Properties for sale in Chestertown

3,510,289 available properties
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New
Foreclosure
House
House for sale in Coventry Farms, Chestertown
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Coventry Farms, Chestertown

4 Bedrooms

2 Bathrooms

1,944 sq.ft

1 day + 4 hours ago

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Foreclosure
House
House for sale in Langford, Chestertown
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Langford, Chestertown

3 Bedrooms

3 Bathrooms

2,616 sq.ft

1 day + 4 hours ago

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Foreclosure
Farm
Farm for sale in Deep Landing, Chestertown
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Deep Landing, Chestertown

3 Bathrooms

2,812 sq.ft

1 day + 4 hours ago

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

2 Bathrooms

1,560 sq.ft

1 day + 4 hours ago

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House
House for sale in Chestertown, Kent County
USD 300,000
USD 325,000
8%
Chestertown, Kent County
GardenTerraceEquipped kitchen

1 week + 3 days ago

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

1 Bathroom

832 sq.ft

1 day + 4 hours ago

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

2 Bathrooms

1,664 sq.ft

1 day + 4 hours ago

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Apartment
Apartment for sale in Chestertown, Kent County
USD 685,000
Chestertown, Kent County
PatioTerraceParking

4 days + 4 hours ago

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House
House for sale in Chestertown, Kent County
USD 730,000
USD 750,000
3%
Chestertown, Kent County
GardenDeckEquipped kitchenParking

3 weeks + 4 hours ago

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House
House for sale in Chestertown, Kent County
USD 325,000
Chestertown, Kent County
Terrace

Oct 17, 2026

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Apartment
Apartment for sale in Chestertown, Kent County
USD 1,500,000
Chestertown, Kent County
PatioTerraceParking

Oct 16, 2026

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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

Oct 02, 2026

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

1 Bathroom

Oct 02, 2026

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

1 Bathroom

Oct 02, 2026

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

1 Bathroom

Oct 02, 2026

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New
Condo
Condo for sale in Coventry Farms, Chestertown
USD 375,000
Coventry Farms, Chestertown

4 Bedrooms

2 Bathrooms

2,886 sq.ft

FireplaceParkingCellar

2 days + 4 hours ago

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New
Condo
Condo for sale in Chestertown, Kent County
USD 685,000
Chestertown, Kent County

3 Bedrooms

3 Bathrooms

3,000 sq.ft

PatioParking

2 days + 4 hours ago

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Commercial
Commercial for sale in Mile Tree Village, Chestertown
USD 595,000
Mile Tree Village, Chestertown

7,296 sq.ft

4 days + 4 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

6 days + 4 hours ago

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Commercial
Commercial for sale in Calvert Heights, Chestertown
USD 3,300,000
Calvert Heights, Chestertown

25,911 sq.ft

Office roomSwimming poolLiftParking

2 days + 4 hours ago

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House
House for sale in Mile Tree Village, Chestertown
USD 229,900
Mile Tree Village, Chestertown

3 Bedrooms

2 Bathrooms

2,344 sq.ft

1 week + 4 hours ago

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

4 Bedrooms

2 Bathrooms

2,546 sq.ft

1 week + 4 hours ago

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House
House for sale in Coventry Farms, Chestertown
USD 499,999
Coventry Farms, Chestertown

4 Bedrooms

3 Bathrooms

3,506 sq.ft

DeckFireplaceEquipped kitchen

1 week + 4 hours ago

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Condo
Condo for sale in Chestertown, Kent County
USD 350,000
Chestertown, Kent County

1 Bedroom

1 Bathroom

850 sq.ft

PatioParking

1 week + 2 days ago

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Condo
Condo for sale in Chestertown, Kent County
USD 765,900
Chestertown, Kent County

3 Bedrooms

2 Bathrooms

1,964 sq.ft

FireplaceEquipped kitchenSwimming pool

1 week + 2 days ago

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Condo
Condo for sale in Chestertown, Kent County
USD 813,900
Chestertown, Kent County

3 Bedrooms

3 Bathrooms

2,192 sq.ft

Equipped kitchen

1 week + 2 days ago

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House
House for sale in Chestertown, Kent County
USD 799,900
Chestertown, Kent County

3 Bedrooms

3 Bathrooms

2,472 sq.ft

Garden

1 week + 3 days ago

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House
House for sale in Chestertown, Kent County
USD 1,125,000
Chestertown, Kent County

5 Bedrooms

3 Bathrooms

3,031 sq.ft

GardenFireplace

1 week + 3 days ago

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Townhouse
Townhouse for sale in Calvert Heights, Chestertown
USD 135,000
Calvert Heights, Chestertown

3 Bedrooms

1 Bathroom

1,136 sq.ft

1 week + 3 days ago

27 pictures Arrow icon pointing to the right
House
House for sale in Calvert Heights, Chestertown
USD 450,000
Calvert Heights, Chestertown

2 Bedrooms

2 Bathrooms

1,632 sq.ft

FireplaceEquipped kitchen

1 week + 3 days ago

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