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200 High Street, Chestertown, MD 21620

$2,300,000
  • 200 High Street, Chestertown, MD 21620 Main Photo

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BEDS0 BATHS MLS#MDKE2006092
STATUSACTIVE PROPERTY TYPECommercial - SUBDIVISIONDOWNTOWN CHESTERTOWN SCHOOLKENT COUNTY PUBLIC SCHOOLS

Property Description

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.

200 High Street | MLS# MDKE2006092

This commercial property located at 200 High Street, Chestertown, MD 21620 is currently listed for sale with an asking price of $2,300,000. High Street is located within the KENT COUNTY PUBLIC SCHOOLS school district. Search Chestertown real estate on www.jessehershteam.com today.

Property Features

Property Type: Commercial -
Cooling: Central A/C, Ductless/Mini-Split, Energy Star Coolin
Fuel Type: Electric
Heating: Heat Pump - Electric BackUp, Programmable Thermosta
Lot Size: 0.14 Acres
Roof Type: Architectural Shingle, Asphalt, Rubber, Shake
Taxes: $8,359
Year Built: 1860

Feature Descriptions

Exterior: Advanced Framing, Combination, Spray Foam Insulation
Flooring: Laminate Plank
Location: Downtown
Lot: Corner
Lot Dimensions: 0.14 Acre(S)
Parking Notes: Private, Surface
Sewer: Public Sewer
Total Garage/Parking Spaces: 6
Water: Public

Local Schools

School District: KENT COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Taylor Properties
Agency Phone: 3019702447

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/04/2026. The listing information on this page last changed on 03/04/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 03/04/2026 12:00:05 AM EST) or Bright MLS (last updated Tue 03/03/2026 11:50:12 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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The Jesse Hersh Team
Jesse Hersh, Aimee Brossman, Tyler Mow 

215 S. Centerville Road, Lancaster, PA 17603
717-393-0100

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