$619,000

beds

baths

half bath

2,008

square ft

206 S Water Street

Chestertown, Maryland 21620

Active / MLS #MDKE2005840 / Single Family / Chestertown

Listing information updated 11/25/2025 at 4:41pm

Live in the heart of Chestertown's Historic District-see your boat from your front porch! Beautifully rebuilt and expanded, this versatile home offers 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 waterview 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.

Full Features

Architecture Style:

Colonial,Coastal

Beds Above Grade:

Cooling System:

Ductless/Mini-Split, Zoned

Heating System:

Heat Pump(s)

Appliances:

Dishwasher, Disposal, Dryer, Oven/Range - Electric, Washer/Dryer Stacked, Washer

Main Level Primary Bedroom:

Yes

Fireplace:

Yes

Pool:

Age:

125 Years

Water Front:

Square Feet:

2,008

Lot Size:

1888.00 Square Feet

Acreage:

0.04

Internal Features:

Breakfast Area, Crown Moldings, Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Island, Kitchen - Table Space, Primary Bath(s), Wood Floors

Taxes & Assessments

Tax Amount:

$7,755

Tax Year:

2024

Location

Zip Code:

21620

City:

Chestertown

County:

Kent

Schools

School District(s):

KENT COUNTY PUBLIC SCHOOLS

Elementary School:

N/A

Middle School:

N/A

High School:

N/A

Architecture Style:

Colonial,Coastal

Beds Above Grade:

Cooling System:

Ductless/Mini-Split, Zoned

Heating System:

Heat Pump(s)

Appliances:

Dishwasher, Disposal, Dryer, Oven/Range - Electric, Washer/Dryer Stacked, Washer

Main Level Primary Bedroom:

Yes

Fireplace:

Yes

Pool:

Age:

125 Years

Water Front:

Square Feet:

2,008

Lot Size:

1888.00 Square Feet

Acreage:

0.04

Internal Features:

Breakfast Area, Crown Moldings, Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Island, Kitchen - Table Space, Primary Bath(s), Wood Floors

Tax Amount:

$7,755

Tax Year:

2024

Zip Code:

21620

City:

Chestertown

County:

Kent

School District(s):

KENT COUNTY PUBLIC SCHOOLS

Elementary School:

N/A

Middle School:

N/A

High School:

N/A

Listing Office: TTR Sotheby's International Realty

Listing Office Phone: 301.967.3344

Disclaimer: 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, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information 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 the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2025 Bright MLS, Inc.