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
34-E QUEEN ANNE Way CHESTER, MD Price Improvement on this CHESTER RIVER WATERFRONT Eastern Shore! Nestled within the water...	2 beds \| 3 baths \| 1,104 sq.ft.	$469,000	Airbnb cash on cash: 6% Traditional cash on cash: 4.56% Airbnb Rental Income: $4662 Traditional Rental Income: $3067 Airbnb ROI: 6% Traditional ROI: 4.56%
312 BLENNY Lane CHESTER, MD You do not want to miss this opportunity to enjoy island living in this maintenance free, ...	3 beds \| 4 baths \| 1,899 sq.ft.	$479,000	Airbnb cash on cash: 9.44% Traditional cash on cash: 4.77% Airbnb Rental Income: $6279 Traditional Rental Income: $2950 Airbnb ROI: 9.44% Traditional ROI: 4.77%
1401 CALVERT Road CHESTER, MD Kent Island - Marling Farms - Brick Rancher - Waterviews of Crab Alley Bay - PRICE REDUCED...	2 beds \| 2 baths \| 1,444 sq.ft.	$469,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 3.44% Airbnb Rental Income: $4662 Traditional Rental Income: $2336 Airbnb ROI: 6.53% Traditional ROI: 3.44%
141 SWITCHGRASS Way unit: 34 #34 CHESTER, MD ** NICE VIEWS OF THE CHESTER RIVER * LOWEST PRICED SEVERN MODEL** K Hovnanian'...	3 beds \| 3 baths \| 2,600 sq.ft.	$684,950	Airbnb cash on cash: 5.57% Traditional cash on cash: 2.44% Airbnb Rental Income: $6279 Traditional Rental Income: $3044 Airbnb ROI: 5.57% Traditional ROI: 2.44%
170 HARRIER WAY #34 CHESTER, MD Just reduced by $55,000 to $740,000 with immediate availability. Open House this Sunday 9/...	3 beds \| 3 baths \| N/A	$740,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 2.47% Airbnb Rental Income: $6279 Traditional Rental Income: $2981 Airbnb ROI: 5.46% Traditional ROI: 2.47%
170 HARRIER Way unit: 11 #11 CHESTER, MD Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bed...	2 beds \| 3 baths \| 2,003 sq.ft.	$499,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 4.02% Airbnb Rental Income: $4662 Traditional Rental Income: $3099 Airbnb ROI: 5.3% Traditional ROI: 4.02%
190 HARRIER Way unit: 11 #11 CHESTER, MD Luxury 55+ Living at Four Seasons on Kent Island - Move-In Ready & Priced to Sell! Welcome...	2 beds \| 3 baths \| 2,003 sq.ft.	$540,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 2.17% Airbnb Rental Income: $4662 Traditional Rental Income: $2354 Airbnb ROI: 4.83% Traditional ROI: 2.17%
1000 HERONS NEST Way unit: 32 #32 CHESTER, MD Move in this May and enjoy low-maintenance living in the sought-after 55+ community of Fou...	2 beds \| 2 baths \| N/A	$499,000	Airbnb cash on cash: 5.26% Traditional cash on cash: 2.75% Airbnb Rental Income: $4662 Traditional Rental Income: $2521 Airbnb ROI: 5.26% Traditional ROI: 2.75%
154 HARRIER WAY CHESTER, MD * WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND* Price Reduced! Better th...	2 beds \| 2 baths \| 1,900 sq.ft.	$639,545	Airbnb cash on cash: 3.75% Traditional cash on cash: 1.13% Airbnb Rental Income: $4662 Traditional Rental Income: $2132 Airbnb ROI: 3.75% Traditional ROI: 1.13%
47-D QUEEN ANNE Way CHESTER, MD New Price- Owner has relocated & says sell it! Enjoy resort style living every day in the ...	2 beds \| 3 baths \| 1,550 sq.ft.	$549,500	Airbnb cash on cash: 5.45% Traditional cash on cash: 2.26% Airbnb Rental Income: $4662 Traditional Rental Income: $2059 Airbnb ROI: 5.45% Traditional ROI: 2.26%
2865 COX NECK RD CHESTER, MD An impressive open two-story foyer welcomes you to this custom 4 BR, 3.5BA waterfront resi...	4 beds \| 4 baths \| N/A	$2,259,000	Airbnb cash on cash: 0.39% Traditional cash on cash: -0.02% Airbnb Rental Income: $5802 Traditional Rental Income: $3777 Airbnb ROI: 0.39% Traditional ROI: -0.02%
1340 QUEEN ANNE Drive CHESTER, MD Discover the charm of this fully updated ranch in a serene, water-privileged community! Wi...	3 beds \| 2 baths \| 1,248 sq.ft.	$464,900	Airbnb cash on cash: 9.84% Traditional cash on cash: 3.75% Airbnb Rental Income: $6279 Traditional Rental Income: $2393 Airbnb ROI: 9.84% Traditional ROI: 3.75%
114 ADDISON Court CHESTER, MD REDUCED "Shiny and new" might be the best way to describe the feel of this lovely 3 be...	3 beds \| 3 baths \| 2,342 sq.ft.	$549,900	Airbnb cash on cash: 7.82% Traditional cash on cash: 4.06% Airbnb Rental Income: $6279 Traditional Rental Income: $3111 Airbnb ROI: 7.82% Traditional ROI: 4.06%
132 CLAIBORNE Street CHESTER, MD Set on a rare, level, oversized lot in sought-after Gibson's Grant, this inviting front-po...	3 beds \| 4 baths \| 2,400 sq.ft.	$660,000	Airbnb cash on cash: 5.7% Traditional cash on cash: 2.67% Airbnb Rental Income: $6279 Traditional Rental Income: $3180 Airbnb ROI: 5.7% Traditional ROI: 2.67%
1000 HERONS NEST Way unit: 22 #22 CHESTER, MD Welcome to 1000 Heron's Nest Way. This Chester model has scenic, seasonal views of Macum C...	2 beds \| 3 baths \| 1,900 sq.ft.	$488,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.47% Airbnb Rental Income: $4662 Traditional Rental Income: $3249 Airbnb ROI: 5.44% Traditional ROI: 4.47%
108 BODYS NECK Road CHESTER, MD Experience Autumn Serenity on the Waterfront Discover the perfect blend of coastal charm a...	3 beds \| 3 baths \| 1,791 sq.ft.	$499,900	Airbnb cash on cash: 8.88% Traditional cash on cash: 4.8% Airbnb Rental Income: $6279 Traditional Rental Income: $3136 Airbnb ROI: 8.88% Traditional ROI: 4.8%
224 BAYBERRY Drive CHESTER, MD Welcome to Easy Living on the Eastern Shore! *** Discover the perfect blend of comfort, st...	2 beds \| 2 baths \| 1,913 sq.ft.	$599,900	Airbnb cash on cash: 4.64% Traditional cash on cash: 2.78% Airbnb Rental Income: $4662 Traditional Rental Income: $2652 Airbnb ROI: 4.64% Traditional ROI: 2.78%
315 CROSS CREEK CT CHESTER, MD You are going to love this bright and spacious home providing almost 2400 feet of living s...	4 beds \| 3 baths \| N/A	$569,900	Airbnb cash on cash: 6.87% Traditional cash on cash: 4.16% Airbnb Rental Income: $5802 Traditional Rental Income: $3208 Airbnb ROI: 6.87% Traditional ROI: 4.16%
30-C QUEEN MARY Court CHESTER, MD OPEN HOUSE SAT 11/1 11a-1p! Enjoy low-maintenance living in the desirable waterfront commu...	2 beds \| 3 baths \| 1,440 sq.ft.	$339,900	Airbnb cash on cash: 9.59% Traditional cash on cash: 5.9% Airbnb Rental Income: $4662 Traditional Rental Income: $2518 Airbnb ROI: 9.59% Traditional ROI: 5.9%
26-L QUEEN ANNE Way CHESTER, MD Charming Waterfront Condo with Resort-Style Living. Enjoy vacation vibes every day in this...	2 beds \| 2 baths \| 1,104 sq.ft.	$395,000	Airbnb cash on cash: 8.22% Traditional cash on cash: 4.29% Airbnb Rental Income: $4662 Traditional Rental Income: $2239 Airbnb ROI: 8.22% Traditional ROI: 4.29%
3000 HERONS NEST Way unit: 11 #11 CHESTER, MD Love Where You Live! Experience resort-style living that blends comfort, luxury, and conve...	2 beds \| 3 baths \| 2,003 sq.ft.	$555,900	Airbnb cash on cash: 5.2% Traditional cash on cash: 4% Airbnb Rental Income: $4662 Traditional Rental Income: $3069 Airbnb ROI: 5.2% Traditional ROI: 4%
202 MCHENNY Court CHESTER, MD Beautiful Home in Gibson's Grant with Elevator, Open Floor Plan & Two-Car Garage Welcome t...	3 beds \| 3 baths \| 2,520 sq.ft.	$875,000	Airbnb cash on cash: 4.42% Traditional cash on cash: 2.05% Airbnb Rental Income: $6279 Traditional Rental Income: $3114 Airbnb ROI: 4.42% Traditional ROI: 2.05%
162 KIRWANS LANDING Lane CHESTER, MD Private Waterfront Living in Kirwans Landing!Nestled on 1.4 acres in the water-privileged ...	4 beds \| 3 baths \| 2,404 sq.ft.	$979,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.64% Airbnb Rental Income: $5802 Traditional Rental Income: $3870 Airbnb ROI: 3.49% Traditional ROI: 2.64%
HARBOR Drive CHESTER, MD New home being built! Act now and pick all your colors! Finished models can be seen! Call ...	3 beds \| 2 baths \| 1,250 sq.ft.	$499,900	Airbnb cash on cash: 9.29% Traditional cash on cash: 3.96% Airbnb Rental Income: $6279 Traditional Rental Income: $2554 Airbnb ROI: 9.29% Traditional ROI: 3.96%

Vacation Rentals in Chester

There are 25 vacation rental properties available for sale in the city of Chester . The median list price of Airbnb properties available for sale in Chester is $499,900 and the average price per square foot is $274. The cash on cash return on vacation rentals in Chester is 6.00%. The average monthly short term rental income in Chester is $5,232.

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

There are 25 Airbnb properties available for sale in Chester.

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

In November 2025, the average Airbnb occupancy rate in Chester is 38%.

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

34-E QUEEN ANNE Way

CHESTER, MD

2 beds | 3 baths | 1,104 sq.ft.

$469,000

Airbnb cash on cash: 6%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $4662

Traditional Rental Income: $3067

Airbnb ROI: 6%

Traditional ROI: 4.56%

312 BLENNY Lane

CHESTER, MD

3 beds | 4 baths | 1,899 sq.ft.

$479,000

Airbnb cash on cash: 9.44%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $6279

Traditional Rental Income: $2950

Airbnb ROI: 9.44%

Traditional ROI: 4.77%

1401 CALVERT Road

CHESTER, MD

2 beds | 2 baths | 1,444 sq.ft.

$469,000

Airbnb cash on cash: 6.53%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $4662

Traditional Rental Income: $2336

Airbnb ROI: 6.53%

Traditional ROI: 3.44%

141 SWITCHGRASS Way unit: 34 #34

CHESTER, MD

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

$684,950

Airbnb cash on cash: 5.57%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $6279

Traditional Rental Income: $3044

Airbnb ROI: 5.57%

Traditional ROI: 2.44%

170 HARRIER WAY #34

CHESTER, MD

3 beds | 3 baths | N/A

$740,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $6279

Traditional Rental Income: $2981

Airbnb ROI: 5.46%

Traditional ROI: 2.47%

170 HARRIER Way unit: 11 #11

CHESTER, MD

2 beds | 3 baths | 2,003 sq.ft.

$499,000

Airbnb cash on cash: 5.3%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $4662

Traditional Rental Income: $3099

Airbnb ROI: 5.3%

Traditional ROI: 4.02%

190 HARRIER Way unit: 11 #11

CHESTER, MD

2 beds | 3 baths | 2,003 sq.ft.

$540,000

Airbnb cash on cash: 4.83%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $4662

Traditional Rental Income: $2354

Airbnb ROI: 4.83%

Traditional ROI: 2.17%

1000 HERONS NEST Way unit: 32 #32

CHESTER, MD

2 beds | 2 baths | N/A

$499,000

Airbnb cash on cash: 5.26%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $4662

Traditional Rental Income: $2521

Airbnb ROI: 5.26%