Back to search
105 High Street Chestertown, MD $ 1,395,500
Share Save
$ 1,395,500 Get more info
105 High Street
$ 1,395,500
Back to search
Share Save

105 High Street

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

Monthly Estimate*

$ 8,592

105 High Street, Chestertown, MD 21620 - Image 1
105 High Street, Chestertown, MD 21620 - Image 2
105 High Street, Chestertown, MD 21620 - Image 3
105 High Street, Chestertown, MD 21620 - Image 4
105 High Street, Chestertown, MD 21620 - Image 5
105 High Street, Chestertown, MD 21620 - Image 6
105 High Street, Chestertown, MD 21620 - Image 7
105 High Street, Chestertown, MD 21620 - Image 8
105 High Street, Chestertown, MD 21620 - Image 9
105 High Street, Chestertown, MD 21620 - Image 10
105 High Street, Chestertown, MD 21620 - Image 11
105 High Street, Chestertown, MD 21620 - Image 12
105 High Street, Chestertown, MD 21620 - Image 13
105 High Street, Chestertown, MD 21620 - Image 14
105 High Street, Chestertown, MD 21620 - Image 15
105 High Street, Chestertown, MD 21620 - Image 16
105 High Street, Chestertown, MD 21620 - Image 17
105 High Street, Chestertown, MD 21620 - Image 18
105 High Street, Chestertown, MD 21620 - Image 19
105 High Street, Chestertown, MD 21620 - Image 20
105 High Street, Chestertown, MD 21620 - Image 21
105 High Street, Chestertown, MD 21620 - Image 22
105 High Street, Chestertown, MD 21620 - Image 23
105 High Street, Chestertown, MD 21620 - Image 24
105 High Street, Chestertown, MD 21620 - Image 25
105 High Street, Chestertown, MD 21620 - Image 26
105 High Street, Chestertown, MD 21620 - Image 27
105 High Street, Chestertown, MD 21620 - Image 28
105 High Street, Chestertown, MD 21620 - Image 29
105 High Street, Chestertown, MD 21620 - Image 30
105 High Street, Chestertown, MD 21620 - Image 31
105 High Street, Chestertown, MD 21620 - Image 32
105 High Street, Chestertown, MD 21620 - Image 33
105 High Street, Chestertown, MD 21620 - Image 34
105 High Street, Chestertown, MD 21620 - Image 35
105 High Street, Chestertown, MD 21620 - Image 36
105 High Street, Chestertown, MD 21620 - Image 37
105 High Street, Chestertown, MD 21620 - Image 38
105 High Street, Chestertown, MD 21620 - Image 39
105 High Street, Chestertown, MD 21620 - Image 40
105 High Street, Chestertown, MD 21620 - Image 41
105 High Street, Chestertown, MD 21620 - Image 42
105 High Street, Chestertown, MD 21620 - Image 43
105 High Street, Chestertown, MD 21620 - Image 44
105 High Street, Chestertown, MD 21620 - Image 45
105 High Street, Chestertown, MD 21620 - Image 46
105 High Street, Chestertown, MD 21620 - Image 47
105 High Street, Chestertown, MD 21620 - Image 48
105 High Street, Chestertown, MD 21620 - Image 49
105 High Street, Chestertown, MD 21620 - Image 50
105 High Street, Chestertown, MD 21620 - Image 51
105 High Street, Chestertown, MD 21620 - Image 52
105 High Street, Chestertown, MD 21620 - Image 53
105 High Street, Chestertown, MD 21620 - Image 54
105 High Street, Chestertown, MD 21620 - Image 55
105 High Street, Chestertown, MD 21620 - Image 56
105 High Street, Chestertown, MD 21620 - Image 57
105 High Street, Chestertown, MD 21620 - Image 58
105 High Street, Chestertown, MD 21620 - Image 59

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.

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertowns most prominent historic corners near Widehall and the Custom House. Completely restored in 20242025 by one of the towns most 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 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.

See more
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
Total Rooms 10
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 fee 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
See more
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
Room Type Bedroom 2 Bedroom 3 Bedroom 1 Bathroom 1 Bathroom 2 Half Bath
Main Level Bedrooms 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
See more
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
See more
Internal Only
Street Number 1 105
See more
* Excluded Features
List By
Coldwell Banker Chesapeake Real Estate Company

Broker

murphy@cbchesapeake.com

Email

Affordability Calculator

$10,277
Per Month
84%
16%
0%
Monthly Principal & Interest
$8,592
Monthly Property Taxes
$1,685
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% 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.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
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

Map

More homes like this one

homes for you

See all
See all

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

Get more info