522 HIGH STREETCHESTERTOWN, MD 21620

Single Family · 2 Beds · 3 Full Baths · 1,518 Sq. ft. | 0.08 Acres
$399,900 ACTIVE

522 HIGH STREET Overview

Time on Site:
31 days
Visits:
1

œ¨ Historic Charm in the Heart of Downtown Chestertown œ¨ Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dreamed of owning a piece of history; or the savvy investor looking for their next restoration project. Outside, escape to your own private backyard sanctuary complete with a brick patio, fountain, and peaceful garden setting, an unexpected retreat right in town. Please note that the home is currently furnished and filled with décor and personal property. All furniture, décor, and contents currently in the home will be auctioned prior to settlement and are not included in the sale unless otherwise agreed upon. If you've been waiting for the right historic home to make your own, this is your chance to bring new life to a true Chestertown treasure. 🏡œ¨

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522 HIGH STREET Facts & Features

  • Type Single Family
  • Sq. ft. 1,518
  • Price/Sq.ft. $263
  • Lot 0.08 Acres

Details

General

Association/HOA

  • Association: No
  • Condo/Coop Association: No

Listing Information

  • Real Estate Owned: No
  • Short Sale: No

Building Information

  • New Construction: No
  • Pool: No Pool
  • Total SQFT: 1518
  • Year Built: 1820

Location/Region

  • Country: US
  • County: KENT
  • County Or Parish: KENT
  • In City Limits: Yes
  • Subdivision Name: CHESTERTOWN HISTORIC DISTRICT

Parking Information

  • Type of Parking: On Street

Tax Information

  • City/Town Tax: 1281.00
  • City/Town Tax Payment Frequency: Annually
  • County Tax: 3354.00
  • County Tax Payment Frequency: Annually
  • Tax Annual Amount: $4,636.00
  • Tax Assessed Value: 302433.00
  • Tax Year: 2025

General Information

  • Historic: Yes
  • Property Type: Residential
  • School District Name: KENT COUNTY PUBLIC SCHOOLS
  • Senior Community: No
  • Special Listing Conditions: Standard
  • Vacation Rental: No
  • Year Assessed: 2026
  • Zoning: R-5

Interior

Building Information

  • Cooling Fuel: None
  • Heating Fuel: Propane - Owned

Parking Information

  • Garage: No

Beds/Baths

  • Bathrooms Full: 3
  • Bathrooms Full Main Level: 1
  • Bathrooms Total: 3
  • Bedrooms Total: 2

Building Exterior/Construction

  • Structure Type: Detached

Building Interior

  • Above Grade Finished Area: 1518
  • Above Grade Finished Area Source: Assessor
  • Above Grade Finished Area Units: Square Feet
  • Below Grade Finished Area: 0
  • Below Grade Finished Area Source: Assessor
  • Below Grade Finished Area Units: Square Feet
  • Central Air: No
  • Hot Water: Tankless
  • Laundry Type: Dryer In Unit,Washer In Unit

General Information

  • Accessibility Features: 2+ Access Exits
  • Basement: No
  • Cooling: None
  • Fireplace Features: Gas/Propane
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Wood
  • Foundation Details: Brick/Mortar
  • Levels: 2
  • Living Area: 1518
  • Living Area Source: Assessor
  • Main Level Bathrooms: 1.00

Exterior

Lot Information

  • Lot Size Source: Assessor
  • Lot Size Square Feet: 3640.00
  • Lot Size Units: Square Feet
  • Water Source: Public

Waterfront/View

  • Water Oriented: No
  • Water View: No
  • Waterfront: No

Building Exterior/Construction

  • Architectural Style: Federal
  • Construction Materials: Brick
  • Roof: Architectural Shingle

General Information

  • Other Structures: Above Grade,Below Grade
  • Sewer: Public Sewer
  • Water Access: No

522 HIGH STREET Neighborhood

Community

21620 (CHESTERTOWN) Demographics

41
Median Age
97
Population Density (per sq. mile)
48%
College Educated
$62,210
Estimated Median Income
3,408
Estimated Total Home Owners
1,835
Estimated Total Renters
65% / 35%
Estimated Owner / Renter Divide
2
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.
* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

522 HIGH STREET Market Data

Based on the last 30 days in this zip code

$612,560
Average List Price
$288
Average Price per Square Foot
19
Properties Sold
106
Average Days on Market
84
Properties for Sale
Calculations provided by Reliance Network

522 HIGH STREET History

Date Event Value Agent
6/28/2026Source: BRIGHT MLS Price Reduction
$399,900 -5.9%
6/13/2026Source: BRIGHT MLS Price Reduction
$425,000 -5.6%
5/30/2026Source: BRIGHT MLS Added to Database
May 30, 2026
Listing provided courtesy of Benson & Mangold, LLC- MLS# MDKE2006614MLS ProviderContact Information: [email protected] - 4108226665