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Homes for sale in Chestertown, MD | 105 High St, Chestertown, MD 21620 | MLS# MDKE2005890
Homes for sale in Chestertown, MD | 105 High St, Chestertown, MD 21620 | MLS# MDKE2005890
Homes for sale in Chestertown, MD | 105 High St, Chestertown, MD 21620 | MLS# MDKE2005890
Homes for sale in Chestertown, MD | 105 High St, Chestertown, MD 21620 | MLS# MDKE2005890
Homes for sale in Chestertown, MD | 105 High St, Chestertown, MD 21620 | MLS# MDKE2005890
51+
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$1,395,500

  • Beds Icon5 Beds
  • Beds Icon
    7 Baths

    4 full baths + 3 half baths

  • Beds Icon3,243sqft

105 High St, Chestertown, MD 21620

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  • Single Family Residence

  • Built in 1863

  • $-- HOA

  • 2,688 sqft lot

  • $430/sq.ft

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...

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  • Houzeo last checked: 22 Minutes ago
  • Listing updated: November 24, 2025 at 8:38 pm
  • Listing Provided by: Michael ONeill (443) 480-4275 | Coldwell Banker Chesapeake Real Estate Company (410) 778-0330
  • Source: Bright MLS-NJ | MLS#: MDKE2005890 Bright MLS-NJ

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Kent Md County

  • City

    Chestertown

  • 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

    29

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