Connect

Find us on...

Dashboard

Marjorie Dick Stuart

  • Cell 240-731-8079
Questions?

105 High St, CHESTERTOWN, MD – $1,395,500

  • 5 Beds
  • Baths
  • 3,243 Sqft
  • .06 Acres
  • 5 Beds
  • Baths
  • 3,243 Sqft
  • .06 Acres

105 High St

***Photos reflect the progress as of 3 months ago. The property is now nearly completed and is simply awaiting a finishing coat of paint and a layer of sod on the newly fenced in rear yard. A superb level of craftsmanship and scope of work not to be missed.*** Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored legacy home on Chestertown Historic District’s most prominent corner. Water views are appreciated from two sides. Great balance of modern amenities and layout matched with historic design elements and style. The builders who took on this passion project are some of the most renowned in Kent County. 30 day estimated timeframe to complete upon contract acceptance. The detached garage is a huge plus with highly sought after off street parking.

Essential Information

  • MLS® #MDKE2005002
  • Price$1,395,500
  • Bedrooms5
  • Bathrooms4.50
  • Full Baths4
  • Half Baths1
  • Square Footage3,243
  • Acres0.06
  • Year Built1863
  • TypeResidential
  • Sub-TypeDetached
  • StyleVictorian
  • StatusActive

Community Information

  • Address105 High St
  • SubdivisionCHESTERTOWN HISTORIC DISTRICT
  • CityCHESTERTOWN
  • CountyKENT-MD
  • StateMD
  • MunicipalityChestertown
  • Zip Code21620

Amenities

  • # of Garages1
  • GaragesGarage - Side Entry
  • ViewWater, Scenic Vista, River

Interior

  • HeatingHeat Pump(s)
  • CoolingCentral A/C
  • Has BasementYes
  • BasementImproved, Interior Access
  • FireplaceYes
  • # of Fireplaces2
  • # of Stories4
  • Stories4

Exterior

  • ExteriorFrame
  • Exterior FeaturesPorch(es), Patio
  • FoundationPermanent

School Information

  • DistrictKENT COUNTY PUBLIC SCHOOLS

Additional Information

  • Date ListedMarch 28th, 2025
  • Days on Market178
  • ZoningR-3

Listing Details

Office

Coldwell Banker Chesapeake Real Estate Company

Please provide a valid email address.

Price Change History for 105 High St, CHESTERTOWN, MD (MLS® #MDKE2005002)

Date Details Price Change
Price Increased (from $1,395,000) $1,395,500 $500 (0.04%)

© 2020 BRIGHT, All Rights Reserved. Information deemed reliable but not guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Coldwell Banker Residential Realty participates, and is provided by BRIGHT through a licensing agreement. Real estate listings held by brokerage firms other than Coldwell Banker Residential Realty are marked with the IDX logo and detailed information about each listing includes the name of the listing broker.The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller.

Listing information last updated on September 21st, 2025 at 10:30am CDT.