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329 HIGH Street
CHESTERTOWN MD 21620 US

$1,250,000

Active Listing ID MDKE2005172
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Lot: 0.09 Acres
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$1,250,000

Active Listing ID MDKE2005172
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329 HIGH Street 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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Property Features

  • Facts
  • Lot Size: 0.09 Acres
  • Property Type: Other
  • Property Sub-type: Other
  • Features
  • Cooling System: Central Air, Heat Pump
  • Heating Fuels: Heat Pump (Heating)

Property

  • propertytype: Other
  • propertysubtype: Other
  • listprice: 1250000
  • unparsedaddress: 329 HIGH Street
  • postalcity: CHESTERTOWN
  • stateorprovince: MD
  • country: US
  • postalcode: 21620
  • bathroomsfull: 0
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.09
  • lotsizeunits: Acres
  • lotsizearea: 0.09
  • livingarea: 0
  • livingareaunits: Square Feet
  • latitude: 39.20952
  • longitude: -76.06754
  • listagentfullname: Richard Keaveney
  • listagentemail: rdkeaveney@gmail.com
  • listagentkey: 3yd-TRENDPA-3107913
  • listagentmlsid: 3107913
  • listagentpreferredphone: 4107086470
  • listagentofficephone: 4107086470
  • listofficekey: 3yd-TRENDPA-CROS1
  • listagentstatelicense: 662142
  • listofficemlsid: CROS1
  • disclaimer: Copyright © 2025 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: TRENDPA
  • yearbuilt: 1880
  • listingcontractdate: 2025-05-09
  • listagenturl: https://csrealtors.com/
  • countyorparish: KENT
  • elementaryschooldistrict: KENT COUNTY PUBLIC SCHOOLS
  • middleorjuniorschooldistrict: KENT COUNTY PUBLIC SCHOOLS
  • highschooldistrict: KENT COUNTY PUBLIC SCHOOLS
  • cooling: Heat Pump, Central Air
  • constructionmaterials: Brick
  • heating: Heat Pump (Heating)
  • numberofunitstotal: 2
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 6
  • parkingfeatures: Parking Lot
  • waterfrontyn: False
  • franchiseaffiliation: None
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -76.06754, 39.20952
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Cross St Realtors", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"rdkeaveney@gmail.com", "ListBrokerageCity":"Chestertown", "ListBrokerageCountry":"US", "ListBrokerageEmail":"stacy@csrealtors.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"Cross St Realtors", "ListBrokeragePhone":"(410) 778-3779", "ListBrokeragePostalCode":"21620", "ListBrokerageStateOrProvince":"MD", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"201 S Cross St", "ListBrokerageWebsiteUrl":"https://csrealtors.com/", "ListOfficeAddress1":"201 S CROSS Street ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"CROS1", "ListOfficeCity":"CHESTERTOWN", "ListOfficeCountry":"USA", "ListOfficeEmail":"stacy@csrealtors.com", "ListOfficePostalCode":"21620", "ListOfficeStateOrProvince":"MD", "ListPriceCurrencyType":"USD", "ListingTitle":"Commercial Sale - CHESTERTOWN, MD", "ListingURL":null, "MLSModificationTimestamp":"2025-08-18 20:18:29", "Neighborhoods":[], "PostalCode":null, "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":7011, "TaxDescription":null, "TaxYear":null}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 10/2/2025 10:18:42 PM GMT
Source Updated Date: 12/7/2025 12:56:07 PM GMT

Courtesy of: Richard Keaveney, Cross Street Realtors LLC, rdkeaveney@gmail.com

Copyright © 2025 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.