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 29 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
2855 Cox Neck Rd CHESTER, MD Prestigious Southwind Water view * Elegant Open Floor Plan w/Masterful Architectural Deta...	3 beds \| 4 baths \| 4,413 sq.ft.	$1,250,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 0.87% Airbnb Rental Income: $2190 Traditional Rental Income: $3059 Airbnb ROI: -0.35% Traditional ROI: 0.87%
1906 STEVENS Drive CHESTER, MD Spacious and beautifully updated ranch-style home offering over 2,000 square feet of comfo...	3 beds \| 2 baths \| 2,016 sq.ft.	$464,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 4.12% Airbnb Rental Income: $2190 Traditional Rental Income: $2658 Airbnb ROI: 1.77% Traditional ROI: 4.12%
1838 SHERMAN Drive CHESTER, MD Nestled in the heart of Chester, Maryland on the beautiful Eastern Shore, this charming ra...	3 beds \| 2 baths \| 1,204 sq.ft.	$379,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 4.3% Airbnb Rental Income: $2190 Traditional Rental Income: $2270 Airbnb ROI: 2.52% Traditional ROI: 4.3%
1340 QUEEN ANNE Drive CHESTER, MD PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-priv...	3 beds \| 2 baths \| 1,248 sq.ft.	$439,900	Airbnb cash on cash: 2.18% Traditional cash on cash: 4.01% Airbnb Rental Income: $2190 Traditional Rental Income: $2393 Airbnb ROI: 2.18% Traditional ROI: 4.01%
1906 Harbor Dr CHESTER, MD Great opportunity for a savvy investor to buy way below market value. This 3 brm 2 ba ranc...	4 beds \| 2 baths \| 1,750 sq.ft.	$474,900	Airbnb cash on cash: 3.2% Traditional cash on cash: 3.79% Airbnb Rental Income: $2892 Traditional Rental Income: $2487 Airbnb ROI: 3.2% Traditional ROI: 3.79%
1872 HARBOR Drive CHESTER, MD Harbor View Community \| Corner Lot \| Renovated Rancher with Room to Grow If you've been se...	3 beds \| 2 baths \| 1,486 sq.ft.	$455,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 4.32% Airbnb Rental Income: $2190 Traditional Rental Income: $2614 Airbnb ROI: 2.02% Traditional ROI: 4.32%
200 Newtown Rd CHESTER, MD NO HOA! Beautifully maintained 2017-built home offering 3 bedrooms and 2.5 baths. Features...	3 beds \| 2 baths \| 1,296 sq.ft.	$445,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 4.23% Airbnb Rental Income: $2190 Traditional Rental Income: $2555 Airbnb ROI: 2.03% Traditional ROI: 4.23%
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: -2.09% Traditional cash on cash: 1.14% Airbnb Rental Income: $754 Traditional Rental Income: $3115 Airbnb ROI: -2.09% 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: -0.14% Traditional cash on cash: 0.16% Airbnb Rental Income: $2892 Traditional Rental Income: $2541 Airbnb ROI: -0.14% 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.	$1,300,000	Airbnb cash on cash: -2.09% Traditional cash on cash: 0.13% Airbnb Rental Income: $754 Traditional Rental Income: $3115 Airbnb ROI: -2.09% Traditional ROI: 0.13%
117 Flycatcher Way CHESTER, MD 117 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,930 sq.ft.	$1,300,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.28% Airbnb Rental Income: $2190 Traditional Rental Income: $2627 Airbnb ROI: -1.1% Traditional ROI: -0.28%
123 Flycatcher Way CHESTER, MD 123 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,789 sq.ft.	$1,200,000	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.13% Airbnb Rental Income: $2190 Traditional Rental Income: $2627 Airbnb ROI: -1.01% Traditional ROI: -0.13%
135 Nauset Ln CHESTER, MD 135 Nauset Ln, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,795 sq.ft.	$799,999	Airbnb cash on cash: -0.47% Traditional cash on cash: 0.81% Airbnb Rental Income: $2190 Traditional Rental Income: $2587 Airbnb ROI: -0.47% Traditional ROI: 0.81%
127 Flycatcher Way CHESTER, MD 127 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	2 beds \| 2 baths \| 1,993 sq.ft.	$1,000,000	Airbnb cash on cash: -0.95% Traditional cash on cash: -0.28% Airbnb Rental Income: $2028 Traditional Rental Income: $2121 Airbnb ROI: -0.95% Traditional ROI: -0.28%
Tuscaloosa Plan CHESTER, MD	5 beds \| 4 baths \| 3,225 sq.ft.	$848,990	Airbnb cash on cash: -1.64% Traditional cash on cash: 1.7% Airbnb Rental Income: $754 Traditional Rental Income: $3088 Airbnb ROI: -1.64% Traditional ROI: 1.7%
Taylor Plan CHESTER, MD	2 beds \| 2 baths \| 2,010 sq.ft.	$752,990	Airbnb cash on cash: -0.08% Traditional cash on cash: 0.44% Airbnb Rental Income: $2028 Traditional Rental Income: $1861 Airbnb ROI: -0.08% Traditional ROI: 0.44%
Munich ESP Plan CHESTER, MD	4 beds \| 3 baths \| 3,601 sq.ft.	$883,990	Airbnb cash on cash: 0.5% Traditional cash on cash: 0.85% Airbnb Rental Income: $2892 Traditional Rental Income: $2507 Airbnb ROI: 0.5% Traditional ROI: 0.85%
Franklin Plan CHESTER, MD	3 beds \| 3 baths \| 2,930 sq.ft.	$858,990	Airbnb cash on cash: -0.15% Traditional cash on cash: 0.95% Airbnb Rental Income: $2190 Traditional Rental Income: $2523 Airbnb ROI: -0.15% Traditional ROI: 0.95%
Simone Plan CHESTER, MD	4 beds \| 3 baths \| 2,791 sq.ft.	$701,990	Airbnb cash on cash: 1.17% Traditional cash on cash: 1.87% Airbnb Rental Income: $2892 Traditional Rental Income: $2679 Airbnb ROI: 1.17% Traditional ROI: 1.87%
Kelly Plan CHESTER, MD	2 beds \| 2 baths \| 2,143 sq.ft.	$774,990	Airbnb cash on cash: -0.13% Traditional cash on cash: 0.39% Airbnb Rental Income: $2028 Traditional Rental Income: $1879 Airbnb ROI: -0.13% Traditional ROI: 0.39%
Kerr Plan CHESTER, MD	3 beds \| 3 baths \| 2,789 sq.ft.	$819,990	Airbnb cash on cash: -0.06% Traditional cash on cash: 1.1% Airbnb Rental Income: $2190 Traditional Rental Income: $2523 Airbnb ROI: -0.06% Traditional ROI: 1.1%
Mykonos Plan CHESTER, MD	4 beds \| 3 baths \| 3,512 sq.ft.	$886,990	Airbnb cash on cash: 0.49% Traditional cash on cash: 0.84% Airbnb Rental Income: $2892 Traditional Rental Income: $2507 Airbnb ROI: 0.49% Traditional ROI: 0.84%
307 Kingfisher Ln CHESTER, MD 307 Kingfisher Ln, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,789 sq.ft.	$929,990	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.49% Airbnb Rental Income: $2190 Traditional Rental Income: $2669 Airbnb ROI: -0.71% Traditional ROI: 0.49%
132 Kestrel Ln CHESTER, MD 132 Kestrel Ln, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 3,634 sq.ft.	$945,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 0.45% Airbnb Rental Income: $2892 Traditional Rental Income: $2657 Airbnb ROI: -0.05% Traditional ROI: 0.45%
719 Warbler Way CHESTER, MD 719 Warbler Way, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 2,791 sq.ft.	$859,990	Airbnb cash on cash: 0.14% Traditional cash on cash: 0.87% Airbnb Rental Income: $2892 Traditional Rental Income: $2805 Airbnb ROI: 0.14% Traditional ROI: 0.87%
126 Claiborne St CHESTER, MD 126 Claiborne St, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 2 baths \| 2,276 sq.ft.	$787,900	Airbnb cash on cash: -0.41% Traditional cash on cash: 0.4% Airbnb Rental Income: $2190 Traditional Rental Income: $2234 Airbnb ROI: -0.41% Traditional ROI: 0.4%
1848 Harbor Dr CHESTER, MD 1848 Harbor Dr, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 2 baths \| 1,804 sq.ft.	$495,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 2.43% Airbnb Rental Income: $2190 Traditional Rental Income: $2187 Airbnb ROI: 1.24% Traditional ROI: 2.43%
233 Kingfisher Ln CHESTER, MD 233 Kingfisher Ln, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,353 sq.ft.	$1,045,000	Airbnb cash on cash: -2.09% Traditional cash on cash: 0.73% Airbnb Rental Income: $754 Traditional Rental Income: $3179 Airbnb ROI: -2.09% Traditional ROI: 0.73%
711 Warbler Way CHESTER, MD 711 Warbler Way, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 2,791 sq.ft.	$819,990	Airbnb cash on cash: 0.24% Traditional cash on cash: 1.04% Airbnb Rental Income: $2892 Traditional Rental Income: $2829 Airbnb ROI: 0.24% Traditional ROI: 1.04%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chester, MD

2855 Cox Neck Rd

CHESTER, MD

3 beds | 4 baths | 4,413 sq.ft.

$1,250,000

Airbnb cash on cash: -0.35%

Traditional cash on cash: 0.87%

Airbnb Rental Income: $2190

Traditional Rental Income: $3059

Airbnb ROI: -0.35%

Traditional ROI: 0.87%

1906 STEVENS Drive

CHESTER, MD

3 beds | 2 baths | 2,016 sq.ft.

$464,000

Airbnb cash on cash: 1.77%

Traditional cash on cash: 4.12%

Airbnb Rental Income: $2190

Traditional Rental Income: $2658

Airbnb ROI: 1.77%

Traditional ROI: 4.12%

1838 SHERMAN Drive

CHESTER, MD

3 beds | 2 baths | 1,204 sq.ft.

$379,000

Airbnb cash on cash: 2.52%

Traditional cash on cash: 4.3%

Airbnb Rental Income: $2190

Traditional Rental Income: $2270

Airbnb ROI: 2.52%

Traditional ROI: 4.3%

1340 QUEEN ANNE Drive

CHESTER, MD

3 beds | 2 baths | 1,248 sq.ft.

$439,900

Airbnb cash on cash: 2.18%

Traditional cash on cash: 4.01%

Airbnb Rental Income: $2190

Traditional Rental Income: $2393

Airbnb ROI: 2.18%

Traditional ROI: 4.01%

1906 Harbor Dr

CHESTER, MD

4 beds | 2 baths | 1,750 sq.ft.

$474,900

Airbnb cash on cash: 3.2%

Traditional cash on cash: 3.79%

Airbnb Rental Income: $2892

Traditional Rental Income: $2487

Airbnb ROI: 3.2%

Traditional ROI: 3.79%

1872 HARBOR Drive

CHESTER, MD

3 beds | 2 baths | 1,486 sq.ft.

$455,000

Airbnb cash on cash: 2.02%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $2190

Traditional Rental Income: $2614

Airbnb ROI: 2.02%

Traditional ROI: 4.32%

200 Newtown Rd

CHESTER, MD

3 beds | 2 baths | 1,296 sq.ft.

$445,000

Airbnb cash on cash: 2.03%

Traditional cash on cash: 4.23%

Airbnb Rental Income: $2190

Traditional Rental Income: $2555

Airbnb ROI: 2.03%

Traditional ROI: 4.23%

110 Kinglet Ct

CHESTER, MD

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

$889,990

Airbnb cash on cash: -2.09%

Traditional cash on cash: 1.14%

Airbnb Rental Income: $754

Traditional Rental Income: $3115

Airbnb ROI: -2.09%