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 81 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 Beautifully maintained, one-owner, 3rd-floor condo with elevator access in a secure-entry ...	2 beds \| 2 baths \| 1,255 sq.ft.	$244,500	Airbnb cash on cash: 1.27% Traditional cash on cash: 6.3% Airbnb Rental Income: $1239 Traditional Rental Income: $2004 Airbnb ROI: 1.27% Traditional ROI: 6.3%
717 Inlet Quay #H Chesapeake, VA Move-in ready and ideally located in the heart of Chesapeake! This well-maintained home fe...	2 beds \| 2 baths \| 1,120 sq.ft.	$210,000	Airbnb cash on cash: 2.91% Traditional cash on cash: 5.78% Airbnb Rental Income: $1569 Traditional Rental Income: $1690 Airbnb ROI: 2.91% Traditional ROI: 5.78%
536 Cristfield Road Chesapeake, VA If owning a stunning former model home, with all the bells and whistles, is on your radar....	3 beds \| 3 baths \| 2,003 sq.ft.	$454,500	Airbnb cash on cash: 1.43% Traditional cash on cash: 3.59% Airbnb Rental Income: $2021 Traditional Rental Income: $2412 Airbnb ROI: 1.43% Traditional ROI: 3.59%
801 Poindexter Street #318 Chesapeake, VA Come See This One Level Studio Condo That Offers Comfortable Low Maintenance Living With T...	1 beds \| 1 baths \| 980 sq.ft.	$155,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 8.75% Airbnb Rental Income: $1027 Traditional Rental Income: $1684 Airbnb ROI: 1.88% Traditional ROI: 8.75%
1523 Pucknall Drive Chesapeake, VA Easy living awaits in this 3-bedroom, 2.5-bath condo in the heart of Greenbrier. The livin...	3 beds \| 3 baths \| 1,870 sq.ft.	$349,900	Airbnb cash on cash: 2.37% Traditional cash on cash: 4.54% Airbnb Rental Income: $2021 Traditional Rental Income: $2209 Airbnb ROI: 2.37% Traditional ROI: 4.54%
1317 Eagles Trace Path #E Chesapeake, VA Luxury meets lifestyle on the 10th fairway of Greenbrier Country Club-offering sweeping go...	3 beds \| 3 baths \| 1,707 sq.ft.	$353,800	Airbnb cash on cash: 2.32% Traditional cash on cash: 4.49% Airbnb Rental Income: $2021 Traditional Rental Income: $2217 Airbnb ROI: 2.32% Traditional ROI: 4.49%
706 Albertine Court Chesapeake, VA Beautiful and meticulously cared for open concept, end unit condo located on a quiet cul-d...	3 beds \| 3 baths \| 1,760 sq.ft.	$365,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 4.68% Airbnb Rental Income: $1866 Traditional Rental Income: $2396 Airbnb ROI: 1.68% Traditional ROI: 4.68%
1002 Willow Green Court Chesapeake, VA Located in the Riverwalk section of Chesapeake, this corner unit offers added privacy and ...	2 beds \| 3 baths \| 1,168 sq.ft.	$255,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 6.61% Airbnb Rental Income: $1569 Traditional Rental Income: $2138 Airbnb ROI: 2.37% Traditional ROI: 6.61%
1517 Eagle Glen Drive Chesapeake, VA Welcome home to this beautifully appointed, move-in ready Seafield model in Eagle Pointe, ...	3 beds \| 3 baths \| 2,450 sq.ft.	$539,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 3.78% Airbnb Rental Income: $1947 Traditional Rental Income: $2916 Airbnb ROI: 0.83% Traditional ROI: 3.78%
432 Autumn Green Lane Chesapeake, VA Welcome to your beautifully maintained turn-key dream home in the heart of Chesapeake. Thi...	3 beds \| 3 baths \| 1,804 sq.ft.	$369,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 4.51% Airbnb Rental Income: $1866 Traditional Rental Income: $2323 Airbnb ROI: 1.75% Traditional ROI: 4.51%
4332 Hillingdon Bend #208 Chesapeake, VA Don't miss this great 2nd floor unit. Updates have been done and its ready to go. Close to...	2 beds \| 2 baths \| 1,326 sq.ft.	$229,999	Airbnb cash on cash: 2.59% Traditional cash on cash: 5.7% Airbnb Rental Income: $1522 Traditional Rental Income: $1756 Airbnb ROI: 2.59% Traditional ROI: 5.7%
928 Adventure Way Chesapeake, VA Beautiful end-unit villa in sought-after Bryans Cove and the Grassfield school district. T...	3 beds \| 3 baths \| 2,604 sq.ft.	$469,900	Airbnb cash on cash: 1.08% Traditional cash on cash: 4.06% Airbnb Rental Income: $1947 Traditional Rental Income: $2744 Airbnb ROI: 1.08% Traditional ROI: 4.06%
1615 Thomason Trail Chesapeake, VA Easy living in South-Central Chesapeake ! Just moments from everything you need! This beau...	3 beds \| 3 baths \| 1,810 sq.ft.	$380,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 4.55% Airbnb Rental Income: $2021 Traditional Rental Income: $2409 Airbnb ROI: 1.99% Traditional ROI: 4.55%
1219 Granton Terrace Chesapeake, VA Start packing...this exceptional Westport is the one you've been waiting for! Beautifully ...	3 beds \| 3 baths \| 1,870 sq.ft.	$435,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 3.57% Airbnb Rental Income: $2189 Traditional Rental Income: $2326 Airbnb ROI: 1.87% Traditional ROI: 3.57%
4606 Old Fox Trail Chesapeake, VA Tucked-Away Condo Charm in Western Branch!Located in the back of the community away from t...	3 beds \| 3 baths \| 1,703 sq.ft.	$285,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 5.02% Airbnb Rental Income: $1495 Traditional Rental Income: $1937 Airbnb ROI: 1.74% Traditional ROI: 5.02%
4 Harbor Watch Drive #508 Chesapeake, VA Renovated condo in private waterfront community in the heart of Great Bridge! This beautif...	3 beds \| 2 baths \| 1,762 sq.ft.	$309,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 5.2% Airbnb Rental Income: $2189 Traditional Rental Income: $2175 Airbnb ROI: 3.35% Traditional ROI: 5.2%
1029 Warrington Boulevard Chesapeake, VA Welcome to 1029 Warrington Blvd, a beautifully maintained home nestled in one of Chesapeak...	2 beds \| 3 baths \| 1,624 sq.ft.	$329,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 5.54% Airbnb Rental Income: $1495 Traditional Rental Income: $2336 Airbnb ROI: 1.4% Traditional ROI: 5.54%
1233 Parkley Drive Chesapeake, VA Like-new and beautifully maintained, this phenomenal Chesapeake townhome offers style, spa...	3 beds \| 3 baths \| 1,774 sq.ft.	$378,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 4.2% Airbnb Rental Income: $1866 Traditional Rental Income: $2282 Airbnb ROI: 1.62% Traditional ROI: 4.2%
1513 Braishfield Court Chesapeake, VA Welcome to this beautifully maintained condo featuring two spacious primary suites, each c...	3 beds \| 3 baths \| 1,862 sq.ft.	$335,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 5.44% Airbnb Rental Income: $2021 Traditional Rental Income: $2415 Airbnb ROI: 2.52% Traditional ROI: 5.44%
1601 Thomason Trail Chesapeake, VA Welcome to this exceptional end-unit luxury townhome, original owner bought as the communi...	4 beds \| 3 baths \| 1,994 sq.ft.	$370,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 5.7% Airbnb Rental Income: $2879 Traditional Rental Income: $2677 Airbnb ROI: 4.36% Traditional ROI: 5.7%
1507 Hambledon Loop Chesapeake, VA Beautiful home in the desirable Brighton Park at Greenbrier. Incredible location with mult...	2 beds \| 3 baths \| 1,350 sq.ft.	$282,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 4.86% Airbnb Rental Income: $1495 Traditional Rental Income: $1895 Airbnb ROI: 1.7% Traditional ROI: 4.86%
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: 1.94% Traditional cash on cash: 4.8% Airbnb Rental Income: $1569 Traditional Rental Income: $1859 Airbnb ROI: 1.94% Traditional ROI: 4.8%
2833 Estella Way Chesapeake, VA Welcome to this beautifully maintained townhome in the heart of Chesapeake. This home offe...	3 beds \| 3 baths \| 1,478 sq.ft.	$335,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 4.27% Airbnb Rental Income: $1824 Traditional Rental Income: $2024 Airbnb ROI: 2.07% Traditional ROI: 4.27%
500 Judah Way #123 Chesapeake, VA Gated Community! Elevator! Move in ready for serene living. Bright and modern condo with e...	2 beds \| 2 baths \| 1,215 sq.ft.	$264,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 4.65% Airbnb Rental Income: $1569 Traditional Rental Income: $1741 Airbnb ROI: 2.16% Traditional ROI: 4.65%
4620 Longleaf Place Chesapeake, VA Prepare to fall in love with this Beauty in the 55+ community of Retreat at Western Branch...	4 beds \| 3 baths \| 2,842 sq.ft.	$443,900	Airbnb cash on cash: 1.43% Traditional cash on cash: 4.49% Airbnb Rental Income: $2079 Traditional Rental Income: $2814 Airbnb ROI: 1.43% Traditional ROI: 4.49%
4332 Hillingdon Bend #206 Chesapeake, VA Located in the Western Branch North area of Chesapeake, Virginia, 4332 Hillingdon Bend, Un...	2 beds \| 2 baths \| 1,367 sq.ft.	$239,900	Airbnb cash on cash: 2.44% Traditional cash on cash: 5.9% Airbnb Rental Income: $1522 Traditional Rental Income: $1864 Airbnb ROI: 2.44% Traditional ROI: 5.9%
949 Gabion Way Chesapeake, VA Welcome to 949 Gabion Way, with comfort and style, the first-floor family room is perfectl...	3 beds \| 3 baths \| 2,000 sq.ft.	$400,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 3.56% Airbnb Rental Income: $1947 Traditional Rental Income: $2356 Airbnb ROI: 1.1% Traditional ROI: 3.56%
1601 Mary Lou Lane Chesapeake, VA Welcome to 1601 Mary Lou Ln! Step into effortless living with this beautifully upgraded ho...	3 beds \| 3 baths \| 2,292 sq.ft.	$499,900	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.45% Airbnb Rental Income: $1947 Traditional Rental Income: $2603 Airbnb ROI: 0.95% Traditional ROI: 3.45%
2806 Baldwin Drive Chesapeake, VA Located in one of the most private settings in The Woodlands, this condo offers a spacious...	2 beds \| 3 baths \| 1,314 sq.ft.	$284,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 5.5% Airbnb Rental Income: $1522 Traditional Rental Income: $2085 Airbnb ROI: 1.74% Traditional ROI: 5.5%
503 Nesbit Drive Chesapeake, VA Move-in ready in the Villas at Culpepper Landing! This 1,454 sq ft condo packs 2 bedrooms,...	2 beds \| 3 baths \| 1,456 sq.ft.	$285,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 5.22% Airbnb Rental Income: $1303 Traditional Rental Income: $2093 Airbnb ROI: 0.77% Traditional ROI: 5.22%
4646 Longleaf Place Chesapeake, VA Welcome to easy living in this beautifully upgraded, better than new condo in a vibrant 55...	4 beds \| 3 baths \| 2,842 sq.ft.	$449,900	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.94% Airbnb Rental Income: $2079 Traditional Rental Income: $3036 Airbnb ROI: 1.4% Traditional ROI: 4.94%
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 \| 1,000 sq.ft.	$244,500	Airbnb cash on cash: 1.76% Traditional cash on cash: 4.17% Airbnb Rental Income: $1303 Traditional Rental Income: $1452 Airbnb ROI: 1.76% Traditional ROI: 4.17%
959 Gabion Way Chesapeake, VA This one truly stands apart! Beautiful end-unit opportunity in Bryan's Cove-. Built in 202...	3 beds \| 3 baths \| 2,036 sq.ft.	$440,500	Airbnb cash on cash: 0.87% Traditional cash on cash: 3.24% Airbnb Rental Income: $1947 Traditional Rental Income: $2410 Airbnb ROI: 0.87% Traditional ROI: 3.24%
2 Harbor Watch Drive #718 Chesapeake, VA Welcome to Harbor Watch! This well maintained top floor condo offers 3 bedrooms, 2 full ba...	3 beds \| 2 baths \| 1,764 sq.ft.	$304,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 6.53% Airbnb Rental Income: $1866 Traditional Rental Income: $2513 Airbnb ROI: 2.52% Traditional ROI: 6.53%
301 Sikeston Lane Chesapeake, VA Welcome home to this luxurious 4-bed, 3 full bath home located in the highly sought-after ...	4 beds \| 3 baths \| 2,206 sq.ft.	$449,990	Airbnb cash on cash: -0.18% Traditional cash on cash: 4.16% Airbnb Rental Income: $1240 Traditional Rental Income: $2676 Airbnb ROI: -0.18% Traditional ROI: 4.16%
1808 Aft Way Chesapeake, VA This beautiful tri-level 2-car garage condo in the sought-after Grassfield district offers...	4 beds \| 3 baths \| 2,036 sq.ft.	$400,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 4.46% Airbnb Rental Income: $2107 Traditional Rental Income: $2507 Airbnb ROI: 1.95% Traditional ROI: 4.46%
4605 Woodmark Trail Chesapeake, VA Layout & Design: This highly desirable corner unit boasts extra windows that fill the spac...	3 beds \| 2 baths \| 1,245 sq.ft.	$260,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 5.67% Airbnb Rental Income: $1495 Traditional Rental Income: $1944 Airbnb ROI: 2.05% Traditional ROI: 5.67%
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.	$258,000	Airbnb cash on cash: 2.13% Traditional cash on cash: 5.17% Airbnb Rental Income: $1569 Traditional Rental Income: $1860 Airbnb ROI: 2.13% Traditional ROI: 5.17%
2418 Fieldsway Drive Chesapeake, VA Enjoy stylish, comfortable living in this beautifully maintained Goldenrod model with 3 be...	3 beds \| 3 baths \| 1,739 sq.ft.	$385,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 3.76% Airbnb Rental Income: $1824 Traditional Rental Income: $2149 Airbnb ROI: 1.49% Traditional ROI: 3.76%
1803 Honey Milk Road Chesapeake, VA Enjoy receiving the $41,000 equity Right Away as the recent appraisal value being $510,000...	4 beds \| 4 baths \| 2,177 sq.ft.	$469,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 4.97% Airbnb Rental Income: $2107 Traditional Rental Income: $3125 Airbnb ROI: 1.42% Traditional ROI: 4.97%

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.

$244,500

Airbnb cash on cash: 1.27%

Traditional cash on cash: 6.3%

Airbnb Rental Income: $1239

Traditional Rental Income: $2004

Airbnb ROI: 1.27%

Traditional ROI: 6.3%

717 Inlet Quay #H

Chesapeake, VA

2 beds | 2 baths | 1,120 sq.ft.

$210,000

Airbnb cash on cash: 2.91%

Traditional cash on cash: 5.78%

Airbnb Rental Income: $1569

Traditional Rental Income: $1690

Airbnb ROI: 2.91%

Traditional ROI: 5.78%

536 Cristfield Road

Chesapeake, VA

3 beds | 3 baths | 2,003 sq.ft.

$454,500

Airbnb cash on cash: 1.43%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $2021

Traditional Rental Income: $2412

Airbnb ROI: 1.43%

Traditional ROI: 3.59%

801 Poindexter Street #318

Chesapeake, VA

1 beds | 1 baths | 980 sq.ft.

$155,000

Airbnb cash on cash: 1.88%

Traditional cash on cash: 8.75%

Airbnb Rental Income: $1027

Traditional Rental Income: $1684

Airbnb ROI: 1.88%

Traditional ROI: 8.75%

1523 Pucknall Drive

Chesapeake, VA

3 beds | 3 baths | 1,870 sq.ft.

$349,900

Airbnb cash on cash: 2.37%

Traditional cash on cash: 4.54%

Airbnb Rental Income: $2021

Traditional Rental Income: $2209

Airbnb ROI: 2.37%

Traditional ROI: 4.54%

1317 Eagles Trace Path #E

Chesapeake, VA

3 beds | 3 baths | 1,707 sq.ft.

$353,800

Airbnb cash on cash: 2.32%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $2021

Traditional Rental Income: $2217

Airbnb ROI: 2.32%

Traditional ROI: 4.49%

706 Albertine Court

Chesapeake, VA

3 beds | 3 baths | 1,760 sq.ft.

$365,000

Airbnb cash on cash: 1.68%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $1866

Traditional Rental Income: $2396

Airbnb ROI: 1.68%

Traditional ROI: 4.68%

1002 Willow Green Court

Chesapeake, VA

2 beds | 3 baths | 1,168 sq.ft.

$255,000

Airbnb cash on cash: 2.37%

Traditional cash on cash: 6.61%

Airbnb Rental Income: $1569

Traditional Rental Income: $2138

Airbnb ROI: 2.37%