Property

Chestertown, MD 21620 206 S Water Street

$619,000

206 S Water Street Chestertown, MD - Image 1206 S Water Street Chestertown, MD - Image 2206 S Water Street Chestertown, MD - Image 3
41 more
206 S Water Street Chestertown, MD - Image 4206 S Water Street Chestertown, MD - Image 5206 S Water Street Chestertown, MD - Image 6206 S Water Street Chestertown, MD - Image 7206 S Water Street Chestertown, MD - Image 8206 S Water Street Chestertown, MD - Image 9206 S Water Street Chestertown, MD - Image 10206 S Water Street Chestertown, MD - Image 11206 S Water Street Chestertown, MD - Image 12206 S Water Street Chestertown, MD - Image 13206 S Water Street Chestertown, MD - Image 14206 S Water Street Chestertown, MD - Image 15206 S Water Street Chestertown, MD - Image 16206 S Water Street Chestertown, MD - Image 17206 S Water Street Chestertown, MD - Image 18206 S Water Street Chestertown, MD - Image 19206 S Water Street Chestertown, MD - Image 20206 S Water Street Chestertown, MD - Image 21206 S Water Street Chestertown, MD - Image 22206 S Water Street Chestertown, MD - Image 23206 S Water Street Chestertown, MD - Image 24206 S Water Street Chestertown, MD - Image 25206 S Water Street Chestertown, MD - Image 26206 S Water Street Chestertown, MD - Image 27206 S Water Street Chestertown, MD - Image 28206 S Water Street Chestertown, MD - Image 29206 S Water Street Chestertown, MD - Image 30206 S Water Street Chestertown, MD - Image 31206 S Water Street Chestertown, MD - Image 32206 S Water Street Chestertown, MD - Image 33206 S Water Street Chestertown, MD - Image 34206 S Water Street Chestertown, MD - Image 35206 S Water Street Chestertown, MD - Image 36206 S Water Street Chestertown, MD - Image 37206 S Water Street Chestertown, MD - Image 38206 S Water Street Chestertown, MD - Image 39206 S Water Street Chestertown, MD - Image 40206 S Water Street Chestertown, MD - Image 41206 S Water Street Chestertown, MD - Image 42206 S Water Street Chestertown, MD - Image 43206 S Water Street Chestertown, MD - Image 44206 S Water Street Chestertown, MD - Image 45
Presented By: TTR Sotheby's International Realty
  • MLS# MDKE2005840
  • 10/22/2025
  • Request Tour
  • Request Info
  • Beds • 4
  • Full/Half Baths • 3 / 1
  • SQFT • 2,008

Home Details

Live in the heart of Chestertowns Historic Districtsee 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 deckbuilt 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, youre just steps from the waterfront, Wilmer Park, shops, restaurants, bakeries, pubs, Farmers Market, arts district, and more. Cook and entertain in style with Heartland appliances and handcrafted cabinetry in the kitchen. 206 S. Water Streeta feels-like-new historic home in Chestertowns most walkable location. Note The vacant lot next door is not part of this property. Separate owner.
Presented By: TTR Sotheby's International Realty

Interior Features for 206 S Water Street

Bedrooms

Bedrooms Count All Upper Levels3
Bedrooms Count Upper Level 12
Bedrooms Count Upper Level 21
Main Level Bedrooms1
Total Bedrooms4

Bathrooms

Bathrooms Half Main Level1
Bathrooms Full Upper Level 21
Bathrooms Full Upper Level 11
Bathrooms Full All Upper Levels2
Bathrooms Count Upper Level 21.00
Bathrooms Count Upper Level 11.00
Bathrooms Count All Upper Levels2
Half Baths1
Total Baths4

Other Interior Features

LivingAreaSourceAssessor
Below Grade Unfin Area UnitsSquare Feet
Below Grade Unfin SQFT0
Below Grade Unfin SQFT SourceAssessor
Above Grade Finished Area2008
Above Grade Finished Area SourceAssessor
Above Grade Finished Area Unit TypeSquare Feet
Basement (Y/N)No
Below Grade Finished Area0
Below Grade Finished Area SourceAssessor
Below Grade Finished Area Unit TypeSquare Feet
Central Air Y/NNo
Fireplace FeaturesGas/Propane
Fireplace Y/NYes
FlooringHardwood
Heating FuelElectric, Propane - Leased
Heating Y/NYes
Hot WaterElectric
Interior AmenitiesBreakfast Area, Crown Moldings, Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Island, Kitchen - Table Space, Primary Bath(s), Wood Floors
Laundry TypeMain Floor
Total Fireplaces1

General for 206 S Water Street

Acceptable FinancingCash, Conventional, FHA, VA
AccessibilityNone
AppliancesDishwasher, Disposal, Dryer, Oven/Range - Electric, Washer/Dryer Stacked, Washer
Architectural StyleColonial, Coastal
Bathrooms Count Main Level2.00
Bathrooms Full Main Level1
Body of WaterChester River
CityCHESTERTOWN
Condo/Coop Association fee Y/NNo
Construction MaterialsFrame
Cool FuelElectric
CoolingDuctless/Mini-Split, Zoned
CountyKENT
DirectionsCross the Chester River Bridge, left on N Queen St, left on High St, right on S Water St to house on the right.
DisclosuresLead Based Paint - Federal, Lead Based Paint - State, Prop Disclaimer
Full Baths3
Garage Y/NNo
HOANo
HeatingHeat Pump(s)
Historic Y/NYes
Home Warranty Y/NNo
Lease Considered Y/NNo
Levels3
Living Area2008
Lot Size Square Feet1888.00
Lot Size UnitsSquare Feet
MunicipalityChestertown
New ConstructionNo
Other StructuresAbove Grade, Below Grade
OwnershipFee Simple
Patio/Porch FeaturesPorch(es)
Possession0-30 Days CD, 61-90 Days CD, 31-60 Days CD, Coin w/Sell Sett
Price Per Sq Ft Total AG308.27
Property ConditionExcellent
Property TypeResidential
School DistrictKENT COUNTY PUBLIC SCHOOLS
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusACTIVE
Structure TypeDetached
Subdivision NameCHESTERTOWN HISTORIC DISTRICT
Tax Annual Amount7755.0
Tax Assessed Value518600.0
Tax Year2024
Total SQFT2008
Vacation Rental Y/NNo
Water Access Y/NNo
Year Built1900
Year Built SourceAssessor
ZoningR-5

Exterior for 206 S Water Street

Foundation DetailsCrawl Space
Horse Y/NNo
Land Assessed Value174600.00
Land Use CodeR
Lot Size Acres0.04
Lot Size SourceAssessor
Navigable Water Y/NNo
PoolNo Pool
SpaNo
Type of ParkingOn Street
Water Body TypeRiver
Water Oriented Y/NYes
Water SourcePublic
Water View Y/NNo
Waterfront Y/NNo

Additional Details

Price History

YOLANDA CASSIDY-BOGAN

Associate
Price $619,000
MLS#MDKE2005840
List Date 10/22/2025
Property Type Single Family
Phone (973) 868-7789
Request Tour
Request Info
Visit My Website

Similar Properties to 206 S Water Street

Login & Get Full Access

Thank you for registering.

Are you currently working with one of these agents?

Ask A Question

Get Pre-Approved Now!

Give yourself a better position in the competitive home buying market. Complete the form to get started on your journey to purchase your dream home. Our lending partner has a wide variety of lending options available and advanced mortgage technology. As a result, our lending partner's clients enjoy a flawless experience through impeccable execution and timely communication throughout the process.

© Copyright 2025 RE/MAX Lifetime Realtors All Rights Reserved. Designed & Managed by L.A. Marketing & Web Presence Consulting, LLC..

Get Pre-approved