usm white logo

200204 High StreetChestertown, MD 21620Price: $2,300,000

  • Price: $2,300,000
  • 61 Days on Market
$
$
%
$/month over payments
Federal 30-year interest rate: 6.76% last updated on Sep 10, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
Active
200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620200204 High Street Chestertown MD 21620
QR Code
  • 0.14Acreage
  • 1860Year Built
  • DowntownLocationType
  • 332Price Per Square Foot
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, including new electric service, meters and new wiring throughout, all new plumbing using PEX, new water and septic service lines to the building, 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 50-year cedar roof was replaced in early 2000s), new 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/pilates studio recently moved into the third commercial space. 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.
Listed by Julie H SANTOBONI of Taylor Properties

Driving Directions

Railey Vacations
Railey Vacations
Office: 301-387-2124
5 Vacation Way
McHenry, MD 21541

More Info

Location Information

  • UsmAreaChestertown

Parking

  • Parking FeaturesPrivate, Surface
  • Parking TypesParking Lot

Basic Information

  • Date Listed07/15/2026

Building

  • Building Area SourceAssessor
  • Building Area Total6918
  • Construction MaterialsAdvanced Framing, Combination, HardiPlank Type, Spray Foam Insulation, Wood Siding
  • Total Garage And Parking Spaces6
  • Total Restrooms9
  • Year Built1860
  • Year Built Effective2022

Interior

  • FlooringLaminate Plank

Utilities

  • Central Air YNYes
  • CoolingCentral A/C, Ductless/Mini-Split, Energy Star Cooling System, Heat Pump(s), Multi Units, Programmable Thermostat
  • Cooling FuelElectric
  • Green Energy EfficientAppliances, HVAC, Incentives
  • Heat SystemHeat Pump - Electric BackUp, Programmable Thermostat
  • Heating FuelElectric
  • Heating YNYes
  • SewerPublic Sewer
  • Water HeaterElectric
  • Water SourcePublic

Basic Information

  • Broker NameTaylor Properties
  • List Price$2,300,000
  • LocationTypeDowntown
  • MLS NumberMDKE2006810
  • MLS Property TypeCommercial Sale
  • Price Per Square Foot332
  • Security FeaturesFire Detection System, Monitored, Smoke Detector
  • StatusACT
  • Units1

Property

  • Acreage0.14
  • Business TypeFlex
  • Lot DescriptionCorner
  • Lot Size SourceEstimated
  • Lot Size Square Feet6,000
  • New Construction YNN
  • Property ConditionExcellent
  • Property SubTypeFive Or More Units
  • ZoningC2
  • Zoning DescriptionC-2 zoning

Other

  • Historic YNYes
  • View Count49

Tax Information

  • Assessment Year2025
  • Tax Assessment Amount$829,900
  • Tax Year2025
  • Taxes$8,359
  • Total Taxes Payment FrequencyAnnually

Location

  • Address200204 High Street
  • Building Number200204
  • CountyKent
  • Cross StreetQueen St
  • DirectionsLocated on the corner of High St and Queen St in Chestertown
  • In City Limits YNYes
  • StateMD
  • SubdivisionDowntown Chestertown
  • TownChestertown
  • Zip21620

Exterior

  • RoofArchitectural Shingle, Asphalt, Rubber, Shake

Property Information

  • Municipal Trash YNYes

Ask A Question

Do not fill in this field:

I agree to receive marketing and customer service calls and text messages from Railey Vacations. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. 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 Railey Vacations 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.Data last updated September 14, 2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

I agree to receive marketing and customer service calls and text messages from Railey Vacations. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

$

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.