349 High St
Description
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,...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 business 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. See updated zoning info from the town in documents
- Listed by Cheryl Hurt • Coldwell Banker Chesapeake Real Estate CompanyP: (619)-755-7730 cherylh@cbchesapeake.com
Property Details for 349 High Street
Property Details for 349 High Street
| Status | Active Under Contract |
|---|---|
| MLS # | MDKE2004076 |
| Days on Market | 453 |
| Taxes | $5,442 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Compass Type | Townhouse |
| MLS Type | Residential / Fee Simple |
| Year Built | 1900 |
| Lot Size | 0.13 AC / 5,737 SF |
| County | Kent County |
Location
Building Information for 349 High Street
Payment Calculator
$2,379 per month
30 year fixed, 6.15% Interest
$1,925
$454
$0
Property Information for 349 High Street
- In City Limits: Yes
- School District Name: KENT COUNTY PUBLIC SCHOOLS
- School District County ID: 121139164602
- SchoolDistrictSource: Listing Agent
- County: KENT
- Water View: No
- Water Access: No
- Water Oriented: No
- Navigable Water: No
- Tidal Water: No
- Riparian Rights Y/N: No
- Property Manager Y/N: No
- Senior Community: No
- Tax Year: 2024
- Tax Assessed Value: $347,267
- Year Assessed: 2024
- County Tax: $3,938
- Improvement Assessed Value: $121,300
- City Town Tax: $1,504
- Land Assessed Value: $203,700
- Clean Green Assessed: No
- Land Use Code: R
- Zoning: RB PROFESSIONAL OFFICE
- Zoning Dscrp: See attached relevant section of zoning ordinance.
- Automatically Update Tax Values Y/N: Yes
- TaxDataUpdatedYN: No
- Pets Allowed: Yes
- Pet Restrictions: No Pet Restrictions
- # Bedrooms Count Main Level: 1
- # Bathrooms Count Main Level: 2
- # Bathrooms Full Main Level: 1
- # Bathrooms Half Main Level: 1
- # Bedrooms Count All Upper Levels: 6
- # Bathrooms Count All Upper Levels: 2
- # Bathrooms Full All Upper Levels: 2
- # Bathrooms Half All Upper Levels: 0
- # Bedrooms Count Upper Level: 4
- # Bathrooms Count Upper Level: 2
- # Bathrooms Full Upper Level: 2
- # Bathrooms Half Upper Level: 0
- # Bedrooms Count Upper Level: 2
- # Bathrooms Count Upper Level: 0
- # Bathrooms Full Upper Level: 0
- # Bathrooms Half Upper Level: 0
- Stories: Main, Upper 1, Upper 2
- Total Finished SQFT: 3,664.00
- Total Finished SQFT Source: Assessor
- Tax Total Finished SQFT: 3,664.00
- Total SQFT: 3,664.00
- Total SQFT Source: Assessor
- Construction Materials: Frame
- Foundation Details: Pillar/Post/Pier
- Room and Floor: Bedrooms-Main Level-1, Bathrooms Full-Main Level-1, Bathrooms Half-Main Level-1, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bedrooms-Upper Level 1-4, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2, Bedrooms-Upper Level 2-1, Bedrooms-Upper Level 2-2
- # Bathrooms Full: 3
- # Bathrooms Half: 1
- Other Structure: Above Grade, Below Grade
- Lot Size Source: Assessor
- Parcel ID: 4504651
- Ground Rent Exists: No
- Type Of Parking: On Street
- Fireplace: No
- Accessibility Features: None
- Spa: No
- Pool: No Pool
- Horse: No
- Heating: Yes
- Cooling Type: Window Unit(s)
- Cooling Fuel: Electric
- Heating Type: Radiator
- Heating Fuel: Oil
- Hot Water: Electric
- Water Source: Public
- Sewer Septic: Public Sewer
- List Agent AOR: Bay Area Association of REALTORS
Property History for 349 High Street
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Aug 29, 2025 | Active Under Contract BRIGHT #MDKE2003720 | — | |
| Aug 29, 2025 | Active Under Contract BRIGHT #MDKE2004076 | — | |
| Mar 10, 2025 | Price Change BRIGHT #MDKE2003720 | $395,000 | — |
| Mar 10, 2025 | Price Change BRIGHT #MDKE2004076 | $395,000 | — |
| Jun 3, 2024 | Listed (Active) BRIGHT #MDKE2004076 | $425,000 | — |
| Apr 19, 2024 | Listed (Active) BRIGHT #MDKE2003720 | $425,000 | — |
| Oct 23, 2007 | Closed (Public Record) Public Record #231421931 | $206,250 | — |
| Date | Event & Source | Price |
|---|---|---|
| 08/29/2025 | Active Under Contract BRIGHT #MDKE2003720 | — |
| 08/29/2025 | Active Under Contract BRIGHT #MDKE2004076 | — |
| 03/10/2025 | Price Change BRIGHT #MDKE2003720 | $395,000 |
| 03/10/2025 | Price Change BRIGHT #MDKE2004076 | $395,000 |
| 06/03/2024 | Listed (Active) BRIGHT #MDKE2004076 | $425,000 |
| 04/19/2024 | Listed (Active) BRIGHT #MDKE2003720 | $425,000 |
| 10/23/2007 | Closed (Public Record) Public Record #231421931 | $206,250 |
For completeness, Compass often displays two records for one sale: the MLS record and the public record.
Public Records for 349 High Street
Schools near 349 High Street
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 | |||
| Public - | PK to 5 |
Rating | School | Distance |
|---|---|---|
H. H. Garnett Elementary School PublicPK to 5 | ||
Kent County Middle School Public6 to 8 | ||
Kent County High School Public9 to 12 | ||
Worton Elementary School PublicPK to 5 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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Listing Courtesy of Coldwell Banker Chesapeake Real Estate Company
© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 12/09/2025 10:51 AM