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Apartments for sale in Chestertown

601,516 available properties
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New
Foreclosure
House
House for sale in Chestertown, Maryland
Request Details
Chestertown, Maryland

2 Bathrooms

1,804 sq.ft

1 day + 9 hours ago

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New
Foreclosure
House
House for sale in Chestertown, Maryland
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Chestertown, Maryland

4 Bedrooms

2 Bathrooms

1,944 sq.ft

1 day + 9 hours ago

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Updated
Foreclosure
House
House for sale in Chestertown, Maryland
Request Details
Chestertown, Maryland

2 Bathrooms

1,664 sq.ft

1 day + 9 hours ago

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House
House for sale in Chestertown, Maryland
USD 360,000
Chestertown, Maryland

3 Bedrooms

2 Bathrooms

1,856 sq.ft

Equipped kitchen

Jan 02, 2026

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House
House for sale in Chestertown, Maryland
USD 40,000
Chestertown, Maryland

1 Bathroom

Jan 02, 2026

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House
House for sale in Chestertown, Maryland
USD 79,900
Chestertown, Maryland

1 Bathroom

Jan 02, 2026

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House
House for sale in Chestertown, Maryland
USD 15,000
Chestertown, Maryland

1 Bathroom

Jan 02, 2026

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

15,000 sq.ft

1 day + 9 hours ago

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New
Land
Land for sale in Chestertown, Maryland
USD 60,000
Chestertown, Maryland
Deck

1 day + 9 hours ago

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

15,000 sq.ft

1 day + 9 hours ago

18 pictures Arrow icon pointing to the right
New
Land
Land for sale in Chestertown, Maryland
USD 185,000
Chestertown, Maryland
Swimming pool

2 days + 9 hours ago

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New
House
House for sale in Chestertown, Maryland
USD 375,000
Chestertown, Maryland

4 Bedrooms

2 Bathrooms

1,476 sq.ft

GardenDeckEquipped kitchen

2 days + 9 hours ago

14 pictures Arrow icon pointing to the right
Land
Land for sale in Chestertown, Maryland
USD 25,000
Chestertown, Maryland

3 days + 9 hours ago

60 pictures Arrow icon pointing to the right
Commercial
Commercial for sale in Chestertown, Maryland
USD 650,000
Chestertown, Maryland

7,296 sq.ft

3 days + 9 hours ago

44 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 565,000
Chestertown, Maryland

3 Bedrooms

2 Bathrooms

2,927 sq.ft

Office roomFireplaceEquipped kitchenParking

3 days + 9 hours ago

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House
House for sale in Chestertown, Maryland
USD 375,000
Chestertown, Maryland

4 Bedrooms

2 Bathrooms

1,476 sq.ft

GardenDeckEquipped kitchen

3 days + 9 hours ago

5 pictures Arrow icon pointing to the right
Land
Land for sale in Chestertown, Maryland
Request Details
Chestertown, Maryland

15,000 sq.ft

3 days + 9 hours ago

2 pictures Arrow icon pointing to the right
Land
Land for sale in Chestertown, Maryland
USD 250,000
Chestertown, Maryland
Office room

1 week + 2 days ago

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Land
Land for sale in Chestertown, Maryland
Request Details
Chestertown, Maryland

15,000 sq.ft

3 days + 9 hours ago

9 pictures Arrow icon pointing to the right
Land
Land for sale in Chestertown, Maryland
USD 19,500
Chestertown, Maryland

4 days + 9 hours ago

50 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 1,600,000
Chestertown, Maryland
PatioParking

4 days + 9 hours ago

45 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 380,000
Chestertown, Maryland

3 Bedrooms

1 Bathroom

3,292 sq.ft

4 days + 9 hours ago

2 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 85,000
USD 90,000
6%
Chestertown, Maryland

2 Bedrooms

1 Bathroom

1,296 sq.ft

4 days + 9 hours ago

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House
House for sale in Chestertown, Maryland
USD 90,250
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,216 sq.ft

GardenEquipped kitchen

5 days + 9 hours ago

28 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 419,999
Chestertown, Maryland

4 Bedrooms

2 Bathrooms

1,656 sq.ft

GardenOffice roomEquipped kitchen

5 days + 9 hours ago

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Land
Land for sale in Chestertown, Maryland
USD 10,000
Chestertown, Maryland

15,000 sq.ft

5 days + 9 hours ago

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

5 days + 9 hours ago

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House
House for sale in Chestertown, Maryland
USD 380,000
Chestertown, Maryland

3 Bedrooms

1 Bathroom

3,292 sq.ft

5 days + 9 hours ago

69 pictures Arrow icon pointing to the right
Townhouse
Townhouse for sale in Chestertown, Maryland
USD 499,999
Chestertown, Maryland

2 Bedrooms

3 Bathrooms

2,100 sq.ft

DeckFireplaceEquipped kitchen

5 days + 9 hours ago

28 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 419,999
Chestertown, Maryland

4 Bedrooms

2 Bathrooms

1,656 sq.ft

GardenOffice roomEquipped kitchen

5 days + 9 hours ago

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