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
1439 Thistlewood Lane Chesapeake, VA Beautifully maintained and updated Condo in the highly sought after adult active 55+ commu...	2 beds \| 2 baths \| 1,727 sq.ft.	$425,000	Airbnb cash on cash: -2.23% Traditional cash on cash: 2.31% Airbnb Rental Income: $708 Traditional Rental Income: $2208 Airbnb ROI: -2.23% Traditional ROI: 2.31%
4308 Colindale Road #206 Chesapeake, VA Move in ready - Beautiful 2nd floor condo. Walk into an open floor plan with new LVP in th...	2 beds \| 2 baths \| 1,367 sq.ft.	$229,900	Airbnb cash on cash: 2.56% Traditional cash on cash: 6.95% Airbnb Rental Income: $1530 Traditional Rental Income: $2040 Airbnb ROI: 2.56% Traditional ROI: 6.95%
1016 Thoroughgood Way #307 Chesapeake, VA Make this your first stop! Beautifully maintained, low maintenance, open concept, Third fl...	2 beds \| 2 baths \| 1,255 sq.ft.	$247,555	Airbnb cash on cash: -0.18% Traditional cash on cash: 6.32% Airbnb Rental Income: $807 Traditional Rental Income: $2004 Airbnb ROI: -0.18% Traditional ROI: 6.32%
801 Poindexter Street #314 Chesapeake, VA Spacious, move-in ready condo just minutes from Norfolk Naval Base, Portsmouth Shipyard, a...	1 beds \| 1 baths \| 1,135 sq.ft.	$177,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 7.41% Airbnb Rental Income: $900 Traditional Rental Income: $1661 Airbnb ROI: 0.89% Traditional ROI: 7.41%
828 Woodstream Way Chesapeake, VA Welcome to this beautifully maintained home in the sought-after Hickory High School distri...	4 beds \| 3 baths \| 2,785 sq.ft.	$594,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $2971 Airbnb ROI: N/A Traditional ROI: 3.29%
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.	$450,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 4.48% Airbnb Rental Income: $1045 Traditional Rental Income: $2730 Airbnb ROI: -0.38% Traditional ROI: 4.48%
800 Monroe Court Chesapeake, VA Nestled in the heart of Greenbrier, this end-unit condo sits on a tranquil cul-de-sac with...	3 beds \| 3 baths \| 2,225 sq.ft.	$398,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 4.21% Airbnb Rental Income: $1099 Traditional Rental Income: $2385 Airbnb ROI: -0.23% Traditional ROI: 4.21%
5029 Pughsville Road Chesapeake, VA Easy access to all of Hampton Roads with Solar, Fenced Yard, Storage & No HOA! Welcome to ...	3 beds \| 3 baths \| 1,902 sq.ft.	$399,900	Airbnb cash on cash: -0.81% Traditional cash on cash: 4.14% Airbnb Rental Income: $818 Traditional Rental Income: $2349 Airbnb ROI: -0.81% Traditional ROI: 4.14%
1016 Thoroughgood Way #201 Chesapeake, VA Make this your first stop! Beautifully maintained, low maintenance, open concept, second f...	2 beds \| 2 baths \| 1,169 sq.ft.	$239,900	Airbnb cash on cash: -0.16% Traditional cash on cash: 6.08% Airbnb Rental Income: $807 Traditional Rental Income: $1898 Airbnb ROI: -0.16% Traditional ROI: 6.08%
4108 Lakeview Drive Chesapeake, VA Discover the potential of waterfront living at 4108 Lakeview Drive. This spacious home sit...	4 beds \| 3 baths \| 3,169 sq.ft.	$495,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 5.23% Airbnb Rental Income: $1991 Traditional Rental Income: $3291 Airbnb ROI: 1.3% Traditional ROI: 5.23%
508 Rue Saint La Rogue Chesapeake, VA Welcome to 508 Rue Saint La Rogue, Chesapeake! Located in the desirable **Les Chateau...	2 beds \| 3 baths \| 1,158 sq.ft.	$214,990	Airbnb cash on cash: -0.61% Traditional cash on cash: 7.12% Airbnb Rental Income: $677 Traditional Rental Income: $1950 Airbnb ROI: -0.61% Traditional ROI: 7.12%
627 Luray Terrace Chesapeake, VA Discover storybook charm and modern luxury in this Glenwood home on a picturesque corner l...	4 beds \| 4 baths \| 1,973 sq.ft.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.24% Airbnb Rental Income: $null Traditional Rental Income: $2906 Airbnb ROI: N/A Traditional ROI: 4.24%
1303 Tigertail Drive Chesapeake, VA Beautiful 2-bedroom, 2.5-bath condo in a fantastic Chesapeake location! This well-maintain...	2 beds \| 3 baths \| 1,262 sq.ft.	$255,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 5.56% Airbnb Rental Income: $708 Traditional Rental Income: $1904 Airbnb ROI: -0.69% Traditional ROI: 5.56%
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: 0.11% Traditional cash on cash: 4.8% Airbnb Rental Income: $922 Traditional Rental Income: $1866 Airbnb ROI: 0.11% 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.	$385,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 4.61% Airbnb Rental Income: $1045 Traditional Rental Income: $2480 Airbnb ROI: -0.37% Traditional ROI: 4.61%
761 Sherman Drive Chesapeake, VA Check out this beautifully updated brick ranch offering 4 bedrooms and 2 full bathrooms, i...	4 beds \| 2 baths \| 1,714 sq.ft.	$349,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 5.03% Airbnb Rental Income: $1001 Traditional Rental Income: $2345 Airbnb ROI: -0.14% Traditional ROI: 5.03%
1441 Waterlawn Avenue Chesapeake, VA Welcome to this inviting 3-bedroom, 2.5-bath, two-story home nestled in a quiet, friendly ...	3 beds \| 3 baths \| 1,700 sq.ft.	$355,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 4.5% Airbnb Rental Income: $1058 Traditional Rental Income: $2237 Airbnb ROI: -0.13% Traditional ROI: 4.5%
3424 Brandywine Drive Chesapeake, VA Don't miss this beautiful 4-bedroom, 2-bath home in Western Branch school district. Renova...	4 beds \| 2 baths \| 1,276 sq.ft.	$324,900	Airbnb cash on cash: 0.65% Traditional cash on cash: 4.61% Airbnb Rental Income: $1256 Traditional Rental Income: $2067 Airbnb ROI: 0.65% Traditional ROI: 4.61%
3408 Albury Court Chesapeake, VA Welcome to this spacious 4-bedroom, 2.5 bath beauty in a prime Chesapeake location! With o...	4 beds \| 3 baths \| 3,000 sq.ft.	$524,900	Airbnb cash on cash: -0.33% Traditional cash on cash: 4.33% Airbnb Rental Income: $1256 Traditional Rental Income: $3146 Airbnb ROI: -0.33% Traditional ROI: 4.33%
1113 Edinburgh Parkway Chesapeake, VA Welcome Home! Charming and move-in ready, this elegant home offers modern comfort with tim...	4 beds \| 3 baths \| 2,416 sq.ft.	$619,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.82% Airbnb Rental Income: $null Traditional Rental Income: $2869 Airbnb ROI: N/A Traditional ROI: 2.82%
1016 Thoroughgood Way #101 Chesapeake, VA	2 beds \| 2 baths \| 1,166 sq.ft.	$230,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 6.19% Airbnb Rental Income: $807 Traditional Rental Income: $1856 Airbnb ROI: -0.12% Traditional ROI: 6.19%
200 Stubbs Drive Chesapeake, VA Looking for a gorgeous true ranch?! Look no further! This stunner shows like a dream. Upda...	3 beds \| 2 baths \| 1,595 sq.ft.	$399,999	Airbnb cash on cash: -0.23% Traditional cash on cash: 3.63% Airbnb Rental Income: $1058 Traditional Rental Income: $2139 Airbnb ROI: -0.23% Traditional ROI: 3.63%
1423 Otterbourne Circle Chesapeake, VA Beautifully maintained condo in the heart of Greenbrier! Thoughtfully updated, featuring a...	3 beds \| 3 baths \| 1,881 sq.ft.	$389,900	Airbnb cash on cash: -0.16% Traditional cash on cash: 5.13% Airbnb Rental Income: $1099 Traditional Rental Income: $2662 Airbnb ROI: -0.16% Traditional ROI: 5.13%
709 Phalarope Street Chesapeake, VA Welcome to this beautiful home in sought-after Culpepper Landing! Featuring elegant Torino...	4 beds \| 3 baths \| 3,662 sq.ft.	$575,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 3% Airbnb Rental Income: $1304 Traditional Rental Income: $2872 Airbnb ROI: -0.68% Traditional ROI: 3%
933 Saddleback Trail Road Chesapeake, VA Welcome to this stellar 4-bedroom, 2-bath ranch in the heart of Chesapeake, offering 1,830...	4 beds \| 2 baths \| 1,830 sq.ft.	$495,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 3.19% Airbnb Rental Income: $1113 Traditional Rental Income: $2404 Airbnb ROI: -0.4% Traditional ROI: 3.19%
4195 Taughtline Loop Chesapeake, VA Welcome to this beautiful 3-bedroom, 2.5-bath condo in Goose Creek Estates, located in the...	3 beds \| 3 baths \| 2,062 sq.ft.	$364,900	Airbnb cash on cash: -1.18% Traditional cash on cash: 4.51% Airbnb Rental Income: $911 Traditional Rental Income: $2517 Airbnb ROI: -1.18% Traditional ROI: 4.51%
232 Hickory Road E Chesapeake, VA This beautifully maintained home in the highly desired Hickory School District features an...	4 beds \| 3 baths \| 2,225 sq.ft.	$539,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.1% Airbnb Rental Income: $null Traditional Rental Income: $2621 Airbnb ROI: N/A Traditional ROI: 3.1%
509 Saber Drive Chesapeake, VA Absolutely stunning 4-bedroom, 2-full-bath home located in the highly sought-after Wilson ...	4 beds \| 2 baths \| 2,213 sq.ft.	$530,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 2.97% Airbnb Rental Income: $1113 Traditional Rental Income: $2491 Airbnb ROI: -0.57% Traditional ROI: 2.97%
1821 Volvo Parkway Chesapeake, VA Welcome to this beautiful lakeside townhome in the heart of Greenbrier! With a low-mainten...	2 beds \| 3 baths \| 1,341 sq.ft.	$309,876	Airbnb cash on cash: -1% Traditional cash on cash: 4.29% Airbnb Rental Income: $708 Traditional Rental Income: $1944 Airbnb ROI: -1% Traditional ROI: 4.29%
212 George Washington Highway N Chesapeake, VA EXTREMELY MOTIVATED. Welcome to this charming 3-bedroom, 2-bath Cape Cod filled with chara...	3 beds \| 2 baths \| 1,875 sq.ft.	$324,900	Airbnb cash on cash: -0.74% Traditional cash on cash: 5.13% Airbnb Rental Income: $824 Traditional Rental Income: $2290 Airbnb ROI: -0.74% Traditional ROI: 5.13%
214 Douglas Avenue Chesapeake, VA Welcome home to this beautifully updated 3-bedroom, 2.5-bath property in Chesapeake, VA. S...	3 beds \| 3 baths \| 1,628 sq.ft.	$365,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 4.37% Airbnb Rental Income: $824 Traditional Rental Income: $2224 Airbnb ROI: -0.67% Traditional ROI: 4.37%
4413 Sunray Avenue Chesapeake, VA A little bit of country in the middle of it all! Welcome home to this nicely maintained ra...	3 beds \| 2 baths \| 1,577 sq.ft.	$325,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 5.04% Airbnb Rental Income: $911 Traditional Rental Income: $2214 Airbnb ROI: -0.34% Traditional ROI: 5.04%
911 Mount Pleasant Road Chesapeake, VA Bright open floor plan with cathedral ceilings in the family room which opens to the kitch...	4 beds \| 3 baths \| 2,180 sq.ft.	$469,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $2714 Airbnb ROI: N/A Traditional ROI: 4.12%
1420 Anne Avenue Chesapeake, VA Welcome to this well-maintained 4-bedroom home in a prime Chesapeake location, offering qu...	4 beds \| 1 baths \| 1,200 sq.ft.	$309,900	Airbnb cash on cash: -0.72% Traditional cash on cash: 3.46% Airbnb Rental Income: $751 Traditional Rental Income: $1656 Airbnb ROI: -0.72% Traditional ROI: 3.46%
605 Sail Fish Quay Chesapeake, VA Beautiful condo located in Riverwalk! Spacious 3-bedroom, 3-full bath with luxury vinyl fl...	3 beds \| 3 baths \| 1,776 sq.ft.	$226,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 7.45% Airbnb Rental Income: $1039 Traditional Rental Income: $2218 Airbnb ROI: 0.25% Traditional ROI: 7.45%
708 Stalham Road Chesapeake, VA Renovated Ranch! Newly installed Plumbing, Electrical, Zoned Heat/A/C, Roof, Vinyl Siding,...	3 beds \| 1 baths \| 1,309 sq.ft.	$275,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 4.83% Airbnb Rental Income: $922 Traditional Rental Income: $1792 Airbnb ROI: 0.16% Traditional ROI: 4.83%
4026 River Breeze Circle Chesapeake, VA Step inside this beautifully maintained and updated home featuring a bright, open floor pl...	4 beds \| 3 baths \| 1,915 sq.ft.	$349,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 5.56% Airbnb Rental Income: $1991 Traditional Rental Income: $2531 Airbnb ROI: 2.33% Traditional ROI: 5.56%
2114 Mclain Street Chesapeake, VA This beautifully renovated ranch in Avalon blends classic charm with modern updatesâoffe...	3 beds \| 2 baths \| 1,196 sq.ft.	$275,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 5.74% Airbnb Rental Income: $973 Traditional Rental Income: $2059 Airbnb ROI: 0.2% Traditional ROI: 5.74%
3018 Guenevere Drive Chesapeake, VA Beautiful colonial 4 bedroom, 2.5 bath home with lots of sunlight and bountiful upgrades. ...	4 beds \| 3 baths \| 2,000 sq.ft.	$388,500	Airbnb cash on cash: 1.03% Traditional cash on cash: 5.17% Airbnb Rental Income: $1614 Traditional Rental Income: $2665 Airbnb ROI: 1.03% Traditional ROI: 5.17%
1639 Mount Pleasant Road Chesapeake, VA This home was designed for both connection and comfort. From the inviting foyer, youâll ...	4 beds \| 3 baths \| 2,404 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.74% Airbnb Rental Income: $null Traditional Rental Income: $2671 Airbnb ROI: N/A Traditional ROI: 2.74%

Real Estate investment in Chesapeake, VA

There are 440 properties for sale in the city of Chesapeake . The median list price in Chesapeake is $440,000 and the average price per square foot is $205. In December 2025, the average monthly cash on cash return in Chesapeake is 4.00%. The average monthly rental income in Chesapeake is $2,530.

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

There are 440 investment properties available for sale in Chesapeake.

In 2025, 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 $1,039.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake, VA

1439 Thistlewood Lane

Chesapeake, VA

2 beds | 2 baths | 1,727 sq.ft.

$425,000

Airbnb cash on cash: -2.23%

Traditional cash on cash: 2.31%

Airbnb Rental Income: $708

Traditional Rental Income: $2208

Airbnb ROI: -2.23%

Traditional ROI: 2.31%

4308 Colindale Road #206

Chesapeake, VA

2 beds | 2 baths | 1,367 sq.ft.

$229,900

Airbnb cash on cash: 2.56%

Traditional cash on cash: 6.95%

Airbnb Rental Income: $1530

Traditional Rental Income: $2040

Airbnb ROI: 2.56%

Traditional ROI: 6.95%

1016 Thoroughgood Way #307

Chesapeake, VA

2 beds | 2 baths | 1,255 sq.ft.

$247,555

Airbnb cash on cash: -0.18%

Traditional cash on cash: 6.32%

Airbnb Rental Income: $807

Traditional Rental Income: $2004

Airbnb ROI: -0.18%

Traditional ROI: 6.32%

801 Poindexter Street #314

Chesapeake, VA

1 beds | 1 baths | 1,135 sq.ft.

$177,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 7.41%

Airbnb Rental Income: $900

Traditional Rental Income: $1661

Airbnb ROI: 0.89%

Traditional ROI: 7.41%

828 Woodstream Way

Chesapeake, VA

4 beds | 3 baths | 2,785 sq.ft.

$594,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.29%

Airbnb Rental Income: $null

Traditional Rental Income: $2971

Airbnb ROI: N/A

Traditional ROI: 3.29%

2218 Vicker Avenue

Chesapeake, VA

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

$450,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 4.48%

Airbnb Rental Income: $1045

Traditional Rental Income: $2730

Airbnb ROI: -0.38%

Traditional ROI: 4.48%

800 Monroe Court

Chesapeake, VA

3 beds | 3 baths | 2,225 sq.ft.

$398,000

Airbnb cash on cash: -0.23%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $1099

Traditional Rental Income: $2385

Airbnb ROI: -0.23%

Traditional ROI: 4.21%

5029 Pughsville Road

Chesapeake, VA

3 beds | 3 baths | 1,902 sq.ft.

$399,900

Airbnb cash on cash: -0.81%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $818

Traditional Rental Income: $2349

Airbnb ROI: -0.81%