105 High St

Chestertown, MD 21620
  • $1,395,500

    Price
  • 5

    Bed
  • 4.5

    Bath
  • 3,243

    SqFt

About the Listing CBCE2 - 3337613

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.

Listing Highlights

Status Active
Days on Site 42
Property Type Residential
MLS ® MDKE2005890
Year Built 1863
Total Square Footage 3,243
Lot/Acreage 0.06

Interior Details

  • Bedrooms: 5
  • Bathrooms: 4 Full / 1 Half
  • Appliances:
  • Air Cond: Central A/C
  • Heating: Heat Pump(s)
  • Fireplaces: 2, 2 Fireplaces
  • Floor:
  • Above Ground Sq Ft: 3243
  • Below Ground Sq Ft: 0
  • Basement: Improved,Interior Access
  • Other:
  • Water: Public

Exterior Details

  • Lot Description: Not New Construction,Horse Property: No,In City Limits
  • Garage Capacity: 1 car
  • Parking Spaces: 1
  • Zoning: R-3
  • Roof:
  • Others:
  • Sewer: Public Sewer
  • Parking Features: Garage - Side Entry,Detached Garage,1+ Spaces

Financial Details

  • Tax Amount: $20,218
  • Taxes w/Assessments: N/A
  • Tax/Property ID: N/A
  • Tax Year: 2025

Payment Calculator

Monthly Payment

  • in Principal and Interest
  • in Taxes
Years
% Down Payment
% Mortgage Rate

Questions About..

105 High St Chestertown, MD 21620

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Never Miss A New Property

Get notified any time there's a new home on the market in this neighborhood!

Don't worry! We'll never spam you or sell your details. You can unsubscribe whenever you'd like.

Originating MLS: BRIGHT_MAIN

home

Are you buying or selling a home?

Buying
Selling
Both
home

When are you planning on buying a new home?

1-3 Mo
3-6 Mo
6+ Mo
home

Are you pre-approved for a mortgage?

Yes
No
Using Cash
home

Would you like to schedule a consultation now?

Yes
No

When would you like us to call?

Thanks! We’ll give you a call as soon as possible.

home

When are you planning on selling your home?

1-3 Mo
3-6 Mo
6+ Mo

Would you like to schedule a consultation or see your home value?

Schedule Consultation
My Home Value

or another way