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 1 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 MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-...	2 beds \| 3 baths \| 2,100 sq.ft.	$519,999	Airbnb cash on cash: -1.4% Traditional cash on cash: 1.73% Airbnb Rental Income: $1721 Traditional Rental Income: $2769 Airbnb ROI: -1.4% Traditional ROI: 1.73%
Other Investment Properties for Sale in Chestertown
126 CHAR NOR MANOR Boulevard CHESTERTOWN , MD This charming 3 bedroom, 2 bathroom home offers the perfect blend of comfort, convenience,...	3 beds \| 2 baths \| 1,304 sq.ft.	$349,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 4.75% Airbnb Rental Income: $2059 Traditional Rental Income: $2185 Airbnb ROI: 2.74% Traditional ROI: 4.75%
6746 QUAKER NECK Road CHESTERTOWN , MD	5 beds \| 3 baths \| 3,371 sq.ft.	$384,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 8.21% Airbnb Rental Income: $2925 Traditional Rental Income: $3607 Airbnb ROI: 4.44% 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: 0.36% Traditional cash on cash: 3.3% Airbnb Rental Income: $2028 Traditional Rental Income: $3409 Airbnb ROI: 0.36% Traditional ROI: 3.3%
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: 2.82% Traditional cash on cash: 5.69% Airbnb Rental Income: $2059 Traditional Rental Income: $2457 Airbnb ROI: 2.82% Traditional ROI: 5.69%
21217 TEXAS Avenue CHESTERTOWN , MD MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! ...	2 beds \| 1 baths \| 912 sq.ft.	$265,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 4.09% Airbnb Rental Income: $1721 Traditional Rental Income: $1527 Airbnb ROI: 2.96% Traditional ROI: 4.09%
110 TRAFFORD Drive CHESTERTOWN , MD Coventry Farms-Reduced to Sell, Offers Encouraged Located in the highly desirable Coventry...	4 beds \| 3 baths \| 2,880 sq.ft.	$450,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 5.22% Airbnb Rental Income: $2028 Traditional Rental Income: $3166 Airbnb ROI: 1.27% Traditional ROI: 5.22%
103 TRAFFORD Drive CHESTERTOWN , MD Welcome to 103 Trafford Drive; an exceptionally maintained 3 bedroom home just minutes fro...	3 beds \| 3 baths \| 1,944 sq.ft.	$450,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 3.23% Airbnb Rental Income: $2059 Traditional Rental Income: $2300 Airbnb ROI: 1.4% Traditional ROI: 3.23%
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: 1.98% Traditional cash on cash: 2.68% Airbnb Rental Income: $2059 Traditional Rental Income: $1802 Airbnb ROI: 1.98% Traditional ROI: 2.68%
208 CENTRAL Drive 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: 3.51% Traditional cash on cash: 4.68% Airbnb Rental Income: $2059 Traditional Rental Income: $1857 Airbnb ROI: 3.51% Traditional ROI: 4.68%
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: 2.42% Traditional cash on cash: 3.51% Airbnb Rental Income: $2925 Traditional Rental Income: $2770 Airbnb ROI: 2.42% 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: -0.78% Traditional cash on cash: 1.25% Airbnb Rental Income: $2925 Traditional Rental Income: $4880 Airbnb ROI: -0.78% Traditional ROI: 1.25%
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: 2.69% Traditional cash on cash: 5.15% Airbnb Rental Income: $2028 Traditional Rental Income: $2284 Airbnb ROI: 2.69% Traditional ROI: 5.15%
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: 6.99% Traditional cash on cash: 11.51% Airbnb Rental Income: $1721 Traditional Rental Income: $1811 Airbnb ROI: 6.99% Traditional ROI: 11.51%
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: 2.15% Traditional cash on cash: 5.33% Airbnb Rental Income: $2028 Traditional Rental Income: $2650 Airbnb ROI: 2.15% Traditional ROI: 5.33%

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.

$519,999

Airbnb cash on cash: -1.4%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $1721

Traditional Rental Income: $2769

Airbnb ROI: -1.4%

Traditional ROI: 1.73%

Other Investment Properties for Sale in Chestertown

CHESTERTOWN , MD

3 beds | 2 baths | 1,304 sq.ft.

$349,000

Airbnb cash on cash: 2.74%

Traditional cash on cash: 4.75%

Airbnb Rental Income: $2059

Traditional Rental Income: $2185

Airbnb ROI: 2.74%

Traditional ROI: 4.75%

CHESTERTOWN , MD

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

$384,000

Airbnb cash on cash: 4.44%

Traditional cash on cash: 8.21%

Airbnb Rental Income: $2925

Traditional Rental Income: $3607

Airbnb ROI: 4.44%

Traditional ROI: 8.21%

CHESTERTOWN , MD

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

$695,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $2028

Traditional Rental Income: $3409

Airbnb ROI: 0.36%

Traditional ROI: 3.3%

CHESTERTOWN , MD

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

$344,900

Airbnb cash on cash: 2.82%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $2059

Traditional Rental Income: $2457

Airbnb ROI: 2.82%

Traditional ROI: 5.69%

CHESTERTOWN , MD

2 beds | 1 baths | 912 sq.ft.

$265,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $1721

Traditional Rental Income: $1527

Airbnb ROI: 2.96%

Traditional ROI: 4.09%

CHESTERTOWN , MD

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

$450,000

Airbnb cash on cash: 1.27%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $2028

Traditional Rental Income: $3166

Airbnb ROI: 1.27%

Traditional ROI: 5.22%

CHESTERTOWN , MD

3 beds | 3 baths | 1,944 sq.ft.

$450,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $2059

Traditional Rental Income: $2300

Airbnb ROI: 1.4%

Traditional ROI: 3.23%

CHESTERTOWN , MD

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

$419,900

Airbnb cash on cash: 1.98%

Traditional cash on cash: 2.68%