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
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%
7517 SUNBURST AVENUE CHESTERTOWN, MD Almost new home in Chestertown! Modern three bed, two bath rancher with split floor plan....	3 beds \| 2 baths \| 1,320 sq.ft.	$254,900	Airbnb cash on cash: 8.93% Traditional cash on cash: 6.97% Airbnb Rental Income: $3452 Traditional Rental Income: $2215 Airbnb ROI: 8.93% Traditional ROI: 6.97%
203 HILLTOP LANE CHESTERTOWN, MD Built in 2005, this like-new home boasts an open floor plan with inviting, bright spaces. ...	3 beds \| 3 baths \| 1,222 sq.ft.	$225,000	Airbnb cash on cash: 9.75% Traditional cash on cash: 7.79% Airbnb Rental Income: $3452 Traditional Rental Income: $2271 Airbnb ROI: 9.75% Traditional ROI: 7.79%
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%
1316 EWINGTOWN ROAD CHESTERTOWN, MD Welcome to 1316 Ewingtown Rd, where the charm of historic Chestertown meets the tranquilit...	4 beds \| 2 baths \| 2,476 sq.ft.	$625,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 2.56% Airbnb Rental Income: $3306 Traditional Rental Income: $2502 Airbnb ROI: 2.67% Traditional ROI: 2.56%
24291 CHESTERTOWN ROAD CHESTERTOWN, MD Price Improvement - Welcome to this delightful brick rancher, offering over 1,500 square f...	3 beds \| 2 baths \| 1,536 sq.ft.	$342,000	Airbnb cash on cash: 6.48% Traditional cash on cash: 5.08% Airbnb Rental Income: $3452 Traditional Rental Income: $2239 Airbnb ROI: 6.48% Traditional ROI: 5.08%
481 PEAR TREE POINT ROAD CHESTERTOWN, MD Major Price Reduction - Brand New Home ready ready for ALL your Holiday Celebrations! Law...	3 beds \| 3 baths \| 1,512 sq.ft.	$374,900	Airbnb cash on cash: 6.25% Traditional cash on cash: 5.89% Airbnb Rental Income: $3452 Traditional Rental Income: $2562 Airbnb ROI: 6.25% Traditional ROI: 5.89%
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: 5.8% Traditional cash on cash: 5.22% Airbnb Rental Income: $3452 Traditional Rental Income: $2468 Airbnb ROI: 5.8% Traditional ROI: 5.22%
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.	$289,000	Airbnb cash on cash: 7.05% Traditional cash on cash: 6.35% Airbnb Rental Income: $3452 Traditional Rental Income: $2495 Airbnb ROI: 7.05% Traditional ROI: 6.35%
228 CONCORD ROAD CHESTERTOWN, MD This 1500 sq. foot rancher sits on a nice open lot with plenty of parking and room to grow...	4 beds \| 2 baths \| 1,500 sq.ft.	$329,000	Airbnb cash on cash: 6.52% Traditional cash on cash: 6.32% Airbnb Rental Income: $3306 Traditional Rental Income: $2505 Airbnb ROI: 6.52% 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%
221 RIVER ROAD CHESTERTOWN, MD Hidden within the wandering gardens, you will find this meticulously maintained home with...	5 beds \| 2 baths \| 2,240 sq.ft.	$399,000	Airbnb cash on cash: 6.3% Traditional cash on cash: 5.57% Airbnb Rental Income: $3924 Traditional Rental Income: $2805 Airbnb ROI: 6.3% Traditional ROI: 5.57%
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.	$499,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 3.15% Airbnb Rental Income: $3452 Traditional Rental Income: $2380 Airbnb ROI: 3.81% Traditional ROI: 3.15%
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%

Vacation Rentals in Chestertown

There are 16 vacation rental properties available for sale in the city of Chestertown . The median list price of Airbnb properties available for sale in Chestertown is $386,950 and the average price per square foot is $202. 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 16 Airbnb properties available for sale in Chestertown.

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

In November 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

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%

7517 SUNBURST AVENUE

CHESTERTOWN, MD

3 beds | 2 baths | 1,320 sq.ft.

$254,900

Airbnb cash on cash: 8.93%

Traditional cash on cash: 6.97%

Airbnb Rental Income: $3452

Traditional Rental Income: $2215

Airbnb ROI: 8.93%

Traditional ROI: 6.97%

203 HILLTOP LANE

CHESTERTOWN, MD

3 beds | 3 baths | 1,222 sq.ft.

$225,000

Airbnb cash on cash: 9.75%

Traditional cash on cash: 7.79%

Airbnb Rental Income: $3452

Traditional Rental Income: $2271

Airbnb ROI: 9.75%

Traditional ROI: 7.79%

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%

1316 EWINGTOWN ROAD

CHESTERTOWN, MD

4 beds | 2 baths | 2,476 sq.ft.

$625,000

Airbnb cash on cash: 2.67%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $3306

Traditional Rental Income: $2502

Airbnb ROI: 2.67%

Traditional ROI: 2.56%

24291 CHESTERTOWN ROAD

CHESTERTOWN, MD

3 beds | 2 baths | 1,536 sq.ft.

$342,000

Airbnb cash on cash: 6.48%

Traditional cash on cash: 5.08%

Airbnb Rental Income: $3452

Traditional Rental Income: $2239

Airbnb ROI: 6.48%

Traditional ROI: 5.08%

481 PEAR TREE POINT ROAD

CHESTERTOWN, MD

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

$374,900

Airbnb cash on cash: 6.25%

Traditional cash on cash: 5.89%

Airbnb Rental Income: $3452

Traditional Rental Income: $2562

Airbnb ROI: 6.25%

Traditional ROI: 5.89%

477 PEAR TREE POINT ROAD

CHESTERTOWN, MD

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

$399,900

Airbnb cash on cash: 5.8%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $3452

Traditional Rental Income: $2468

Airbnb ROI: 5.8%