$395,000
UNDER CONTRACT

349 & 351 High St Chestertown, MD 21620

Estimated payment $2,602/month

Total Views 34,418
-- Bed
-- Bath
3,664 Sq Ft
$108 Price per Sq Ft

Highlights

  • Victorian Architecture
  • Tankless Water Heater
  • 1-minute walk to Fountain Park
  • 1 Fireplace
  • Radiator

About This Home

A Rare Opportunity in the Heart of Historic Chestertown

Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.

Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.

That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.

Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and commercial uses—making it an ideal candidate for those looking to merge lifestyle, business, and history.

Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.

Schedule your showing today and imagine the future you can build here.

Listing Agent

Cheryl Hurt

Coldwell Banker Chesapeake Real Estate Company License #676679 Listed on: 04/19/2024

Coldwell Banker Chesapeake Real Estate Company

Property Details

Home Type

  • Multi-Family

Est. Annual Taxes

  • $5,442

Year Built

  • Built in 1900

Lot Details

  • 5,737 Sq Ft Lot

Parking

  • On-Street Parking

Home Design

  • Duplex
  • Victorian Architecture
  • Frame Construction
  • Piling Construction

Interior Spaces

  • 3,664 Sq Ft Home
  • 1 Fireplace

Utilities

  • Window Unit Cooling System
  • Radiator
  • Heating System Uses Oil
  • Tankless Water Heater

Community Details

  • 2 Units
  • 3-Story Building

Listing and Financial Details

  • Assessor Parcel Number 1504006259

Property Details

Home Type

Multi-Family

Est. Annual Taxes

$5,442

Year Built

Built in 1900

Lot Details

0

Listing Details

  • Property Type: Multi-Family
  • Property Sub Type: Duplex
  • Structure Type: End Of Row/Townhouse
  • Architectural Style: Victorian
  • Ownership: Fee Simple
  • Historic: No
  • New Construction: No
  • Expected On Market: 4/19/2024 12:00:00 AM
  • Year Built: 1900
  • Automatically Close On Close Date: No
  • Building Winterized: No
  • Remarks Public: A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself. That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project. Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and commercial uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often. Schedule your showing today and imagine the future you can build here.
  • Special Features: UnderContract

Interior Features

  • Fireplaces Count: 1
  • Fireplace: Yes
  • Foundation Details: Pilings
  • Room Count: 17
  • Basement: No
  • Total Sq Ft: 3664
  • Living Area Sq Ft: 3664
  • Price Per Sq Ft: 107.81
  • Above Grade Finished Sq Ft: 3664
  • Above Grade Finished Area Units: Square Feet
  • Street Number Modifier: 349 & 351

Exterior Features

  • Other Structures: Above Grade, Below Grade
  • Construction Materials: Frame
  • Spa: No
  • Water Access: No
  • Waterfront: No
  • Water Oriented: No
  • Pool: No Pool
  • Tidal Water: No
  • Water View: No

Garage/Parking

  • Garage: No
  • Type Of Parking: On Street

Utilities

  • Central Air Conditioning: No
  • Cooling Fuel: Electric
  • Cooling Type: Window Unit(s)
  • Heating Fuel: Oil
  • Heating Type: Radiator
  • Heating: Yes
  • Hot Water: Tankless
  • Sewer/Septic System: Public Sewer
  • Water Source: Public

Condo/Co-op/Association

  • Association Recreation Fee: No

Schools

  • School District: KENT COUNTY PUBLIC SCHOOLS
  • School District Key: 121139164602
  • School District Source: Listing Agent

Lot Info

  • Land Use Code: R
  • Lot Size Acres: 0.13
  • Lot Size Units: Square Feet
  • Lot Sq Ft: 5737.00
  • Year Assessed: 2024
  • Zoning: C-2
  • In City Limits: Yes

Rental Info

  • Ground Rent Exists: No
  • Rent Control: No
  • Vacation Rental: No

Tax Info

  • Tax Annual Amount: 5442.00
  • Assessor Parcel Number: 1504006259
  • Tax Total Finished Sq Ft: 3664
  • County Tax Payment Frequency: Annually
  • Tax Data Updated: No
  • Tax Year: 2024

MLS Schools

  • School District Name: KENT COUNTY PUBLIC SCHOOLS

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Property History

Date Event Price Change Sq Ft Price
03/10/2025 03/10/25 Price Changed $395,000 -7.1% $108 / Sq Ft
04/19/2024 04/19/24 For Sale $425,000 -- $116 / Sq Ft
Source: Bright MLS

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Source: Bright MLS

MLS Number: MDKE2003720

Bright MLS
Maryland Kent County Chestertown 21620

349 & 351 High St, Chestertown, MD

This home is located at 349 & 351 High St, Chestertown, MD 21620 and is currently priced at $395,000, approximately $107 per square foot. This property was built in 1900. 349 & 351 High St is a home located in Kent County with nearby schools including Kent County Middle School, Kent County High School, and Chestertown Christian Academy.

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Cheryl Hurt
Listing Agent
Cheryl Hurt
Section Image
Coldwell Banker Chesapeake Real Estate Company
(619) 755-7730