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$1,195,000
Monthly Est:$5,948
5 Beds
5 Baths4 full baths + 1 half bath
3,243sqft
105 High St, Chestertown, MD 21620
$1,195,000
$5,948/moEst:
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Single Family Residence
Built in 1863
$-- HOA
2,688 sqft lot
$368/sq.ft
Description
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.
- Houzeo last checked: 12 hours ago
- Listing updated: October 22, 2026 at 1:28 pm
- Listing Provided by: Michael ONeill (443) 480-4275 | Coldwell Banker Chesapeake Real Estate Company (410) 778-0330
- Source: Bright MLS-NJ | MLS#: MDKE2005890
Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1863
HOA Fees
-
Finished Area
3,243 sqft
Lot Size
2,688 sqft lot
Basement Area
- sqft
MLS Name
Bright MLS
MLS Number
MDKE2005890
MLS Status
ACTIVE-BRIGHT
Days on Market
350
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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 5
Bathrooms: 5
Interior
Heating
Heat Pump(s)
Sewer
Public Sewer
Cooling
Central A/c
Construction
Year Built
Year Built: 1863
Home type
Single Family Residence
Construction Materials
Frame
Architectural Style
Victorian
Foundation Details
Permanent
Utilities & Energy
Basement
Improved, Interior Access
Water Source
Public
Other Features
Subdivision Name
Chestertown Historic District
Patio And Porch Features
Porch, Patio
Price History
| Date | Event | Price |
|---|---|---|
10/20/2026 Source: | Price Decreased | $1,195,000 -4.05% $368/sqft |
06/26/2026 Source: | Price Decreased | $1,245,500 -10.75% $384/sqft |
11/07/2025 Source: | Price Increased | $1,395,500 +7.72% $430/sqft |
11/07/2025 Source: | Price Decreased | $1,295,500 -7.13% $399/sqft |
03/28/2025 Source: | Listed for Sale | $1,395,000 $430/sqft |
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