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170 Houses For Sale in Chestertown, MD

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New
house for sale
4 bds | 2 ba | 1,848 sqft

415 Pear Tree Point Rd, Chestertown, MD 21620

PEACE AND QUIET ABOUND AT THIS BEAUTIFUL CAPE COD. ACROSS THE STREET FROM THE CHESTER RIVER, CLOSE TO CHESTERTOWN, COUNT...
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$285,000
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New
house for sale
5 bds | 3 ba | 3,850 sqft

7824 Country Club Ln, Chestertown, MD 21620

Located in Country Club Estates, this home offers so much. There is a detached 2 car garage, an attached 2 car garage 4/...
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$536,000
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New
house for sale
3 bds | 2 ba | 1,800 sqft

8687 Poplar St, Chestertown, MD 21620

A must see charming renovation in a private setting! This fully updated home features 3 bedrooms, 2 full bathrooms, hard...
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$275,000
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house for sale
5 bds | 5 ba | 7,886 sqft

124 Goose Roost Ln, Chestertown, MD 21620

Seeking Space? Style & Seclusion? Welcome Home! Nearly 7900 sf of Custom Designed Space Total! With Over 5300 sf above g...
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$599,000
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house for sale
3 bds | 3 ba | 2,320 sqft

Chatham Executive Villa, Chestertown, MD 21620

This to-be-built home is the "Chatham Executive Villa" plan by Covell Communities, and is located in the community of Th...
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$479,900+
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house for sale
3 bds | 3 ba | 2,350 sqft

114 Landing Lane, Chestertown, MD 21620

This new construction, quick move-in home is the "Chatham Legacy Villa" plan by Covell Communities, and is located in th...
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$499,900
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house for sale
3 bds | 3 ba | -- sqft

136 Pearl Creek Ln, Chestertown, MD 21620

Modern Split Level home To Be Built. Pick your own colors and finishes. Stick built, quality construction. Cathedral cei...
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$259,900
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house for sale
3 bds | 3 ba | 2,350 sqft

Alexandria Classic, Chestertown, MD 21620

This to-be-built home is the "Alexandria Classic" plan by Covell Communities, and is located in the community of The Che...
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$599,900+
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house for sale
5 bds | 5 ba | 5,794 sqft

8221 Broad Neck Rd, Chestertown, MD 21620

Rare (for Kent County) and exceptionally exciting, ultra-contemporary residence is situated on a promontory above twenty...
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$1,275,000
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$7,500
house for sale
2 bds | 1 ba | 768 sqft

233 N Lynchburg St, Chestertown, MD 21620

Tired of renting? Looking for an investment property? This might be your solution. This two bedroom, one bath home is no...
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$87,500
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house for sale
3 bds | 3 ba | 3,001 sqft

129 Trafford Dr, Chestertown, MD 21620

Immaculate 3BR/2.5 colonial w/ over 3000 sqft of finished living space in desirable Coventry Farms! Located just outside...
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$319,900
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house for sale
3 bds | 3 ba | 2,350 sqft

214 Landing Lane, Chestertown, MD 21620

This new construction, quick move-in home is the "Alexandria Classic" plan by Covell Communities, and is located in the ...
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$614,900
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house for sale
4 bds | 3 ba | 2,240 sqft

8500 Broad Neck Rd, Chestertown, MD 21620

Custom Built 4 Bed 2.5 Bath Boasting 2240Sqft sitting on a 1 acre private wooded lot just a few miles from town or the b...
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$329,900
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house for sale
3 bds | 3 ba | 1,550 sqft

118 Landing Lane, Chestertown, MD 21620

This new construction, quick move-in home is the "Kiawah Legacy" plan by Covell Communities, and is located in the commu...
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$549,900
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house for sale
5 bds | 4 ba | 3,371 sqft

7915 Radcliffe Rd, Chestertown, MD 21620

This large, well maintained home was completely renovated in 2004 and additional changes in 2010. Great flowing floor pl...
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$550,000
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house for sale
3 bds | 3 ba | 2,394 sqft

Sawgrass Legacy, Chestertown, MD 21620

This to-be-built home is the "Sawgrass Legacy" plan by Covell Communities, and is located in the community of The Cheste...
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$559,900+
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house for sale
3 bds | 3 ba | 1,550 sqft

Kiawah Legacy, Chestertown, MD 21620

This to-be-built home is the "Kiawah Legacy" plan by Covell Communities, and is located in the community of The Chester ...
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$599,900+
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