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.	$745,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 3.09% Airbnb Rental Income: $2080 Traditional Rental Income: $3655 Airbnb ROI: 0.05% Traditional ROI: 3.09%
124 CHAR NOR MANOR Boulevard CHESTERTOWN, MD Welcome to 124 Char Nor Manor Blvd, a charming home tucked away on a quiet street in Chest...	2 beds \| 2 baths \| 1,024 sq.ft.	$245,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 6.17% Airbnb Rental Income: $2057 Traditional Rental Income: $1893 Airbnb ROI: 4.58% Traditional ROI: 6.17%
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.	$349,900	Airbnb cash on cash: 5.51% Traditional cash on cash: 5.64% Airbnb Rental Income: $3123 Traditional Rental Income: $2457 Airbnb ROI: 5.51% Traditional ROI: 5.64%
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: 1.16% Traditional cash on cash: 4.09% Airbnb Rental Income: $1425 Traditional Rental Income: $1867 Airbnb ROI: 1.16% Traditional ROI: 4.09%
251 DEVON Drive CHESTERTOWN, MD Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When ente...	3 beds \| 3 baths \| 3,935 sq.ft.	$595,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 2.77% Airbnb Rental Income: $3123 Traditional Rental Income: $2834 Airbnb ROI: 2.02% 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.	$450,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 5.2% Airbnb Rental Income: $2080 Traditional Rental Income: $2977 Airbnb ROI: 1.8% Traditional ROI: 5.2%
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.	$314,000	Airbnb cash on cash: 3.59% Traditional cash on cash: 7.25% Airbnb Rental Income: $2080 Traditional Rental Income: $2627 Airbnb ROI: 3.59% Traditional ROI: 7.25%
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.	$559,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 1.54% Airbnb Rental Income: $2057 Traditional Rental Income: $2769 Airbnb ROI: -0.84% Traditional ROI: 1.54%
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: 6.29% Traditional cash on cash: 5.08% Airbnb Rental Income: $3123 Traditional Rental Income: $2055 Airbnb ROI: 6.29% Traditional ROI: 5.08%
10761 KASOTA Road CHESTERTOWN, MD Elevated coastal elegance is displayed in this waterfront perched on the banks of Mill Cre...	3 beds \| 3 baths \| 2,582 sq.ft.	$895,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 1.2% Airbnb Rental Income: $3123 Traditional Rental Income: $2468 Airbnb ROI: 1.13% Traditional ROI: 1.2%
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.	$529,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 3.34% Airbnb Rental Income: $3216 Traditional Rental Income: $2770 Airbnb ROI: 2.78% Traditional ROI: 3.34%
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: 0.49% Traditional cash on cash: 5.36% Airbnb Rental Income: $2080 Traditional Rental Income: $4493 Airbnb ROI: 0.49% Traditional ROI: 5.36%
105 HIGH Street CHESTERTOWN, MD ***Photos reflect the progress as of 3 months ago. The property is now nearly completed an...	5 beds \| 5 baths \| 3,243 sq.ft.	$1,395,500	Airbnb cash on cash: 0.27% Traditional cash on cash: 2.11% Airbnb Rental Income: $3216 Traditional Rental Income: $4880 Airbnb ROI: 0.27% Traditional ROI: 2.11%
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: 3.25% Traditional cash on cash: 4.34% Airbnb Rental Income: $3123 Traditional Rental Income: $2896 Airbnb ROI: 3.25% Traditional ROI: 4.34%
206 S WATER Street CHESTERTOWN, MD Live in the heart of Chestertown's thriving Historic District and see your boat from your ...	4 beds \| 4 baths \| 2,008 sq.ft.	$648,750	Airbnb cash on cash: 0.21% Traditional cash on cash: 2.87% Airbnb Rental Income: $2080 Traditional Rental Income: $3155 Airbnb ROI: 0.21% Traditional ROI: 2.87%
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.	$255,000	Airbnb cash on cash: 7.29% Traditional cash on cash: 6.9% Airbnb Rental Income: $3123 Traditional Rental Income: $2320 Airbnb ROI: 7.29% Traditional ROI: 6.9%
600 ROSIN Drive CHESTERTOWN, MD Charming 3-bedroom, 2-bathroom waterfront cottage nestled along the peaceful shores of Ros...	3 beds \| 2 baths \| 1,300 sq.ft.	$415,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 5.65% Airbnb Rental Income: $3123 Traditional Rental Income: $2889 Airbnb ROI: 4.43% Traditional ROI: 5.65%
907 N MEADOWVIEW Drive CHESTERTOWN, MD JUST INSTALLED BRAND NEW CARPET! Welcome to 907 N Meadowview Drive, a beautifully maintain...	3 beds \| 3 baths \| 1,842 sq.ft.	$410,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 5.13% Airbnb Rental Income: $3123 Traditional Rental Income: $2720 Airbnb ROI: 4.33% Traditional ROI: 5.13%
492 PEAR TREE POINT Road CHESTERTOWN, MD Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with uni...	3 beds \| 2 baths \| 2,632 sq.ft.	$920,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 1.57% Airbnb Rental Income: $3123 Traditional Rental Income: $2865 Airbnb ROI: 1.05% Traditional ROI: 1.57%
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.	$350,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 5.96% Airbnb Rental Income: $2080 Traditional Rental Income: $2650 Airbnb ROI: 2.6% Traditional ROI: 5.96%
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: 1.38% Traditional cash on cash: 4.44% Airbnb Rental Income: $2080 Traditional Rental Income: $2974 Airbnb ROI: 1.38% 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: 5.15% Traditional cash on cash: 5.09% Airbnb Rental Income: $3123 Traditional Rental Income: $2392 Airbnb ROI: 5.15% 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: 6.13% Traditional cash on cash: 8.18% Airbnb Rental Income: $2057 Traditional Rental Income: $1876 Airbnb ROI: 6.13% Traditional ROI: 8.18%
7989 QUAKER NECK Road CHESTERTOWN, MD Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this ...	5 beds \| 5 baths \| 4,305 sq.ft.	$2,750,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.09% Airbnb Rental Income: $3216 Traditional Rental Income: $6617 Airbnb ROI: -0.53% Traditional ROI: 1.09%
23110 OLD FAIRLEE Road CHESTERTOWN, MD Renovated Ranch Home in Fairlee. This home has been updated top to bottom. Recent updates ...	3 beds \| 1 baths \| 1,805 sq.ft.	$369,900	Airbnb cash on cash: 5.17% Traditional cash on cash: 3.37% Airbnb Rental Income: $3123 Traditional Rental Income: $1791 Airbnb ROI: 5.17% Traditional ROI: 3.37%
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: 7.38% Traditional cash on cash: 6.24% Airbnb Rental Income: $3123 Traditional Rental Income: $2133 Airbnb ROI: 7.38% 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.	$695,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 2.74% Airbnb Rental Income: $2057 Traditional Rental Income: $3219 Airbnb ROI: 0.13% Traditional ROI: 2.74%
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: 4.35% Traditional cash on cash: 7.03% Airbnb Rental Income: $3216 Traditional Rental Income: $3434 Airbnb ROI: 4.35% Traditional ROI: 7.03%
517 HIGH Street CHESTERTOWN, MD Fantastic investment opportunity. Highly sought after downtown Historic Chestertown. This ...	N/A beds \| N/A baths \| 1,728 sq.ft.	$389,900	Airbnb cash on cash: 1.9% Traditional cash on cash: 2.89% Airbnb Rental Income: $1912 Traditional Rental Income: $1767 Airbnb ROI: 1.9% Traditional ROI: 2.89%
126 METCALF Road CHESTERTOWN, MD Amazing deal on this 2 yr old duplex/rancher with no stairs that shows like new. Owners mo...	3 beds \| 2 baths \| 1,140 sq.ft.	$230,000	Airbnb cash on cash: 8.27% Traditional cash on cash: 7.21% Airbnb Rental Income: $3123 Traditional Rental Income: $2184 Airbnb ROI: 8.27% Traditional ROI: 7.21%
206 VALLEY CHESTERTOWN, MD Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge f...	4 beds \| 2 baths \| 2,869 sq.ft.	$639,900	Airbnb cash on cash: 0.57% Traditional cash on cash: 2.64% Airbnb Rental Income: $2080 Traditional Rental Income: $2782 Airbnb ROI: 0.57% Traditional ROI: 2.64%
10050 FORREST Lane CHESTERTOWN, MD Serene Waterfront Retreat on Fairlee Creek is nestled in the tranquil woods of a private c...	4 beds \| 2 baths \| 1,820 sq.ft.	$899,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 1.72% Airbnb Rental Income: $2080 Traditional Rental Income: $2956 Airbnb ROI: 0.04% Traditional ROI: 1.72%
8750 GEORGETOWN Road CHESTERTOWN, MD Are you looking for a property with an acre of land, detached garage with electric, public...	3 beds \| 2 baths \| 1,900 sq.ft.	$339,000	Airbnb cash on cash: 5.47% Traditional cash on cash: 5.75% Airbnb Rental Income: $3123 Traditional Rental Income: $2505 Airbnb ROI: 5.47% Traditional ROI: 5.75%

Real Estate investment in Chestertown, MD

There are 33 properties for sale in the city of Chestertown . The median list price in Chestertown is $410,000 and the average price per square foot is $196. In October 2025, the average monthly cash on cash return in Chestertown is 5.00%. The average monthly rental income in Chestertown is $2,685.

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

There are 33 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 $2,685.

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.

$745,000

Airbnb cash on cash: 0.05%

Traditional cash on cash: 3.09%

Airbnb Rental Income: $2080

Traditional Rental Income: $3655

Airbnb ROI: 0.05%

Traditional ROI: 3.09%

124 CHAR NOR MANOR Boulevard

CHESTERTOWN, MD

2 beds | 2 baths | 1,024 sq.ft.

$245,000

Airbnb cash on cash: 4.58%

Traditional cash on cash: 6.17%

Airbnb Rental Income: $2057

Traditional Rental Income: $1893

Airbnb ROI: 4.58%

Traditional ROI: 6.17%

109 WILTON Road

CHESTERTOWN, MD

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

$349,900

Airbnb cash on cash: 5.51%

Traditional cash on cash: 5.64%

Airbnb Rental Income: $3123

Traditional Rental Income: $2457

Airbnb ROI: 5.51%

Traditional ROI: 5.64%

108 S KENT Street

CHESTERTOWN, MD

1 beds | 2 baths | 936 sq.ft.

$315,000

Airbnb cash on cash: 1.16%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $1425

Traditional Rental Income: $1867

Airbnb ROI: 1.16%

Traditional ROI: 4.09%

251 DEVON Drive

CHESTERTOWN, MD

3 beds | 3 baths | 3,935 sq.ft.

$595,000

Airbnb cash on cash: 2.02%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $3123

Traditional Rental Income: $2834

Airbnb ROI: 2.02%

Traditional ROI: 2.77%

165 CHAR NOR MANOR Boulevard

CHESTERTOWN, MD

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

$450,000

Airbnb cash on cash: 1.8%

Traditional cash on cash: 5.2%

Airbnb Rental Income: $2080

Traditional Rental Income: $2977

Airbnb ROI: 1.8%

Traditional ROI: 5.2%

8833 GEORGETOWN Road

CHESTERTOWN, MD

4 beds | 2 baths | 1,625 sq.ft.

$314,000

Airbnb cash on cash: 3.59%

Traditional cash on cash: 7.25%

Airbnb Rental Income: $2080

Traditional Rental Income: $2627

Airbnb ROI: 3.59%

Traditional ROI: 7.25%

103 LANDING Lane

CHESTERTOWN, MD

2 beds | 3 baths | 2,100 sq.ft.

$559,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: 1.54%

Airbnb Rental Income: $2057

Traditional Rental Income: $2769

Airbnb ROI: -0.84%