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105 High Street Chestertown, MD $ 1,395,500
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$ 1,395,500 Get more info
105 High Street
$ 1,395,500
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Open House 12/6 12pm - 2pm
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105 High Street

Chestertown, MD, 21620
$ 1,395,500
Bedrooms5 Baths4.1 Sq 3,243

Monthly Estimate*

$ 8,706

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Single Family Home for sale in Chestertown, MD

for $1,395,500 with 5 bedrooms and 4 full baths, 1 half bath. This 3,243 square foot home was built in 1863 on a lot size of 0.06.

This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertowns most prominent corners, neighboring Widehall and the Custom House. Expertly restored in 20242025 by one of Kent Countys 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. The Mansard roof provides a full third floor, and the basement includes a great wine cellar opportunity plus ample storage. A fenced rear yard, off-street parking, and a detached garage complete this rare offeringhistoric charm blended with modern amenities.

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Open House

12/6/2025 12:00 PM - 2:00 PM
105 High Street Chestertown, MD
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
Single Family Active

Price

$ 1,395,500

Bedrooms

5

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 20,218

Style

Victorian

Lot Size

0.06

Year Built

1863

Town/City

Chestertown

County/Region

Kent

MLS | Web ID

MDKE2005890
Features
General
Living Area 3243
Sewer Public Sewer
Heating Heat Pump(s)
Cooling Central A/C
Possession Settlement
Zoning R-3
Garage Spaces 1.00
Patio/Porch Features Porch(es) Patio(s)
Architectural Style Victorian
Construction Materials Frame
School District KENT COUNTY PUBLIC SCHOOLS
Year Built 1863
View Water Scenic Vista River
Levels 4
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Municipality Chestertown
Accessibility None
County KENT
New Construction N
Property Type Residential
HOA N
Subdivision Name CHESTERTOWN HISTORIC DISTRICT
Garage Y/N Y
Water Access Y/N N
Other Structures Above Grade Below Grade
Full Baths 4
Status ACTIVE
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.
City CHESTERTOWN
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 2688.00
Tax Annual Amount 20218.0
Structure Type Detached
Condo/Coop Association Y/N N
Bathrooms Full Main Level 1
Bathrooms Count Main Level 2.00
Price Per Sq Ft Total AG 430.31
Vacation Rental Y/N N
Location Type Downtown
Standard Status Active
Year Built Source Estimated
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Interior
Heating Fuel Electric Propane - Leased
Basement Improved Interior Access
Total Fireplaces 2
Hot Water Propane
Basement (Y/N) Y
Heating Y/N Y
Fireplace Y/N Y
Above Grade Finished Area 3243
Half Baths 1
Central Air Y/N Y
Total Bedrooms 5
Below Grade Finished Area 0
Below Grade Finished Area Unit Type Square Feet
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 5
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Exterior
Pool No Pool
Water Source Public
Garage Features Garage - Side Entry
Type of Parking Detached Garage
Foundation Details Permanent
Water View Y/N Y
Lot Size Acres 0.06
Water Body Type River
Lot Size Source Assessor
Waterfront Y/N N
Navigable Water Y/N N
Water Oriented Y/N Y
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Internal Only
Street Number 1 105
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* Excluded Features
List By
Coldwell Banker Chesapeake Real Estate Company

Broker

murphy@cbchesapeake.com

Email

Affordability Calculator

$10,391
Per Month
84%
16%
0%
Monthly Principal & Interest
$8,706
Monthly Property Taxes
$1,685
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3535796 Elementary School
3533824 Middle School
Unknown High School High School
See complete school information
Pricing History
DatePricePrice ChangeDescription
11/7/2025$1,395,500 Listed Price

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105 High Street, Chestertown, MD, 21620 is a Single Family Home for sale at $1,395,500 with 3,243 sqft and a lot size of 0.06. 105 High Street has 5 bedrooms, 4.1 baths, and was built in 1863. The property's zip code is 21620 which is in Chestertown, MD

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