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
312 Blenny Ln CHESTER, MD You do not want to miss this opportunity to enjoy island living in this maintenance free, ...	3 beds \| 2 baths \| 1,899 sq.ft.	$479,000	Airbnb cash on cash: 7.96% Traditional cash on cash: 3.29% Airbnb Rental Income: $6279 Traditional Rental Income: $2950 Airbnb ROI: 7.96% Traditional ROI: 3.29%
3000 HERONS NEST Way unit: 11 CHESTER, MD A price improvement has been made with an additional seller paid $5,000.00 closing assista...	2 beds \| 3 baths \| 2,003 sq.ft.	$539,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 1.06% Airbnb Rental Income: $4662 Traditional Rental Income: $2646 Airbnb ROI: 3.08% Traditional ROI: 1.06%
402 BLENNY LN CHESTER, MD End-unit three-level townhome overlooking the pond in Bayside community. Freshly painted, ...	3 beds \| 4 baths \| N/A	$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%
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.	$669,900	Airbnb cash on cash: 5.04% Traditional cash on cash: 1.58% Airbnb Rental Income: $6279 Traditional Rental Income: $2881 Airbnb ROI: 5.04% Traditional ROI: 1.58%
1000 HERONS NEST WAY unit: 23 CHESTER, MD Welcome to 1000 Herons Nest Way, where you can live the good life at an great price. This ...	2 beds \| 3 baths \| 2,003 sq.ft.	$494,900	Airbnb cash on cash: 3.32% Traditional cash on cash: 0.37% Airbnb Rental Income: $4662 Traditional Rental Income: $2331 Airbnb ROI: 3.32% Traditional ROI: 0.37%
1000 HERONS NEST Way unit: 32 #32 CHESTER, MD Step into the good life in the sought-after Four Seasons on Kent Island, where low-mainten...	2 beds \| 2 baths \| N/A	$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%
4000 HERONS NEST Way unit: 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: 2.95% Traditional cash on cash: 1.76% Airbnb Rental Income: $4662 Traditional Rental Income: $3075 Airbnb ROI: 2.95% Traditional ROI: 1.76%
111 MARSHGRASS WAY #22 CHESTER, MD Rare resale condo, turnkey! Your dream retreat awaits in this stunning luxury condo, where...	2 beds \| 3 baths \| N/A	$539,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 1.75% Airbnb Rental Income: $4662 Traditional Rental Income: $2761 Airbnb ROI: 3.61% Traditional ROI: 1.75%
807 AUCKLAND Way CHESTER, MD Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier ...	3 beds \| 4 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.	$489,900	Airbnb cash on cash: 9.23% Traditional cash on cash: 3.65% Airbnb Rental Income: $6279 Traditional Rental Income: $2487 Airbnb ROI: 9.23% Traditional ROI: 3.65%
Harbor Dr CHESTER, MD New home being built! Act now and pick all your colors! Finished models can be seen! Call ...	N/A beds \| N/A baths \| 1,250 sq.ft.	$519,900	Airbnb cash on cash: 5.05% Traditional cash on cash: 3.76% Airbnb Rental Income: $4040 Traditional Rental Income: $2554 Airbnb ROI: 5.05% Traditional ROI: 3.76%
1916 STEVENS Drive CHESTER, MD OPEN HOUSE - Sat. March 28th- 12:00 - 2:00. Come see this beautifully updated 3-bedroom, 2...	3 beds \| 2 baths \| 1,728 sq.ft.	$489,000	Airbnb cash on cash: 9.18% Traditional cash on cash: 4.45% Airbnb Rental Income: $6279 Traditional Rental Income: $2880 Airbnb ROI: 9.18% Traditional ROI: 4.45%
1704 BAYSIDE Drive CHESTER, MD Discover a true waterfront treasure on .54 acres with 110 feet of waterfront. This beautif...	3 beds \| 3 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 \| 3 baths \| N/A	$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%
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%
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: 1.45% Traditional cash on cash: -0.41% Airbnb Rental Income: $6279 Traditional Rental Income: $2627 Airbnb ROI: 1.45% Traditional ROI: -0.41%
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: 1.72% Traditional cash on cash: -0.28% Airbnb Rental Income: $6279 Traditional Rental Income: $2627 Airbnb ROI: 1.72% Traditional ROI: -0.28%
135 Nauset Ln CHESTER, MD 135 Nauset Ln, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,795 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: 1.1% Traditional cash on cash: -0.44% Airbnb Rental Income: $4662 Traditional Rental Income: $2121 Airbnb ROI: 1.1% Traditional ROI: -0.44%
Bernstein II Plan CHESTER, MD Bernstein II Plan, CHESTER, MD 21619 \| Single Family Residential	2 beds \| 2 baths \| 1,690 sq.ft.	$636,990	Airbnb cash on cash: 3.76% Traditional cash on cash: 0.77% Airbnb Rental Income: $4662 Traditional Rental Income: $1850 Airbnb ROI: 3.76% Traditional ROI: 0.77%
Taylor Plan CHESTER, MD	2 beds \| 2 baths \| 2,010 sq.ft.	$752,990	Airbnb cash on cash: 2.89% Traditional cash on cash: 0.36% Airbnb Rental Income: $4662 Traditional Rental Income: $1861 Airbnb ROI: 2.89% Traditional ROI: 0.36%
Chester Plan CHESTER, MD	2 beds \| 2 baths \| 1,900 sq.ft.	$499,990	Airbnb cash on cash: 5.62% Traditional cash on cash: 1.8% Airbnb Rental Income: $4662 Traditional Rental Income: $1908 Airbnb ROI: 5.62% Traditional ROI: 1.8%
Magothy Plan CHESTER, MD	2 beds \| 2 baths \| 2,003 sq.ft.	$499,990	Airbnb cash on cash: 5.62% Traditional cash on cash: 1.85% Airbnb Rental Income: $4662 Traditional Rental Income: $1931 Airbnb ROI: 5.62% Traditional ROI: 1.85%
Severn Plan CHESTER, MD	3 beds \| 2 baths \| 2,602 sq.ft.	$584,990	Airbnb cash on cash: 6.98% Traditional cash on cash: 1.69% Airbnb Rental Income: $6279 Traditional Rental Income: $2155 Airbnb ROI: 6.98% Traditional ROI: 1.69%
Munich ESP Plan CHESTER, MD	4 beds \| 3 baths \| 3,601 sq.ft.	$883,990	Airbnb cash on cash: 3.3% Traditional cash on cash: 0.77% Airbnb Rental Income: $5802 Traditional Rental Income: $2507 Airbnb ROI: 3.3% Traditional ROI: 0.77%
Franklin Plan CHESTER, MD	3 beds \| 3 baths \| 2,930 sq.ft.	$858,990	Airbnb cash on cash: 3.93% Traditional cash on cash: 0.87% Airbnb Rental Income: $6279 Traditional Rental Income: $2523 Airbnb ROI: 3.93% Traditional ROI: 0.87%
Jenkins II Plan CHESTER, MD	2 beds \| 2 baths \| 1,993 sq.ft.	$669,990	Airbnb cash on cash: 3.49% Traditional cash on cash: 0.65% Airbnb Rental Income: $4662 Traditional Rental Income: $1862 Airbnb ROI: 3.49% Traditional ROI: 0.65%
Simone Plan CHESTER, MD	4 beds \| 3 baths \| 2,791 sq.ft.	$701,990	Airbnb cash on cash: 4.65% Traditional cash on cash: 1.74% Airbnb Rental Income: $5802 Traditional Rental Income: $2679 Airbnb ROI: 4.65% Traditional ROI: 1.74%
Kelly Plan CHESTER, MD	2 beds \| 2 baths \| 2,143 sq.ft.	$774,990	Airbnb cash on cash: 2.76% Traditional cash on cash: 0.32% Airbnb Rental Income: $4662 Traditional Rental Income: $1879 Airbnb ROI: 2.76% Traditional ROI: 0.32%
Kerr Plan CHESTER, MD	3 beds \| 3 baths \| 2,789 sq.ft.	$819,990	Airbnb cash on cash: 4.21% Traditional cash on cash: 1.01% Airbnb Rental Income: $6279 Traditional Rental Income: $2523 Airbnb ROI: 4.21% Traditional ROI: 1.01%
Mykonos Plan CHESTER, MD	4 beds \| 3 baths \| 3,512 sq.ft.	$886,990	Airbnb cash on cash: 3.28% Traditional cash on cash: 0.76% Airbnb Rental Income: $5802 Traditional Rental Income: $2507 Airbnb ROI: 3.28% Traditional ROI: 0.76%
Parks Rd CHESTER, MD Parks Rd, CHESTER, MD 21619 \| Other	N/A beds \| N/A baths \| N/A	$275,000	Airbnb cash on cash: 9.82% Traditional cash on cash: 0.32% Airbnb Rental Income: $4040 Traditional Rental Income: $715 Airbnb ROI: 9.82% Traditional ROI: 0.32%
6-G QUEEN VICTORIA Way CHESTER, MD Price Improvement!! Marina-front and perfectly sized for easy living or a weekend escape. ...	1 beds \| 1 baths \| 724 sq.ft.	$295,000	Airbnb cash on cash: 7.08% Traditional cash on cash: 3.15% Airbnb Rental Income: $3572 Traditional Rental Income: $1681 Airbnb ROI: 7.08% Traditional ROI: 3.15%
110 Boatswain Way #3021 CHESTER, MD 110 Boatswain Way #3021, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$749,990	Airbnb cash on cash: 3.68% Traditional cash on cash: 0.35% Airbnb Rental Income: $6279 Traditional Rental Income: $2592 Airbnb ROI: 3.68% Traditional ROI: 0.35%
110 Boatswain Way #3031 CHESTER, MD 110 Boatswain Way #3031, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$849,990	Airbnb cash on cash: 3.03% Traditional cash on cash: 0.07% Airbnb Rental Income: $6279 Traditional Rental Income: $2592 Airbnb ROI: 3.03% Traditional ROI: 0.07%
110 Boatswain Way #3032 CHESTER, MD 110 Boatswain Way #3032, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$699,990	Airbnb cash on cash: 2% Traditional cash on cash: 0.39% Airbnb Rental Income: $4662 Traditional Rental Income: $2555 Airbnb ROI: 2% Traditional ROI: 0.39%
110 Boatswain Way #3033 CHESTER, MD 110 Boatswain Way #3033, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$699,990	Airbnb cash on cash: 2% Traditional cash on cash: 0.39% Airbnb Rental Income: $4662 Traditional Rental Income: $2555 Airbnb ROI: 2% Traditional ROI: 0.39%
3-D QUEEN VICTORIA Court CHESTER, MD Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living roo...	1 beds \| 1 baths \| 724 sq.ft.	$275,000	Airbnb cash on cash: 7.86% Traditional cash on cash: 2.93% Airbnb Rental Income: $3572 Traditional Rental Income: $1511 Airbnb ROI: 7.86% Traditional ROI: 2.93%
110 Boatswain Way #21 CHESTER, MD 110 Boatswain Way #21, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$749,990	Airbnb cash on cash: 4.64% Traditional cash on cash: 1.54% Airbnb Rental Income: $6279 Traditional Rental Income: $2760 Airbnb ROI: 4.64% Traditional ROI: 1.54%

Vacation Rentals in Chester

There are 51 vacation rental properties available for sale in the city of Chester . The median list price of Airbnb properties available for sale in Chester is $665,445 and the average price per square foot is $321. 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 51 Airbnb properties available for sale in Chester.

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

In March 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

312 Blenny Ln

CHESTER, MD

3 beds | 2 baths | 1,899 sq.ft.

$479,000

Airbnb cash on cash: 7.96%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $6279

Traditional Rental Income: $2950

Airbnb ROI: 7.96%

Traditional ROI: 3.29%

3000 HERONS NEST Way unit: 11

CHESTER, MD

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

$539,000

Airbnb cash on cash: 3.08%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $4662

Traditional Rental Income: $2646

Airbnb ROI: 3.08%

Traditional ROI: 1.06%

402 BLENNY LN

CHESTER, MD

3 beds | 4 baths | N/A

$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%

200 Harrier Way #21

CHESTER, MD

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

$669,900

Airbnb cash on cash: 5.04%

Traditional cash on cash: 1.58%

Airbnb Rental Income: $6279

Traditional Rental Income: $2881

Airbnb ROI: 5.04%

Traditional ROI: 1.58%

1000 HERONS NEST WAY unit: 23

CHESTER, MD

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

$494,900

Airbnb cash on cash: 3.32%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $4662

Traditional Rental Income: $2331

Airbnb ROI: 3.32%

Traditional ROI: 0.37%

1000 HERONS NEST Way unit: 32 #32

CHESTER, MD

2 beds | 2 baths | N/A

$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%

4000 HERONS NEST Way unit: 22

CHESTER, MD

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

$560,000

Airbnb cash on cash: 2.95%

Traditional cash on cash: 1.76%

Airbnb Rental Income: $4662

Traditional Rental Income: $3075

Airbnb ROI: 2.95%

Traditional ROI: 1.76%

111 MARSHGRASS WAY #22

CHESTER, MD

2 beds | 3 baths | N/A

$539,000

Airbnb cash on cash: 3.61%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $4662

Traditional Rental Income: $2761

Airbnb ROI: 3.61%