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
1363 Calvert Rd CHESTER, MD A MUST SEE home with complete rehab/remodel in 2017 with crown molding throughout, new ap...	3 beds \| 2 baths \| 1,400 sq.ft.	$469,999	Airbnb cash on cash: 9.66% Traditional cash on cash: 3.09% Airbnb Rental Income: $6279 Traditional Rental Income: $2152 Airbnb ROI: 9.66% Traditional ROI: 3.09%
3000 Herons Nest Way #11 CHESTER, MD Call today to find out the details and start living the life you want. Welcome to a new a...	2 beds \| 2 baths \| 2,003 sq.ft.	$555,900	Airbnb cash on cash: 2.74% Traditional cash on cash: 0.71% Airbnb Rental Income: $4662 Traditional Rental Income: $2646 Airbnb ROI: 2.74% Traditional ROI: 0.71%
402 Blenny Ln CHESTER, MD End-unit three-level townhome overlooking the pond in Bayside community. Freshly painted, ...	3 beds \| 3 baths \| 1,747 sq.ft.	$399,000	Airbnb cash on cash: 9.71% Traditional cash on cash: 5.93% Airbnb Rental Income: $6279 Traditional Rental Income: $3629 Airbnb ROI: 9.71% Traditional ROI: 5.93%
1401 Calvert Rd CHESTER, MD MARLING FARMS -Waterviews of Crab Alley Bay - PRICE REDUCED -Brick Rancher- All on ONE LEV...	2 beds \| 2 baths \| 1,444 sq.ft.	$454,900	Airbnb cash on cash: 6.77% Traditional cash on cash: 3.57% Airbnb Rental Income: $4662 Traditional Rental Income: $2336 Airbnb ROI: 6.77% Traditional ROI: 3.57%
170 Harrier Way #34 CHESTER, MD New year, new price!! This is one of only two 3-bedroom condos on the market in Four Seas...	3 beds \| 2 baths \| 2,602 sq.ft.	$699,900	Airbnb cash on cash: 5.77% Traditional cash on cash: 2.61% Airbnb Rental Income: $6279 Traditional Rental Income: $2981 Airbnb ROI: 5.77% Traditional ROI: 2.61%
190 Harrier Way #11 CHESTER, MD Luxury 55+ Living at Four Seasons on Kent Island - Move-In Ready & Priced to Sell! Welcome...	2 beds \| 2 baths \| 2,003 sq.ft.	$540,000	Airbnb cash on cash: 3.92% Traditional cash on cash: 1.26% Airbnb Rental Income: $4662 Traditional Rental Income: $2354 Airbnb ROI: 3.92% Traditional ROI: 1.26%
306 Teal Ct #C CHESTER, MD	2 beds \| 2 baths \| 1,073 sq.ft.	$279,900	Airbnb cash on cash: 9.87% Traditional cash on cash: 2.9% Airbnb Rental Income: $4662 Traditional Rental Income: $1858 Airbnb ROI: 9.87% Traditional ROI: 2.9%
200 Harrier Way #21 CHESTER, MD The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2...	3 beds \| 2 baths \| 2,600 sq.ft.	$674,900	Airbnb cash on cash: 4.99% Traditional cash on cash: 1.56% Airbnb Rental Income: $6279 Traditional Rental Income: $2881 Airbnb ROI: 4.99% Traditional ROI: 1.56%
1000 Herons Nest Way #32 CHESTER, MD Move in this May and enjoy low-maintenance living in the sought-after 55+ community of Fou...	2 beds \| 2 baths \| 1,900 sq.ft.	$499,000	Airbnb cash on cash: 3.51% Traditional cash on cash: 0.99% Airbnb Rental Income: $4662 Traditional Rental Income: $2521 Airbnb ROI: 3.51% Traditional ROI: 0.99%
154 HARRIER WAY CHESTER, MD * WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND* Price Reduced! Lowest pr...	2 beds \| 2 baths \| 1,900 sq.ft.	$639,450	Airbnb cash on cash: 3.73% Traditional cash on cash: 1.11% Airbnb Rental Income: $4662 Traditional Rental Income: $2132 Airbnb ROI: 3.73% Traditional ROI: 1.11%
4000 Herons Nest Way #22 CHESTER, MD Four Seasons @ Kent Island - 55+ Community - $10,000 Closing Cost Assistance Available - T...	2 beds \| 2 baths \| 1,900 sq.ft.	$560,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 1.79% Airbnb Rental Income: $4662 Traditional Rental Income: $3075 Airbnb ROI: 2.98% Traditional ROI: 1.79%
201 Golden Eye Ct CHESTER, MD Bright, welcoming lower level end unit condo in a water-oriented community on Kent Island...	2 beds \| 2 baths \| 1,073 sq.ft.	$285,000	Airbnb cash on cash: 9.86% Traditional cash on cash: 3.09% Airbnb Rental Income: $4662 Traditional Rental Income: $1878 Airbnb ROI: 9.86% Traditional ROI: 3.09%
807 Auckland Way CHESTER, MD Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier ...	3 beds \| 3 baths \| 2,100 sq.ft.	$425,000	Airbnb cash on cash: 8.67% Traditional cash on cash: 4.76% Airbnb Rental Income: $6279 Traditional Rental Income: $3486 Airbnb ROI: 8.67% Traditional ROI: 4.76%
1906 Harbor Dr CHESTER, MD Great opportunity for a savvy investor to buy way below market value. This 3 brm 2 ba ranc...	3 beds \| 2 baths \| 1,750 sq.ft.	$499,900	Airbnb cash on cash: 9.03% Traditional cash on cash: 3.56% Airbnb Rental Income: $6279 Traditional Rental Income: $2487 Airbnb ROI: 9.03% Traditional ROI: 3.56%
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%
Harbor Dr 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: 9.28% Traditional cash on cash: 3.95% Airbnb Rental Income: $6279 Traditional Rental Income: $2554 Airbnb ROI: 9.28% Traditional ROI: 3.95%
112 Chessie Ct CHESTER, MD Step inside and see this meticulously cared for home! This home features a first floor pri...	3 beds \| 2 baths \| 2,066 sq.ft.	$519,900	Airbnb cash on cash: 8.32% Traditional cash on cash: 4.16% Airbnb Rental Income: $6279 Traditional Rental Income: $3022 Airbnb ROI: 8.32% Traditional ROI: 4.16%
1916 Stevens Dr CHESTER, MD Discover this beautifully updated 3-bedroom, 2 full and 1 half bathroom home located on a ...	3 beds \| 2 baths \| 1,728 sq.ft.	$495,000	Airbnb cash on cash: 9.05% Traditional cash on cash: 4.38% Airbnb Rental Income: $6279 Traditional Rental Income: $2880 Airbnb ROI: 9.05% Traditional ROI: 4.38%
1704 Bayside Dr CHESTER, MD Discover a true waterfront treasure on .54 acres with 110 feet of waterfront. This beautif...	3 beds \| 2 baths \| 1,830 sq.ft.	$1,100,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 1.49% Airbnb Rental Income: $6279 Traditional Rental Income: $3259 Airbnb ROI: 3.24% Traditional ROI: 1.49%
54-H Queen Caroline Ct CHESTER, MD Nothing to do but move in! This roomy 2 bedroom, 2.5 bathroom end unit has been completel...	2 beds \| 2 baths \| 1,280 sq.ft.	$349,000	Airbnb cash on cash: 7.53% Traditional cash on cash: 2.55% Airbnb Rental Income: $4662 Traditional Rental Income: $2064 Airbnb ROI: 7.53% Traditional ROI: 2.55%
15-E Queen Anne Way #E CHESTER, MD Escape to the water - without the waterfront price. This Chester River-front townhome in Q...	2 beds \| 2 baths \| 1,680 sq.ft.	$480,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 3.85% Airbnb Rental Income: $4662 Traditional Rental Income: $3186 Airbnb ROI: 4.99% Traditional ROI: 3.85%
4000 HERONS NEST Way unit: 22 #22 CHESTER, MD ** New Listing! Four Seasons @ Kent Island - 55+ Community - Turnkey & Lovely 2nd Floor Co...	2 beds \| 3 baths \| 1,900 sq.ft.	$560,000	Airbnb cash on cash: 5.1% Traditional cash on cash: 3.83% Airbnb Rental Income: $4662 Traditional Rental Income: $3029 Airbnb ROI: 5.1% Traditional ROI: 3.83%
176 Flagstaff Way #33 CHESTER, MD 176 Flagstaff Way #33, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$869,990	Airbnb cash on cash: 2.36% Traditional cash on cash: 0.93% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 2.36% Traditional ROI: 0.93%
176 Flagstaff Way #43 CHESTER, MD 176 Flagstaff Way #43, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$1,021,990	Airbnb cash on cash: 1.71% Traditional cash on cash: 0.49% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 1.71% Traditional ROI: 0.49%
259 Redstart Dr CHESTER, MD 259 Redstart Dr, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 2,791 sq.ft.	$829,990	Airbnb cash on cash: 3.43% Traditional cash on cash: 0.97% Airbnb Rental Income: $5802 Traditional Rental Income: $2745 Airbnb ROI: 3.43% Traditional ROI: 0.97%
176 Flagstaff Way #2443 CHESTER, MD 176 Flagstaff Way #2443, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$1,021,990	Airbnb cash on cash: 1% Traditional cash on cash: -0.22% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 1% Traditional ROI: -0.22%
176 Flagstaff Way #2433 CHESTER, MD 176 Flagstaff Way #2433, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$869,990	Airbnb cash on cash: 1.54% Traditional cash on cash: 0.11% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 1.54% Traditional ROI: 0.11%
141 Redstart Dr CHESTER, MD 141 Redstart Dr, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,789 sq.ft.	$1,019,990	Airbnb cash on cash: 2.83% Traditional cash on cash: 0.28% Airbnb Rental Income: $6279 Traditional Rental Income: $2627 Airbnb ROI: 2.83% Traditional ROI: 0.28%
176 Flagstaff Way #12 CHESTER, MD 176 Flagstaff Way #12, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$699,990	Airbnb cash on cash: 3.44% Traditional cash on cash: 1.74% Airbnb Rental Income: $4662 Traditional Rental Income: $2590 Airbnb ROI: 3.44% Traditional ROI: 1.74%
1757 Harbor Dr CHESTER, MD 1757 Harbor Dr, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| N/A	$1,167,890	Airbnb cash on cash: 2.1% Traditional cash on cash: 0.16% Airbnb Rental Income: $5802 Traditional Rental Income: $2541 Airbnb ROI: 2.1% Traditional ROI: 0.16%
176 Flagstaff Way #2411 CHESTER, MD 176 Flagstaff Way #2411, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$699,990	Airbnb cash on cash: 2.41% Traditional cash on cash: 0.72% Airbnb Rental Income: $4662 Traditional Rental Income: $2590 Airbnb ROI: 2.41% Traditional ROI: 0.72%
176 Flagstaff Way #11 CHESTER, MD 176 Flagstaff Way #11, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$699,990	Airbnb cash on cash: 3.44% Traditional cash on cash: 1.74% Airbnb Rental Income: $4662 Traditional Rental Income: $2590 Airbnb ROI: 3.44% Traditional ROI: 1.74%
176 Flagstaff Way #2412 CHESTER, MD 176 Flagstaff Way #2412, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$699,990	Airbnb cash on cash: 2.41% Traditional cash on cash: 0.72% Airbnb Rental Income: $4662 Traditional Rental Income: $2590 Airbnb ROI: 2.41% Traditional ROI: 0.72%
117 Flycatcher Way CHESTER, MD 117 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,930 sq.ft.	$1,400,000	Airbnb cash on cash: 1.5% Traditional cash on cash: -0.36% Airbnb Rental Income: $6279 Traditional Rental Income: $2627 Airbnb ROI: 1.5% Traditional ROI: -0.36%
123 Flycatcher Way CHESTER, MD 123 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,789 sq.ft.	$1,300,000	Airbnb cash on cash: 1.77% Traditional cash on cash: -0.23% Airbnb Rental Income: $6279 Traditional Rental Income: $2627 Airbnb ROI: 1.77% Traditional ROI: -0.23%
135 Nauset Ln CHESTER, MD 135 Nauset Ln, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,399 sq.ft.	$814,900	Airbnb cash on cash: 3.99% Traditional cash on cash: 0.76% Airbnb Rental Income: $6279 Traditional Rental Income: $2587 Airbnb ROI: 3.99% Traditional ROI: 0.76%
127 Flycatcher Way CHESTER, MD 127 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	2 beds \| 2 baths \| 1,993 sq.ft.	$1,100,000	Airbnb cash on cash: 1.15% Traditional cash on cash: -0.39% Airbnb Rental Income: $4662 Traditional Rental Income: $2121 Airbnb ROI: 1.15% Traditional ROI: -0.39%
132 Wheelhouse Way #43 CHESTER, MD 132 Wheelhouse Way #43, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$1,350,000	Airbnb cash on cash: 0.79% Traditional cash on cash: -0.14% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 0.79% Traditional ROI: -0.14%
132 Wheelhouse Way CHESTER, MD 132 Wheelhouse Way, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$1,299,990	Airbnb cash on cash: 0.35% Traditional cash on cash: -0.61% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 0.35% Traditional ROI: -0.61%
Bernstein II Plan CHESTER, MD Bernstein II Plan, CHESTER, MD 21619 \| Single Family Residential	2 beds \| 2 baths \| 1,690 sq.ft.	$599,990	Airbnb cash on cash: 4.35% Traditional cash on cash: 1.05% Airbnb Rental Income: $4662 Traditional Rental Income: $1850 Airbnb ROI: 4.35% Traditional ROI: 1.05%

Vacation Rentals in Chester

There are 56 vacation rental properties available for sale in the city of Chester . The median list price of Airbnb properties available for sale in Chester is $619,720 and the average price per square foot is $306. The cash on cash return on vacation rentals in Chester is 4.00%. The average monthly short term rental income in Chester is $4,662.

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

There are 56 Airbnb properties available for sale in Chester.

In 2026, the best neighborhood to buy short term rental property is CHESTER.

In January 2026, 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

1363 Calvert Rd

CHESTER, MD

3 beds | 2 baths | 1,400 sq.ft.

$469,999

Airbnb cash on cash: 9.66%

Traditional cash on cash: 3.09%

Airbnb Rental Income: $6279

Traditional Rental Income: $2152

Airbnb ROI: 9.66%

Traditional ROI: 3.09%

3000 Herons Nest Way #11

CHESTER, MD

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

$555,900

Airbnb cash on cash: 2.74%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $4662

Traditional Rental Income: $2646

Airbnb ROI: 2.74%

Traditional ROI: 0.71%

402 Blenny Ln

CHESTER, MD

3 beds | 3 baths | 1,747 sq.ft.

$399,000

Airbnb cash on cash: 9.71%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $6279

Traditional Rental Income: $3629

Airbnb ROI: 9.71%

Traditional ROI: 5.93%

1401 Calvert Rd

CHESTER, MD

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

$454,900

Airbnb cash on cash: 6.77%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $4662

Traditional Rental Income: $2336

Airbnb ROI: 6.77%

Traditional ROI: 3.57%

170 Harrier Way #34

CHESTER, MD

3 beds | 2 baths | 2,602 sq.ft.

$699,900

Airbnb cash on cash: 5.77%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $6279

Traditional Rental Income: $2981

Airbnb ROI: 5.77%

Traditional ROI: 2.61%

190 Harrier Way #11

CHESTER, MD

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

$540,000

Airbnb cash on cash: 3.92%

Traditional cash on cash: 1.26%

Airbnb Rental Income: $4662

Traditional Rental Income: $2354

Airbnb ROI: 3.92%

Traditional ROI: 1.26%

306 Teal Ct #C

CHESTER, MD

2 beds | 2 baths | 1,073 sq.ft.

$279,900

Airbnb cash on cash: 9.87%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $4662

Traditional Rental Income: $1858

Airbnb ROI: 9.87%

Traditional ROI: 2.9%

200 Harrier Way #21

CHESTER, MD

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

$674,900

Airbnb cash on cash: 4.99%

Traditional cash on cash: 1.56%

Airbnb Rental Income: $6279

Traditional Rental Income: $2881

Airbnb ROI: 4.99%