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
118 CHAR NOR MANOR BOULEVARD CHESTERTOWN, MD An adorable cottage with water views of the Chester River! Nicely maintained cottage featu...	3 beds \| 2 baths \| 1,114 sq.ft.	$289,000	Airbnb cash on cash: 8.03% Traditional cash on cash: 6.32% Airbnb Rental Income: $3452 Traditional Rental Income: $2220 Airbnb ROI: 8.03% Traditional ROI: 6.32%
7500 SHORTALL STREET CHESTERTOWN, MD This charming 3-bedroom, 2-bath rancher nestled in a serene setting of Quaker Estates is a...	3 beds \| 2 baths \| 1,288 sq.ft.	$299,900	Airbnb cash on cash: 7.47% Traditional cash on cash: 5.93% Airbnb Rental Income: $3452 Traditional Rental Income: $2253 Airbnb ROI: 7.47% Traditional ROI: 5.93%
6744 CHURCH HILL ROAD CHESTERTOWN, MD Nestled in a prime suburban commercial zone, this versatile property offers 1,300 sq ft of...	3 beds \| 1 baths \| 1,298 sq.ft.	$349,000	Airbnb cash on cash: 6.33% Traditional cash on cash: 3.77% Airbnb Rental Income: $3452 Traditional Rental Income: $1848 Airbnb ROI: 6.33% Traditional ROI: 3.77%
477 PEAR TREE POINT ROAD CHESTERTOWN, MD Located within the much desired Queen Anne's County School District!! Brand new constructi...	3 beds \| 3 baths \| 1,512 sq.ft.	$399,900	Airbnb cash on cash: 5.29% Traditional cash on cash: 4.7% Airbnb Rental Income: $3452 Traditional Rental Income: $2468 Airbnb ROI: 5.29% Traditional ROI: 4.7%
116 ISLAND LARK WAY CHESTERTOWN, MD Welcome home this beautiful end unit townhome in the newer community of The Village At Che...	3 beds \| 3 baths \| 1,420 sq.ft.	$289,900	Airbnb cash on cash: 7.03% Traditional cash on cash: 6.32% Airbnb Rental Income: $3452 Traditional Rental Income: $2495 Airbnb ROI: 7.03% Traditional ROI: 6.32%
10262 JOHN CARVILL ROAD CHESTERTOWN, MD This beloved waterfront property has been a treasured family gathering place for over twen...	5 beds \| 2 baths \| 3,788 sq.ft.	$1,600,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 0.5% Airbnb Rental Income: $3924 Traditional Rental Income: $3055 Airbnb ROI: 0.52% Traditional ROI: 0.5%
411 FAIRVIEW DRIVE CHESTERTOWN, MD Eastern Shore of Maryland Waterfront Cottage is perched on the banks of Rosin Creek in Que...	3 beds \| 2 baths \| 1,680 sq.ft.	$649,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 2.65% Airbnb Rental Income: $3452 Traditional Rental Income: $2568 Airbnb ROI: 2.85% Traditional ROI: 2.65%
305 LONGFELLOW DRIVE CHESTERTOWN, MD Adorable and Affordable in Chester Harbor community! This 4-bedroom 2 bath home is ready f...	4 beds \| 2 baths \| 1,470 sq.ft.	$322,000	Airbnb cash on cash: 6.59% Traditional cash on cash: 5.89% Airbnb Rental Income: $3306 Traditional Rental Income: $2353 Airbnb ROI: 6.59% Traditional ROI: 5.89%
24543 CHESTERTOWN ROAD CHESTERTOWN, MD Nestled on 10 scenic acres just outside of Chestertown, this spacious 3,280 sq ft home off...	3 beds \| 2 baths \| 3,280 sq.ft.	$475,000	Airbnb cash on cash: 4.05% Traditional cash on cash: 3.36% Airbnb Rental Income: $3452 Traditional Rental Income: $2380 Airbnb ROI: 4.05% Traditional ROI: 3.36%
100 ACORN DRIVE CHESTERTOWN, MD Rare end unit townhome in Oak Hollow. Close to shopping and college. Spacious rooms. Open ...	3 beds \| 3 baths \| 1,930 sq.ft.	$299,000	Airbnb cash on cash: 6.92% Traditional cash on cash: 6.39% Airbnb Rental Income: $3452 Traditional Rental Income: $2539 Airbnb ROI: 6.92% Traditional ROI: 6.39%
109 SECOR ROAD CHESTERTOWN, MD This home is located on a quiet Cul-de-sac in a water access community of Chester Harbor o...	3 beds \| 2 baths \| 1,560 sq.ft.	$365,000	Airbnb cash on cash: 5.9% Traditional cash on cash: 5.63% Airbnb Rental Income: $3452 Traditional Rental Income: $2596 Airbnb ROI: 5.9% Traditional ROI: 5.63%
210 HILLTOP LANE CHESTERTOWN, MD Built in 2005, this beautifully maintained home offers modern comforts and an inviting atm...	3 beds \| 3 baths \| 1,200 sq.ft.	$235,000	Airbnb cash on cash: 9.28% Traditional cash on cash: 7.5% Airbnb Rental Income: $3452 Traditional Rental Income: $2294 Airbnb ROI: 9.28% Traditional ROI: 7.5%
107 DUTCHESS ROAD CHESTERTOWN, MD Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community...	3 beds \| 2 baths \| 1,380 sq.ft.	$369,000	Airbnb cash on cash: 5.96% Traditional cash on cash: 5.06% Airbnb Rental Income: $3452 Traditional Rental Income: $2375 Airbnb ROI: 5.96% Traditional ROI: 5.06%
109 GRANT COURT CHESTERTOWN, MD This meticulously maintained 3-bedroom, 2-bathroom ranch-style home offers the perfect ble...	3 beds \| 2 baths \| 1,344 sq.ft.	$389,900	Airbnb cash on cash: 5.34% Traditional cash on cash: 4.19% Airbnb Rental Income: $3452 Traditional Rental Income: $2268 Airbnb ROI: 5.34% Traditional ROI: 4.19%
202 GLEN STREET CHESTERTOWN, MD Brick rancher located on the corner of Greenwood and Glen Street in College Heights offers...	3 beds \| 1 baths \| 1,252 sq.ft.	$307,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 4.67% Airbnb Rental Income: $3452 Traditional Rental Income: $2025 Airbnb ROI: 6.96% Traditional ROI: 4.67%

Vacation Rentals in Chestertown

There are 15 vacation rental properties available for sale in the city of Chestertown . The median list price of Airbnb properties available for sale in Chestertown is $365,000 and the average price per square foot is $207. The cash on cash return on vacation rentals in Chestertown is 6.00%. The average monthly short term rental income in Chestertown is $3,452.

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

There are 15 Airbnb properties available for sale in Chestertown.

In 2024, the best neighborhood to buy short term rental property is CHESTERTOWN.

In December 2024, the average Airbnb occupancy rate in Chestertown is 49%.

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

118 CHAR NOR MANOR BOULEVARD

CHESTERTOWN, MD

3 beds | 2 baths | 1,114 sq.ft.

$289,000

Airbnb cash on cash: 8.03%

Traditional cash on cash: 6.32%

Airbnb Rental Income: $3452

Traditional Rental Income: $2220

Airbnb ROI: 8.03%

Traditional ROI: 6.32%

7500 SHORTALL STREET

CHESTERTOWN, MD

3 beds | 2 baths | 1,288 sq.ft.

$299,900

Airbnb cash on cash: 7.47%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $3452

Traditional Rental Income: $2253

Airbnb ROI: 7.47%

Traditional ROI: 5.93%

6744 CHURCH HILL ROAD

CHESTERTOWN, MD

3 beds | 1 baths | 1,298 sq.ft.

$349,000

Airbnb cash on cash: 6.33%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $3452

Traditional Rental Income: $1848

Airbnb ROI: 6.33%

Traditional ROI: 3.77%

477 PEAR TREE POINT ROAD

CHESTERTOWN, MD

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

$399,900

Airbnb cash on cash: 5.29%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $3452

Traditional Rental Income: $2468

Airbnb ROI: 5.29%

Traditional ROI: 4.7%

116 ISLAND LARK WAY

CHESTERTOWN, MD

3 beds | 3 baths | 1,420 sq.ft.

$289,900

Airbnb cash on cash: 7.03%

Traditional cash on cash: 6.32%

Airbnb Rental Income: $3452

Traditional Rental Income: $2495

Airbnb ROI: 7.03%

Traditional ROI: 6.32%

10262 JOHN CARVILL ROAD

CHESTERTOWN, MD

5 beds | 2 baths | 3,788 sq.ft.

$1,600,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 0.5%

Airbnb Rental Income: $3924

Traditional Rental Income: $3055

Airbnb ROI: 0.52%

Traditional ROI: 0.5%

411 FAIRVIEW DRIVE

CHESTERTOWN, MD

3 beds | 2 baths | 1,680 sq.ft.

$649,000

Airbnb cash on cash: 2.85%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $3452

Traditional Rental Income: $2568

Airbnb ROI: 2.85%

Traditional ROI: 2.65%

305 LONGFELLOW DRIVE

CHESTERTOWN, MD

4 beds | 2 baths | 1,470 sq.ft.

$322,000

Airbnb cash on cash: 6.59%

Traditional cash on cash: 5.89%

Airbnb Rental Income: $3306

Traditional Rental Income: $2353

Airbnb ROI: 6.59%