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$1,395,500

Est. payment - /mo

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5 Beds

5 Baths

3,243 SqFt

Active

105 HIGH ST Chestertown, MD 21620

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Additional details

Alexandra DiFilippo

alex@alexdifilippo.com +1(856) 298-9699

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

This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown's most prominent corners, neighboring Widehall and the Custom House.
Expertly restored in 2024–2025 by one of Kent County's premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths balance modern comfort with timeless character. A grand three-story staircase and arched entryways welcome you inside. The front porch overlooks town and offers water views. The primary suite includes a fireplace, walk-in closet, and a tiled shower room with views from two sides. The Mansard roof provides a full third floor, and the basement includes a great wine cellar opportunity plus ample storage. A fenced rear yard, off-street parking, and a detached garage complete this rare offering—historic charm blended with modern amenities.

Location

State MD

County Kent

Zoning R-3

Rooms

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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Alexandra DiFilippo

Agent | License ID: 1646832

+1(856) 298-9699

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