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 19 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
1401 CALVERT Road 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%
203 RIVERSIDE DR CHESTER, MD To-be-built 5BR, 3.5BA waterfront home by Laine Street Homes - now under construction and ...	5 beds \| 4 baths \| N/A	$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%
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%
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%
109 John Gibson Dr CHESTER, MD 109 John Gibson Dr, CHESTER, MD 21619 \| Single Family Residential	6 beds \| 4 baths \| 4,165 sq.ft.	$915,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.09% Airbnb Rental Income: $null Traditional Rental Income: $3092 Airbnb ROI: N/A Traditional ROI: 1.09%
311 Kingfisher Ln CHESTER, MD 311 Kingfisher Ln, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$969,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.94% Airbnb Rental Income: $null Traditional Rental Income: $3115 Airbnb ROI: N/A Traditional ROI: 0.94%
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: -0.26% Airbnb Rental Income: $6279 Traditional Rental Income: $2760 Airbnb ROI: 1.5% Traditional ROI: -0.26%
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: 0.98% Airbnb Rental Income: $6279 Traditional Rental Income: $2760 Airbnb ROI: 3.99% Traditional ROI: 0.98%
Tuscaloosa Plan CHESTER, MD	5 beds \| 4 baths \| 3,225 sq.ft.	$847,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.71% Airbnb Rental Income: $null Traditional Rental Income: $3088 Airbnb ROI: N/A Traditional ROI: 1.71%
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: 2.27% Airbnb Rental Income: $4662 Traditional Rental Income: $2530 Airbnb ROI: 4.35% Traditional ROI: 2.27%
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: 1.25% Airbnb Rental Income: $6279 Traditional Rental Income: $2760 Airbnb ROI: 4.11% Traditional ROI: 1.25%
Simone Plan CHESTER, MD	4 beds \| 3 baths \| 2,791 sq.ft.	$700,990	Airbnb cash on cash: 4.88% Traditional cash on cash: 2.28% Airbnb Rental Income: $5802 Traditional Rental Income: $2944 Airbnb ROI: 4.88% Traditional ROI: 2.28%
Kelly Plan CHESTER, MD	2 beds \| 2 baths \| 2,143 sq.ft.	$773,990	Airbnb cash on cash: 2.91% Traditional cash on cash: 1.3% Airbnb Rental Income: $4662 Traditional Rental Income: $2530 Airbnb ROI: 2.91% Traditional ROI: 1.3%
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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chester, MD

1401 CALVERT Road

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%

203 RIVERSIDE DR

CHESTER, MD

5 beds | 4 baths | N/A

$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%

1704 BAYSIDE Drive

CHESTER, MD

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%

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%

Traditional ROI: 0.97%

109 John Gibson Dr

CHESTER, MD

6 beds | 4 baths | 4,165 sq.ft.

$915,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.09%

Airbnb Rental Income: $null

Traditional Rental Income: $3092

Airbnb ROI: N/A

Traditional ROI: 1.09%

311 Kingfisher Ln

CHESTER, MD

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

$969,990

Airbnb cash on cash: N/A

Traditional cash on cash: 0.94%

Airbnb Rental Income: $null

Traditional Rental Income: $3115

Airbnb ROI: N/A

Traditional ROI: 0.94%

1757 Harbor Dr

CHESTER, MD

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

3 beds | 3 baths | 2,930 sq.ft.

$1,400,000

Airbnb cash on cash: 1.5%

Traditional cash on cash: -0.26%

Airbnb Rental Income: $6279

Traditional Rental Income: $2760

Airbnb ROI: 1.5%