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.

Townhouses for Sale in Chester, MD

Search for Townhouse for Sale in Chester, Maryland. Browse all of Mashvisor’s Townhouse listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 4 Townhouse 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
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%
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%
29-A Queen Mary Ct CHESTER, MD 29-A Queen Mary Ct, CHESTER, MD 21619 \| Townhouse	2 beds \| 2 baths \| 1,425 sq.ft.	$599,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 0.07% Airbnb Rental Income: $2028 Traditional Rental Income: $1859 Airbnb ROI: -0.57% Traditional ROI: 0.07%
54-F Queen Caroline Ct CHESTER, MD 54-F Queen Caroline Ct, CHESTER, MD 21619 \| Townhouse	3 beds \| 2 baths \| 1,440 sq.ft.	$375,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 1.67% Airbnb Rental Income: $2190 Traditional Rental Income: $2006 Airbnb ROI: 0.61% Traditional ROI: 1.67%
Other Investment Properties for Sale in Chester
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%
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%
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%

Your search for investment property begins and ends here

Townhouses for Sale in Chester, MD

134 MCHENNY Court

CHESTER, MD

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%

807 Auckland Way

CHESTER, MD

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%

29-A Queen Mary Ct

CHESTER, MD

2 beds | 2 baths | 1,425 sq.ft.

$599,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 0.07%

Airbnb Rental Income: $2028

Traditional Rental Income: $1859

Airbnb ROI: -0.57%

Traditional ROI: 0.07%

54-F Queen Caroline Ct

CHESTER, MD

3 beds | 2 baths | 1,440 sq.ft.

$375,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 1.67%

Airbnb Rental Income: $2190

Traditional Rental Income: $2006

Airbnb ROI: 0.61%

Traditional ROI: 1.67%

Other Investment Properties for Sale in Chester

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%

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%

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%

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%

CHESTER , MD

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