Airbnb Properties for Sale in Chestertown, MD

Looking for a vacation rental investment in Chestertown, MD with high ROI ?

Explore a range of newly added short-term rental homes in Chestertown, MD. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Chestertown, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
25800 COLLINS AVENUE CHESTERTOWN, MD Located in Country Club Estates, on a lovely, corner lot with mature trees. Solid brick ra...	3 beds \| 2 baths \| 2,162 sq.ft.	$485,000	Airbnb cash on cash: 6.57% Traditional cash on cash: 3.95% Airbnb Rental Income: $4884 Traditional Rental Income: $2693 Airbnb ROI: 6.57% Traditional ROI: 3.95%
200 FEY RD CHESTERTOWN, MD Welcome to this charming rancher situated just minutes from historic downtown Chestertown....	3 beds \| 2 baths \| N/A	$374,900	Airbnb cash on cash: 9.17% Traditional cash on cash: 5.11% Airbnb Rental Income: $4884 Traditional Rental Income: $2450 Airbnb ROI: 9.17% Traditional ROI: 5.11%
109 WILTON ROAD CHESTERTOWN, MD Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comf...	3 beds \| 2 baths \| 1,392 sq.ft.	$349,900	Airbnb cash on cash: 9.97% Traditional cash on cash: 5.64% Airbnb Rental Income: $4884 Traditional Rental Income: $2457 Airbnb ROI: 9.97% Traditional ROI: 5.64%
251 DEVON DRIVE CHESTERTOWN, MD Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When ente...	3 beds \| 3 baths \| 3,935 sq.ft.	$595,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 2.77% Airbnb Rental Income: $4884 Traditional Rental Income: $2834 Airbnb ROI: 4.66% Traditional ROI: 2.77%
116 HARLAN LOOP CHESTERTOWN, MD Welcome to Coventry Farms in Chestertown where comfort, elegance, and space come together ...	5 beds \| 4 baths \| 4,067 sq.ft.	$529,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 3.34% Airbnb Rental Income: $5900 Traditional Rental Income: $2770 Airbnb ROI: 7.3% Traditional ROI: 3.34%
5179 QUAKER NECK ROAD CHESTERTOWN, MD $20,000 Price Reduction! A One-of-a-Kind Historic Treasure Reimagined for Modern Living St...	1 beds \| 1 baths \| 1,148 sq.ft.	$559,900	Airbnb cash on cash: 1.65% Traditional cash on cash: 1.3% Airbnb Rental Income: $2337 Traditional Rental Income: $1571 Airbnb ROI: 1.65% Traditional ROI: 1.3%
201 BIRCH RUN ROAD CHESTERTOWN, MD This Mid Century Modern is located in Mile Tree Village, one of Chestertown's most coveted...	3 beds \| 2 baths \| 1,588 sq.ft.	$470,000	Airbnb cash on cash: 6.58% Traditional cash on cash: 4.34% Airbnb Rental Income: $4884 Traditional Rental Income: $2896 Airbnb ROI: 6.58% Traditional ROI: 4.34%
201 BOUNDARY AVENUE CHESTERTOWN, MD Discover this spacious home offering 3,100 sq ft of living space on a acre lot with deeded...	3 beds \| 3 baths \| 3,096 sq.ft.	$449,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 6.53% Airbnb Rental Income: $4884 Traditional Rental Income: $3560 Airbnb ROI: 7.3% Traditional ROI: 6.53%
907 N MEADOWVIEW DRIVE CHESTERTOWN, MD Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crest...	3 beds \| 3 baths \| 1,842 sq.ft.	$440,000	Airbnb cash on cash: 7.53% Traditional cash on cash: 4.71% Airbnb Rental Income: $4884 Traditional Rental Income: $2720 Airbnb ROI: 7.53% Traditional ROI: 4.71%
7729 COUNTRY CLUB LANE CHESTERTOWN, MD Country Club Estates - Live Where You Play Just 1.5 Miles from Downtown Chestertown! Enjoy...	3 beds \| 3 baths \| 2,280 sq.ft.	$635,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 3.36% Airbnb Rental Income: $4884 Traditional Rental Income: $3094 Airbnb ROI: 4.69% Traditional ROI: 3.36%
26933 MALLARD ROAD CHESTERTOWN, MD Stunning waterfront property with private dock site on the Chester River. The house has be...	3 beds \| 3 baths \| 1,600 sq.ft.	$625,000	Airbnb cash on cash: 4.74% Traditional cash on cash: 3.33% Airbnb Rental Income: $4884 Traditional Rental Income: $3063 Airbnb ROI: 4.74% Traditional ROI: 3.33%
10751 MILLBROOK DR CHESTERTOWN, MD Chesapeake Landing - This home is featured on a corner lot with large living space and add...	3 beds \| 2 baths \| N/A	$375,000	Airbnb cash on cash: 8.92% Traditional cash on cash: 4.69% Airbnb Rental Income: $4884 Traditional Rental Income: $2392 Airbnb ROI: 8.92% Traditional ROI: 4.69%
225 DUKE OF KENT STREET CHESTERTOWN, MD Spacious One-Level Living Near Downtown Chestertown & The Chester River! Welcome to this ...	3 beds \| 3 baths \| 1,850 sq.ft.	$399,900	Airbnb cash on cash: 8.42% Traditional cash on cash: 6.18% Airbnb Rental Income: $4884 Traditional Rental Income: $3041 Airbnb ROI: 8.42% Traditional ROI: 6.18%
23110 OLD FAIRLEE ROAD CHESTERTOWN, MD Renovated Ranch Home in Fairlee. This home has been updated top to bottom. Recent updates ...	3 beds \| 1 baths \| 1,805 sq.ft.	$379,900	Airbnb cash on cash: 9.13% Traditional cash on cash: 3.26% Airbnb Rental Income: $4884 Traditional Rental Income: $1791 Airbnb ROI: 9.13% Traditional ROI: 3.26%

Vacation Rentals in Chestertown

There are 14 vacation rental properties available for sale in the city of Chestertown . The median list price of Airbnb properties available for sale in Chestertown is $472,500 and the average price per square foot is $186. The cash on cash return on vacation rentals in Chestertown is 7.00%. The average monthly short term rental income in Chestertown is $4,884.

Chestertown, MD Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 14 Airbnb properties available for sale in Chestertown.

In 2025, the best neighborhood to buy short term rental property is CHESTERTOWN.

In September 2025, the average Airbnb occupancy rate in Chestertown is 39%.

Airbnb data on vacation rentals in Chestertown, MD is available at Mashvisor. You can access data such as listings, real-time pricing trends, Chestertown, MD market insights, guest information and booking details, seasonality trends and historical Chestertown, MD Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Chestertown, MD

25800 COLLINS AVENUE

CHESTERTOWN, MD

3 beds | 2 baths | 2,162 sq.ft.

$485,000

Airbnb cash on cash: 6.57%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $4884

Traditional Rental Income: $2693

Airbnb ROI: 6.57%

Traditional ROI: 3.95%

200 FEY RD

CHESTERTOWN, MD

3 beds | 2 baths | N/A

$374,900

Airbnb cash on cash: 9.17%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $4884

Traditional Rental Income: $2450

Airbnb ROI: 9.17%

Traditional ROI: 5.11%

109 WILTON ROAD

CHESTERTOWN, MD

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

$349,900

Airbnb cash on cash: 9.97%

Traditional cash on cash: 5.64%

Airbnb Rental Income: $4884

Traditional Rental Income: $2457

Airbnb ROI: 9.97%

Traditional ROI: 5.64%

251 DEVON DRIVE

CHESTERTOWN, MD

3 beds | 3 baths | 3,935 sq.ft.

$595,000

Airbnb cash on cash: 4.66%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $4884

Traditional Rental Income: $2834

Airbnb ROI: 4.66%

Traditional ROI: 2.77%

116 HARLAN LOOP

CHESTERTOWN, MD

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

$529,000

Airbnb cash on cash: 7.3%

Traditional cash on cash: 3.34%

Airbnb Rental Income: $5900

Traditional Rental Income: $2770

Airbnb ROI: 7.3%

Traditional ROI: 3.34%

5179 QUAKER NECK ROAD

CHESTERTOWN, MD

1 beds | 1 baths | 1,148 sq.ft.

$559,900

Airbnb cash on cash: 1.65%

Traditional cash on cash: 1.3%

Airbnb Rental Income: $2337

Traditional Rental Income: $1571

Airbnb ROI: 1.65%

Traditional ROI: 1.3%

201 BIRCH RUN ROAD

CHESTERTOWN, MD

3 beds | 2 baths | 1,588 sq.ft.

$470,000

Airbnb cash on cash: 6.58%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $4884

Traditional Rental Income: $2896

Airbnb ROI: 6.58%

Traditional ROI: 4.34%

201 BOUNDARY AVENUE

CHESTERTOWN, MD

3 beds | 3 baths | 3,096 sq.ft.

$449,000

Airbnb cash on cash: 7.3%

Traditional cash on cash: 6.53%

Airbnb Rental Income: $4884

Traditional Rental Income: $3560

Airbnb ROI: 7.3%