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$1,395,500

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,235 Sq. Ft.
  • 1 Car Garage
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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. 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 offering-historic charm blended with modern amenities.

Full Property Details for 105 High St

General

  • Price: $1,395,500
  • Taxes: $20,218 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDKE2005890
  • Updated: 12/17/2025
  • Added to Site: 69 day(s) ago

Interior

  • Fireplace: Yes
  • Number of Fireplaces: 2

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Upper 2 - Full Baths: 1
  • Upper Floor Baths: 3
  • Upper - Full Baths: 3
  • Main Floor Baths: 2
  • Main - Full Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 5
  • Bedrooms-Up2: 2

Exterior

  • Porch/Patio/Deck: Porch(es), Patio(s)

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Total Spaces: 1
  • Parking Type: Detached Garage
  • Garage Description: Garage - Side Entry

Location

  • Municipality: Chestertown
  • County: KENT
  • Subdivision: CHESTERTOWN HISTORIC DISTRICT
  • Cross Streets: Water Street
  • Driving 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.
  • Location Details: Downtown
  • City Limits: Yes

School Information

  • School District: Kent County Public Schools

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric, Propane - Leased
  • Water Heater: Propane

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Dist. to Water: 1 Blocks

Structural Information

  • Architectural Style: Victorian
  • Structure Type: Detached
  • Construction: Frame
  • Basement: Yes
  • Basement Desc.: Improved, Interior Access
  • Foundation: Permanent
  • Stories Description: Main, Upper 1, Upper 2
  • Square Feet: 4,235
  • Sq. Ft. Source: Assessor
  • Living Area: 3,243 Sq. Ft.
  • Finished Above Grnd: 3,243 Sq. Ft.
  • Year Built: 1863
  • Year Built Source: Estimated

Additional Structures

  • Other Structures: Garage(s)

Lot Features

  • Property View: Water, Scenic Vista, River
  • Lot Size (Acres): 0.06
  • Lot Size (Sq. Ft.): 2,688
  • Lot Size Source: Assessor
  • Zoning: R-3

Water Features

  • Water View: Yes
  • Water Front Type: River

Financial Considerations

  • Price Per Sq. Ft.: $430.31
  • City/TownTax: $5,588
  • City/TownTax Freq: Annually
  • Tax w/Assessment: $1,290,100
  • Tax Amount: $20,218
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill

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Listing agent

— 105 High St —

  • Michael ONeill

    Coldwell Banker Chesapeake Real Estate Company

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 105 High St

School District:Kent County Public Schools
NameGradesDistance
Kent County Middle School
402 East Campus Avenue, Chestertown, MD 21620
6-80.7 mi
Kent County High School
25301 Lambs Meadow Road, Worton, MD 21678
9-125.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 105 High St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/07/2025
Listed
$1,395,500
597.75%
MLS
8/31/2022
Sold
$200,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 105 High St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$20,218
104%
$1,290,100
104%
2024
$9,934
29%
$633,867
25%
2023
$7,682
—
$508,533
3%
2022
$7,682
—
$493,300
—
2020
$7,674
—
$491,467
—
2021
$7,674
-50%
$489,633
—
2020
$15,210
101%
$487,800
—
2019
$7,580
21%
$487,800
—
2018
$6,280
5%
$487,800
—
2017
$6,007
291%
$487,800
—
2016
$1,535
-72%
$487,800
—
2015
$5,499
109%
$487,800
-2%
2014
$2,636
—
$495,800
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill

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105 High Street, Chestertown, MD 21620 (MLS# MDKE2005890) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 105 High Street is currently listed for $1,395,500 and was received on November 07, 2025. Want to learn more about 105 High Street? Do you have questions about finding other Single Family real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.

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