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
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%
1012 Auckland Way CHESTER, MD Experience the best of Kent Island waterfront living in this beautifully appointed home lo...	3 beds \| 3 baths \| 2,076 sq.ft.	$599,900	Airbnb cash on cash: 1.42% Traditional cash on cash: 4.17% Airbnb Rental Income: $3321 Traditional Rental Income: $4122 Airbnb ROI: 1.42% Traditional ROI: 4.17%
34-E Queen Anne Way CHESTER, MD WATERFRONT Condo! Open House dates scheduled. Beautifully renovated 2BR/2.5BA waterfront c...	2 beds \| 2 baths \| 1,586 sq.ft.	$515,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 3.53% Airbnb Rental Income: $1989 Traditional Rental Income: $3067 Airbnb ROI: 0.21% Traditional ROI: 3.53%
115 Gibson Cir CHESTER, MD Nestled in the charming community of Gibsons Grant, this exquisite townhouse offers a luxu...	2 beds \| 2 baths \| 2,048 sq.ft.	$565,900	Airbnb cash on cash: 0.37% Traditional cash on cash: 2.39% Airbnb Rental Income: $1989 Traditional Rental Income: $2534 Airbnb ROI: 0.37% Traditional ROI: 2.39%
2008 Bridgepointe Dr CHESTER, MD Welcome to this gorgeous end unit townhouse offering low-maintenance living in a highly co...	2 beds \| 2 baths \| 1,804 sq.ft.	$355,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 5.39% Airbnb Rental Income: $1989 Traditional Rental Income: $2725 Airbnb ROI: 1.62% Traditional ROI: 5.39%
5011 Bridgepointe Dr CHESTER, MD Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome wit...	3 beds \| 2 baths \| 1,302 sq.ft.	$364,900	Airbnb cash on cash: 4.89% Traditional cash on cash: 4.79% Airbnb Rental Income: $3321 Traditional Rental Income: $2543 Airbnb ROI: 4.89% Traditional ROI: 4.79%
1025 Dundee Ct CHESTER, MD OPEN House Saturday July 11, 9:30-11:30am! Motivated Seller offering $5,000.00 in closing ...	3 beds \| 2 baths \| 1,400 sq.ft.	$298,000	Airbnb cash on cash: 6.14% Traditional cash on cash: 6.24% Airbnb Rental Income: $3321 Traditional Rental Income: $2606 Airbnb ROI: 6.14% Traditional ROI: 6.24%
3000 Herons Nest Way #11 CHESTER, MD A price improvement has been made, making this unit the best value in the entire community...	2 beds \| 2 baths \| 2,003 sq.ft.	$479,000	Airbnb cash on cash: -1.24% Traditional cash on cash: 1.39% Airbnb Rental Income: $1989 Traditional Rental Income: $2646 Airbnb ROI: -1.24% Traditional ROI: 1.39%
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%
4000 Herons Nest Way #22 CHESTER, MD Four Seasons @ Kent Island - 55+ Community - Price Improvement + Seller to Credit $4000 to...	2 beds \| 2 baths \| 1,900 sq.ft.	$515,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 2.37% Airbnb Rental Income: $1989 Traditional Rental Income: $3311 Airbnb ROI: -1.35% Traditional ROI: 2.37%
106 Bodys Neck Rd CHESTER, MD Welcome to Bayside, where coastal living and resort-style amenities come together in one o...	3 beds \| 2 baths \| 1,595 sq.ft.	$435,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 3.33% Airbnb Rental Income: $3321 Traditional Rental Income: $2829 Airbnb ROI: 2.71% Traditional ROI: 3.33%
124 Riverside Dr CHESTER, MD Gorgeous, like-new home on Kent Island! VA ASSUMABLE at 2.75% Interest!! Call for details!...	4 beds \| 2 baths \| 1,979 sq.ft.	$499,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 4.76% Airbnb Rental Income: $3463 Traditional Rental Income: $3150 Airbnb ROI: 3.79% Traditional ROI: 4.76%
190 Harrier Way #24 CHESTER, MD Built for low-maintenance living, this beautiful 3-bedroom, 2.5-bath condo offers 2,600 sq...	3 beds \| 2 baths \| 2,602 sq.ft.	$650,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 1.47% Airbnb Rental Income: $3321 Traditional Rental Income: $2881 Airbnb ROI: 0.97% Traditional ROI: 1.47%
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.	$639,900	Airbnb cash on cash: 1.13% Traditional cash on cash: 1.63% Airbnb Rental Income: $3321 Traditional Rental Income: $2881 Airbnb ROI: 1.13% Traditional ROI: 1.63%
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 \| 2 baths \| 2,003 sq.ft.	$490,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 0.37% Airbnb Rental Income: $1989 Traditional Rental Income: $2331 Airbnb ROI: -1.51% Traditional ROI: 0.37%
302 Merganser Ct #A CHESTER, MD FIRST FLOOR END UNIT IN BAYSIDE!! Kitchen w/Granite counters, breakfast bar, Laminate woo...	2 beds \| 2 baths \| 1,073 sq.ft.	$299,900	Airbnb cash on cash: 1.25% Traditional cash on cash: 2.63% Airbnb Rental Income: $1989 Traditional Rental Income: $1871 Airbnb ROI: 1.25% Traditional ROI: 2.63%
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%
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.	$425,500	Airbnb cash on cash: 2.47% Traditional cash on cash: 4.75% Airbnb Rental Income: $3321 Traditional Rental Income: $3486 Airbnb ROI: 2.47% Traditional ROI: 4.75%
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%
54-H Queen Caroline Ct CHESTER, MD DON""T MISS OUT on this super deal!! Owners have lowered the price by $10,000 and are will...	2 beds \| 2 baths \| 1,280 sq.ft.	$319,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 2.76% Airbnb Rental Income: $1989 Traditional Rental Income: $2064 Airbnb ROI: 0.83% Traditional ROI: 2.76%
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%
Chester Plan CHESTER, MD Chester Plan, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$544,990	Airbnb cash on cash: 0.83% Traditional cash on cash: 1.76% Airbnb Rental Income: $1989 Traditional Rental Income: $1908 Airbnb ROI: 0.83% Traditional ROI: 1.76%
Magothy Plan CHESTER, MD Magothy Plan, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$544,990	Airbnb cash on cash: 0.83% Traditional cash on cash: 1.81% Airbnb Rental Income: $1989 Traditional Rental Income: $1931 Airbnb ROI: 0.83% Traditional ROI: 1.81%
Severn Plan CHESTER, MD Severn Plan, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$629,990	Airbnb cash on cash: 2.43% Traditional cash on cash: 1.66% Airbnb Rental Income: $3321 Traditional Rental Income: $2155 Airbnb ROI: 2.43% Traditional ROI: 1.66%
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%

Real Estate investment in Chester, MD

There are 127 properties for sale in the city of Chester . The median list price in Chester is $442,235 and the average price per square foot is $196. In August 2026, the average monthly cash on cash return in Chester is 2.00%. The average monthly rental income in Chester is $2,686.

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

There are 127 investment properties available for sale in Chester.

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

The ROI for Long-Term is higher than the Short-Term in Chester with average rental income of $2,686.

Your search for investment property begins and ends here

Investment Property 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%

1012 Auckland Way

CHESTER, MD

3 beds | 3 baths | 2,076 sq.ft.

$599,900

Airbnb cash on cash: 1.42%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $3321

Traditional Rental Income: $4122

Airbnb ROI: 1.42%

Traditional ROI: 4.17%

34-E Queen Anne Way

CHESTER, MD

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

$515,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $1989

Traditional Rental Income: $3067

Airbnb ROI: 0.21%

Traditional ROI: 3.53%

115 Gibson Cir

CHESTER, MD

2 beds | 2 baths | 2,048 sq.ft.

$565,900

Airbnb cash on cash: 0.37%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $1989

Traditional Rental Income: $2534

Airbnb ROI: 0.37%

Traditional ROI: 2.39%

2008 Bridgepointe Dr

CHESTER, MD

2 beds | 2 baths | 1,804 sq.ft.

$355,000

Airbnb cash on cash: 1.62%

Traditional cash on cash: 5.39%

Airbnb Rental Income: $1989

Traditional Rental Income: $2725

Airbnb ROI: 1.62%

Traditional ROI: 5.39%

5011 Bridgepointe Dr

CHESTER, MD

3 beds | 2 baths | 1,302 sq.ft.

$364,900

Airbnb cash on cash: 4.89%

Traditional cash on cash: 4.79%

Airbnb Rental Income: $3321

Traditional Rental Income: $2543

Airbnb ROI: 4.89%

Traditional ROI: 4.79%

1025 Dundee Ct

CHESTER, MD

3 beds | 2 baths | 1,400 sq.ft.

$298,000

Airbnb cash on cash: 6.14%

Traditional cash on cash: 6.24%

Airbnb Rental Income: $3321

Traditional Rental Income: $2606

Airbnb ROI: 6.14%