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215.704.5057
The Javada Hill Team logo
A real estate company with a purpose. Our mission is to help
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215.704.5057
The Javada Hill Team logo
A real estate company with a purpose. Our mission is to help
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MD
Kent
Chestertown
chestertown historic district
21620
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MD
Kent
Chestertown
chestertown historic district
21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
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$1,395,500

105 HIGH ST, Chestertown, MD, 21620

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105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
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105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620
105 HIGH ST, Chestertown, MD, 21620

Information

Price: $1,395,500
Days On Market: 160
Year Build: 1863
Total Baths: 5
Full Baths: 4
Half Baths: 1
Bedrooms: 5
MLS ID: MDKE2005890
Status: Active

Details

Address: 105 HIGH ST
County: Kent
City: Chestertown
Neighborhood: chestertown historic district
Zip: 21620
State: Maryland

Taxes

Property Taxes: $20,218
Tax Year: 2025
Tax Amount: $20,218

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.

Location

Listed By

Listing Agent

Michael ONeill

murphy@cbchesapeake.com
Coldwell Banker Chesapeake Real Estate Company

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Print Details
105 HIGH ST, Chestertown, MD, 21620
Listing information provided courtesy of the Bright MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable, but is not guaranteed accurate by the MLS. Updated: 29th April, 2026 8:27 PM (UTC)
Listing Agent: Michael ONeill
Listing Office: Coldwell Banker Chesapeake Real Estate Company
Attribution contact:

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