105 High Street
Chestertown, MD 21620

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Description

This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown's most prominent corners, neighboring Widehall and the Custom House. Expertly restored in 2024–2025 by one of Kent County's premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths balance modern comfort with timeless character. A grand three-story staircase and arched entryways welcome you inside. The front porch overlooks town and offers water views. The primary suite includes a fireplace, walk-in closet, and a tiled shower room with views from two sides. The Mansard roof provides a full third floor, and the basement includes a great wine cellar opportunity plus ample storage. A fenced rear yard, off-street parking, and a detached garage complete this rare offering—historic charm blended with modern amenities.

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
• 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
• 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 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