—

Baths

3,243 Sq. Ft.

$430 / Sq. Ft.

3,243

Sq. Ft.

$430

per Sq. Ft.

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105 High Street Chestertown, MD 21620 - Photo 1 of 51

Fireplace log set to be installed before closing

Description

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...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.

Listed by Michael ONeill • Coldwell Banker Chesapeake Real Estate Company
P: (443)-480-4275 murphy@cbchesapeake.com

Property Details for 105 High Street

Tax ID Number

1504018273

Ownership

Fee Simple

Condo Coop Association

HOA

Structure Type

Detached

Style

Victorian

Levels/Stories

Waterfront

LISTING UPDATED: 02/26/2026 02:09 PM

Property Details for 105 High Street

Status	Active
MLS #	MDKE2005890
Days on Market	113
Taxes	$20,218 / year
HOA Fees	-
Condo/Co-op Fees	-
Compass Type	Single Family
MLS Type	Residential / Fee Simple
Year Built	1863
Lot Size	0.06 AC / 2,688 SF
County	Kent County

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Location

Listing Courtesy of Coldwell Banker Chesapeake Real Estate Company

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Building Information for 105 High Street

Stories4Year Built1863Building Size-Lot Size0.06 AC / 2,688 SF

Payment Calculator

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$8,486 per month

30 year fixed, 6.15% Interest

Principal and Interest

$6,801

Property Taxes

$1,685

HOA Dues

The Payment Calculator is for illustrative purposes only.

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Property Information for 105 High Street

Location

In City Limits: Yes
School District Name: KENT COUNTY PUBLIC SCHOOLS

School District County ID: 121139164602
SchoolDistrictSource: Listing Agent
County: KENT

Waterfront / Water Access

Water View: Yes
Water Access: No

Water Oriented: Yes
Navigable Water: No
Tidal Water: No
Water Body Type: River
Riparian Rights Y/N: No
Distance To Body Of Water: 1.00
Distance To Body Of Water Units: Blocks

Association / Community Info

Senior Community: No

Taxes and Assessment

Tax Year: 2025
Tax Assessed Value: $1,290,100

City Town Tax: $5,588
Zoning: R-3
Automatically Update Tax Values Y/N: Yes

Rooms

Main

# Bedrooms Count Main Level: 0
# Bathrooms Count Main Level: 0

# Bathrooms Full Main Level: 0
# Bathrooms Half Main Level: 0

Rooms

Stories: Main

Building Info

Total Finished SQFT: 3,243.00
Total Finished SQFT Source: Assessor

Total SQFT: 4,235.00
Total SQFT Source: Assessor
Construction Materials: Frame
Ext Main Mid-res: http://bright-media02.prd.brightmls.com/bright/images/0000/8042/9890/3574/804298903574_512_384_WM_9tNWzzv8SWwFMitz.jpg
Basement Type: Improved, Interior Access
Foundation Details: Permanent
# Bathrooms Full: 0
# Bathrooms Half: 0
Other Structure: Garage(s)

Lot / Land Information

Lot Size Source: Assessor
Location Type: Downtown

Parcel ID: 4505498

Parking

Type Of Parking: Detached Garage
Num of Detached Garage Spaces: 1

Total Garage Spaces: 1
Garage Features: Garage - Side Entry

Interior Features

Fireplace: Yes
Fireplaces Count: 2

Accessibility Features: None

Exterior Features

Outdoor Living Structures: Porch(es), Patio(s)
Pool: No Pool

Utilities

Heating: Yes
Cooling Type: Central A/C

Cooling Fuel: Electric
Heating Type: Heat Pump(s)
Heating Fuel: Electric, Propane - Leased
Hot Water: Propane
Water Source: Public
Sewer Septic: Public Sewer

Confidential Data

Listing Office

List Agent AOR: Mid-Shore Board of REALTORS

Property History for 105 High Street

Date	Event & Source	Price	Appreciation
Nov 7, 2025	Withdrawn BRIGHT #MDKE2005002		—
Nov 7, 2025	Listed (Active) BRIGHT #MDKE2005890	$1,395,500	—
Apr 29, 2025	Price Change BRIGHT #MDKE2005002	$1,395,500	—
Mar 28, 2025	Listed (Active) BRIGHT #MDKE2005002	$1,395,000	—
Aug 31, 2022	Closed (Public Record) Public Record #1497070904	$200,000	—
May 6, 2015	Withdrawn BRIGHT #1007595244	$495,000	—
May 6, 2015	Withdrawn BRIGHT #1007595244		—
Mar 6, 2014	Listed (Active) BRIGHT #1007595244	$595,000	—

Date	Event & Source	Price
11/07/2025	Withdrawn BRIGHT #MDKE2005002	—
11/07/2025	Listed (Active) BRIGHT #MDKE2005890	$1,395,500
04/29/2025	Price Change BRIGHT #MDKE2005002	$1,395,500
03/28/2025	Listed (Active) BRIGHT #MDKE2005002	$1,395,000
08/31/2022	Closed (Public Record) Public Record #1497070904	$200,000
05/06/2015	Withdrawn BRIGHT #1007595244	$495,000
05/06/2015	Withdrawn BRIGHT #1007595244	—
03/06/2014	Listed (Active) BRIGHT #1007595244	$595,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 105 High Street

Taxable ValueLand$350,600Additions$939,500Total$1,290,100

Tax Record2025$20,218 ($1,685 / month)

Home Facts

Beds0Baths2.5Total Finished SqFt3,243 SqFtAbove Grade Finished SqFt3,243 SqFtStories3Lot Size2,688 SqFtStyleSingle Family ResidenceYear Built1900ZoningR-3CountyKENTAPN04-018273

Schools near 105 High Street

This home is within Kent County Public Schools.


Rating	School	Type	Grades	Distance
7/10	H. H. Garnett Elementary School	Public - Nearby school	PK to 5	0.5 mi
2/10	Kent County Middle School	Public - Serves this home	6 to 8	0.7 mi
5/10	Kent County High School	Public - Serves this home	9 to 12	5.6 mi
NR	Worton Elementary School	Public - Nearby school	PK to 5	5.4 mi
5/10	Rock Hall Elementary School	Public - Nearby school	PK to 5	10.6 mi
NR	Millington Elementary School	Public - Nearby school	PK to 5	12.8 mi
NR	Chester River Adventist School	Private - Nearby school	1 to 8	0.4 mi
NR	Chestertown Christian Academy	Private - Nearby school	PK to 12	1.1 mi
NR	Radcliffe Creek School	Private - Nearby school	K to 8	1.3 mi


Rating	School	Distance
7/10	H. H. Garnett Elementary School PublicPK to 5 Nearby school	0.5 mi
2/10	Kent County Middle School Public6 to 8 Serves this home	0.7 mi
5/10	Kent County High School Public9 to 12 Serves this home	5.6 mi
NR	Worton Elementary School PublicPK to 5 Nearby school	5.4 mi
5/10	Rock Hall Elementary School PublicPK to 5 Nearby school	10.6 mi
NR	Millington Elementary School PublicPK to 5 Nearby school	12.8 mi
NR	Chester River Adventist School Private1 to 8 Nearby school	0.4 mi
NR	Chestertown Christian Academy PrivatePK to 12 Nearby school	1.1 mi
NR	Radcliffe Creek School PrivateK to 8 Nearby school	1.3 mi

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 105 High Street, Chestertown, MD 21620

105 High Street is a single family home for sale in Chestertown, MD 21620. This property was listed for sale on November 7, 2025 by Coldwell Banker Chesapeake Real Estate Company, it's currently listed at $1,395,500. It has been on the market for a total of 113 days and was last sold on August 31, 2022. This listing's school district is Kent County Public Schools. Nearby schools include H. H. Garnett Elementary School, Kent County Middle School and Kent County High School. 105 High Street is a 0-bed, 0-bath, 3,243 sqft single family home built in 1863.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Coldwell Banker Chesapeake Real Estate Company

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 02/26/2026 02:09 PM

105 High StChestertown, MD 21620

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More information about 105 High Street, Chestertown, MD 21620

105 High St
Chestertown, MD 21620