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.

Condos for Sale in Chestertown, MD

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

Showing 2 Condo 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
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%
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%
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.	$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.	$409,900	Airbnb cash on cash: 1.78% Traditional cash on cash: 5.79% Airbnb Rental Income: $1948 Traditional Rental Income: $2977 Airbnb ROI: 1.78% Traditional ROI: 5.79%
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%
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%

Your search for investment property begins and ends here

Condos for Sale in Chestertown, MD

103 LANDING Lane

CHESTERTOWN, MD

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%

118 LITTLE HARBOR Way unit: 201 #201

CHESTERTOWN, MD

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%

Other Investment Properties for Sale in Chestertown

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%

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%

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%

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%

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%

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%

CHESTERTOWN , MD

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

$409,900

Airbnb cash on cash: 1.78%