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.

Investment Property for Sale in Chester, MD

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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%
200 SCHOONER WAY CHESTER, MD Just minutes over the Chesapeake Bay Bridge, this beautifully maintained end-unit townhome...	3 beds \| 4 baths \| N/A	$550,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.75% Airbnb Rental Income: $2190 Traditional Rental Income: $3663 Airbnb ROI: -0.2% Traditional ROI: 3.75%
34-E QUEEN ANNE Way CHESTER, MD Open House Saturday April 4th 12:15- 1:30. Fully Remodeled Chester River Waterfront Condo!...	2 beds \| 3 baths \| 1,586 sq.ft.	$549,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 3.25% Airbnb Rental Income: $2028 Traditional Rental Income: $3067 Airbnb ROI: 0.2% Traditional ROI: 3.25%
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%
1025 DUNDEE Court CHESTER, MD Welcome home to this Amazingly priced townhome on Kent Island! Square foot pricing like th...	3 beds \| 3 baths \| 1,400 sq.ft.	$350,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 5.29% Airbnb Rental Income: $2190 Traditional Rental Income: $2606 Airbnb ROI: 2.34% Traditional ROI: 5.29%
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%
4000 HERONS NEST Way #22 CHESTER, MD Four Seasons @ Kent Island - 55+ Community - Turn-key & Lovely 2nd Floor Condo in Elevator...	2 beds \| 3 baths \| 1,900 sq.ft.	$560,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 2.21% Airbnb Rental Income: $2028 Traditional Rental Income: $3311 Airbnb ROI: -1.25% Traditional ROI: 2.21%
200 Harrier Way #21 CHESTER, MD The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2...	3 beds \| 2 baths \| 2,600 sq.ft.	$649,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 1.66% Airbnb Rental Income: $2190 Traditional Rental Income: $2881 Airbnb ROI: -0.4% Traditional ROI: 1.66%
1000 HERONS NEST WAY #23 CHESTER, MD Welcome to 1000 Herons Nest Way, where you can live the good life at an great price. This ...	2 beds \| 3 baths \| 2,003 sq.ft.	$494,900	Airbnb cash on cash: -1.42% Traditional cash on cash: 0.37% Airbnb Rental Income: $2028 Traditional Rental Income: $2331 Airbnb ROI: -1.42% Traditional ROI: 0.37%
134 MCHENNY Court CHESTER, MD Welcome home to this beautifully maintained three-bedroom, two-and-a-half-bath home in the...	3 beds \| 3 baths \| 1,839 sq.ft.	$615,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 2.51% Airbnb Rental Income: $2190 Traditional Rental Income: $2785 Airbnb ROI: 0.51% Traditional ROI: 2.51%
1868 ROBERTA Drive CHESTER, MD Price improvement! Motivated sellers. This custom built home offers the perfect opportunit...	5 beds \| 4 baths \| 3,250 sq.ft.	$744,500	Airbnb cash on cash: -1.27% Traditional cash on cash: 3.77% Airbnb Rental Income: $754 Traditional Rental Income: $3937 Airbnb ROI: -1.27% Traditional ROI: 3.77%
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%
111 MARSHGRASS WAY #22 CHESTER, MD Rare resale condo, turnkey! Your dream retreat awaits in this stunning luxury condo, where...	2 beds \| 3 baths \| N/A	$529,900	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.44% Airbnb Rental Income: $2028 Traditional Rental Income: $2761 Airbnb ROI: 0.89% Traditional ROI: 3.44%
807 Auckland Way CHESTER, MD Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier ...	3 beds \| 3 baths \| 2,100 sq.ft.	$425,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 4.76% Airbnb Rental Income: $2190 Traditional Rental Income: $3486 Airbnb ROI: 0.11% Traditional ROI: 4.76%
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%
1916 STEVENS Drive CHESTER, MD Now offered at a new and improved price, this beautifully updated and meticulously maintai...	3 beds \| 3 baths \| 1,728 sq.ft.	$475,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 4.61% Airbnb Rental Income: $2190 Traditional Rental Income: $2880 Airbnb ROI: 1.81% Traditional ROI: 4.61%
54-H QUEEN CAROLINE CT CHESTER, MD Owners have lowered the price by $10,000 and are willing to look at offers! Nothing to do ...	2 beds \| 3 baths \| N/A	$339,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 2.65% Airbnb Rental Income: $2028 Traditional Rental Income: $2064 Airbnb ROI: 0.88% Traditional ROI: 2.65%
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%
Chester Plan CHESTER, MD	2 beds \| 2 baths \| 1,900 sq.ft.	$504,990	Airbnb cash on cash: 0.9% Traditional cash on cash: 1.76% Airbnb Rental Income: $2028 Traditional Rental Income: $1908 Airbnb ROI: 0.9% Traditional ROI: 1.76%
Magothy Plan CHESTER, MD	2 beds \| 2 baths \| 2,003 sq.ft.	$504,990	Airbnb cash on cash: 0.9% Traditional cash on cash: 1.81% Airbnb Rental Income: $2028 Traditional Rental Income: $1931 Airbnb ROI: 0.9% Traditional ROI: 1.81%
Severn Plan CHESTER, MD	3 beds \| 2 baths \| 2,602 sq.ft.	$589,990	Airbnb cash on cash: 0.72% Traditional cash on cash: 1.66% Airbnb Rental Income: $2190 Traditional Rental Income: $2155 Airbnb ROI: 0.72% Traditional ROI: 1.66%
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%
Newtown Rd CHESTER, MD Newtown Rd, CHESTER, MD 21619 \| Other	N/A beds \| N/A baths \| N/A	$230,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 0.78% Airbnb Rental Income: $1134 Traditional Rental Income: $715 Airbnb ROI: 0.97% Traditional ROI: 0.78%
Parks Rd CHESTER, MD Parks Rd, CHESTER, MD 21619 \| Other	N/A beds \| N/A baths \| N/A	$275,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 0.32% Airbnb Rental Income: $1134 Traditional Rental Income: $715 Airbnb ROI: 0.48% Traditional ROI: 0.32%
110 Boatswain Way #3032 CHESTER, MD 110 Boatswain Way #3032, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$699,990	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.6% Airbnb Rental Income: $2028 Traditional Rental Income: $2555 Airbnb ROI: -1.02% Traditional ROI: 0.6%

Real Estate investment in Chester, MD

There are 83 properties for sale in the city of Chester . The median list price in Chester is $649,990 and the average price per square foot is $300. In May 2026, the average monthly cash on cash return in Chester is 2.00%. The average monthly rental income in Chester is $2,648.

Chester, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 83 investment properties available for sale in Chester.

In 2026, the best neighborhood to buy investment property is CHESTER.

The ROI for Short-Term is higher than the Long-Term in Chester with average rental income of $2,190.

Your search for investment property begins and ends here

Investment Property 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%

200 SCHOONER WAY

CHESTER, MD

3 beds | 4 baths | N/A

$550,000

Airbnb cash on cash: -0.2%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $2190

Traditional Rental Income: $3663

Airbnb ROI: -0.2%

Traditional ROI: 3.75%

34-E QUEEN ANNE Way

CHESTER, MD

2 beds | 3 baths | 1,586 sq.ft.

$549,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $2028

Traditional Rental Income: $3067

Airbnb ROI: 0.2%

Traditional ROI: 3.25%

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%

1025 DUNDEE Court

CHESTER, MD

3 beds | 3 baths | 1,400 sq.ft.

$350,000

Airbnb cash on cash: 2.34%

Traditional cash on cash: 5.29%

Airbnb Rental Income: $2190

Traditional Rental Income: $2606

Airbnb ROI: 2.34%

Traditional ROI: 5.29%

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%

4000 HERONS NEST Way #22

CHESTER, MD

2 beds | 3 baths | 1,900 sq.ft.

$560,000

Airbnb cash on cash: -1.25%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $2028

Traditional Rental Income: $3311

Airbnb ROI: -1.25%

Traditional ROI: 2.21%

200 Harrier Way #21

CHESTER, MD

3 beds | 2 baths | 2,600 sq.ft.

$649,900

Airbnb cash on cash: -0.4%

Traditional cash on cash: 1.66%

Airbnb Rental Income: $2190

Traditional Rental Income: $2881

Airbnb ROI: -0.4%