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Kenneth Worley
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(717) 968-7000 Cell
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108 N Water Street, Chestertown, MD 21620

$1,125,000
  • 108 N Water Street, Chestertown, MD 21620 Main Photo

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BEDS5 BATHS3 full 1 partial SQUARE FEET3,031 MLS#MDKE2007214
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONDOWNTOWN CHESTERTOWN SCHOOLKENT COUNTY PUBLIC SCHOOLS

Property Description

This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in historic Chestertown. The formal main entry, with dual brick steps approaches a generous landing, faces away from the street. At first a curiosity until you learn that a prominent family discovered the architectural plans for their "dream house" would not fit horizontally to face the prized road. During its' 100-plus years of life, the front porch (or was it the side€) was converted to a remarkable library, with requisite bookcases, and enjoys light from three sides. The formal parlor, with wood-burning fireplace and reclaimed 19th century moldings and mantle, is left of the straight-through center hall with classic black and white porcelain tiles. The intimate, yet well-proportioned dining room enhances the exceptional flow of the first-floor public rooms. A discreetly positioned powder room and butler's pantry with window and original cabinetry is conveniently placed before entering the large and sunny kitchen with premium custom cabinetry, appliances and finishes from a 2012 renovation. Two distinct patios, one screened and accessed from the dining room and the other from kitchen, overlook the large, rear garden with mature trees and landscaping. The center stairs, with a palladium window bathing light onto the steps, takes you to the first of two oversized landings that have served many lifestyle-uses over the years. The water view primary suite was renovated in 2022 by locally acclaimed Taylor Loughry LLC and boasts a timeless, luxurious aesthetic with custom built closets and Waterwork bath fixtures. Two additional bedrooms and refreshed bath with Restoration Hardware finishes, occupy the second floor. The third floor, with its own generous landing gives access to an ensuite bedroom with walk-in windowed closet (perfect for a future cedar lined closet) and a substantial sized fifth bedroom or multi-purpose space facing the Chester River and exquisite neighboring architecture. Rear yard might accommodate a pool.

108 N Water Street | MLS# MDKE2007214

This single family home located at 108 N Water Street, Chestertown, MD 21620 is currently listed for sale with an asking price of $1,125,000. This property was built in 1925 and has 5 bedrooms and 3 full and 1 partial baths with 3031 sq. ft. N Water Street is located in the DOWNTOWN CHESTERTOWN subdivision within the KENT COUNTY PUBLIC SCHOOLS school district. Search DOWNTOWN CHESTERTOWN real estate on www.kenworleyrealtor.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Connecting Stairway, Outside Entrance, Poured Concrete, Shelving, Sump Pump
Cooling: Other, Zoned, Multi Units
Fireplaces: 1
Fuel Type: Electric
Heating: Heat Pump(s), Heat Pump - Oil BackUp
Home Style: Traditional, Colonial
Lot Size: 0.24 Acres
Roof Type: Slate, Metal
Stories: 3.0
Taxes: $11,124
Year Built: 1925

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Cooktop, Dishwasher, Disposal, Dryer - Front Loading, Exhaust Fan, Icemaker, Oven - Double, Range Hood, Stainless Steel Appliances, Washer - Front Loading, Water Heater - Tankless
Electric: 200+ Amp Service
Exterior: Wood Siding, Stucco
Exterior: Sidewalks, Stone Retaining Walls, Underground Lawn Sprinkler
Fencing: Wood, Wrought Iron
Fireplace: Wood, Screen
Flooring: Wood, Ceramic Tile, Carpet
Interior: Bar, Bathroom - Walk-In Shower, Built-Ins, Butlers Pantry, Ceiling Fan(s), Crown Moldings, Floor Plan - Traditional, Formal/Separate Dining Room, Kitchen - Island, Primary Bath(s), Upgraded Countertops, Window Treatments, Wood Floors, Chair Railings
Lake Name: Chester
Location: Middle Of Block
Lot: Front Yard, Rear Yard
Lot Dimensions: 0.24 Acre(S)
Number of Rooms: 9
Parking Features: Gravel Driveway
Parking Notes: 2 Total Parking Spaces
Pet Restrictions: No Pet Restrictions
Rooms: Living Room, Dining Room, Primary Bedroom, Bedroom 2,Bedroom 3,Bedroom 4,Bedroom 5,Kitchen, Library, Foyer, Bathroom 2,Bathroom 3,Primary Bathroom
Sewer: Public Sewer
Special View Info: River, Garden/Lawn
SQFT Above Finished: 3031
SQFT Total Finished: 3031
Structure Type: Detached
Total Garage/Parking Spaces: 2
Utilities: Propane, Cable TV, Electric Available
Water: Public
Windows: Screens, Wood Frame, Storm

Room Sizes

Foyer: 23 x 7 Level - Main
Library: 20 x 9 Level - Main
Living Room: 23 x 13 Level - Main
Dining Room: 16 x 12 Level - Main
Kitchen: 20 x 12 Level - Main
Primary Bedroom: 16 x 13 Level - Upper 1

Local Schools

School District: KENT COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Cross Street Realtors LLC
Agency Phone: 4107783779

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Estimated Payment

$ 3,758.89 per month $2,503.76 Principal & Interest $927.00 Property Tax $328.13 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 11/12/2026. The listing information on this page last changed on 11/12/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 11/12/2026 8:04:30 AM EST) or Bright MLS (last updated Thu 11/12/2026 7:53:04 AM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Agent License Information: 
Licensed in Pennsylvania
Ken Worley
www.KenWorleyRealtor.com 

1680 Kenneth Road, York, PA 17408
717-757-7811

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