Airbnb Properties for Sale in Chester, MD

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

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

Airbnb For Sale in Chester, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1926 SHERMAN DRIVE CHESTER, MD Photo's on the way !! Welcome to Kent Island. This 4 Bedroom 2 Bath property is move in re...	4 beds \| 2 baths \| 1,560 sq.ft.	$429,900	Airbnb cash on cash: 5.06% Traditional cash on cash: 4.56% Airbnb Rental Income: $3496 Traditional Rental Income: $2522 Airbnb ROI: 5.06% Traditional ROI: 4.56%
1004 AUCKLAND WAY CHESTER, MD WOW! MASSIVE PRICE REDUCTION WATER, WATER EVERYWHERE! Waterfront without the worry! En...	3 beds \| 4 baths \| 2,076 sq.ft.	$564,000	Airbnb cash on cash: 8.42% Traditional cash on cash: 4.01% Airbnb Rental Income: $6709 Traditional Rental Income: $3079 Airbnb ROI: 8.42% Traditional ROI: 4.01%
208 MERGANSER CT CHESTER, MD GREAT OPPORTUNITY to own this first-floor end unit. Which does not often come on the mark...	2 beds \| 2 baths \| N/A	$299,900	Airbnb cash on cash: 9.17% Traditional cash on cash: 5.24% Airbnb Rental Income: $4018 Traditional Rental Income: $2050 Airbnb ROI: 9.17% Traditional ROI: 5.24%
206 PRICES LANE CHESTER, MD Experience the charm and tranquility of country living with this incredibly affordable 4-b...	4 beds \| 2 baths \| 1,782 sq.ft.	$330,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 6.41% Airbnb Rental Income: $3496 Traditional Rental Income: $2554 Airbnb ROI: 6.96% Traditional ROI: 6.41%
141 SWITCHGRASS WAY #34 CHESTER, MD K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesape...	3 beds \| 3 baths \| 2,600 sq.ft.	$679,500	Airbnb cash on cash: 6.22% Traditional cash on cash: 2.5% Airbnb Rental Income: $6709 Traditional Rental Income: $3044 Airbnb ROI: 6.22% Traditional ROI: 2.5%
200 HARRIER WAY #31 CHESTER, MD Luxury Resort Style Living!! Four Seasons at Kent Island is an active 55+ community. When...	3 beds \| 3 baths \| N/A	$689,900	Airbnb cash on cash: 6.48% Traditional cash on cash: 2.26% Airbnb Rental Income: $6709 Traditional Rental Income: $2686 Airbnb ROI: 6.48% Traditional ROI: 2.26%
4000 HERONS NEST WAY #22 CHESTER, MD New Listing! Four Seasons @ Kent Island - 55+ Community - Turn Key & Lovely 2nd Floor Con...	2 beds \| 3 baths \| 1,900 sq.ft.	$599,900	Airbnb cash on cash: 3.3% Traditional cash on cash: 3.15% Airbnb Rental Income: $4018 Traditional Rental Income: $3075 Airbnb ROI: 3.3% Traditional ROI: 3.15%
703 BLENNY LANE CHESTER, MD This beautiful Bayside boasts an open floor plan with gorgeous views. Not ready to buy? R...	3 beds \| 4 baths \| 2,172 sq.ft.	$534,900	Airbnb cash on cash: 8.9% Traditional cash on cash: 5.4% Airbnb Rental Income: $6709 Traditional Rental Income: $3649 Airbnb ROI: 8.9% Traditional ROI: 5.4%
300 DRAKE TAIL PL CHESTER, MD Just reduced $10000 on 10/9/24 Well- Maintained END UNIT CHESTER RIVER TOWNHOME in AMENITY...	2 beds \| 3 baths \| N/A	$305,000	Airbnb cash on cash: 8.9% Traditional cash on cash: 6.83% Airbnb Rental Income: $4018 Traditional Rental Income: $2566 Airbnb ROI: 8.9% Traditional ROI: 6.83%
307 SCHOONER WAY #42 CHESTER, MD Nestled in the heart of the Bayside Community overlooking the pond, this immaculate 2 ( po...	2 beds \| 3 baths \| 1,747 sq.ft.	$364,900	Airbnb cash on cash: 5.37% Traditional cash on cash: 4.22% Airbnb Rental Income: $4018 Traditional Rental Income: $2766 Airbnb ROI: 5.37% Traditional ROI: 4.22%
15 QUEEN ANNE WAY #E CHESTER, MD If youâre a water enthusiast, this stunning 2.5-level townhome offers the perfect blend ...	2 beds \| 3 baths \| 1,680 sq.ft.	$559,750	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.97% Airbnb Rental Income: $4018 Traditional Rental Income: $2997 Airbnb ROI: 4.28% Traditional ROI: 3.97%
4000 HERONS NEST WAY #44 CHESTER, MD ** SPACIOUS PENTHOUSE CONDO. LOVELY VIEWS OF MACUM CREEK** The Severn model is a s...	3 beds \| 3 baths \| 2,602 sq.ft.	$689,500	Airbnb cash on cash: 6.14% Traditional cash on cash: 2.47% Airbnb Rental Income: $6709 Traditional Rental Income: $3044 Airbnb ROI: 6.14% Traditional ROI: 2.47%

Vacation Rentals in Chester

There are 12 vacation rental properties available for sale in the city of Chester . The median list price of Airbnb properties available for sale in Chester is $569,077 and the average price per square foot is $257. The cash on cash return on vacation rentals in Chester is 5.00%. The average monthly short term rental income in Chester is $4,018.

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

There are 12 Airbnb properties available for sale in Chester.

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

In November 2024, the average Airbnb occupancy rate in Chester is 47%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Chester, MD

1926 SHERMAN DRIVE

CHESTER, MD

4 beds | 2 baths | 1,560 sq.ft.

$429,900

Airbnb cash on cash: 5.06%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $3496

Traditional Rental Income: $2522

Airbnb ROI: 5.06%

Traditional ROI: 4.56%

1004 AUCKLAND WAY

CHESTER, MD

3 beds | 4 baths | 2,076 sq.ft.

$564,000

Airbnb cash on cash: 8.42%

Traditional cash on cash: 4.01%

Airbnb Rental Income: $6709

Traditional Rental Income: $3079

Airbnb ROI: 8.42%

Traditional ROI: 4.01%

208 MERGANSER CT

CHESTER, MD

2 beds | 2 baths | N/A

$299,900

Airbnb cash on cash: 9.17%

Traditional cash on cash: 5.24%

Airbnb Rental Income: $4018

Traditional Rental Income: $2050

Airbnb ROI: 9.17%

Traditional ROI: 5.24%

206 PRICES LANE

CHESTER, MD

4 beds | 2 baths | 1,782 sq.ft.

$330,000

Airbnb cash on cash: 6.96%

Traditional cash on cash: 6.41%

Airbnb Rental Income: $3496

Traditional Rental Income: $2554

Airbnb ROI: 6.96%

Traditional ROI: 6.41%

141 SWITCHGRASS WAY #34

CHESTER, MD

3 beds | 3 baths | 2,600 sq.ft.

$679,500

Airbnb cash on cash: 6.22%

Traditional cash on cash: 2.5%

Airbnb Rental Income: $6709

Traditional Rental Income: $3044

Airbnb ROI: 6.22%

Traditional ROI: 2.5%

200 HARRIER WAY #31

CHESTER, MD

3 beds | 3 baths | N/A

$689,900

Airbnb cash on cash: 6.48%

Traditional cash on cash: 2.26%

Airbnb Rental Income: $6709

Traditional Rental Income: $2686

Airbnb ROI: 6.48%

Traditional ROI: 2.26%

4000 HERONS NEST WAY #22

CHESTER, MD

2 beds | 3 baths | 1,900 sq.ft.

$599,900

Airbnb cash on cash: 3.3%

Traditional cash on cash: 3.15%

Airbnb Rental Income: $4018

Traditional Rental Income: $3075

Airbnb ROI: 3.3%

Traditional ROI: 3.15%

703 BLENNY LANE

CHESTER, MD

3 beds | 4 baths | 2,172 sq.ft.

$534,900

Airbnb cash on cash: 8.9%

Traditional cash on cash: 5.4%

Airbnb Rental Income: $6709

Traditional Rental Income: $3649

Airbnb ROI: 8.9%