Victorian

105 HIGH STREET

CHESTERTOWN , MD 21620

MLS#: MDKE2005890

$1,395,500

Status: Active
Listing number: MDKE2005890
Listing provided by: Coldwell Banker Chesapeake Real Estate Company
Listing agent phone: None
Last update: 2 days ago
New on site 3 days ago
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CHESTERTOWN HISTORIC DISTRICT - Residential

Property

Beds

5

Full Baths

4

1/2 Baths

1

Year Built

1863

Sq.Footage

3,243

This masterpiece is finally complete. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom House which was one of the original British Royal Ports of Entry to the Americas. The current owners include one of Kent County's renowned builders and craftsmen who decided to take on this restoration as a passion project to honor its beauty and significance in the community. The home was completely updated in 2024 and 2025 with new HVAC, Electrical, Plumbing, roofing, and wood flooring. The floor plan was opened up to accommodate your lifestyle in 2025. New bathrooms and kitchen were custom designed. A grand 3 story staircase greets you at the foyer along with arched entryways to introduce you to the level of detail to be found throughout. The front porch allows you to sit back to watch everything happening in town or simply admire the water. The updated layout is designed for optimal flow and natural light. The primary suite captivates you with a fireplace, spacious walk in closet, and tiled shower room with views of the water from two sides. The Mansard roof allows for the full third floor. In the basement there is a partially finished space perfect for your wine cellar along with extra unfinished tidy space for storage. There is also a fenced in rear yard perfect for intimate gatherings, pets, and gardening. Off street parking is a huge plus as well with a detached garage connecting to the rear yard. Don't miss out on this perfect of historic charm with modern amenities walking distance to all Chestertown has to offer.

Features & Amenities

Interior

  • Total Bedrooms

    5

  • Bathrooms

    4

  • 1/2 Bathrooms

    1

  • Above Grade Finished Area

    3243.0

  • Basement YN

    YES

  • Cooling YN

    YES

  • Cooling

    Central Air, Electric

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Electric, Propane, Heat Pump

  • Pet friendly

    N/A

Exterior

  • Garage

    Yes

  • Garage spaces

    1

  • Construction Materials

    Frame

  • Parking

    Garage, Detached

  • Patio and Porch Features

    Porch, Patio

  • Pool

    Yes

  • Pool Features

    None

  • Waterfront YN

    NO

  • View

    Water, River, Scenic

Area & Lot

  • Lot Size(acres)

    0.06

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Victorian

Price

  • Sales Price

    $1,395,500

  • Tax Amount

    20218.0

  • Sq. Footage

    3, 243

  • Price/SqFt

    $430

HOA

  • Association

    No

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • Foundation Details

    Permanent

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Water Source

    Public

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Location

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Listing Courtesy of Michael ONeill , Coldwell Banker Chesapeake Real Estate Company

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This masterpiece is finally complete. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom House which was one of the original British Royal Ports of Entry to the Americas. The current owners include one of Kent County's renowned builders and craftsmen who decided to take on this restoration as a passion project to honor its beauty and significance in the community. The home was completely updated in 2024 and 2025 with new HVAC, Electrical, Plumbing, roofing, and wood flooring. The floor plan was opened up to accommodate your lifestyle in 2025. New bathrooms and kitchen were custom designed. A grand 3 story staircase greets you at the foyer along with arched entryways to introduce you to the level of detail to be found throughout. The front porch allows you to sit back to watch everything happening in town or simply admire the water. The updated layout is designed for optimal flow and natural light. The primary suite captivates you with a fireplace, spacious walk in closet, and tiled shower room with views of the water from two sides. The Mansard roof allows for the full third floor. In the basement there is a partially finished space perfect for your wine cellar along with extra unfinished tidy space for storage. There is also a fenced in rear yard perfect for intimate gatherings, pets, and gardening. Off street parking is a huge plus as well with a detached garage connecting to the rear yard. Don't miss out on this perfect of historic charm with modern amenities walking distance to all Chestertown has to offer.

105 HIGH STREET

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