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5 Beds
5 Baths
3,243 sqft

$1,195,000

105 HIGH STREET, CHESTERTOWN MD, 21620

Price per sqft$368.49
Built in1863
Property size3,243 sqft
Property typeResidential

Overview

Active

Active-bright

Listed Nov 7, 2025

Updated 6h ago

Morning light pours through restored original windows. The river shimmers a block away, and a mansard roof that has watched over High Street since 1863 frames it all. Rebuilt after the fire of its day, the Tilley Residence has been brought back since 2022 by a top builder and his designer sister. A grand staircase, refinished by hand over many months, rises past glimpses of the water. The new custom kitchen is made for gathering. Upstairs, the primary suite has its own fireplace, and there are 4.5 brand-new baths. Below, a bright lower level holds a wine cellar. Everything unseen is new, too: HVAC, electrical, plumbing, roof and insulation. Outside, there’s a private fenced yard, a remodeled garage, and the historic Custom House next door. Shops, galleries, dining and the marina are all a short stroll away. There is no better chance to drop your keys and create your legacy in Chestertown's Historic District.

$7,950/mo

Est. mortgage payment based on a $1,195,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
MDKE2005890

Interior Features

Bedrooms
5
Bathrooms
5
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.06 Acres

Other Property Details

Taxes
$20,218
Tax Frequency
Annually
Garage
Yes
View
Yes
55+/Senior Community
No
MLS provider logo

Listed by Coldwell Banker Chesapeake Real Estate Company
Listing Contact: 4434804275 

The IDX display contains information sourced from the Bright MLS, Inc. as of 10/23/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

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Data last updated on 10/23/2026 at 4:33 AM UTC

 

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