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
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%
1924 ELBOW Road Chesapeake, VA BEAUTIFUL COUNTRY HOME ON 5.82 ACRES. THIS PARCEL MUST BE PURCHASED ALONG W/ADDITIONAL 58 ...	3 beds \| 3 baths \| 2,357 sq.ft.	$340,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 5.62% Airbnb Rental Income: $2870 Traditional Rental Income: $2537 Airbnb ROI: 4.57% Traditional ROI: 5.62%
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%
1011 Middle Street Chesapeake, VA Four bedroom home with an open floor plan! Newly painted and all new carpet. Large kitche...	4 beds \| 3 baths \| 2,028 sq.ft.	$369,900	Airbnb cash on cash: 6.88% Traditional cash on cash: 5.16% Airbnb Rental Income: $3999 Traditional Rental Income: $2546 Airbnb ROI: 6.88% Traditional ROI: 5.16%
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%
600 Rathwell Court N Chesapeake, VA This charming ranch home is nestled on a spacious .36-acre corner lot. Step inside to find...	4 beds \| 3 baths \| 2,112 sq.ft.	$524,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $2544 Airbnb ROI: N/A Traditional ROI: 3.22%
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%
1519 Scoonie Pointe Drive #116 Chesapeake, VA Eagle Point is a gated community for 55 and over at Cahoon Plantation: It features a 1ST F...	3 beds \| 3 baths \| 1,870 sq.ft.	$394,900	Airbnb cash on cash: 7.27% Traditional cash on cash: 3.75% Airbnb Rental Income: $4428 Traditional Rental Income: $2200 Airbnb ROI: 7.27% Traditional ROI: 3.75%
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%
1500 Blade Court Chesapeake, VA This gorgeous home is located in the heart of Chesapeake near many shopping centers and re...	4 beds \| 3 baths \| 4,082 sq.ft.	$940,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.42% Airbnb Rental Income: $null Traditional Rental Income: $2992 Airbnb ROI: N/A Traditional ROI: 1.42%
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%
929 Washington Drive Chesapeake, VA Welcome to 929 Washington Drive in the desirable Grassfield High School district! This bea...	4 beds \| 3 baths \| 2,024 sq.ft.	$520,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 3.29% Airbnb Rental Income: $1048 Traditional Rental Income: $2585 Airbnb ROI: -0.62% Traditional ROI: 3.29%
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.	$379,700	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.29% Airbnb Rental Income: $3341 Traditional Rental Income: $2243 Airbnb ROI: 5.28% Traditional ROI: 4.29%
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%
200 Essex Drive Chesapeake, VA Come see this charming 4 bed 2 bath brick rancher in Chesapeake. When you enter the home, ...	4 beds \| 2 baths \| 2,200 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.89% Airbnb Rental Income: $null Traditional Rental Income: $2540 Airbnb ROI: N/A Traditional ROI: 4.89%
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%
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%
1205 Glen Landing Chesapeake, VA Incredible one of a kind home on river in Deep Creek Chesapeake. 3 years old with tons of ...	5 beds \| 4 baths \| 2,604 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.45% Airbnb Rental Income: $null Traditional Rental Income: $3475 Airbnb ROI: N/A Traditional ROI: 4.45%
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.	$249,900	Airbnb cash on cash: 5% Traditional cash on cash: 5.23% Airbnb Rental Income: $2305 Traditional Rental Income: $1787 Airbnb ROI: 5% Traditional ROI: 5.23%
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%
1812 Elizabeth Avenue Chesapeake, VA This delightful traditional home features 3 bedrooms and 2.5 bathrooms, offering comfortab...	3 beds \| 3 baths \| 2,004 sq.ft.	$365,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.83% Airbnb Rental Income: $3346 Traditional Rental Income: $2389 Airbnb ROI: 5.44% Traditional ROI: 4.83%
3719 Cannon Point Drive Chesapeake, VA Beautiful, move-in ready home with water and marsh views, with no flood insurance required...	4 beds \| 3 baths \| 1,924 sq.ft.	$450,000	Airbnb cash on cash: 5.17% Traditional cash on cash: 4.27% Airbnb Rental Income: $3885 Traditional Rental Income: $2671 Airbnb ROI: 5.17% Traditional ROI: 4.27%
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%
4605 Trapshoot Court Chesapeake, VA Welcome to your new home! This exquisite 2-story, 3-bedroom condo has just been totally re...	3 beds \| 3 baths \| 1,703 sq.ft.	$299,000	Airbnb cash on cash: 5.6% Traditional cash on cash: 5.03% Airbnb Rental Income: $2824 Traditional Rental Income: $2003 Airbnb ROI: 5.6% Traditional ROI: 5.03%
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%
4330 Oneford Place Chesapeake, VA Experience comfort and elegance in this spacious 3-bedroom, 2.5-bathroom condominium situa...	3 beds \| 3 baths \| 1,875 sq.ft.	$289,500	Airbnb cash on cash: 5.67% Traditional cash on cash: 6.57% Airbnb Rental Income: $2824 Traditional Rental Income: $2410 Airbnb ROI: 5.67% Traditional ROI: 6.57%

Real Estate investment in Chesapeake, VA

There are 379 properties for sale in the city of Chesapeake . The median list price in Chesapeake is $400,000 and the average price per square foot is $189. In December 2024, the average monthly cash on cash return in Chesapeake is 4.00%. The average monthly rental income in Chesapeake is $2,463.

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

There are 379 investment properties available for sale in Chesapeake.

In 2024, the best neighborhood to buy investment property is Greenbrier West.

The ROI for Short-Term is higher than the Long-Term in Chesapeake with average rental income of $3,341.

Your search for investment property begins and ends here

Investment Property 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%

1924 ELBOW Road

Chesapeake, VA

3 beds | 3 baths | 2,357 sq.ft.

$340,000

Airbnb cash on cash: 4.57%

Traditional cash on cash: 5.62%

Airbnb Rental Income: $2870

Traditional Rental Income: $2537

Airbnb ROI: 4.57%

Traditional ROI: 5.62%

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%

1011 Middle Street

Chesapeake, VA

4 beds | 3 baths | 2,028 sq.ft.

$369,900

Airbnb cash on cash: 6.88%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $3999

Traditional Rental Income: $2546

Airbnb ROI: 6.88%