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: 5.47% Traditional cash on cash: 8.21% Airbnb Rental Income: $3371 Traditional Rental Income: $3607 Airbnb ROI: 5.47% 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.	$670,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 3.46% Airbnb Rental Income: $3489 Traditional Rental Income: $3409 Airbnb ROI: 2.36% Traditional ROI: 3.46%
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: 2.12% Traditional cash on cash: 5.69% Airbnb Rental Income: $1788 Traditional Rental Income: $2457 Airbnb ROI: 2.12% 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: 1.79% Traditional cash on cash: 4.5% Airbnb Rental Income: $1307 Traditional Rental Income: $1527 Airbnb ROI: 1.79% 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: 4.16% Traditional cash on cash: 5.22% Airbnb Rental Income: $3489 Traditional Rental Income: $3166 Airbnb ROI: 4.16% 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: 0.75% Traditional cash on cash: 2.64% Airbnb Rental Income: $1788 Traditional Rental Income: $2246 Airbnb ROI: 0.75% Traditional ROI: 2.64%
23416 CLOQUET Road CHESTERTOWN, MD Custom-Perfected Home with Luxury Finishes - Without the Luxury Price This beautifully rei...	3 beds \| 2 baths \| 1,512 sq.ft.	$384,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 4.48% Airbnb Rental Income: $1788 Traditional Rental Income: $2300 Airbnb ROI: 1.71% Traditional ROI: 4.48%
103 TRAFFORD Drive CHESTERTOWN, MD PRICE IMPROVEMENT: exceptional value? Priced BELOW 2025 Appraisal!! Instant equity! NOTE: ...	3 beds \| 3 baths \| 1,944 sq.ft.	$419,900	Airbnb cash on cash: 1% Traditional cash on cash: 3.53% Airbnb Rental Income: $1788 Traditional Rental Income: $2300 Airbnb ROI: 1% Traditional ROI: 3.53%
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: -2.16% Traditional cash on cash: 1.84% Airbnb Rental Income: $1307 Traditional Rental Income: $2769 Airbnb ROI: -2.16% Traditional ROI: 1.84%
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: 1.41% Traditional cash on cash: 2.68% Airbnb Rental Income: $1788 Traditional Rental Income: $1802 Airbnb ROI: 1.41% 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: 2.71% Traditional cash on cash: 4.68% Airbnb Rental Income: $1788 Traditional Rental Income: $1857 Airbnb ROI: 2.71% 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: 3.2% Traditional cash on cash: 3.51% Airbnb Rental Income: $3371 Traditional Rental Income: $2770 Airbnb ROI: 3.2% 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.	$1,295,500	Airbnb cash on cash: -0.45% Traditional cash on cash: 1.42% Airbnb Rental Income: $3371 Traditional Rental Income: $4880 Airbnb ROI: -0.45% Traditional ROI: 1.42%
304 HADAWAY Drive CHESTERTOWN, MD Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, o...	4 beds \| 2 baths \| 1,325 sq.ft.	$329,900	Airbnb cash on cash: 6.72% Traditional cash on cash: 5.31% Airbnb Rental Income: $3489 Traditional Rental Income: $2284 Airbnb ROI: 6.72% Traditional ROI: 5.31%
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: 5.52% Traditional cash on cash: 5.33% Airbnb Rental Income: $3489 Traditional Rental Income: $2650 Airbnb ROI: 5.52% 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.	$2,200,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 1.61% Airbnb Rental Income: $3371 Traditional Rental Income: $6617 Airbnb ROI: -0.35% Traditional ROI: 1.61%
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: 4.01% Traditional cash on cash: 5.29% Airbnb Rental Income: $3489 Traditional Rental Income: $3316 Airbnb ROI: 4.01% 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: 3.18% Traditional cash on cash: 5.52% Airbnb Rental Income: $3489 Traditional Rental Income: $3809 Airbnb ROI: 3.18% 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: -0.82% Traditional cash on cash: 1.08% Airbnb Rental Income: $1788 Traditional Rental Income: $2825 Airbnb ROI: -0.82% Traditional ROI: 1.08%
407 HIGH Street CHESTERTOWN, MD Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester ...	3 beds \| 5 baths \| 3,047 sq.ft.	$828,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 2.21% Airbnb Rental Income: $1788 Traditional Rental Income: $3564 Airbnb ROI: -0.73% Traditional ROI: 2.21%
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.	$499,999	Airbnb cash on cash: 3.21% Traditional cash on cash: 5.96% Airbnb Rental Income: $3371 Traditional Rental Income: $3905 Airbnb ROI: 3.21% Traditional ROI: 5.96%
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: 0.48% Traditional cash on cash: 3.75% Airbnb Rental Income: $1788 Traditional Rental Income: $3130 Airbnb ROI: 0.48% Traditional ROI: 3.75%
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: 0.47% Traditional cash on cash: 1.2% Airbnb Rental Income: $3489 Traditional Rental Income: $3735 Airbnb ROI: 0.47% 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: 1.61% Traditional cash on cash: 6.21% Airbnb Rental Income: $1788 Traditional Rental Income: $2769 Airbnb ROI: 1.61% 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: 3.73% Traditional cash on cash: 7.06% Airbnb Rental Income: $1788 Traditional Rental Income: $2011 Airbnb ROI: 3.73% 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: 0.78% Traditional cash on cash: 4.5% Airbnb Rental Income: $1788 Traditional Rental Income: $3125 Airbnb ROI: 0.78% 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: 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%
24581 WILLOW OAK Lane CHESTERTOWN, MD If you're looking for that secluded spot, with land, room to grow and stretch, and don't m...	3 beds \| 2 baths \| 1,352 sq.ft.	$229,990	Airbnb cash on cash: 3.93% Traditional cash on cash: 9.3% Airbnb Rental Income: $1788 Traditional Rental Income: $2469 Airbnb ROI: 3.93% Traditional ROI: 9.3%
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%
144 PROSPECT Street CHESTERTOWN, MD Great opportunity to own a small cottage in Chestertown. Right next to, and with direct ac...	2 beds \| 2 baths \| 1,082 sq.ft.	$179,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 10.27% Airbnb Rental Income: $1307 Traditional Rental Income: $2165 Airbnb ROI: 2.84% Traditional ROI: 10.27%
214 SILVER HEEL Road CHESTERTOWN, MD Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering th...	4 beds \| 3 baths \| 1,972 sq.ft.	$350,000	Airbnb cash on cash: 5.84% Traditional cash on cash: 6.69% Airbnb Rental Income: $3489 Traditional Rental Income: $2999 Airbnb ROI: 5.84% Traditional ROI: 6.69%
107 FLYING CLOUD Drive CHESTERTOWN, MD Welcome to this stunning 2023-built home with well-designed architectural elevations! The ...	5 beds \| 4 baths \| 2,534 sq.ft.	$395,000	Airbnb cash on cash: 4.47% Traditional cash on cash: 6.25% Airbnb Rental Income: $3371 Traditional Rental Income: $3280 Airbnb ROI: 4.47% Traditional ROI: 6.25%
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%
21363 LYNN Lane CHESTERTOWN, MD Take advantage of the Eastern Shore's amenities and quality of life in this low maintenanc...	3 beds \| 1 baths \| 1,314 sq.ft.	$205,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 9.57% Airbnb Rental Income: $1788 Traditional Rental Income: $2300 Airbnb ROI: 4.43% Traditional ROI: 9.57%
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%

Real Estate investment in Chestertown, MD

There are 38 properties for sale in the city of Chestertown . The median list price in Chestertown is $422,450 and the average price per square foot is $186. In May 2026, the average monthly cash on cash return in Chestertown is 3.00%. The average monthly rental income in Chestertown is $2,469.

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

There are 38 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 $2,469.

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: 5.47%

Traditional cash on cash: 8.21%

Airbnb Rental Income: $3371

Traditional Rental Income: $3607

Airbnb ROI: 5.47%

Traditional ROI: 8.21%

7844 CHESTER Court

CHESTERTOWN, MD

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

$670,000

Airbnb cash on cash: 2.36%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $3489

Traditional Rental Income: $3409

Airbnb ROI: 2.36%

Traditional ROI: 3.46%

109 WILTON Road

CHESTERTOWN, MD

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

$344,900

Airbnb cash on cash: 2.12%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $1788

Traditional Rental Income: $2457

Airbnb ROI: 2.12%

Traditional ROI: 5.69%

21217 TEXAS Avenue

CHESTERTOWN, MD

2 beds | 1 baths | 912 sq.ft.

$244,500

Airbnb cash on cash: 1.79%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $1307

Traditional Rental Income: $1527

Airbnb ROI: 1.79%

Traditional ROI: 4.5%

110 TRAFFORD Drive

CHESTERTOWN, MD

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

$450,000

Airbnb cash on cash: 4.16%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $3489

Traditional Rental Income: $3166

Airbnb ROI: 4.16%

Traditional ROI: 5.22%

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%

23416 CLOQUET Road

CHESTERTOWN, MD

3 beds | 2 baths | 1,512 sq.ft.

$384,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: 4.48%

Airbnb Rental Income: $1788

Traditional Rental Income: $2300

Airbnb ROI: 1.71%

Traditional ROI: 4.48%

103 TRAFFORD Drive

CHESTERTOWN, MD

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

$419,900

Airbnb cash on cash: 1%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $1788

Traditional Rental Income: $2300

Airbnb ROI: 1%