$1,245,500

5 Bedrooms Single Family Detached

  • 5 Beds
  • 5 Baths
  • 3,243 Sqft
  • 2,614 Sqft lot
  • Updated: September 22
  • MLS#MDKE2005890

About the Property

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 system
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.
…
  • Property type

    House

  • Year built

    1863

  • Price/sqft

    $384

Features

Features

Lot

Indoor

  • Fireplace
  • Air Conditioning
  • Kitchen island
  • Gas Stovetop
  • Bar
  • Basement
  • Stone Countertops

Outdoor

Explore the Area

105 High Street, Chestertown, MD 21620, Maryland, United States View on Google Maps
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Michael O'Neill

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Michael O'Neill
Maryland, United States
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2026
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Coldwell Banker Chesapeake Real Estate Company - Chestertown
Coldwell Banker Chesapeake Real Estate Company - Chestertown
114 S. Cross Street, Suite B, 21620, Chestertown, Maryland, United States
View agency profile
Coldwell Banker Chesapeake Real Estate Chestertown office serves Kent & Queen
Anne Counties the Land o
Coldwell Banker Chesapeake Real Estate Chestertown office serves Kent & Queen
Anne Counties the Land of Pleasant Living. Our offices are conveniently located
at 114B S. Cross Street, Chestertown, Maryland. Our Company knows that you
expect more from your real estate broker. You are a busy and successful
professional that demands timely, sophisticated, and knowledgeable customer
service even here on Maryland’s timeless eastern shore.  Our Company also knows
that our time-honored business model is undergoing epic and dynamic change. We
are making every effort to stay ahead of these profound changes.
…
Last updated
September 22
First listed
September 22
Listing reference
wck8zh
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