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Rock Hall Properties Real Estate
Main Office:
410-639-4003
cindy@rockhallproperties.com
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Rock Hall Properties Real Estate
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Main Office:
410-639-4003
cindy@
rockhallproperties.com
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FOR SALE
$1,395,500

105 HIGH Street
Chestertown, MD 21620

Single Family, Single Family-Detached
Residential
5
Beds
4
Baths
3,243
Sq. Ft.
0.06
Acre Lot
Courtesy: Coldwell Banker Chesapeake Real Estate Company
brightmlshomes.com> Maryland> Chestertown> 21620
This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertowns most prominent corners, neighboring Widehall and the Custom House. Expertly restored in 2024-2025 by one of Kent Countys 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.
MDKE2005890
Single Family, Single Family-Detached, Victorian
5
Chestertown
KENT
4 Full/1 Half
1863
0.06 Acres
LP Gas Water Heater, Public Water Service
Frame
Public Sewer
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The scores below measure the walkability of the address, access to public transit of the area and the convenience of using a bike on a scale of 1-100

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Courtesy: Coldwell Banker Chesapeake Real Estate Company
This content last refreshed on 2/11/2026 12:04 PM CST. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Information is deemed reliable but is not guaranteed.