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 3 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
200 FEY RD CHESTERTOWN, MD Welcome to this charming rancher situated just minutes from historic downtown Chestertown....	3 beds \| 2 baths \| N/A	$374,900	Airbnb cash on cash: 5% Traditional cash on cash: 5.11% Airbnb Rental Income: $3123 Traditional Rental Income: $2450 Airbnb ROI: 5% Traditional ROI: 5.11%
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.	$305,000	Airbnb cash on cash: 6.07% Traditional cash on cash: 4.68% Airbnb Rental Income: $3123 Traditional Rental Income: $2012 Airbnb ROI: 6.07% Traditional ROI: 4.68%
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%
Other Investment Properties for Sale in Chestertown
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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chestertown, MD

200 FEY RD

CHESTERTOWN, MD

3 beds | 2 baths | N/A

$374,900

Airbnb cash on cash: 5%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $3123

Traditional Rental Income: $2450

Airbnb ROI: 5%

Traditional ROI: 5.11%

107 MALONE Avenue

CHESTERTOWN, MD

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

$305,000

Airbnb cash on cash: 6.07%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $3123

Traditional Rental Income: $2012

Airbnb ROI: 6.07%

Traditional ROI: 4.68%

10751 MILLBROOK DR

CHESTERTOWN, MD

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%

Other Investment Properties for Sale in Chestertown

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%

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%

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%

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%

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%

CHESTERTOWN , MD

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

$450,000