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Properties for sale in Chestertown

4,197,177 available properties
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Updated
Foreclosure
House
House for sale in Chestertown, Maryland
Request Details
Chestertown, Maryland

2 Bathrooms

1,804 sq.ft

1 day + 12 hours ago

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

2 Bathrooms

1,664 sq.ft

1 day + 12 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

72 pictures Arrow icon pointing to the right
New
House
House for sale in Chestertown, Maryland
USD 824,900
Chestertown, Maryland

5 Bedrooms

3 Bathrooms

4,353 sq.ft

Office roomFireplaceEquipped kitchen

1 day + 12 hours ago

50 pictures Arrow icon pointing to the right
New
House
House for sale in Chestertown, Maryland
USD 685,000
Chestertown, Maryland
PatioParking

1 day + 12 hours ago

50 pictures Arrow icon pointing to the right
New
House
House for sale in Chestertown, Maryland
USD 200,000
Chestertown, Maryland
PatioParking

1 day + 12 hours ago

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

5 days + 12 hours ago

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House
House for sale in Chestertown, Maryland
USD 325,000
Chestertown, Maryland

4 Bedrooms

2 Bathrooms

2,198 sq.ft

6 days + 12 hours ago

22 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 325,000
Chestertown, Maryland
Garden

1 week + 2 days ago

8 pictures Arrow icon pointing to the right
Townhouse
Townhouse for sale in Chestertown, Maryland
USD 264,900
Chestertown, Maryland

3 Bedrooms

1 Bathroom

PatioEquipped kitchen

1 week + 3 days ago

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Townhouse
Townhouse for sale in Chestertown, Maryland
USD 264,900
Chestertown, Maryland

3 Bedrooms

1 Bathroom

PatioEquipped kitchen

1 week + 3 days ago

18 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 344,000
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,216 sq.ft

Office roomEquipped kitchen

1 week + 4 days ago

50 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 550,000
Chestertown, Maryland
Office roomFireplaceEquipped kitchenCellar

2 weeks + 12 hours ago

7 pictures Arrow icon pointing to the right
Townhouse
Townhouse for sale in Chestertown, Maryland
USD 155,000
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,192 sq.ft

GardenParking

2 weeks + 1 day ago

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House
House for sale in Chestertown, Maryland
USD 344,000
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,216 sq.ft

3 weeks + 1 day ago

35 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 735,000
Chestertown, Maryland

4 Bedrooms

2 Bathrooms

2,730 sq.ft

GardenParking

Jun 28, 2026

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House
House for sale in Chestertown, Maryland
USD 325,000
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,000 sq.ft

Cellar

Jun 27, 2026

24 pictures Arrow icon pointing to the right
Townhouse
Townhouse for sale in Chestertown, Maryland
USD 275,000
USD 284,900
3%
Chestertown, Maryland

3 Bedrooms

2 Bathrooms

1,900 sq.ft

Office roomGymEquipped kitchenParking

3 days + 12 hours ago

49 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 375,000
Chestertown, Maryland

5 Bedrooms

3 Bathrooms

2,534 sq.ft

Equipped kitchen

1 week + 2 days ago

86 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 279,900
Chestertown, Maryland

3 Bedrooms

2 Bathrooms

1,296 sq.ft

DeckEquipped kitchen

1 week + 3 days ago

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House
House for sale in Chestertown, Maryland
USD 299,900
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,248 sq.ft

1 week + 6 days ago

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House
House for sale in Chestertown, Maryland
USD 90,000
Chestertown, Maryland

2 Bedrooms

1 Bathroom

1,296 sq.ft

1 week + 6 days ago

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House
House for sale in Chestertown, Maryland
USD 615,000
Chestertown, Maryland

4 Bedrooms

2 Bathrooms

4,536 sq.ft

Fireplace

Jun 16, 2026

37 pictures Arrow icon pointing to the right
Townhouse
Townhouse for sale in Chestertown, Maryland
USD 515,000
Chestertown, Maryland

2 Bedrooms

2 Bathrooms

1,476 sq.ft

GardenEquipped kitchenCellar

Jun 14, 2026

48 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 468,000
Chestertown, Maryland

3 Bedrooms

2 Bathrooms

3,262 sq.ft

Equipped kitchenParking

Jun 14, 2026

4 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 74,900
Chestertown, Maryland

3 Bedrooms

1 Bathroom

2,210 sq.ft

GardenEquipped kitchen

5 days + 12 hours ago

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House
House for sale in Chestertown, Maryland
USD 429,900
Chestertown, Maryland

4 Bedrooms

2 Bathrooms

2,160 sq.ft

DeckEquipped kitchenParking

5 days + 12 hours ago

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