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
200 WASHINGTON Avenue CHESTERTOWN, MD Only 500 steps from the center of Chestertown (5-minute walk) to this early 20th C gem of ...	4 beds \| 4 baths \| 2,917 sq.ft.	$695,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 3.38% Airbnb Rental Income: $1948 Traditional Rental Income: $3655 Airbnb ROI: -0.05% Traditional ROI: 3.38%
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.	$515,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 5.31% Airbnb Rental Income: $1948 Traditional Rental Income: $3673 Airbnb ROI: 0.66% Traditional ROI: 5.31%
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.	$770,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 2.89% Airbnb Rental Income: $1948 Traditional Rental Income: $3409 Airbnb ROI: 0.13% Traditional ROI: 2.89%
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%
108 S KENT Street CHESTERTOWN, MD Price improvement! Cute as a button in the historic district on South Kent St. This 1-bedr...	1 beds \| 2 baths \| 936 sq.ft.	$315,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 4.09% Airbnb Rental Income: $1456 Traditional Rental Income: $1867 Airbnb ROI: 1.24% Traditional ROI: 4.09%
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%
165 CHAR NOR MANOR Boulevard CHESTERTOWN, MD Chester River Views from Every Angle! Welcome to this stunning Colonial located on the Que...	4 beds \| 3 baths \| 2,258 sq.ft.	$429,999	Airbnb cash on cash: 1.65% Traditional cash on cash: 5.48% Airbnb Rental Income: $1948 Traditional Rental Income: $2977 Airbnb ROI: 1.65% Traditional ROI: 5.48%
107 MALONE Avenue CHESTERTOWN, MD Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to c...	3 beds \| 1 baths \| 1,200 sq.ft.	$290,000	Airbnb cash on cash: 5.73% Traditional cash on cash: 4.96% Airbnb Rental Income: $2892 Traditional Rental Income: $2012 Airbnb ROI: 5.73% Traditional ROI: 4.96%
8833 GEORGETOWN Road CHESTERTOWN, MD Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,60...	4 beds \| 2 baths \| 1,625 sq.ft.	$364,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 6.14% Airbnb Rental Income: $1948 Traditional Rental Income: $2627 Airbnb ROI: 2.64% Traditional ROI: 6.14%
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.	$539,999	Airbnb cash on cash: -0.93% Traditional cash on cash: 1.63% Airbnb Rental Income: $1999 Traditional Rental Income: $2769 Airbnb ROI: -0.93% Traditional ROI: 1.63%
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%
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.	$449,900	Airbnb cash on cash: 3.43% Traditional cash on cash: 2.44% Airbnb Rental Income: $2892 Traditional Rental Income: $1802 Airbnb ROI: 3.43% Traditional ROI: 2.44%
116 HARLAN Loop CHESTERTOWN, MD $$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$ Welcome to Cove...	5 beds \| 4 baths \| 4,067 sq.ft.	$519,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 3.42% Airbnb Rental Income: $3223 Traditional Rental Income: $2770 Airbnb ROI: 2.86% Traditional ROI: 3.42%
11040 KYLIE Lane CHESTERTOWN, MD Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 ac...	4 beds \| 4 baths \| 3,684 sq.ft.	$649,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 5.36% Airbnb Rental Income: $1948 Traditional Rental Income: $4493 Airbnb ROI: 0.31% Traditional ROI: 5.36%
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%
201 BIRCH RUN Road CHESTERTOWN, MD This Mid Century Modern is located in Mile Tree Village, one of Chestertown's most coveted...	3 beds \| 2 baths \| 1,588 sq.ft.	$470,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 4.34% Airbnb Rental Income: $2892 Traditional Rental Income: $2896 Airbnb ROI: 2.81% Traditional ROI: 4.34%
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.	$399,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 4.25% Airbnb Rental Income: $1948 Traditional Rental Income: $2284 Airbnb ROI: 1.98% Traditional ROI: 4.25%
112 METCALF Road CHESTERTOWN, MD Come enjoy the this 2 year old home in Historic Chestertown. The home features 3 full bedr...	3 beds \| 2 baths \| 1,280 sq.ft.	$249,950	Airbnb cash on cash: 6.64% Traditional cash on cash: 7.05% Airbnb Rental Income: $2892 Traditional Rental Income: $2320 Airbnb ROI: 6.64% Traditional ROI: 7.05%
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%
515 N KENT Street CHESTERTOWN, MD Welcome to 515 N Kent Street in the heart of Chestertown! This charming two story home fea...	4 beds \| 2 baths \| 2,220 sq.ft.	$499,900	Airbnb cash on cash: 1.15% Traditional cash on cash: 4.44% Airbnb Rental Income: $1948 Traditional Rental Income: $2974 Airbnb ROI: 1.15% Traditional ROI: 4.44%
10751 MILLBROOK DR CHESTERTOWN, MD Chesapeake Landing - This home is featured on a corner lot with large living space and add...	3 beds \| 2 baths \| N/A	$350,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 5.09% Airbnb Rental Income: $2892 Traditional Rental Income: $2392 Airbnb ROI: 4.57% Traditional ROI: 5.09%
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.	$179,000	Airbnb cash on cash: 5.84% Traditional cash on cash: 8.18% Airbnb Rental Income: $1999 Traditional Rental Income: $1876 Airbnb ROI: 5.84% Traditional ROI: 8.18%
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.	$359,900	Airbnb cash on cash: 4.77% Traditional cash on cash: 3.49% Airbnb Rental Income: $2892 Traditional Rental Income: $1791 Airbnb ROI: 4.77% Traditional ROI: 3.49%
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%
118 LITTLE HARBOR Way unit: 201 #201 CHESTERTOWN, MD An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo fe...	2 beds \| 3 baths \| 1,550 sq.ft.	$675,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.85% Airbnb Rental Income: $1999 Traditional Rental Income: $3219 Airbnb ROI: 0.08% Traditional ROI: 2.85%
112 SILVER HEEL Road CHESTERTOWN, MD Welcome to this stunning 2023 built home - a move-in ready, three-story residence offering...	5 beds \| 4 baths \| 2,615 sq.ft.	$374,900	Airbnb cash on cash: 4.37% Traditional cash on cash: 7.03% Airbnb Rental Income: $3223 Traditional Rental Income: $3434 Airbnb ROI: 4.37% Traditional ROI: 7.03%
8750 GEORGETOWN Road CHESTERTOWN, MD Are you looking for an affordable property with an acre of land, detached garage with elec...	3 beds \| 2 baths \| 1,900 sq.ft.	$339,000	Airbnb cash on cash: 4.86% Traditional cash on cash: 5.75% Airbnb Rental Income: $2892 Traditional Rental Income: $2505 Airbnb ROI: 4.86% Traditional ROI: 5.75%
247 Blakefield Dr CHESTERTOWN, MD Unlock the door to your future with an exclusive offer: Qualify for an exceptional 5.05% f...	3 beds \| 3 baths \| 2,572 sq.ft.	$425,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 5.68% Airbnb Rental Income: $2892 Traditional Rental Income: $3020 Airbnb ROI: 3.67% Traditional ROI: 5.68%
8951 ORCHARD Drive CHESTERTOWN, MD Nestled in the serene Orchard Hill community, this stunning Craftsman-Colonial offers 3,73...	4 beds \| 4 baths \| 3,735 sq.ft.	$695,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 3.67% Airbnb Rental Income: $1948 Traditional Rental Income: $3637 Airbnb ROI: 0.27% Traditional ROI: 3.67%
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%
318 LINCOLN CHESTERTOWN, MD Kent County welcomes you with a move-in ready home that's full of updates! This 3-bedroom,...	3 beds \| 2 baths \| 960 sq.ft.	$269,000	Airbnb cash on cash: 6.41% Traditional cash on cash: 6.29% Airbnb Rental Income: $2892 Traditional Rental Income: $2190 Airbnb ROI: 6.41% Traditional ROI: 6.29%
112 SILVER HEEL Drive CHESTERTOWN, MD Welcome to this stunning 2023 built home - a move-in ready, three-story residence offering...	5 beds \| 4 baths \| 2,615 sq.ft.	$369,900	Airbnb cash on cash: 4.66% Traditional cash on cash: 6.8% Airbnb Rental Income: $3223 Traditional Rental Income: $3238 Airbnb ROI: 4.66% Traditional ROI: 6.8%
101 METCALF Road CHESTERTOWN, MD Brand new home in Historic Chestertown available for move-in this Right Now. This home fea...	3 beds \| 2 baths \| 1,280 sq.ft.	$264,900	Airbnb cash on cash: 7.3% Traditional cash on cash: 7.01% Airbnb Rental Income: $2892 Traditional Rental Income: $2150 Airbnb ROI: 7.3% Traditional ROI: 7.01%
10781 FERMOY Road CHESTERTOWN, MD Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Lan...	3 beds \| 3 baths \| 2,160 sq.ft.	$449,900	Airbnb cash on cash: 3.53% Traditional cash on cash: 5.03% Airbnb Rental Income: $2892 Traditional Rental Income: $2850 Airbnb ROI: 3.53% Traditional ROI: 5.03%
108 FLYING CLOUD Drive CHESTERTOWN, MD Beautifully done! A MUST see! UPGRADED 2023-built Smart Home, tucked into a quiet and frie...	4 beds \| 3 baths \| 1,936 sq.ft.	$375,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 5.76% Airbnb Rental Income: $1948 Traditional Rental Income: $2892 Airbnb ROI: 1.61% Traditional ROI: 5.76%
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.	$370,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 5.29% Airbnb Rental Income: $2892 Traditional Rental Income: $2608 Airbnb ROI: 4.17% Traditional ROI: 5.29%
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 Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on...	3 beds \| 3 baths \| 2,034 sq.ft.	$399,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 6.04% Airbnb Rental Income: $2892 Traditional Rental Income: $2995 Airbnb ROI: 3.97% Traditional ROI: 6.04%

Real Estate investment in Chestertown, MD

There are 40 properties for sale in the city of Chestertown . The median list price in Chestertown is $399,000 and the average price per square foot is $180. In December 2025, the average monthly cash on cash return in Chestertown is 5.00%. The average monthly rental income in Chestertown is $2,770.

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

There are 40 investment properties available for sale in Chestertown.

In 2025, 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 $2,770.

Your search for investment property begins and ends here

Investment Property for Sale in Chestertown, MD

200 WASHINGTON Avenue

CHESTERTOWN, MD

4 beds | 4 baths | 2,917 sq.ft.

$695,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $1948

Traditional Rental Income: $3655

Airbnb ROI: -0.05%

Traditional ROI: 3.38%

100 ADELA Way

CHESTERTOWN, MD

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

$515,000

Airbnb cash on cash: 0.66%

Traditional cash on cash: 5.31%

Airbnb Rental Income: $1948

Traditional Rental Income: $3673

Airbnb ROI: 0.66%

Traditional ROI: 5.31%

7844 CHESTER Court

CHESTERTOWN, MD

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

$770,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $1948

Traditional Rental Income: $3409

Airbnb ROI: 0.13%

Traditional ROI: 2.89%

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%

108 S KENT Street

CHESTERTOWN, MD

1 beds | 2 baths | 936 sq.ft.

$315,000

Airbnb cash on cash: 1.24%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $1456

Traditional Rental Income: $1867

Airbnb ROI: 1.24%

Traditional ROI: 4.09%

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%

165 CHAR NOR MANOR Boulevard

CHESTERTOWN, MD

4 beds | 3 baths | 2,258 sq.ft.

$429,999

Airbnb cash on cash: 1.65%

Traditional cash on cash: 5.48%

Airbnb Rental Income: $1948

Traditional Rental Income: $2977

Airbnb ROI: 1.65%

Traditional ROI: 5.48%

107 MALONE Avenue

CHESTERTOWN, MD

3 beds | 1 baths | 1,200 sq.ft.

$290,000

Airbnb cash on cash: 5.73%

Traditional cash on cash: 4.96%

Airbnb Rental Income: $2892

Traditional Rental Income: $2012

Airbnb ROI: 5.73%