206 S Water Street, Chestertown, MD 21620-1534 $648,750

Beds/Baths: 4/3.1
Interior Sq. Ft: 2,008
Acreage: 0.04
Age:125 years
Style:
Coastal, Cottage
MLS#: MDKE2005362
Subdivision: Chestertown Historic District
Design/Type:
Detached

Description

Just in time for the annual Downrigging Festival! See tall ships sailing the Chester River from your front porch and live in the heart of Chestertown's thriving Historic District! This versatile home has over 2,000 square feet of finished living space and was rebuilt and expanded with future customizations in mind!* The rear addition includes a sunroom/mudroom with a separate entrance connecting to a spacious guest suite with a walk-in closet and full bath and an 18'x13' living area that is currently broken into 2 rooms: the wall between the bedroom and sitting room was wired to make wall removal simpler if you prefer one big room. If you like open spaces, remove the wall & it can be a spacious rear living room; great for both privacy & entertaining while still retaining its utility as a guest suite or a more open first floor master bedroom. As it is currently configured, you can utilize the separate entrance for a guest or open both doors to the rest of the home to make it part of your first floor living space without making any changes at all. A private outdoor entertaining area can be had in place of the large workshop if you prefer yard space. (Owner is willing to consider removal of the workshop) The second story deck and attic were solidly built with the structural support to hold a hot tub and/or finished living space. (With double 2x8 joists according to the owner!) Anderson composite dual pane windows custom fitted with planation shutters were installed throughout the home- all windows are easy to open & energy efficient. Imagine the possibilities here: Four baths: Three full baths and one powder room provide ultimate flexible living on all floors. Two walk-in closets and a walk-in attic provide LOTS of easily accessible storage in this "feels like new" quality home! Located at Chestertown Marina, 206 S Water Street has been extensively remodeled as recently as 2021. Live in the heart of it all & enjoy easy low maintenance living in the configuration you want. You'll be just steps from the waterfront and all Chestertown has to offer including the quiet calm of day to day life with a splash of occasional excitement from Festivals like Tea Party in Spring, Downrigging in Autumn, Dickens Festival in Winter, and the National Music Festival and Jazz Festival, both in Summertime! This desirable Water Street address provides easy walkable access to your boat, waterfront Wilmer Park (Jazz Fest!), restaurants, cozy pubs, artisan bakeries, Wine & Cheese, Farmer's Market at Fountain Park, Natural Food store, festival events, music, national art district, rail-trail, shops, live theater, and more. Walk everywhere! And when you come home with your Saturday Farmer's Market goodies, enjoy cooking on gorgeous electric Heartland appliances that compliment the hand crafted free-standing cabinetry in the kitchen. The sunroom/mudroom is fully insulated to allow open doors between the house and the rooms of the guest suite or lock the doors for complete separation & versatility. This home is adaptable to many ways of living! With bedrooms on every floor to be used as you like, the 3rd floor waterview suite with a full bath & a walk-in closet could just as easily be a den or a bunk room. The lawn next-door is under separate ownership & is not part of this sale. *Buyer to verify feasibility of any expansion plans. Centrally located for travel, your choice of BWI or Philadelphia International airports are just 90 minutes away. Explore the possibilities at 206 S Water St and imagine yourself here. It's a special place to live!

Bedroom 1: Upper 2
Living Room: Main
Kitchen: Main
In-Law/auPair/Suite: Main
Mud Room: Main

Taxes: $7,755
Home Assoc: No
Condo Assoc: No
Garage: N
Basement: N
Pool: No Pool
School Dist: Kent County Public Schools

Features

Water
Water Oriented: Yes; Water Front: No; Water Access: No; Water Body Name: Chester River; Water Body Type: River; Navigable: No;

Utilities
Heat Pump(s), Electric, Propane - Leased, Zoned Cooling, Ductless/Mini-Split, Electric, Hot Water - Electric, Public Water, Public Sewer, 200+ Amp Service

Garage/Parking
On Street

Interior
Attic, Entry Level Bedroom, Casement Windows, Double Pane Windows, Energy Efficient Windows, Window Screens

Exterior
Block Foundation, Architectural Shingle Roof, Frame Exterior

Lot
Downtown, Marina View, River View

Select a school from the following list. Schools are grouped by school type.
The schools on this list are selected by their proximity of up to 5 miles to the property address. Proximity does not guarantee enrollment eligibility. Please contact the school directly for more information on enrollment requirements.
* If there are more than 5 schools of any type within a close proximity, click on the button to see additional schools of that type near the search address.

Public Elementary (1 schools)

School District Grades Place Distance
H. H. Garnett Elementary Kent County Public Schools Preschool–5 Chestertown 0.54 mi

Public Middle (1 schools)

School District Grades Place Distance
Kent County Middle School Kent County Public Schools 6–8 Chestertown 0.81 mi

Private (4 schools)

School Grades Place Distance
Chester River Adventist School Seventh-Day Adventist 1–8 Chestertown 0.49 mi
Chestertown Christian Academy Baptist Preschool–12 Chestertown 1.23 mi
Radcliffe Creek School Nonsectarian K–8 Chestertown 1.33 mi
Kent School Nonsectarian Preschool–8 Chestertown 2.99 mi

© 2025 LiveBy. All Rights Reserved.

This report is a detailed community overview for Chestertown (21620), Maryland.

Community Quick Facts

  • Average travel time to work for people in this community: 25
  • Average salary of people in this community: $45,273

Community Summary

  • Population Density (ppl / mile): 96
  • Household Size (ppl): 2.23
  • Households w/ Children: 37%

Housing Inventory

  • Owned: 3,311 (53.4%)
  • Rented: 1,775 (28.6%)
  • Vacant: 1,110 (17.9%)
  • Total: 6,196

Population Demographics

The population of the community broken down by age group. The numbers at the top of each bar indicate the number of people in the age bracket below.

Total: 12,850
Households: 5,086
Median Age: 44.00

Climate and Weather

The Temperature chart displays average high and low values for January and July, and is designed to provide an indication of both seasonal and daily temperature variability. The Weather Risk Index indicates the calculated risk of each type of weather event occurring in the future. This risk is based on historical localized storm events and weather patterns. The national average for each type of weather event equals a score of 100, so a score of 200 would represent twice the risk as the national average, and a score of 50 would represent half the risk of the national average.

Temperature

Education

Highest Level of Education Attained

  • Less than 9th Grade: 4.6%
  • Some High School: 6.1%
  • High School Graduate: 28.4%
  • Some College: 16.5%
  • Associate Degree: 5.8%
  • Bachelor's Degree: 19.2%
  • Graduate Degree: 19.4%

Income by dollar range

Median Income: $63,806

Fair Market Rents

The Fair Market Rents show average gross rent estimates based on figures provided by the U.S. Department of Housing and Urban Development (HUD).

  • One Bedroom: $578
  • Two Bedroom: $897
  • Three Bedroom: $1,260

© 2025 LiveBy. All Rights Reserved.

Contact Information

Listing Courtesy of: Doug Ashley Realtors, LLC

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 Patterson-Schwartz Real Estate participates, and is provided by BRIGHT through a licensing agreement. 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.
Information Deemed Reliable But Not Guaranteed.
Copyright BRIGHT, All Rights Reserved
Listing data as of 9/14/2025.

206 S Water Street, Chestertown, MD 21620-1534

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Broker Compensation

An offer of broker compensation or seller concession is not a guarantee. All compensation offers and concessions are negotiable and subject to written agreement between the parties. Please consult with your real estate agent for more information.