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 47 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...	4 beds \| 4 baths \| 4,413 sq.ft.	$1,125,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.08% Airbnb Rental Income: $null Traditional Rental Income: $3059 Airbnb ROI: N/A Traditional ROI: 1.08%
113 Bentons Pleasure Rd CHESTER, MD A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes...	4 beds \| 2 baths \| 3,168 sq.ft.	$868,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.79% Airbnb Rental Income: $null Traditional Rental Income: $3782 Airbnb ROI: N/A Traditional ROI: 2.79%
313 Thomas White Blvd CHESTER, MD Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's...	4 beds \| 2 baths \| 3,291 sq.ft.	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.48% Airbnb Rental Income: $null Traditional Rental Income: $2869 Airbnb ROI: N/A Traditional ROI: 1.48%
402 Macum Creek Dr CHESTER, MD GREAT NEW PRICE Shows like a MODEL in Gibson Grant! Located on a PREMIUM CORNER LOT, o...	3 beds \| 2 baths \| 2,787 sq.ft.	$789,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.24% Airbnb Rental Income: $null Traditional Rental Income: $2581 Airbnb ROI: N/A Traditional ROI: 1.24%
200 Church St CHESTER, MD	2 beds \| 2 baths \| 1,274 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.31% Airbnb Rental Income: $null Traditional Rental Income: $2007 Airbnb ROI: N/A Traditional ROI: 4.31%
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.	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.83% Airbnb Rental Income: $null Traditional Rental Income: $3937 Airbnb ROI: N/A Traditional ROI: 7.83%
148 Elinor St CHESTER, MD Discover your dream home in the exclusive WATER privileged community of Gibson's Grant, wh...	3 beds \| 2 baths \| 2,464 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.21% Airbnb Rental Income: $null Traditional Rental Income: $2726 Airbnb ROI: N/A Traditional ROI: 1.21%
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: N/A Traditional cash on cash: 4.01% Airbnb Rental Income: $null Traditional Rental Income: $2393 Airbnb ROI: N/A Traditional ROI: 4.01%
209 Harrier Way CHESTER, MD Welcome Home Open DAILY by Appointment If you're looking for the ease of primarily one-lev...	4 beds \| 3 baths \| 3,142 sq.ft.	$737,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.2% Airbnb Rental Income: $null Traditional Rental Income: $3143 Airbnb ROI: N/A Traditional ROI: 2.2%
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.	$515,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.41% Airbnb Rental Income: $null Traditional Rental Income: $4019 Airbnb ROI: N/A Traditional ROI: 6.41%
1757 Harbor Dr CHESTER, MD 1757 Harbor Dr, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| N/A	$1,198,800	Airbnb cash on cash: N/A Traditional cash on cash: 0.11% Airbnb Rental Income: $null Traditional Rental Income: $2541 Airbnb ROI: N/A Traditional ROI: 0.11%
117 Flycatcher Way CHESTER, MD The Franklin Model Home offers a beautifully designed open-concept layout enriched with el...	3 beds \| 3 baths \| 2,930 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.05% Airbnb Rental Income: $null Traditional Rental Income: $2627 Airbnb ROI: N/A Traditional ROI: 0.05%
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: N/A Traditional cash on cash: 1.7% Airbnb Rental Income: $null Traditional Rental Income: $3088 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.63% Airbnb Rental Income: $null Traditional Rental Income: $1861 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.85% Airbnb Rental Income: $null Traditional Rental Income: $2507 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.95% Airbnb Rental Income: $null Traditional Rental Income: $2523 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 1.87% Airbnb Rental Income: $null Traditional Rental Income: $2679 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.61% Airbnb Rental Income: $null Traditional Rental Income: $1879 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 1.1% Airbnb Rental Income: $null Traditional Rental Income: $2523 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.84% Airbnb Rental Income: $null Traditional Rental Income: $2507 Airbnb ROI: N/A Traditional ROI: 0.84%
215 Kingfisher Ln CHESTER, MD Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent Island Why wait to b...	5 beds \| 4 baths \| 3,225 sq.ft.	$995,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.96% Airbnb Rental Income: $null Traditional Rental Income: $4779 Airbnb ROI: N/A Traditional ROI: 2.96%
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: N/A Traditional cash on cash: 3.2% Airbnb Rental Income: $null Traditional Rental Income: $2748 Airbnb ROI: N/A Traditional ROI: 3.2%
232 Evelyne St CHESTER, MD 232 Evelyne St, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 3,312 sq.ft.	$825,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.85% Airbnb Rental Income: $null Traditional Rental Income: $2661 Airbnb ROI: N/A Traditional ROI: 0.85%
536 Warbler Way CHESTER, MD Welcome to the Taylor, a beautifully designed home offering 2 bedrooms, 2 baths, and a 3-c...	2 beds \| 2 baths \| 2,010 sq.ft.	$749,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.59% Airbnb Rental Income: $null Traditional Rental Income: $2314 Airbnb ROI: N/A Traditional ROI: 0.59%
540 Warbler Way CHESTER, MD Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car...	3 beds \| 3 baths \| 2,789 sq.ft.	$929,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.51% Airbnb Rental Income: $null Traditional Rental Income: $2689 Airbnb ROI: N/A Traditional ROI: 0.51%
134 Richard Ingle Way CHESTER, MD Experience the best of Kent Island living in this beautifully maintained coastal home, ide...	4 beds \| 3 baths \| 2,185 sq.ft.	$749,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.4% Airbnb Rental Income: $null Traditional Rental Income: $3344 Airbnb ROI: N/A Traditional ROI: 2.4%
532 Warbler Way CHESTER, MD Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car...	3 beds \| 3 baths \| 2,772 sq.ft.	$899,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.36% Airbnb Rental Income: $null Traditional Rental Income: $2713 Airbnb ROI: N/A Traditional ROI: 0.36%
2513 Cecil Dr CHESTER, MD 2513 Cecil Dr, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 2 baths \| 2,700 sq.ft.	$1,290,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.01% Airbnb Rental Income: $null Traditional Rental Income: $2579 Airbnb ROI: N/A Traditional ROI: -0.01%
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.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.62% Airbnb Rental Income: $null Traditional Rental Income: $2788 Airbnb ROI: N/A Traditional ROI: 2.62%
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: N/A Traditional cash on cash: 0.02% Airbnb Rental Income: $null Traditional Rental Income: $2338 Airbnb ROI: N/A Traditional ROI: 0.02%
114 Kinglet Ct CHESTER, MD 114 Kinglet Ct, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,772 sq.ft.	$999,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.78% Airbnb Rental Income: $null Traditional Rental Income: $2754 Airbnb ROI: N/A Traditional ROI: 0.78%
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: N/A Traditional cash on cash: 2.38% Airbnb Rental Income: $null Traditional Rental Income: $3308 Airbnb ROI: N/A Traditional ROI: 2.38%
300 Woods Point Rd CHESTER, MD 300 Woods Point Rd, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 2 baths \| 2,000 sq.ft.	$2,840,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.03% Airbnb Rental Income: $null Traditional Rental Income: $2858 Airbnb ROI: N/A Traditional ROI: -1.03%
121 Merlin Dr CHESTER, MD Experience the ease of elegant one-level living in this exceptional home, located in one o...	2 beds \| 2 baths \| 2,118 sq.ft.	$697,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.6% Airbnb Rental Income: $null Traditional Rental Income: $2676 Airbnb ROI: N/A Traditional ROI: 1.6%
315 Bentons Pleasure Rd CHESTER, MD This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty ...	3 beds \| 2 baths \| 1,688 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.1% Airbnb Rental Income: $null Traditional Rental Income: $2161 Airbnb ROI: N/A Traditional ROI: 2.1%
214 Bayberry Dr CHESTER, MD 214 Bayberry Dr, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,745 sq.ft.	$924,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.54% Airbnb Rental Income: $null Traditional Rental Income: $2700 Airbnb ROI: N/A Traditional ROI: 0.54%
118 Broadwater Dr CHESTER, MD Welcome to Resort-Style Living at Four Seasons at Kent Island! Why wait for new constructi...	2 beds \| 2 baths \| 2,473 sq.ft.	$656,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.6% Airbnb Rental Income: $null Traditional Rental Income: $2561 Airbnb ROI: N/A Traditional ROI: 1.6%
320 Bayberry Dr CHESTER, MD Be part of the fastest growing 55+ community on Marylands Eastern Shore. Bayberry was the ...	3 beds \| 2 baths \| 2,331 sq.ft.	$859,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.32% Airbnb Rental Income: $null Traditional Rental Income: $2806 Airbnb ROI: N/A Traditional ROI: 1.32%
1717 Harbor Dr CHESTER, MD 1717 Harbor Dr, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 2 baths \| 2,742 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.24% Airbnb Rental Income: $null Traditional Rental Income: $2235 Airbnb ROI: N/A Traditional ROI: -0.24%
326 Castle Marina Rd CHESTER, MD 326 Castle Marina Rd, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 3 baths \| 3,552 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.8% Airbnb Rental Income: $null Traditional Rental Income: $2981 Airbnb ROI: N/A Traditional ROI: 3.8%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chester, MD

2855 Cox Neck Rd

CHESTER, MD

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

$1,125,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.08%

Airbnb Rental Income: $null

Traditional Rental Income: $3059

Airbnb ROI: N/A

Traditional ROI: 1.08%

113 Bentons Pleasure Rd

CHESTER, MD

4 beds | 2 baths | 3,168 sq.ft.

$868,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.79%

Airbnb Rental Income: $null

Traditional Rental Income: $3782

Airbnb ROI: N/A

Traditional ROI: 2.79%

313 Thomas White Blvd

CHESTER, MD

4 beds | 2 baths | 3,291 sq.ft.

$799,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.48%

Airbnb Rental Income: $null

Traditional Rental Income: $2869

Airbnb ROI: N/A

Traditional ROI: 1.48%

402 Macum Creek Dr

CHESTER, MD

3 beds | 2 baths | 2,787 sq.ft.

$789,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.24%

Airbnb Rental Income: $null

Traditional Rental Income: $2581

Airbnb ROI: N/A

Traditional ROI: 1.24%

200 Church St

CHESTER, MD

2 beds | 2 baths | 1,274 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.31%

Airbnb Rental Income: $null

Traditional Rental Income: $2007

Airbnb ROI: N/A

Traditional ROI: 4.31%

1868 Roberta Dr

CHESTER, MD

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

$400,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.83%

Airbnb Rental Income: $null

Traditional Rental Income: $3937

Airbnb ROI: N/A

Traditional ROI: 7.83%

148 Elinor St

CHESTER, MD

3 beds | 2 baths | 2,464 sq.ft.

$899,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.21%

Airbnb Rental Income: $null

Traditional Rental Income: $2726

Airbnb ROI: N/A

Traditional ROI: 1.21%

1340 Queen Anne Dr

CHESTER, MD

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

$439,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.01%

Airbnb Rental Income: $null

Traditional Rental Income: $2393

Airbnb ROI: N/A