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.

Single Family Homes for Sale in Chesapeake, VA

Search for Single Family Residential for Sale in Chesapeake, Virginia. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 447 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
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%
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%
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%
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%
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%
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%
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%
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.	$610,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 2.98% Airbnb Rental Income: $1716 Traditional Rental Income: $2807 Airbnb ROI: 0.23% Traditional ROI: 2.98%
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.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.68% Airbnb Rental Income: $null Traditional Rental Income: $2872 Airbnb ROI: N/A Traditional ROI: 2.68%
2005 Columbo Avenue Chesapeake, VA Located in the desirable Chittum and Western Branch school districts, this beautifully upd...	4 beds \| 3 baths \| 2,900 sq.ft.	$575,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 4.76% Airbnb Rental Income: $3312 Traditional Rental Income: $3606 Airbnb ROI: 2.83% Traditional ROI: 4.76%
5013 John Street Chesapeake, VA You're in for a treat at 5013 John Street in the Western Branch area of Chesapeake! This 4...	4 beds \| 3 baths \| 1,516 sq.ft.	$355,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 4.41% Airbnb Rental Income: $1837 Traditional Rental Income: $2193 Airbnb ROI: 1.86% Traditional ROI: 4.41%
1526 Jackson Avenue Chesapeake, VA Come see this lovely historic home on a quiet tree lined street. Enjoy both the nostalgic ...	3 beds \| 1 baths \| 1,304 sq.ft.	$240,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 5.76% Airbnb Rental Income: $1355 Traditional Rental Income: $1781 Airbnb ROI: 2.05% Traditional ROI: 5.76%
813 Kemp Meadow Drive Chesapeake, VA For sale in Kemp Crossing!!! 4 bedrooms, 2 full bathrooms, and a half bath downstairs, scr...	4 beds \| 3 baths \| 2,240 sq.ft.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.17% Airbnb Rental Income: $null Traditional Rental Income: $2795 Airbnb ROI: N/A Traditional ROI: 4.17%
547 Seahorse Run Chesapeake, VA Welcome to 547 Seahorse Run, located in the desirable Riverwalk community, this beautifull...	3 beds \| 3 baths \| 1,800 sq.ft.	$299,900	Airbnb cash on cash: 1.26% Traditional cash on cash: 5.92% Airbnb Rental Income: $1398 Traditional Rental Income: $2291 Airbnb ROI: 1.26% Traditional ROI: 5.92%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chesapeake, VA

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%

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%

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%

Traditional ROI: 2.04%

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.

$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

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

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%