Houses for sale 2 bedroom in Chestertown

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

1 week + 22 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 + 22 hours ago

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

1 Bathroom

832 sq.ft

22 hours 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

22 hours 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

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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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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

15 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Kent County
USD 1,195,000
Chestertown, Kent County

2 Bedrooms

1 Bathroom

806 sq.ft

1 week + 5 days ago

35 pictures Arrow icon pointing to the right
Updated
House
House for sale in Chestertown, Kent County
USD 399,000
USD 455,000
12%
Chestertown, Kent County

2 Bedrooms

2 Bathrooms

1,904 sq.ft

GardenOffice roomFireplaceParking

22 hours ago

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House
House for sale in Calvert Heights, Chestertown
USD 85,000
Calvert Heights, Chestertown

2 Bedrooms

1 Bathroom

1,296 sq.ft

Aug 23, 2026

13 pictures Arrow icon pointing to the right
House
House for sale in Calvert Heights, Chestertown
USD 289,900
Calvert Heights, Chestertown

2 Bedrooms

3 Bathrooms

1,518 sq.ft

PatioGardenEquipped kitchen

Aug 17, 2026

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House
House for sale in Calvert Heights, Chestertown
USD 85,000
Calvert Heights, Chestertown

2 Bedrooms

1 Bathroom

1,296 sq.ft

Aug 04, 2026

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 + 22 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 + 22 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 + 22 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 + 22 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 + 22 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 659,999
Chestertown, Kent County

3 Bedrooms

2 Bathrooms

2,716 sq.ft

DeckFireplaceEquipped kitchen

1 week + 3 days ago

View photo Arrow icon pointing to the right
House
House for sale in Chestertown, Kent County
USD 289,000
Chestertown, Kent County

3 Bedrooms

2 Bathrooms

1,056 sq.ft

DeckEquipped kitchen

1 week + 5 days ago

66 pictures Arrow icon pointing to the right
House
House for sale in Heather Heights, Chestertown
USD 799,000
Heather Heights, Chestertown

3 Bedrooms

2 Bathrooms

2,857 sq.ft

GardenOffice roomFireplaceEquipped kitchen

2 weeks + 2 days ago

8 pictures Arrow icon pointing to the right
House
House for sale in The Grove, Chestertown
USD 568,900
The Grove, Chestertown

4 Bedrooms

2 Bathrooms

2,464 sq.ft

Equipped kitchenParking

2 weeks + 4 days ago

30 pictures Arrow icon pointing to the right
House
House for sale in Chester Harbor, Chestertown
USD 345,000
Chester Harbor, Chestertown

3 Bedrooms

1 Bathroom

1,398 sq.ft

GardenOffice roomEquipped kitchen

2 weeks + 6 days ago

28 pictures Arrow icon pointing to the right
Updated
House
House for sale in Washington Park, Chestertown
USD 295,000
USD 300,000
2%
Washington Park, Chestertown

3 Bedrooms

1 Bathroom

960 sq.ft

PatioEquipped kitchen

2 days + 22 hours ago

43 pictures Arrow icon pointing to the right
House
House for sale in Coventry Farms, Chestertown
USD 370,000
USD 375,000
1%
Coventry Farms, Chestertown

4 Bedrooms

2 Bathrooms

2,504 sq.ft

PatioParkingEquipped kitchenCellar

5 days + 22 hours ago

23 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Kent County
USD 315,000
Chestertown, Kent County

3 Bedrooms

1 Bathroom

1,008 sq.ft

ParkingDeckEquipped kitchen

1 week + 3 days ago

21 pictures Arrow icon pointing to the right
House
House for sale in Piney Grove, Chestertown
USD 229,000
Piney Grove, Chestertown

3 Bedrooms

1 Bathroom

936 sq.ft

Swimming poolParking

1 week + 5 days ago

Property value in Chestertown
Average price per sq.feet
USD 204/sq.feet
12.0 %
Price evolution on July 2026
19.0 %
Price evolution on August 2025
Average property value
USD 375,000

Property value in Chestertown by number of bedrooms

USD 244,500 USD 190/sq.feet
Average price of 2 bedrooms
USD 329,900 USD 235/sq.feet
Average price of 3 bedrooms
USD 475,000 USD 189/sq.feet
Average price of 4 bedrooms
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