105 High Street
Chestertown, MD 21620

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Description

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown's most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore's iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living—laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland's most beloved waterfront towns.

Features

• Property Type: Single Family Home
• Sub Type: Detached
• Listing Status: Active
• County/Area: Kent County
• Zip Code: 21620
• Year Built: 1863
• Subdivision/Neighborhood: Chestertown Historic District
• School District: Kent County Public Schools
• Sq.Ft.: 3,243 sq ft
• Style: Victorian
• Stories: 4 Story
• Total Rooms: 10
• Bedrooms: 5
• Full Baths: 4
• Half Baths: 1
• Basement: Improved, Interior Access, Yes
• Garage: 1 Car, Garage - Side Entry
• # of Parking Spaces: 1
• Fireplace: Yes, 2
• Lot Size: 2614 sq ft lot
• Baths: 5
• View: Water, Scenic Vista, River
• Zoning: R-3
• Above Grade Finished Area: 3243
• Above Grade Finished Area Source: Assessor
• Above Grade Finished Area Units: Square Feet
• Area Total: 4235
• Area Total Source: Assessor
• Below Grade Area Total: 992
• Below Grade Area Total Source: Assessor
• Below Grade Finished Area Source: Assessor
• Below Grade Finished Area Units: Square Feet
• Below Grade Unfinished Area: 992
• Below Grade Unfinished Area Source: Assessor
• Below Grade Unfinished Area Units: Square Feet
• Central Air: Yes
• City Town Tax: 5588
• City Town Tax Payment Frequency: Annually
• Construction Materials: Frame
• Cooling: Central A/C
• Cooling Fuel: Electric
• Country: US
• Cross Street: Water Street
• Directions: From Chestertown's waterfront at the end of High Street, walk past the Customs House (one of the original British Ports of Entry) then it will be the next house on your left.
• Distance To Body Of Water: 1
• Distance To Body Of Water Units: Blocks
• Foundation Details: Permanent
• Heating: Heat Pump(s)
• Heating Fuel: Electric, Propane - Leased
• Hot Water: Propane
• In City Limits: Yes
• List: Bedroom 2, Bedroom 3, Bedroom 1, Bathroom 1, Bathroom 2, Half Bath
• Listing Locale: 200004363592
• Living Area Source: Assessor
• Location Type: Downtown
• Lot Size Source: Assessor
• Lot Size Square Feet: 2688
• Lot Size Units: Square Feet
• Main Level Full Baths: 1
• Main Level Half Baths: 1
• Main Level Total Baths: 2
• Main Type: Residential
• Num Detached Garage Spaces: 1
• Other Structures: Above Grade, Below Grade
• Other Structures List: Garages
• Ownership Interest: Fee Simple
• Parking Types: Detached Garage
• Patio And Porch Features: Porch, Patio
• Possession: Settlement
• Sale Type: Standard
• Sewer: Public Sewer
• Tax Annual Amount: 20218
• Tax Year: 2025
• Total Public Open Houses: 1
• Total Stories: 4
• Total Taxes Payment Frequency: Annually
• Upper Level 1 Bedrooms: 3
• Upper Level 1 Full Baths: 2
• Upper Level 1 Total Baths: 2
• Upper Level 2 Bedrooms: 2
• Upper Level 2 Full Baths: 1
• Upper Level 2 Total Baths: 1
• Upper Levels Total Baths: 3
• Upper Levels Total Bedrooms: 5
• Upper Levels Total Full Baths: 3
• Water Body Type: River
• Water Oriented: Yes
• Water Source: Public
• Year Built Source: Estimated