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 Single Family Residential For Sale in Chester, MD

Search for Single Family Residential for Sale in Chester, Maryland. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 25 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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%
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%
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%
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%
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%
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%
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: 1.5% 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%
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%
Taylor Plan CHESTER, MD	2 beds \| 2 baths \| 2,010 sq.ft.	$699,990	Airbnb cash on cash: 3.44% Traditional cash on cash: 0.63% Airbnb Rental Income: $4662 Traditional Rental Income: $1861 Airbnb ROI: 3.44% Traditional ROI: 0.63%
Munich ESP Plan CHESTER, MD	4 beds \| 3 baths \| 3,601 sq.ft.	$883,990	Airbnb cash on cash: 3.45% Traditional cash on cash: 0.85% Airbnb Rental Income: $5802 Traditional Rental Income: $2507 Airbnb ROI: 3.45% Traditional ROI: 0.85%
Franklin Plan CHESTER, MD	3 beds \| 3 baths \| 2,930 sq.ft.	$858,990	Airbnb cash on cash: 4.11% Traditional cash on cash: 0.95% Airbnb Rental Income: $6279 Traditional Rental Income: $2523 Airbnb ROI: 4.11% Traditional ROI: 0.95%
Jenkins II Plan CHESTER, MD	2 beds \| 2 baths \| 1,993 sq.ft.	$668,990	Airbnb cash on cash: 3.69% Traditional cash on cash: 0.75% Airbnb Rental Income: $4662 Traditional Rental Income: $1862 Airbnb ROI: 3.69% Traditional ROI: 0.75%
Simone Plan CHESTER, MD	4 beds \| 3 baths \| 2,791 sq.ft.	$700,990	Airbnb cash on cash: 4.88% Traditional cash on cash: 1.87% Airbnb Rental Income: $5802 Traditional Rental Income: $2679 Airbnb ROI: 4.88% Traditional ROI: 1.87%
Kelly Plan CHESTER, MD	2 beds \| 2 baths \| 2,143 sq.ft.	$773,990	Airbnb cash on cash: 2.91% Traditional cash on cash: 0.39% Airbnb Rental Income: $4662 Traditional Rental Income: $1879 Airbnb ROI: 2.91% Traditional ROI: 0.39%
Kerr Plan CHESTER, MD	3 beds \| 3 baths \| 2,789 sq.ft.	$818,990	Airbnb cash on cash: 4.41% Traditional cash on cash: 1.1% Airbnb Rental Income: $6279 Traditional Rental Income: $2523 Airbnb ROI: 4.41% Traditional ROI: 1.1%
Mykonos Plan CHESTER, MD	4 beds \| 3 baths \| 3,512 sq.ft.	$886,990	Airbnb cash on cash: 3.43% Traditional cash on cash: 0.84% Airbnb Rental Income: $5802 Traditional Rental Income: $2507 Airbnb ROI: 3.43% Traditional ROI: 0.84%
528 Warbler Way CHESTER, MD Come see this beauty before the snow!! Open House Saturday 1/25 10am. Like-new luxury livi...	4 beds \| 3 baths \| 2,791 sq.ft.	$799,500	Airbnb cash on cash: 4.48% Traditional cash on cash: 1.92% Airbnb Rental Income: $5802 Traditional Rental Income: $2738 Airbnb ROI: 4.48% Traditional ROI: 1.92%

Your search for investment property begins and ends here

Airbnb Single Family Residential 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%

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%

1906 Harbor Dr

CHESTER, MD

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%

Harbor Dr

CHESTER, MD

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

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

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

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%

259 Redstart Dr

CHESTER, MD

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%