Real Estate Investment Properties for Sale in Chester, MD

Looking for investment property in Chester, MD with high ROI ?

Explore a variety of short-term homes & houses in Chester, MD. Invest wisely with VRBO & Chester, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes 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 28 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
203 Riverside Dr CHESTER, MD To-be-built 5BR, 3.5BA waterfront home by Laine Street Homes - now under construction and ...	5 beds \| 3 baths \| 3,036 sq.ft.	$1,099,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.28% Airbnb Rental Income: $null Traditional Rental Income: $1588 Airbnb ROI: N/A Traditional ROI: 0.28%
1868 Roberta Dr CHESTER, MD This custom built home offers the perfect opportunity to live just minutes away from the C...	5 beds \| 3 baths \| 3,250 sq.ft.	$769,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.62% Airbnb Rental Income: $null Traditional Rental Income: $3937 Airbnb ROI: N/A Traditional ROI: 3.62%
205 Anchor Ln CHESTER, MD OPEN HOUSE, Saturday, 9/27, 11am -1pm...Price Improvement! Need more room? This expansive ...	6 beds \| 3 baths \| 3,500 sq.ft.	$535,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.14% Airbnb Rental Income: $null Traditional Rental Income: $4019 Airbnb ROI: N/A Traditional ROI: 6.14%
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 Dr CHESTER, MD OPEN HOUSE - Sun. March 15 12:00 - 2:00. Come see this beautifully updated 3-bedroom, 2 fu...	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 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%
311 Kingfisher Ln CHESTER, MD 311 Kingfisher Ln, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$939,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.97% Airbnb Rental Income: $null Traditional Rental Income: $3115 Airbnb ROI: N/A Traditional ROI: 0.97%
110 Kinglet Ct CHESTER, MD 110 Kinglet Ct, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$889,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.14% Airbnb Rental Income: $null Traditional Rental Income: $3115 Airbnb ROI: N/A Traditional ROI: 1.14%
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%
111 Flycatcher Way CHESTER, MD 111 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$1,400,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.03% Airbnb Rental Income: $null Traditional Rental Income: $3115 Airbnb ROI: N/A Traditional ROI: -0.03%
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%
Tuscaloosa Plan CHESTER, MD	5 beds \| 4 baths \| 3,225 sq.ft.	$873,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.6% Airbnb Rental Income: $null Traditional Rental Income: $3088 Airbnb ROI: N/A Traditional ROI: 1.6%
Bernstein II Plan CHESTER, MD Bernstein II Plan, CHESTER, MD 21619 \| Single Family Residential	2 beds \| 2 baths \| 1,690 sq.ft.	$661,990	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.	$777,990	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%
Munich ESP Plan CHESTER, MD	4 beds \| 3 baths \| 3,601 sq.ft.	$908,990	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.	$883,990	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.	$694,990	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.	$726,990	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.	$799,990	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.	$844,990	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.	$911,990	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%
2613 Cecil Dr CHESTER, MD 2613 Cecil Dr, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 3 baths \| 2,496 sq.ft.	$995,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.82% Airbnb Rental Income: $null Traditional Rental Income: $2786 Airbnb ROI: N/A Traditional ROI: 0.82%
1337 Queen Anne Dr CHESTER, MD Charming Renovated Ranch in Marling Farms This updated three-bedroom, two-and-a-half-bath ...	3 beds \| 2 baths \| 2,128 sq.ft.	$485,000	Airbnb cash on cash: 9.33% Traditional cash on cash: 4.51% Airbnb Rental Income: $6279 Traditional Rental Income: $2878 Airbnb ROI: 9.33% Traditional ROI: 4.51%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chester, MD

203 Riverside Dr

CHESTER, MD

5 beds | 3 baths | 3,036 sq.ft.

$1,099,900

Airbnb cash on cash: N/A

Traditional cash on cash: 0.28%

Airbnb Rental Income: $null

Traditional Rental Income: $1588

Airbnb ROI: N/A

Traditional ROI: 0.28%

1868 Roberta Dr

CHESTER, MD

5 beds | 3 baths | 3,250 sq.ft.

$769,500

Airbnb cash on cash: N/A

Traditional cash on cash: 3.62%

Airbnb Rental Income: $null

Traditional Rental Income: $3937

Airbnb ROI: N/A

Traditional ROI: 3.62%

205 Anchor Ln

CHESTER, MD

6 beds | 3 baths | 3,500 sq.ft.

$535,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.14%

Airbnb Rental Income: $null

Traditional Rental Income: $4019

Airbnb ROI: N/A

Traditional ROI: 6.14%

1906 Harbor Dr

CHESTER, MD

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

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 Dr

CHESTER, MD

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 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%

311 Kingfisher Ln

CHESTER, MD

5 beds | 4 baths | 3,225 sq.ft.

$939,990

Airbnb cash on cash: N/A

Traditional cash on cash: 0.97%

Airbnb Rental Income: $null

Traditional Rental Income: $3115

Airbnb ROI: N/A