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.	$499,999	Airbnb cash on cash: -1.77% Traditional cash on cash: 1.84% Airbnb Rental Income: $1524 Traditional Rental Income: $2769 Airbnb ROI: -1.77% Traditional ROI: 1.84%
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: 5.93% Traditional cash on cash: 8.21% Airbnb Rental Income: $3568 Traditional Rental Income: $3607 Airbnb ROI: 5.93% Traditional ROI: 8.21%
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: 0.05% Traditional cash on cash: 2.95% Airbnb Rental Income: $1524 Traditional Rental Income: $2478 Airbnb ROI: 0.05% Traditional ROI: 2.95%
109 Wilton Rd 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: 3.82% Traditional cash on cash: 5.69% Airbnb Rental Income: $2448 Traditional Rental Income: $2457 Airbnb ROI: 3.82% 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.	$244,500	Airbnb cash on cash: 2.57% Traditional cash on cash: 4.5% Airbnb Rental Income: $1524 Traditional Rental Income: $1527 Airbnb ROI: 2.57% Traditional ROI: 4.5%
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: 1.79% Traditional cash on cash: 5.22% Airbnb Rental Income: $2288 Traditional Rental Income: $3166 Airbnb ROI: 1.79% Traditional ROI: 5.22%
9816 FAIRLEE RD CHESTERTOWN , MD Welcome to 9816 Fairlee Road. Be Sure to Click the Virtual Tour!! This property has been m...	3 beds \| 3 baths \| N/A	$535,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 2.64% Airbnb Rental Income: $2448 Traditional Rental Income: $2246 Airbnb ROI: 1.85% Traditional ROI: 2.64%
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: 2.27% Traditional cash on cash: 4.94% Airbnb Rental Income: $2288 Traditional Rental Income: $2670 Airbnb ROI: 2.27% Traditional ROI: 4.94%
103 TRAFFORD Drive CHESTERTOWN , MD PRICE IMPROVEMENT: Priced below 2025 Appraisal!! Instant equity! NOTE: Zillow's property t...	3 beds \| 3 baths \| 1,944 sq.ft.	$399,900	Airbnb cash on cash: 2.56% Traditional cash on cash: 3.76% Airbnb Rental Income: $2448 Traditional Rental Income: $2300 Airbnb ROI: 2.56% Traditional ROI: 3.76%

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.

$499,999

Airbnb cash on cash: -1.77%

Traditional cash on cash: 1.84%

Airbnb Rental Income: $1524

Traditional Rental Income: $2769

Airbnb ROI: -1.77%

Traditional ROI: 1.84%

Other Investment Properties for Sale in Chestertown

CHESTERTOWN , MD

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

$384,000

Airbnb cash on cash: 5.93%

Traditional cash on cash: 8.21%

Airbnb Rental Income: $3568

Traditional Rental Income: $3607

Airbnb ROI: 5.93%

Traditional ROI: 8.21%

CHESTERTOWN , MD

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

$515,000

Airbnb cash on cash: 0.05%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $1524

Traditional Rental Income: $2478

Airbnb ROI: 0.05%

Traditional ROI: 2.95%

CHESTERTOWN , MD

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

$344,900

Airbnb cash on cash: 3.82%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $2448

Traditional Rental Income: $2457

Airbnb ROI: 3.82%

Traditional ROI: 5.69%

CHESTERTOWN , MD

2 beds | 1 baths | 912 sq.ft.

$244,500

Airbnb cash on cash: 2.57%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $1524

Traditional Rental Income: $1527

Airbnb ROI: 2.57%

Traditional ROI: 4.5%

CHESTERTOWN , MD

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

$450,000

Airbnb cash on cash: 1.79%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $2288

Traditional Rental Income: $3166

Airbnb ROI: 1.79%

Traditional ROI: 5.22%

CHESTERTOWN , MD

3 beds | 3 baths | N/A

$535,000

Airbnb cash on cash: 1.85%

Traditional cash on cash: 2.64%

Airbnb Rental Income: $2448

Traditional Rental Income: $2246

Airbnb ROI: 1.85%

Traditional ROI: 2.64%

CHESTERTOWN , MD

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

$380,000

Airbnb cash on cash: 2.27%

Traditional cash on cash: 4.94%

Airbnb Rental Income: $2288

Traditional Rental Income: $2670

Airbnb ROI: 2.27%

Traditional ROI: 4.94%

CHESTERTOWN , MD

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

$399,900

Airbnb cash on cash: 2.56%

Traditional cash on cash: 3.76%