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Detached houses for sale in Chestertown

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

1 day + 9 hours ago

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

6 days + 9 hours ago

30 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 365,000
Chestertown, Maryland
Equipped kitchen

1 week + 4 days ago

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

2 weeks + 4 days ago

View photo Arrow icon pointing to the right
Updated
Foreclosure
House
House for sale in Chestertown, Maryland
Request Details
Chestertown, Maryland

2 Bathrooms

1,804 sq.ft

1 day + 9 hours ago

View photo Arrow icon pointing to the right
Updated
Foreclosure
House
House for sale in Chestertown, Maryland
Request Details
Chestertown, Maryland

2 Bathrooms

1,664 sq.ft

1 day + 9 hours ago

50 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 3,000,000
Chestertown, Maryland
Fireplace

3 weeks + 9 hours ago

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

2 weeks + 9 hours ago

50 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 350,000
Chestertown, Maryland
PatioParking

2 weeks + 9 hours ago

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

2 weeks + 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

2 weeks + 9 hours ago

View photo Arrow icon pointing to the right
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

View photo Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 79,900
Chestertown, Maryland

1 Bathroom

Jan 02, 2026

View photo Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 15,000
Chestertown, Maryland

1 Bathroom

Jan 02, 2026

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

3 Bedrooms

1 Bathroom

PatioEquipped kitchen

2 days + 9 hours ago

90 pictures Arrow icon pointing to the right
New
House
House for sale in Chestertown, Maryland
USD 865,000
Chestertown, Maryland

3 Bedrooms

3 Bathrooms

2,472 sq.ft

Garden

2 days + 9 hours ago

View photo Arrow icon pointing to the right
New
Townhouse
Townhouse for sale in Chestertown, Maryland
USD 264,900
Chestertown, Maryland

3 Bedrooms

1 Bathroom

PatioEquipped kitchen

2 days + 9 hours 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

3 days + 9 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

1 week + 9 hours ago

View photo 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

2 weeks + 9 hours ago

10 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

2 weeks + 4 days ago

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

3 Bedrooms

1 Bathroom

1,000 sq.ft

Cellar

2 weeks + 5 days ago

49 pictures Arrow icon pointing to the right
Updated
House
House for sale in Chestertown, Maryland
USD 375,000
USD 385,000
3%
Chestertown, Maryland

5 Bedrooms

3 Bathrooms

2,534 sq.ft

Equipped kitchen

1 day + 9 hours ago

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

3 Bedrooms

2 Bathrooms

1,296 sq.ft

DeckEquipped kitchen

2 days + 9 hours ago

View photo Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 299,900
USD 349,900
14%
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,248 sq.ft

5 days + 9 hours 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

4 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 79,900
USD 89,900
11%
Chestertown, Maryland

3 Bedrooms

1 Bathroom

2,210 sq.ft

GardenEquipped kitchen

3 days + 9 hours ago

View photo Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 90,000
USD 120,000
25%
Chestertown, Maryland

2 Bedrooms

1 Bathroom

1,296 sq.ft

5 days + 9 hours ago

9 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 265,000
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,967 sq.ft

Parking

1 week + 4 days ago

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