200 High Street Chestertown, MD $ 2,300,000
200 High Street
$ 2,300,000
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200 High Street

Chestertown, MD, 21620
$ 2,300,000
Bedrooms-- Baths-- Sq 6,918

Monthly Estimate*

$ 14,161

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Commercial Property for sale in Chestertown, MD

for $2,300,000. This 6,918 square foot building was built in 1860 on a lot size of 0.14.

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.

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Commercial Active

Price

$ 2,300,000

Property Type

Commercial

Taxes

$ 8,359

Style

Apartment Building

Lot Size

0.14

Year Built

1860

Town/City

Chestertown

County/Region

Kent

MLS | Web ID

MDKE2006092

Features
Interior
Heating Fuel Electric
Flooring Laminate Plank
Hot Water Electric
Heating Y/N Y
Central Air Y/N Y
Total Restrooms 9
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General
Sewer Public Sewer
Heating Heat Pump - Electric BackUp Programmable Thermostat
Cooling Central A/C Ductless/Mini-Split Energy Star Cooling System Heat Pump(s) Multi Units Programmable Thermostat
Possession Negotiable
Roof Architectural Shingle Asphalt Rubber Shake
Zoning C2
Security Features Fire Detection System Monitored Smoke Detector
Construction Materials Advanced Framing Combination Spray Foam Insulation Wood Siding HardiPlank Type
Year Built 1860
Property Subtype Five Or More Units
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Business Type Apartment Building
Accessibility None
County KENT
New Construction N
Property Type Commercial Sale
Energy Efficient Appliances HVAC Incentives
Subdivision Name DOWNTOWN CHESTERTOWN
Possible Use Apartment Building Apartments Barber/Beauty Commercial Day Care Flex Space Investment Liquor Store Mixed Use Multi-Family Office Professional Service Residential Retail Spa Other
Water Access Y/N N
Status ACTIVE
Directions Located on the corner of High St and Queen St in Chestertown
City CHESTERTOWN
Lot Size Units Square Feet
Lot Size Square Feet 6098.00
Tax Annual Amount 8359.0
Property Condition Excellent
Price Per Sq Ft Total AG 332.47
Acceptable Financing Bank Portfolio Cash Conventional
Historic Y/N Y
Lease Considered Y/N N
Vacation Rental Y/N N
Location Type Downtown
Standard Status Active
Year Built Source Estimated
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Exterior
Parking Features Private Surface
Lot Features Corner
Water Source Public
Type of Parking Off Site
Water View Y/N N
Building Area Total 6918.00
Lot Size Acres 0.14
Lot Size Source Estimated
Waterfront Y/N N
Land Assessed Value 300000.00
Navigable Water Y/N N
Water Oriented Y/N N
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Internal Only
Street Number 1 200
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* Excluded Features
List By
Taylor Properties

Broker

santobonire@gmail.com

Email

Affordability Calculator

$14,858
Per Month
95%
5%
0%
Monthly Principal & Interest
$14,161
Monthly Property Taxes
$697
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
2136830 Elementary School
2137124 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
1/29/2026$2,300,000 Listed Price

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200 High Street, Chestertown, MD, 21620 is a Commercial Property for sale at $2,300,000 with 6,918 sqft and a lot size of 0.14. 200 High Street was built in 1860. The property's zip code is 21620 which is in Chestertown, MD