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 4 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
109 WILTON Road CHESTERTOWN, MD Charming 3-bedroom, 2-bath rancher in the desirable Chester Harbor community. Situated on ...	3 beds \| 2 baths \| 1,392 sq.ft.	$344,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.69% Airbnb Rental Income: $null Traditional Rental Income: $2457 Airbnb ROI: N/A Traditional ROI: 5.69%
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.	$339,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.15% Airbnb Rental Income: $null Traditional Rental Income: $2284 Airbnb ROI: N/A Traditional ROI: 5.15%
Other Investment Properties for Sale in Chestertown
6746 QUAKER NECK Road CHESTERTOWN , MD	5 beds \| 3 baths \| 3,371 sq.ft.	$384,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.21% Airbnb Rental Income: $null Traditional Rental Income: $3607 Airbnb ROI: N/A Traditional ROI: 8.21%
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.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $3409 Airbnb ROI: N/A Traditional ROI: 3.3%
110 TRAFFORD Drive CHESTERTOWN , MD Here's the opportunity buyers wait for. A classic Colonial in sought-after Coventry Farms,...	4 beds \| 3 baths \| 2,880 sq.ft.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.03% Airbnb Rental Income: $null Traditional Rental Income: $3166 Airbnb ROI: N/A Traditional ROI: 5.03%
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.	$519,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.73% Airbnb Rental Income: $null Traditional Rental Income: $2769 Airbnb ROI: N/A Traditional ROI: 1.73%
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.	$419,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.68% Airbnb Rental Income: $null Traditional Rental Income: $1802 Airbnb ROI: N/A Traditional ROI: 2.68%
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: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $2770 Airbnb ROI: N/A Traditional ROI: 3.51%
105 HIGH Street CHESTERTOWN , MD Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one ...	5 beds \| 5 baths \| 3,243 sq.ft.	$1,395,500	Airbnb cash on cash: N/A Traditional cash on cash: 1.25% Airbnb Rental Income: $null Traditional Rental Income: $4880 Airbnb ROI: N/A Traditional ROI: 1.25%
201 BIRCH RUN Road CHESTERTOWN , MD ***PRICED $30,000 UNDER THE RECENT APPRAISED VALUE*** One floor living, a wood burning...	3 beds \| 2 baths \| 1,588 sq.ft.	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.77% Airbnb Rental Income: $null Traditional Rental Income: $2896 Airbnb ROI: N/A Traditional ROI: 4.77%
234 N COLLEGE Avenue CHESTERTOWN , MD Investor Special - Charming Colonial in Prime Chestertown Location! Welcome to 234 N Colle...	2 beds \| 1 baths \| 1,296 sq.ft.	$130,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.51% Airbnb Rental Income: $null Traditional Rental Income: $1811 Airbnb ROI: N/A Traditional ROI: 11.51%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chestertown, MD

109 WILTON Road

CHESTERTOWN, MD

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

$344,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.69%

Airbnb Rental Income: $null

Traditional Rental Income: $2457

Airbnb ROI: N/A

Traditional ROI: 5.69%

304 HADAWAY Drive

CHESTERTOWN, MD

4 beds | 2 baths | 1,325 sq.ft.

$339,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.15%

Airbnb Rental Income: $null

Traditional Rental Income: $2284

Airbnb ROI: N/A

Traditional ROI: 5.15%

Other Investment Properties for Sale in Chestertown

CHESTERTOWN , MD

5 beds | 3 baths | 3,371 sq.ft.

$384,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.21%

Airbnb Rental Income: $null

Traditional Rental Income: $3607

Airbnb ROI: N/A

Traditional ROI: 8.21%

CHESTERTOWN , MD

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

$695,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.3%

Airbnb Rental Income: $null

Traditional Rental Income: $3409

Airbnb ROI: N/A

Traditional ROI: 3.3%

CHESTERTOWN , MD

4 beds | 3 baths | 2,880 sq.ft.

$465,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.03%

Airbnb Rental Income: $null

Traditional Rental Income: $3166

Airbnb ROI: N/A

Traditional ROI: 5.03%

CHESTERTOWN , MD

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

$519,999

Airbnb cash on cash: N/A

Traditional cash on cash: 1.73%

Airbnb Rental Income: $null

Traditional Rental Income: $2769

Airbnb ROI: N/A

Traditional ROI: 1.73%

CHESTERTOWN , MD

3 beds | 3 baths | 1,216 sq.ft.

$419,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.68%

Airbnb Rental Income: $null

Traditional Rental Income: $1802

Airbnb ROI: N/A

Traditional ROI: 2.68%

CHESTERTOWN , MD

5 beds | 4 baths | 4,067 sq.ft.

$509,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.51%

Airbnb Rental Income: $null

Traditional Rental Income: $2770

Airbnb ROI: N/A

Traditional ROI: 3.51%

CHESTERTOWN , MD

5 beds | 5 baths | 3,243 sq.ft.

$1,395,500

Airbnb cash on cash: N/A