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Ranches for sale in Chestertown

228,213 available properties
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50 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 685,000
Chestertown, Maryland
PatioParking

4 days + 8 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 + 8 hours ago

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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 + 8 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 + 8 hours ago

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

1 week + 8 hours ago

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

Apr 18, 2026

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

Apr 17, 2026

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

Apr 17, 2026

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

Apr 06, 2026

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

Mar 03, 2026

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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

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

4 days + 8 hours ago

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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

5 days + 8 hours 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

3 days + 8 hours ago

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House
House for sale in Chestertown, Maryland
USD 349,900
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,248 sq.ft

1 week + 5 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

2 weeks + 2 days ago

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

5 Bedrooms

3 Bathrooms

2,534 sq.ft

Equipped kitchen

2 weeks + 2 days ago

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House
House for sale in Chestertown, Maryland
USD 439,900
Chestertown, Maryland

3 Bedrooms

Equipped kitchen

2 weeks + 3 days ago

View photo Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 212,000
Chestertown, Maryland

2 weeks + 3 days ago

View photo Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 492,000
Chestertown, Maryland
Equipped kitchen

2 weeks + 3 days ago

View photo Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 348,070
Chestertown, Maryland

849 sq.ft

PatioEquipped kitchen

2 weeks + 3 days ago

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

3 Bedrooms

2 Bathrooms

1,900 sq.ft

Office roomGymEquipped kitchenParking

3 days + 8 hours ago

4 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 99,900
USD 119,900
17%
Chestertown, Maryland

3 Bedrooms

1 Bathroom

2,210 sq.ft

GardenEquipped kitchen

5 days + 8 hours ago

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

2 weeks + 8 hours ago

12 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

2 weeks + 4 days ago

12 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

2 weeks + 4 days ago

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

2 Bedrooms

1 Bathroom

1,296 sq.ft

2 weeks + 5 days ago

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