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105 High St, 
Chestertown, MD 21620

$1,395,500


5

Beds


5

Baths


3,243

Sq Ft


Single Family


Virtual Tour

Active

Last updated:

April 27, 2026, 01:44 PM

MLS#

MDKE2005890

Source:

BRIGHTMLS

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About This Home

105 High St

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.

Home Facts

Single Family

5 Baths

5 Bedrooms

Built in 1863

Price Summary

1,395,500

$430 per Sq. Ft.

MLS #:

MDKE2005890

Last Updated:

April 27, 2026, 01:44 PM

Added:

5 month(s) 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. © 2026 Bright Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.