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$289,900

  • For Sale
  • Under Contract
  • Single Family
  • 2 Beds
  • 3 Full Baths
  • 1,518 Sq. Ft.
  • Updated 12 days ago
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✨ Historic Charm in the Heart of Downtown Chestertown ✨ 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. 🏡✨

Full Property Details for 522 High St

General

  • Price: $289,900
  • Taxes: $4,636 (2025)
  • Status: Under Contract
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDKE2006614
  • Updated: 8/18/2026
  • Added to Site: 93 day(s) ago

Interior

  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Gas/Propane
  • Flooring: Wood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 1
  • Main - Full Baths: 1

Bedrooms

  • Total Bedrooms: 2
  • Bedrooms Upper: 2

Other Rooms

  • Laundry: Dryer In Unit, Washer In Unit

Parking

  • Parking Type: On Street

Location

  • Municipality: Chestertown
  • County: KENT
  • Subdivision: CHESTERTOWN HISTORIC DISTRICT
  • Driving Directions: West on High St, property will be on the left side, - East on High St, property is on the right side
  • Historic District: Yes
  • City Limits: Yes

School Information

  • School District: Kent County Public Schools

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Baseboard - Hot Water
  • Heating Fuel: Propane - Owned
  • Water Heater: Tankless

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Federal
  • Structure Type: Detached
  • Construction: Brick
  • Foundation: Brick/Mortar
  • Roof: Architectural Shingle
  • Stories Description: Main, Upper 1
  • Square Feet: 1,518
  • Sq. Ft. Source: Assessor
  • Living Area: 1,518 Sq. Ft.
  • Finished Above Grnd: 1,518 Sq. Ft.
  • Year Built: 1820
  • Year Built Source: Assessor

Lot Features

  • Lot Size (Acres): 0.08
  • Lot Size (Sq. Ft.): 3,640
  • Lot Size Source: Assessor
  • Zoning: R-5

Financial Considerations

  • Price Per Sq. Ft.: $190.97
  • Assessment Year: 2026
  • City/TownTax: $1,281
  • City/TownTax Freq: Annually
  • County Tax: $3,354
  • County Tax Freq: Annually
  • Tax w/Assessment: $302,433
  • Tax Amount: $4,636
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 1518

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Benson & Mangold, LLC, Taylor Leaverton

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Listing agent

— 522 High St —

  • Taylor Leaverton

    Benson & Mangold, LLC

Listing Office Email: info@bensonandmangold.com

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 522 High St

School District:Kent County Public Schools
NameGradesDistance
H. H. Garnett Elementary School
320 Calvert Street, Chestertown, MD 21620
PK-50.1 mi
Kent County Middle School
402 East Campus Avenue, Chestertown, MD 21620
6-80.6 mi
Kent County High School
25301 Lambs Meadow Road, Worton, MD 21678
9-125.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 522 High St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/14/2026
Price Reduced
$289,900
-7.97%
MLS
8/06/2026
Price Reduced
$315,000
-10%
MLS
7/13/2026
Price Reduced
$350,000
-12.48%
MLS
6/28/2026
Price Reduced
$399,900
-5.91%
MLS
6/13/2026
Price Reduced
$425,000
-5.56%
MLS
5/30/2026
Listed
$450,000
38.04%
MLS
1/31/2006
Sold
$326,000
—
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 522 High St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,636
—
$302,433
2%
2025
$4,636
4%
$295,800
4%
2024
$4,439
10%
$283,233
5%
2023
$4,019
—
$270,667
5%
2022
$4,019
1%
$258,100
1%
2020
$3,989
—
$256,300
1%
2021
$3,989
1%
$254,500
1%
2020
$3,952
3%
$252,700
—
2019
$3,832
8%
$252,700
—
2018
$3,546
5%
$252,700
—
2017
$3,390
331%
$252,700
—
2016
$787
-75%
$252,700
—
2015
$3,102
108%
$252,700
-7%
2014
$1,492
—
$272,800
—
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 522 High St

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

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NMLS#: 1598647

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Listed by Benson & Mangold, LLC, Taylor Leaverton

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522 High Street, Chestertown, MD 21620 (MLS# MDKE2006614) is a Single Family property with 2 bedrooms and 3 full bathrooms. 522 High Street is currently listed for $289,900 and was received on May 30, 2026. Want to learn more about 522 High Street? Do you have questions about finding other Single Family 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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