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%
641 Gallbush Road Chesapeake, VA Come View your new home in HICKORY! Spacious 4 bedroom 2 1/2 baths. Open floor plan featur...	4 beds \| 3 baths \| 2,200 sq.ft.	$534,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.7% Airbnb Rental Income: $null Traditional Rental Income: $2385 Airbnb ROI: N/A Traditional ROI: 2.7%
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! Beautiful Balcony Views. Well maintained, low maintenance, open...	2 beds \| 2 baths \| 1,255 sq.ft.	$245,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 6.4% Airbnb Rental Income: $807 Traditional Rental Income: $2004 Airbnb ROI: -0.17% Traditional ROI: 6.4%
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%
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%
4311 Salt Marsh Lane Chesapeake, VA This 4-bedroom, 3.5-bath, 3 story townhome offering approximately 2,000 sqft is one of, if...	4 beds \| 4 baths \| 2,000 sq.ft.	$350,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 6.12% Airbnb Rental Income: $751 Traditional Rental Income: $2737 Airbnb ROI: -0.88% Traditional ROI: 6.12%
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%
14 Keswick Circle Chesapeake, VA Welcome to this charming End Unit Townhome in Ipswich. This 3-bedroom, 2.5-bath townhome ...	3 beds \| 3 baths \| 1,428 sq.ft.	$300,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 4.29% Airbnb Rental Income: $922 Traditional Rental Income: $1878 Airbnb ROI: -0.3% Traditional ROI: 4.29%
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%
1825 Carrera Ridge Chesapeake, VA Enter into a 5-bedroom paradise where luxury and comfort blend seamlessly. Every inch of t...	5 beds \| 4 baths \| 2,710 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.06% Airbnb Rental Income: $null Traditional Rental Income: $3193 Airbnb ROI: N/A Traditional ROI: 3.06%
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%
3932 Pierce Lane Chesapeake, VA	2 beds \| 2 baths \| 1,176 sq.ft.	$295,000	Airbnb cash on cash: -1.41% Traditional cash on cash: 3.33% Airbnb Rental Income: $496 Traditional Rental Income: $1541 Airbnb ROI: -1.41% Traditional ROI: 3.33%
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%
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 This is the kind of home families grow into. Set on a quiet Western Branch cul-de-sac, thi...	4 beds \| 3 baths \| 3,400 sq.ft.	$515,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 4.43% Airbnb Rental Income: $1256 Traditional Rental Income: $3146 Airbnb ROI: -0.32% Traditional ROI: 4.43%
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%
745 Lacy Oak Drive Chesapeake, VA Back on market at no fault of the seller. Home inspection and appraisal were completed, an...	2 beds \| 3 baths \| 1,870 sq.ft.	$320,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 5.44% Airbnb Rental Income: $677 Traditional Rental Income: $2317 Airbnb ROI: -1.01% Traditional ROI: 5.44%
913 Annette Street Chesapeake, VA Centrally located when charm meets convenience. Newly remolded. The open kitchen/dining/...	3 beds \| 3 baths \| 1,422 sq.ft.	$315,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 4.89% Airbnb Rental Income: $922 Traditional Rental Income: $1969 Airbnb ROI: 0.2% Traditional ROI: 4.89%
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.	$480,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 3.32% Airbnb Rental Income: $1425 Traditional Rental Income: $2404 Airbnb ROI: 0.19% Traditional ROI: 3.32%
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.	$534,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.13% Airbnb Rental Income: $null Traditional Rental Income: $2621 Airbnb ROI: N/A Traditional ROI: 3.13%
1402 Shortleaf Lane Chesapeake, VA Welcome home to this spacious 2BR, 2.5BA two-story condo in the heart of Greenbrier! The f...	2 beds \| 3 baths \| 1,251 sq.ft.	$255,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 5.22% Airbnb Rental Income: $708 Traditional Rental Income: $1813 Airbnb ROI: -0.65% Traditional ROI: 5.22%
2114 Mclain Street Chesapeake, VA Welcome to this charming, modern 3 bedroom, 1.5 bath ranch style home nestled in the sough...	3 beds \| 2 baths \| 1,196 sq.ft.	$229,900	Airbnb cash on cash: 0.39% Traditional cash on cash: 7% Airbnb Rental Income: $973 Traditional Rental Income: $2059 Airbnb ROI: 0.39% Traditional ROI: 7%
409 Faire Chase Chesapeake, VA Move-in ready Great Bridge townhouse located in the heart of Great Bridge and near shoppin...	2 beds \| 3 baths \| 1,341 sq.ft.	$299,900	Airbnb cash on cash: -1.04% Traditional cash on cash: 4.51% Airbnb Rental Income: $643 Traditional Rental Income: $1912 Airbnb ROI: -1.04% Traditional ROI: 4.51%
1100 Walnut Neck Avenue Chesapeake, VA You will love coming home to 1100 Walnut Neck Ave! A versatile flex space welcomes you at ...	4 beds \| 3 baths \| 2,543 sq.ft.	$584,990	Airbnb cash on cash: -0.67% Traditional cash on cash: 2.82% Airbnb Rental Income: $1288 Traditional Rental Income: $2789 Airbnb ROI: -0.67% Traditional ROI: 2.82%
3009 Patrick Henry Drive Chesapeake, VA Welcome to this beautiful 5-bedroom, 2.5-bath home located in the highly sought-after Culp...	5 beds \| 3 baths \| 3,228 sq.ft.	$584,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.7% Airbnb Rental Income: $null Traditional Rental Income: $2734 Airbnb ROI: N/A Traditional ROI: 2.7%
229 Vanette DR Chesapeake, VA This brick ranch offers a flexible and unique layout. With designer touches like exposed b...	4 beds \| 3 baths \| N/A	$515,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 4.37% Airbnb Rental Income: $1425 Traditional Rental Income: $3081 Airbnb ROI: 0.05% Traditional ROI: 4.37%
1144 Whitburn Terrace Chesapeake, VA Welcome home... Freshly painted and move-in-ready, this Brandon plan is waiting for you. P...	3 beds \| 2 baths \| 2,149 sq.ft.	$429,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 3.42% Airbnb Rental Income: $903 Traditional Rental Income: $2250 Airbnb ROI: -0.78% Traditional ROI: 3.42%
1462 Titchfield Drive Chesapeake, VA Discover a blend of comfort and convenience in this beautifully maintained 2-bedroom, 2.5-...	2 beds \| 3 baths \| 1,350 sq.ft.	$283,999	Airbnb cash on cash: -0.72% Traditional cash on cash: 5.35% Airbnb Rental Income: $708 Traditional Rental Income: $2027 Airbnb ROI: -0.72% Traditional ROI: 5.35%
1217 Cleona Drive Chesapeake, VA Charming 3-bed, 1-bath ranch in Chesapeakeâs Indian River neighborhood at 1217 Cleona Dr...	3 beds \| 1 baths \| 1,014 sq.ft.	$255,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 5.06% Airbnb Rental Income: $922 Traditional Rental Income: $1763 Airbnb ROI: 0.14% Traditional ROI: 5.06%
4109 Franklin Street Chesapeake, VA Welcome to this sweet three bedroom, 2.5 bath home. You'll love how the kitchen opens to t...	3 beds \| 3 baths \| 1,500 sq.ft.	$335,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 4.72% Airbnb Rental Income: $973 Traditional Rental Income: $2177 Airbnb ROI: -0.22% Traditional ROI: 4.72%
4217 Wake Ave Chesapeake, VA Beautifully Updated 4-Bedroom Home with Huge Backyard in Chesapeake! Welcome to 4217 Wake ...	4 beds \| 2 baths \| 1,237 sq.ft.	$349,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 4.47% Airbnb Rental Income: $751 Traditional Rental Income: $2086 Airbnb ROI: -0.56% Traditional ROI: 4.47%
1416 Wingfield Avenue Chesapeake, VA Centrally located Chesapeake ranch situated on a spacious, fully fenced lot, featuring an ...	4 beds \| 2 baths \| 1,210 sq.ft.	$350,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 4.09% Airbnb Rental Income: $1045 Traditional Rental Income: $2034 Airbnb ROI: -0.02% Traditional ROI: 4.09%
2309 Drum Creek Road Chesapeake, VA Beautiful Renovated Brick Ranch on a quiet street! Shows like a model, this 3 bedroom 2 ba...	3 beds \| 2 baths \| 1,771 sq.ft.	$429,900	Airbnb cash on cash: -0.71% Traditional cash on cash: 3.39% Airbnb Rental Income: $818 Traditional Rental Income: $2145 Airbnb ROI: -0.71% Traditional ROI: 3.39%
2517 Quail Ridge Court Chesapeake, VA Step into this beautifully cared for brick ranch and feel right at home. With four spaciou...	4 beds \| 2 baths \| 1,804 sq.ft.	$395,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 4.16% Airbnb Rental Income: $1256 Traditional Rental Income: $2343 Airbnb ROI: 0.15% Traditional ROI: 4.16%
538 Hadleybrook Drive Chesapeake, VA Move-in ready corner unit sought-after Greenbrier! Stylish light fixtures, abundant natura...	2 beds \| 3 baths \| 1,352 sq.ft.	$280,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 5.16% Airbnb Rental Income: $677 Traditional Rental Income: $1968 Airbnb ROI: -0.88% Traditional ROI: 5.16%
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.	$299,900	Airbnb cash on cash: 0.01% Traditional cash on cash: 5.5% Airbnb Rental Income: $973 Traditional Rental Income: $2171 Airbnb ROI: 0.01% Traditional ROI: 5.5%
929 Stanhope Gardens Chesapeake, VA Welcome to 929 Stanhope Gardensâan elegant 3-bedroom (loft can be converted as the 3rd b...	3 beds \| 3 baths \| 2,100 sq.ft.	$395,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.18% Airbnb Rental Income: $1039 Traditional Rental Income: $2418 Airbnb ROI: -0.52% Traditional ROI: 4.18%
3616 Parr Ln Chesapeake, VA	3 beds \| 2 baths \| 1,534 sq.ft.	$314,900	Airbnb cash on cash: -0.7% Traditional cash on cash: 4.26% Airbnb Rental Income: $824 Traditional Rental Income: $1967 Airbnb ROI: -0.7% Traditional ROI: 4.26%

Real Estate investment in Chesapeake, VA

There are 337 properties for sale in the city of Chesapeake . The median list price in Chesapeake is $439,000 and the average price per square foot is $208. In February 2026, the average monthly cash on cash return in Chesapeake is 4.00%. The average monthly rental income in Chesapeake is $2,488.

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

There are 337 investment properties available for sale in Chesapeake.

In 2026, the best neighborhood to buy investment property is South Norfolk.

The ROI for Short-Term is higher than the Long-Term in Chesapeake with average rental income of $1,001.

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%

641 Gallbush Road

Chesapeake, VA

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

$534,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.7%

Airbnb Rental Income: $null

Traditional Rental Income: $2385

Airbnb ROI: N/A

Traditional ROI: 2.7%

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.

$245,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 6.4%

Airbnb Rental Income: $807

Traditional Rental Income: $2004

Airbnb ROI: -0.17%

Traditional ROI: 6.4%

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%

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%

4311 Salt Marsh Lane

Chesapeake, VA

4 beds | 4 baths | 2,000 sq.ft.

$350,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: 6.12%

Airbnb Rental Income: $751

Traditional Rental Income: $2737

Airbnb ROI: -0.88%

Traditional ROI: 6.12%

1016 Thoroughgood Way #201

Chesapeake, VA

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%