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
126 CHAR NOR MANOR Boulevard CHESTERTOWN, MD This charming 3 bedroom, 2 bathroom home offers the perfect blend of comfort, convenience,...	3 beds \| 2 baths \| 1,304 sq.ft.	$349,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 4.75% Airbnb Rental Income: $2059 Traditional Rental Income: $2185 Airbnb ROI: 2.74% Traditional ROI: 4.75%
6746 QUAKER NECK Road CHESTERTOWN, MD	5 beds \| 3 baths \| 3,371 sq.ft.	$384,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 8.21% Airbnb Rental Income: $2925 Traditional Rental Income: $3607 Airbnb ROI: 4.44% 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: 0.36% Traditional cash on cash: 3.3% Airbnb Rental Income: $2028 Traditional Rental Income: $3409 Airbnb ROI: 0.36% 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: 2.82% Traditional cash on cash: 5.69% Airbnb Rental Income: $2059 Traditional Rental Income: $2457 Airbnb ROI: 2.82% 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.	$265,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 4.09% Airbnb Rental Income: $1721 Traditional Rental Income: $1527 Airbnb ROI: 2.96% Traditional ROI: 4.09%
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: 1.27% Traditional cash on cash: 5.22% Airbnb Rental Income: $2028 Traditional Rental Income: $3166 Airbnb ROI: 1.27% Traditional ROI: 5.22%
103 TRAFFORD Drive CHESTERTOWN, MD Welcome to 103 Trafford Drive; an exceptionally maintained 3 bedroom home just minutes fro...	3 beds \| 3 baths \| 1,944 sq.ft.	$450,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 3.23% Airbnb Rental Income: $2059 Traditional Rental Income: $2300 Airbnb ROI: 1.4% Traditional ROI: 3.23%
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.	$519,999	Airbnb cash on cash: -1.4% Traditional cash on cash: 1.73% Airbnb Rental Income: $1721 Traditional Rental Income: $2769 Airbnb ROI: -1.4% 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: 1.98% Traditional cash on cash: 2.68% Airbnb Rental Income: $2059 Traditional Rental Income: $1802 Airbnb ROI: 1.98% Traditional ROI: 2.68%
208 CENTRAL Drive CHESTERTOWN, MD Welcome to 208 Central Drive, located in the desirable Chester Harbor community just minut...	3 beds \| 1 baths \| 1,120 sq.ft.	$299,000	Airbnb cash on cash: 3.51% Traditional cash on cash: 4.68% Airbnb Rental Income: $2059 Traditional Rental Income: $1857 Airbnb ROI: 3.51% Traditional ROI: 4.68%
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: 2.42% Traditional cash on cash: 3.51% Airbnb Rental Income: $2925 Traditional Rental Income: $2770 Airbnb ROI: 2.42% 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: -0.78% Traditional cash on cash: 1.25% Airbnb Rental Income: $2925 Traditional Rental Income: $4880 Airbnb ROI: -0.78% Traditional ROI: 1.25%
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: 2.69% Traditional cash on cash: 5.15% Airbnb Rental Income: $2028 Traditional Rental Income: $2284 Airbnb ROI: 2.69% 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: 6.99% Traditional cash on cash: 11.51% Airbnb Rental Income: $1721 Traditional Rental Income: $1811 Airbnb ROI: 6.99% Traditional ROI: 11.51%
23043 BAY SHORE Spur CHESTERTOWN, MD Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 ac...	4 beds \| 3 baths \| 2,630 sq.ft.	$385,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 5.33% Airbnb Rental Income: $2028 Traditional Rental Income: $2650 Airbnb ROI: 2.15% Traditional ROI: 5.33%
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: -0.57% Traditional cash on cash: 1.39% Airbnb Rental Income: $2925 Traditional Rental Income: $6617 Airbnb ROI: -0.57% 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 \| N/A baths \| 2,524 sq.ft.	$499,900	Airbnb cash on cash: 1.4% Traditional cash on cash: 5.29% Airbnb Rental Income: $2028 Traditional Rental Income: $3316 Airbnb ROI: 1.4% Traditional ROI: 5.29%
311 DEVON Drive CHESTERTOWN, MD 311 Devon Drive is located in Coventry Farms; and being located within the Chestertown tow...	4 beds \| 3 baths \| 3,504 sq.ft.	$499,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 5.52% Airbnb Rental Income: $2028 Traditional Rental Income: $3809 Airbnb ROI: 0.57% Traditional ROI: 5.52%
106 QUEEN Street S CHESTERTOWN, MD New photos just added-capturing the truly one-of-a-kind gardens now in full bloom! This is...	3 beds \| 4 baths \| 2,472 sq.ft.	$865,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 1.08% Airbnb Rental Income: $2059 Traditional Rental Income: $2825 Airbnb ROI: -0.54% Traditional ROI: 1.08%
218 CAMELOT Drive CHESTERTOWN, MD Seller is motivated and can move quickly in 30 days! Welcome to 218 Camelot Drive, stunnin...	5 beds \| 4 baths \| 3,932 sq.ft.	$510,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 5.82% Airbnb Rental Income: $2925 Traditional Rental Income: $3905 Airbnb ROI: 2.35% Traditional ROI: 5.82%
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.	$598,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 3.75% Airbnb Rental Income: $2059 Traditional Rental Income: $3130 Airbnb ROI: 0.88% Traditional ROI: 3.75%
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.	$299,900	Airbnb cash on cash: 2.83% Traditional cash on cash: 4.6% Airbnb Rental Income: $2059 Traditional Rental Income: $2027 Airbnb ROI: 2.83% Traditional ROI: 4.6%
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: 6.71% Traditional cash on cash: 10.77% Airbnb Rental Income: $1721 Traditional Rental Income: $1778 Airbnb ROI: 6.71% Traditional ROI: 10.77%
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: 2.14% Traditional cash on cash: 3.88% Airbnb Rental Income: $1721 Traditional Rental Income: $1801 Airbnb ROI: 2.14% 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: -0.41% Traditional cash on cash: 1.2% Airbnb Rental Income: $2028 Traditional Rental Income: $3735 Airbnb ROI: -0.41% Traditional ROI: 1.2%
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.	$340,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 6.21% Airbnb Rental Income: $2059 Traditional Rental Income: $2769 Airbnb ROI: 2.32% Traditional ROI: 6.21%
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: 4.79% Traditional cash on cash: 7.06% Airbnb Rental Income: $2059 Traditional Rental Income: $2011 Airbnb ROI: 4.79% 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: 1.24% Traditional cash on cash: 4.5% Airbnb Rental Income: $2059 Traditional Rental Income: $3125 Airbnb ROI: 1.24% Traditional ROI: 4.5%
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: 3.09% Traditional cash on cash: 5.59% Airbnb Rental Income: $2059 Traditional Rental Income: $2290 Airbnb ROI: 3.09% Traditional ROI: 5.59%
113 PEAR TREE POINT Road CHESTERTOWN, MD OPPORTUNITY KNOCKS!! This home is being sold as-is and is ready for someone with vision an...	3 beds \| 1 baths \| 1,296 sq.ft.	$250,000	Airbnb cash on cash: 4.27% Traditional cash on cash: 6.25% Airbnb Rental Income: $2059 Traditional Rental Income: $1994 Airbnb ROI: 4.27% Traditional ROI: 6.25%
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: 2.49% Traditional cash on cash: 5.07% Airbnb Rental Income: $2059 Traditional Rental Income: $2414 Airbnb ROI: 2.49% Traditional ROI: 5.07%
108 OAK LEAF Drive CHESTERTOWN, MD This beautifully maintained end-unit townhome, owned by its original owner, has been metic...	2 beds \| 3 baths \| 1,867 sq.ft.	$299,500	Airbnb cash on cash: 2% Traditional cash on cash: 6.9% Airbnb Rental Income: $1721 Traditional Rental Income: $2628 Airbnb ROI: 2% Traditional ROI: 6.9%
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: 3.24% Traditional cash on cash: 5.71% Airbnb Rental Income: $2059 Traditional Rental Income: $2270 Airbnb ROI: 3.24% Traditional ROI: 5.71%
115 ACORN Drive CHESTERTOWN, MD Welcome to 115 Acorn Drive in the desirable Oak Hollow community of Chestertown, Maryland-...	2 beds \| 3 baths \| 1,864 sq.ft.	$296,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 6.56% Airbnb Rental Income: $1721 Traditional Rental Income: $2507 Airbnb ROI: 2.03% Traditional ROI: 6.56%
301 HILLTOP Lane CHESTERTOWN, MD Move-in ready and priced to sell, this 3-bedroom, 2.5-bath end-unit townhouse offers the p...	3 beds \| 3 baths \| 1,197 sq.ft.	$225,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 7.37% Airbnb Rental Income: $2059 Traditional Rental Income: $2121 Airbnb ROI: 4.58% Traditional ROI: 7.37%

Real Estate investment in Chestertown, MD

There are 35 properties for sale in the city of Chestertown . The median list price in Chestertown is $366,000 and the average price per square foot is $168. In May 2026, the average monthly cash on cash return in Chestertown is 3.00%. The average monthly rental income in Chestertown is $2,391.

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

There are 35 investment properties available for sale in Chestertown.

In 2026, the best neighborhood to buy investment property is CHESTERTOWN.

The ROI for Long-Term is higher than the Short-Term in Chestertown with average rental income of $2,391.

Your search for investment property begins and ends here

Investment Property for Sale in Chestertown, MD

126 CHAR NOR MANOR Boulevard

CHESTERTOWN, MD

3 beds | 2 baths | 1,304 sq.ft.

$349,000

Airbnb cash on cash: 2.74%

Traditional cash on cash: 4.75%

Airbnb Rental Income: $2059

Traditional Rental Income: $2185

Airbnb ROI: 2.74%

Traditional ROI: 4.75%

6746 QUAKER NECK Road

CHESTERTOWN, MD

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

$384,000

Airbnb cash on cash: 4.44%

Traditional cash on cash: 8.21%

Airbnb Rental Income: $2925

Traditional Rental Income: $3607

Airbnb ROI: 4.44%

Traditional ROI: 8.21%

7844 CHESTER Court

CHESTERTOWN, MD

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

$695,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $2028

Traditional Rental Income: $3409

Airbnb ROI: 0.36%

Traditional ROI: 3.3%

109 WILTON Road

CHESTERTOWN, MD

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

$344,900

Airbnb cash on cash: 2.82%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $2059

Traditional Rental Income: $2457

Airbnb ROI: 2.82%

Traditional ROI: 5.69%

21217 TEXAS Avenue

CHESTERTOWN, MD

2 beds | 1 baths | 912 sq.ft.

$265,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $1721

Traditional Rental Income: $1527

Airbnb ROI: 2.96%

Traditional ROI: 4.09%

110 TRAFFORD Drive

CHESTERTOWN, MD

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

$450,000

Airbnb cash on cash: 1.27%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $2028

Traditional Rental Income: $3166

Airbnb ROI: 1.27%

Traditional ROI: 5.22%

103 TRAFFORD Drive

CHESTERTOWN, MD

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

$450,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $2059

Traditional Rental Income: $2300

Airbnb ROI: 1.4%

Traditional ROI: 3.23%

103 LANDING Lane

CHESTERTOWN, MD

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

$519,999

Airbnb cash on cash: -1.4%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $1721

Traditional Rental Income: $2769

Airbnb ROI: -1.4%