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329 High St
For Sale $1,250,000
$1,250,000
- 2 Units
- Unknown Sq Ft
- 3,996 Sq Ft
- Unknown Cap Rate
Description
Own a Piece of the Legacy
reimagined for today’s entrepreneurs, creatives, & visionaries
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.
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Amenities
Garage
Pool
Garden
Security System
Internet
Telephone
Heating
Fireplace
Balcony & Patio
TV / Cable
Laundry
Hardwood Floors
Spa
Air Conditioning
Solar Power
Floor Plan
Great Views
Natural Light
Quiet
Water View
Elevator
Guest Unit(s)
Furnished
220 Volt
Property Details
| List Price | $1,250,000 |
| Property Type | Flex Space |
| Usable Sqft | Unknown |
| Number of Stories | 0 stories |
| Parking Spots | 0 spots |
| Year Built | 1880 |
| Last Sold | Unknown |
| Sold Price | Unknown |
| APN # | 1504014634 |
| MLS # | MDKE2005172 |
| Property ID | 321785683 |
| Lot Sqft | 3,996 |
| Zoning | C-2 |
| Total Units | 2 |
| Days on Market | 212 |
| Original List Price | Unknown |
| Date Updated | August 18, 2025 |
| Date Created | May 08, 2025 |
Financials not available online. Please inquire with your agent for more details.
Listing Provided By
Richard Keaveney an agent of . Lic #662142
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Data last updated: December 06, 2025.
Robert Crawford
REAL ESTATE AGENT