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Ranches for sale in Chestertown

226,855 available properties
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2 pictures Arrow icon pointing to the right
Land
Land for sale in Chestertown, Maryland
Request Details
Chestertown, Maryland

1 week + 2 days ago

65 pictures Arrow icon pointing to the right
Commercial
Commercial for sale in Chestertown, Maryland
USD 1,350,000
USD 1,469,900
8%
Chestertown, Maryland

7,296 sq.ft

Equipped kitchen

1 week + 4 days ago

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

1 week + 4 days ago

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

15,000 sq.ft

1 week + 4 days ago

5 pictures Arrow icon pointing to the right
Condo
Condo for sale in Chestertown, Maryland
USD 685,000
Chestertown, Maryland

3 Bedrooms

3 Bathrooms

PatioParking

1 week + 4 days ago

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

1 week + 4 days ago

81 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 1,395,000
USD 1,495,000
7%
Chestertown, Maryland

4 Bedrooms

4 Bathrooms

3,383 sq.ft

Office roomParkingGymEquipped kitchenCellar

1 week + 4 days ago

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

1 week + 6 days ago

47 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 1,245,500
USD 1,295,500
4%
Chestertown, Maryland

5 Bedrooms

5 Bathrooms

3,243 sq.ft

2 weeks + 10 hours ago

26 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 198,000
USD 225,000
12%
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,200 sq.ft

GardenEquipped kitchenParking

2 weeks + 5 days ago

5 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 1,245,500
USD 1,295,500
4%
Chestertown, Maryland

5 Bedrooms

5 Bathrooms

2 weeks + 5 days ago

27 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 198,000
USD 225,000
12%
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,200 sq.ft

GardenEquipped kitchenParking

2 weeks + 6 days ago

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House
House for sale in Chestertown, Maryland
USD 224,900
USD 369,999
39%
Chestertown, Maryland

3 Bedrooms

2 Bathrooms

1,271 sq.ft

Parking

Jun 19, 2026

22 pictures Arrow icon pointing to the right
Condo
Condo for sale in Chestertown, Maryland
USD 839,500
Chestertown, Maryland

3 Bedrooms

3 Bathrooms

1,964 sq.ft

BalconyFireplaceEquipped kitchenSwimming pool

Jun 16, 2026

28 pictures Arrow icon pointing to the right
Condo
Condo for sale in Chestertown, Maryland
USD 1,800,000
Chestertown, Maryland

4 Bedrooms

4 Bathrooms

3,540 sq.ft

Equipped kitchenLift

Jun 15, 2026

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

15,000 sq.ft

Garden

Jun 14, 2026

12 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 340,000
USD 350,000
3%
Chestertown, Maryland

4 Bedrooms

2 Bathrooms

1,972 sq.ft

Jun 14, 2026

12 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 798,000
USD 828,000
4%
Chestertown, Maryland

3 Bedrooms

4 Bathrooms

3,047 sq.ft

Parking

Jun 14, 2026

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House
House for sale in Chestertown, Maryland
USD 385,000
USD 395,000
3%
Chestertown, Maryland

5 Bedrooms

3 Bathrooms

2,534 sq.ft

Equipped kitchen

Jun 12, 2026

22 pictures Arrow icon pointing to the right
Land
Land for sale in Chestertown, Maryland
USD 200,000
Chestertown, Maryland

Jun 10, 2026

23 pictures Arrow icon pointing to the right
Condo
Condo for sale in Chestertown, Maryland
USD 813,900
Chestertown, Maryland

3 Bedrooms

4 Bathrooms

2,192 sq.ft

BalconyEquipped kitchenSwimming poolLift

Jun 08, 2026

View photo Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 340,000
USD 350,000
3%
Chestertown, Maryland

4 Bedrooms

2 Bathrooms

1,972 sq.ft

Jun 08, 2026

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

5 Bedrooms

4 Bathrooms

3,932 sq.ft

PatioGardenEquipped kitchen

Jun 08, 2026

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

22,564 sq.ft

Garden

Jun 07, 2026

22 pictures Arrow icon pointing to the right
Condo
Condo for sale in Chestertown, Maryland
USD 849,900
Chestertown, Maryland

3 Bedrooms

3 Bathrooms

1,980 sq.ft

BalconyFireplaceEquipped kitchenSwimming pool

Jun 06, 2026

12 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 279,900
USD 434,999
36%
Chestertown, Maryland

4 Bedrooms

2 Bathrooms

7,200 sq.ft

GardenOffice roomEquipped kitchenParking

Jun 06, 2026

6 pictures Arrow icon pointing to the right
Land
Land for sale in Chestertown, Maryland
USD 225,000
Chestertown, Maryland

37,897 sq.ft

Office room

Jun 05, 2026

23 pictures Arrow icon pointing to the right
Condo
Condo for sale in Chestertown, Maryland
USD 765,900
Chestertown, Maryland

3 Bedrooms

3 Bathrooms

1,964 sq.ft

FireplaceEquipped kitchenSwimming pool

Jun 05, 2026

23 pictures Arrow icon pointing to the right
Condo
Condo for sale in Chestertown, Maryland
USD 799,900
Chestertown, Maryland

3 Bedrooms

4 Bathrooms

2,092 sq.ft

BalconyEquipped kitchenSwimming poolLift

Jun 05, 2026

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

37,026 sq.ft

Office room

Jun 05, 2026

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