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 5 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 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%
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: 4.57% Traditional cash on cash: 5.09% Airbnb Rental Income: $2892 Traditional Rental Income: $2392 Airbnb ROI: 4.57% Traditional ROI: 5.09%
23110 OLD FAIRLEE Road CHESTERTOWN, MD Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impress...	3 beds \| 1 baths \| 1,805 sq.ft.	$359,900	Airbnb cash on cash: 4.77% Traditional cash on cash: 3.49% Airbnb Rental Income: $2892 Traditional Rental Income: $1791 Airbnb ROI: 4.77% Traditional ROI: 3.49%
8750 GEORGETOWN Road CHESTERTOWN, MD Are you looking for an affordable property with an acre of land, detached garage with elec...	3 beds \| 2 baths \| 1,900 sq.ft.	$339,000	Airbnb cash on cash: 4.86% Traditional cash on cash: 5.75% Airbnb Rental Income: $2892 Traditional Rental Income: $2505 Airbnb ROI: 4.86% Traditional ROI: 5.75%
247 Blakefield Dr CHESTERTOWN, MD Unlock the door to your future with an exclusive offer: Qualify for an exceptional 5.05% f...	3 beds \| 3 baths \| 2,572 sq.ft.	$425,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 5.68% Airbnb Rental Income: $2892 Traditional Rental Income: $3020 Airbnb ROI: 3.67% Traditional ROI: 5.68%

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: 5.01%

Traditional cash on cash: 5.74%

Airbnb Rental Income: $2892

Traditional Rental Income: $2457

Airbnb ROI: 5.01%

Traditional ROI: 5.74%

10751 MILLBROOK DR

CHESTERTOWN, MD

3 beds | 2 baths | N/A

$350,000

Airbnb cash on cash: 4.57%

Traditional cash on cash: 5.09%

Airbnb Rental Income: $2892

Traditional Rental Income: $2392

Airbnb ROI: 4.57%

Traditional ROI: 5.09%

23110 OLD FAIRLEE Road

CHESTERTOWN, MD

3 beds | 1 baths | 1,805 sq.ft.

$359,900

Airbnb cash on cash: 4.77%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $2892

Traditional Rental Income: $1791

Airbnb ROI: 4.77%

Traditional ROI: 3.49%

8750 GEORGETOWN Road

CHESTERTOWN, MD

3 beds | 2 baths | 1,900 sq.ft.

$339,000

Airbnb cash on cash: 4.86%

Traditional cash on cash: 5.75%

Airbnb Rental Income: $2892

Traditional Rental Income: $2505

Airbnb ROI: 4.86%

Traditional ROI: 5.75%

247 Blakefield Dr

CHESTERTOWN, MD

3 beds | 3 baths | 2,572 sq.ft.

$425,000

Airbnb cash on cash: 3.67%

Traditional cash on cash: 5.68%

Airbnb Rental Income: $2892

Traditional Rental Income: $3020

Airbnb ROI: 3.67%

Traditional ROI: 5.68%

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