Chestertown, MD 21620 105 High Street

$1,245,500

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Presented By: Coldwell Banker Chesapeake Real Estate Company
  • MLS# MDKE2005890
  • 11/07/2025
  • Request Tour
  • Request Info
  • Beds • 5
  • Full/Half Baths • 4 / 1
  • SQFT • 3,243
  • Garage • 1

Home Details

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertowns 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 Shores 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 livinglaid 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 Marylands most beloved waterfront towns.
Presented By: Coldwell Banker Chesapeake Real Estate Company

Interior Features for 105 High Street

Bedrooms

Bedrooms Count All Upper Levels5
Bedrooms Count Upper Level 13
Bedrooms Count Upper Level 22
Main Level Bedrooms
Total Bedrooms5

Bathrooms

Bathrooms Half Upper Level 20
Bathrooms Half Upper Level 10
Bathrooms Half Main Level1
Bathrooms Half All Upper Levels0
Bathrooms Full Upper Level 21
Bathrooms Full Upper Level 12
Bathrooms Full All Upper Levels3
Bathrooms Count Upper Level 21.00
Bathrooms Count Upper Level 12.00
Bathrooms Count All Upper Levels3
Half Baths1
Total Baths5

Other Interior Features

LivingAreaSourceAssessor
Below Grade Unfin Area UnitsSquare Feet
Below Grade Unfin SQFT992
Below Grade Unfin SQFT SourceAssessor
Above Grade Finished Area3243
Above Grade Finished Area SourceAssessor
Above Grade Finished Area Unit TypeSquare Feet
BasementImproved, Interior Access
Basement (Y/N)Yes
Below Grade Finished Area
Below Grade Finished Area SourceAssessor
Below Grade Finished Area Unit TypeSquare Feet
Central Air Y/NYes
Fireplace Y/NYes
Heating FuelElectric, Propane - Leased
Heating Y/NYes
Hot WaterPropane
Total Fireplaces2

Other Rooms

Room TypeBedroom 2, Bedroom 3, Bedroom 1, Bathroom 1, Bathroom 2, Half Bath

Room Details for 105 High Street

Bathroom 1

level Main

Bathroom 1 # 2

level Upper 1

Bathroom 1 # 3

level Upper 2

Bathroom 2

level Upper 1

Bedroom 1

level Upper 1

Bedroom 1 # 2

level Upper 2

Bedroom 2

level Upper 1

Bedroom 2 # 2

level Upper 2

Bedroom 3

level Upper 1

Half Bath

level Main

General for 105 High Street

AccessibilityNone
Architectural StyleVictorian
Bathrooms Count Main Level2.00
Bathrooms Full Main Level1
CityCHESTERTOWN
Condo/Coop Association fee Y/NNo
Construction MaterialsFrame
Cool FuelElectric
CoolingCentral A/C
CountyKENT
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.
Full Baths4
Garage Spaces1.00
Garage Y/NYes
HOANo
HeatingHeat Pump(s)
Levels4
Living Area3243
Location TypeDowntown
Lot Size Square Feet2688.00
Lot Size UnitsSquare Feet
MunicipalityChestertown
New ConstructionNo
Other StructuresAbove Grade, Below Grade
OwnershipFee Simple
Patio/Porch FeaturesPorch(es), Patio(s)
PossessionSettlement
Price Per Sq Ft Total AG384.06
Property TypeResidential
School DistrictKENT COUNTY PUBLIC SCHOOLS
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusACTIVE
Structure TypeDetached
Subdivision NameCHESTERTOWN HISTORIC DISTRICT
Tax Annual Amount20218.0
Tax Assessed Value1290100.0
Tax Year2025
Total Rooms10
Total SQFT4235
Vacation Rental Y/NNo
ViewWater, Scenic Vista, River
Virtual TourClick here
Water Access Y/NNo
Year Built1863
Year Built SourceEstimated
ZoningR-3

Exterior for 105 High Street

# of Detached Garage Spaces1
Foundation DetailsPermanent
Garage FeaturesGarage - Side Entry
Lot Size Acres0.06
Lot Size SourceAssessor
Navigable Water Y/NNo
PoolNo Pool
Total Parking Spaces1
Type of ParkingDetached Garage
Water Body TypeRiver
Water Oriented Y/NYes
Water SourcePublic
Water View Y/NYes
Waterfront Y/NNo

Additional Details

Price History

Hope Raymond-Martinez

Agent
Price $1,245,500
MLS#MDKE2005890
List Date 11/07/2025
Property Type Single Family
Phone (386) 383-3266
Request Tour
Request Info
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