Filters
TRANSACTION TYPE
HOUSE TYPE Apartments Apartment Condo Commercial Commercial Storage Space Detached homes Cottage Detached House House Ranch Land Farm Land Offices Office Rooms Room Semi-detached homes Duplex Townhouse
PRICE
BEDROOMS
BATHROOMS
AREA
AMENITIES Security Security Interior Equipped kitchen Fireplace Office room Air conditioning Cellar Heating Exterior Garden Patio Balcony Terrace Building features Parking Swimming pool Gym Deck Lift Sauna Access for people with disabilities Concierge
IndifferentFurnishedUnfurnishedPartly furnished
PROPERTY SITUATION Bank-Owned Property
IndifferentNear healthcare servicesNear public transportNear schoolsNear nursery schoolsNear beachesNear parks
IndifferentLast dayLast weekLast month

Apartments for sale in Chestertown

605,054 available properties
Sort by:
Most relevant first
Most relevant first
Most up-to-date first
Most recent published
Price: Lowest first
Price: Highest first
Bedrooms: Lowest first
Bedrooms: Highest first
Size: Lowest first
Size: Highest first
View photo Arrow icon pointing to the right
New
Foreclosure
House
House for sale in Chestertown, Maryland
Request Details
Chestertown, Maryland

4 Bedrooms

2 Bathrooms

1,944 sq.ft

18 hours ago

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

1 Bathroom

832 sq.ft

18 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

18 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

View photo Arrow icon pointing to the right
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

21 pictures Arrow icon pointing to the right
New
House
House for sale in Chestertown, Maryland
USD 229,000
Chestertown, Maryland

3 Bedrooms

1 Bathroom

936 sq.ft

Swimming poolParking

18 hours ago

2 pictures Arrow icon pointing to the right
New
Land
Land for sale in Chestertown, Maryland
USD 89,000
Chestertown, Maryland

18 hours ago

3 pictures Arrow icon pointing to the right
New
House
House for sale in Chestertown, Maryland
USD 300,000
Chestertown, Maryland

3 Bedrooms

1 Bathroom

960 sq.ft

PatioEquipped kitchen

18 hours ago

23 pictures Arrow icon pointing to the right
New
House
House for sale in Chestertown, Maryland
USD 315,000
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,008 sq.ft

ParkingDeckEquipped kitchen

18 hours ago

View photo Arrow icon pointing to the right
New
House
House for sale in Chestertown, Maryland
USD 229,000
Chestertown, Maryland

3 Bedrooms

1 Bathroom

936 sq.ft

Swimming poolParking

2 days + 18 hours ago

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

4 Bedrooms

2 Bathrooms

2,504 sq.ft

PatioParkingEquipped kitchenCellar

2 days + 18 hours ago

View photo Arrow icon pointing to the right
Land
Land for sale in Chestertown, Maryland
USD 350,000
Chestertown, Maryland

5 days + 18 hours ago

15 pictures Arrow icon pointing to the right
Land
Land for sale in Chestertown, Maryland
USD 1,195,000
Chestertown, Maryland

5 days + 18 hours ago

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

5 days + 18 hours ago

15 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 1,195,000
Chestertown, Maryland

2 Bedrooms

1 Bathroom

806 sq.ft

5 days + 18 hours ago

View photo Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 675,000
Chestertown, Maryland

5 Bedrooms

3 Bathrooms

2,838 sq.ft

GardenEquipped kitchenParking

6 days + 18 hours ago

View photo Arrow icon pointing to the right
Townhouse
Townhouse for sale in Chestertown, Maryland
USD 259,900
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,280 sq.ft

PatioEquipped kitchen

Jul 21, 2026

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

1 week + 18 hours ago

View photo Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 1,195,000
Chestertown, Maryland

2 Bedrooms

1 Bathroom

806 sq.ft

1 week + 1 day ago

41 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 524,900
Chestertown, Maryland

3 Bedrooms

2 Bathrooms

2,076 sq.ft

DeckFireplaceEquipped kitchen

1 week + 2 days ago

30 pictures Arrow icon pointing to the right
Updated
House
House for sale in Chestertown, Maryland
USD 304,000
Chestertown, Maryland

3 Bedrooms

2 Bathrooms

1,232 sq.ft

PatioGardenEquipped kitchen

18 hours ago

50 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 750,000
Chestertown, Maryland
GardenTerraceDeckEquipped kitchenParking

5 days + 18 hours ago

15 pictures Arrow icon pointing to the right
Townhouse
Townhouse for sale in Chestertown, Maryland
USD 259,900
Chestertown, Maryland

3 Bedrooms

2 Bathrooms

1,420 sq.ft

1 week + 3 days ago

59 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 649,000
Chestertown, Maryland

4 Bedrooms

3 Bathrooms

2,864 sq.ft

FireplaceEquipped kitchen

1 week + 5 days ago

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

1 week + 5 days ago

33 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 349,900
Chestertown, Maryland

3 Bedrooms

2 Bathrooms

1,650 sq.ft

GardenOffice roomEquipped kitchen

1 week + 1 day ago

7 pictures Arrow icon pointing to the right
Land
Land for sale in Chestertown, Maryland
USD 450,000
Chestertown, Maryland

1 week + 2 days ago

2 pictures Arrow icon pointing to the right
House
House for sale in Chestertown, Maryland
USD 299,900
Chestertown, Maryland

3 Bedrooms

1 Bathroom

1,056 sq.ft

GardenEquipped kitchen

2 weeks + 1 day ago

Enter your email and be the first to know about updates on:
Apartments chestertown
By suscribing you agree to the terms and conditions and privacy policy Receive alerts
Give us your email and we'll notify you as soon as we have news about:
Apartments chestertown
By suscribing you agree to the terms and conditions and privacy policy Receive alerts
Your search Apartments chestertown has been saved
Close