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 Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Chesapeake, VA

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

Showing 360 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory 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
2856 Flag Road Chesapeake, VA Welcome Home! This charming 3-bedroom, 1-bathroom ranch-style home is in the heart of Deep...	3 beds \| 1 baths \| 1,319 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.52% Airbnb Rental Income: $null Traditional Rental Income: $1695 Airbnb ROI: N/A Traditional ROI: 3.52%
1439 Thistlewood Lane Chesapeake, VA BACK ON MARKET due to the buyer not being able to close. Beautifully maintained and update...	2 beds \| 2 baths \| 1,727 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.31% Airbnb Rental Income: $null Traditional Rental Income: $2208 Airbnb ROI: N/A Traditional ROI: 2.31%
627 Emerald Court Chesapeake, VA Discover a special surprise on a quiet cul-de-sac in the heart of Greenbrier. This charmin...	4 beds \| 3 baths \| 2,887 sq.ft.	$560,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.98% Airbnb Rental Income: $null Traditional Rental Income: $3176 Airbnb ROI: N/A Traditional ROI: 3.98%
2220 Ardmore Avenue Chesapeake, VA If you've been waiting for something that feels easy, updated, and livable in Chesapeake, ...	4 beds \| 2 baths \| 1,600 sq.ft.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.76% Airbnb Rental Income: $null Traditional Rental Income: $2268 Airbnb ROI: N/A Traditional ROI: 4.76%
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.	$534,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.7% Airbnb Rental Income: $null Traditional Rental Income: $2385 Airbnb ROI: N/A Traditional ROI: 2.7%
1024 Middle Street Chesapeake, VA What a find! Spacious and modern colonial style home in a great location near shopping, s...	3 beds \| 3 baths \| 1,500 sq.ft.	$329,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $1900 Airbnb ROI: N/A Traditional ROI: 3.93%
3204 Bruno Drive Chesapeake, VA Make this your first stop! This beautiful brick ranch blends modern updates with classic c...	4 beds \| 2 baths \| 1,800 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.95% Airbnb Rental Income: $null Traditional Rental Income: $2148 Airbnb ROI: N/A Traditional ROI: 3.95%
1016 Thoroughgood Way #307 Chesapeake, VA Make this your first stop! Beautiful Balcony Views. Well maintained, low maintenance, open...	2 beds \| 2 baths \| 1,255 sq.ft.	$239,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.55% Airbnb Rental Income: $null Traditional Rental Income: $2004 Airbnb ROI: N/A Traditional ROI: 6.55%
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.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.2% Airbnb Rental Income: $null Traditional Rental Income: $2263 Airbnb ROI: N/A Traditional ROI: 5.2%
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.	$159,500	Airbnb cash on cash: N/A Traditional cash on cash: 8.31% Airbnb Rental Income: $null Traditional Rental Income: $1661 Airbnb ROI: N/A Traditional ROI: 8.31%
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.	$445,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.54% Airbnb Rental Income: $null Traditional Rental Income: $2730 Airbnb ROI: N/A Traditional ROI: 4.54%
1664 Teton Court Chesapeake, VA Beautiful pond-front home showcasing exceptional upgrades and thoughtful design throughout...	4 beds \| 3 baths \| 2,523 sq.ft.	$630,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $3135 Airbnb ROI: N/A Traditional ROI: 3.26%
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.	$288,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.21% Airbnb Rental Income: $null Traditional Rental Income: $1736 Airbnb ROI: N/A Traditional ROI: 4.21%
1040 Trestle Way Chesapeake, VA Welcome to 1040 Trestle Way, where comfort, style, and convenience come together in the he...	3 beds \| 3 baths \| 1,443 sq.ft.	$320,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $1900 Airbnb ROI: N/A Traditional ROI: 4.12%
1436 Scoonie Pointe Drive Chesapeake, VA Located in Eagle Pointe, Chesapeakeâs premier gated 55+ community, this private neighbor...	3 beds \| 2 baths \| 1,748 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $2115 Airbnb ROI: N/A Traditional ROI: 3.26%
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.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.24% Airbnb Rental Income: $null Traditional Rental Income: $2906 Airbnb ROI: N/A Traditional ROI: 4.24%
1312 Bunker Ridge Arch #B Chesapeake, VA Welcome home to your new condo in Greenbrier! Located just minutes from I-64, this single ...	3 beds \| 2 baths \| 1,591 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.26% Airbnb Rental Income: $null Traditional Rental Income: $2292 Airbnb ROI: N/A Traditional ROI: 5.26%
4000 Hamilton Street Chesapeake, VA This stunning 3-bed, 2-bath single-family home was completely transformed in 2023 â new ...	3 beds \| 2 baths \| 1,235 sq.ft.	$340,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $1722 Airbnb ROI: N/A Traditional ROI: 3.34%
1127 Norcova Court Chesapeake, VA Beautiful single family detached home in convenient Greenbrier area of Chesapeake, with pl...	4 beds \| 3 baths \| 2,410 sq.ft.	$489,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.81% Airbnb Rental Income: $null Traditional Rental Income: $3135 Airbnb ROI: N/A Traditional ROI: 4.81%
122 Grant Street Chesapeake, VA Updated 2-bedroom, 1-bath ranch in Chesapeake â move-in ready and packed with updates! C...	2 beds \| 1 baths \| 832 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.92% Airbnb Rental Income: $null Traditional Rental Income: $1430 Airbnb ROI: N/A Traditional ROI: 3.92%
325 Oak Lake Run Chesapeake, VA Welcome to this well-maintained 3-bedroom, 2-bath detached home in Chesapeakeâs desirabl...	3 beds \| 2 baths \| 1,446 sq.ft.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.8% Airbnb Rental Income: $null Traditional Rental Income: $2020 Airbnb ROI: N/A Traditional ROI: 3.8%
3932 Pierce Lane Chesapeake, VA	2 beds \| 2 baths \| 1,176 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.33% Airbnb Rental Income: $null Traditional Rental Income: $1541 Airbnb ROI: N/A Traditional ROI: 3.33%
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: N/A Traditional cash on cash: 4.8% Airbnb Rental Income: $null Traditional Rental Income: $1866 Airbnb ROI: N/A Traditional ROI: 4.8%
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: N/A Traditional cash on cash: 5.29% Airbnb Rental Income: $null Traditional Rental Income: $1675 Airbnb ROI: N/A Traditional ROI: 5.29%
3408 Albury CT Chesapeake, VA Over 3,400 sq ft on a quiet cul-de-sac in Western Branch! Featuring new floors, fresh pain...	4 beds \| 3 baths \| N/A	$515,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.43% Airbnb Rental Income: $null Traditional Rental Income: $3146 Airbnb ROI: N/A Traditional ROI: 4.43%
1016 Thoroughgood Way #101 Chesapeake, VA	2 beds \| 2 baths \| 1,166 sq.ft.	$230,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.19% Airbnb Rental Income: $null Traditional Rental Income: $1856 Airbnb ROI: N/A Traditional ROI: 6.19%
942 Brigantine Court Chesapeake, VA Welcome to 942 Brigantine Ct! This beautifully updated end-unit townhouse in the highly de...	3 beds \| 2 baths \| 1,140 sq.ft.	$289,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.21% Airbnb Rental Income: $null Traditional Rental Income: $1818 Airbnb ROI: N/A Traditional ROI: 4.21%
1731 Woodmill Street Chesapeake, VA Located in the heart of Chesapeakeâs Greenbrier area, this meticulously maintained detac...	3 beds \| 3 baths \| 1,867 sq.ft.	$390,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.29% Airbnb Rental Income: $null Traditional Rental Income: $2315 Airbnb ROI: N/A Traditional ROI: 4.29%
1308 Seaboard Avenue Chesapeake, VA Remodeled in 2019, this updated home offers just over 2,000 sq ft of inviting living space...	4 beds \| 3 baths \| 2,021 sq.ft.	$360,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.63% Airbnb Rental Income: $null Traditional Rental Income: $2638 Airbnb ROI: N/A Traditional ROI: 5.63%
728 Luther Street Chesapeake, VA This beautiful home is nestled into a cozy neighborhood in the heart of Great Bridge. Boa...	3 beds \| 3 baths \| 1,810 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $2397 Airbnb ROI: N/A Traditional ROI: 3.82%
3401 Cricket Hollow Lane Chesapeake, VA Beautifully updated end-unit townhome with an open, airy feel. Freshly painted interior wi...	2 beds \| 3 baths \| 1,512 sq.ft.	$324,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.33% Airbnb Rental Income: $null Traditional Rental Income: $1662 Airbnb ROI: N/A Traditional ROI: 3.33%
225 Vanette DR Chesapeake, VA This Great Bridge ranch is extra ""special""! With multi-level decks and patio this backya...	4 beds \| 2 baths \| N/A	$490,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.55% Airbnb Rental Income: $null Traditional Rental Income: $2588 Airbnb ROI: N/A Traditional ROI: 3.55%
1229 Decatur Street Chesapeake, VA This is such a lovely home with a fantastic backyard and oversized detached garage conveni...	3 beds \| 2 baths \| 1,332 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.47% Airbnb Rental Income: $null Traditional Rental Income: $1943 Airbnb ROI: N/A Traditional ROI: 5.47%
1108 Rockland Court Chesapeake, VA Welcome to this beautiful 4-bedroom, 2.5-bath home located in the highly sought-after Grea...	4 beds \| 3 baths \| 2,792 sq.ft.	$570,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.57% Airbnb Rental Income: $null Traditional Rental Income: $3040 Airbnb ROI: N/A Traditional ROI: 3.57%
700 CROSS Quay Chesapeake, VA Spacious and Open floor plan. Cathedral Ceilings & Sky Lights open to Large Eat-In Kitche...	4 beds \| 3 baths \| 3,295 sq.ft.	$709,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.02% Airbnb Rental Income: $null Traditional Rental Income: $2684 Airbnb ROI: N/A Traditional ROI: 2.02%
328 Alpine Drive Chesapeake, VA Beautifully updated 4-bedroom, 2-bath home in the heart of Great Bridge! Freshly painted w...	4 beds \| 2 baths \| 3,350 sq.ft.	$545,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.84% Airbnb Rental Income: $null Traditional Rental Income: $3040 Airbnb ROI: N/A Traditional ROI: 3.84%
1853 Rockwood Drive Chesapeake, VA Step into this beautiful home where rich hardwood floors warmly welcome you. The chefâs ...	4 beds \| 3 baths \| 3,050 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $3153 Airbnb ROI: N/A Traditional ROI: 3.29%
3502 Clover Meadows Drive Chesapeake, VA Low maintenance second floor condo with vaulted ceilings! This freshly painted unit is per...	2 beds \| 2 baths \| 960 sq.ft.	$155,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.83% Airbnb Rental Income: $null Traditional Rental Income: $1705 Airbnb ROI: N/A Traditional ROI: 8.83%
1819 Martin Avenue Chesapeake, VA THIS IS A PLACE YOU CAN CALL HOME. Solid brick home in a cul-de-sac offering durability, t...	3 beds \| 2 baths \| 1,250 sq.ft.	$215,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.71% Airbnb Rental Income: $null Traditional Rental Income: $2085 Airbnb ROI: N/A Traditional ROI: 7.71%
566 River Creek Road Chesapeake, VA Take a look at this charming 3 bedroom, 1.5 bath ranch! This home has been updated kitchen...	3 beds \| 2 baths \| 1,379 sq.ft.	$340,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.25% Airbnb Rental Income: $null Traditional Rental Income: $1734 Airbnb ROI: N/A Traditional ROI: 3.25%

Your search for investment property begins and ends here

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Chesapeake, VA

2856 Flag Road

Chesapeake, VA

3 beds | 1 baths | 1,319 sq.ft.

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.52%

Airbnb Rental Income: $null

Traditional Rental Income: $1695

Airbnb ROI: N/A

Traditional ROI: 3.52%

1439 Thistlewood Lane

Chesapeake, VA

2 beds | 2 baths | 1,727 sq.ft.

$425,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.31%

Airbnb Rental Income: $null

Traditional Rental Income: $2208

Airbnb ROI: N/A

Traditional ROI: 2.31%

627 Emerald Court

Chesapeake, VA

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

$560,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.98%

Airbnb Rental Income: $null

Traditional Rental Income: $3176

Airbnb ROI: N/A

Traditional ROI: 3.98%

2220 Ardmore Avenue

Chesapeake, VA

4 beds | 2 baths | 1,600 sq.ft.

$349,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.76%

Airbnb Rental Income: $null

Traditional Rental Income: $2268

Airbnb ROI: N/A

Traditional ROI: 4.76%

641 Gallbush Road

Chesapeake, VA

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

$534,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.7%

Airbnb Rental Income: $null

Traditional Rental Income: $2385

Airbnb ROI: N/A

Traditional ROI: 2.7%

1024 Middle Street

Chesapeake, VA

3 beds | 3 baths | 1,500 sq.ft.

$329,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.93%

Airbnb Rental Income: $null

Traditional Rental Income: $1900

Airbnb ROI: N/A

Traditional ROI: 3.93%

3204 Bruno Drive

Chesapeake, VA

4 beds | 2 baths | 1,800 sq.ft.

$375,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.95%

Airbnb Rental Income: $null

Traditional Rental Income: $2148

Airbnb ROI: N/A

Traditional ROI: 3.95%

1016 Thoroughgood Way #307

Chesapeake, VA

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

$239,999

Airbnb cash on cash: N/A

Traditional cash on cash: 6.55%

Airbnb Rental Income: $null

Traditional Rental Income: $2004

Airbnb ROI: N/A