200 High Street, CHESTERTOWN, MD 21620 (MLS # MDKE2006092)
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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 |
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| Year Built | 1860 | County | KENT |
SCHOOLS
| School District | KENT COUNTY PUBLIC SCHOOLS |
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Additional Details
| AIR | Central Air, Ductless, Electric, ENERGY STAR Qualified Equipment, Heat Pump, Multi Units |
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| 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
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Listing provided by Taylor Properties
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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.
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.