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.

Single Family Homes for Sale in Chestertown, MD

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

Showing 10 Single Family Residential 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
105 Pearl Creek Ln CHESTERTOWN, MD (Open House January 31 from 10:00 - 12:00) Welcome to your private Eastern Shore retreat o...	3 beds \| 2 baths \| 1,961 sq.ft.	$449,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 5.35% Airbnb Rental Income: $2892 Traditional Rental Income: $3018 Airbnb ROI: 3.46% Traditional ROI: 5.35%
129 Parma Rd 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 Rd 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%
119 Darden Rd 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.	$275,000	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%
8750 Georgetown Rd CHESTERTOWN, MD Price Improvement = Even More Value! Discover the perfect blend of space, privacy, and com...	3 beds \| 2 baths \| 1,900 sq.ft.	$334,000	Airbnb cash on cash: 4.95% Traditional cash on cash: 5.85% Airbnb Rental Income: $2892 Traditional Rental Income: $2505 Airbnb ROI: 4.95% Traditional ROI: 5.85%
216 Blakefield Dr CHESTERTOWN, MD The wait is over 216 Blakefield Drive is complete, ready for occupancy and you will not be...	4 beds \| 3 baths \| 2,400 sq.ft.	$559,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 3.71% Airbnb Rental Income: $1948 Traditional Rental Income: $3224 Airbnb ROI: 0.4% Traditional ROI: 3.71%
121 Primrose Rd CHESTERTOWN, MD Motivated Seller. Welcome to 121 Primrose Road, a well-built two-story home offering 2,034...	3 beds \| 2 baths \| 2,034 sq.ft.	$350,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 7.01% Airbnb Rental Income: $2892 Traditional Rental Income: $2995 Airbnb ROI: 4.65% Traditional ROI: 7.01%
213 Central Dr CHESTERTOWN, MD Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh pain...	3 beds \| 2 baths \| 1,232 sq.ft.	$314,900	Airbnb cash on cash: 5.56% Traditional cash on cash: 6.04% Airbnb Rental Income: $2892 Traditional Rental Income: $2363 Airbnb ROI: 5.56% Traditional ROI: 6.04%
22481 GOOSE HOLLOW Drive CHESTERTOWN, MD Welcome to peaceful country living with modern comfort. This beautifully updated 3-bedroom...	3 beds \| 2 baths \| 1,296 sq.ft.	$379,500	Airbnb cash on cash: 4.39% Traditional cash on cash: 4.21% Airbnb Rental Income: $2892 Traditional Rental Income: $2156 Airbnb ROI: 4.39% Traditional ROI: 4.21%
222 Dutchess Rd CHESTERTOWN, MD 222 Dutchess Rd, CHESTERTOWN, MD 21620 \| Single Family Residential	3 beds \| 1 baths \| 1,096 sq.ft.	$320,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 2.74% Airbnb Rental Income: $2892 Traditional Rental Income: $1545 Airbnb ROI: 4.99% Traditional ROI: 2.74%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chestertown, MD

105 Pearl Creek Ln

CHESTERTOWN, MD

3 beds | 2 baths | 1,961 sq.ft.

$449,000

Airbnb cash on cash: 3.46%

Traditional cash on cash: 5.35%

Airbnb Rental Income: $2892

Traditional Rental Income: $3018

Airbnb ROI: 3.46%

Traditional ROI: 5.35%

129 Parma Rd

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%

109 Wilton Rd

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%

119 Darden Rd

CHESTERTOWN, MD

3 beds | 2 baths | 1,424 sq.ft.

$275,000

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%

8750 Georgetown Rd

CHESTERTOWN, MD

3 beds | 2 baths | 1,900 sq.ft.

$334,000

Airbnb cash on cash: 4.95%

Traditional cash on cash: 5.85%

Airbnb Rental Income: $2892

Traditional Rental Income: $2505

Airbnb ROI: 4.95%

Traditional ROI: 5.85%

216 Blakefield Dr

CHESTERTOWN, MD

4 beds | 3 baths | 2,400 sq.ft.

$559,000

Airbnb cash on cash: 0.4%

Traditional cash on cash: 3.71%

Airbnb Rental Income: $1948

Traditional Rental Income: $3224

Airbnb ROI: 0.4%

Traditional ROI: 3.71%

121 Primrose Rd

CHESTERTOWN, MD

3 beds | 2 baths | 2,034 sq.ft.

$350,000

Airbnb cash on cash: 4.65%

Traditional cash on cash: 7.01%

Airbnb Rental Income: $2892

Traditional Rental Income: $2995

Airbnb ROI: 4.65%

Traditional ROI: 7.01%

213 Central Dr

CHESTERTOWN, MD

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

$314,900

Airbnb cash on cash: 5.56%

Traditional cash on cash: 6.04%

Airbnb Rental Income: $2892

Traditional Rental Income: $2363

Airbnb ROI: 5.56%