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$2,300,000 Just Listed

  • For Sale
  • Active
  • Apartment
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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.

Full Property Details for 200 High St

General

  • Price: $2,300,000
  • Taxes: $8,359 (2025)
  • Status: Active
  • Type: Apartment
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDKE2006092
  • Updated: 1/29/2026
  • Added to Site: 1 day(s) ago

Business

  • Business Type: Apartment Building

Interior

  • Flooring: Laminate Plank

Rooms

Bathrooms

  • Restrooms: 9

Additional Information

  • Security/Safety: Fire Detection System, Monitored, Smoke Detector

Parking

  • Total Spaces: 6
  • Parking Features: Private, Surface
  • Parking Type: Off Site

Location

  • County: KENT
  • Subdivision: DOWNTOWN CHESTERTOWN
  • Cross Streets: Queen St
  • Driving Directions: Located on the corner of High St and Queen St in Chestertown
  • Location Details: Downtown
  • Historic District: Yes
  • City Limits: Yes

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Ductless/Mini-Split, Energy Star Cooling System, Heat Pump(s), Multi Units, Programmable Thermostat
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump - Electric BackUp, Programmable Thermostat
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Construction: Advanced Framing, Combination, Spray Foam Insulation, Wood Siding, HardiPlank Type
  • Roof: Architectural Shingle, Asphalt, Rubber, Shake
  • Building Size: 6918
  • Year Built: 1860
  • Year Built Source: Estimated
  • Property Condition: Excellent

Unit Information

  • # Tenants: Multiple
  • Other Units: Unit 1, Unit 1, Unit 1, Unit 1, Unit 1, Unit 1, Unit 1, Unit 1

Lot Features

  • Lot Size (Acres): 0.14
  • Lot Size (Sq. Ft.): 6,098
  • Lot Size Source: Estimated
  • Zoning: C2
  • Lot Description: Corner

Green Features

  • Energy Efficient: Appliances, HVAC, Incentives

Financial Considerations

  • Price Per Sq. Ft.: $332.47
  • Assessment Year: 2025
  • Tax w/Assessment: $829,900
  • Tax Amount: $8,359
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Investment: Yes

Listed by Taylor Properties, Julie H SANTOBONI

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Listing agent

— 200 High St —

  • Julie H SANTOBONI

    Taylor Properties

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 200 High St

School District:Kent County Public Schools
NameGradesDistance
H. H. Garnett Elementary School
320 Calvert Street, Chestertown, MD 21620
PK-50.4 mi
Kent County Middle School
402 East Campus Avenue, Chestertown, MD 21620
6-80.7 mi
Kent County High School
25301 Lambs Meadow Road, Worton, MD 21678
9-125.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 200 High St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/29/2026
Listed
$2,300,000
379.17%
MLS
8/28/2020
Sold
$480,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 200 High St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,348
-36%
$829,900
—
2024
$13,006
63%
$829,900
-7%
2023
$7,971
—
$893,400
75%
2022
$7,971
-1%
$511,900
—
2020
$8,071
—
$511,900
-1%
2021
$8,071
—
$515,000
—
2020
$8,055
1%
$515,000
—
2019
$8,003
3%
$515,000
—
2018
$7,749
—
$515,200
—
2017
$7,749
307%
$515,200
—
2016
$1,906
-78%
$515,200
-10%
2015
$8,564
100%
$569,400
—
2014
$4,282
—
$569,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 200 High St

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Taylor Properties, Julie H SANTOBONI

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200 High Street, Chestertown, MD 21620 (MLS# MDKE2006092) is a Apartment property. 200 High Street is currently listed for $2,300,000 and was received on January 29, 2026. Want to learn more about 200 High Street? Do you have questions about finding other Apartment real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.

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