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.

Investment Property for Sale in Chestertown, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
6746 QUAKER NECK Road CHESTERTOWN, MD	5 beds \| 3 baths \| 3,371 sq.ft.	$384,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.21% Airbnb Rental Income: $null Traditional Rental Income: $3607 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $3409 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 5.69% Airbnb Rental Income: $null Traditional Rental Income: $2457 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 5.03% Airbnb Rental Income: $null Traditional Rental Income: $3166 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 1.73% Airbnb Rental Income: $null Traditional Rental Income: $2769 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 2.68% Airbnb Rental Income: $null Traditional Rental Income: $1802 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $2770 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 1.25% Airbnb Rental Income: $null Traditional Rental Income: $4880 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 4.77% Airbnb Rental Income: $null Traditional Rental Income: $2896 Airbnb ROI: N/A Traditional ROI: 4.77%
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: N/A Traditional cash on cash: 5.15% Airbnb Rental Income: $null Traditional Rental Income: $2284 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 11.51% Airbnb Rental Income: $null Traditional Rental Income: $1811 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 1.39% Airbnb Rental Income: $null Traditional Rental Income: $6617 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 5.29% Airbnb Rental Income: $null Traditional Rental Income: $3316 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 5.2% Airbnb Rental Income: $null Traditional Rental Income: $3809 Airbnb ROI: N/A Traditional ROI: 5.2%
106 QUEEN Street S CHESTERTOWN, MD Open House Friday April 3rd 5-7pm and Saturday April 4th 10am-12pm The Bedingfield Hands...	3 beds \| 4 baths \| 2,472 sq.ft.	$865,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.08% Airbnb Rental Income: $null Traditional Rental Income: $2825 Airbnb ROI: N/A Traditional ROI: 1.08%
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: N/A Traditional cash on cash: 7.32% Airbnb Rental Income: $null Traditional Rental Income: $2225 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 5.63% Airbnb Rental Income: $null Traditional Rental Income: $3905 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $3130 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $2027 Airbnb ROI: N/A 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.	$136,800	Airbnb cash on cash: N/A Traditional cash on cash: 10.77% Airbnb Rental Income: $null Traditional Rental Income: $1778 Airbnb ROI: N/A Traditional ROI: 10.77%
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: N/A Traditional cash on cash: 6.88% Airbnb Rental Income: $null Traditional Rental Income: $2081 Airbnb ROI: N/A Traditional ROI: 6.88%
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: N/A Traditional cash on cash: 3.88% Airbnb Rental Income: $null Traditional Rental Income: $1801 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 1.2% Airbnb Rental Income: $null Traditional Rental Income: $3735 Airbnb ROI: N/A Traditional ROI: 1.2%
107 CONLEY Drive CHESTERTOWN, MD Purchase of opportunity thru rehab financing for completion of a new kitchen, painting and...	3 beds \| 1 baths \| 1,140 sq.ft.	$170,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.6% Airbnb Rental Income: $null Traditional Rental Income: $1523 Airbnb ROI: N/A Traditional ROI: 6.6%
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: N/A Traditional cash on cash: 5.31% Airbnb Rental Income: $null Traditional Rental Income: $2769 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 7.06% Airbnb Rental Income: $null Traditional Rental Income: $2011 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 4.5% Airbnb Rental Income: $null Traditional Rental Income: $3125 Airbnb ROI: N/A Traditional ROI: 4.5%
104 FLYING CLOUD Drive CHESTERTOWN, MD Welcome to The Verona, a spacious three-story, move-in ready home offering over 2,500 squa...	5 beds \| 4 baths \| 2,535 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.3% Airbnb Rental Income: $null Traditional Rental Income: $3331 Airbnb ROI: N/A Traditional ROI: 6.3%

Real Estate investment in Chestertown, MD

There are 38 properties for sale in the city of Chestertown . The median list price in Chestertown is $450,000 and the average price per square foot is $193. In April 2026, the average monthly cash on cash return in Chestertown is 4.00%. The average monthly rental income in Chestertown is $2,638.

Chestertown, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 38 investment properties available for sale in Chestertown.

The ROI for Short-Term is higher than the Long-Term in Chestertown with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Chestertown, MD

6746 QUAKER NECK Road

CHESTERTOWN, MD

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

$384,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.21%

Airbnb Rental Income: $null

Traditional Rental Income: $3607

Airbnb ROI: N/A

Traditional ROI: 8.21%

7844 CHESTER Court

CHESTERTOWN, MD

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

$695,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.3%

Airbnb Rental Income: $null

Traditional Rental Income: $3409

Airbnb ROI: N/A

Traditional ROI: 3.3%

109 WILTON Road

CHESTERTOWN, MD

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

$344,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.69%

Airbnb Rental Income: $null

Traditional Rental Income: $2457

Airbnb ROI: N/A

Traditional ROI: 5.69%

110 TRAFFORD Drive

CHESTERTOWN, MD

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

$465,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.03%

Airbnb Rental Income: $null

Traditional Rental Income: $3166

Airbnb ROI: N/A

Traditional ROI: 5.03%

103 LANDING Lane

CHESTERTOWN, MD

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

$519,999

Airbnb cash on cash: N/A

Traditional cash on cash: 1.73%

Airbnb Rental Income: $null

Traditional Rental Income: $2769

Airbnb ROI: N/A

Traditional ROI: 1.73%

109 S COLLEGE Avenue

CHESTERTOWN, MD

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

$419,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.68%

Airbnb Rental Income: $null

Traditional Rental Income: $1802

Airbnb ROI: N/A

Traditional ROI: 2.68%

116 HARLAN Loop

CHESTERTOWN, MD

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

$509,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.51%

Airbnb Rental Income: $null

Traditional Rental Income: $2770

Airbnb ROI: N/A

Traditional ROI: 3.51%

105 HIGH Street

CHESTERTOWN, MD

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

$1,395,500

Airbnb cash on cash: N/A

Traditional cash on cash: 1.25%

Airbnb Rental Income: $null

Traditional Rental Income: $4880

Airbnb ROI: N/A