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.

Investment Property for Sale in Princess Anne, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1708 MCCULLOH Street Princess Anne, MD For investors seeking a property with solid cash flow, strong rental demand, and limited i...	N/A beds \| N/A baths \| 4,000 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.64% Airbnb Rental Income: $null Traditional Rental Income: $1515 Airbnb ROI: N/A Traditional ROI: 0.64%
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%
11230 Gail Dr Princess Anne, MD Check out this amazing house located in Princess Anne. This home has everything you could ...	3 beds \| 2 baths \| 1,845 sq.ft.	$320,000	Airbnb cash on cash: 4.15% Traditional cash on cash: 3.99% Airbnb Rental Income: $2603 Traditional Rental Income: $1934 Airbnb ROI: 4.15% Traditional ROI: 3.99%
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.	$354,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.79% Airbnb Rental Income: $null Traditional Rental Income: $2860 Airbnb ROI: N/A Traditional ROI: 6.79%
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%
11502 Beckford Ave Princess Anne, MD Well-maintained licensed duplexperfect for investors, first-time home buyers, or house hac...	4 beds \| 2 baths \| 1,698 sq.ft.	$210,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.9% Airbnb Rental Income: $null Traditional Rental Income: $1555 Airbnb ROI: N/A Traditional ROI: 5.9%
12465 Mallard Ln Princess Anne, MD 12465 Mallard Ln, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$120,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.57% Airbnb Rental Income: $null Traditional Rental Income: $862 Airbnb ROI: N/A Traditional ROI: 4.57%
30471 Manor Dr Princess Anne, MD 30471 Manor Dr, Princess Anne, MD 21853 \| Townhouse	3 beds \| 2 baths \| 1,386 sq.ft.	$247,999	Airbnb cash on cash: 5.27% Traditional cash on cash: 3.78% Airbnb Rental Income: $2603 Traditional Rental Income: $1632 Airbnb ROI: 5.27% Traditional ROI: 3.78%
0 Follow Ditch Rd Princess Anne, MD 0 Follow Ditch Rd, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$2,488,500	Airbnb cash on cash: N/A Traditional cash on cash: -1.86% Airbnb Rental Income: $null Traditional Rental Income: $608 Airbnb ROI: N/A Traditional ROI: -1.86%
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%
12485 Mallard Ln Princess Anne, MD 12485 Mallard Ln, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$120,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.41% Airbnb Rental Income: $null Traditional Rental Income: $862 Airbnb ROI: N/A Traditional ROI: 4.41%
11229 Stewart Neck Rd Princess Anne, MD 11229 Stewart Neck Rd, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| N/A	$1,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.71% Airbnb Rental Income: $null Traditional Rental Income: $608 Airbnb ROI: N/A Traditional ROI: -1.71%
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%
0 Champ Rd Princess Anne, MD 0 Champ Rd, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| N/A	$79,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.41% Airbnb Rental Income: $null Traditional Rental Income: $678 Airbnb ROI: N/A Traditional ROI: 5.41%
30750 Park Dr Princess Anne, MD 30750 Park Dr, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| N/A	$260,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.32% Airbnb Rental Income: $null Traditional Rental Income: $682 Airbnb ROI: N/A Traditional ROI: 0.32%
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%
30416 Plantation Dr Princess Anne, MD 30416 Plantation Dr, Princess Anne, MD 21853 \| Townhouse	3 beds \| 2 baths \| 1,386 sq.ft.	$249,800	Airbnb cash on cash: 5.14% Traditional cash on cash: 3.64% Airbnb Rental Income: $2603 Traditional Rental Income: $1625 Airbnb ROI: 5.14% Traditional ROI: 3.64%
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%
0 Deal Island Rd Princess Anne, MD 0 Deal Island Rd, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| N/A	$94,250	Airbnb cash on cash: N/A Traditional cash on cash: 4.29% Airbnb Rental Income: $null Traditional Rental Income: $678 Airbnb ROI: N/A Traditional ROI: 4.29%
29550 Deal Island Rd Princess Anne, MD Bring your vision to this spacious 3 bed, 2 bath home offering nearly 2,300 sq ft on 1.75 ...	3 beds \| 2 baths \| 2,298 sq.ft.	$299,900	Airbnb cash on cash: 5% Traditional cash on cash: 7.36% Airbnb Rental Income: $2603 Traditional Rental Income: $2645 Airbnb ROI: 5% Traditional ROI: 7.36%
28215 Merlin Ct Princess Anne, MD 28215 Merlin Ct, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| N/A	$95,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.18% Airbnb Rental Income: $null Traditional Rental Income: $690 Airbnb ROI: N/A Traditional ROI: 4.18%
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%
30124 PEGGY Lane Princess Anne, MD Motivated seller, all reasonable offers will be considered. CITY SERVICES WITH NO CI...	3 beds \| 3 baths \| 2,296 sq.ft.	$395,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 3.5% Airbnb Rental Income: $2603 Traditional Rental Income: $2036 Airbnb ROI: 3.35% Traditional ROI: 3.5%
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%
30380 Park Dr Princess Anne, MD 30380 Park Dr, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| N/A	$100,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.17% Airbnb Rental Income: $null Traditional Rental Income: $700 Airbnb ROI: N/A Traditional ROI: 4.17%
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.	$349,990	Airbnb cash on cash: N/A Traditional cash on cash: 6.11% Airbnb Rental Income: $null Traditional Rental Income: $2591 Airbnb ROI: N/A Traditional ROI: 6.11%
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%

Real Estate investment in Princess-anne, MD

There are 47 properties for sale in the city of Princess Anne . The median list price in Princess Anne is $275,835 and the average price per square foot is $164. In September 2026, the average monthly cash on cash return in Princess Anne is 5.00%. The average monthly rental income in Princess Anne is $1,692.

Princess-anne, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 47 investment properties available for sale in Princess-anne.

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

The ROI for Short-Term is higher than the Long-Term in Princess-anne with average rental income of $2,603.

Your search for investment property begins and ends here

Investment Property for Sale in Princess Anne, MD

1708 MCCULLOH Street

Princess Anne, MD

N/A beds | N/A baths | 4,000 sq.ft.

$585,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.64%

Airbnb Rental Income: $null

Traditional Rental Income: $1515

Airbnb ROI: N/A

Traditional ROI: 0.64%

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%

11230 Gail Dr

Princess Anne, MD

3 beds | 2 baths | 1,845 sq.ft.

$320,000

Airbnb cash on cash: 4.15%

Traditional cash on cash: 3.99%

Airbnb Rental Income: $2603

Traditional Rental Income: $1934

Airbnb ROI: 4.15%

Traditional ROI: 3.99%

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.

$354,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.79%

Airbnb Rental Income: $null

Traditional Rental Income: $2860

Airbnb ROI: N/A

Traditional ROI: 6.79%

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