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 4 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
21324 PERSIMMON Drive CHESTERTOWN, MD 2 level townhome in sought after Tolchester Village! Features a terrific open kitchen with...	2 beds \| 1 baths \| 1,232 sq.ft.	$136,800	Airbnb cash on cash: 6.71% Traditional cash on cash: 10.77% Airbnb Rental Income: $1721 Traditional Rental Income: $1778 Airbnb ROI: 6.71% Traditional ROI: 10.77%
108 OAK LEAF Drive CHESTERTOWN, MD This beautifully maintained end-unit townhome, owned by its original owner, has been metic...	2 beds \| 3 baths \| 1,867 sq.ft.	$299,500	Airbnb cash on cash: 1.03% Traditional cash on cash: 5.93% Airbnb Rental Income: $1721 Traditional Rental Income: $2628 Airbnb ROI: 1.03% Traditional ROI: 5.93%
Other Investment Properties for Sale in Chestertown
6746 QUAKER NECK Road CHESTERTOWN , MD	5 beds \| 3 baths \| 3,371 sq.ft.	$384,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 8.21% Airbnb Rental Income: $2925 Traditional Rental Income: $3607 Airbnb ROI: 4.44% Traditional ROI: 8.21%
704 TRUSLOW Road CHESTERTOWN , MD Tucked away in the peaceful countryside on the Queen Anne's County side of Chestertown, th...	3 beds \| 3 baths \| 2,060 sq.ft.	$440,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 5.43% Airbnb Rental Income: $1994 Traditional Rental Income: $3004 Airbnb ROI: 1.71% Traditional ROI: 5.43%
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.	$695,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 3.3% Airbnb Rental Income: $2028 Traditional Rental Income: $3409 Airbnb ROI: 0.36% Traditional ROI: 3.3%
109 WILTON Road CHESTERTOWN , MD Charming 3-bedroom, 2-bath rancher in the desirable Chester Harbor community. Situated on ...	3 beds \| 2 baths \| 1,392 sq.ft.	$344,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 5.69% Airbnb Rental Income: $1994 Traditional Rental Income: $2457 Airbnb ROI: 2.65% Traditional ROI: 5.69%
21217 TEXAS Avenue CHESTERTOWN , MD MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! ...	2 beds \| 1 baths \| 912 sq.ft.	$265,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 4.09% Airbnb Rental Income: $1721 Traditional Rental Income: $1527 Airbnb ROI: 2.96% Traditional ROI: 4.09%
10594 MILLBROOK Drive CHESTERTOWN , MD Professional photos coming soon! Welcome to this beautifully upgraded 3-bedroom, 2-bath Ca...	2 beds \| 1 baths \| 1,499 sq.ft.	$329,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 4.49% Airbnb Rental Income: $1721 Traditional Rental Income: $2025 Airbnb ROI: 1.97% Traditional ROI: 4.49%
110 TRAFFORD Drive CHESTERTOWN , MD Coventry Farms-Reduced to Sell, Offers Encouraged Located in the highly desirable Coventry...	4 beds \| 3 baths \| 2,880 sq.ft.	$465,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 5.03% Airbnb Rental Income: $2028 Traditional Rental Income: $3166 Airbnb ROI: 1.2% Traditional ROI: 5.03%
103 LANDING Lane CHESTERTOWN , MD Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable...	2 beds \| 3 baths \| 2,100 sq.ft.	$519,999	Airbnb cash on cash: -1.4% Traditional cash on cash: 1.73% Airbnb Rental Income: $1721 Traditional Rental Income: $2769 Airbnb ROI: -1.4% Traditional ROI: 1.73%
109 S COLLEGE Avenue CHESTERTOWN , MD Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial ble...	3 beds \| 3 baths \| 1,216 sq.ft.	$419,900	Airbnb cash on cash: 1.84% Traditional cash on cash: 2.68% Airbnb Rental Income: $1994 Traditional Rental Income: $1802 Airbnb ROI: 1.84% Traditional ROI: 2.68%
208 CENTRAL Drive CHESTERTOWN , MD Welcome to 208 Central Drive, nestled in the desirable Chester Harbor community just minut...	3 beds \| 1 baths \| 1,120 sq.ft.	$315,000	Airbnb cash on cash: 3.1% Traditional cash on cash: 4.4% Airbnb Rental Income: $1994 Traditional Rental Income: $1857 Airbnb ROI: 3.1% Traditional ROI: 4.4%
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: 2.42% Traditional cash on cash: 3.51% Airbnb Rental Income: $2925 Traditional Rental Income: $2770 Airbnb ROI: 2.42% Traditional ROI: 3.51%
105 HIGH Street CHESTERTOWN , MD Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one ...	5 beds \| 5 baths \| 3,243 sq.ft.	$1,395,500	Airbnb cash on cash: -0.78% Traditional cash on cash: 1.25% Airbnb Rental Income: $2925 Traditional Rental Income: $4880 Airbnb ROI: -0.78% Traditional ROI: 1.25%
201 BIRCH RUN Road CHESTERTOWN , MD ***PRICED $30,000 UNDER THE RECENT APPRAISED VALUE*** One floor living, a wood burning...	3 beds \| 2 baths \| 1,588 sq.ft.	$435,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 4.77% Airbnb Rental Income: $1994 Traditional Rental Income: $2896 Airbnb ROI: 1.27% Traditional ROI: 4.77%
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.	$339,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 5.15% Airbnb Rental Income: $2028 Traditional Rental Income: $2284 Airbnb ROI: 2.69% Traditional ROI: 5.15%
234 N COLLEGE Avenue CHESTERTOWN , MD Investor Special - Charming Colonial in Prime Chestertown Location! Welcome to 234 N Colle...	2 beds \| 1 baths \| 1,296 sq.ft.	$130,000	Airbnb cash on cash: 6.99% Traditional cash on cash: 11.51% Airbnb Rental Income: $1721 Traditional Rental Income: $1811 Airbnb ROI: 6.99% Traditional ROI: 11.51%

Your search for investment property begins and ends here

Townhouses for Sale in Chestertown, MD

21324 PERSIMMON Drive

CHESTERTOWN, MD

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

$136,800

Airbnb cash on cash: 6.71%

Traditional cash on cash: 10.77%

Airbnb Rental Income: $1721

Traditional Rental Income: $1778

Airbnb ROI: 6.71%

Traditional ROI: 10.77%

108 OAK LEAF Drive

CHESTERTOWN, MD

2 beds | 3 baths | 1,867 sq.ft.

$299,500

Airbnb cash on cash: 1.03%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $1721

Traditional Rental Income: $2628

Airbnb ROI: 1.03%

Traditional ROI: 5.93%

Other Investment Properties for Sale in Chestertown

CHESTERTOWN , MD

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

$384,000

Airbnb cash on cash: 4.44%

Traditional cash on cash: 8.21%

Airbnb Rental Income: $2925

Traditional Rental Income: $3607

Airbnb ROI: 4.44%

Traditional ROI: 8.21%

CHESTERTOWN , MD

3 beds | 3 baths | 2,060 sq.ft.

$440,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: 5.43%

Airbnb Rental Income: $1994

Traditional Rental Income: $3004

Airbnb ROI: 1.71%

Traditional ROI: 5.43%

CHESTERTOWN , MD

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

$695,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $2028

Traditional Rental Income: $3409

Airbnb ROI: 0.36%

Traditional ROI: 3.3%

CHESTERTOWN , MD

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

$344,900

Airbnb cash on cash: 2.65%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $1994

Traditional Rental Income: $2457

Airbnb ROI: 2.65%

Traditional ROI: 5.69%

CHESTERTOWN , MD

2 beds | 1 baths | 912 sq.ft.

$265,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $1721

Traditional Rental Income: $1527

Airbnb ROI: 2.96%

Traditional ROI: 4.09%

CHESTERTOWN , MD

2 beds | 1 baths | 1,499 sq.ft.

$329,000

Airbnb cash on cash: 1.97%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $1721

Traditional Rental Income: $2025

Airbnb ROI: 1.97%

Traditional ROI: 4.49%

CHESTERTOWN , MD

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

$465,000

Airbnb cash on cash: 1.2%