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 18 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: N/A Traditional cash on cash: 4.17% Airbnb Rental Income: $null Traditional Rental Income: $4122 Airbnb ROI: N/A Traditional ROI: 4.17%
108 Blenny Ln CHESTER, MD Open House Sunday, Aug 30 from 12-2PM - Bayside In Kent Island Located in the Popular Comm...	3 beds \| 2 baths \| 1,899 sq.ft.	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.39% Airbnb Rental Income: $null Traditional Rental Income: $2639 Airbnb ROI: N/A Traditional ROI: 3.39%
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.	$354,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.95% Airbnb Rental Income: $null Traditional Rental Income: $2543 Airbnb ROI: N/A Traditional ROI: 4.95%
53-E Queen Caroline Ct CHESTER, MD THIS IS A GREAT PRICE AT 209,900! This home features two master bedrooms each with their ...	2 beds \| 2 baths \| 1,440 sq.ft.	$329,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.71% Airbnb Rental Income: $null Traditional Rental Income: $2002 Airbnb ROI: N/A Traditional ROI: 2.71%
106 Bodys Neck Rd CHESTER, MD MARINA VIEWS FROM BOTH LEVELS! Discover a different side of Kent Island living at Bayside,...	3 beds \| 2 baths \| 1,595 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.38% Airbnb Rental Income: $null Traditional Rental Income: $2829 Airbnb ROI: N/A Traditional ROI: 3.38%
43-A Queen Neva Ct CHESTER, MD Queens Landing - Pristine Contemporary condo featuring 3 bedrooms 2 1/2 bath. This end u...	3 beds \| 2 baths \| 2,008 sq.ft.	$445,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.91% Airbnb Rental Income: $null Traditional Rental Income: $2171 Airbnb ROI: N/A Traditional ROI: 2.91%
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: N/A Traditional cash on cash: 4.75% Airbnb Rental Income: $null Traditional Rental Income: $3486 Airbnb ROI: N/A Traditional ROI: 4.75%
208 Blenny Ln CHESTER, MD NEW AMAZING PRICE!! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT ...	4 beds \| 2 baths \| 1,899 sq.ft.	$374,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.48% Airbnb Rental Income: $null Traditional Rental Income: $3322 Airbnb ROI: N/A Traditional ROI: 5.48%
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.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.29% Airbnb Rental Income: $null Traditional Rental Income: $2006 Airbnb ROI: N/A Traditional ROI: 2.29%
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.	$318,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.9% Airbnb Rental Income: $null Traditional Rental Income: $2329 Airbnb ROI: N/A Traditional ROI: 3.9%
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.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.93% Airbnb Rental Income: $null Traditional Rental Income: $2502 Airbnb ROI: N/A Traditional ROI: 4.93%
54-D Queen Caroline Ct CHESTER, MD 54-D Queen Caroline Ct, CHESTER, MD 21619 \| Townhouse	3 beds \| 2 baths \| 1,440 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $2018 Airbnb ROI: N/A Traditional ROI: 2.64%
41-D Queen Catherine Ct CHESTER, MD	3 beds \| 2 baths \| 1,750 sq.ft.	$439,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $3033 Airbnb ROI: N/A Traditional ROI: 3.35%
47-F Queen Anne Way CHESTER, MD	2 beds \| 2 baths \| 1,616 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.38% Airbnb Rental Income: $null Traditional Rental Income: $1953 Airbnb ROI: N/A Traditional ROI: 0.38%
12 Queen Anne Way #J CHESTER, MD 12 Queen Anne Way #J, CHESTER, MD 21619 \| Townhouse	1 beds \| 1 baths \| 1,260 sq.ft.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.78% Airbnb Rental Income: $null Traditional Rental Income: $1151 Airbnb ROI: N/A Traditional ROI: -0.78%
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: N/A Traditional cash on cash: 2.39% Airbnb Rental Income: $null Traditional Rental Income: $2534 Airbnb ROI: N/A Traditional ROI: 2.39%

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: N/A

Traditional cash on cash: 4.17%

Airbnb Rental Income: $null

Traditional Rental Income: $4122

Airbnb ROI: N/A

Traditional ROI: 4.17%

108 Blenny Ln

CHESTER, MD

3 beds | 2 baths | 1,899 sq.ft.

$369,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.39%

Airbnb Rental Income: $null

Traditional Rental Income: $2639

Airbnb ROI: N/A

Traditional ROI: 3.39%

5011 Bridgepointe Dr

CHESTER, MD

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

$354,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.95%

Airbnb Rental Income: $null

Traditional Rental Income: $2543

Airbnb ROI: N/A

Traditional ROI: 4.95%

53-E Queen Caroline Ct

CHESTER, MD

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

$329,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.71%

Airbnb Rental Income: $null

Traditional Rental Income: $2002

Airbnb ROI: N/A

Traditional ROI: 2.71%

106 Bodys Neck Rd

CHESTER, MD

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

$429,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.38%

Airbnb Rental Income: $null

Traditional Rental Income: $2829

Airbnb ROI: N/A

Traditional ROI: 3.38%

43-A Queen Neva Ct

CHESTER, MD

3 beds | 2 baths | 2,008 sq.ft.

$445,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.91%

Airbnb Rental Income: $null

Traditional Rental Income: $2171

Airbnb ROI: N/A

Traditional ROI: 2.91%

807 Auckland Way

CHESTER, MD

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

$425,500

Airbnb cash on cash: N/A

Traditional cash on cash: 4.75%

Airbnb Rental Income: $null

Traditional Rental Income: $3486

Airbnb ROI: N/A

Traditional ROI: 4.75%

208 Blenny Ln

CHESTER, MD

4 beds | 2 baths | 1,899 sq.ft.

$374,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.48%

Airbnb Rental Income: $null

Traditional Rental Income: $3322

Airbnb ROI: N/A