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
1222 Jackson Avenue Chesapeake, VA Welcome to 1222 Jackson Ave. This home is located in Historic Chesapeake and offers the pe...	3 beds \| 2 baths \| 1,894 sq.ft.	$320,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 5.15% Airbnb Rental Income: $1450 Traditional Rental Income: $2217 Airbnb ROI: 1.17% Traditional ROI: 5.15%
1813 Sunsprite Loop Chesapeake, VA This Beautiful 4 bedroom 2 1/2 bath traditional style home located in the Landing at Grass...	4 beds \| 3 baths \| 2,446 sq.ft.	$599,999	Airbnb cash on cash: -0.2% Traditional cash on cash: 2.55% Airbnb Rental Income: $1614 Traditional Rental Income: $2693 Airbnb ROI: -0.2% Traditional ROI: 2.55%
1002 Whitburn Terrace #373 Chesapeake, VA Energy-efficient single-family home on a premium cul-de-sac lot with scenic views! Located...	3 beds \| 3 baths \| 2,159 sq.ft.	$545,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 3.42% Airbnb Rental Income: $1214 Traditional Rental Income: $2790 Airbnb ROI: -0.44% Traditional ROI: 3.42%
812 Hardwood Drive Chesapeake, VA Welcome to this beautifully maintained 4-bedroom, 3 full bath ranch in the highly desirabl...	4 beds \| 3 baths \| 1,921 sq.ft.	$440,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 3.94% Airbnb Rental Income: $2199 Traditional Rental Income: $2573 Airbnb ROI: 1.68% Traditional ROI: 3.94%
627 Emerald Court Chesapeake, VA Motivated seller-bring your buyers! This 4-bedroom, 3 full bath home is ideally located in...	4 beds \| 3 baths \| 2,887 sq.ft.	$550,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 4.07% Airbnb Rental Income: $2199 Traditional Rental Income: $3176 Airbnb ROI: 1.09% Traditional ROI: 4.07%
1125 Sutherlyn Court Chesapeake, VA This stunning all-brick home sits at the end of a quiet cul-de-sac on a beautifully mainta...	4 beds \| 3 baths \| 3,000 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.01% Airbnb Rental Income: $null Traditional Rental Income: $2655 Airbnb ROI: N/A Traditional ROI: 2.01%
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.	$520,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.8% Airbnb Rental Income: $null Traditional Rental Income: $2385 Airbnb ROI: N/A Traditional ROI: 2.8%
1114 Hoover Avenue Chesapeake, VA Welcome home! This inviting property features a spacious layout with plenty of room to spr...	3 beds \| 2 baths \| 1,332 sq.ft.	$290,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 4.44% Airbnb Rental Income: $1450 Traditional Rental Income: $1790 Airbnb ROI: 1.62% Traditional ROI: 4.44%
2809 Halsey Street Chesapeake, VA Welcome to this beautifully renovated 3-bedroom, 2-bathroom gem in the heart of Chesapeake...	3 beds \| 2 baths \| 1,352 sq.ft.	$320,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 4.28% Airbnb Rental Income: $1450 Traditional Rental Income: $1914 Airbnb ROI: 1.31% Traditional ROI: 4.28%
1000 York Drive Chesapeake, VA Here is the cutest 4-bedroom ranch you'll find in Greenbrier, tucked on a quiet cul-de-sac...	4 beds \| 3 baths \| 1,682 sq.ft.	$440,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 3.78% Airbnb Rental Income: $2199 Traditional Rental Income: $2400 Airbnb ROI: 1.95% Traditional ROI: 3.78%
426 San Roman Drive Chesapeake, VA Discover this stunning, renovated townhouse in the sought-after Las Gaviotas community, 1,...	3 beds \| 3 baths \| 1,540 sq.ft.	$359,900	Airbnb cash on cash: 0.23% Traditional cash on cash: 4.77% Airbnb Rental Income: $1214 Traditional Rental Income: $2357 Airbnb ROI: 0.23% Traditional ROI: 4.77%
1016 Thoroughgood Way #307 Chesapeake, VA Beautifully maintained, one-owner, 3rd-floor condo with elevator access in a secure-entry ...	2 beds \| 2 baths \| 1,255 sq.ft.	$245,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 6.28% Airbnb Rental Income: $828 Traditional Rental Income: $2004 Airbnb ROI: -0.21% Traditional ROI: 6.28%
2712 Mark Street Chesapeake, VA Charming ranch-style home offering one-level living! The kitchen flows into the family roo...	4 beds \| 2 baths \| 1,550 sq.ft.	$315,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 5.39% Airbnb Rental Income: $1138 Traditional Rental Income: $2263 Airbnb ROI: 0.32% Traditional ROI: 5.39%
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.	$159,900	Airbnb cash on cash: 1.74% Traditional cash on cash: 8.28% Airbnb Rental Income: $1020 Traditional Rental Income: $1661 Airbnb ROI: 1.74% Traditional ROI: 8.28%
331 Appaloosa Trail Chesapeake, VA Welcome home to a home where comfort, style, and space come together beautifully! This cha...	4 beds \| 3 baths \| 2,148 sq.ft.	$484,999	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.85% Airbnb Rental Income: $1614 Traditional Rental Income: $2673 Airbnb ROI: 0.5% Traditional ROI: 3.85%
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.	$440,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 4.61% Airbnb Rental Income: $1825 Traditional Rental Income: $2730 Airbnb ROI: 1.21% Traditional ROI: 4.61%
317 Wimbledon Chase #F Chesapeake, VA Welcome to this beautiful 2BR/2BA well maintained and updated second story condo in the hi...	2 beds \| 2 baths \| 962 sq.ft.	$210,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 5.79% Airbnb Rental Income: $960 Traditional Rental Income: $1619 Airbnb ROI: 0.73% Traditional ROI: 5.79%
3313 Dodd Drive Chesapeake, VA Welcome Home! Step into this stunning home featuring soaring ceilings and a chef inspired ...	4 beds \| 3 baths \| 2,862 sq.ft.	$550,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 3.9% Airbnb Rental Income: $1614 Traditional Rental Income: $3014 Airbnb ROI: 0.28% Traditional ROI: 3.9%
1333 Great Bridge Boulevard Chesapeake, VA Welcome to Crestwood Gardens in Chesapeake! This home features major updates made within t...	3 beds \| 2 baths \| 1,317 sq.ft.	$279,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 6.14% Airbnb Rental Income: $1360 Traditional Rental Income: $2226 Airbnb ROI: 1.27% Traditional ROI: 6.14%
1108 Anne Avenue Chesapeake, VA Cute ranch home in Southern Chesapeake with new paint thought out. Incredible backyard for...	3 beds \| 1 baths \| 900 sq.ft.	$285,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 4.27% Airbnb Rental Income: $1450 Traditional Rental Income: $1736 Airbnb ROI: 1.6% Traditional ROI: 4.27%
1428 Winslow Avenue Chesapeake, VA Welcome to this spacious 4-bedroom, 2-bath home offering one of the largest floor plans in...	4 beds \| 2 baths \| 2,172 sq.ft.	$390,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.62% Airbnb Rental Income: $null Traditional Rental Income: $2477 Airbnb ROI: N/A Traditional ROI: 4.62%
3615 Cinnamon Court Chesapeake, VA Beautiful condo located in the highly sought-after Miars Farms area and within a desirable...	3 beds \| 3 baths \| 1,554 sq.ft.	$270,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 5.52% Airbnb Rental Income: $1178 Traditional Rental Income: $1962 Airbnb ROI: 0.93% Traditional ROI: 5.52%
340 Middle Oaks Drive Chesapeake, VA 340 Middle Oaks Drive offers a functional layout and move-in ready condition in the desira...	2 beds \| 3 baths \| 1,238 sq.ft.	$290,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 3.88% Airbnb Rental Income: $761 Traditional Rental Income: $1678 Airbnb ROI: -0.64% Traditional ROI: 3.88%
2417 Baum Road Chesapeake, VA Comfort, luxury and space come together in this move-in-ready home. Vaulted ceilings and f...	4 beds \| 4 baths \| 3,985 sq.ft.	$959,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.73% Airbnb Rental Income: $null Traditional Rental Income: $3393 Airbnb ROI: N/A Traditional ROI: 1.73%
221 Cedar Creek Terrace Chesapeake, VA This Great bridge, move in ready, end-unit townhouse home has a large, fenced yard and on ...	2 beds \| 3 baths \| 1,304 sq.ft.	$299,465	Airbnb cash on cash: -0.66% Traditional cash on cash: 3.96% Airbnb Rental Income: $761 Traditional Rental Income: $1746 Airbnb ROI: -0.66% Traditional ROI: 3.96%
4162 Reid Street Chesapeake, VA This adorable ranch home is move-in ready and has been professionally renovated from top t...	3 beds \| 2 baths \| 1,330 sq.ft.	$305,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 4.6% Airbnb Rental Income: $1450 Traditional Rental Income: $1937 Airbnb ROI: 1.41% Traditional ROI: 4.6%
3320 Daystone Arch Chesapeake, VA Welcome to 3320 Daystone Arch! Stunning 5 bedroom 2.5 bath nestled on a quiet street in th...	5 beds \| 3 baths \| 3,400 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $2988 Airbnb ROI: N/A Traditional ROI: 3.3%
1002 Midway Drive Chesapeake, VA Welcome to 1002 Midway Drive-a rare nearly half-acre find in the sought-after Grassfield H...	4 beds \| 3 baths \| 2,654 sq.ft.	$565,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.68% Airbnb Rental Income: $null Traditional Rental Income: $3074 Airbnb ROI: N/A Traditional ROI: 3.68%
4332 Hillingdon Bend #104 Chesapeake, VA Discover this BEAUTIFUL 2-bedroom home in the sought-after Western Branch area! This gem f...	2 beds \| 2 baths \| 1,367 sq.ft.	$232,700	Airbnb cash on cash: 0.89% Traditional cash on cash: 6.62% Airbnb Rental Income: $1092 Traditional Rental Income: $1982 Airbnb ROI: 0.89% Traditional ROI: 6.62%
4311 Emporia Court Chesapeake, VA Welcome to this beautifully maintained home situated on a quiet cul-de-sac in Chesapeake. ...	3 beds \| 1 baths \| 1,320 sq.ft.	$315,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 3.64% Airbnb Rental Income: $980 Traditional Rental Income: $1741 Airbnb ROI: -0.12% Traditional ROI: 3.64%
1004 Wymers Court Chesapeake, VA Spacious 5-bedroom ranch with finished room over the garage offers a unique natural settin...	5 beds \| 2 baths \| 2,073 sq.ft.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.86% Airbnb Rental Income: $null Traditional Rental Income: $2761 Airbnb ROI: N/A Traditional ROI: 3.86%
1972 Beechwood Road Chesapeake, VA This charming four-bedroom Stephen Alexander Walnut model in the desirable Summer Park com...	4 beds \| 3 baths \| 3,114 sq.ft.	$689,900	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.83% Airbnb Rental Income: $1614 Traditional Rental Income: $3186 Airbnb ROI: -0.33% Traditional ROI: 2.83%
4000 Hamilton Street Chesapeake, VA This stunning 3-bed, 2-bath single-family home was completely transformed in 2023 - new ro...	3 beds \| 2 baths \| 1,235 sq.ft.	$335,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 3.4% Airbnb Rental Income: $1450 Traditional Rental Income: $1722 Airbnb ROI: 1.17% Traditional ROI: 3.4%
2432 Lakewood Lane Chesapeake, VA Beautifully updated and maintained brick ranch in highly desirable neighborhood. You will ...	4 beds \| 2 baths \| 1,887 sq.ft.	$420,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 4.02% Airbnb Rental Income: $2026 Traditional Rental Income: $2405 Airbnb ROI: 1.72% Traditional ROI: 4.02%
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: 0.29% Traditional cash on cash: 4.8% Airbnb Rental Income: $980 Traditional Rental Income: $1866 Airbnb ROI: 0.29% Traditional ROI: 4.8%
1310 Elder Avenue Chesapeake, VA This centrally located 3 bedroom 1 bathroom ranch style home is ready for you! Fresh paint...	3 beds \| 1 baths \| 1,140 sq.ft.	$275,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 4.7% Airbnb Rental Income: $980 Traditional Rental Income: $1800 Airbnb ROI: 0.18% Traditional ROI: 4.7%
1008 Fairway Drive Chesapeake, VA Spectacular custom brick home located on the 14th tee of the Greenbrier County Club golf c...	4 beds \| 4 baths \| 3,167 sq.ft.	$670,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 3.09% Airbnb Rental Income: $2199 Traditional Rental Income: $3203 Airbnb ROI: 0.59% Traditional ROI: 3.09%
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.	$300,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 6.17% Airbnb Rental Income: $1825 Traditional Rental Income: $2480 Airbnb ROI: 2.1% Traditional ROI: 6.17%
3920 South Road Chesapeake, VA Meticulously cared for brick ranch. Recently replaced heating and cooling. Central vacuum....	3 beds \| 1 baths \| 1,204 sq.ft.	$350,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 2.89% Airbnb Rental Income: $1186 Traditional Rental Income: $1685 Airbnb ROI: 0.2% Traditional ROI: 2.89%
2041 Lockard Avenue Chesapeake, VA Great investment opportunity! This 3 bedroom, 1 bath ranch comes with a tenant in place th...	3 beds \| 1 baths \| 1,000 sq.ft.	$230,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 5.29% Airbnb Rental Income: $980 Traditional Rental Income: $1675 Airbnb ROI: 0.48% Traditional ROI: 5.29%

Real Estate investment in Chesapeake, VA

There are 491 properties for sale in the city of Chesapeake . The median list price in Chesapeake is $470,000 and the average price per square foot is $206. In May 2026, the average monthly cash on cash return in Chesapeake is 4.00%. The average monthly rental income in Chesapeake is $2,624.

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

There are 491 investment properties available for sale in Chesapeake.

In 2026, the best neighborhood to buy investment property is Indian River.

The ROI for Long-Term is higher than the Short-Term in Chesapeake with average rental income of $2,624.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake, VA

1222 Jackson Avenue

Chesapeake, VA

3 beds | 2 baths | 1,894 sq.ft.

$320,000

Airbnb cash on cash: 1.17%

Traditional cash on cash: 5.15%

Airbnb Rental Income: $1450

Traditional Rental Income: $2217

Airbnb ROI: 1.17%

Traditional ROI: 5.15%

1813 Sunsprite Loop

Chesapeake, VA

4 beds | 3 baths | 2,446 sq.ft.

$599,999

Airbnb cash on cash: -0.2%

Traditional cash on cash: 2.55%

Airbnb Rental Income: $1614

Traditional Rental Income: $2693

Airbnb ROI: -0.2%

Traditional ROI: 2.55%

1002 Whitburn Terrace #373

Chesapeake, VA

3 beds | 3 baths | 2,159 sq.ft.

$545,000

Airbnb cash on cash: -0.44%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $1214

Traditional Rental Income: $2790

Airbnb ROI: -0.44%

Traditional ROI: 3.42%

812 Hardwood Drive

Chesapeake, VA

4 beds | 3 baths | 1,921 sq.ft.

$440,000

Airbnb cash on cash: 1.68%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $2199

Traditional Rental Income: $2573

Airbnb ROI: 1.68%

Traditional ROI: 3.94%

627 Emerald Court

Chesapeake, VA

4 beds | 3 baths | 2,887 sq.ft.

$550,000

Airbnb cash on cash: 1.09%

Traditional cash on cash: 4.07%

Airbnb Rental Income: $2199

Traditional Rental Income: $3176

Airbnb ROI: 1.09%

Traditional ROI: 4.07%

1125 Sutherlyn Court

Chesapeake, VA

4 beds | 3 baths | 3,000 sq.ft.

$695,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.01%

Airbnb Rental Income: $null

Traditional Rental Income: $2655

Airbnb ROI: N/A

Traditional ROI: 2.01%

641 Gallbush Road

Chesapeake, VA

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

$520,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.8%

Airbnb Rental Income: $null

Traditional Rental Income: $2385

Airbnb ROI: N/A

Traditional ROI: 2.8%

1114 Hoover Avenue

Chesapeake, VA

3 beds | 2 baths | 1,332 sq.ft.

$290,000

Airbnb cash on cash: 1.62%

Traditional cash on cash: 4.44%

Airbnb Rental Income: $1450

Traditional Rental Income: $1790

Airbnb ROI: 1.62%