Backup offers
$8,905 Closing Credit¹
#MDKE2004966, Douglas J Ashley, Listing Office: Doug Ashley Realtors, LLC
$1,395,500 List price
105 High St Chestertown, MD 21620
$10,000
Closing credit¹
5 beds
4 full, 1 partial
3,243 sqft
0.06 acres
$430 / sqft
House
Property details
About 105 High St
This is your chance to own one of the most prominent homes in Chestertown's Historic District already completely upgraded and finished to suit. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom House which was one of the original British Royal Ports of Entry to the Americas. The current owners include one of Kent County's renowned builders and craftsmen who decided to take on this restoration as a passion project to honor its beauty and significance in the community. The home was completely updated in 2024 with new HVAC, Electrical, Plumbing, roofing, and wood flooring. The floor plan was opened up to accommodate your lifestyle in 2025. New bathrooms and kitchen were custom designed. A grand 3 story staircase greets you at the foyer along with arched entryways to introduce you to the level of detail to be found throughout. The front porch allows you to sit back to watch everything happening in town or simply admire the water. The updated layout is designed for optimal flow and natural light. The primary suite captivates you with a fireplace, spacious walk in closet, and tiled shower room with views of the water from two sides. The Mansard roof allows for the full third floor. In the basement there is a partially finished space perfect for your wine cellar along with extra unfinished tidy space for storage. There is also a fenced in rear yard perfect for intimate gatherings, pets, and gardening. Off street parking is a huge plus as well with a detached garage connecting to the rear yard. Due to this property's grandeur and scope of work, the sellers are going to let you decide on some finishes to make you feel you spend wisely. Allowance lists to be provided to interested parties. Turn this important and updated piece of Chestertown History into your Legacy property.
Highlights
Home typeSingle Family Residence
HeatingHeat Pump
StatusActive
(ACTIVE)
(ACTIVE)
CoolingCentral Air
Size3,243 sqft
BasementYes
Lot size0.06 Acres
Year built1863
ParkingGarage - Side Entry, Detached Garage
MLS #MDKE2005002
Garage1 space
ViewWater, Panoramic, River
Summary
- Partial Bathrooms: 1
- Full Bathrooms: 4
- Basement: Yes
- Total Bedroom Count: 5
- Garage Space: 1 space
- Parking: Garage - Side Entry, Detached Garage
- View: Water, Panoramic, River
- Architectural Style: Victorian
- Heating: Heat Pump
- Cooling: Central Air
- List Price: $1,395,500
- Price/SqFt: $430
- Annual Tax Amount: $9,933
- Tax Year: 2024
- 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.
- Year Built: 1863
- Living Area: 3,243 SqFt
- Municipality: Chestertown
- Lot Size: 0.06 Acres
- MLS Number: MDKE2005002
- MLS Name: BRIGHT
- Office Name: Coldwell Banker Chesapeake Real Estate Company
- Office Phone: (410) 778-0330
- Listing Agent: Michael ONeill
- Agent Phone: (443) 480-4275
- Agent Email: murphy@cbchesapeake.com
Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which participates, and is provided by BRIGHT through a licensing agreement.
The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. This home sale information is not to be construed as an appraisal and may not be used as such for any purpose.
BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors. ©2025 BrightMLS. All rights reserved.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 5/29/2025, 6:20:30 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Get an agent. Get a mortgage. Save big.¹
$1,395,500
105 High St
$10,000
closing credit¹
Sell your home with Rocket and save even more!
Seller rebate
0.5% sale price²
Price information
Property sales
| Date | Event | Price |
|---|---|---|
| Sep 07, 2022 | Home Sold | $200,000 |
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2024 | $633,867 | $9,933 |
| 2023 | $508,533 | $7,681 |
| 2022 | $493,300 | $7,681 |
| 2021 | $491,467 | $7,673 |
| 2020 | $489,633 | $7,673 |
| 2019 | $487,800 | $15,209 |
| 2018 | $487,800 | $7,580 |
| 2017 | $487,800 | $6,279 |
History based on county public records data.
Nearby schools
4
Henry Highland Garnet Elementary School
Public District PK-5
0.5 mi
•320 Calvert St
7
Church Hill Elementary School
Public District PK-4
6.1 mi
•631 Main St
7
Rock Hall Elementary School
Public District PK-5
10.5 mi
•21203 W Sharp St
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $41,287. The most common annual income of people living in Chestertown, MD is less than $<35k. The majority of families are single, no kids. Most residents in this area have post secondary degree education.
How much money do the neighbors make?
44%
<35k
32%
35k-100k
13%
100k-200k
11%
200k+
What level of education do the neighbors have?
High School Diploma
Post Secondary Degree
Masters Degree
Doctorate
What types of families live nearby?
64%
Single, No Kids
8%
Single, with Kids
24%
Married, No Kids
4%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
7%
<11 yrs old
4%
12-17 yrs old
30%
18-34 yrs old
37%
35-64 yrs old
22%
65+ yrs old
What do the neighbors do for fun?
Pro Wrestling
PGA/LPGA
College Football
Where do the neighbors shop?
Family Dollar
Stein Mart
Express/Express For Men
Where do the neighbors go to eat?
Dominos Pizza
Bob Evans
Sonic
What do the neighbors drive?
Ford
Lincoln
Kia
What do the neighbors listen to?
New Country
News/Talk/Information
Oldies
All data provided by Home Junction and Claritas
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Frequently asked questions
About 105 High St
The listing price of 105 High St property is $1,395,500.
The property 105 High St is a house located in Chestertown, Maryland, 21620.
Active Listing: 105 High St is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 105 High St are: Henry Highland Garnet Elementary School (GreatSchools Rating 4/10), Church Hill Elementary School (GreatSchools Rating 7/10), Rock Hall Elementary School (GreatSchools Rating 7/10), Kent County Middle School (GreatSchools Rating 3/10), Sudlersville Middle School (GreatSchools Rating 5/10), Centreville Middle School (GreatSchools Rating 7/10), Kent County High School (GreatSchools Rating 5/10), Queen Anne's County High School (GreatSchools Rating 8/10), Edgewood High School (GreatSchools Rating 4/10).
According to the records, the last property tax for 2024 is $9,933 (source: MLS/based on county public records data).
The last sale was on September 7, 2022 for $200,000 (source: MLS/tax record).
The property at 105 High St has 5 bedrooms and 4 full and 1 half bathrooms.
The property 105 High St is 3,243 SqFt (source: MLS/tax record).
The year of construction for 105 High St is 1863.
This home is located at 105 High St in Chestertown, MD and zip code 21620. This 3,243 square foot home, which was built in 1863, sits on a 0.06 acre lot. Features: 5 bedrooms, 5 bathrooms. It has been listed on Rocket Homes since March 28, 2025 and is currently priced at $1,395,500.
Between March and April 2025, Chestertown, MD real estate market has seen increase in the number of listings by 68.4%. In April 2025, listings were on the market for 70 days. During the same period, the median list price in this real estate market was $419,500.
From Rocket Homes Real Estate and based on county public records data.