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.

Investment Property for Sale in Chestertown, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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: 5.38% Airbnb Rental Income: $2892 Traditional Rental Income: $2300 Airbnb ROI: 5.12% Traditional ROI: 5.38%
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%
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%
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%
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%
8750 GEORGETOWN Road 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%
8620 PARK Drive CHESTERTOWN, MD Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq f...	4 beds \| 3 baths \| 2,524 sq.ft.	$499,900	Airbnb cash on cash: 1.26% Traditional cash on cash: 5.29% Airbnb Rental Income: $1948 Traditional Rental Income: $3316 Airbnb ROI: 1.26% Traditional ROI: 5.29%
108 FLYING CLOUD Drive CHESTERTOWN, MD New Year, new home! No need to worry for years about the roof or mechanics!! Built in 2023...	4 beds \| 3 baths \| 1,936 sq.ft.	$364,900	Airbnb cash on cash: 1.69% Traditional cash on cash: 5.94% Airbnb Rental Income: $1948 Traditional Rental Income: $2892 Airbnb ROI: 1.69% Traditional ROI: 5.94%
204 ROLLING Road CHESTERTOWN, MD Live with ease in this beautifully updated and maintained one floor home in downtown Chest...	3 beds \| 2 baths \| 2,296 sq.ft.	$345,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 5.74% Airbnb Rental Income: $2892 Traditional Rental Income: $2608 Airbnb ROI: 4.54% Traditional ROI: 5.74%
311 DEVON Drive CHESTERTOWN, MD 311 Devon Drive is located in Coventry Farms; and being located within the Chestertown tow...	5 beds \| 4 baths \| 3,504 sq.ft.	$598,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 4.45% Airbnb Rental Income: $3223 Traditional Rental Income: $3809 Airbnb ROI: 2.1% Traditional ROI: 4.45%
216 BLAKEFIELD Drive CHESTERTOWN, MD Discover the charm of this stunning new construction home in the desirable Blakefield comm...	4 beds \| 3 baths \| 2,400 sq.ft.	$579,000	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 Road CHESTERTOWN, MD Motivated Sellers!!! Welcome to 121 Primrose Road, a spacious two-story residence offering...	3 beds \| 3 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 Drive 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%
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%
218 CAMELOT Drive CHESTERTOWN, MD Picture Perfect Colonial in Coventry Farms - Chestertown, Maryland Welcome to 218 Camelot ...	5 beds \| 4 baths \| 3,932 sq.ft.	$525,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 5.63% Airbnb Rental Income: $3223 Traditional Rental Income: $3905 Airbnb ROI: 2.76% Traditional ROI: 5.63%
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%
127 Wood Duck Ln CHESTERTOWN, MD	3 beds \| 2 baths \| 1,666 sq.ft.	$215,000	Airbnb cash on cash: 8.37% Traditional cash on cash: 6.34% Airbnb Rental Income: $2892 Traditional Rental Income: $1807 Airbnb ROI: 8.37% Traditional ROI: 6.34%
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%
24339 CHESTERTOWN Road CHESTERTOWN, MD One level rancher with new HVAC, new 200 amp electric panel. The water conditioner is owne...	3 beds \| 1 baths \| 960 sq.ft.	$269,000	Airbnb cash on cash: 6.76% Traditional cash on cash: 7.07% Airbnb Rental Income: $2892 Traditional Rental Income: $2300 Airbnb ROI: 6.76% Traditional ROI: 7.07%

Real Estate investment in Chestertown, MD

There are 30 properties for sale in the city of Chestertown . The median list price in Chestertown is $349,950 and the average price per square foot is $157. In January 2026, the average monthly cash on cash return in Chestertown is 4.00%. The average monthly rental income in Chestertown is $2,457.

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

There are 30 investment properties available for sale in Chestertown.

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

The ROI for Long-Term is higher than the Short-Term in Chestertown with average rental income of $2,457.

Your search for investment property begins and ends here

Investment Property for Sale in Chestertown, MD

100 ADELA Way

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%

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

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

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

$330,000

Airbnb cash on cash: 5.12%

Traditional cash on cash: 5.38%

Airbnb Rental Income: $2892

Traditional Rental Income: $2300

Airbnb ROI: 5.12%

Traditional ROI: 5.38%

109 WILTON Road

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%

110 TRAFFORD Drive

CHESTERTOWN, MD

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

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

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%