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
420 Faire Chase Chesapeake, VA MOVE IN READY! Lovely two bedroom, 2.5 bath townhome located in the desirable Great Bridge...	2 beds \| 3 baths \| 1,208 sq.ft.	$290,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 4.5% Airbnb Rental Income: $1757 Traditional Rental Income: $1833 Airbnb ROI: 2.46% Traditional ROI: 4.5%
2929 Hilton Avenue Chesapeake, VA Great spacious 4-bedroom, 2-bath ranch featuring large bedrooms; large primary suite compl...	4 beds \| 2 baths \| 1,747 sq.ft.	$339,000	Airbnb cash on cash: 3.59% Traditional cash on cash: 5.29% Airbnb Rental Income: $2405 Traditional Rental Income: $2358 Airbnb ROI: 3.59% Traditional ROI: 5.29%
1320 Sommerton Way Chesapeake, VA Beautiful, Beautiful Are The Words To Describe This Former Model Home Built By Stephen Ale...	4 beds \| 3 baths \| 2,524 sq.ft.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $2731 Airbnb ROI: N/A Traditional ROI: 3.83%
1605 Stones Throw Court #A Chesapeake, VA Welcome home! 1605A Stones Throw is a move-in ready 2-bedroom, 2-bath first-floor condo in...	2 beds \| 2 baths \| 978 sq.ft.	$199,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 6.88% Airbnb Rental Income: $2005 Traditional Rental Income: $1758 Airbnb ROI: 5.42% Traditional ROI: 6.88%
421 Green Meadow Drive Chesapeake, VA WELCOME HOME TO YOUR NEW CONDO. MODERN AND SLEEK EXTERIOR DESIGN. THE INTERIOR HAS A BEA...	3 beds \| 3 baths \| 1,804 sq.ft.	$365,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 4.77% Airbnb Rental Income: $1632 Traditional Rental Income: $2302 Airbnb ROI: 1.47% Traditional ROI: 4.77%
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.	$249,900	Airbnb cash on cash: 2.02% Traditional cash on cash: 4.67% Airbnb Rental Income: $1502 Traditional Rental Income: $1688 Airbnb ROI: 2.02% Traditional ROI: 4.67%
301 Diamond Avenue Chesapeake, VA Discover this beautiful 4-bed, 3-bath home built in 2016, set on a corner lot in Pleasant ...	4 beds \| 3 baths \| 1,964 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $2533 Airbnb ROI: N/A Traditional ROI: 4.73%
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.	$689,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 2.04% Airbnb Rental Income: $1716 Traditional Rental Income: $2655 Airbnb ROI: -0.16% Traditional ROI: 2.04%
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.	$239,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 6.65% Airbnb Rental Income: $1309 Traditional Rental Income: $2040 Airbnb ROI: 1.62% Traditional ROI: 6.65%
608 Stoneleigh Court Chesapeake, VA Welcome to this stunning all-brick home located on a quiet cul-de-sac in a sought-after ne...	4 beds \| 3 baths \| 2,578 sq.ft.	$690,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.12% Airbnb Rental Income: $null Traditional Rental Income: $3252 Airbnb ROI: N/A Traditional ROI: 3.12%
2704 Fincham Court Chesapeake, VA This charming ranch home offers it all â nestled on a quiet cul-de-sac just north of Gre...	4 beds \| 2 baths \| 1,664 sq.ft.	$339,900	Airbnb cash on cash: 3.48% Traditional cash on cash: 5.16% Airbnb Rental Income: $2405 Traditional Rental Income: $2353 Airbnb ROI: 3.48% Traditional ROI: 5.16%
801 Poindexter Street #314 Chesapeake, VA This great condo located in the heart of SoNo is just waiting for you. New flooring and re...	1 beds \| 1 baths \| 1,135 sq.ft.	$205,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 6.29% Airbnb Rental Income: $1185 Traditional Rental Income: $1661 Airbnb ROI: 1.86% Traditional ROI: 6.29%
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%
5029 Pughsville Road Chesapeake, VA Dont miss this opportunity to buy here in Western Branch. Well maintained home new paint t...	3 beds \| 3 baths \| 1,902 sq.ft.	$414,556	Airbnb cash on cash: 0.61% Traditional cash on cash: 3.96% Airbnb Rental Income: $1482 Traditional Rental Income: $2349 Airbnb ROI: 0.61% Traditional ROI: 3.96%
724 Humphries Lane Chesapeake, VA Welcome to 724 Humphries Lane, a charming 3-bedroom ranch located on a quiet cul-de-sac in...	3 beds \| 1 baths \| 1,000 sq.ft.	$299,900	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.49% Airbnb Rental Income: $1312 Traditional Rental Income: $1639 Airbnb ROI: 0.89% Traditional ROI: 3.49%
1029 Harwich Drive Chesapeake, VA This beautiful home features 2 downstairs masters. Perfect for multi-generational family. ...	4 beds \| 4 baths \| 3,502 sq.ft.	$639,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.71% Airbnb Rental Income: $null Traditional Rental Income: $4101 Airbnb ROI: N/A Traditional ROI: 4.71%
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.	$419,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 4.38% Airbnb Rental Income: $1716 Traditional Rental Income: $2540 Airbnb ROI: 1.07% Traditional ROI: 4.38%
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.	$305,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 5.54% Airbnb Rental Income: $2122 Traditional Rental Income: $2191 Airbnb ROI: 3.41% Traditional ROI: 5.54%
3403 Frost Flower Court Chesapeake, VA Move in ready home in the heart of Deep Creek. This 1.5 story Ranch sits at the end of the...	4 beds \| 2 baths \| 1,639 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.07% Airbnb Rental Income: $null Traditional Rental Income: $2316 Airbnb ROI: N/A Traditional ROI: 4.07%
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%
3204 Pioneer Lane Chesapeake, VA Welcome Home to 3204 Pioneer Lane. A beautiful, 1,853 square foot, brick rancher on a 1.18...	3 beds \| 2 baths \| 1,853 sq.ft.	$419,999	Airbnb cash on cash: 0.86% Traditional cash on cash: 3.92% Airbnb Rental Income: $1632 Traditional Rental Income: $2375 Airbnb ROI: 0.86% Traditional ROI: 3.92%
1025 Stillmeadows Court Chesapeake, VA Welcome to this spacious 4-bedroom, 2.5-bath home offering 2,024 square feet of comfortabl...	4 beds \| 3 baths \| 2,024 sq.ft.	$469,990	Airbnb cash on cash: 0.62% Traditional cash on cash: 3.41% Airbnb Rental Income: $1716 Traditional Rental Income: $2465 Airbnb ROI: 0.62% Traditional ROI: 3.41%
2916 Doris Avenue Chesapeake, VA Welcome to 2916 Doris Avenue, a well-maintained all-brick ranch in the vibrant Sunrise Hil...	3 beds \| 2 baths \| 1,431 sq.ft.	$325,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 4.76% Airbnb Rental Income: $1780 Traditional Rental Income: $2081 Airbnb ROI: 2.18% Traditional ROI: 4.76%
108 Grant Street Chesapeake, VA Charming All-Brick Ranch in Great Bridge School District!Move right into this beautifully ...	3 beds \| 2 baths \| 1,232 sq.ft.	$299,900	Airbnb cash on cash: 1.18% Traditional cash on cash: 4.67% Airbnb Rental Income: $1355 Traditional Rental Income: $1927 Airbnb ROI: 1.18% Traditional ROI: 4.67%
4117 River Breeze Circle Chesapeake, VA Beautiful Condo in Western Branch â Spacious, Stylish, and Move-In Ready!Nestled on a ch...	3 beds \| 3 baths \| 1,957 sq.ft.	$335,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 5.5% Airbnb Rental Income: $1536 Traditional Rental Income: $2346 Airbnb ROI: 1.51% Traditional ROI: 5.5%
273 Haviland Road Chesapeake, VA Modern Upgrades, Bonus Space & Prime Location! Donât miss this beautiful brick ranch lo...	4 beds \| 2 baths \| 2,428 sq.ft.	$445,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 4.06% Airbnb Rental Income: $1716 Traditional Rental Income: $2536 Airbnb ROI: 0.95% Traditional ROI: 4.06%
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%
324 Woodards Ford Road Chesapeake, VA This one-of-a-kind English Tudor home sits on an amazing 3-acre lot in one of best neighbo...	4 beds \| 3 baths \| 3,800 sq.ft.	$729,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $2841 Airbnb ROI: N/A Traditional ROI: 2.16%
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%
311 Carver Street Chesapeake, VA Welcome to 311 Carver â a spacious 4-bedroom, 2.5-bath home on a large corner lot in sou...	4 beds \| 3 baths \| 2,300 sq.ft.	$419,900	Airbnb cash on cash: 1% Traditional cash on cash: 4.67% Airbnb Rental Income: $1716 Traditional Rental Income: $2684 Airbnb ROI: 1% Traditional ROI: 4.67%
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.	$305,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 4.34% Airbnb Rental Income: $1757 Traditional Rental Income: $1882 Airbnb ROI: 2.23% Traditional ROI: 4.34%
1241 Monarch Reach Chesapeake, VA This beautifully maintained home offers comfort, functionality, and charm. The first floor...	4 beds \| 3 baths \| 3,010 sq.ft.	$589,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 3.42% Airbnb Rental Income: $1716 Traditional Rental Income: $3057 Airbnb ROI: 0.13% Traditional ROI: 3.42%
4308 Center Mast Crest Chesapeake, VA Sitting on one of the largest lots in the community, this home offers a backyard perfect f...	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%
1710 Willow Point Arch Chesapeake, VA Welcome to this wonderful 2-bedroom, 2-bath home featuring, modern LVP flooring, upgraded ...	2 beds \| 2 baths \| 1,308 sq.ft.	$250,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 5.49% Airbnb Rental Income: $1502 Traditional Rental Income: $1838 Airbnb ROI: 2.2% Traditional ROI: 5.49%
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.	$349,900	Airbnb cash on cash: 0.73% Traditional cash on cash: 4.76% Airbnb Rental Income: $1355 Traditional Rental Income: $2267 Airbnb ROI: 0.73% Traditional ROI: 4.76%
803 Minna Lane Chesapeake, VA Welcome to your new home in the Grassfield district. This beautiful home features an open ...	5 beds \| 3 baths \| 2,662 sq.ft.	$639,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.83% Airbnb Rental Income: $null Traditional Rental Income: $2929 Airbnb ROI: N/A Traditional ROI: 2.83%
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%
914 Godwin Avenue Chesapeake, VA Beautifully maintained 4-bedroom, 2.5-bath home with a 1-car garage in a prime central Che...	4 beds \| 3 baths \| 1,900 sq.ft.	$359,900	Airbnb cash on cash: 2.46% Traditional cash on cash: 5.17% Airbnb Rental Income: $2124 Traditional Rental Income: $2497 Airbnb ROI: 2.46% Traditional ROI: 5.17%

Real Estate investment in Chesapeake, VA

There are 538 properties for sale in the city of Chesapeake . The median list price in Chesapeake is $445,000 and the average price per square foot is $203. In September 2025, the average monthly cash on cash return in Chesapeake is 4.00%. The average monthly rental income in Chesapeake is $2,524.

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

There are 538 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 $2,524.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake, VA

420 Faire Chase

Chesapeake, VA

2 beds | 3 baths | 1,208 sq.ft.

$290,000

Airbnb cash on cash: 2.46%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $1757

Traditional Rental Income: $1833

Airbnb ROI: 2.46%

Traditional ROI: 4.5%

2929 Hilton Avenue

Chesapeake, VA

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

$339,000

Airbnb cash on cash: 3.59%

Traditional cash on cash: 5.29%

Airbnb Rental Income: $2405

Traditional Rental Income: $2358

Airbnb ROI: 3.59%

Traditional ROI: 5.29%

1320 Sommerton Way

Chesapeake, VA

4 beds | 3 baths | 2,524 sq.ft.

$495,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.83%

Airbnb Rental Income: $null

Traditional Rental Income: $2731

Airbnb ROI: N/A

Traditional ROI: 3.83%

1605 Stones Throw Court #A

Chesapeake, VA

2 beds | 2 baths | 978 sq.ft.

$199,000

Airbnb cash on cash: 5.42%

Traditional cash on cash: 6.88%

Airbnb Rental Income: $2005

Traditional Rental Income: $1758

Airbnb ROI: 5.42%

Traditional ROI: 6.88%

421 Green Meadow Drive

Chesapeake, VA

3 beds | 3 baths | 1,804 sq.ft.

$365,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $1632

Traditional Rental Income: $2302

Airbnb ROI: 1.47%

Traditional ROI: 4.77%

929 Seabreeze Court

Chesapeake, VA

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

$249,900

Airbnb cash on cash: 2.02%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $1502

Traditional Rental Income: $1688

Airbnb ROI: 2.02%

Traditional ROI: 4.67%

301 Diamond Avenue

Chesapeake, VA

4 beds | 3 baths | 1,964 sq.ft.

$395,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.73%

Airbnb Rental Income: $null

Traditional Rental Income: $2533

Airbnb ROI: N/A

Traditional ROI: 4.73%

1125 Sutherlyn Court

Chesapeake, VA

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

$689,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $1716

Traditional Rental Income: $2655

Airbnb ROI: -0.16%