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.

Townhouses for Sale in Chestertown, MD

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

Showing 2 Townhouse 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
101 S MILL Street CHESTERTOWN, MD This cute as a button downtown stunner is recently updated and ready for the next owner to...	2 beds \| 3 baths \| 1,476 sq.ft.	$515,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 2.95% Airbnb Rental Income: $2063 Traditional Rental Income: $2478 Airbnb ROI: 0.98% Traditional ROI: 2.95%
104 ACORN Drive CHESTERTOWN, MD Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,...	3 beds \| 3 baths \| 1,900 sq.ft.	$284,900	Airbnb cash on cash: 4.53% Traditional cash on cash: 7.06% Airbnb Rental Income: $2463 Traditional Rental Income: $2543 Airbnb ROI: 4.53% Traditional ROI: 7.06%
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: 6.74% Traditional cash on cash: 8.21% Airbnb Rental Income: $3918 Traditional Rental Income: $3607 Airbnb ROI: 6.74% Traditional ROI: 8.21%
213 BYFORD Drive CHESTERTOWN , MD Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was to...	4 beds \| 2 baths \| 1,277 sq.ft.	$380,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 4.94% Airbnb Rental Income: $2778 Traditional Rental Income: $2670 Airbnb ROI: 3.41% Traditional ROI: 4.94%
103 LANDING Lane CHESTERTOWN , MD MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-...	2 beds \| 3 baths \| 2,100 sq.ft.	$499,999	Airbnb cash on cash: -0.81% Traditional cash on cash: 1.84% Airbnb Rental Income: $2063 Traditional Rental Income: $2769 Airbnb ROI: -0.81% Traditional ROI: 1.84%
208 Central Dr CHESTERTOWN , MD Welcome to 208 Central Drive, located in the desirable Chester Harbor community just minut...	3 beds \| 1 baths \| 1,120 sq.ft.	$299,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 4.68% Airbnb Rental Income: $2463 Traditional Rental Income: $1857 Airbnb ROI: 4.7% Traditional ROI: 4.68%
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.	$1,245,500	Airbnb cash on cash: -0.04% Traditional cash on cash: 1.52% Airbnb Rental Income: $3918 Traditional Rental Income: $4880 Airbnb ROI: -0.04% Traditional ROI: 1.52%
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.	$385,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 5.33% Airbnb Rental Income: $2778 Traditional Rental Income: $2650 Airbnb ROI: 3.88% Traditional ROI: 5.33%
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.	$2,200,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 1.61% Airbnb Rental Income: $3918 Traditional Rental Income: $6617 Airbnb ROI: -0.13% Traditional ROI: 1.61%
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: 2.74% Traditional cash on cash: 5.29% Airbnb Rental Income: $2778 Traditional Rental Income: $3316 Airbnb ROI: 2.74% Traditional ROI: 5.29%

Your search for investment property begins and ends here

Townhouses for Sale in Chestertown, MD

101 S MILL Street

CHESTERTOWN, MD

2 beds | 3 baths | 1,476 sq.ft.

$515,000

Airbnb cash on cash: 0.98%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $2063

Traditional Rental Income: $2478

Airbnb ROI: 0.98%

Traditional ROI: 2.95%

104 ACORN Drive

CHESTERTOWN, MD

3 beds | 3 baths | 1,900 sq.ft.

$284,900

Airbnb cash on cash: 4.53%

Traditional cash on cash: 7.06%

Airbnb Rental Income: $2463

Traditional Rental Income: $2543

Airbnb ROI: 4.53%

Traditional ROI: 7.06%

Other Investment Properties for Sale in Chestertown

CHESTERTOWN , MD

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

$384,000

Airbnb cash on cash: 6.74%

Traditional cash on cash: 8.21%

Airbnb Rental Income: $3918

Traditional Rental Income: $3607

Airbnb ROI: 6.74%

Traditional ROI: 8.21%

CHESTERTOWN , MD

4 beds | 2 baths | 1,277 sq.ft.

$380,000

Airbnb cash on cash: 3.41%

Traditional cash on cash: 4.94%

Airbnb Rental Income: $2778

Traditional Rental Income: $2670

Airbnb ROI: 3.41%

Traditional ROI: 4.94%

CHESTERTOWN , MD

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

$499,999

Airbnb cash on cash: -0.81%

Traditional cash on cash: 1.84%

Airbnb Rental Income: $2063

Traditional Rental Income: $2769

Airbnb ROI: -0.81%

Traditional ROI: 1.84%

CHESTERTOWN , MD

3 beds | 1 baths | 1,120 sq.ft.

$299,000

Airbnb cash on cash: 4.7%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $2463

Traditional Rental Income: $1857

Airbnb ROI: 4.7%

Traditional ROI: 4.68%

CHESTERTOWN , MD

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

$1,245,500

Airbnb cash on cash: -0.04%

Traditional cash on cash: 1.52%

Airbnb Rental Income: $3918

Traditional Rental Income: $4880

Airbnb ROI: -0.04%

Traditional ROI: 1.52%

CHESTERTOWN , MD

4 beds | 3 baths | 2,630 sq.ft.

$385,000

Airbnb cash on cash: 3.88%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $2778

Traditional Rental Income: $2650

Airbnb ROI: 3.88%

Traditional ROI: 5.33%

CHESTERTOWN , MD

5 beds | 5 baths | 4,305 sq.ft.

$2,200,000

Airbnb cash on cash: -0.13%