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105 High St, 
Chestertown, MD 21620

$1,395,500


5

Beds


5

Baths


3,243

Sq Ft


Single Family

Active

Last updated:

December 18, 2025, 02:45 PM

MLS#

MDKE2005890

Source:

BRIGHTMLS

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About This Home

105 High St

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.

Home Facts

Single Family

5 Baths

5 Bedrooms

Built in 1863

Price Summary

1,395,500

$430 per Sq. Ft.

MLS #:

MDKE2005890

Last Updated:

December 18, 2025, 02:45 PM

Added:

a month ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

4

Interior

Living Area:

3,243 Sq. Ft.


Structure

Structure

Architectural Style:

Victorian

Building Area:

3,243 Sq. Ft.

Year Built:

1863


Lot

Lot Size (Sq. Ft):

2,613


Finances & Disclosures

Finances

Price:

$1,395,500

Price per Sq. Ft:

$430 per Sq. Ft.

105 High St
Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2025 Bright Mls All rights reserved.

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By clicking Contact I agree a Coldwell Banker Agent may contact me by phone or text message including by automated means and prerecorded messages about real estate services, and that I can access real estate services without providing my phone number. I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.