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%
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.	$640,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.63% Airbnb Rental Income: $null Traditional Rental Income: $3407 Airbnb ROI: N/A Traditional ROI: 3.63%
11484 Somerset Ave Princess Anne, MD 2.32 Acre Corner Lot Zoned Multifamily Cleared and ready to build Previously approved for ...	3 beds \| 2 baths \| 1,120 sq.ft.	$245,900	Airbnb cash on cash: 4.04% Traditional cash on cash: 3.85% Airbnb Rental Income: $1829 Traditional Rental Income: $1290 Airbnb ROI: 4.04% Traditional ROI: 3.85%
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.	$225,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 6.24% Airbnb Rental Income: $1829 Traditional Rental Income: $1773 Airbnb ROI: 4.18% Traditional ROI: 6.24%
11685 Beckford Ave Princess Anne, MD Are you looking for a home with that classic colonial charm, without turning your life int...	3 beds \| 2 baths \| 1,289 sq.ft.	$259,900	Airbnb cash on cash: 2.97% Traditional cash on cash: 5.72% Airbnb Rental Income: $1829 Traditional Rental Income: $2009 Airbnb ROI: 2.97% Traditional ROI: 5.72%
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.	$279,900	Airbnb cash on cash: 1.95% Traditional cash on cash: 3.84% Airbnb Rental Income: $1829 Traditional Rental Income: $1835 Airbnb ROI: 1.95% Traditional ROI: 3.84%
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.	$285,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 7.58% Airbnb Rental Income: $1829 Traditional Rental Income: $2575 Airbnb ROI: 2.96% Traditional ROI: 7.58%
28703 Adlers Rest Ln Princess Anne, MD Adlers Rest Waterfront Home is on 10.8+/- acres on the Wicomico River. The home is located...	4 beds \| 2 baths \| 1,752 sq.ft.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.86% Airbnb Rental Income: $null Traditional Rental Income: $2849 Airbnb ROI: N/A Traditional ROI: 5.86%
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.	$2,950,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.9% Airbnb Rental Income: $null Traditional Rental Income: $6355 Airbnb ROI: N/A Traditional ROI: 0.9%
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: 1.25% Traditional cash on cash: 3.06% Airbnb Rental Income: $1829 Traditional Rental Income: $2183 Airbnb ROI: 1.25% Traditional ROI: 3.06%
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: 2.51% Traditional cash on cash: 3.78% Airbnb Rental Income: $1829 Traditional Rental Income: $1632 Airbnb ROI: 2.51% 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%
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.	$460,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 1.75% Airbnb Rental Income: $1829 Traditional Rental Income: $1742 Airbnb ROI: 0.8% Traditional ROI: 1.75%
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.	$309,900	Airbnb cash on cash: 2.43% Traditional cash on cash: 4.75% Airbnb Rental Income: $1829 Traditional Rental Income: $2013 Airbnb ROI: 2.43% Traditional ROI: 4.75%
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: 1.24% Traditional cash on cash: 3.87% Airbnb Rental Income: $1829 Traditional Rental Income: $2236 Airbnb ROI: 1.24% Traditional ROI: 3.87%
0 Champ Rd Princess Anne, MD 0 Champ Rd, Princess Anne, MD 21853 \| Other	N/A beds \| N/A baths \| N/A	$98,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.04% Airbnb Rental Income: $null Traditional Rental Income: $678 Airbnb ROI: N/A Traditional ROI: 4.04%
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: 4.31% Traditional cash on cash: 2.32% Airbnb Rental Income: $1829 Traditional Rental Income: $948 Airbnb ROI: 4.31% 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.	$249,999	Airbnb cash on cash: 2.41% Traditional cash on cash: 3.63% Airbnb Rental Income: $1829 Traditional Rental Income: $1625 Airbnb ROI: 2.41% Traditional ROI: 3.63%
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: -0.07% Traditional cash on cash: 1.27% Airbnb Rental Income: $1829 Traditional Rental Income: $2146 Airbnb ROI: -0.07% 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%
26465 Mason Webster Rd Princess Anne, MD 26465 Mason Webster Rd, Princess Anne, MD 21853 \| Single Family Residential	3 beds \| 2 baths \| 1,090 sq.ft.	$195,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 6.5% Airbnb Rental Income: $1829 Traditional Rental Income: $1681 Airbnb ROI: 4.63% Traditional ROI: 6.5%
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: 3.18% Traditional cash on cash: 4.91% Airbnb Rental Income: $1829 Traditional Rental Income: $1744 Airbnb ROI: 3.18% Traditional ROI: 4.91%
11956 Robyn Ln Princess Anne, MD Welcome home to this move-in ready property situated on an oversized corner lot in Princes...	3 beds \| 2 baths \| 1,040 sq.ft.	$239,900	Airbnb cash on cash: 3.74% Traditional cash on cash: 6.46% Airbnb Rental Income: $1829 Traditional Rental Income: $1952 Airbnb ROI: 3.74% Traditional ROI: 6.46%
11163 Stewart Neck Rd Princess Anne, MD 11163 Stewart Neck Rd, Princess Anne, MD 21853 \| Single Family Residential	4 beds \| 2 baths \| 1,970 sq.ft.	$364,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $2113 Airbnb ROI: N/A Traditional ROI: 3.82%
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: 2.36% Traditional cash on cash: 3.47% Airbnb Rental Income: $1829 Traditional Rental Income: $1646 Airbnb ROI: 2.36% 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.	$284,990	Airbnb cash on cash: 2.07% Traditional cash on cash: 5.05% Airbnb Rental Income: $1829 Traditional Rental Income: $2137 Airbnb ROI: 2.07% Traditional ROI: 5.05%
11651 Freetown Rd Princess Anne, MD 11651 Freetown Rd, Princess Anne, MD 21853 \| Single Family Residential	3 beds \| 2 baths \| 1,296 sq.ft.	$119,900	Airbnb cash on cash: 8.67% Traditional cash on cash: 11.81% Airbnb Rental Income: $1829 Traditional Rental Income: $1698 Airbnb ROI: 8.67% Traditional ROI: 11.81%
11951 Robyn Ln Princess Anne, MD Meticulously Maintained Home with Pole Barn, Pool, and Premium Upgrades Welcome to 11951 R...	3 beds \| 2 baths \| 960 sq.ft.	$247,300	Airbnb cash on cash: 3.12% Traditional cash on cash: 4.68% Airbnb Rental Income: $1829 Traditional Rental Income: $1701 Airbnb ROI: 3.12% Traditional ROI: 4.68%
13712 Crows Foot Ln Princess Anne, MD	N/A beds \| N/A baths \| N/A	$69,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.68% Airbnb Rental Income: $null Traditional Rental Income: $699 Airbnb ROI: N/A Traditional ROI: 6.68%
27174 Champ Wharf Rd Champ Wharf #27174 Princess Anne, MD The perfect getaway! This beautiful 2 bedroom 2 bath waterfront home is located on the qui...	2 beds \| 2 baths \| 1,232 sq.ft.	$299,500	Airbnb cash on cash: 2.25% Traditional cash on cash: 5.4% Airbnb Rental Income: $1670 Traditional Rental Income: $2092 Airbnb ROI: 2.25% 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.	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.44% Airbnb Rental Income: $null Traditional Rental Income: $2308 Airbnb ROI: N/A Traditional ROI: 1.44%
30124 Peggy Ln Princess Anne, MD Situated on over 3.75 private, meticulously maintained acres, this one-of-a-kind property ...	3 beds \| 2 baths \| 2,296 sq.ft.	$415,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 3.29% Airbnb Rental Income: $1829 Traditional Rental Income: $2036 Airbnb ROI: 1.49% Traditional ROI: 3.29%

Real Estate investment in Princess-anne, MD

There are 48 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 August 2026, the average monthly cash on cash return in Princess Anne is 5.00%. The average monthly rental income in Princess Anne is $1,698.

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

There are 48 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 $1,698.

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%

11700 Mansion St

Princess Anne, MD

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

$640,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.63%

Airbnb Rental Income: $null

Traditional Rental Income: $3407

Airbnb ROI: N/A

Traditional ROI: 3.63%

11484 Somerset Ave

Princess Anne, MD

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

$245,900

Airbnb cash on cash: 4.04%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $1829

Traditional Rental Income: $1290

Airbnb ROI: 4.04%

Traditional ROI: 3.85%

30030 Greenspring Dr

Princess Anne, MD

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

$225,000

Airbnb cash on cash: 4.18%

Traditional cash on cash: 6.24%

Airbnb Rental Income: $1829

Traditional Rental Income: $1773

Airbnb ROI: 4.18%

Traditional ROI: 6.24%

11685 Beckford Ave

Princess Anne, MD

3 beds | 2 baths | 1,289 sq.ft.

$259,900

Airbnb cash on cash: 2.97%

Traditional cash on cash: 5.72%

Airbnb Rental Income: $1829

Traditional Rental Income: $2009

Airbnb ROI: 2.97%

Traditional ROI: 5.72%

11635 Dennis Dr

Princess Anne, MD

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

$279,900

Airbnb cash on cash: 1.95%

Traditional cash on cash: 3.84%

Airbnb Rental Income: $1829

Traditional Rental Income: $1835

Airbnb ROI: 1.95%

Traditional ROI: 3.84%

11619 Somerset Ave

Princess Anne, MD

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

$285,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 7.58%

Airbnb Rental Income: $1829

Traditional Rental Income: $2575

Airbnb ROI: 2.96%