200 High Street, CHESTERTOWN, MD 21620 (MLS # MDKE2006092)

200 High Street, CHESTERTOWN, MD 21620 (MLS # MDKE2006092)


Price $2,300,000
Status Active
Size 6,918 sqft
Lot Size 6,099 sqft
Days on Market 0
A rare turnkey, profitable, investment property in downtown Chestertown. Renovated to the studs in 2022, 200-202-204 High Street has 5 apartments and 3 storefronts and since renovations has had no vacancies, with solid leases in place. During the renovations every major system in the building was replaced. Upgrades include new electric service, meters and new wiring throughout, all new plumbing using PEX, new energy efficient water heaters and appliances, rebuilt foundation, new Jeldwen Auralast windows, insulation and air sealing, new roof on rear portions of building (front cedar roof was replaced in early 2000s), new water and sewer lines and rear egress, a monitored fire alarm system and much more. Two of the storefronts are rented to a local arts non-profit and a yoga and pilates studio will be moving into the third commercial space in April. The 5 apartments consist of two 2-bedroom units and three 1-bedroom apartments. The steady income stream from the units is complemented by a generous property tax credit through 2032 (buyer to verify transferability). The property also has a Limited Lead-Free certificate, which requires only an exterior visual inspection every two years, and exempts the owner from MDE registration requirements. Complete income and expense information available after signing a confidentiality agreement. Limited photos posted for tenants' privacy. Contact for a private tour today. Please do not disrupt the businesses, they are tenants and the businesses are not part of the sale.
Property Type(s): Commercial
Last Updated 1/29/2026 Tract DOWNTOWN CHESTERTOWN
Year Built 1860 County KENT

SCHOOLS

School District KENT COUNTY PUBLIC SCHOOLS

Additional Details

AIR Central Air, Ductless, Electric, ENERGY STAR Qualified Equipment, Heat Pump, Multi Units
AIR CONDITIONING Yes
APPLIANCES Electric Water Heater
CONSTRUCTION HardiPlank Type, Spray Foam Insulation, Wood Siding
HEAT Electric, Heat Pump
LOT 6098 sq ft
LOT DESCRIPTION Corner Lot
PARKING Private, Off Site
SEWER Public Sewer
SUBDIVISION DOWNTOWN CHESTERTOWN
TAXES 8359
WATER Public
ZONING C-2 zoning

Location

 

Contact us about this Property

 / 
We respect your online privacy and will never spam you. By submitting this form with your telephone number you are consenting for Kevin Anselmi to contact you even if your name is on a Federal or State "Do not call List".

Listing provided by Taylor Properties
The multiple listing data appearing on this website, or contained in reports produced therefrom, comes in part from Metropolitan Regional Information Systems ("MRIS"). The information provided is for the viewer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the viewer may be interested in purchasing. All real estate listings include detailed information about them that includes the name of the listing brokers and therefore may reference real estate listing(s) held by a brokerage other than the broker and/or agent who owns this web site.

All listing data, including, but not limited to, square footage and lot size is believed to be accurate, but the listing agent, listing broker and respective Multiple Listing Services and their affiliates do not warrant or guarantee such accuracy. Therefore, all data should be personally verified through personal inspection by and/or with the appropriate professionals. Listing data last updated 1/29/26 5:09 PM PST.

The listing information on this web site is from various brokers who participate in IDX.

Copyright 2026 MRIS. All rights reserved.

This IDX solution is (c) Diverse Solutions 2026.

Email a Friend