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 Back on market due to no fault of the seller. Beautifully maintained and updated Condo in ...	2 beds \| 2 baths \| 1,727 sq.ft.	$435,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 2.23% Airbnb Rental Income: $2309 Traditional Rental Income: $2208 Airbnb ROI: 1.07% Traditional ROI: 2.23%
711 Villa Drive Chesapeake, VA 4 BR, 2.5 BA home in Chesapeake, Hickory district. Features a spacious layout, sparkling i...	4 beds \| 3 baths \| 2,454 sq.ft.	$547,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.19% Airbnb Rental Income: $null Traditional Rental Income: $3202 Airbnb ROI: N/A Traditional ROI: 4.19%
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.	$369,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 5.21% Airbnb Rental Income: $3312 Traditional Rental Income: $2539 Airbnb ROI: 5.3% Traditional ROI: 5.21%
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%
829 Donnington Drive Chesapeake, VA Beautiful 4-bed, 2.5 bath ranch-style home located in Ethridge Woods, a residential neighb...	4 beds \| 3 baths \| 2,651 sq.ft.	$599,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.86% Airbnb Rental Income: $null Traditional Rental Income: $3289 Airbnb ROI: N/A Traditional ROI: 3.86%
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 Spacious, move-in ready condo just minutes from Norfolk Naval Base, Portsmouth Shipyard, a...	1 beds \| 1 baths \| 1,135 sq.ft.	$190,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 6.85% Airbnb Rental Income: $1185 Traditional Rental Income: $1661 Airbnb ROI: 2.08% Traditional ROI: 6.85%
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.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $2971 Airbnb ROI: N/A Traditional ROI: 3.26%
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.	$390,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 4.87% Airbnb Rental Income: $1398 Traditional Rental Income: $2570 Airbnb ROI: 0.52% Traditional ROI: 4.87%
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: 3.49% Traditional cash on cash: 4.21% Airbnb Rental Income: $2762 Traditional Rental Income: $2385 Airbnb ROI: 3.49% Traditional ROI: 4.21%
805 Glen Oak Cove Chesapeake, VA Move in condition! Lovely, well cared for home.Updates:2025:New remodeled Bath (Tub, Vanit...	3 beds \| 2 baths \| 1,485 sq.ft.	$356,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 4.11% Airbnb Rental Income: $1632 Traditional Rental Income: $2083 Airbnb ROI: 1.38% Traditional ROI: 4.11%
1004 Saint Andrews Way #D Chesapeake, VA Come check out this adorable townhome in Saint Andrews Condos before it's gone! This open ...	2 beds \| 2 baths \| 1,026 sq.ft.	$224,900	Airbnb cash on cash: 2.71% Traditional cash on cash: 6.12% Airbnb Rental Income: $1502 Traditional Rental Income: $1788 Airbnb ROI: 2.71% Traditional ROI: 6.12%
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%
404 Tranquility Trace Chesapeake, VA Welcome to The Preserves, a serene neighborhood nestled within a short distance of the pic...	4 beds \| 3 baths \| 2,700 sq.ft.	$585,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 2.89% Airbnb Rental Income: $1716 Traditional Rental Income: $2831 Airbnb ROI: -0.02% Traditional ROI: 2.89%
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%
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.	$259,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 6.68% Airbnb Rental Income: $2122 Traditional Rental Income: $2191 Airbnb ROI: 4.18% Traditional ROI: 6.68%
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%
3204 Pioneer Lane Chesapeake, VA Welcome to your next opportunity in Chesapeake! This spacious 3-bedroom, 2-bath home offer...	3 beds \| 2 baths \| 1,853 sq.ft.	$360,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 4.72% Airbnb Rental Income: $1632 Traditional Rental Income: $2375 Airbnb ROI: 1.16% Traditional ROI: 4.72%
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.	$515,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.09% Airbnb Rental Income: $null Traditional Rental Income: $2906 Airbnb ROI: N/A Traditional ROI: 4.09%
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.	$297,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 4.71% Airbnb Rental Income: $1398 Traditional Rental Income: $2072 Airbnb ROI: 0.79% Traditional ROI: 4.71%
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, and amenities. No HOA, POA or condo fees. Come ...	2 beds \| 3 baths \| 1,330 sq.ft.	$285,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 4.71% Airbnb Rental Income: $1423 Traditional Rental Income: $1882 Airbnb ROI: 1.41% Traditional ROI: 4.71%
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.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.04% Airbnb Rental Income: $null Traditional Rental Income: $2508 Airbnb ROI: N/A Traditional ROI: 4.04%
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%
4921 Clifton Street Chesapeake, VA CLOSING COSTS NEGOTIABLE. SELLER TO REPLACE PATIO DOOR. SUPER 4 LARGE BEDROOMS HOME LOCATE...	4 beds \| 3 baths \| 2,203 sq.ft.	$429,900	Airbnb cash on cash: 1.21% Traditional cash on cash: 4.37% Airbnb Rental Income: $1837 Traditional Rental Income: $2613 Airbnb ROI: 1.21% Traditional ROI: 4.37%
4019 Sea Cliff Road Chesapeake, VA Welcome to 4019 Sea Cliff Rd , a beautifully refreshed home in a highly sought-after area ...	4 beds \| 2 baths \| 1,751 sq.ft.	$350,000	Airbnb cash on cash: 5.73% Traditional cash on cash: 4.74% Airbnb Rental Income: $3312 Traditional Rental Income: $2246 Airbnb ROI: 5.73% Traditional ROI: 4.74%
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.	$427,500	Airbnb cash on cash: 1.89% Traditional cash on cash: 4.68% Airbnb Rental Income: $2122 Traditional Rental Income: $2700 Airbnb ROI: 1.89% Traditional ROI: 4.68%
1421 Chesapeake Avenue Chesapeake, VA Perfect blend of timeless character and modern updates with this beautiful historic home. ...	3 beds \| 3 baths \| 2,070 sq.ft.	$348,500	Airbnb cash on cash: 0.73% Traditional cash on cash: 4.79% Airbnb Rental Income: $1355 Traditional Rental Income: $2267 Airbnb ROI: 0.73% Traditional ROI: 4.79%
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.	$649,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $2869 Airbnb ROI: N/A Traditional ROI: 2.64%
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.	$322,500	Airbnb cash on cash: 0.94% Traditional cash on cash: 4.22% Airbnb Rental Income: $1355 Traditional Rental Income: $1935 Airbnb ROI: 0.94% Traditional ROI: 4.22%
1016 Thoroughgood Way #101 Chesapeake, VA	2 beds \| 2 baths \| 1,166 sq.ft.	$230,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 6.19% Airbnb Rental Income: $1510 Traditional Rental Income: $1856 Airbnb ROI: 2.57% Traditional ROI: 6.19%
745 Lacy Oak Drive Chesapeake, VA Beautifully updated condo in excellent condition, offering modern upgrades and a thoughtfu...	2 beds \| 3 baths \| 1,870 sq.ft.	$335,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 5.16% Airbnb Rental Income: $1502 Traditional Rental Income: $2317 Airbnb ROI: 1.17% Traditional ROI: 5.16%
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%
4138 3rd Street Chesapeake, VA Check out this beautiful ranch home located in Portlock Terrace! The spacious back yard is...	3 beds \| 2 baths \| 1,500 sq.ft.	$350,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 4.99% Airbnb Rental Income: $1355 Traditional Rental Income: $2349 Airbnb ROI: 0.7% Traditional ROI: 4.99%
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.	$169,000	Airbnb cash on cash: 3.31% Traditional cash on cash: 8.2% Airbnb Rental Income: $1309 Traditional Rental Income: $1689 Airbnb ROI: 3.31% Traditional ROI: 8.2%

Real Estate investment in Chesapeake, VA

There are 524 properties for sale in the city of Chesapeake . The median list price in Chesapeake is $446,000 and the average price per square foot is $202. In October 2025, the average monthly cash on cash return in Chesapeake is 4.00%. The average monthly rental income in Chesapeake is $2,554.

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

There are 524 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 $2,554.

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.

$435,000

Airbnb cash on cash: 1.07%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $2309

Traditional Rental Income: $2208

Airbnb ROI: 1.07%

Traditional ROI: 2.23%

711 Villa Drive

Chesapeake, VA

4 beds | 3 baths | 2,454 sq.ft.

$547,500

Airbnb cash on cash: N/A

Traditional cash on cash: 4.19%

Airbnb Rental Income: $null

Traditional Rental Income: $3202

Airbnb ROI: N/A

Traditional ROI: 4.19%

1408 Ashton Street

Chesapeake, VA

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

$369,000

Airbnb cash on cash: 5.3%

Traditional cash on cash: 5.21%

Airbnb Rental Income: $3312

Traditional Rental Income: $2539

Airbnb ROI: 5.3%

Traditional ROI: 5.21%

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%

829 Donnington Drive

Chesapeake, VA

4 beds | 3 baths | 2,651 sq.ft.

$599,999

Airbnb cash on cash: N/A

Traditional cash on cash: 3.86%

Airbnb Rental Income: $null

Traditional Rental Income: $3289

Airbnb ROI: N/A

Traditional ROI: 3.86%

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.

$190,000

Airbnb cash on cash: 2.08%

Traditional cash on cash: 6.85%

Airbnb Rental Income: $1185

Traditional Rental Income: $1661

Airbnb ROI: 2.08%

Traditional ROI: 6.85%

828 Woodstream Way

Chesapeake, VA

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

$599,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.26%

Airbnb Rental Income: $null

Traditional Rental Income: $2971

Airbnb ROI: N/A