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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.
Location
Listed By
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Listing information provided courtesy of the Bright MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable, but is not guaranteed accurate by the MLS. Updated: 10th March, 2026 8:34 PM (UTC)
Listing Agent: Richard Keaveney
Listing Office: Cross Street Realtors LLC
Attribution contact: 4107086470

































