Real Estate Investment Properties for Sale in Chestertown, MD

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

Explore a variety of short-term homes & houses in Chestertown, MD. Invest wisely with VRBO & Chestertown, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Townhouses for Sale in Chestertown, MD

Search for Townhouse for Sale in Chestertown, Maryland. Browse all of Mashvisor’s Townhouse listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 3 Townhouse 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
21316 PERSIMMON Drive CHESTERTOWN, MD Back on the market through no fault of the sellers. Home inspection went well. Two bedroom...	2 beds \| 1 baths \| 1,232 sq.ft.	$169,000	Airbnb cash on cash: 6.24% Traditional cash on cash: 8.71% Airbnb Rental Income: $1999 Traditional Rental Income: $1876 Airbnb ROI: 6.24% Traditional ROI: 8.71%
103 METCALF RD CHESTERTOWN, MD Brand new home in Historic Chestertown available for move-in this October. This home featu...	3 beds \| 2 baths \| 1,280 sq.ft.	$259,900	Airbnb cash on cash: 6.6% Traditional cash on cash: 6.24% Airbnb Rental Income: $2892 Traditional Rental Income: $2133 Airbnb ROI: 6.6% Traditional ROI: 6.24%
109 METCALF Road CHESTERTOWN, MD Brand new home in Historic Chestertown available for move-in Right Now. This home features...	3 beds \| 2 baths \| 1,280 sq.ft.	$264,900	Airbnb cash on cash: 7.3% Traditional cash on cash: 7.32% Airbnb Rental Income: $2892 Traditional Rental Income: $2225 Airbnb ROI: 7.3% Traditional ROI: 7.32%
Other Investment Properties for Sale in Chestertown
100 ADELA Way CHESTERTOWN , MD Days on Market Reporting Incorrectly- Property listed Oct 30, 2025 Nestled just outside ...	4 beds \| 4 baths \| 3,799 sq.ft.	$500,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 5.49% Airbnb Rental Income: $1948 Traditional Rental Income: $3673 Airbnb ROI: 0.71% Traditional ROI: 5.49%
6746 QUAKER NECK Road CHESTERTOWN , MD	5 beds \| 3 baths \| 3,371 sq.ft.	$445,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 6.96% Airbnb Rental Income: $3223 Traditional Rental Income: $3607 Airbnb ROI: 4.3% Traditional ROI: 6.96%
7844 CHESTER Court CHESTERTOWN , MD Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with th...	4 beds \| 3 baths \| 3,248 sq.ft.	$745,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 3.01% Airbnb Rental Income: $1948 Traditional Rental Income: $3409 Airbnb ROI: 0.17% Traditional ROI: 3.01%
129 PARMA Road CHESTERTOWN , MD Welcome to Chester Harbor. This one level home offers 3 bedroom 2 baths with LVP flooring ...	3 beds \| 2 baths \| 1,170 sq.ft.	$330,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 5.49% Airbnb Rental Income: $2892 Traditional Rental Income: $2336 Airbnb ROI: 5.12% Traditional ROI: 5.49%
109 WILTON Road CHESTERTOWN , MD Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comf...	3 beds \| 2 baths \| 1,392 sq.ft.	$344,900	Airbnb cash on cash: 5.01% Traditional cash on cash: 5.74% Airbnb Rental Income: $2892 Traditional Rental Income: $2457 Airbnb ROI: 5.01% Traditional ROI: 5.74%
110 TRAFFORD Drive CHESTERTOWN , MD Discover an incredible opportunity in the highly sought-after Coventry Farms community-one...	4 beds \| 3 baths \| 2,880 sq.ft.	$475,000	Airbnb cash on cash: 1% Traditional cash on cash: 4.9% Airbnb Rental Income: $1948 Traditional Rental Income: $3166 Airbnb ROI: 1% Traditional ROI: 4.9%
251 DEVON Drive CHESTERTOWN , MD NO HOA OR FRONT FEES: Welcome to 251 Devon Drive located in the desirable Coventry Farms n...	3 beds \| 3 baths \| 3,935 sq.ft.	$595,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 2.77% Airbnb Rental Income: $2892 Traditional Rental Income: $2834 Airbnb ROI: 1.67% Traditional ROI: 2.77%
119 DARDEN Road CHESTERTOWN , MD Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This cha...	3 beds \| 2 baths \| 1,424 sq.ft.	$315,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 5.08% Airbnb Rental Income: $2892 Traditional Rental Income: $2055 Airbnb ROI: 5.64% Traditional ROI: 5.08%
116 HARLAN Loop CHESTERTOWN , MD Welcome to Coventry Farms in Chestertown - where comfort, elegance, and space come togethe...	5 beds \| 4 baths \| 4,067 sq.ft.	$509,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 3.51% Airbnb Rental Income: $3223 Traditional Rental Income: $2770 Airbnb ROI: 2.94% Traditional ROI: 3.51%
105 HIGH Street CHESTERTOWN , MD This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases clas...	5 beds \| 5 baths \| 3,243 sq.ft.	$1,395,500	Airbnb cash on cash: -0.59% Traditional cash on cash: 1.25% Airbnb Rental Income: $3223 Traditional Rental Income: $4880 Airbnb ROI: -0.59% Traditional ROI: 1.25%
304 HADAWAY Drive CHESTERTOWN , MD Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready f...	4 beds \| 2 baths \| 1,325 sq.ft.	$350,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 4.97% Airbnb Rental Income: $1948 Traditional Rental Income: $2284 Airbnb ROI: 2.39% Traditional ROI: 4.97%
23043 BAY SHORE Spur CHESTERTOWN , MD Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 ac...	4 beds \| 3 baths \| 2,630 sq.ft.	$325,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 6.49% Airbnb Rental Income: $1948 Traditional Rental Income: $2650 Airbnb ROI: 2.51% Traditional ROI: 6.49%
7989 QUAKER NECK Road CHESTERTOWN , MD Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the ...	5 beds \| 5 baths \| 4,305 sq.ft.	$2,500,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 1.3% Airbnb Rental Income: $3223 Traditional Rental Income: $6617 Airbnb ROI: -0.48% Traditional ROI: 1.3%
23110 OLD FAIRLEE Road CHESTERTOWN , MD Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impress...	3 beds \| 1 baths \| 1,805 sq.ft.	$349,900	Airbnb cash on cash: 4.93% Traditional cash on cash: 3.62% Airbnb Rental Income: $2892 Traditional Rental Income: $1791 Airbnb ROI: 4.93% Traditional ROI: 3.62%

Your search for investment property begins and ends here

Townhouses for Sale in Chestertown, MD

21316 PERSIMMON Drive

CHESTERTOWN, MD

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

$169,000

Airbnb cash on cash: 6.24%

Traditional cash on cash: 8.71%

Airbnb Rental Income: $1999

Traditional Rental Income: $1876

Airbnb ROI: 6.24%

Traditional ROI: 8.71%

103 METCALF RD

CHESTERTOWN, MD

3 beds | 2 baths | 1,280 sq.ft.

$259,900

Airbnb cash on cash: 6.6%

Traditional cash on cash: 6.24%

Airbnb Rental Income: $2892

Traditional Rental Income: $2133

Airbnb ROI: 6.6%

Traditional ROI: 6.24%

109 METCALF Road

CHESTERTOWN, MD

3 beds | 2 baths | 1,280 sq.ft.

$264,900

Airbnb cash on cash: 7.3%

Traditional cash on cash: 7.32%

Airbnb Rental Income: $2892

Traditional Rental Income: $2225

Airbnb ROI: 7.3%

Traditional ROI: 7.32%

Other Investment Properties for Sale in Chestertown

CHESTERTOWN , MD

4 beds | 4 baths | 3,799 sq.ft.

$500,000

Airbnb cash on cash: 0.71%

Traditional cash on cash: 5.49%

Airbnb Rental Income: $1948

Traditional Rental Income: $3673

Airbnb ROI: 0.71%

Traditional ROI: 5.49%

CHESTERTOWN , MD

5 beds | 3 baths | 3,371 sq.ft.

$445,000

Airbnb cash on cash: 4.3%

Traditional cash on cash: 6.96%

Airbnb Rental Income: $3223

Traditional Rental Income: $3607

Airbnb ROI: 4.3%

Traditional ROI: 6.96%

CHESTERTOWN , MD

4 beds | 3 baths | 3,248 sq.ft.

$745,000

Airbnb cash on cash: 0.17%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $1948

Traditional Rental Income: $3409

Airbnb ROI: 0.17%

Traditional ROI: 3.01%

CHESTERTOWN , MD

3 beds | 2 baths | 1,170 sq.ft.

$330,000

Airbnb cash on cash: 5.12%

Traditional cash on cash: 5.49%

Airbnb Rental Income: $2892

Traditional Rental Income: $2336

Airbnb ROI: 5.12%

Traditional ROI: 5.49%

CHESTERTOWN , MD

3 beds | 2 baths | 1,392 sq.ft.

$344,900

Airbnb cash on cash: 5.01%

Traditional cash on cash: 5.74%

Airbnb Rental Income: $2892

Traditional Rental Income: $2457

Airbnb ROI: 5.01%

Traditional ROI: 5.74%

CHESTERTOWN , MD

4 beds | 3 baths | 2,880 sq.ft.

$475,000