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117 Water Street N, Unit 1A,1B,2A,& 2BChestertown, MD 21620Price: $1,500,000

  • Price: $1,500,000
  • Est. Mortgage of $/month
  • 197 Days on Market
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Federal 30-year interest rate: 6.76% last updated on Sep 10, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $1,500,000List Price
  • 7Bedrooms
  • 5Bathrooms
  • 5,400Square Feet
**Listing price is for FOUR units for sale as an investment package! 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. ALL - Purchase one for your weekend pied--terre on the Shore! Or… invest in the whole package for $1,600,000! 1A – three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! 1B – the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. 2A – a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. 2B - a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible.
Listed by Liddy Campbell of TTR Sotheby's International Realty

Driving Directions

Railey Vacations
Railey Vacations
Office: 301-387-2124
5 Vacation Way
McHenry, MD 21541

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More Info

Location Information

  • UsmAreaChestertown
  • ViewWater, River

School Information

  • High SchoolKent County
  • High School DistrictKent County Public Schools

Parking

  • Parking FeaturesGeneral Common Elements, Private, Shared Driveway
  • Parking TypesDriveway, Off Street, Parking Lot
  • Total Garage And Parking Spaces5

Location

  • Address117 Water Street N
  • Building Number117
  • CountyKent
  • Cross StreetMaple Avenue
  • DirectionsGPS
  • Distance To Body Of Water UnitsBlocks
  • Federal Flood ZoneA
  • In City Limits YNYes
  • IncorporatedcitynameChestertown
  • Living Area SourceEstimated
  • StateMD
  • SubdivisionNone Available
  • TownChestertown
  • Water Oriented YNYes
  • Zip21620

Utilities

  • CoolingDuctless/Mini-Split, Programmable Thermostat, Zoned, Multi Units
  • Cooling FuelElectric
  • Heat SystemHeat Pump(s), Forced Air, Programmable Thermostat
  • Heating FuelElectric
  • Heating YNYes
  • Internet ServicesFiber Optic
  • SewerPublic Sewer
  • UtilitiesPropane - Community
  • Water HeaterPropane, Tankless
  • Water SourcePublic

Water Body

  • Dock1
  • Dock Slip Conveyance MultiAssociation Owned
  • Dock Type And FeaturesPrivate, Pier (Perpendicular), Material - Treated Lumber
  • Tidal Water YNYes
  • Water AccessYes
  • Water Body NameCHESTER RIVER
  • Water Body TypeRiver
  • Water FeaturesPrivate Access
  • Water View YNYes
  • WaterfrontYes
  • Waterfront FeaturesShared, Private Dock Site, Navigable Water

Basic Information

  • Association Fee IncludesCommon Area Maintenance, Gas, Insurance, Water, Lawn Maintenance
  • Association Fee2350
  • Association Fee2 FrequencyMonthly
  • Broker NameTTR Sotheby's International Realty
  • Condo YNYes
  • List Price$1,500,000
  • LocationTypeRiver
  • MLS NumberMDKE2006158
  • MLS Property TypeResidential
  • Price Per Square Foot278
  • StatusACT
  • Unit Number1A,1B,2A, & 2B

Property

  • Above Grade Finished Area5400
  • Above Grade Finished Area SourceEstimated
  • Above Grade Finished Area UnitsSquare Feet
  • New Construction YNN
  • ZoningR-3

Interior

  • FlooringWood, Tile/Brick, Ceramic Tile, Concrete
  • RoomsBedroom 2, Bedroom 3, Bedroom 1, Bathroom 1, Bathroom 2
  • Walls CeilingsDry Wall, Plaster Walls

Exterior

  • Patio And Porch FeaturesPatio(s)
  • RoofSlate, Metal

Property Information

  • Area Total5,400
  • Area Total SourceEstimated
  • Municipal Trash YNYes

Amenities

  • Amenities
    • Common Grounds
    • Extra Storage
    • Laundry Facilities
    • Picnic Area
    • Pier/Dock
    • Reserved/Assigned Parking
    • Water/Lake Privileges
  • Other AmenitiesBasement, Fireplace, Waterfront, Water View, Dock
  • PoolNo Pool
  • Slips2

Other

  • Appliances IncludedWasher, Dryer, Water Heater - Tankless
  • View Count1

Tax Information

  • Assessment Year2018
  • City Town Tax6891
  • County Tax18046
  • County Tax Payment FrequencyAnnually
  • Tax Assessment Amount833700
  • Tax Year2026
  • Taxes$24,937
  • Total Taxes Payment FrequencyAnnually

Basic Information

Building

  • Bathroom5
  • Basement
    • Interior Access
    • Other
    • Outside Entrance
    • Partially Finished
    • Rear Entrance
    • Walkout Level
  • Basement YNYes
  • Bedrooms7
  • Construction MaterialsCombination, Brick, Wood Siding, Vinyl Siding
  • Fireplace1
  • Fireplace YNYes
  • FoundationBlock, Brick/Mortar
  • Full Bath5
  • Laundry TypeCommon, Lower Floor
  • Levels4
  • Lower Level1 Bedrooms2
  • Lower Level1 Full Baths2
  • Lower Level1 Total Baths2
  • Lower Levels Total Baths2
  • Lower Levels Total Bedrooms2
  • Lower Levels Total Full Baths2
  • Main Level Bedrooms2
  • Main Level Full Baths2
  • Main Level Total Baths2
  • Property StyleGeorgian, Colonial, Unit/Flat
  • Rooms Total12
  • Square Feet5,400
  • Story ListLower 1, Main, Upper 1
  • Structure Design TypeDetached
  • Upper Level1 Bedrooms3
  • Upper Level1 Full Baths1
  • Upper Level1 Total Baths1
  • Upper Levels Total Baths1
  • Upper Levels Total Bedrooms3
  • Upper Levels Total Full Baths1
  • Year Built1885

Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. 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 Railey Vacations 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.Data last updated September 14, 2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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