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$585,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,008 Sq. Ft.
  • Updated 2 days ago

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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.

Full Property Details for 206 S Water St

General

  • Price: $585,000
  • Taxes: $7,755 (2024)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDKE2006058
  • Updated: 1/14/2026
  • Added to Site: 3 day(s) ago

Interior

  • Interior Features: Breakfast Area, Crown Moldings, Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Island, Kitchen - Table Space, Primary Bath(s), Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Gas/Propane
  • Appliances: Dishwasher, Disposal, Dryer, Oven/Range - Electric, Washer/Dryer Stacked, Washer
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Upper 2 - Full Baths: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 2
  • Main - Full Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 3
  • Bedrooms-Up2: 1
  • Bedrooms Main & Up: 1

Other Rooms

  • Laundry: Main Floor

Exterior

  • Porch/Patio/Deck: Porch(es)

Parking

  • Parking Type: On Street

Location

  • Municipality: Chestertown
  • County: KENT
  • Subdivision: CHESTERTOWN HISTORIC DISTRICT
  • Driving Directions: Cross the Chester River Bridge, left on N Queen St, left on High St, right on S Water St to house on the right.
  • Historic District: Yes
  • City Limits: Yes

School Information

  • School District: Kent County Public Schools

Heating & Cooling

  • Cooling Type: Ductless/Mini-Split, Zoned
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric, Propane - Leased
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Colonial, Coastal
  • Structure Type: Detached
  • Construction: Frame
  • Foundation: Crawl Space
  • Stories Description: Main, Upper 1, Upper 2
  • Square Feet: 2,008
  • Sq. Ft. Source: Estimated
  • Living Area: 2,008 Sq. Ft.
  • Finished Above Grnd: 2,008 Sq. Ft.
  • Year Built: 1900
  • Year Built Source: Estimated
  • Property Condition: Excellent

Lot Features

  • Lot Size (Acres): 0.04
  • Lot Size (Sq. Ft.): 1,888
  • Lot Size Source: Estimated
  • Zoning: R-5

Water Features

  • Water Front Type: River
  • Water Front Name: Chester River

Financial Considerations

  • Price Per Sq. Ft.: $291.33
  • Assessment Year: 2025
  • City/TownTax: $2,143
  • City/TownTax Freq: Annually
  • County Tax: $5,611
  • County Tax Freq: Annually
  • Tax w/Assessment: $518,600
  • Tax Amount: $7,755
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple

Listed by TTR Sotheby's International Realty, Thomas C Williams Jr. and TTR Sotheby's International Realty, Monica S Molloy

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Listing agents

— 206 S Water St —

  • Thomas C Williams Jr.

    TTR Sotheby's International Realty

  • Monica S Molloy

    TTR Sotheby's International Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 206 S Water St

School District:Kent County Public Schools
NameGradesDistance
H. H. Garnett Elementary School
320 Calvert Street, Chestertown, MD 21620
PK-50.5 mi
Kent County Middle School
402 East Campus Avenue, Chestertown, MD 21620
6-80.8 mi
Kent County High School
25301 Lambs Meadow Road, Worton, MD 21678
9-125.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 206 S Water St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/14/2026
Listed
$585,000
82.81%
MLS
2/04/2016
Sold
$320,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 206 S Water St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,114
5%
$518,600
5%
2024
$7,729
11%
$494,800
5%
2023
$6,964
—
$471,000
5%
2022
$6,964
43%
$447,200
—
2020
$4,869
—
$447,200
44%
2021
$4,869
1%
$310,700
1%
2020
$4,834
1%
$309,100
—
2019
$4,803
3%
$309,100
—
2018
$4,649
-1%
$309,100
-1%
2017
$4,689
306%
$311,800
—
2016
$1,154
-75%
$311,800
—
2015
$4,689
-11%
$311,800
-11%
2014
$5,246
—
$348,800
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by TTR Sotheby's International Realty, Thomas C Williams Jr. and TTR Sotheby's International Realty, Monica S Molloy

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206 S Water Street, Chestertown, MD 21620 (MLS# MDKE2006058) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 206 S Water Street is currently listed for $585,000 and was received on January 14, 2026. Want to learn more about 206 S Water Street? Do you have questions about finding other Single Family real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.

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