Real Estate Investment Properties for Sale in Tilghman, MD

Looking for investment property in Tilghman, MD with high ROI ?

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
21552 CHICKEN POINT Road TILGHMAN, MD Located minutes from St. Michaels this waterfront property is a boater's dream. Tilghman, ...	5 beds \| 2 baths \| 2,655 sq.ft.	$970,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 1.8% Airbnb Rental Income: $948 Traditional Rental Income: $3021 Airbnb ROI: -0.88% Traditional ROI: 1.8%
21441 DOGWOOD COVE Road TILGHMAN, MD Unique Tilghman Island Property. Zoned Residential-Commercial. Situated on a 2.74 acre fen...	3 beds \| 3 baths \| 2,477 sq.ft.	$1,350,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.22% Airbnb Rental Income: $1770 Traditional Rental Income: $3478 Airbnb ROI: -0.53% Traditional ROI: 1.22%
21572 CHICKEN POINT Road TILGHMAN, MD The opportunities abound for this waterfront home overlooking the Knapps Narrows. Formally...	2 beds \| 3 baths \| 1,729 sq.ft.	$925,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 1.79% Airbnb Rental Income: $2627 Traditional Rental Income: $3004 Airbnb ROI: 0.63% Traditional ROI: 1.79%
5648 TRAFALGAR Circle TILGHMAN, MD Built in 2025, this new construction home offers the best of Eastern Shore living in the w...	3 beds \| 2 baths \| 2,068 sq.ft.	$544,888	Airbnb cash on cash: 0.08% Traditional cash on cash: 1.72% Airbnb Rental Income: $1770 Traditional Rental Income: $2118 Airbnb ROI: 0.08% Traditional ROI: 1.72%
5654 TRAFALGAR Circle TILGHMAN, MD	3 beds \| 2 baths \| 1,710 sq.ft.	$499,888	Airbnb cash on cash: 0.78% Traditional cash on cash: 2.63% Airbnb Rental Income: $1770 Traditional Rental Income: $2151 Airbnb ROI: 0.78% Traditional ROI: 2.63%
21560 CHICKEN POINT Road TILGHMAN, MD Renovated waterfront living with room for your fleet! Extensively renovated Cape Cod on Ti...	3 beds \| 2 baths \| 1,314 sq.ft.	$870,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 1.69% Airbnb Rental Income: $1770 Traditional Rental Income: $2564 Airbnb ROI: 0.11% Traditional ROI: 1.69%
21530 COOPERTOWN Road TILGHMAN, MD This charming Tilghman Island cottage was originally built in 1953 and thoughtfully renova...	3 beds \| 1 baths \| 996 sq.ft.	$279,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 5.61% Airbnb Rental Income: $1770 Traditional Rental Income: $1936 Airbnb ROI: 3.14% Traditional ROI: 5.61%

Real Estate investment in Tilghman, MD

There are 7 properties for sale in the city of Tilghman . The median list price in Tilghman is $870,000 and the average price per square foot is $470. In June 2026, the average monthly cash on cash return in Tilghman is 2.00%. The average monthly rental income in Tilghman is $2,703.

Tilghman, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 7 investment properties available for sale in Tilghman.

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

The ROI for Short-Term is higher than the Long-Term in Tilghman with average rental income of $1,770.

Your search for investment property begins and ends here

Investment Property for Sale in Tilghman, MD

21552 CHICKEN POINT Road

TILGHMAN, MD

5 beds | 2 baths | 2,655 sq.ft.

$970,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $948

Traditional Rental Income: $3021

Airbnb ROI: -0.88%

Traditional ROI: 1.8%

21441 DOGWOOD COVE Road

TILGHMAN, MD

3 beds | 3 baths | 2,477 sq.ft.

$1,350,000

Airbnb cash on cash: -0.53%

Traditional cash on cash: 1.22%

Airbnb Rental Income: $1770

Traditional Rental Income: $3478

Airbnb ROI: -0.53%

Traditional ROI: 1.22%

21572 CHICKEN POINT Road

TILGHMAN, MD

2 beds | 3 baths | 1,729 sq.ft.

$925,000

Airbnb cash on cash: 0.63%

Traditional cash on cash: 1.79%

Airbnb Rental Income: $2627

Traditional Rental Income: $3004

Airbnb ROI: 0.63%

Traditional ROI: 1.79%

5648 TRAFALGAR Circle

TILGHMAN, MD

3 beds | 2 baths | 2,068 sq.ft.

$544,888

Airbnb cash on cash: 0.08%

Traditional cash on cash: 1.72%

Airbnb Rental Income: $1770

Traditional Rental Income: $2118

Airbnb ROI: 0.08%

Traditional ROI: 1.72%

5654 TRAFALGAR Circle

TILGHMAN, MD

3 beds | 2 baths | 1,710 sq.ft.

$499,888

Airbnb cash on cash: 0.78%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $1770

Traditional Rental Income: $2151

Airbnb ROI: 0.78%

Traditional ROI: 2.63%

21560 CHICKEN POINT Road

TILGHMAN, MD

3 beds | 2 baths | 1,314 sq.ft.

$870,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 1.69%

Airbnb Rental Income: $1770

Traditional Rental Income: $2564

Airbnb ROI: 0.11%

Traditional ROI: 1.69%

21530 COOPERTOWN Road

TILGHMAN, MD

3 beds | 1 baths | 996 sq.ft.

$279,000

Airbnb cash on cash: 3.14%

Traditional cash on cash: 5.61%

Airbnb Rental Income: $1770

Traditional Rental Income: $1936

Airbnb ROI: 3.14%

Traditional ROI: 5.61%

Real Estate investment in Tilghman, MD

Tilghman, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

How many investment properties are available for sale in Tilghman?

Which neighborhoods in Tilghman to invest in 2026?

Long-Term vs. Short-Term Rentals in Tilghman, Maryland: Which will earn the best returns?

Use analytics to find lucrative traditional or Airbnb properties in a matter of minutes.

No more spreadsheets, no more searching.