Patterson-Schwartz Real Estate349 High Street, Chestertown, MD 21620-1309 $395,000
Interior Sq. Ft: 3,664
Acreage: 0.13
Age:125 years
Style:
Victorian
Subdivision: Historic District Chestertown
Design/Type:
End of Row/Townhouse
Description
A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself. That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project. Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and commercial uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often. Schedule your showing today and imagine the future you can build here.
Home Assoc: No
Condo Assoc: No
Basement: N
Pool: No Pool
Features
Utilities
Radiator Heating, Oil, Window Unit(s) Cooling, Electric, Hot Water - Electric, Public Water, Public Sewer
Garage/Parking
On Street
Exterior
Pillar/Post/Pier Foundation, Frame Exterior
Select a school from the following list. Schools are grouped by school type.
The schools on this list are selected by their proximity of up to 5 miles to the property address.
Proximity does not guarantee enrollment eligibility. Please contact the school directly for more information on enrollment requirements.
* If there are more than 5 schools of any type within a close proximity, click on the button to see additional schools of that type near the search address.
Public Elementary (1 schools)
| School | District | Grades | Place | Distance |
|---|---|---|---|---|
| H. H. Garnett Elementary | Kent County Public Schools | Preschool–5 | Chestertown | 0.24 mi |
Public Middle (1 schools)
| School | District | Grades | Place | Distance |
|---|---|---|---|---|
| Kent County Middle School | Kent County Public Schools | 6–8 | Chestertown | 0.64 mi |
Private (5 schools)
| School | Grades | Place | Distance | |
|---|---|---|---|---|
| Chester River Adventist School | Seventh-Day Adventist | 1–8 | Chestertown | 0.34 mi |
| Chestertown Christian Academy | Baptist | Preschool–12 | Chestertown | 1.01 mi |
| Radcliffe Creek School | Nonsectarian | K–8 | Chestertown | 1.03 mi |
| Kent School | Nonsectarian | Preschool–8 | Chestertown | 3.27 mi |
| Friendship Montessori School | Nonsectarian | Preschool–K | Worton | 4.76 mi |
© 2025 LiveBy. All Rights Reserved.
This report is a detailed community overview for Chestertown (21620), Maryland.
Community Quick Facts
- Average travel time to work for people in this community: 25
- Average salary of people in this community: $45,273
Community Summary
- Population Density (ppl / mile): 96
- Household Size (ppl): 2.23
- Households w/ Children: 37%
Housing Inventory
- Owned: 3,311 (53.4%)
- Rented: 1,775 (28.6%)
- Vacant: 1,110 (17.9%)
- Total: 6,196
Population Demographics
The population of the community broken down by age group. The numbers at the top of each bar indicate the number of people in the age bracket below.
Climate and Weather
The Temperature chart displays average high and low values for January and July, and is designed to provide an indication of both seasonal and daily temperature variability. The Weather Risk Index indicates the calculated risk of each type of weather event occurring in the future. This risk is based on historical localized storm events and weather patterns. The national average for each type of weather event equals a score of 100, so a score of 200 would represent twice the risk as the national average, and a score of 50 would represent half the risk of the national average.
Temperature
Education
Highest Level of Education Attained
- Less than 9th Grade: 4.6%
- Some High School: 6.1%
- High School Graduate: 28.4%
- Some College: 16.5%
- Associate Degree: 5.8%
- Bachelor's Degree: 19.2%
- Graduate Degree: 19.4%
Income by dollar range
Median Income: $63,806
Fair Market Rents
The Fair Market Rents show average gross rent estimates based on figures provided by the U.S. Department of Housing and Urban Development (HUD).
- One Bedroom: $578
- Two Bedroom: $897
- Three Bedroom: $1,260
© 2025 LiveBy. All Rights Reserved.
Contact Information
Schedule an Appointment to See this Home
Request more information
or call me now at 302-429-4500
Listing Courtesy of: Coldwell Banker Chesapeake Real Estate Company
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 Patterson-Schwartz Real Estate 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.
Information Deemed Reliable But Not Guaranteed.
Copyright BRIGHT, All Rights Reserved
Listing data as of 6/11/2025.
Broker Compensation
An offer of broker compensation or seller concession is not a guarantee. All compensation offers and concessions are negotiable and subject to written agreement between the parties. Please consult with your real estate agent for more information.
