329 High Street
Chestertown, MD 21620

$1,190,000

Beds: 0
Baths:
Sq. Feet: 0
MLS ID: MDKE2005172
Subdivision:
School Dist: KENT COUNTY PUBLIC SCHOOLS
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. View this listing at: http://tomboeshorerealtor.com/mls=MDKE2005172

Property Features

School Information

Printed March 03, 2026


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Licensed in Maryland
Thomas Boeshore 

100 Piney Narrows Road, Chester, MD 21619
443-589-8080