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 19 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
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: 1.4% Traditional cash on cash: 4.17% Airbnb Rental Income: $3314 Traditional Rental Income: $4122 Airbnb ROI: 1.4% Traditional ROI: 4.17%
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.	$569,900	Airbnb cash on cash: 0.82% Traditional cash on cash: 2.82% Airbnb Rental Income: $1989 Traditional Rental Income: $2534 Airbnb ROI: 0.82% Traditional ROI: 2.82%
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.	$375,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 5.05% Airbnb Rental Income: $1989 Traditional Rental Income: $2725 Airbnb ROI: 1.48% Traditional ROI: 5.05%
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: 4.87% Traditional cash on cash: 4.79% Airbnb Rental Income: $3314 Traditional Rental Income: $2543 Airbnb ROI: 4.87% 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.	$319,900	Airbnb cash on cash: 5.76% Traditional cash on cash: 5.87% Airbnb Rental Income: $3314 Traditional Rental Income: $2606 Airbnb ROI: 5.76% Traditional ROI: 5.87%
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: 2.7% Traditional cash on cash: 3.33% Airbnb Rental Income: $3314 Traditional Rental Income: $2829 Airbnb ROI: 2.7% Traditional ROI: 3.33%
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: 2.46% Traditional cash on cash: 4.75% Airbnb Rental Income: $3314 Traditional Rental Income: $3486 Airbnb ROI: 2.46% Traditional ROI: 4.75%
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.	$329,000	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%
3-D Queen Victoria Ct CHESTER, MD Price improvement and ready to move in! Welcome home to Queens Landing. One bedroom condo ...	1 beds \| 1 baths \| 724 sq.ft.	$249,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.33% Airbnb Rental Income: $1513 Traditional Rental Income: $1511 Airbnb ROI: 1.47% Traditional ROI: 3.33%
8-F Queen Victoria Way CHESTER, MD Queens Landing - One bedroom condo with living room overlooking kitchen, good for entertai...	1 beds \| 1 baths \| 724 sq.ft.	$240,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 2.61% Airbnb Rental Income: $1513 Traditional Rental Income: $1309 Airbnb ROI: 1.56% Traditional ROI: 2.61%
29-A Queen Mary Ct CHESTER, MD 29-A Queen Mary Ct, CHESTER, MD 21619 \| Townhouse	2 beds \| 2 baths \| 1,425 sq.ft.	$559,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 0.22% Airbnb Rental Income: $1989 Traditional Rental Income: $1859 Airbnb ROI: -0.53% Traditional ROI: 0.22%
208 Blenny Ln CHESTER, MD HUGE $20,000 PRICE REDUCTION!! Just like NEW! Welcome Home to this beautifully upgraded 4B...	3 beds \| 2 baths \| 1,899 sq.ft.	$414,900	Airbnb cash on cash: 2.94% Traditional cash on cash: 4.86% Airbnb Rental Income: $3314 Traditional Rental Income: $3322 Airbnb ROI: 2.94% Traditional ROI: 4.86%
54F Queen Caroline Ct CHESTER, MD Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters...	3 beds \| 2 baths \| 1,440 sq.ft.	$359,900	Airbnb cash on cash: 3.88% Traditional cash on cash: 2.2% Airbnb Rental Income: $3314 Traditional Rental Income: $2006 Airbnb ROI: 3.88% Traditional ROI: 2.2%
45-G Queen Neva Ct CHESTER, MD Seller is offering closing cost assistance for qualified buyers! This charming townhouse i...	2 beds \| 2 baths \| 1,312 sq.ft.	$349,500	Airbnb cash on cash: 0.85% Traditional cash on cash: 3.47% Airbnb Rental Income: $1989 Traditional Rental Income: $2329 Airbnb ROI: 0.85% Traditional ROI: 3.47%
6005 Bridgepointe Dr CHESTER, MD Low maintenance island living at its best! 6005 Bridgepointe Dr is freshly painted, deep c...	3 beds \| 2 baths \| 1,302 sq.ft.	$357,900	Airbnb cash on cash: 4.99% Traditional cash on cash: 4.78% Airbnb Rental Income: $3314 Traditional Rental Income: $2502 Airbnb ROI: 4.99% Traditional ROI: 4.78%
54-D Queen Caroline Ct CHESTER, MD 54-D Queen Caroline Ct, CHESTER, MD 21619 \| Townhouse	3 beds \| 2 baths \| 1,440 sq.ft.	$329,900	Airbnb cash on cash: 4% Traditional cash on cash: 2.21% Airbnb Rental Income: $3314 Traditional Rental Income: $2018 Airbnb ROI: 4% Traditional ROI: 2.21%
6010 Bridgepointe Dr CHESTER, MD CANCELLED OPEN HOUSE, Saturday July 11th , will be rescheduled.. Welcome to this beautiful...	3 beds \| 2 baths \| 1,885 sq.ft.	$387,500	Airbnb cash on cash: 4.39% Traditional cash on cash: 4.78% Airbnb Rental Income: $3314 Traditional Rental Income: $2712 Airbnb ROI: 4.39% Traditional ROI: 4.78%
7013 Bridgepointe Dr CHESTER, MD Adorable is the perfect word to describe this beautifully maintained townhome! Freshly pai...	3 beds \| 2 baths \| 1,635 sq.ft.	$375,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 5.57% Airbnb Rental Income: $3314 Traditional Rental Income: $2903 Airbnb ROI: 4.63% Traditional ROI: 5.57%

Your search for investment property begins and ends here

Townhouses for Sale in Chester, MD

1012 Auckland Way

CHESTER, MD

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

$599,900

Airbnb cash on cash: 1.4%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $3314

Traditional Rental Income: $4122

Airbnb ROI: 1.4%

Traditional ROI: 4.17%

115 Gibson Cir

CHESTER, MD

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

$569,900

Airbnb cash on cash: 0.82%

Traditional cash on cash: 2.82%

Airbnb Rental Income: $1989

Traditional Rental Income: $2534

Airbnb ROI: 0.82%

Traditional ROI: 2.82%

2008 Bridgepointe Dr

CHESTER, MD

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

$375,000

Airbnb cash on cash: 1.48%

Traditional cash on cash: 5.05%

Airbnb Rental Income: $1989

Traditional Rental Income: $2725

Airbnb ROI: 1.48%

Traditional ROI: 5.05%

5011 Bridgepointe Dr

CHESTER, MD

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

$364,900

Airbnb cash on cash: 4.87%

Traditional cash on cash: 4.79%

Airbnb Rental Income: $3314

Traditional Rental Income: $2543

Airbnb ROI: 4.87%

Traditional ROI: 4.79%

1025 Dundee Ct

CHESTER, MD

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

$319,900

Airbnb cash on cash: 5.76%

Traditional cash on cash: 5.87%

Airbnb Rental Income: $3314

Traditional Rental Income: $2606

Airbnb ROI: 5.76%

Traditional ROI: 5.87%

106 Bodys Neck Rd

CHESTER, MD

3 beds | 2 baths | 1,595 sq.ft.

$435,000

Airbnb cash on cash: 2.7%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $3314

Traditional Rental Income: $2829

Airbnb ROI: 2.7%

Traditional ROI: 3.33%

807 Auckland Way

CHESTER, MD

3 beds | 3 baths | 2,100 sq.ft.

$425,500

Airbnb cash on cash: 2.46%

Traditional cash on cash: 4.75%

Airbnb Rental Income: $3314

Traditional Rental Income: $3486

Airbnb ROI: 2.46%

Traditional ROI: 4.75%

54-H Queen Caroline Ct

CHESTER, MD

2 beds | 2 baths | 1,280 sq.ft.

$329,000

Airbnb cash on cash: 0.83%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $1989

Traditional Rental Income: $2064

Airbnb ROI: 0.83%