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.

Condos for Sale in Chesapeake, VA

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

Showing 27 Condo 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
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: -0.12% Traditional cash on cash: 6.55% Airbnb Rental Income: $818 Traditional Rental Income: $2004 Airbnb ROI: -0.12% Traditional ROI: 6.55%
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: 2.93% Traditional cash on cash: 8.31% Airbnb Rental Income: $1237 Traditional Rental Income: $1661 Airbnb ROI: 2.93% Traditional ROI: 8.31%
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: 1.14% Traditional cash on cash: 4.49% Airbnb Rental Income: $1466 Traditional Rental Income: $2058 Airbnb ROI: 1.14% Traditional ROI: 4.49%
1016 Thoroughgood Way #101 Chesapeake, VA	2 beds \| 2 baths \| 1,166 sq.ft.	$230,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 6.19% Airbnb Rental Income: $818 Traditional Rental Income: $1856 Airbnb ROI: -0.08% Traditional ROI: 6.19%
1462 Titchfield Drive Chesapeake, VA Welcome to effortless living in this beautifully maintained 2-bedroom, 2.5-bath condo nest...	2 beds \| 3 baths \| 1,350 sq.ft.	$285,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 5.33% Airbnb Rental Income: $1257 Traditional Rental Income: $2027 Airbnb ROI: 0.98% Traditional ROI: 5.33%
712 Inlet Quay #A Chesapeake, VA Move-in ready and one-level living! This spacious 2-bedroom, 2-bath home offers 1,304 sq f...	2 beds \| 2 baths \| 1,304 sq.ft.	$275,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 4.8% Airbnb Rental Income: $960 Traditional Rental Income: $1859 Airbnb ROI: -0.02% Traditional ROI: 4.8%
902 CENTURION Circle Chesapeake, VA Beautifully maintained 3-bedroom, 2-bath home located in the highly desirable Grassfield s...	3 beds \| 3 baths \| 1,679 sq.ft.	$419,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 4.41% Airbnb Rental Income: $1039 Traditional Rental Income: $2503 Airbnb ROI: -0.24% Traditional ROI: 4.41%
704 Inlet Quay #J Chesapeake, VA Located in the heart of Riverwalk, this second-floor condo features cathedral ceilings in ...	3 beds \| 2 baths \| 1,523 sq.ft.	$295,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 5.14% Airbnb Rental Income: $1466 Traditional Rental Income: $2078 Airbnb ROI: 1.38% Traditional ROI: 5.14%
1505 Waitsel Drive #308 Chesapeake, VA Nearly new corner condo w/ white shaker cabinets, bright kitchen w/ sparkling quartz islan...	2 beds \| 2 baths \| 1,418 sq.ft.	$329,900	Airbnb cash on cash: -0.17% Traditional cash on cash: 4.08% Airbnb Rental Income: $960 Traditional Rental Income: $1928 Airbnb ROI: -0.17% Traditional ROI: 4.08%
1217 Welles Court Chesapeake, VA Opportunity in Chesapeakeâs sought-after Greenbrier area! This well-maintained home offe...	3 beds \| 3 baths \| 1,600 sq.ft.	$345,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 3.94% Airbnb Rental Income: $1123 Traditional Rental Income: $2037 Airbnb ROI: -0.04% Traditional ROI: 3.94%
102 Diamond Avenue #D Chesapeake, VA A Diamond Condo with NO FEES! Located in the highly sought-after Grassfield school distric...	2 beds \| 1 baths \| 988 sq.ft.	$250,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 4.05% Airbnb Rental Income: $644 Traditional Rental Income: $1452 Airbnb ROI: -0.62% Traditional ROI: 4.05%
1016 Thoroughgood Way #104 Chesapeake, VA Step into comfort and style at this beautifully refreshed 2 bed/2 bath first-floor condo i...	2 beds \| 2 baths \| 1,285 sq.ft.	$235,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 6.69% Airbnb Rental Income: $818 Traditional Rental Income: $2021 Airbnb ROI: -0.19% Traditional ROI: 6.69%
1513 Caden Lane #29 Chesapeake, VA Discover the perfect blend of luxury, comfort, and convenience in this beautifully designe...	3 beds \| 2 baths \| 2,005 sq.ft.	$774,500	Airbnb cash on cash: -1.29% Traditional cash on cash: 0.99% Airbnb Rental Income: $1105 Traditional Rental Income: $2376 Airbnb ROI: -1.29% Traditional ROI: 0.99%
936 Biltmore Way #37 Chesapeake, VA The Retreat at Kemps River, a highly sought-after 55+ community nestled in the heart of Gr...	3 beds \| 3 baths \| 2,112 sq.ft.	$490,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 3.27% Airbnb Rental Income: $1623 Traditional Rental Income: $2480 Airbnb ROI: 0.4% Traditional ROI: 3.27%
1509 Waitsel Drive #207 Chesapeake, VA Wake up to sparkling water views from every room in this stunning, nearly new end-unit con...	2 beds \| 2 baths \| 1,418 sq.ft.	$345,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 5.33% Airbnb Rental Income: $960 Traditional Rental Income: $2401 Airbnb ROI: -0.19% Traditional ROI: 5.33%
140 Springer Lane #232 Chesapeake, VA Charming 2-Bedroom Condo with Dual Balconies, a large walk-in closet and a private bathroo...	2 beds \| 3 baths \| 1,642 sq.ft.	$278,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 5.79% Airbnb Rental Income: $960 Traditional Rental Income: $2092 Airbnb ROI: 0.14% Traditional ROI: 5.79%
1015 Winged Foot Court #A Chesapeake, VA Beautiful two-story condo overlooking the 17th hole of Greenbrier Country Club Golf course...	2 beds \| 2 baths \| 1,589 sq.ft.	$334,000	Airbnb cash on cash: -1.31% Traditional cash on cash: 3.69% Airbnb Rental Income: $960 Traditional Rental Income: $2179 Airbnb ROI: -1.31% Traditional ROI: 3.69%
4316 Hillingdon Bend #304 Chesapeake, VA The Hanover Model. Beautiful open modern floor plan with 9 ft ceiling thought this stylish...	2 beds \| 2 baths \| 1,300 sq.ft.	$230,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 6.31% Airbnb Rental Income: $1189 Traditional Rental Income: $1882 Airbnb ROI: 1.34% Traditional ROI: 6.31%
3943 Rex Circle Chesapeake, VA Completely renovated and move-in ready, this stunning condo is located in the highly desir...	2 beds \| 2 baths \| 1,650 sq.ft.	$279,900	Airbnb cash on cash: 0.26% Traditional cash on cash: 5.94% Airbnb Rental Income: $1034 Traditional Rental Income: $2170 Airbnb ROI: 0.26% Traditional ROI: 5.94%
937 Shoal Creek Trail #B Chesapeake, VA Introducing a charming townhouse style condo nestled in the desirable Greenbrier area. Enj...	3 beds \| 3 baths \| 1,419 sq.ft.	$340,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 4.1% Airbnb Rental Income: $1466 Traditional Rental Income: $2010 Airbnb ROI: 1.04% Traditional ROI: 4.1%
720 Inlet Quay #A Chesapeake, VA First floor unit in desirable Riverwalk community. Enjoy all of the amenities of the commu...	2 beds \| 2 baths \| 1,304 sq.ft.	$270,000	Airbnb cash on cash: 0% Traditional cash on cash: 4.91% Airbnb Rental Income: $960 Traditional Rental Income: $1860 Airbnb ROI: 0% Traditional ROI: 4.91%
1601 Stone Moss Reach #C Chesapeake, VA This is it! Move-in ready at a phenomenal price! Step into this second-level condo that fe...	2 beds \| 1 baths \| 822 sq.ft.	$219,500	Airbnb cash on cash: 2.44% Traditional cash on cash: 4.46% Airbnb Rental Income: $1444 Traditional Rental Income: $1433 Airbnb ROI: 2.44% Traditional ROI: 4.46%
2200 Rock Cliff Reach #D Chesapeake, VA Adorable 2-Bedroom, 1-Bath Condo in the Heart of Greenbrier. All the appliances you need ...	2 beds \| 1 baths \| 822 sq.ft.	$199,900	Airbnb cash on cash: 1.55% Traditional cash on cash: 4.13% Airbnb Rental Income: $1444 Traditional Rental Income: $1505 Airbnb ROI: 1.55% Traditional ROI: 4.13%
1016 Thoroughgood Way #306 Chesapeake, VA Enjoy stylish, low-maintenance living in this beautifully maintained, one-owner 3rd-floor ...	2 beds \| 2 baths \| 1,213 sq.ft.	$249,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 5.9% Airbnb Rental Income: $818 Traditional Rental Income: $1936 Airbnb ROI: -0.24% Traditional ROI: 5.9%
2312 Willow Point Arch Chesapeake, VA This is a pristine 2 bedroom, 2 bath condo all on the 2nd level. It offers natural light b...	2 beds \| 2 baths \| 1,125 sq.ft.	$255,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 5.24% Airbnb Rental Income: $960 Traditional Rental Income: $1799 Airbnb ROI: 0.3% Traditional ROI: 5.24%
1501 Rosehill Drive #46 Chesapeake, VA Welcome home to The Retreat at Greenbrier, a sought-after 55+ community in the heart of Ch...	3 beds \| 3 baths \| 2,062 sq.ft.	$500,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.31% Airbnb Rental Income: $1623 Traditional Rental Income: $2518 Airbnb ROI: 0.42% Traditional ROI: 3.31%
309 Wimbledon Chase #E Chesapeake, VA Welcome to this beautiful 2BR/2BA, well-maintained and updated townhouse-style end-unit co...	2 beds \| 2 baths \| 1,000 sq.ft.	$218,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 5.3% Airbnb Rental Income: $960 Traditional Rental Income: $1561 Airbnb ROI: 0.7% Traditional ROI: 5.3%

Your search for investment property begins and ends here

Condos for Sale in Chesapeake, VA

1016 Thoroughgood Way #307

Chesapeake, VA

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

$239,999

Airbnb cash on cash: -0.12%

Traditional cash on cash: 6.55%

Airbnb Rental Income: $818

Traditional Rental Income: $2004

Airbnb ROI: -0.12%

Traditional ROI: 6.55%

801 Poindexter Street #314

Chesapeake, VA

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

$159,500

Airbnb cash on cash: 2.93%

Traditional cash on cash: 8.31%

Airbnb Rental Income: $1237

Traditional Rental Income: $1661

Airbnb ROI: 2.93%

Traditional ROI: 8.31%

1312 Bunker Ridge Arch #B

Chesapeake, VA

3 beds | 2 baths | 1,591 sq.ft.

$325,000

Airbnb cash on cash: 1.14%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $1466

Traditional Rental Income: $2058

Airbnb ROI: 1.14%

Traditional ROI: 4.49%

1016 Thoroughgood Way #101

Chesapeake, VA

2 beds | 2 baths | 1,166 sq.ft.

$230,000

Airbnb cash on cash: -0.08%

Traditional cash on cash: 6.19%

Airbnb Rental Income: $818

Traditional Rental Income: $1856

Airbnb ROI: -0.08%

Traditional ROI: 6.19%

1462 Titchfield Drive

Chesapeake, VA

2 beds | 3 baths | 1,350 sq.ft.

$285,000

Airbnb cash on cash: 0.98%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $1257

Traditional Rental Income: $2027

Airbnb ROI: 0.98%

Traditional ROI: 5.33%

712 Inlet Quay #A

Chesapeake, VA

2 beds | 2 baths | 1,304 sq.ft.

$275,000

Airbnb cash on cash: -0.02%

Traditional cash on cash: 4.8%

Airbnb Rental Income: $960

Traditional Rental Income: $1859

Airbnb ROI: -0.02%

Traditional ROI: 4.8%

902 CENTURION Circle

Chesapeake, VA

3 beds | 3 baths | 1,679 sq.ft.

$419,000

Airbnb cash on cash: -0.24%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $1039

Traditional Rental Income: $2503

Airbnb ROI: -0.24%

Traditional ROI: 4.41%

704 Inlet Quay #J

Chesapeake, VA

3 beds | 2 baths | 1,523 sq.ft.

$295,000

Airbnb cash on cash: 1.38%

Traditional cash on cash: 5.14%

Airbnb Rental Income: $1466

Traditional Rental Income: $2078

Airbnb ROI: 1.38%