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206 S Water Street, Chestertown, MD 21620

$549,000
  • 206 S Water Street, Chestertown, MD 21620 Main Photo

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Contingent Price Reduced $36,000 on February 10th, 2026
BEDS4 BATHS3 full 1 partial SQUARE FEET2,008 MLS#MDKE2006058
STATUSACTIVE UNDER CONTRACT PROPERTY TYPEResidential - Single Family SUBDIVISIONCHESTERTOWN HISTORIC DISTRICT SCHOOLKENT COUNTY PUBLIC SCHOOLS

Property Description

Seller says sell! Massive price reduction ! Below market for this pristine home well situated in chestertown historic district! A rare Water Street opportunity—see your boat from the front porch and enjoy walkable waterfront living in Chestertown. This thoughtfully rebuilt historic home offers 4 bedrooms, 3.5 baths, flexible guest spaces, and a water-view deck built to support a hot tub. Perfect as a primary residence or low-maintenance Chesapeake pied-à-terre for DC, Baltimore, and Philadelphia weekenders. Quality finishes include Andersen composite windows with plantation shutters, Heartland appliances, handcrafted cabinetry, and excellent storage. Walk to parks, dining, shops, arts, and the harbor. Vacant lot next door is separately owned.

206 S Water Street | MLS# MDKE2006058

This single family home located at 206 S Water Street, Chestertown, MD 21620 is currently listed for sale with an asking price of $549,000. This property was built in 1900 and has 4 bedrooms and 3 full and 1 partial baths with 2008 sq. ft. S Water Street is located in the CHESTERTOWN HISTORIC DISTRICT subdivision within the KENT COUNTY PUBLIC SCHOOLS school district. Search CHESTERTOWN HISTORIC DISTRICT real estate on www.mikenelsonrealtor.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Ductless/Mini-Split, Zoned
Fireplaces: 1
Fuel Type: Electric, Propane - Leased
Heating: Heat Pump(s)
Home Style: Colonial, Coastal
Lot Size: 0.04 Acres
Stories: 3.0
Taxes: $7,755
Year Built: 1900

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Dishwasher, Disposal, Dryer, Oven/Range - Electric, Washer/Dryer Stacked, Washer
Exterior: Frame
Fireplace: Gas/Propane
Flooring: Hardwood
Interior: Breakfast Area, Crown Moldings, Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Island, Kitchen - Table Space, Primary Bath(s), Wood Floors
Lake Name: Chester River
Lot Dimensions: 0.04 Acre(S)
Municipality: Chestertown
Sewer: Public Sewer
SQFT Above Finished: 2008
SQFT Total Finished: 2008
Structure Type: Detached
Water: Public

Local Schools

School District: KENT COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: TTR Sotheby's International Realty
Agency Phone: 3019673344

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Estimated Payment

$ 2,028.21 per month $1,221.84 Principal & Interest $646.25 Property Tax $160.13 Homeowner's Insurance

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