Real Estate Investments for Sale in Chesapeake, VA With High ROI

Are you looking for a vacation rental in Chesapeake, VA? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

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
1792 Cedar Road Chesapeake, VA Experience the PERFECT BLEND OF HISTORIC ELEGANCE AND MODERN LUXURY with this 1860s Coloni...	4 beds \| 2 baths \| 3,200 sq.ft.	$619,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.81% Airbnb Rental Income: $null Traditional Rental Income: $2834 Airbnb ROI: N/A Traditional ROI: 2.81%
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: 5.94% Traditional cash on cash: 5.22% Airbnb Rental Income: $3395 Traditional Rental Income: $2412 Airbnb ROI: 5.94% Traditional ROI: 5.22%
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: 8.15% Traditional cash on cash: 6.23% Airbnb Rental Income: $3149 Traditional Rental Income: $1967 Airbnb ROI: 8.15% Traditional ROI: 6.23%
4225 Terry Drive Chesapeake, VA Well maintained home just across from school complex. Brand new HVAC system, windows less ...	4 beds \| 2 baths \| 2,073 sq.ft.	$400,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 4.01% Airbnb Rental Income: $3767 Traditional Rental Income: $2283 Airbnb ROI: 5.79% Traditional ROI: 4.01%
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.	$519,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.12% Airbnb Rental Income: $null Traditional Rental Income: $2385 Airbnb ROI: N/A Traditional ROI: 3.12%
904 Anna Joy Court Chesapeake, VA Beautiful all brick custom home w/in-ground pool located in the desirable Kemp Woods neigh...	4 beds \| 3 baths \| 3,112 sq.ft.	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.47% Airbnb Rental Income: $null Traditional Rental Income: $3464 Airbnb ROI: N/A Traditional ROI: 3.47%
816 Gilchrist Ct Chesapeake, VA Buy this home and if YOU ARE NOT SATISFIED in 24 Months I'LL BUY IT BACK or SELL IT FOR FR...	4 beds \| 4 baths \| 3,782 sq.ft.	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.15% Airbnb Rental Income: $null Traditional Rental Income: $2928 Airbnb ROI: N/A Traditional ROI: 2.15%
933 Washington Drive Chesapeake, VA Beautiful Open Concept Living in what feels like the country of Chesapeake without giving ...	4 beds \| 3 baths \| 2,474 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $2725 Airbnb ROI: N/A Traditional ROI: 3.26%
4307 Oneford Place Chesapeake, VA Beautiful contemporary design with open-concept floor plan flooded with natural light. Lar...	3 beds \| 3 baths \| 1,952 sq.ft.	$315,000	Airbnb cash on cash: 6.42% Traditional cash on cash: 6.23% Airbnb Rental Income: $3179 Traditional Rental Income: $2405 Airbnb ROI: 6.42% Traditional ROI: 6.23%
218 Wildlife Trace Chesapeake, VA	4 beds \| 3 baths \| 2,682 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $2994 Airbnb ROI: N/A Traditional ROI: 3.35%
807 Riddlehurst Avenue Chesapeake, VA Fabulous Corner Townhouse Style Condo in the Heart of Greenbrier! All Brick and Move in Re...	2 beds \| 3 baths \| 1,568 sq.ft.	$300,000	Airbnb cash on cash: 6.82% Traditional cash on cash: 3.98% Airbnb Rental Income: $3518 Traditional Rental Income: $1941 Airbnb ROI: 6.82% Traditional ROI: 3.98%
500 Judah Way #135 Chesapeake, VA Beautiful 2-BR 2.5-bath condo in sought after Greenbrier. This condo has 2 primary bedroom...	2 beds \| 3 baths \| 1,500 sq.ft.	$279,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 5.48% Airbnb Rental Income: $2589 Traditional Rental Income: $1981 Airbnb ROI: 5.44% Traditional ROI: 5.48%
2610 Omar Street Chesapeake, VA Discover this beautifully updated ranch, offering a perfect blend of modern features and c...	3 beds \| 3 baths \| 1,350 sq.ft.	$279,900	Airbnb cash on cash: 7.26% Traditional cash on cash: 6.03% Airbnb Rental Income: $3149 Traditional Rental Income: $2112 Airbnb ROI: 7.26% Traditional ROI: 6.03%
3908 Wortham Court E Chesapeake, VA Step into your next chapter in this charming 2-story home in Chesapeake! With 4 cozy bedro...	4 beds \| 2 baths \| 1,443 sq.ft.	$325,000	Airbnb cash on cash: 5.77% Traditional cash on cash: 4.63% Airbnb Rental Income: $3077 Traditional Rental Income: $2028 Airbnb ROI: 5.77% Traditional ROI: 4.63%
1316 Blackwater Road Chesapeake, VA Charming brick ranch on beautiful one acre lot that is absolutely great for animals, cooko...	3 beds \| 3 baths \| 1,400 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.65% Airbnb Rental Income: $null Traditional Rental Income: $2220 Airbnb ROI: N/A Traditional ROI: 3.65%
924 Brandermill Drive Chesapeake, VA Brick Ranch located in the Hickory School District of Chesapeake. Updated home features 4...	4 beds \| 2 baths \| 1,745 sq.ft.	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.48% Airbnb Rental Income: $null Traditional Rental Income: $2432 Airbnb ROI: N/A Traditional ROI: 3.48%
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.	$379,900	Airbnb cash on cash: 4.66% Traditional cash on cash: 4.15% Airbnb Rental Income: $3077 Traditional Rental Income: $2195 Airbnb ROI: 4.66% Traditional ROI: 4.15%
1717 Rock Bridge Mews #A Chesapeake, VA Location, Location, Location. This Cozy ground level condo is conveniently located in the...	2 beds \| 1 baths \| 822 sq.ft.	$197,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.28% Airbnb Rental Income: $null Traditional Rental Income: $1442 Airbnb ROI: N/A Traditional ROI: 5.28%
2444 Johnstown Road Chesapeake, VA Welcome home to 2444 Johnstown Road in Chesapeake! This spacious ranch offers an open conc...	4 beds \| 3 baths \| 2,443 sq.ft.	$640,000	Airbnb cash on cash: 7.86% Traditional cash on cash: 3.37% Airbnb Rental Income: $7270 Traditional Rental Income: $3187 Airbnb ROI: 7.86% Traditional ROI: 3.37%
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.	$337,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.88% Airbnb Rental Income: $null Traditional Rental Income: $1905 Airbnb ROI: N/A Traditional ROI: 3.88%
708 Beckley Lane Chesapeake, VA Beautiful, well built, and well maintained, brick ranch w/ 4 bedrooms and 3 full baths, lo...	4 beds \| 3 baths \| 2,200 sq.ft.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 4% Airbnb Rental Income: $null Traditional Rental Income: $2848 Airbnb ROI: N/A Traditional ROI: 4%
425 Longdale Crescent Chesapeake, VA Nestled in a serene neighborhood, this charming partial brick home is situated on a large ...	4 beds \| 3 baths \| 2,130 sq.ft.	$374,900	Airbnb cash on cash: 7.61% Traditional cash on cash: 5.12% Airbnb Rental Income: $4359 Traditional Rental Income: $2568 Airbnb ROI: 7.61% Traditional ROI: 5.12%
2501 Knox Court Chesapeake, VA This beautiful 4bedroom plus flex room, 3.5 bath home is situated in a peaceful cul-de-sac...	5 beds \| 4 baths \| 2,518 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.02% Airbnb Rental Income: $null Traditional Rental Income: $3093 Airbnb ROI: N/A Traditional ROI: 6.02%
932 Sir Lancelot Drive Chesapeake, VA Seller requires rent back until March 15, 2025. Enjoy being tucked away in the back of...	3 beds \| 2 baths \| 1,388 sq.ft.	$340,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 3.55% Airbnb Rental Income: $2190 Traditional Rental Income: $1790 Airbnb ROI: 3.07% Traditional ROI: 3.55%
2019 Texas Street Chesapeake, VA The yard is where it's at with this home! Perfect for family get togethers, hosting partie...	4 beds \| 2 baths \| 2,759 sq.ft.	$449,900	Airbnb cash on cash: 3.51% Traditional cash on cash: 5.06% Airbnb Rental Income: $3077 Traditional Rental Income: $3030 Airbnb ROI: 3.51% Traditional ROI: 5.06%
2220 Engle Avenue Chesapeake, VA Welcome Home! This inviting 4-bedroom, 3 full bath residence with 2 Ensuites' one located ...	4 beds \| 3 baths \| 2,000 sq.ft.	$385,000	Airbnb cash on cash: 7.42% Traditional cash on cash: 5.01% Airbnb Rental Income: $4359 Traditional Rental Income: $2572 Airbnb ROI: 7.42% Traditional ROI: 5.01%
1220 Quarter Path Trail Chesapeake, VA Seller offering a $5,000 credit on an acceptable offer for closing costs or improvements. ...	3 beds \| 3 baths \| 1,722 sq.ft.	$365,000	Airbnb cash on cash: 4.26% Traditional cash on cash: 3.6% Airbnb Rental Income: $2876 Traditional Rental Income: $1984 Airbnb ROI: 4.26% Traditional ROI: 3.6%
917 Godwin Avenue Chesapeake, VA Welcome Home! This home offers a perfect blend of comfort and style. Enjoy the ease and ac...	3 beds \| 2 baths \| 1,650 sq.ft.	$335,000	Airbnb cash on cash: 5.78% Traditional cash on cash: 4.14% Airbnb Rental Income: $3149 Traditional Rental Income: $1921 Airbnb ROI: 5.78% Traditional ROI: 4.14%
324 Cobblewood Arch Chesapeake, VA Centrally located townhome located in Dominion Pines. This property has one of the largest...	2 beds \| 1 baths \| 940 sq.ft.	$235,000	Airbnb cash on cash: 6.7% Traditional cash on cash: 4.16% Airbnb Rental Income: $2589 Traditional Rental Income: $1403 Airbnb ROI: 6.7% Traditional ROI: 4.16%
537 Seahorse Run Chesapeake, VA Enjoy this 3 bedroom, 3 bath condo with lots of natural lighting! The kitchen features sta...	3 beds \| 3 baths \| 1,769 sq.ft.	$285,000	Airbnb cash on cash: 5.82% Traditional cash on cash: 5.26% Airbnb Rental Income: $2876 Traditional Rental Income: $2056 Airbnb ROI: 5.82% Traditional ROI: 5.26%
3941 Ahoy Drive Chesapeake, VA Welcome to your dream home! This well maintained 3-bedroom, 1-bath brick ranch, nestled in...	3 beds \| 1 baths \| 1,225 sq.ft.	$276,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.59% Airbnb Rental Income: $null Traditional Rental Income: $1754 Airbnb ROI: N/A Traditional ROI: 4.59%
1272 Kingsway Drive Chesapeake, VA Renovated & ready for new owner! Great location in the heart of greenbrier, close to inter...	3 beds \| 3 baths \| 1,711 sq.ft.	$475,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 3.96% Airbnb Rental Income: $2876 Traditional Rental Income: $2622 Airbnb ROI: 3.03% Traditional ROI: 3.96%
1106 Corden Avenue Chesapeake, VA Welcome Home!! 1106 Corden Ave features an open floor plan with plenty of room to host fam...	3 beds \| 3 baths \| 2,271 sq.ft.	$348,000	Airbnb cash on cash: 5.33% Traditional cash on cash: 5.89% Airbnb Rental Income: $3149 Traditional Rental Income: $2618 Airbnb ROI: 5.33% Traditional ROI: 5.89%
1703 Landsworth Street Chesapeake, VA Our home is unique and has future opportunity to grow your money! The property consists of...	4 beds \| 2 baths \| 2,000 sq.ft.	$349,000	Airbnb cash on cash: 8.43% Traditional cash on cash: 5.52% Airbnb Rental Income: $4359 Traditional Rental Income: $2490 Airbnb ROI: 8.43% Traditional ROI: 5.52%
1904 Kelly Run Chesapeake, VA This 4-bedroom, 3-bathroom home offers the perfect blend of comfort and convenience. Locat...	4 beds \| 3 baths \| 1,936 sq.ft.	$435,000	Airbnb cash on cash: 6.38% Traditional cash on cash: 4.22% Airbnb Rental Income: $4359 Traditional Rental Income: $2564 Airbnb ROI: 6.38% Traditional ROI: 4.22%
1249 George Washington Highway N Chesapeake, VA CHECK OUT THIS FENCED IN BACK YARD!!! So much room for activities. This beautiful remodele...	5 beds \| 3 baths \| 2,000 sq.ft.	$389,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $2708 Airbnb ROI: N/A Traditional ROI: 5.19%
2248 Cedar Road Chesapeake, VA This newly remodeled brick ranch home, located in the desirable Grassfield school district...	3 beds \| 2 baths \| 1,541 sq.ft.	$365,900	Airbnb cash on cash: 8.41% Traditional cash on cash: 3.93% Airbnb Rental Income: $4567 Traditional Rental Income: $2079 Airbnb ROI: 8.41% Traditional ROI: 3.93%
1321 Eagles Trace Path #D Chesapeake, VA The perfect space and location. Walk into this home to a large foyer and stairway that l...	3 beds \| 2 baths \| 1,591 sq.ft.	$314,900	Airbnb cash on cash: 6.7% Traditional cash on cash: 4.12% Airbnb Rental Income: $3395 Traditional Rental Income: $1878 Airbnb ROI: 6.7% Traditional ROI: 4.12%
3228 Duquesne Drive Chesapeake, VA Prime location! Convenient access to interstate, shopping, and dining. Highly sought-after...	4 beds \| 3 baths \| 2,823 sq.ft.	$520,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 3.15% Airbnb Rental Income: $3767 Traditional Rental Income: $2553 Airbnb ROI: 3.97% Traditional ROI: 3.15%
2128 Lockard Avenue Chesapeake, VA Step inside this adorable brick ranch and feel right at home! Centrally located in Chesape...	3 beds \| 2 baths \| 1,207 sq.ft.	$310,000	Airbnb cash on cash: 9.77% Traditional cash on cash: 3.96% Airbnb Rental Income: $4377 Traditional Rental Income: $1765 Airbnb ROI: 9.77% Traditional ROI: 3.96%

Real Estate investment in Chesapeake, VA

There are 424 properties for sale in the city of Chesapeake . The median list price in Chesapeake is $439,900 and the average price per square foot is $199. In September 2024, the average monthly cash on cash return in Chesapeake is 4.00%. The average monthly rental income in Chesapeake is $2,431.

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

There are 424 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 $3,179.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake, VA

1792 Cedar Road

Chesapeake, VA

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

$619,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.81%

Airbnb Rental Income: $null

Traditional Rental Income: $2834

Airbnb ROI: N/A

Traditional ROI: 2.81%

1924 ELBOW Road

Chesapeake, VA

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

$340,000

Airbnb cash on cash: 5.94%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $3395

Traditional Rental Income: $2412

Airbnb ROI: 5.94%

Traditional ROI: 5.22%

4176 Williamson Street

Chesapeake, VA

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

$258,900

Airbnb cash on cash: 8.15%

Traditional cash on cash: 6.23%

Airbnb Rental Income: $3149

Traditional Rental Income: $1967

Airbnb ROI: 8.15%

Traditional ROI: 6.23%

4225 Terry Drive

Chesapeake, VA

4 beds | 2 baths | 2,073 sq.ft.

$400,000

Airbnb cash on cash: 5.79%

Traditional cash on cash: 4.01%

Airbnb Rental Income: $3767

Traditional Rental Income: $2283

Airbnb ROI: 5.79%

Traditional ROI: 4.01%

641 Gallbush Road

Chesapeake, VA

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

$519,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.12%

Airbnb Rental Income: $null

Traditional Rental Income: $2385

Airbnb ROI: N/A

Traditional ROI: 3.12%

904 Anna Joy Court

Chesapeake, VA

4 beds | 3 baths | 3,112 sq.ft.

$675,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.47%

Airbnb Rental Income: $null

Traditional Rental Income: $3464

Airbnb ROI: N/A

Traditional ROI: 3.47%

816 Gilchrist Ct

Chesapeake, VA

4 beds | 4 baths | 3,782 sq.ft.

$749,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.15%

Airbnb Rental Income: $null

Traditional Rental Income: $2928

Airbnb ROI: N/A

Traditional ROI: 2.15%

933 Washington Drive

Chesapeake, VA

4 beds | 3 baths | 2,474 sq.ft.

$549,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.26%

Airbnb Rental Income: $null

Traditional Rental Income: $2725

Airbnb ROI: N/A