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  • 105 High Street, Chestertown, MD 21620 Main Photo

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Price Reduced $50,500 on October 20th, 2026
BEDS5 BATHS4 full 1 partial SQUARE FEET3,243 MLS#MDKE2005890
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONCHESTERTOWN HISTORIC DISTRICT SCHOOLKENT COUNTY PUBLIC SCHOOLS

Property 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.

105 High Street | MLS# MDKE2005890

This single family home located at 105 High Street, Chestertown, MD 21620 is currently listed for sale with an asking price of $1,195,000. This property was built in 1863 and has 5 bedrooms and 4 full and 1 partial baths with 3243 sq. ft. High Street is located in the CHESTERTOWN HISTORIC DISTRICT subdivision within the KENT COUNTY PUBLIC SCHOOLS school district. Search CHESTERTOWN HISTORIC DISTRICT real estate on www.victoryhometeamrealty.com today.

Upcoming Open Houses

Open House Sunday November 1st, 11:00am - 1:00pm

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Improved, Interior Access
Cooling: Central A/C
Fireplaces: 2
Fuel Type: Electric, Propane - Leased
Garage: 1
Heating: Heat Pump(s)
Home Style: Victorian
Lot Size: 0.06 Acres
Stories: 4.0
Taxes: $20,218
Year Built: 1863

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Exterior: Frame
Location: Downtown
Lot Dimensions: 0.06 Acre(S)
Municipality: Chestertown
Number of Rooms: 10
Parking Notes: 1 Total Parking Spaces
Rooms: Bedroom 2,Bedroom 3,Bedroom 1,Bathroom 1,Bathroom 2,Half Bath
Sewer: Public Sewer
Special View Info: Water, Scenic Vista, River
SQFT Above Finished: 3243
SQFT Total Finished: 3243
Structure Type: Detached
Total Garage/Parking Spaces: 1
Water: Public

Local Schools

School District: KENT COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Coldwell Banker Chesapeake Real Estate Company
Agency Phone: 4107780330

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Estimated Payment

$ 4,692.93 per month $2,659.55 Principal & Interest $1,684.83 Property Tax $348.54 Homeowner's Insurance

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