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 7 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
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: 0.75% Traditional cash on cash: 2.64% Airbnb Rental Income: $1788 Traditional Rental Income: $2246 Airbnb ROI: 0.75% Traditional ROI: 2.64%
2032 PONDTOWN RD CHESTERTOWN, MD Meticulously maintained and full of charm, this delightful three-bedroom, two-bath rambler...	3 beds \| 2 baths \| N/A	$325,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 5.59% Airbnb Rental Income: $1788 Traditional Rental Income: $2290 Airbnb ROI: 2.35% Traditional ROI: 5.59%
136 HILLTOP DR CHESTERTOWN, MD Immaculate 3-bedroom, 2-bath home set on a breathtaking, oversized lot with exquisite matu...	3 beds \| 2 baths \| N/A	$366,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 5.07% Airbnb Rental Income: $1788 Traditional Rental Income: $2414 Airbnb ROI: 1.83% Traditional ROI: 5.07%
8706 ELM Road CHESTERTOWN, MD Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroo...	3 beds \| 2 baths \| 1,232 sq.ft.	$320,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 5.71% Airbnb Rental Income: $1788 Traditional Rental Income: $2270 Airbnb ROI: 2.49% Traditional ROI: 5.71%
215 FAIRVIEW DR CHESTERTOWN, MD Beautiful, Well-Maintained 3BR/2.5BA Home with Upgrades - 215 Fairview Drive Owner pride ...	3 beds \| 3 baths \| N/A	$425,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 5.32% Airbnb Rental Income: $1788 Traditional Rental Income: $2790 Airbnb ROI: 1.58% Traditional ROI: 5.32%
8629 AIRY HILL Road CHESTERTOWN, MD Well maintained Beautiful Brick Rancher nestled on 2.16 Acres in Chestertown and a short d...	3 beds \| 2 baths \| 1,440 sq.ft.	$425,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 4.99% Airbnb Rental Income: $1788 Traditional Rental Income: $2698 Airbnb ROI: 1.48% Traditional ROI: 4.99%
240 MERGANSER Drive CHESTERTOWN, MD Practically brand new and just 2 years young, this beautifully maintained home is perfectl...	3 beds \| 2 baths \| 1,120 sq.ft.	$425,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 3.38% Airbnb Rental Income: $1788 Traditional Rental Income: $2120 Airbnb ROI: 1.32% Traditional ROI: 3.38%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chestertown, MD

9816 FAIRLEE RD

CHESTERTOWN, MD

3 beds | 3 baths | N/A

$535,000

Airbnb cash on cash: 0.75%

Traditional cash on cash: 2.64%

Airbnb Rental Income: $1788

Traditional Rental Income: $2246

Airbnb ROI: 0.75%

Traditional ROI: 2.64%

2032 PONDTOWN RD

CHESTERTOWN, MD

3 beds | 2 baths | N/A

$325,000

Airbnb cash on cash: 2.35%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $1788

Traditional Rental Income: $2290

Airbnb ROI: 2.35%

Traditional ROI: 5.59%

136 HILLTOP DR

CHESTERTOWN, MD

3 beds | 2 baths | N/A

$366,000

Airbnb cash on cash: 1.83%

Traditional cash on cash: 5.07%

Airbnb Rental Income: $1788

Traditional Rental Income: $2414

Airbnb ROI: 1.83%

Traditional ROI: 5.07%

8706 ELM Road

CHESTERTOWN, MD

3 beds | 2 baths | 1,232 sq.ft.

$320,000

Airbnb cash on cash: 2.49%

Traditional cash on cash: 5.71%

Airbnb Rental Income: $1788

Traditional Rental Income: $2270

Airbnb ROI: 2.49%

Traditional ROI: 5.71%

215 FAIRVIEW DR

CHESTERTOWN, MD

3 beds | 3 baths | N/A

$425,000

Airbnb cash on cash: 1.58%

Traditional cash on cash: 5.32%

Airbnb Rental Income: $1788

Traditional Rental Income: $2790

Airbnb ROI: 1.58%

Traditional ROI: 5.32%

8629 AIRY HILL Road

CHESTERTOWN, MD

3 beds | 2 baths | 1,440 sq.ft.

$425,000

Airbnb cash on cash: 1.48%

Traditional cash on cash: 4.99%

Airbnb Rental Income: $1788

Traditional Rental Income: $2698

Airbnb ROI: 1.48%

Traditional ROI: 4.99%

240 MERGANSER Drive

CHESTERTOWN, MD

3 beds | 2 baths | 1,120 sq.ft.

$425,000

Airbnb cash on cash: 1.32%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $1788

Traditional Rental Income: $2120

Airbnb ROI: 1.32%

Traditional ROI: 3.38%

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