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Berkshire Hathaway HomeServices Homesale Realty

+18003833535

329 High Street, Chestertown, MD 21620Asking Price of: $1,190,000

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Primary property photo for 329 High Street
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.
Scannable QR Code Link for 329 High Street property details

Photos for 329 High Street, Chestertown, MD 21620

+18003833535

Scannable QR Code Link for 329 High Street property details

Details for 329 High Street, Chestertown, MD 21620

+18003833535

Property Details

  • Address: 329 High Street, Chestertown, MD 21620
  • Bedrooms: 0
  • Area: Chestertown
  • School District: KENT COUNTY PUBLIC SCHOOLS
  • MLS ID: MDKE2005172
  • Status: ACTIVE

Property School Information

  • School District: KENT COUNTY PUBLIC SCHOOLS

Property Features

  • Taxes: $7,011
  • Roof Type: Metal,Rubber,Other,Wood
  • Exterior: Brick
  • Parking Notes: Private
  • Special View Info: Street
  • Lot Size: 0.09 Acres
  • Lot Dimensions: 0.09 Acre(S)
  • Heating: Heat Pump(s)
  • Fuel Type: Electric
  • Cooling: Heat Pump(s),Central A/C
  • Year Built: 1880
  • Water: Public
  • Sewer: Public Sewer
  • Units: 2
  • Municipality: Chestertown
  • Location Description: Business District
  • Lot Description: Premium
  • Total Garage/Parking Spaces: 6
  • Flooring: Wood,Concrete
  • Utilities: Electric Available




Property information as of Friday, April 17, 2026 at 10:51 PM America/New_York
Scannable QR Code Link for 329 High Street property details

Contact information for 329 High Street, Chestertown, MD 21620

+18003833535

Listed By

Agency Name: Cross Street Realtors LLC
Agency Phone: 4107783779

Shown By

Agency Title: Berkshire Hathaway HomeServices Homesale Realty
Agency Phone: +18003833535