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105 High StreetChestertown, MD 21620Price: $1,245,500

  • Price: $1,245,500
  • Est. Mortgage of $/month
  • 311 Days on Market
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Federal 30-year interest rate: 6.76% last updated on Sep 10, 2026
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105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
105 High Street Chestertown MD 21620
  • $1,245,500List Price
  • 5Bedrooms
  • 5Bathrooms
  • 3,243Square Feet
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.
Listed by Michael ONeill of Coldwell Banker Chesapeake Real Estate Company

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Railey Vacations

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Railey Vacations
Office: 301-387-2124
5 Vacation Way
McHenry, MD 21541

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Location Information

  • Date Listed11/07/2025
  • ZoningR-3
  • UsmAreaChestertown

Parking

  • Parking TypesDetached Garage
  • Total Garage And Parking Spaces1

Location

  • Address105 High Street
  • Area Total4,235
  • SubdivisionChestertown Historic District
  • TownChestertown
  • StateMD
  • Zip21620
  • CountyKent

Exterior

  • FoundationPermanent

Property Information

  • Lot Size Square Feet2,688
  • Above Grade Finished Area3243
  • Below Grade Area Total992
  • Below Grade Unfinished Area992

Amenities

  • PoolNo Pool
  • PricePerSqFt384
  • Other AmenitiesBasement, Fireplace, Water View

Other

  • Other Structures ListGarage(s)
  • View Count2

Basic Information

  • MLS NumberMDKE2005890
  • Ownership InterestFee Simple
  • List Price$1,245,500
  • Square Feet3,243
  • Acreage0.06
  • Year Built1863
  • MLS Property TypeResidential
  • StatusACT

Building

  • Num Detached Garage Spaces1
  • ViewWater, Scenic Vista, River
  • Water Oriented YNYes
  • Rooms
    • Bathroom 1
    • Bathroom 2
    • Bedroom 1
    • Bedroom 2
    • Bedroom 3
    • Half Bath
  • Rooms Total10
  • High School DistrictKent County Public Schools
  • LocationTypeDowntown
  • Broker NameColdwell Banker Chesapeake Real Estate Company
  • Building Number105
  • In City Limits YNYes
  • Cross StreetWater Street
  • IncorporatedcitynameChestertown
  • Distance To Body Of Water1
  • DirectionsFrom Chestertown's waterfront at the end of High Street, walk past the Customs House (one of the original British Ports of Entry) then it will be the next house on your left.
  • Distance To Body Of Water UnitsBlocks
  • Main Level Total Baths2
  • Main Level Half Baths1
  • Main Level Full Baths1
  • Upper Level2 Total Baths1
  • Upper Levels Total Full Baths3
  • Upper Levels Total Bedrooms5
  • Upper Levels Total Baths3
  • Upper Level2 Full Baths1
  • Upper Level1 Bedrooms3
  • Upper Level1 Full Baths2
  • Upper Level2 Bedrooms2
  • Upper Level1 Total Baths2
  • Story ListMain, Upper 1, Upper 2
  • Structure Design TypeDetached
  • Construction MaterialsFrame
  • Property StyleVictorian
  • Bedrooms5
  • BasementImproved, Interior Access
  • Full Bath4
  • Bathroom5
  • Half Baths1
  • Levels4
  • Fireplace YNYes
  • Fireplace2
  • Garage TypeGarage - Side Entry
  • Garage Spaces1
  • GarageYes
  • Patio And Porch FeaturesPorch(es), Patio(s)

Tax Information

  • Total Taxes Payment FrequencyAnnually
  • Tax Assessment Amount1290100
  • Tax Year2025
  • Taxes$20,218
  • City Town Tax$5,588

Basic Information

Property

  • New Construction YNN

Interior

  • Heating YNYes
  • CoolingCentral A/C
  • Basement YNYes

Utilities

  • Water SourcePublic
  • SewerPublic Sewer
  • Central Air YNYes
  • Cooling FuelElectric
  • Water HeaterPropane
  • Heating FuelElectric, Propane - Leased
  • Heat SystemHeat Pump(s)

Water Body

  • Water View YNYes
  • Water Body TypeRiver

Legal

  • Sale TypeStandard

Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Railey Vacations participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated September 14, 2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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