Houses for sale in Chestertown

2,159,954 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 + 3 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 + 3 hours ago

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

1 week + 6 days ago

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

2 Bathrooms

2,104 sq.ft

1 day + 3 hours ago

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

1 week + 3 hours ago

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

1 week + 1 day 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 + 3 hours ago

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

2 Bathrooms

1,664 sq.ft

1 day + 3 hours ago

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

3 Bathrooms

2,812 sq.ft

1 day + 3 hours ago

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Apartment
Apartment for sale in Chestertown, Kent County
USD 350,000
Chestertown, Kent County
PatioTerraceParking

5 days + 3 hours ago

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

5 days + 3 hours ago

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Apartment
Apartment for sale in Chestertown, Kent County
USD 200,000
Chestertown, Kent County
PatioTerraceParking

5 days + 3 hours ago

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Apartment
Apartment for sale in Chestertown, Kent County
USD 375,000
Chestertown, Kent County
PatioTerraceParking

5 days + 3 hours ago

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

1 week + 1 day ago

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Property for sale in Chestertown, Kent County
USD 509,000
USD 550,000
7%
Chestertown, Kent County
Office roomFireplaceEquipped kitchenCellar

Sep 20, 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

3 weeks + 1 day ago

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

1 Bathroom

3 weeks + 1 day ago

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

1 Bathroom

3 weeks + 1 day ago

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

1 Bathroom

3 weeks + 1 day ago

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New
House
House for sale in Foxley Manor, Chestertown
USD 296,000
Foxley Manor, Chestertown

3 Bedrooms

1 Bathroom

1,248 sq.ft

GardenEquipped kitchenParking

2 days + 3 hours ago

66 pictures Arrow icon pointing to the right
House
House for sale in Coventry Farms, Chestertown
USD 425,000
Coventry Farms, Chestertown

4 Bedrooms

2 Bathrooms

3,165 sq.ft

Equipped kitchen

3 days + 3 hours ago

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House
House for sale in Chesapeake Landing, Chestertown
USD 238,000
Chesapeake Landing, Chestertown

3 Bedrooms

1 Bathroom

1,008 sq.ft

Equipped kitchen

5 days + 3 hours ago

49 pictures Arrow icon pointing to the right
House
House for sale in Langford Acres, Chestertown
USD 525,000
Langford Acres, Chestertown

3 Bedrooms

2 Bathrooms

1,833 sq.ft

6 days + 3 hours ago

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House
House for sale in Chestertown, Kent County
USD 238,000
Chestertown, Kent County

3 Bedrooms

1 Bathroom

1,008 sq.ft

Equipped kitchen

3 days + 3 hours ago

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House
House for sale in Foxley Manor, Chestertown
USD 296,000
Foxley Manor, Chestertown

3 Bedrooms

1 Bathroom

1,248 sq.ft

GardenEquipped kitchenParking

1 week + 4 days ago

25 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Kent County
USD 565,000
Chestertown, Kent County

2 Bedrooms

2 Bathrooms

1,306 sq.ft

Garden

1 week + 6 days ago

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House
House for sale in Chestertown, Kent County
USD 285,000
Chestertown, Kent County

4 Bedrooms

2 Bathrooms

1,400 sq.ft

Equipped kitchen

1 week + 6 days ago

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House
House for sale in Chestertown, Kent County
USD 679,900
Chestertown, Kent County

3 Bedrooms

3 Bathrooms

3,228 sq.ft

PatioGardenSwimming poolDeckCellar

1 week + 5 days ago

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House
House for sale in Chestertown, Kent County
USD 565,000
Chestertown, Kent County

2 Bedrooms

2 Bathrooms

4,306 sq.ft

Garden

2 weeks + 3 hours ago

62 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Kent County
USD 430,000
Chestertown, Kent County

3 Bedrooms

2 Bathrooms

1,520 sq.ft

FireplaceEquipped kitchen

2 weeks + 1 day ago

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Houses chestertown
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Property value in Chestertown
Average price per sq.feet
USD 244/sq.feet
19.3 %
Price evolution on August 2026
0.3 %
Price evolution on September 2025
Average property value
USD 372,000

Property value in Chestertown by number of bedrooms

USD 309,900 USD 210/sq.feet
Average price of 2 bedrooms Houses for sale with 2 bedrooms
USD 324,000 USD 246/sq.feet
Average price of 3 bedrooms Houses for sale with 3 bedrooms
USD 519,000 USD 199/sq.feet
Average price of 4 bedrooms Houses for sale with 4 bedrooms
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Houses chestertown
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