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
11635 Dennis Dr Princess Anne, MD Pride of Ownership awaits our future buyer. Central air, propane heat and a cozy fireplac...	3 beds \| 2 baths \| 1,658 sq.ft.	$285,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 3.76% Airbnb Rental Income: $1396 Traditional Rental Income: $1835 Airbnb ROI: 0.55% Traditional ROI: 3.76%
11619 Somerset Ave Princess Anne, MD Step into a piece of history with this beautifully preserved and thoughtfully updated resi...	3 beds \| 2 baths \| 2,656 sq.ft.	$292,900	Airbnb cash on cash: 1.55% Traditional cash on cash: 7.35% Airbnb Rental Income: $1396 Traditional Rental Income: $2575 Airbnb ROI: 1.55% Traditional ROI: 7.35%
11679 Beckford Ave Princess Anne, MD Built in 2024, this beautiful, BETTER THAN NEW, 3-bedroom, 2.5-bath home offers the perfec...	3 beds \| 2 baths \| 1,352 sq.ft.	$267,900	Airbnb cash on cash: 1.67% Traditional cash on cash: 7.42% Airbnb Rental Income: $1396 Traditional Rental Income: $2425 Airbnb ROI: 1.67% Traditional ROI: 7.42%
30500 Valentine Dr Princess Anne, MD Adorable 3 bedrooms and 1 1/2 bathroom totally remolded on 2021 from hardwood floor to new...	3 beds \| 1 baths \| 1,152 sq.ft.	$189,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 8.31% Airbnb Rental Income: $1396 Traditional Rental Income: $1864 Airbnb ROI: 3.35% Traditional ROI: 8.31%
11075 Jerusalem Rd Princess Anne, MD Looking for acreage and a large garage outside of town? Look no further-opportunities like...	3 beds \| 2 baths \| 1,490 sq.ft.	$305,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 5.37% Airbnb Rental Income: $1396 Traditional Rental Income: $2071 Airbnb ROI: 1.55% Traditional ROI: 5.37%
11378 HAYMAN Drive Princess Anne, MD Welcome to this charming 3-bedroom, 2-bathroom home in Princess Anne, MD, offering beautif...	3 beds \| 2 baths \| 1,858 sq.ft.	$349,900	Airbnb cash on cash: 0.97% Traditional cash on cash: 5.33% Airbnb Rental Income: $1396 Traditional Rental Income: $2405 Airbnb ROI: 0.97% Traditional ROI: 5.33%
11410 Hayman Dr Princess Anne, MD Bring your paint and carpet selections to finish off this fantastic opportunity for someon...	3 beds \| 2 baths \| 1,665 sq.ft.	$274,995	Airbnb cash on cash: 1.58% Traditional cash on cash: 6.52% Airbnb Rental Income: $1396 Traditional Rental Income: $2256 Airbnb ROI: 1.58% Traditional ROI: 6.52%
32792 W POST OFFICE RD Princess Anne, MD Privacy and country living is yours yet close to Somerset, Wicomico and Worcester Counties...	3 beds \| 2 baths \| N/A	$145,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 11.16% Airbnb Rental Income: $1396 Traditional Rental Income: $1945 Airbnb ROI: 4.17% Traditional ROI: 11.16%
27068 Annie Hyland Rd Princess Anne, MD To be built! Construction to begin once a contract is accepted. Find your dream home on pi...	3 beds \| 2 baths \| 1,250 sq.ft.	$499,900	Airbnb cash on cash: 0.48% Traditional cash on cash: 3.06% Airbnb Rental Income: $1396 Traditional Rental Income: $2183 Airbnb ROI: 0.48% Traditional ROI: 3.06%
30564 Blue Jay Cir Princess Anne, MD Check out this beautiful, brand new home located in the Wilson Landing community. This lin...	3 beds \| 2 baths \| 1,232 sq.ft.	$154,995	Airbnb cash on cash: 3.75% Traditional cash on cash: 11.9% Airbnb Rental Income: $1396 Traditional Rental Income: $2220 Airbnb ROI: 3.75% Traditional ROI: 11.9%
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%
27421 Mount Vernon Rd Princess Anne, MD 27421 Mount Vernon Rd, Princess Anne, MD 21853 \| Single Family Residential	4 beds \| 2 baths \| 1,479 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.25% Airbnb Rental Income: $null Traditional Rental Income: $1799 Airbnb ROI: N/A Traditional ROI: 2.25%
30471 Manor Dr Princess Anne, MD 30471 Manor Dr, Princess Anne, MD 21853 \| Townhouse	3 beds \| 2 baths \| 1,386 sq.ft.	$269,900	Airbnb cash on cash: 0.7% Traditional cash on cash: 3.25% Airbnb Rental Income: $1396 Traditional Rental Income: $1632 Airbnb ROI: 0.7% Traditional ROI: 3.25%
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%
26388 Mount Vernon Rd Princess Anne, MD 26388 Mount Vernon Rd, Princess Anne, MD 21853 \| Single Family Residential	3 beds \| 2 baths \| 1,512 sq.ft.	$499,900	Airbnb cash on cash: -0.2% Traditional cash on cash: 1.45% Airbnb Rental Income: $1396 Traditional Rental Income: $1742 Airbnb ROI: -0.2% Traditional ROI: 1.45%
11887 Somerset Ave Princess Anne, MD 11887 Somerset Ave, Princess Anne, MD 21853 \| Single Family Residential	6 beds \| 2 baths \| 3,979 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.47% Airbnb Rental Income: $null Traditional Rental Income: $2046 Airbnb ROI: N/A Traditional ROI: 3.47%
13310 Fitzbound Rd Princess Anne, MD 13310 Fitzbound Rd, Princess Anne, MD 21853 \| Single Family Residential	5 beds \| 3 baths \| 2,850 sq.ft.	$364,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.28% Airbnb Rental Income: $null Traditional Rental Income: $2615 Airbnb ROI: N/A Traditional ROI: 5.28%
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%
0 Whitehaven Ferry Rd Princess Anne, MD 0 Whitehaven Ferry Rd, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$245,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.24% Airbnb Rental Income: $null Traditional Rental Income: $862 Airbnb ROI: N/A Traditional ROI: 1.24%
28565 Polks Rd Princess Anne, MD 28565 Polks Rd, Princess Anne, MD 21853 \| Single Family Residential	3 beds \| 1 baths \| 936 sq.ft.	$135,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 8.36% Airbnb Rental Income: $1396 Traditional Rental Income: $1446 Airbnb ROI: 4.72% Traditional ROI: 8.36%
10824 Clipper Cir Princess Anne, MD 10824 Clipper Cir, Princess Anne, MD 21853 \| Single Family Residential	3 beds \| 2 baths \| 1,200 sq.ft.	$264,900	Airbnb cash on cash: 1.45% Traditional cash on cash: 3.84% Airbnb Rental Income: $1396 Traditional Rental Income: $1572 Airbnb ROI: 1.45% Traditional ROI: 3.84%
0 Five Farms Dr Princess Anne, MD 0 Five Farms Dr, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$59,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.43% Airbnb Rental Income: $null Traditional Rental Income: $603 Airbnb ROI: N/A Traditional ROI: 6.43%
10615 Rosewood Ct Princess Anne, MD 10615 Rosewood Ct, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$39,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.81% Airbnb Rental Income: $null Traditional Rental Income: $608 Airbnb ROI: N/A Traditional ROI: 9.81%
11528 Beckford Ave Princess Anne, MD 11528 Beckford Ave, Princess Anne, MD 21853 \| Single Family Residential	N/A beds \| N/A baths \| 1,442 sq.ft.	$160,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.8% Airbnb Rental Income: $null Traditional Rental Income: $1143 Airbnb ROI: N/A Traditional ROI: 4.8%
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%
26386 Mount Vernon Rd Princess Anne, MD 26386 Mount Vernon Rd, Princess Anne, MD 21853 \| Single Family Residential	7 beds \| 4 baths \| 3,143 sq.ft.	$950,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.87% Airbnb Rental Income: $null Traditional Rental Income: $2702 Airbnb ROI: N/A Traditional ROI: 0.87%
30435 DAPHNE Lane Princess Anne, MD Welcome to this spacious 3-bedroom, 2-bathroom home located in Princess Anne, Maryland, of...	3 beds \| 3 baths \| 1,458 sq.ft.	$325,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 5.87% Airbnb Rental Income: $1396 Traditional Rental Income: $2449 Airbnb ROI: 1.05% Traditional ROI: 5.87%
0 Clarence Barnes Rd Princess Anne, MD 0 Clarence Barnes Rd, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| N/A	$125,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $603 Airbnb ROI: N/A Traditional ROI: 2.16%
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 Photos used are of a completed house with the same floor plan by the same builder. Home to...	3 beds \| 2 baths \| 1,372 sq.ft.	$314,900	Airbnb cash on cash: 1.79% Traditional cash on cash: 5.3% Airbnb Rental Income: $1396 Traditional Rental Income: $2013 Airbnb ROI: 1.79% Traditional ROI: 5.3%
27112 Mt Vernon Rd Princess Anne, MD 27112 Mt Vernon Rd, Princess Anne, MD 21853 \| Single Family Residential	3 beds \| 2 baths \| 1,200 sq.ft.	$269,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.21% Airbnb Rental Income: $1396 Traditional Rental Income: $1688 Airbnb ROI: 1.4% Traditional ROI: 4.21%
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.	$365,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 3.87% Airbnb Rental Income: $1396 Traditional Rental Income: $2236 Airbnb ROI: 0.19% Traditional ROI: 3.87%

Real Estate investment in Princess-anne, MD

There are 33 properties for sale in the city of Princess Anne . The median list price in Princess Anne is $160,000 and the average price per square foot is $164. In January 2026, the average monthly cash on cash return in Princess Anne is 5.00%. The average monthly rental income in Princess Anne is $1,771.

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

There are 33 investment properties available for sale in Princess-anne.

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

The ROI for Long-Term is higher than the Short-Term in Princess-anne with average rental income of $1,771.

Your search for investment property begins and ends here

Investment Property for Sale in Princess Anne, MD

11635 Dennis Dr

Princess Anne, MD

3 beds | 2 baths | 1,658 sq.ft.

$285,000

Airbnb cash on cash: 0.55%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $1396

Traditional Rental Income: $1835

Airbnb ROI: 0.55%

Traditional ROI: 3.76%

11619 Somerset Ave

Princess Anne, MD

3 beds | 2 baths | 2,656 sq.ft.

$292,900

Airbnb cash on cash: 1.55%

Traditional cash on cash: 7.35%

Airbnb Rental Income: $1396

Traditional Rental Income: $2575

Airbnb ROI: 1.55%

Traditional ROI: 7.35%

11679 Beckford Ave

Princess Anne, MD

3 beds | 2 baths | 1,352 sq.ft.

$267,900

Airbnb cash on cash: 1.67%

Traditional cash on cash: 7.42%

Airbnb Rental Income: $1396

Traditional Rental Income: $2425

Airbnb ROI: 1.67%

Traditional ROI: 7.42%

30500 Valentine Dr

Princess Anne, MD

3 beds | 1 baths | 1,152 sq.ft.

$189,000

Airbnb cash on cash: 3.35%

Traditional cash on cash: 8.31%

Airbnb Rental Income: $1396

Traditional Rental Income: $1864

Airbnb ROI: 3.35%

Traditional ROI: 8.31%

11075 Jerusalem Rd

Princess Anne, MD

3 beds | 2 baths | 1,490 sq.ft.

$305,000

Airbnb cash on cash: 1.55%

Traditional cash on cash: 5.37%

Airbnb Rental Income: $1396

Traditional Rental Income: $2071

Airbnb ROI: 1.55%

Traditional ROI: 5.37%

11378 HAYMAN Drive

Princess Anne, MD

3 beds | 2 baths | 1,858 sq.ft.

$349,900

Airbnb cash on cash: 0.97%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $1396

Traditional Rental Income: $2405

Airbnb ROI: 0.97%

Traditional ROI: 5.33%

11410 Hayman Dr

Princess Anne, MD

3 beds | 2 baths | 1,665 sq.ft.

$274,995

Airbnb cash on cash: 1.58%

Traditional cash on cash: 6.52%

Airbnb Rental Income: $1396

Traditional Rental Income: $2256

Airbnb ROI: 1.58%

Traditional ROI: 6.52%

32792 W POST OFFICE RD

Princess Anne, MD

3 beds | 2 baths | N/A

$145,000

Airbnb cash on cash: 4.17%

Traditional cash on cash: 11.16%

Airbnb Rental Income: $1396

Traditional Rental Income: $1945

Airbnb ROI: 4.17%