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 3 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
54F QUEEN CAROLINE CT CHESTER, MD Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters...	3 beds \| 3 baths \| N/A	$349,900	Airbnb cash on cash: 4.03% Traditional cash on cash: 2.29% Airbnb Rental Income: $3321 Traditional Rental Income: $2006 Airbnb ROI: 4.03% Traditional ROI: 2.29%
6005 BRIDGEPOINTE Drive CHESTER, MD Low maintenance island living at its best! 6005 Bridgepointe Dr is freshly painted, deep c...	3 beds \| 3 baths \| 1,302 sq.ft.	$349,000	Airbnb cash on cash: 5.16% Traditional cash on cash: 4.93% Airbnb Rental Income: $3321 Traditional Rental Income: $2502 Airbnb ROI: 5.16% Traditional ROI: 4.93%
115 GIBSON CIR CHESTER, MD Nestled in the charming community of Gibsons Grant, this exquisite townhouse offers a luxu...	2 beds \| 3 baths \| N/A	$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%
Other Investment Properties for Sale in Chester
1012 AUCKLAND Way CHESTER , MD Experience the best of Kent Island waterfront living in this beautifully appointed home lo...	3 beds \| 4 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%
108 BLENNY Lane CHESTER , MD Open House Sunday, Aug 30 from 12-2PM - Bayside In Kent Island Located in the Popular Comm...	3 beds \| 3 baths \| 1,899 sq.ft.	$389,900	Airbnb cash on cash: 4.25% Traditional cash on cash: 4.42% Airbnb Rental Income: $3321 Traditional Rental Income: $2639 Airbnb ROI: 4.25% Traditional ROI: 4.42%
34-E QUEEN ANNE Way CHESTER , MD WATERFRONT Condo! Open House dates scheduled. Beautifully renovated 2BR/2.5BA waterfront c...	2 beds \| 3 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%
5011 BRIDGEPOINTE Drive CHESTER , MD Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome wit...	3 beds \| 3 baths \| 1,302 sq.ft.	$354,900	Airbnb cash on cash: 5.05% Traditional cash on cash: 4.95% Airbnb Rental Income: $3321 Traditional Rental Income: $2543 Airbnb ROI: 5.05% Traditional ROI: 4.95%
3000 HERONS NEST Way #11 CHESTER , MD Love where you live! This highly sought-after first-floor condo is just steps from the wat...	2 beds \| 3 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%
113 BENTONS PLEASURE Road CHESTER , MD A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes...	4 beds \| 3 baths \| 3,168 sq.ft.	$868,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 2.79% Airbnb Rental Income: $3463 Traditional Rental Income: $3782 Airbnb ROI: 1.45% Traditional ROI: 2.79%
313 THOMAS WHITE Boulevard CHESTER , MD Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's...	4 beds \| 3 baths \| 3,291 sq.ft.	$825,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 2.1% Airbnb Rental Income: $3463 Traditional Rental Income: $3402 Airbnb ROI: 1.18% Traditional ROI: 2.1%
4000 HERONS NEST Way #22 CHESTER , MD Four Seasons @ Kent Island - 55+ Community - Reduced! * Turn-key & Lovely 2nd Floor Condo ...	2 beds \| 3 baths \| 1,900 sq.ft.	$499,000	Airbnb cash on cash: -1.37% Traditional cash on cash: 2.58% Airbnb Rental Income: $1989 Traditional Rental Income: $3311 Airbnb ROI: -1.37% Traditional ROI: 2.58%
106 BODYS NECK Road CHESTER , MD MARINA VIEWS FROM BOTH LEVELS! Discover a different side of Kent Island living at Bayside,...	3 beds \| 3 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%
203 RIVERSIDE DR CHESTER , MD ""Construction Complete, QUICK MOVE IN Coastal luxury living by Laine Street Homes, this e...	5 beds \| 4 baths \| N/A	$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%
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: 4.46% Traditional cash on cash: 4.01% Airbnb Rental Income: $3321 Traditional Rental Income: $2393 Airbnb ROI: 4.46% 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 \| N/A	$747,900	Airbnb cash on cash: 1.52% Traditional cash on cash: 2.16% Airbnb Rental Income: $3463 Traditional Rental Income: $3143 Airbnb ROI: 1.52% Traditional ROI: 2.16%
111 FLYCATCHER Way CHESTER , MD The Tuscaloosa Model Home offers an exceptional open-concept design enriched with high-end...	5 beds \| 5 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 The Franklin Model Home offers a beautifully designed open-concept layout enriched with el...	3 beds \| 4 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 The Kerr Model Home offers a beautifully crafted layout enhanced with elevated designer fi...	3 beds \| 3 baths \| 2,789 sq.ft.	$1,100,000	Airbnb cash on cash: 0% Traditional cash on cash: 0.05% Airbnb Rental Income: $3321 Traditional Rental Income: $2627 Airbnb ROI: 0% Traditional ROI: 0.05%

Your search for investment property begins and ends here

Townhouses for Sale in Chester, MD

54F QUEEN CAROLINE CT

CHESTER, MD

3 beds | 3 baths | N/A

$349,900

Airbnb cash on cash: 4.03%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $3321

Traditional Rental Income: $2006

Airbnb ROI: 4.03%

Traditional ROI: 2.29%

6005 BRIDGEPOINTE Drive

CHESTER, MD

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

$349,000

Airbnb cash on cash: 5.16%

Traditional cash on cash: 4.93%

Airbnb Rental Income: $3321

Traditional Rental Income: $2502

Airbnb ROI: 5.16%

Traditional ROI: 4.93%

115 GIBSON CIR

CHESTER, MD

2 beds | 3 baths | N/A

$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%

Other Investment Properties for Sale in Chester

CHESTER , MD

3 beds | 4 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%

CHESTER , MD

3 beds | 3 baths | 1,899 sq.ft.

$389,900

Airbnb cash on cash: 4.25%

Traditional cash on cash: 4.42%

Airbnb Rental Income: $3321

Traditional Rental Income: $2639

Airbnb ROI: 4.25%

Traditional ROI: 4.42%

CHESTER , MD

2 beds | 3 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%

CHESTER , MD

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

$354,900

Airbnb cash on cash: 5.05%

Traditional cash on cash: 4.95%

Airbnb Rental Income: $3321

Traditional Rental Income: $2543

Airbnb ROI: 5.05%

Traditional ROI: 4.95%

CHESTER , MD

2 beds | 3 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%

CHESTER , MD

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

$868,000