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 52 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
114 Cedar Rd CHESTER, MD AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Discover your private sanctuary on this ...	3 beds \| 2 baths \| 3,128 sq.ft.	$375,000	Airbnb cash on cash: 5.05% Traditional cash on cash: 5.81% Airbnb Rental Income: $3321 Traditional Rental Income: $2849 Airbnb ROI: 5.05% Traditional ROI: 5.81%
2855 Cox Neck Rd CHESTER, MD Prestigious Southwind Water view * Elegant Open Floor Plan w/Masterful Architectural Deta...	4 beds \| 4 baths \| 4,413 sq.ft.	$1,195,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 0.96% Airbnb Rental Income: $3463 Traditional Rental Income: $3059 Airbnb ROI: 0.63% Traditional ROI: 0.96%
265 Evelyne St CHESTER, MD Coveted Gibson's Grant! This "Langley Model" is better than New...so why wait to build, wh...	3 beds \| 2 baths \| 2,119 sq.ft.	$620,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 2.24% Airbnb Rental Income: $3321 Traditional Rental Income: $2688 Airbnb ROI: 2.06% Traditional ROI: 2.24%
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.	$989,800	Airbnb cash on cash: 0.33% Traditional cash on cash: 0.42% Airbnb Rental Income: $2036 Traditional Rental Income: $1588 Airbnb ROI: 0.33% Traditional ROI: 0.42%
1868 Roberta Dr CHESTER, MD Price improvement! Motivated sellers. This custom built home offers the perfect opportunit...	5 beds \| 3 baths \| 3,250 sq.ft.	$724,500	Airbnb cash on cash: 0.31% Traditional cash on cash: 3.9% Airbnb Rental Income: $2036 Traditional Rental Income: $3937 Airbnb ROI: 0.31% Traditional ROI: 3.9%
1340 Queen Anne Dr 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: 4.46% Traditional cash on cash: 4.01% Airbnb Rental Income: $3321 Traditional Rental Income: $2393 Airbnb ROI: 4.46% Traditional ROI: 4.01%
205 Anchor Ln CHESTER, MD OPEN HOUSE, Saturday, 9/27, 11am -1pm...Price Improvement! Need more room? This expansive ...	5 beds \| 3 baths \| 3,000 sq.ft.	$535,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 6.14% Airbnb Rental Income: $2036 Traditional Rental Income: $4019 Airbnb ROI: 1.11% 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...	4 beds \| 2 baths \| 1,750 sq.ft.	$429,900	Airbnb cash on cash: 4.81% Traditional cash on cash: 4.29% Airbnb Rental Income: $3463 Traditional Rental Income: $2487 Airbnb ROI: 4.81% Traditional ROI: 4.29%
1916 Stevens Dr CHESTER, MD This beautifully updated and well maintained home delivers exceptional value in the highly...	3 beds \| 2 baths \| 1,728 sq.ft.	$470,000	Airbnb cash on cash: 3.98% Traditional cash on cash: 4.66% Airbnb Rental Income: $3321 Traditional Rental Income: $2880 Airbnb ROI: 3.98% Traditional ROI: 4.66%
1757 Harbor Dr CHESTER, MD 1757 Harbor Dr, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| N/A	$1,294,800	Airbnb cash on cash: 0.07% Traditional cash on cash: -0.06% Airbnb Rental Income: $3463 Traditional Rental Income: $2541 Airbnb ROI: 0.07% Traditional ROI: -0.06%
111 Flycatcher Way CHESTER, MD 111 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$1,200,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 0.31% Airbnb Rental Income: $2036 Traditional Rental Income: $3115 Airbnb ROI: -1.13% Traditional ROI: 0.31%
117 Flycatcher Way CHESTER, MD 117 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,930 sq.ft.	$1,200,000	Airbnb cash on cash: -0.17% Traditional cash on cash: -0.13% Airbnb Rental Income: $3321 Traditional Rental Income: $2627 Airbnb ROI: -0.17% Traditional ROI: -0.13%
123 Flycatcher Way CHESTER, MD 123 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,789 sq.ft.	$1,100,000	Airbnb cash on cash: -0.17% Traditional cash on cash: -0.13% Airbnb Rental Income: $3321 Traditional Rental Income: $2627 Airbnb ROI: -0.17% Traditional ROI: -0.13%
127 Flycatcher Way CHESTER, MD 127 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	2 beds \| 2 baths \| 1,993 sq.ft.	$900,000	Airbnb cash on cash: -0.86% Traditional cash on cash: -0.08% Airbnb Rental Income: $1989 Traditional Rental Income: $2121 Airbnb ROI: -0.86% Traditional ROI: -0.08%
Tuscaloosa Plan CHESTER, MD Tuscaloosa Plan, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$848,990	Airbnb cash on cash: -0.29% Traditional cash on cash: 1.7% Airbnb Rental Income: $2036 Traditional Rental Income: $3088 Airbnb ROI: -0.29% Traditional ROI: 1.7%
Taylor Plan CHESTER, MD Taylor Plan, CHESTER, MD 21619 \| Single Family Residential	2 beds \| 2 baths \| 2,010 sq.ft.	$699,990	Airbnb cash on cash: 0.02% Traditional cash on cash: 0.63% Airbnb Rental Income: $1989 Traditional Rental Income: $1861 Airbnb ROI: 0.02% Traditional ROI: 0.63%
Munich ESP Plan CHESTER, MD Munich ESP Plan, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 3,601 sq.ft.	$883,990	Airbnb cash on cash: 1.08% Traditional cash on cash: 0.85% Airbnb Rental Income: $3463 Traditional Rental Income: $2507 Airbnb ROI: 1.08% Traditional ROI: 0.85%
Franklin Plan CHESTER, MD Franklin Plan, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,930 sq.ft.	$858,990	Airbnb cash on cash: 1.02% Traditional cash on cash: 0.95% Airbnb Rental Income: $3321 Traditional Rental Income: $2523 Airbnb ROI: 1.02% Traditional ROI: 0.95%
Simone Plan CHESTER, MD Simone Plan, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 2,791 sq.ft.	$701,990	Airbnb cash on cash: 1.89% Traditional cash on cash: 1.87% Airbnb Rental Income: $3463 Traditional Rental Income: $2679 Airbnb ROI: 1.89% Traditional ROI: 1.87%
Kelly Plan CHESTER, MD Kelly Plan, CHESTER, MD 21619 \| Single Family Residential	2 beds \| 2 baths \| 2,143 sq.ft.	$709,990	Airbnb cash on cash: 0% Traditional cash on cash: 0.61% Airbnb Rental Income: $1989 Traditional Rental Income: $1879 Airbnb ROI: 0% Traditional ROI: 0.61%
Kerr Plan CHESTER, MD Kerr Plan, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,789 sq.ft.	$819,990	Airbnb cash on cash: 1.17% Traditional cash on cash: 1.1% Airbnb Rental Income: $3321 Traditional Rental Income: $2523 Airbnb ROI: 1.17% Traditional ROI: 1.1%
Mykonos Plan CHESTER, MD Mykonos Plan, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 3,512 sq.ft.	$886,990	Airbnb cash on cash: 1.07% Traditional cash on cash: 0.84% Airbnb Rental Income: $3463 Traditional Rental Income: $2507 Airbnb ROI: 1.07% Traditional ROI: 0.84%
719 Warbler Way CHESTER, MD 719 Warbler Way, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 2,791 sq.ft.	$829,990	Airbnb cash on cash: 0.83% Traditional cash on cash: 0.97% Airbnb Rental Income: $3463 Traditional Rental Income: $2805 Airbnb ROI: 0.83% Traditional ROI: 0.97%
215 Kingfisher Ln CHESTER, MD Price Reduced $50K - Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent...	5 beds \| 4 baths \| 3,225 sq.ft.	$1,049,500	Airbnb cash on cash: -0.59% Traditional cash on cash: 2.76% Airbnb Rental Income: $2036 Traditional Rental Income: $4779 Airbnb ROI: -0.59% Traditional ROI: 2.76%
126 Watermans Cove Ln CHESTER, MD Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman's Cove...	3 beds \| 3 baths \| 1,536 sq.ft.	$559,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 3.2% Airbnb Rental Income: $3321 Traditional Rental Income: $2748 Airbnb ROI: 2.87% Traditional ROI: 3.2%
233 Kingfisher Ln CHESTER, MD 233 Kingfisher Ln, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$999,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 0.86% Airbnb Rental Income: $2036 Traditional Rental Income: $3179 Airbnb ROI: -0.94% Traditional ROI: 0.86%
232 Evelyne St CHESTER, MD 232 Evelyne St, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 3,312 sq.ft.	$840,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 0.8% Airbnb Rental Income: $3463 Traditional Rental Income: $2661 Airbnb ROI: 0.84% Traditional ROI: 0.8%
330 Serenity Ln CHESTER, MD 330 Serenity Ln, CHESTER, MD 21619 \| Single Family Residential	7 beds \| 7 baths \| 10,667 sq.ft.	$5,400,000	Airbnb cash on cash: -1.85% Traditional cash on cash: -1.01% Airbnb Rental Income: $2036 Traditional Rental Income: $6113 Airbnb ROI: -1.85% Traditional ROI: -1.01%
540 Warbler Way CHESTER, MD 540 Warbler Way, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,789 sq.ft.	$929,990	Airbnb cash on cash: 0.38% Traditional cash on cash: 0.51% Airbnb Rental Income: $3321 Traditional Rental Income: $2689 Airbnb ROI: 0.38% Traditional ROI: 0.51%
134 Richard Ingle Way CHESTER, MD Nestled in the sought-after Gibson's Grant at Waters Edge community on Kent Island, this b...	4 beds \| 3 baths \| 2,185 sq.ft.	$749,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 2.42% Airbnb Rental Income: $3463 Traditional Rental Income: $3344 Airbnb ROI: 1.49% Traditional ROI: 2.42%
715 Warbler Way CHESTER, MD 715 Warbler Way, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 2,791 sq.ft.	$839,990	Airbnb cash on cash: 0.8% Traditional cash on cash: 1% Airbnb Rental Income: $3463 Traditional Rental Income: $2856 Airbnb ROI: 0.8% Traditional ROI: 1%
723 Warbler Way CHESTER, MD 723 Warbler Way, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 2,791 sq.ft.	$789,990	Airbnb cash on cash: 0.98% Traditional cash on cash: 1.19% Airbnb Rental Income: $3463 Traditional Rental Income: $2856 Airbnb ROI: 0.98% Traditional ROI: 1.19%
532 Warbler Way CHESTER, MD 532 Warbler Way, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,772 sq.ft.	$929,990	Airbnb cash on cash: 0.38% Traditional cash on cash: 0.54% Airbnb Rental Income: $3321 Traditional Rental Income: $2713 Airbnb ROI: 0.38% Traditional ROI: 0.54%
2513 Cecil Dr CHESTER, MD 2513 Cecil Dr, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 2 baths \| 2,700 sq.ft.	$1,350,000	Airbnb cash on cash: -0.96% Traditional cash on cash: -0.1% Airbnb Rental Income: $2036 Traditional Rental Income: $2579 Airbnb ROI: -0.96% Traditional ROI: -0.1%
205 Riverside Dr CHESTER, MD Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 12...	3 beds \| 2 baths \| 1,524 sq.ft.	$749,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 2.38% Airbnb Rental Income: $3321 Traditional Rental Income: $2788 Airbnb ROI: 2.08% Traditional ROI: 2.38%
118 Kinglet Ct CHESTER, MD 118 Kinglet Ct, CHESTER, MD 21619 \| Single Family Residential	2 beds \| 2 baths \| 2,010 sq.ft.	$969,990	Airbnb cash on cash: -0.56% Traditional cash on cash: 0.4% Airbnb Rental Income: $1989 Traditional Rental Income: $2338 Airbnb ROI: -0.56% Traditional ROI: 0.4%
114 Kinglet Ct CHESTER, MD 114 Kinglet Ct, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,772 sq.ft.	$1,009,990	Airbnb cash on cash: 0.56% Traditional cash on cash: 0.75% Airbnb Rental Income: $3321 Traditional Rental Income: $2754 Airbnb ROI: 0.56% Traditional ROI: 0.75%
233 Peregrine Dr CHESTER, MD Why wait for new construction when you can move right into this beautiful Simone model in ...	4 beds \| 3 baths \| 3,151 sq.ft.	$724,999	Airbnb cash on cash: 1.4% Traditional cash on cash: 2.27% Airbnb Rental Income: $3463 Traditional Rental Income: $3308 Airbnb ROI: 1.4% Traditional ROI: 2.27%
323 Kingfisher Ln CHESTER, MD 323 Kingfisher Ln, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$974,990	Airbnb cash on cash: -0.91% Traditional cash on cash: 0.98% Airbnb Rental Income: $2036 Traditional Rental Income: $3221 Airbnb ROI: -0.91% Traditional ROI: 0.98%
2882 Cox Neck Rd CHESTER, MD 2882 Cox Neck Rd, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 4,331 sq.ft.	$2,400,000	Airbnb cash on cash: -1% Traditional cash on cash: -0.99% Airbnb Rental Income: $3463 Traditional Rental Income: $2706 Airbnb ROI: -1% Traditional ROI: -0.99%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chester, MD

114 Cedar Rd

CHESTER, MD

3 beds | 2 baths | 3,128 sq.ft.

$375,000

Airbnb cash on cash: 5.05%

Traditional cash on cash: 5.81%

Airbnb Rental Income: $3321

Traditional Rental Income: $2849

Airbnb ROI: 5.05%

Traditional ROI: 5.81%

2855 Cox Neck Rd

CHESTER, MD

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

$1,195,000

Airbnb cash on cash: 0.63%

Traditional cash on cash: 0.96%

Airbnb Rental Income: $3463

Traditional Rental Income: $3059

Airbnb ROI: 0.63%

Traditional ROI: 0.96%

265 Evelyne St

CHESTER, MD

3 beds | 2 baths | 2,119 sq.ft.

$620,000

Airbnb cash on cash: 2.06%

Traditional cash on cash: 2.24%

Airbnb Rental Income: $3321

Traditional Rental Income: $2688

Airbnb ROI: 2.06%

Traditional ROI: 2.24%

203 Riverside Dr

CHESTER, MD

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

$989,800

Airbnb cash on cash: 0.33%

Traditional cash on cash: 0.42%

Airbnb Rental Income: $2036

Traditional Rental Income: $1588

Airbnb ROI: 0.33%

Traditional ROI: 0.42%

1868 Roberta Dr

CHESTER, MD

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

$724,500

Airbnb cash on cash: 0.31%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $2036

Traditional Rental Income: $3937

Airbnb ROI: 0.31%

Traditional ROI: 3.9%

1340 Queen Anne Dr

CHESTER, MD

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

$439,900

Airbnb cash on cash: 4.46%

Traditional cash on cash: 4.01%

Airbnb Rental Income: $3321

Traditional Rental Income: $2393

Airbnb ROI: 4.46%

Traditional ROI: 4.01%

205 Anchor Ln

CHESTER, MD

5 beds | 3 baths | 3,000 sq.ft.

$535,000

Airbnb cash on cash: 1.11%

Traditional cash on cash: 6.14%

Airbnb Rental Income: $2036

Traditional Rental Income: $4019

Airbnb ROI: 1.11%

Traditional ROI: 6.14%

1906 Harbor Dr

CHESTER, MD

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

$429,900

Airbnb cash on cash: 4.81%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $3463

Traditional Rental Income: $2487

Airbnb ROI: 4.81%