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$1,190,000
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Property Description
Seller MAY consider partial financing. Seller MAY also consider a five-year lease for first floor retail space (2400 square feet +/-), subject to qualifications. 329 High Street | Chestertown, Maryland A Landmark Reinvented | Circa 1880 Designed by renowned local architect Walter Pippen, 329 High Street is a masterfully restored piece of Chestertown's architectural heritage. Pippen, whose work helped shape the town's historic identity, imbued this structure with timeless character that now meets modern-day performance. HISTORIC SOUL. MODERN BACKBONE. PRIME LOCATION. Mixed-Use Potential - 2,400 SF Commercial Space (Main Level) - 1,600 SF Luxury 3BD / 2.5BA Apartment (Upper Level) - 3 Separate Entrances + Ample Parking Turnkey Infrastructure - 650 AMP Electric Service - New Water Main - Fire Suppression System - New HVAC + Roof Restored with Intention - Custom Mahogany Facade & Windows - Repointed Brick with Lime Mortar - High-End, Energy-Efficient Finishes Throughout POTENTIAL USES INCLUDE: Culinary Studio Chef's Table Experience Farm to Fork Bistro Seasonal Tasting Room Culinary Collective Pop-up Restaurant Space Shared Commercial Kitchen Food Incubator Artisan Bakehouse Morning Loaf & Latte Bar Elevated Botanical Apothecary Holistic Herb & Remedy Studio Custom Cobbler Boutique Private Practice with Character Tech/Media Studio Chestertown, MD; nestled along the Chester River, Chestertown is a vibrant waterfront community steeped in colonial history, cultural richness, and artistic spirit.
Full Property Details
Full Property Details for 329 High St
General
- Price: $1,190,000
- Taxes: $7,011 (2024)
- Status: Active
- Type: Commercial Institutional
- Source: BrightMLSMidAtlantic
- MLS ID: MDKE2005172
- Updated: 3/6/2026
- Added to Site: 345 day(s) ago
Business
- Business Type: Restaurant/Bar, Hair Salon and Spa, Health Club, Othe
Interior
- Flooring: Wood, Concrete
Parking
- Total Spaces: 6
- Parking Features: Private
- Parking Type: Parking Lot
Location
- Municipality: Chestertown
- County: KENT
- Driving Directions: GPS Downtown Chestertown, High Street
- Location Details: Business District
- Historic District: Yes
- City Limits: Yes
Heating & Cooling
- Central air: Yes
- Cooling Type: Heat Pump(s), Central A/C
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Electric
- Water Heater: Other
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Electric Available
Structural Information
- Construction: Brick
- Roof: Metal, Rubber, Other, Wood
- Building Size: 4500
- Year Built: 1880
- Year Built Source: Assessor
- Property Condition: Excellent
Unit Information
- # Tenants: Multiple
Lot Features
- Property View: Street
- Lot Size (Acres): 0.09
- Lot Size (Sq. Ft.): 3,996
- Lot Size Source: Assessor
- Zoning: C-2
- Lot Description: Premium
Financial Considerations
- Price Per Sq. Ft.: $264.44
- Assessment Year: 2025
- City/TownTax: $1,937
- City/TownTax Freq: Annually
- County Tax: $5,073
- County Tax Freq: Annually
- Tax w/Assessment: $454,833
- Tax Amount: $7,011
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Investment: Yes
Listed by Cross Street Realtors LLC, Richard Keaveney
Get Pre-Approved Today
Schools
Schools serving 329 High St
School District:Kent County Public Schools
| Name | Grades | Distance |
|---|---|---|
H. H. Garnett Elementary School 320 Calvert Street, Chestertown, MD 21620 | PK-5 | 0.3 mi |
Kent County Middle School 402 East Campus Avenue, Chestertown, MD 21620 | 6-8 | 0.7 mi |
Kent County High School 25301 Lambs Meadow Road, Worton, MD 21678 | 9-12 | 5.4 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 329 High St
Date
Details
Price
Change
Source
1/27/2026
Price Reduced
$1,190,000
-4.8%
MLS
6/20/2025
Price Increased
$1,250,000
4.17%
MLS
5/09/2025
Listed
$1,200,000
380%
MLS
12/13/2019
Sold
$250,000
—
Public Record
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
Tax History for 329 High St
Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,128
2%
$454,833
2%
2024
$7,011
89%
$447,367
2%
2023
$3,709
—
$439,900
85%
2022
$3,709
—
$238,167
—
2020
$3,725
—
$237,933
—
2021
$3,725
—
$237,700
—
2020
$3,718
1%
$237,700
—
2019
$3,694
2%
$237,700
-1%
2018
$3,622
—
$240,800
—
2017
$3,622
307%
$240,800
—
2016
$891
-77%
$240,900
-7%
2015
$3,882
100%
$258,100
—
2014
$1,941
—
$258,100
—
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
Estimate the Cost for 329 High St
329 High Street, Chestertown, MD 21620 (MLS# MDKE2005172) is a Commercial Institutional property. 329 High Street is currently listed for $1,190,000 and was received on May 09, 2025. Want to learn more about 329 High Street? Do you have questions about finding other Commercial Institutional real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.

