105 High Street
Chestertown, MD 21620
- 5 beds
- 5 baths
- 3,243 sqft
- 2,688 sqft lot
- $430 per sqft
- 1863 build
This is your chance to own one of the most prominent homes in Chestertown's Historic District already completely upgraded and finished to suit. 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 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. Due to this property's grandeur and scope of work, the sellers are going to let you decide on finishes such as countertops, floor stains, wall colors, and fixtures to make you feel you spend wisely. Allowance lists to be provided to interested parties. Turn this important and updated piece of Chestertown History into your Legacy property.
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Last updated Mar 28, 2025
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MLS# MDKE2005002 —
The Building
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Year Built:1863
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Year Built Source:Estimated
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New Construction:No
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Construction Materials:Frame
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Structure Type:Detached
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Architectural Style:Victorian
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Historic:Yes
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Levels:4
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Accessibility Features:None
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Foundation Details:Permanent
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Basement:Yes
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Basement Type:Improved, Interior Access
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Total SqFt Source:Assessor
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Total Below Grade SqFt:992
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Total Below Grade SqFt Source:Assessor
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Above Grade Finished Area Units:Square Feet
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Above Grade Finished SqFt:3243
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Above Grade Finished SqFt Source:Assessor
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Below Grade Finished Area Units:Square Feet
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Below Grade Unfinished Area Units:Square Feet
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Below Grade Finished SqFt Source:Assessor
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Below Grade Unfinished SqFt:992
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Below Grade Unfinished SqFt Source:Assessor
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Tax Total Finished SqFt:3243
Interior
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Fireplace:Yes
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Fireplaces:2
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Living Area SqFt Source:Assessor
Room Dimensions
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Total SqFt:4235
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Living Area SqFt:3,243 Sqft
Financial & Terms
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Sale Type:Standard
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Possession:Settlement
Location
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Directions:From 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.
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Cross Street:Water Street
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Latitude:39.20731000
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Longitude:-76.06417000
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Location Type:Downtown
The Property
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Property Type:Residential
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Lot Size Units:Square Feet
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Lot Size Acres:0.06
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Lot Size Source:Assessor
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Lot SqFt:2,688 Sqft
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Zoning:R-3
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View:Water, Scenic Vista, River
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In City Limits:Yes
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Outdoor Living Structures:Porch(es), Patio(s)
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Other Structures:Above Grade, Below Grade
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Waterview:Yes
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Waterfront:No
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Water Oriented:Yes
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Water Access:No
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Distance To Water:Blocks
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Distance To Body Of Water:1
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Water Body Name:Chester River
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Water Body Type:River
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Navigable Water:No
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Tidal Water:No
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Land Use Code:R
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Riparian Rights:No
Listing Agent
- Contact info:
- Agent phone:
- (443) 480-4275
- Office phone:
- (410) 778-0330
Taxes
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Tax ID Number:1504018273
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Tax Year:2024
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Tax Annual Amount:$8,208
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Tax Assessed Value:$633,867
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Year Assessed:2024
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County Tax:5940.00
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City/Town Tax:2268.00
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Total Taxes Payment Frequency:Annually
Beds
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Bedrooms:5
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Upper Level Bedrooms:5
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Upper Level 1 Bedrooms:3
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Bedrooms Upper Level:2
Baths
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Total Baths:5
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Full Baths:4
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Half Baths:1
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Main Level Baths:2.00
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Main Level Full Baths:1
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Main Level Half Baths:1
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Upper Level Full Baths:3
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Upper Level Total Baths:3
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Upper Level Total Baths:2.00
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Upper Level 2 Total Baths:1.00
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Upper Level Full Baths:2
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Upper Level 2 Full Baths:1
Heating & Cooling
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Cooling Type:Central A/C
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Central Air:Yes
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Cooling Fuel:Electric
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Heating:Yes
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Heating Type:Heat Pump(s)
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Heating Fuel:Electric, Propane - Leased
Utilities
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Sewer/Septic:Public Sewer
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Hot Water:Propane
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Water Source:Public
Schools
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School District Name:Kent County Public Schools
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School District Source:Listing Agent
The Community
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Subdivision Name:Chestertown Historic District
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Senior Community:No
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Pool:No Pool
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HOA:No
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Condo/Coop Association:No
Parking
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Total Garage and Parking Spaces:1
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Garage:Yes
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Garage Features:Garage - Side Entry
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Garage Spaces:1.00
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Type of Parking:Detached Garage
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# of Detached Garage Spaces:1
Extra Units
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Vacation Rental:No
Monthly cost estimate

Asking price
$1,395,000
Expense | Monthly cost |
---|---|
Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$7,469
|
Taxes | $684 |
Insurance | $383 |
Utilities | $337 See report |
Total | $8,873/mo.* |
*This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
Date | Event | Source | Price | % Change |
---|---|---|---|---|
3/28/25
Mar 28, 2025
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Listed / Active | BRIGHT | $1,395,000 |