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206 S Water St, 
Chestertown, MD 21620

$585,000

4

Beds

4

Baths

2,008

Sq Ft

Single Family

Active

Listed by

Thomas C Williams Jr.

, 

Monica S Molloy

Ttr Sotheby'S International Realty, chevychase@ttrsir.com

Last updated:

January 19, 2026, 02:48 PM

MLS#

MDKE2006058

Source:

BRIGHTMLS

About This Home

206 S Water St

Significant price reduction!!! Great value!! Live in the heart of Chestertown’s Historic District—see your boat from your front porch! Beautifully rebuilt and expanded, this versatile home offers 4 Bedrooms, 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a guest suite with walk-in closet and full bath. Upstairs, enjoy a second-story water view deck—built strong enough to support a hot tub or additional living area (double 2x8 joists per owner). Andersen composite dual-pane windows with plantation shutters offer energy efficiency and easy operation. Ample storage includes two walk-in closets plus a walk-in attic. Located on desirable Water Street, you’re just steps from the waterfront, Wilmer Park, shops, restaurants, bakeries, pubs, Farmer’s Market, arts district, and more. Cook and entertain in style with Heartland appliances and handcrafted cabinetry in the kitchen. 206 S. Water Street—a “feels-like-new” historic home in Chestertown’s most walkable location. Note The vacant lot next door is not part of this property. Separate owner.

Home Facts

Single Family

4 Baths

4 Bedrooms

Built in 1900

Price Summary

585,000

$291 per Sq. Ft.

MLS #:

MDKE2006058

Last Updated:

January 19, 2026, 02:48 PM

Added:

6 day(s) ago

Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

3

Interior

Living Area:

2,008 Sq. Ft.

Structure

Structure

Architectural Style:

Coastal, Colonial

Building Area:

2,008 Sq. Ft.

Year Built:

1900

Lot

Lot Size (Sq. Ft):

1,742

Finances & Disclosures

Finances

Price:

$585,000

Price per Sq. Ft:

$291 per Sq. Ft.

Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.