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
2929 Hilton Avenue Chesapeake, VA Spacious 4-bed, 2-bath ranch with generously sized bedrooms; including a large primary sui...	4 beds \| 2 baths \| 1,747 sq.ft.	$310,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 5.87% Airbnb Rental Income: $2405 Traditional Rental Income: $2358 Airbnb ROI: 4.01% Traditional ROI: 5.87%
1408 Ashton Street Chesapeake, VA This updated 4-bed, 3-bath Chesapeake home features new laminate and carpet flooring throu...	4 beds \| 3 baths \| 1,900 sq.ft.	$379,900	Airbnb cash on cash: 5.13% Traditional cash on cash: 5.04% Airbnb Rental Income: $3312 Traditional Rental Income: $2539 Airbnb ROI: 5.13% Traditional ROI: 5.04%
929 Seabreeze Court Chesapeake, VA Stunning townhome in the sought after Greenbrier area! The first level features a welcomin...	2 beds \| 2 baths \| 1,000 sq.ft.	$239,900	Airbnb cash on cash: 2.14% Traditional cash on cash: 4.9% Airbnb Rental Income: $1502 Traditional Rental Income: $1688 Airbnb ROI: 2.14% Traditional ROI: 4.9%
1125 Sutherlyn Court Chesapeake, VA Welcome to your dream home! This stunning move-in ready brick residence is nestled on a se...	4 beds \| 3 baths \| 2,957 sq.ft.	$715,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 1.93% Airbnb Rental Income: $1811 Traditional Rental Income: $2655 Airbnb ROI: -0.07% Traditional ROI: 1.93%
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.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.91% Airbnb Rental Income: $null Traditional Rental Income: $2385 Airbnb ROI: N/A Traditional ROI: 2.91%
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.	$234,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 6.81% Airbnb Rental Income: $1309 Traditional Rental Income: $2040 Airbnb ROI: 1.67% Traditional ROI: 6.81%
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.	$247,500	Airbnb cash on cash: 2.33% Traditional cash on cash: 6.32% Airbnb Rental Income: $1510 Traditional Rental Income: $2004 Airbnb ROI: 2.33% Traditional ROI: 6.32%
801 Poindexter Street #314 Chesapeake, VA (some photos enhanced w/ AI or AI Staging) Spacious Condo Minutes from Norfolk Naval Base,...	1 beds \| 1 baths \| 1,135 sq.ft.	$193,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 6.73% Airbnb Rental Income: $1185 Traditional Rental Income: $1661 Airbnb ROI: 2.03% Traditional ROI: 6.73%
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.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.25% Airbnb Rental Income: $null Traditional Rental Income: $2971 Airbnb ROI: N/A Traditional ROI: 3.25%
1500 Blade Court Chesapeake, VA Well maintained, traditional brick home in the sought-after Emerald Forest neighborhood of...	4 beds \| 3 baths \| 4,082 sq.ft.	$795,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.82% Airbnb Rental Income: $null Traditional Rental Income: $2992 Airbnb ROI: N/A Traditional ROI: 1.82%
918 Seabreeze Court Chesapeake, VA Enjoy a great location near shopping and lots of restaurants, especially the new Towne Pla...	2 beds \| 2 baths \| 950 sq.ft.	$250,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 4.54% Airbnb Rental Income: $1502 Traditional Rental Income: $1651 Airbnb ROI: 2.05% Traditional ROI: 4.54%
404 Kings Bishop Court Chesapeake, VA Spacious split level single family home with 3 bedrooms & 2.5 bathrooms. Upgrades include ...	3 beds \| 3 baths \| 2,144 sq.ft.	$395,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 4.8% Airbnb Rental Income: $1398 Traditional Rental Income: $2570 Airbnb ROI: 0.5% Traditional ROI: 4.8%
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: 0.66% Traditional cash on cash: 4.14% Airbnb Rental Income: $1482 Traditional Rental Income: $2349 Airbnb ROI: 0.66% 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.	$248,900	Airbnb cash on cash: 2.31% Traditional cash on cash: 5.83% Airbnb Rental Income: $1510 Traditional Rental Income: $1898 Airbnb ROI: 2.31% Traditional ROI: 5.83%
1949 Rockwood Dr Chesapeake, VA Welcome to Summer Park! This 4-bedroom, 3-bath home in the sought-after Grassfield school ...	4 beds \| 3 baths \| 2,100 sq.ft.	$524,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $2570 Airbnb ROI: N/A Traditional ROI: 3.24%
25 King George Quay Chesapeake, VA Beautiful Brick End-Unit TownhomeThis stylish end-unit townhome features an open-concept l...	2 beds \| 3 baths \| 1,252 sq.ft.	$275,900	Airbnb cash on cash: 3.54% Traditional cash on cash: 5.16% Airbnb Rental Income: $2005 Traditional Rental Income: $1902 Airbnb ROI: 3.54% Traditional ROI: 5.16%
5029 John St Street Chesapeake, VA Spacious 4 bedroom, 2.5 bath two story home near highways, shopping and bases. Formal LR ...	4 beds \| 3 baths \| 2,014 sq.ft.	$370,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 5.94% Airbnb Rental Income: $1837 Traditional Rental Income: $2840 Airbnb ROI: 1.63% Traditional ROI: 5.94%
200 Essex Drive Chesapeake, VA	4 beds \| 2 baths \| 2,200 sq.ft.	$409,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 4.51% Airbnb Rental Income: $1716 Traditional Rental Income: $2540 Airbnb ROI: 1.12% Traditional ROI: 4.51%
4316 Hillingdon Bend #302 Chesapeake, VA Third Floor corner unit with balcony, updated kitchen cabinets and countertops, Open desig...	2 beds \| 2 baths \| 1,326 sq.ft.	$219,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 6.4% Airbnb Rental Income: $1309 Traditional Rental Income: $1820 Airbnb ROI: 1.97% Traditional ROI: 6.4%
2404 Livesay Road Chesapeake, VA Great starter home, just for you. Convenient to interstate, main roads, shopping and schoo...	4 beds \| 2 baths \| 1,145 sq.ft.	$285,000	Airbnb cash on cash: 3.71% Traditional cash on cash: 5.99% Airbnb Rental Income: $2122 Traditional Rental Income: $2191 Airbnb ROI: 3.71% Traditional ROI: 5.99%
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: 2.77% Traditional cash on cash: 7.12% Airbnb Rental Income: $1502 Traditional Rental Income: $1950 Airbnb ROI: 2.77% Traditional ROI: 7.12%
1209 Clearwater Lane Chesapeake, VA Charming 2 story home in Etheridge Lakes. Formal Living Room and Dining Room with moldings...	4 beds \| 3 baths \| 2,226 sq.ft.	$539,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $2714 Airbnb ROI: N/A Traditional ROI: 3.3%
2036 Maywood Street Chesapeake, VA Make this your first stop! Amazing opportunity priced to sell. This Single Family Home is ...	4 beds \| 2 baths \| 2,456 sq.ft.	$363,900	Airbnb cash on cash: 2.36% Traditional cash on cash: 5.56% Airbnb Rental Income: $2122 Traditional Rental Income: $2671 Airbnb ROI: 2.36% Traditional ROI: 5.56%
2916 Doris Avenue Chesapeake, VA Welcome to 2916 Doris Avenue, a well-maintained all-brick ranch in Sunrise Hills. This 3-b...	3 beds \| 2 baths \| 1,431 sq.ft.	$320,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 4.85% Airbnb Rental Income: $1780 Traditional Rental Income: $2081 Airbnb ROI: 2.23% Traditional ROI: 4.85%
522 Trolley Crossing Chesapeake, VA Welcome to 522 Trolley Crossing! This beautifully maintained end-unit townhome offers 3 sp...	3 beds \| 3 baths \| 1,470 sq.ft.	$300,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 4.65% Airbnb Rental Income: $1398 Traditional Rental Income: $2072 Airbnb ROI: 0.77% Traditional ROI: 4.65%
1235 Hull Street Chesapeake, VA Welcome home to this spacious 4-bedroom, 2.5-bath beauty in historic South Norfolk! Step i...	4 beds \| 3 baths \| 1,424 sq.ft.	$289,900	Airbnb cash on cash: 3.62% Traditional cash on cash: 6.19% Airbnb Rental Income: $2124 Traditional Rental Income: $2282 Airbnb ROI: 3.62% Traditional ROI: 6.19%
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: 2.72% Traditional cash on cash: 4.8% Airbnb Rental Income: $1780 Traditional Rental Income: $1866 Airbnb ROI: 2.72% Traditional ROI: 4.8%
303 Middle Oaks Drive Chesapeake, VA Nicely appointed townhome, great location, close to amenities. No HOA, POA or condo fees. ...	2 beds \| 3 baths \| 1,330 sq.ft.	$295,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 4.52% Airbnb Rental Income: $1423 Traditional Rental Income: $1882 Airbnb ROI: 1.33% Traditional ROI: 4.52%
415 Triton Trace Chesapeake, VA Visit this one first! This home is located in the desirable Grassfield school district and...	4 beds \| 3 baths \| 1,845 sq.ft.	$470,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $2508 Airbnb ROI: N/A Traditional ROI: 3.83%
4308 Center Mast Crest Chesapeake, VA This well-maintained four-bedroom home features fresh paint inside and attractive engineer...	4 beds \| 3 baths \| 2,235 sq.ft.	$380,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 5.33% Airbnb Rental Income: $3312 Traditional Rental Income: $2665 Airbnb ROI: 5.07% Traditional ROI: 5.33%
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: 2.24% Traditional cash on cash: 4.61% Airbnb Rental Income: $1837 Traditional Rental Income: $2067 Airbnb ROI: 2.24% Traditional ROI: 4.61%
300 Grain Way Chesapeake, VA Escape to your own slice of tranquility in this beautifully maintained 4-bedroom home, ne...	4 beds \| 2 baths \| 1,800 sq.ft.	$430,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 4.65% Airbnb Rental Income: $2122 Traditional Rental Income: $2700 Airbnb ROI: 1.87% Traditional ROI: 4.65%
4309 Hillingdon Bend #303 Chesapeake, VA Welcome to Unit 303 at Kings Pointe, a perfect blend of comfort and convenience! Located j...	2 beds \| 2 baths \| 1,367 sq.ft.	$229,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 6.39% Airbnb Rental Income: $1309 Traditional Rental Income: $1899 Airbnb ROI: 1.79% Traditional ROI: 6.39%
1201 Country Road Chesapeake, VA Welcome to this inviting 3-bedroom, 2.5-bath home offering modern comfort and style with 9...	3 beds \| 3 baths \| 1,568 sq.ft.	$330,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 4.1% Airbnb Rental Income: $1355 Traditional Rental Income: $1935 Airbnb ROI: 0.89% Traditional ROI: 4.1%
832 Doe Run Drive Chesapeake, VA Beautiful Home in the Heart of Great Bridge! Rare Opportunity! In-Ground Salt Water Pool, ...	5 beds \| 3 baths \| 2,814 sq.ft.	$619,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.15% Airbnb Rental Income: $null Traditional Rental Income: $3538 Airbnb ROI: N/A Traditional ROI: 4.15%
1027 Stillmeadows Court Chesapeake, VA Beautifully updated home in sought-after Greenbrier Woods! Soaring vaulted ceilings and an...	4 beds \| 3 baths \| 2,147 sq.ft.	$465,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 4.09% Airbnb Rental Income: $1716 Traditional Rental Income: $2746 Airbnb ROI: 0.64% Traditional ROI: 4.09%
553 Waters Road Chesapeake, VA Welcome Home! This Chesapeake gem sits on a spacious corner lot with 4 large bedrooms and ...	4 beds \| 3 baths \| 2,387 sq.ft.	$580,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 3.18% Airbnb Rental Income: $1811 Traditional Rental Income: $2807 Airbnb ROI: 0.44% Traditional ROI: 3.18%
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.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.87% Airbnb Rental Income: $null Traditional Rental Income: $2872 Airbnb ROI: N/A Traditional ROI: 2.87%
1208 Willow Avenue Chesapeake, VA Welcome to this charming Cape Cod in Norfolk Highlands! Step inside this beautiful 4 bedro...	4 beds \| 2 baths \| 1,791 sq.ft.	$375,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 4.89% Airbnb Rental Income: $2405 Traditional Rental Income: $2431 Airbnb ROI: 3.14% Traditional ROI: 4.89%
3549 Clover Meadows Drive Chesapeake, VA Super cute and move-in ready! This updated 2 bedrooms, 2 bath first-floor condo in Western...	2 beds \| 2 baths \| 960 sq.ft.	$170,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 8.15% Airbnb Rental Income: $1309 Traditional Rental Income: $1689 Airbnb ROI: 3.29% Traditional ROI: 8.15%

Real Estate investment in Chesapeake, VA

There are 516 properties for sale in the city of Chesapeake . The median list price in Chesapeake is $449,450 and the average price per square foot is $206. In October 2025, the average monthly cash on cash return in Chesapeake is 4.00%. The average monthly rental income in Chesapeake is $2,562.

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

There are 516 investment properties available for sale in Chesapeake.

In 2025, the best neighborhood to buy investment property is Greenbrier West.

The ROI for Long-Term is higher than the Short-Term in Chesapeake with average rental income of $2,562.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake, VA

2929 Hilton Avenue

Chesapeake, VA

4 beds | 2 baths | 1,747 sq.ft.

$310,000

Airbnb cash on cash: 4.01%

Traditional cash on cash: 5.87%

Airbnb Rental Income: $2405

Traditional Rental Income: $2358

Airbnb ROI: 4.01%

Traditional ROI: 5.87%

1408 Ashton Street

Chesapeake, VA

4 beds | 3 baths | 1,900 sq.ft.

$379,900

Airbnb cash on cash: 5.13%

Traditional cash on cash: 5.04%

Airbnb Rental Income: $3312

Traditional Rental Income: $2539

Airbnb ROI: 5.13%

Traditional ROI: 5.04%

929 Seabreeze Court

Chesapeake, VA

2 beds | 2 baths | 1,000 sq.ft.

$239,900

Airbnb cash on cash: 2.14%

Traditional cash on cash: 4.9%

Airbnb Rental Income: $1502

Traditional Rental Income: $1688

Airbnb ROI: 2.14%

Traditional ROI: 4.9%

1125 Sutherlyn Court

Chesapeake, VA

4 beds | 3 baths | 2,957 sq.ft.

$715,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 1.93%

Airbnb Rental Income: $1811

Traditional Rental Income: $2655

Airbnb ROI: -0.07%

Traditional ROI: 1.93%

641 Gallbush Road

Chesapeake, VA

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

$499,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.91%

Airbnb Rental Income: $null

Traditional Rental Income: $2385

Airbnb ROI: N/A

Traditional ROI: 2.91%

4308 Colindale Road #206

Chesapeake, VA

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

$234,000

Airbnb cash on cash: 1.67%

Traditional cash on cash: 6.81%

Airbnb Rental Income: $1309

Traditional Rental Income: $2040

Airbnb ROI: 1.67%

Traditional ROI: 6.81%

1016 Thoroughgood Way #307

Chesapeake, VA

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

$247,500

Airbnb cash on cash: 2.33%

Traditional cash on cash: 6.32%

Airbnb Rental Income: $1510

Traditional Rental Income: $2004

Airbnb ROI: 2.33%

Traditional ROI: 6.32%

801 Poindexter Street #314

Chesapeake, VA

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

$193,000

Airbnb cash on cash: 2.03%

Traditional cash on cash: 6.73%

Airbnb Rental Income: $1185

Traditional Rental Income: $1661

Airbnb ROI: 2.03%