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.

Tment Property for Sale in Chestertown, MD

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

Showing 35 Tment Property 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
6746 QUAKER NECK Road CHESTERTOWN, MD	5 beds \| 3 baths \| 3,371 sq.ft.	$445,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 6.96% Airbnb Rental Income: $3223 Traditional Rental Income: $3607 Airbnb ROI: 4.3% Traditional ROI: 6.96%
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: 0.25% Traditional cash on cash: 3.3% Airbnb Rental Income: $1948 Traditional Rental Income: $3409 Airbnb ROI: 0.25% 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: 4.96% Traditional cash on cash: 5.69% Airbnb Rental Income: $2892 Traditional Rental Income: $2457 Airbnb ROI: 4.96% Traditional ROI: 5.69%
110 TRAFFORD Drive CHESTERTOWN, MD Here's the opportunity buyers wait for. A classic Colonial in sought-after Coventry Farms,...	4 beds \| 3 baths \| 2,880 sq.ft.	$465,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 5.03% Airbnb Rental Income: $1948 Traditional Rental Income: $3166 Airbnb ROI: 1.05% Traditional ROI: 5.03%
103 LANDING Lane CHESTERTOWN, MD Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable...	2 beds \| 3 baths \| 2,100 sq.ft.	$519,999	Airbnb cash on cash: -0.93% Traditional cash on cash: 1.73% Airbnb Rental Income: $1999 Traditional Rental Income: $2769 Airbnb ROI: -0.93% Traditional ROI: 1.73%
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: 3.74% Traditional cash on cash: 2.68% Airbnb Rental Income: $2892 Traditional Rental Income: $1802 Airbnb ROI: 3.74% Traditional ROI: 2.68%
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: 2.94% Traditional cash on cash: 3.51% Airbnb Rental Income: $3223 Traditional Rental Income: $2770 Airbnb ROI: 2.94% 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: -0.59% Traditional cash on cash: 1.25% Airbnb Rental Income: $3223 Traditional Rental Income: $4880 Airbnb ROI: -0.59% Traditional ROI: 1.25%
201 BIRCH RUN Road CHESTERTOWN, MD ***PRICED $30,000 UNDER THE RECENT APPRAISED VALUE*** One floor living, a wood burning...	3 beds \| 2 baths \| 1,588 sq.ft.	$435,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 4.77% Airbnb Rental Income: $2892 Traditional Rental Income: $2896 Airbnb ROI: 3.11% Traditional ROI: 4.77%
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: 8.84% Traditional cash on cash: 11.51% Airbnb Rental Income: $1999 Traditional Rental Income: $1811 Airbnb ROI: 8.84% Traditional ROI: 11.51%
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.	$2,400,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 1.39% Airbnb Rental Income: $3223 Traditional Rental Income: $6617 Airbnb ROI: -0.46% Traditional ROI: 1.39%
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: 1.26% Traditional cash on cash: 5.29% Airbnb Rental Income: $1948 Traditional Rental Income: $3316 Airbnb ROI: 1.26% Traditional ROI: 5.29%
311 DEVON Drive CHESTERTOWN, MD REDUCED! 311 Devon Drive is located in Coventry Farms; and being located within the Cheste...	5 beds \| 4 baths \| 3,504 sq.ft.	$525,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 5.2% Airbnb Rental Income: $3223 Traditional Rental Income: $3809 Airbnb ROI: 2.52% Traditional ROI: 5.2%
109 METCALF Road CHESTERTOWN, MD Brand new home in Historic Chestertown available for move-in Right Now. This home features...	3 beds \| 2 baths \| 1,280 sq.ft.	$264,900	Airbnb cash on cash: 7.3% Traditional cash on cash: 7.32% Airbnb Rental Income: $2892 Traditional Rental Income: $2225 Airbnb ROI: 7.3% Traditional ROI: 7.32%
218 CAMELOT Drive CHESTERTOWN, MD Picture Perfect Colonial in Coventry Farms - Chestertown, Maryland Welcome to 218 Camelot ...	5 beds \| 4 baths \| 3,932 sq.ft.	$525,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 5.63% Airbnb Rental Income: $3223 Traditional Rental Income: $3905 Airbnb ROI: 2.76% Traditional ROI: 5.63%
204 DOUBLE CREEK Road CHESTERTOWN, MD Custom builder selling his own home that has been well built, well maintained, and thought...	3 beds \| 3 baths \| 2,927 sq.ft.	$612,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 3.64% Airbnb Rental Income: $2892 Traditional Rental Income: $3130 Airbnb ROI: 2.05% Traditional ROI: 3.64%
301 LINCOLN Drive CHESTERTOWN, MD Discover this beautifully renovated ranch-style home (2023), offering 1,152 square feet of...	3 beds \| 2 baths \| 1,152 sq.ft.	$309,900	Airbnb cash on cash: 5.09% Traditional cash on cash: 4.42% Airbnb Rental Income: $2892 Traditional Rental Income: $2027 Airbnb ROI: 5.09% Traditional ROI: 4.42%
21324 PERSIMMON Drive CHESTERTOWN, MD 2 level townhome in sought after Tolchester Village! Features a terrific open kitchen with...	2 beds \| 1 baths \| 1,232 sq.ft.	$152,000	Airbnb cash on cash: 7.56% Traditional cash on cash: 9.63% Airbnb Rental Income: $1999 Traditional Rental Income: $1778 Airbnb ROI: 7.56% Traditional ROI: 9.63%
107 METCALF Road CHESTERTOWN, MD Brand new home in Historic Chestertown available for move-in this Right Now. This home fea...	3 beds \| 2 baths \| 1,200 sq.ft.	$259,900	Airbnb cash on cash: 7.45% Traditional cash on cash: 6.88% Airbnb Rental Income: $2892 Traditional Rental Income: $2081 Airbnb ROI: 7.45% Traditional ROI: 6.88%
112 ELM Street CHESTERTOWN, MD Sought after location in College Heights. Short walk to downtown Chestertown and Parks. Th...	3 beds \| 1 baths \| 1,356 sq.ft.	$269,900	Airbnb cash on cash: 6.39% Traditional cash on cash: 5.14% Airbnb Rental Income: $2892 Traditional Rental Income: $1903 Airbnb ROI: 6.39% Traditional ROI: 5.14%
21125 IOWA Avenue CHESTERTOWN, MD Welcome to "The Cottage," as it's affectionately known! This charming home offers beautifu...	2 beds \| 1 baths \| 1,294 sq.ft.	$339,900	Airbnb cash on cash: 2.86% Traditional cash on cash: 3.88% Airbnb Rental Income: $1999 Traditional Rental Income: $1801 Airbnb ROI: 2.86% Traditional ROI: 3.88%
8276 BROAD NECK Road CHESTERTOWN, MD Wait until you see this! Impecably maintained brick house on nearly 20 acres, overlooking ...	4 beds \| 4 baths \| 3,383 sq.ft.	$1,495,000	Airbnb cash on cash: -0.46% Traditional cash on cash: -0.01% Airbnb Rental Income: $1948 Traditional Rental Income: $2047 Airbnb ROI: -0.46% Traditional ROI: -0.01%
202 WALDO Drive CHESTERTOWN, MD A Place Full of Possibility in Byford Development Tucked in the heart of the Byford commun...	3 beds \| 2 baths \| 2,055 sq.ft.	$389,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 5.31% Airbnb Rental Income: $2892 Traditional Rental Income: $2769 Airbnb ROI: 3.81% Traditional ROI: 5.31%
139 PROSPECT Street CHESTERTOWN, MD Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher...	3 beds \| 1 baths \| 1,200 sq.ft.	$225,000	Airbnb cash on cash: 8.05% Traditional cash on cash: 7.06% Airbnb Rental Income: $2892 Traditional Rental Income: $2011 Airbnb ROI: 8.05% Traditional ROI: 7.06%
101 COLEMAN Drive CHESTERTOWN, MD Tucked away just south of the scenic Chester River and moments from the timeless charm of ...	3 beds \| 3 baths \| 2,268 sq.ft.	$524,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 4.5% Airbnb Rental Income: $2892 Traditional Rental Income: $3125 Airbnb ROI: 2.65% Traditional ROI: 4.5%

Your search for investment property begins and ends here

Tment Property for Sale in Chestertown, MD

6746 QUAKER NECK Road

CHESTERTOWN, MD

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

$445,000

Airbnb cash on cash: 4.3%

Traditional cash on cash: 6.96%

Airbnb Rental Income: $3223

Traditional Rental Income: $3607

Airbnb ROI: 4.3%

Traditional ROI: 6.96%

7844 CHESTER Court

CHESTERTOWN, MD

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

$695,000

Airbnb cash on cash: 0.25%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $1948

Traditional Rental Income: $3409

Airbnb ROI: 0.25%

Traditional ROI: 3.3%

109 WILTON Road

CHESTERTOWN, MD

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

$344,900

Airbnb cash on cash: 4.96%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $2892

Traditional Rental Income: $2457

Airbnb ROI: 4.96%

Traditional ROI: 5.69%

110 TRAFFORD Drive

CHESTERTOWN, MD

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

$465,000

Airbnb cash on cash: 1.05%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $1948

Traditional Rental Income: $3166

Airbnb ROI: 1.05%

Traditional ROI: 5.03%

103 LANDING Lane

CHESTERTOWN, MD

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

$519,999

Airbnb cash on cash: -0.93%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $1999

Traditional Rental Income: $2769

Airbnb ROI: -0.93%

Traditional ROI: 1.73%

109 S COLLEGE Avenue

CHESTERTOWN, MD

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

$419,900

Airbnb cash on cash: 3.74%

Traditional cash on cash: 2.68%

Airbnb Rental Income: $2892

Traditional Rental Income: $1802

Airbnb ROI: 3.74%

Traditional ROI: 2.68%

116 HARLAN Loop

CHESTERTOWN, MD

5 beds | 4 baths | 4,067 sq.ft.

$509,000

Airbnb cash on cash: 2.94%

Traditional cash on cash: 3.51%

Airbnb Rental Income: $3223

Traditional Rental Income: $2770

Airbnb ROI: 2.94%

Traditional ROI: 3.51%

105 HIGH Street

CHESTERTOWN, MD

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

$1,395,500

Airbnb cash on cash: -0.59%

Traditional cash on cash: 1.25%

Airbnb Rental Income: $3223

Traditional Rental Income: $4880

Airbnb ROI: -0.59%