Real Estate Investment Properties for Sale in Portsmouth, VA

Looking for investment property in Portsmouth, VA with high ROI ?

Explore a variety of short-term homes & houses in Portsmouth, VA. Invest wisely with VRBO & Portsmouth, 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 Portsmouth, VA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1511 Cavalier Boulevard Portsmouth, VA Nice brick ranch with 3 bedrooms, 2 full baths and open floor plan. Renovated about 5 year...	3 beds \| 2 baths \| 1,332 sq.ft.	$271,900	Airbnb cash on cash: 2.54% Traditional cash on cash: 4.23% Airbnb Rental Income: $1745 Traditional Rental Income: $1700 Airbnb ROI: 2.54% Traditional ROI: 4.23%
6200 Arthur Avenue Portsmouth, VA Seller is offering closing cost assistance on this beautiful like-new 4 bedroom and 2.5 ba...	4 beds \| 3 baths \| 2,400 sq.ft.	$409,900	Airbnb cash on cash: -0.28% Traditional cash on cash: 4.21% Airbnb Rental Income: $1189 Traditional Rental Income: $2526 Airbnb ROI: -0.28% Traditional ROI: 4.21%
475 Water ST Portsmouth, VA Waterfront living at it's finest in Admiral's Landing, boasting two private balconies and ...	2 beds \| 3 baths \| N/A	$312,500	Airbnb cash on cash: 0.06% Traditional cash on cash: 4.47% Airbnb Rental Income: $1133 Traditional Rental Income: $2051 Airbnb ROI: 0.06% Traditional ROI: 4.47%
5701 Hawthorne Lane Portsmouth, VA Beautifully maintained brick rancher offering a newly fenced spacious .40 acre corner lot....	4 beds \| 2 baths \| 1,638 sq.ft.	$350,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 4.04% Airbnb Rental Income: $1654 Traditional Rental Income: $2104 Airbnb ROI: 1.26% Traditional ROI: 4.04%
3304 Winchester Drive Portsmouth, VA This beautiful 4 bedroom 2 bathroom home is waiting for you! Newley renovated with in the ...	4 beds \| 2 baths \| 1,208 sq.ft.	$270,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 5.08% Airbnb Rental Income: $2124 Traditional Rental Income: $1882 Airbnb ROI: 3.9% Traditional ROI: 5.08%
215 Webster Avenue Portsmouth, VA Come take a step into the kind of homeownership dream you've been waiting for-where timele...	4 beds \| 3 baths \| 2,400 sq.ft.	$360,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 6.43% Airbnb Rental Income: $2079 Traditional Rental Income: $2948 Airbnb ROI: 2.27% Traditional ROI: 6.43%
4013 Timberland Drive Portsmouth, VA Come see this wonderful 4-bedroom, 2-bathroom home located in the Merrifields neighborhood...	4 beds \| 2 baths \| 1,804 sq.ft.	$360,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 3.97% Airbnb Rental Income: $1654 Traditional Rental Income: $2119 Airbnb ROI: 1.22% Traditional ROI: 3.97%
88 Aylwin Road Portsmouth, VA Change your life with this three-bedroom home in Portsmouth, VA, offering a practical layo...	3 beds \| 1 baths \| 1,602 sq.ft.	$249,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 4.33% Airbnb Rental Income: $1727 Traditional Rental Income: $1647 Airbnb ROI: 2.65% Traditional ROI: 4.33%
3733 Linnet Lane Portsmouth, VA Beautifully maintained home in a well-established neighborhood offering 4 bedrooms and 2 f...	4 beds \| 2 baths \| 1,508 sq.ft.	$345,000	Airbnb cash on cash: 1% Traditional cash on cash: 3.83% Airbnb Rental Income: $1540 Traditional Rental Income: $2009 Airbnb ROI: 1% Traditional ROI: 3.83%
111 High Street #407 Portsmouth, VA Welcome to Crawford Square Condominiums! This beautiful move-in ready, condo is located in...	2 beds \| 2 baths \| 1,073 sq.ft.	$189,900	Airbnb cash on cash: 1.68% Traditional cash on cash: 6.42% Airbnb Rental Income: $1133 Traditional Rental Income: $1611 Airbnb ROI: 1.68% Traditional ROI: 6.42%
2309 Leckie Street Portsmouth, VA Charming 3 bedroom/1 bath home with huge yard! Located in the quiet, tucked away neighborh...	3 beds \| 1 baths \| 1,244 sq.ft.	$250,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 3.83% Airbnb Rental Income: $1487 Traditional Rental Income: $1475 Airbnb ROI: 2.03% Traditional ROI: 3.83%
403 Holloway Drive Portsmouth, VA Absolutely Stunning, no other way to put it! Come see this beautiful Ranch style home with...	4 beds \| 3 baths \| 3,291 sq.ft.	$499,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 4.1% Airbnb Rental Income: $2751 Traditional Rental Income: $2978 Airbnb ROI: 2.23% Traditional ROI: 4.1%
3800 Augustine Circle Portsmouth, VA Freshly rehabbed in spring 2026. New flooring in living room, hall and bedrooms. New appli...	3 beds \| 2 baths \| 1,200 sq.ft.	$249,500	Airbnb cash on cash: 1.94% Traditional cash on cash: 4.88% Airbnb Rental Income: $1431 Traditional Rental Income: $1695 Airbnb ROI: 1.94% Traditional ROI: 4.88%
646 Douglas Avenue Portsmouth, VA Beautiful 4-bedroom Victorian home blending historic charm with modern comforts. Situated ...	4 beds \| 2 baths \| 1,960 sq.ft.	$249,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 7.28% Airbnb Rental Income: $2079 Traditional Rental Income: $2368 Airbnb ROI: 3.78% Traditional ROI: 7.28%
161 Maryland Avenue Portsmouth, VA This charming home is full of character and unique features, from the original stained gla...	3 beds \| 3 baths \| 2,625 sq.ft.	$300,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 5.52% Airbnb Rental Income: $1710 Traditional Rental Income: $2303 Airbnb ROI: 1.74% Traditional ROI: 5.52%
258 Broad Street Portsmouth, VA Don't miss this opportunity to move into this charming historic Colonial home with beautif...	3 beds \| 3 baths \| 2,124 sq.ft.	$314,900	Airbnb cash on cash: 1.75% Traditional cash on cash: 4.12% Airbnb Rental Income: $1710 Traditional Rental Income: $1938 Airbnb ROI: 1.75% Traditional ROI: 4.12%
86 Wyoming Avenue Portsmouth, VA THIS 4 BEDROOM 2 BATHROOM HOME HAS A SPACIOUS OPEN FLOOR PLAN, BONUS ROOM FOR AN OFFICE OR...	4 beds \| 2 baths \| 1,772 sq.ft.	$275,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 6.23% Airbnb Rental Income: $2613 Traditional Rental Income: $2275 Airbnb ROI: 5.12% Traditional ROI: 6.23%
107 Beazley Drive Portsmouth, VA Welcome to your charming new home in the sought-after Bide-A-Wee community! This beautiful...	3 beds \| 1 baths \| 950 sq.ft.	$250,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 4.4% Airbnb Rental Income: $1745 Traditional Rental Income: $1603 Airbnb ROI: 2.97% Traditional ROI: 4.4%
48 Gillis Road Portsmouth, VA Situated on a large corner lot, this 3-bedroom, 2-bath, two-story home offers a rare combi...	3 beds \| 2 baths \| 1,492 sq.ft.	$221,000	Airbnb cash on cash: 3.31% Traditional cash on cash: 6.11% Airbnb Rental Income: $1727 Traditional Rental Income: $1836 Airbnb ROI: 3.31% Traditional ROI: 6.11%
407 Sussex Drive Portsmouth, VA Nestled in one of Portsmouth's most desirable historic neighborhoods, this beautifully mai...	3 beds \| 2 baths \| 2,164 sq.ft.	$375,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.74% Airbnb Rental Income: $1439 Traditional Rental Income: $2104 Airbnb ROI: 0.64% Traditional ROI: 3.74%
913 Halifax Avenue Portsmouth, VA Investor alert - this is the opportunity you've been waiting for! Unlock the potential of ...	3 beds \| 1 baths \| 1,739 sq.ft.	$190,000	Airbnb cash on cash: 4.95% Traditional cash on cash: 7.03% Airbnb Rental Income: $1811 Traditional Rental Income: $1695 Airbnb ROI: 4.95% Traditional ROI: 7.03%
88 Paul Jones Street Portsmouth, VA	N/A beds \| N/A baths \| 2,200 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 3% Airbnb Rental Income: $null Traditional Rental Income: $1357 Airbnb ROI: N/A Traditional ROI: 3%
4904 Holly Road Portsmouth, VA Tucked in desirable Castle Heights, this charming home blends classic character with smart...	3 beds \| 3 baths \| 1,458 sq.ft.	$329,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 5.29% Airbnb Rental Income: $1211 Traditional Rental Income: $2252 Airbnb ROI: 0.66% Traditional ROI: 5.29%
475 Water Street #302 Portsmouth, VA Welcome to Admirals Landing and luxury waterfront living in the heart of Olde Towne Portsm...	2 beds \| 2 baths \| 1,271 sq.ft.	$360,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 2.83% Airbnb Rental Income: $1133 Traditional Rental Income: $1759 Airbnb ROI: -0.14% Traditional ROI: 2.83%
4405 Wake Forest Road Portsmouth, VA Beautiful 4-bedroom, 2-bath home in the Pinehurst community! Featuring hardwood floors thr...	4 beds \| 2 baths \| 1,858 sq.ft.	$359,900	Airbnb cash on cash: 0.55% Traditional cash on cash: 3.62% Airbnb Rental Income: $1402 Traditional Rental Income: $2018 Airbnb ROI: 0.55% Traditional ROI: 3.62%
124 Armstrong Street Portsmouth, VA Tucked along a tranquil street, this home delivers curb appeal and modern upgrades. Warm n...	3 beds \| 3 baths \| 2,000 sq.ft.	$369,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 5.29% Airbnb Rental Income: $1487 Traditional Rental Income: $2718 Airbnb ROI: 0.48% Traditional ROI: 5.29%
301 Douglas Avenue Portsmouth, VA Step into this charming two-story traditional home located just minutes from the beautiful...	3 beds \| 1 baths \| 1,593 sq.ft.	$275,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.79% Airbnb Rental Income: $1710 Traditional Rental Income: $1625 Airbnb ROI: 2.29% Traditional ROI: 3.79%
2 Park Manor Road Portsmouth, VA Welcome to the charming, waterfront community of Park Manor. This beautiful property is lo...	3 beds \| 2 baths \| 1,752 sq.ft.	$349,900	Airbnb cash on cash: 1.47% Traditional cash on cash: 4.73% Airbnb Rental Income: $1685 Traditional Rental Income: $2286 Airbnb ROI: 1.47% Traditional ROI: 4.73%
2605 Roanoke Avenue Portsmouth, VA Welcome to this charming 3 bedroom, 2 bath home featuring a versatile bonus room perfect f...	3 beds \| 2 baths \| 1,910 sq.ft.	$285,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 4.34% Airbnb Rental Income: $1595 Traditional Rental Income: $1795 Airbnb ROI: 1.9% Traditional ROI: 4.34%
363 London Street Portsmouth, VA Well maintained, freshly painted and a new carpet condominium in a gated condo community w...	2 beds \| 2 baths \| 1,200 sq.ft.	$223,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 4.97% Airbnb Rental Income: $1133 Traditional Rental Income: $1570 Airbnb ROI: 1.11% Traditional ROI: 4.97%
207 Ivey Street Portsmouth, VA This 5 Bedroom 3-Full-Bath Property Checks All the Boxes. Each Room Is Spacious and Design...	5 beds \| 3 baths \| 2,528 sq.ft.	$375,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 4.93% Airbnb Rental Income: $2440 Traditional Rental Income: $2611 Airbnb ROI: 2.75% Traditional ROI: 4.93%
14 Sandie Point Lane Portsmouth, VA Come and enjoy this lock up and float away lifestyle with this marvelous multi-level conte...	3 beds \| 3 baths \| 2,263 sq.ft.	$364,900	Airbnb cash on cash: 1.28% Traditional cash on cash: 5.14% Airbnb Rental Income: $1685 Traditional Rental Income: $2535 Airbnb ROI: 1.28% Traditional ROI: 5.14%
2 Carver Circle Portsmouth, VA REMODELED, NEW BATHROOM VANITIES, NEW GRANITE KITCHEN COUNTER TOPS, NEW FLOORS, NEW FIXTUR...	3 beds \| 2 baths \| 1,640 sq.ft.	$279,900	Airbnb cash on cash: 2.22% Traditional cash on cash: 4.85% Airbnb Rental Income: $1682 Traditional Rental Income: $1906 Airbnb ROI: 2.22% Traditional ROI: 4.85%
1 Crawford Parkway #1206 Portsmouth, VA Welcome to waterfront living at its finest. Nestled steps away from the Tidewater Yacht Ma...	2 beds \| 2 baths \| 1,070 sq.ft.	$140,000	Airbnb cash on cash: 2.8% Traditional cash on cash: 7.66% Airbnb Rental Income: $1133 Traditional Rental Income: $1408 Airbnb ROI: 2.8% Traditional ROI: 7.66%
1612 Prentis Avenue Portsmouth, VA Discover this modern 3-bed, 3-bath home built in 2019, offering comfortable two-story livi...	3 beds \| 3 baths \| 1,643 sq.ft.	$315,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 4.45% Airbnb Rental Income: $1595 Traditional Rental Income: $2060 Airbnb ROI: 1.35% Traditional ROI: 4.45%
1 Crawford Parkway #1306 Portsmouth, VA Carefree living at its best in Olde Towne! You're going to love this beautifully updated, ...	2 beds \| 2 baths \| 1,015 sq.ft.	$179,900	Airbnb cash on cash: 1.69% Traditional cash on cash: 4.58% Airbnb Rental Income: $1072 Traditional Rental Income: $1199 Airbnb ROI: 1.69% Traditional ROI: 4.58%
4019 Garwood Avenue Portsmouth, VA 4BR/1.5BA ranch situated on an approx. 0.51-acre lot in an established Portsmouth neighbor...	4 beds \| 2 baths \| 1,600 sq.ft.	$249,900	Airbnb cash on cash: 6.95% Traditional cash on cash: 6.35% Airbnb Rental Income: $2858 Traditional Rental Income: $2050 Airbnb ROI: 6.95% Traditional ROI: 6.35%
207 CHEROKEE RD Portsmouth, VA Invest with success and buy through Auction.com. This bank-owned investment property is a ...	4 beds \| 2 baths \| 1,664 sq.ft.	$323,000	Airbnb cash on cash: 4.39% Traditional cash on cash: 4.67% Airbnb Rental Income: $2613 Traditional Rental Income: $2074 Airbnb ROI: 4.39% Traditional ROI: 4.67%
1600 Prentis Avenue Portsmouth, VA Come step into this beautifully restored Victorian-style home, where timeless old-world ch...	3 beds \| 2 baths \| 1,790 sq.ft.	$224,999	Airbnb cash on cash: 3.38% Traditional cash on cash: 7.06% Airbnb Rental Income: $1595 Traditional Rental Income: $1924 Airbnb ROI: 3.38% Traditional ROI: 7.06%
1651 Darren Circle Portsmouth, VA Very well maintained. Tenant is very cooperative and pays $1200.00 a month.	2 beds \| 1 baths \| 946 sq.ft.	$105,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 8.61% Airbnb Rental Income: $1126 Traditional Rental Income: $1175 Airbnb ROI: 4.43% Traditional ROI: 8.61%

Real Estate investment in Portsmouth, VA

There are 258 properties for sale in the city of Portsmouth . The median list price in Portsmouth is $284,853 and the average price per square foot is $178. In June 2026, the average monthly cash on cash return in Portsmouth is 5.00%. The average monthly rental income in Portsmouth is $1,904.

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

There are 258 investment properties available for sale in Portsmouth.

In 2026, the best neighborhood to buy investment property is Hattonsville.

The ROI for Long-Term is higher than the Short-Term in Portsmouth with average rental income of $1,904.

Your search for investment property begins and ends here

Investment Property for Sale in Portsmouth, VA

1511 Cavalier Boulevard

Portsmouth, VA

3 beds | 2 baths | 1,332 sq.ft.

$271,900

Airbnb cash on cash: 2.54%

Traditional cash on cash: 4.23%

Airbnb Rental Income: $1745

Traditional Rental Income: $1700

Airbnb ROI: 2.54%

Traditional ROI: 4.23%

6200 Arthur Avenue

Portsmouth, VA

4 beds | 3 baths | 2,400 sq.ft.

$409,900

Airbnb cash on cash: -0.28%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $1189

Traditional Rental Income: $2526

Airbnb ROI: -0.28%

Traditional ROI: 4.21%

475 Water ST

Portsmouth, VA

2 beds | 3 baths | N/A

$312,500

Airbnb cash on cash: 0.06%

Traditional cash on cash: 4.47%

Airbnb Rental Income: $1133

Traditional Rental Income: $2051

Airbnb ROI: 0.06%

Traditional ROI: 4.47%

5701 Hawthorne Lane

Portsmouth, VA

4 beds | 2 baths | 1,638 sq.ft.

$350,000

Airbnb cash on cash: 1.26%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $1654

Traditional Rental Income: $2104

Airbnb ROI: 1.26%

Traditional ROI: 4.04%

3304 Winchester Drive

Portsmouth, VA

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

$270,000

Airbnb cash on cash: 3.9%

Traditional cash on cash: 5.08%

Airbnb Rental Income: $2124

Traditional Rental Income: $1882

Airbnb ROI: 3.9%

Traditional ROI: 5.08%

215 Webster Avenue

Portsmouth, VA

4 beds | 3 baths | 2,400 sq.ft.

$360,000

Airbnb cash on cash: 2.27%

Traditional cash on cash: 6.43%

Airbnb Rental Income: $2079

Traditional Rental Income: $2948

Airbnb ROI: 2.27%

Traditional ROI: 6.43%

4013 Timberland Drive

Portsmouth, VA

4 beds | 2 baths | 1,804 sq.ft.

$360,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 3.97%

Airbnb Rental Income: $1654

Traditional Rental Income: $2119

Airbnb ROI: 1.22%

Traditional ROI: 3.97%

88 Aylwin Road

Portsmouth, VA

3 beds | 1 baths | 1,602 sq.ft.

$249,900

Airbnb cash on cash: 2.65%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $1727

Traditional Rental Income: $1647

Airbnb ROI: 2.65%