI: 3.54% Traditional ROI: 4.66%
4631 Captain Carter Circle Chesapeake, VA Welcome to this beautiful, 2-story home featuring 4-bedrooms, 2.5-bathrooms. As you approa...	4 beds \| 3 baths \| 2,250 sq.ft.	$445,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 5.32% Airbnb Rental Income: $4041 Traditional Rental Income: $3130 Airbnb ROI: 5.44% Traditional ROI: 5.32%
641 Gallbush Road Chesapeake, VA Gorgeous New Construction in Hickory, open floor plan with family room flowing into kitche...	4 beds \| 3 baths \| 2,200 sq.ft.	$529,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.04% Airbnb Rental Income: $null Traditional Rental Income: $2385 Airbnb ROI: N/A Traditional ROI: 3.04%
668 Luther Street Chesapeake, VA Attractive 3BR/2BA ranch style home with water views on a dead end street in Great Bridge....	3 beds \| 2 baths \| 1,500 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.2% Airbnb Rental Income: $null Traditional Rental Income: $2214 Airbnb ROI: N/A Traditional ROI: 4.2%
409 Granada Drive Chesapeake, VA Stunning home located in the highly sought-after Las Gaviotas subdivision. Tucked away in ...	4 beds \| 3 baths \| 2,461 sq.ft.	$530,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 4.04% Airbnb Rental Income: $1048 Traditional Rental Income: $3042 Airbnb ROI: -0.72% Traditional ROI: 4.04%
2904 Kilbride Drive Chesapeake, VA Investors Opportunity! This 3- bedroom 1 bathroom bungalow is fantastic addition to any po...	3 beds \| 1 baths \| 950 sq.ft.	$220,000	Airbnb cash on cash: 9.81% Traditional cash on cash: 5% Airbnb Rental Income: $3268 Traditional Rental Income: $1534 Airbnb ROI: 9.81% Traditional ROI: 5%
4117 Pinta Drive Chesapeake, VA Wow! This gorgeous 4-bedroom home in desirable Western Branch feels like new! Brand new HV...	4 beds \| 2 baths \| 1,848 sq.ft.	$399,900	Airbnb cash on cash: 6.45% Traditional cash on cash: 4.42% Airbnb Rental Income: $4041 Traditional Rental Income: $2418 Airbnb ROI: 6.45% Traditional ROI: 4.42%
229 Northview Drive Chesapeake, VA Beautiful brick ranch located on 1/3-acre corner lot in the highly desirable and well esta...	3 beds \| 2 baths \| 1,777 sq.ft.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $2410 Airbnb ROI: N/A Traditional ROI: 3.51%
2344 Paramont Avenue Chesapeake, VA This is the one you have been waiting for! Well cared for home with tons of charm. Nicely ...	3 beds \| 2 baths \| 1,641 sq.ft.	$325,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 4.46% Airbnb Rental Income: $3268 Traditional Rental Income: $2024 Airbnb ROI: 6.13% Traditional ROI: 4.46%
947 Scenic Boulevard Chesapeake, VA STUNNING FULLY RENOVATED HOME ON 3.5+ ACRES WITH A BEAUTIFUL WATER VIEW! Welcome to your ...	3 beds \| 3 baths \| 2,232 sq.ft.	$675,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.15% Airbnb Rental Income: $null Traditional Rental Income: $3082 Airbnb ROI: N/A Traditional ROI: 3.15%
1029 Johnstown Road Chesapeake, VA Over 1 acre of land! New roof in February of this year! On the first floor of this beautif...	4 beds \| 3 baths \| 1,980 sq.ft.	$475,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 4.48% Airbnb Rental Income: $1048 Traditional Rental Income: $2820 Airbnb ROI: -0.32% Traditional ROI: 4.48%
3005 Barn Way Chesapeake, VA This stunning ranch has been tastefully updated with new paint, updated lighting, and new ...	4 beds \| 3 baths \| 1,500 sq.ft.	$374,900	Airbnb cash on cash: 5.36% Traditional cash on cash: 4.36% Airbnb Rental Income: $3341 Traditional Rental Income: $2243 Airbnb ROI: 5.36% Traditional ROI: 4.36%
1029 Harwich Drive Chesapeake, VA Beautiful 4 bedroom 3.5 bathroom house in desirable Chesapeake location. Gorgeous open lay...	4 beds \| 4 baths \| 3,502 sq.ft.	$689,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $4101 Airbnb ROI: N/A Traditional ROI: 4.33%
2444 Johnstown Road Chesapeake, VA Welcome to your dream farmhouse retreat at 2444 Johnstown Road! This beautiful four-bedroo...	4 beds \| 3 baths \| 2,443 sq.ft.	$620,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $3063 Airbnb ROI: N/A Traditional ROI: 3.29%
1812 Rollis Road Chesapeake, VA Home sweet home! Recently upgraded brick ranch in a quiet cul-de-sac located in the desira...	3 beds \| 2 baths \| 1,207 sq.ft.	$335,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 4.47% Airbnb Rental Income: $2144 Traditional Rental Income: $2079 Airbnb ROI: 2.94% Traditional ROI: 4.47%
2805 Princeton Avenue Chesapeake, VA Welcome to 2805 Princeton Ave. in beautiful Chesapeake, VA! This charming 2-bedroom, home ...	2 beds \| 1 baths \| 1,040 sq.ft.	$244,900	Airbnb cash on cash: 8.28% Traditional cash on cash: 5.38% Airbnb Rental Income: $3130 Traditional Rental Income: $1749 Airbnb ROI: 8.28% Traditional ROI: 5.38%
3000 Stratford Drive Chesapeake, VA Look no further for your oasis.. This place is ready to be called HOME in the sought-after...	4 beds \| 3 baths \| 2,631 sq.ft.	$520,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 3.83% Airbnb Rental Income: $3885 Traditional Rental Income: $2799 Airbnb ROI: 4.34% Traditional ROI: 3.83%
1530 Jackson Avenue Chesapeake, VA Discover an updated 1922 classic home featuring 3 bedrooms and 2.5 baths across 1,820 sq f...	3 beds \| 3 baths \| 1,820 sq.ft.	$275,000	Airbnb cash on cash: 7.92% Traditional cash on cash: 7.36% Airbnb Rental Income: $3346 Traditional Rental Income: $2455 Airbnb ROI: 7.92% Traditional ROI: 7.36%
932 Sir Lancelot Drive Chesapeake, VA Enjoy being tucked away in the back of a quiet neighborhood. This ranch is move in ready! ...	3 beds \| 2 baths \| 1,388 sq.ft.	$330,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 4.29% Airbnb Rental Income: $2305 Traditional Rental Income: $1977 Airbnb ROI: 3.5% Traditional ROI: 4.29%
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: 7.24% Traditional cash on cash: 4.8% Airbnb Rental Income: $3268 Traditional Rental Income: $1866 Airbnb ROI: 7.24% Traditional ROI: 4.8%
2 Harbor Watch Drive #702 Chesapeake, VA A completely renovated 3-bedroom, 2-bath first-floor condo, just under 1,800 sqft, located...	3 beds \| 2 baths \| 1,740 sq.ft.	$299,000	Airbnb cash on cash: 7.33% Traditional cash on cash: 5.57% Airbnb Rental Income: $3471 Traditional Rental Income: $2208 Airbnb ROI: 7.33% Traditional ROI: 5.57%
100 Foster Court Chesapeake, VA Experience carefree living in this stunning 3 BR 2 BA single-family detached condo. This l...	3 beds \| 2 baths \| 1,450 sq.ft.	$299,900	Airbnb cash on cash: 6.75% Traditional cash on cash: 4.94% Airbnb Rental Income: $3268 Traditional Rental Income: $2022 Airbnb ROI: 6.75% Traditional ROI: 4.94%
809 Custis Avenue Chesapeake, VA Good opportunity to live in a quiet small family neighborhood. Property has had some upgra...	3 beds \| 1 baths \| 1,320 sq.ft.	$239,900	Airbnb cash on cash: 5.24% Traditional cash on cash: 5.49% Airbnb Rental Income: $2305 Traditional Rental Income: $1787 Airbnb ROI: 5.24% Traditional ROI: 5.49%
3941 Ahoy Drive Chesapeake, VA Welcome to this beautiful and well-maintained brick ranch, perfectly nestled in the desira...	3 beds \| 1 baths \| 1,225 sq.ft.	$269,900	Airbnb cash on cash: 4.1% Traditional cash on cash: 4.32% Airbnb Rental Income: $2144 Traditional Rental Income: $1653 Airbnb ROI: 4.1% Traditional ROI: 4.32%
3004 Sunrise Avenue Chesapeake, VA Investment opportunity. Most likely will require cash or 203k loan. Also potential VA loan...	3 beds \| 2 baths \| 1,400 sq.ft.	$250,000	Airbnb cash on cash: 8.33% Traditional cash on cash: 6.34% Airbnb Rental Income: $3268 Traditional Rental Income: $2063 Airbnb ROI: 8.33% Traditional ROI: 6.34%
1316 18th Street Chesapeake, VA Better than renting... this 3 bedroom home with a yard is great for a busy lifestyle.Â Fr...	3 beds \| 3 baths \| 1,384 sq.ft.	$269,000	Airbnb cash on cash: 8.03% Traditional cash on cash: 6.06% Airbnb Rental Income: $3346 Traditional Rental Income: $2099 Airbnb ROI: 8.03% Traditional ROI: 6.06%
1308 Seaboard Avenue Chesapeake, VA Stop by and tour this home nestled in Chesapeake, Virginia. The primary bedroom is located...	4 beds \| 3 baths \| 2,002 sq.ft.	$383,000	Airbnb cash on cash: 6.79% Traditional cash on cash: 5.38% Airbnb Rental Income: $3999 Traditional Rental Income: $2638 Airbnb ROI: 6.79% Traditional ROI: 5.38%
306 Cotton Mill Court Chesapeake, VA Move-in ready! Come see this gorgeously updated 4 bed/2 bath ranch & make it âhome!â T...	4 beds \| 2 baths \| 1,600 sq.ft.	$365,000	Airbnb cash on cash: 5.45% Traditional cash on cash: 5.08% Airbnb Rental Income: $3341 Traditional Rental Income: $2470 Airbnb ROI: 5.45% Traditional ROI: 5.08%
731 OSBORN Avenue Chesapeake, VA Come see this adorable, unique and charming 3 bedroom, 2 bath home centrally located in Ch...	3 beds \| 2 baths \| 1,300 sq.ft.	$265,000	Airbnb cash on cash: 7.87% Traditional cash on cash: 6.03% Airbnb Rental Income: $3268 Traditional Rental Income: $2076 Airbnb ROI: 7.87% Traditional ROI: 6.03%
2724 Cedar Road Chesapeake, VA Experience luxury in this stunning new construction home that sits on an extra large lot, ...	4 beds \| 3 baths \| 2,550 sq.ft.	$629,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.03% Airbnb Rental Income: $null Traditional Rental Income: $2829 Airbnb ROI: N/A Traditional ROI: 3.03%
1004 Pernell Lane Chesapeake, VA Welcome home to the perfect blend of style and functionality! You will love entertaining i...	4 beds \| 4 baths \| 2,767 sq.ft.	$620,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $3102 Airbnb ROI: N/A Traditional ROI: 3.29%
807 Falls Creek Drive Chesapeake, VA Welcome to this desirable waterfront community in Chesapeake. This stunning single-family ...	5 beds \| 3 baths \| 3,338 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.38% Airbnb Rental Income: $null Traditional Rental Income: $3046 Airbnb ROI: N/A Traditional ROI: 2.38%
1512 Chesapeake Avenue Chesapeake, VA This charming Chesapeake neighborhood offers convenient access to military bases, shopping...	4 beds \| 2 baths \| 2,226 sq.ft.	$340,000	Airbnb cash on cash: 7.73% Traditional cash on cash: 5.33% Airbnb Rental Income: $3999 Traditional Rental Income: $2377 Airbnb ROI: 7.73% Traditional ROI: 5.33%
3315 Merlin Court Chesapeake, VA Step through the inviting front door, and be prepared to be captivated by the warmth and l...	3 beds \| 2 baths \| 1,536 sq.ft.	$345,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 4.17% Airbnb Rental Income: $2305 Traditional Rental Income: $2036 Airbnb ROI: 3.23% Traditional ROI: 4.17%
703 Stalham Road Chesapeake, VA Please bring your buyers to see this beautiful, quaint 3 bedroom, 2 bathroom ranch style p...	3 beds \| 2 baths \| 1,300 sq.ft.	$310,000	Airbnb cash on cash: 6.57% Traditional cash on cash: 5.27% Airbnb Rental Income: $3268 Traditional Rental Income: $2154 Airbnb ROI: 6.57% Traditional ROI: 5.27%
1310 Commerce Avenue Chesapeake, VA Rich LVP creates a warm, polished canvas where your fresh start awaits you! Fall in love w...	3 beds \| 3 baths \| 1,472 sq.ft.	$304,000	Airbnb cash on cash: 7.02% Traditional cash on cash: 4.14% Airbnb Rental Income: $3346 Traditional Rental Income: $1774 Airbnb ROI: 7.02% Traditional ROI: 4.14%
1017 Bowling Green Trail Chesapeake, VA Spacious split level home in the neighborhood of Clearfield in the heart of Chesapeake. Ce...	4 beds \| 3 baths \| 1,829 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $2530 Airbnb ROI: N/A Traditional ROI: 4.32%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chesapeake, VA

3212 Guenevere Drive

Chesapeake, VA

3 beds | 2 baths | 1,751 sq.ft.

$325,000

Airbnb cash on cash: 3.57%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $2305

Traditional Rental Income: $2216

Airbnb ROI: 3.57%

Traditional ROI: 5.16%

1310 Virginia Avenue

Chesapeake, VA

4 beds | 3 baths | 1,750 sq.ft.

$359,900

Airbnb cash on cash: 7.26%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $3999

Traditional Rental Income: $2028

Airbnb ROI: 7.26%

Traditional ROI: 3.96%

4176 Williamson Street

Chesapeake, VA

3 beds | 2 baths | 1,404 sq.ft.

$258,900

Airbnb cash on cash: 8.82%

Traditional cash on cash: 6.83%

Airbnb Rental Income: $3346

Traditional Rental Income: $2112

Airbnb ROI: 8.82%

Traditional ROI: 6.83%

2706 Fenway Avenue

Chesapeake, VA

3 beds | 2 baths | 1,200 sq.ft.

$324,900

Airbnb cash on cash: 3.54%

Traditional cash on cash: 4.66%

Airbnb Rental Income: $2305

Traditional Rental Income: $2073

Airbnb ROI: 3.54%

Traditional ROI: 4.66%

4631 Captain Carter Circle

Chesapeake, VA

4 beds | 3 baths | 2,250 sq.ft.

$445,000

Airbnb cash on cash: 5.44%

Traditional cash on cash: 5.32%

Airbnb Rental Income: $4041

Traditional Rental Income: $3130

Airbnb ROI: 5.44%

Traditional ROI: 5.32%

641 Gallbush Road

Chesapeake, VA

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

$529,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.04%

Airbnb Rental Income: $null

Traditional Rental Income: $2385

Airbnb ROI: N/A

Traditional ROI: 3.04%

668 Luther Street

Chesapeake, VA

3 beds | 2 baths | 1,500 sq.ft.

$385,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.2%

Airbnb Rental Income: $null

Traditional Rental Income: $2214

Airbnb ROI: N/A

Traditional ROI: 4.2%

409 Granada Drive

Chesapeake, VA

4 beds | 3 baths | 2,461 sq.ft.

$530,000

Airbnb cash on cash: -0.72%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $1048

Traditional Rental Income: $3042

Airbnb ROI: -0.72%