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
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David J. Moore

David J. Moore

David J. Moore & Associates of REAL Broker, LLC

+1(410) 777-5848
Listed by Murphy ONeill • Coldwell Banker Chesapeake Real Estate Company
$ 1,395,500
Est. payment /mo
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Active

105 HIGH ST Chestertown, MD 21620

5 Beds

5 Baths

3,243 SqFt

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Detached

Listing Status Active

Purchase Type For Sale

Square Footage 3,243 sqft

Price per Sqft $430

Subdivision Chestertown Historic District

MLS Listing ID MDKE2005890

Style Victorian

Bedrooms 5

Full Baths 4

Half Baths 1

HOA Y/N N

Abv Grd Liv Area 3,243

Year Built 1863

Annual Tax Amount $20,218

Tax Year 2025

Lot Size 2,688 Sqft

Acres 0.06

Property Sub-Type Detached

Source BRIGHT

Property 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

State MD

County Kent

Zoning R-3

Rooms

Other Rooms Bedroom 2, Bedroom 3, Bedroom 1, Bathroom 1, Bathroom 2, Half Bath

Basement Improved, Interior Access

Interior

Hot Water Propane

Heating Heat Pump(s)

Cooling Central A/C

Fireplaces Number 2

Fireplace Y

Heat Source Electric, Propane - Leased

Exterior

Exterior Feature Porch(es), Patio(s)

Parking Features Garage - Side Entry

Garage Spaces 1.0

Water Access N

View Water, Scenic Vista, River

Accessibility None

Porch Porch(es), Patio(s)

Total Parking Spaces 1

Garage Y

Building

Story 4

Foundation Permanent

Above Ground Finished SqFt 3243

Sewer Public Sewer

Water Public

Architectural Style Victorian

Level or Stories 4

Additional Building Above Grade, Below Grade

New Construction N

Schools

School District Kent County Public Schools

Others

Senior Community No

Tax ID 1504018273

Ownership Fee Simple

SqFt Source 3243

Special Listing Condition Standard

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Bright MLS (BMLS)

Nearby Locations

David J. Moore

David J. Moore

Broker Associate | License ID: 609287

+1(410) 777-5848

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105 HIGH ST