Detached houses for sale in Chestertown

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Updated
Property for sale in Mile Tree Village, Chestertown
Request Details
Mile Tree Village, Chestertown

23 hours ago

34 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Kent County
USD 325,000
Chestertown, Kent County

1 week + 23 hours ago

50 pictures Arrow icon pointing to the right
Apartment
Apartment for sale in Chestertown, Kent County
USD 350,000
Chestertown, Kent County
PatioParking

4 days + 23 hours ago

50 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Kent County
USD 750,000
Chestertown, Kent County
GardenDeckEquipped kitchenParking

5 days + 23 hours ago

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Foreclosure
House
House for sale in Chester Harbor, Chestertown
Request Details
Chester Harbor, Chestertown

1 Bathroom

832 sq.ft

23 hours ago

50 pictures Arrow icon pointing to the right
Apartment
Apartment for sale in Chestertown, Kent County
USD 1,500,000
Chestertown, Kent County
PatioParking

1 week + 1 day ago

50 pictures Arrow icon pointing to the right
Apartment
Apartment for sale in Chestertown, Kent County
USD 375,000
Chestertown, Kent County
PatioParking

1 week + 1 day ago

50 pictures Arrow icon pointing to the right
Property for sale in Chestertown, Kent County
USD 509,000
USD 550,000
7%
Chestertown, Kent County
Office roomFireplaceEquipped kitchenCellar

1 week + 3 days ago

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Updated
Foreclosure
House
House for sale in Chester Harbor, Chestertown
Request Details
Chester Harbor, Chestertown

2 Bathrooms

1,664 sq.ft

23 hours ago

50 pictures Arrow icon pointing to the right
Apartment
Apartment for sale in Chestertown, Kent County
USD 200,000
Chestertown, Kent County
PatioParking

4 days + 23 hours ago

50 pictures Arrow icon pointing to the right
Apartment
Apartment for sale in Chestertown, Kent County
USD 685,000
Chestertown, Kent County
PatioParking

1 week + 5 days ago

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House
House for sale in Chestertown, Kent County
USD 360,000
Chestertown, Kent County

3 Bedrooms

2 Bathrooms

1,856 sq.ft

Equipped kitchen

Jan 02, 2026

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House
House for sale in Chestertown, Kent County
USD 40,000
Chestertown, Kent County

1 Bathroom

Jan 02, 2026

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House
House for sale in Chestertown, Kent County
USD 79,900
Chestertown, Kent County

1 Bathroom

Jan 02, 2026

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House
House for sale in Chestertown, Kent County
USD 15,000
Chestertown, Kent County

1 Bathroom

Jan 02, 2026

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New
Land
Land for sale in Millbrook, Chestertown
Request Details
Millbrook, Chestertown

23 hours ago

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New
Commercial
Commercial for sale in Lees Corner, Chestertown
USD 250,000
Lees Corner, Chestertown

37,026 sq.ft

Office room

1 day + 23 hours ago

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Land
Land for sale in Calvert Heights, Chestertown
USD 350,000
Calvert Heights, Chestertown

3 days + 23 hours ago

93 pictures Arrow icon pointing to the right
House
House for sale in Heather Heights, Chestertown
USD 659,999
Heather Heights, Chestertown

3 Bedrooms

2 Bathrooms

2,716 sq.ft

DeckFireplaceEquipped kitchen

4 days + 23 hours ago

47 pictures Arrow icon pointing to the right
Condo
Condo for sale in Chestertown, Kent County
USD 475,000
Chestertown, Kent County

2 Bedrooms

2 Bathrooms

1,011 sq.ft

Fireplace

5 days + 23 hours ago

13 pictures Arrow icon pointing to the right
House
House for sale in Mile Tree Village, Chestertown
USD 495,000
Mile Tree Village, Chestertown

3 Bedrooms

2 Bathrooms

1,656 sq.ft

DeckParking

6 days + 23 hours ago

21 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Kent County
USD 200,000
Chestertown, Kent County

4 Bedrooms

1 Bathroom

1,816 sq.ft

4 days + 23 hours ago

4 pictures Arrow icon pointing to the right
Land
Land for sale in Sandy Bottom, Chestertown
USD 49,000
Sandy Bottom, Chestertown

1 week + 23 hours ago

33 pictures Arrow icon pointing to the right
House
House for sale in Mile Tree Village, Chestertown
USD 675,000
Mile Tree Village, Chestertown

5 Bedrooms

3 Bathrooms

2,838 sq.ft

GardenEquipped kitchenParking

1 week + 23 hours ago

32 pictures Arrow icon pointing to the right
House
House for sale in Lees Corner, Chestertown
USD 263,000
Lees Corner, Chestertown

3 Bedrooms

2 Bathrooms

1,140 sq.ft

1 week + 23 hours ago

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House
House for sale in Chestertown, Kent County
USD 2,895,000
Chestertown, Kent County

5 Bedrooms

3 Bathrooms

5,938 sq.ft

ParkingLift

1 week + 1 day ago

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House
House for sale in Chestertown, Kent County
USD 329,900
Chestertown, Kent County

2 Bedrooms

2 Bathrooms

1,440 sq.ft

1 week + 2 days ago

11 pictures Arrow icon pointing to the right
Land
Land for sale in Double Creek Wood, Chestertown
USD 60,000
Double Creek Wood, Chestertown
Deck

1 week + 2 days ago

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Land
Land for sale in Calvert Heights, Chestertown
USD 750,000
Calvert Heights, Chestertown

1 week + 3 days ago

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House
House for sale in Chestertown, Kent County
USD 659,999
Chestertown, Kent County

3 Bedrooms

2 Bathrooms

2,716 sq.ft

DeckFireplaceEquipped kitchen

1 week + 3 days ago

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