Real Estate Investment Properties for Sale in Princess Anne, MD

Looking for investment property in Princess Anne, MD with high ROI ?

Explore a variety of short-term homes & houses in Princess Anne, MD. Invest wisely with VRBO & Princess Anne, MD 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 Princess Anne, MD

Search for Single Family Residential for Sale in Princess Anne, Maryland. 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 28 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
10407 William Sharpless Rd Princess Anne, MD This property won't last long!! Over $100,000 reduction in price!!!!Ready for you!! Come a...	4 beds \| 2 baths \| 1,232 sq.ft.	$309,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.22% Airbnb Rental Income: $null Traditional Rental Income: $2304 Airbnb ROI: N/A Traditional ROI: 6.22%
11700 Mansion St Princess Anne, MD Step back in time with this beautifully preserved historic home in the heart of Princess A...	4 beds \| 4 baths \| 5,445 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.74% Airbnb Rental Income: $null Traditional Rental Income: $3407 Airbnb ROI: N/A Traditional ROI: 3.74%
30030 Greenspring Dr Princess Anne, MD Welcome home to 30030 Greenspring Dr! This 3 bedroom 2 bathroom home is waiting for it's n...	3 beds \| 2 baths \| 1,456 sq.ft.	$199,995	Airbnb cash on cash: 8.21% Traditional cash on cash: 7.12% Airbnb Rental Income: $2603 Traditional Rental Income: $1773 Airbnb ROI: 8.21% Traditional ROI: 7.12%
30375 Daphne Ln Princess Anne, MD Beautiful inside-out, located in Hayman Land Community and ready for you to call this your...	4 beds \| 3 baths \| 1,913 sq.ft.	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.68% Airbnb Rental Income: $null Traditional Rental Income: $2860 Airbnb ROI: N/A Traditional ROI: 6.68%
11746 Crisfield Ln Princess Anne, MD Built in 2022 by a local home-builder - 3BR/2BA ranch on a nice-sized lot. Location qualif...	3 beds \| 2 baths \| 1,222 sq.ft.	$269,990	Airbnb cash on cash: 5.59% Traditional cash on cash: 5.81% Airbnb Rental Income: $2603 Traditional Rental Income: $2036 Airbnb ROI: 5.59% Traditional ROI: 5.81%
10590 Rosewood Ct Princess Anne, MD BRAND NEW HOME -- High end finishes throughout! Great location - minutes to Historic Down...	4 beds \| 2 baths \| 2,508 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $2171 Airbnb ROI: N/A Traditional ROI: 3.3%
10373 Locust Point Rd Princess Anne, MD "Almodington" is one of Somerset Counties most elaborate mid-18th Century Georgian Plantat...	5 beds \| 5 baths \| 6,491 sq.ft.	$2,750,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.03% Airbnb Rental Income: $null Traditional Rental Income: $6355 Airbnb ROI: N/A Traditional ROI: 1.03%
30432 Oak St Princess Anne, MD 30432 Oak St, Princess Anne, MD 21853 \| Single Family Residential	4 beds \| 2 baths \| 2,338 sq.ft.	$148,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.32% Airbnb Rental Income: $null Traditional Rental Income: $2001 Airbnb ROI: N/A Traditional ROI: 11.32%
30483 Manor Dr Princess Anne, MD Open layout features kitchen with island. Dining area with sliding door to rear deck. Priv...	3 beds \| 2 baths \| 1,372 sq.ft.	$299,900	Airbnb cash on cash: 4.83% Traditional cash on cash: 4.94% Airbnb Rental Income: $2603 Traditional Rental Income: $2013 Airbnb ROI: 4.83% Traditional ROI: 4.94%
30472 Plantation Dr Princess Anne, MD Welcome to this beautifully maintained home located on a desirable corner lot in the Beckf...	3 beds \| 2 baths \| 1,868 sq.ft.	$345,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 4.15% Airbnb Rental Income: $2603 Traditional Rental Income: $2236 Airbnb ROI: 3.36% Traditional ROI: 4.15%
30090 Kristwood Way Princess Anne, MD 30090 Kristwood Way, Princess Anne, MD 21853 \| Single Family Residential	3 beds \| 2 baths \| 1,296 sq.ft.	$205,000	Airbnb cash on cash: 7.63% Traditional cash on cash: 2.32% Airbnb Rental Income: $2603 Traditional Rental Income: $948 Airbnb ROI: 7.63% Traditional ROI: 2.32%
11691 Beechwood St Princess Anne, MD TURNKEY INVESTMENT OPPORTUNITY in Princess Anne, MD. This well located 2-Unit features two...	5 beds \| 3 baths \| 1,664 sq.ft.	$215,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.95% Airbnb Rental Income: $null Traditional Rental Income: $1378 Airbnb ROI: N/A Traditional ROI: 4.95%
10660 Rosewood Ct Princess Anne, MD 10660 Rosewood Ct, Princess Anne, MD 21853 \| Single Family Residential	3 beds \| 2 baths \| 2,426 sq.ft.	$650,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 1.27% Airbnb Rental Income: $2603 Traditional Rental Income: $2146 Airbnb ROI: 0.99% Traditional ROI: 1.27%
12223 Somerset Ave Princess Anne, MD 12223 Somerset Ave, Princess Anne, MD 21853 \| Single Family Residential	3 beds \| 2 baths \| 1,170 sq.ft.	$250,000	Airbnb cash on cash: 5.92% Traditional cash on cash: 4.91% Airbnb Rental Income: $2603 Traditional Rental Income: $1744 Airbnb ROI: 5.92% Traditional ROI: 4.91%
30555 Skipjack Cir #83 Princess Anne, MD 30555 Skipjack Cir #83, Princess Anne, MD 21853 \| Single Family Residential	3 beds \| 2 baths \| N/A	$297,500	Airbnb cash on cash: 4.66% Traditional cash on cash: 3.47% Airbnb Rental Income: $2603 Traditional Rental Income: $1646 Airbnb ROI: 4.66% Traditional ROI: 3.47%
11726 St Stephens Way Princess Anne, MD Under Construction - Quick Delivery - August 2026! * * * Location Qualifies for 100% Finan...	3 beds \| 2 baths \| 1,300 sq.ft.	$279,990	Airbnb cash on cash: 4.56% Traditional cash on cash: 5.16% Airbnb Rental Income: $2603 Traditional Rental Income: $2137 Airbnb ROI: 4.56% Traditional ROI: 5.16%
27174 Champ Wharf Rd Champ Wharf #27174 Princess Anne, MD MOTIVATED SELLER HOME WARRANTY AVAILABLE WITH ACCEPTED OFFER This home has a recent apprai...	2 beds \| 2 baths \| 1,232 sq.ft.	$299,500	Airbnb cash on cash: 3.76% Traditional cash on cash: 5.4% Airbnb Rental Income: $2182 Traditional Rental Income: $2092 Airbnb ROI: 3.76% Traditional ROI: 5.4%
13460 Harrison Landing Rd Princess Anne, MD 13460 Harrison Landing Rd, Princess Anne, MD 21853 \| Single Family Residential	4 beds \| 3 baths \| 2,055 sq.ft.	$639,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $null Traditional Rental Income: $2308 Airbnb ROI: N/A Traditional ROI: 1.63%
14265 Melody Dr Princess Anne, MD 14265 Melody Dr, Princess Anne, MD 21853 \| Single Family Residential	6 beds \| 3 baths \| 5,617 sq.ft.	$1,920,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.6% Airbnb Rental Income: $null Traditional Rental Income: $2753 Airbnb ROI: N/A Traditional ROI: -0.6%
11950 Drexwood Dr Princess Anne, MD Start your next chapter at 11950 Drexwood Dr! This recently updated 3-bedroom, 2-bath ranc...	3 beds \| 2 baths \| 934 sq.ft.	$173,000	Airbnb cash on cash: 9.61% Traditional cash on cash: 7.81% Airbnb Rental Income: $2603 Traditional Rental Income: $1683 Airbnb ROI: 9.61% Traditional ROI: 7.81%
27093 Point Rd Princess Anne, MD Waterfront living at its finest! This 3-bedroom 2-bath A-frame home is perfectly situated ...	3 beds \| 2 baths \| 1,400 sq.ft.	$367,999	Airbnb cash on cash: 3.57% Traditional cash on cash: 2.76% Airbnb Rental Income: $2603 Traditional Rental Income: $1701 Airbnb ROI: 3.57% Traditional ROI: 2.76%
29523 Polks Rd Princess Anne, MD Tucked away on 5 private acres, this spacious 5-bedroom, 3-bath home offers the fl...	5 beds \| 3 baths \| 2,250 sq.ft.	$374,990	Airbnb cash on cash: N/A Traditional cash on cash: 5.64% Airbnb Rental Income: $null Traditional Rental Income: $2591 Airbnb ROI: N/A Traditional ROI: 5.64%
11708 Robyn Ln Princess Anne, MD Looking for a Unique home? How about, The Cool Octagon House in Princess Anne? Open Concep...	1 beds \| 1 baths \| 694 sq.ft.	$122,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.9% Airbnb Rental Income: $null Traditional Rental Income: $1584 Airbnb ROI: N/A Traditional ROI: 10.9%
29728 Mount Vernon Rd Princess Anne, MD Mt. Vernon Road Farm is a 33.46-acre farm located just outside Princess Anne in Somerset C...	3 beds \| 1 baths \| 1,296 sq.ft.	$525,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 2.33% Airbnb Rental Income: $2603 Traditional Rental Income: $1846 Airbnb ROI: 2.6% Traditional ROI: 2.33%
10710 Rosewood Ct Princess Anne, MD 10710 Rosewood Ct, Princess Anne, MD 21853 \| Single Family Residential	4 beds \| 3 baths \| 2,950 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.66% Airbnb Rental Income: $null Traditional Rental Income: $2774 Airbnb ROI: N/A Traditional ROI: 2.66%
31008 Peggy Neck Rd Princess Anne, MD 31008 Peggy Neck Rd, Princess Anne, MD 21853 \| Single Family Residential	3 beds \| 1 baths \| 880 sq.ft.	$295,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 3.08% Airbnb Rental Income: $2603 Traditional Rental Income: $1525 Airbnb ROI: 4.71% Traditional ROI: 3.08%
11395 Hayman Dr Princess Anne, MD 11395 Hayman Dr, Princess Anne, MD 21853 \| Single Family Residential	4 beds \| 2 baths \| 2,126 sq.ft.	$479,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.17% Airbnb Rental Income: $null Traditional Rental Income: $2001 Airbnb ROI: N/A Traditional ROI: 2.17%

Your search for investment property begins and ends here

Single Family Homes for Sale in Princess Anne, MD

10407 William Sharpless Rd

Princess Anne, MD

4 beds | 2 baths | 1,232 sq.ft.

$309,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.22%

Airbnb Rental Income: $null

Traditional Rental Income: $2304

Airbnb ROI: N/A

Traditional ROI: 6.22%

11700 Mansion St

Princess Anne, MD

4 beds | 4 baths | 5,445 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.74%

Airbnb Rental Income: $null

Traditional Rental Income: $3407

Airbnb ROI: N/A

Traditional ROI: 3.74%

30030 Greenspring Dr

Princess Anne, MD

3 beds | 2 baths | 1,456 sq.ft.

$199,995

Airbnb cash on cash: 8.21%

Traditional cash on cash: 7.12%

Airbnb Rental Income: $2603

Traditional Rental Income: $1773

Airbnb ROI: 8.21%

Traditional ROI: 7.12%

30375 Daphne Ln

Princess Anne, MD

4 beds | 3 baths | 1,913 sq.ft.

$359,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.68%

Airbnb Rental Income: $null

Traditional Rental Income: $2860

Airbnb ROI: N/A

Traditional ROI: 6.68%

11746 Crisfield Ln

Princess Anne, MD

3 beds | 2 baths | 1,222 sq.ft.

$269,990

Airbnb cash on cash: 5.59%

Traditional cash on cash: 5.81%

Airbnb Rental Income: $2603

Traditional Rental Income: $2036

Airbnb ROI: 5.59%

Traditional ROI: 5.81%

10590 Rosewood Ct

Princess Anne, MD

4 beds | 2 baths | 2,508 sq.ft.

$449,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.3%

Airbnb Rental Income: $null

Traditional Rental Income: $2171

Airbnb ROI: N/A

Traditional ROI: 3.3%

10373 Locust Point Rd

Princess Anne, MD

5 beds | 5 baths | 6,491 sq.ft.

$2,750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.03%

Airbnb Rental Income: $null

Traditional Rental Income: $6355

Airbnb ROI: N/A

Traditional ROI: 1.03%

30432 Oak St

Princess Anne, MD

4 beds | 2 baths | 2,338 sq.ft.

$148,900

Airbnb cash on cash: N/A

Traditional cash on cash: 11.32%

Airbnb Rental Income: $null

Traditional Rental Income: $2001

Airbnb ROI: N/A