New Listing
$1,125,000
 $6,039 est/mo Sourced by Back At You

108 N Water St,CHESTERTOWN, MD 21620

CHESTERTOWN, MD 21620

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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.

Details

MLS #MDKE2007214
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusComing Soon-bright
Year1925
Days On Site3
Listing Provided ByCross Street Realtors LLC | Richard Keaveney

Features

Bed(s)5
Bath(s) 4 Total
SQ Feet3,031
BasementY
Story(s)3
ZoningR-3
Acreage0.24
Property ViewRiver, Garden, Lawn

Interior

Rooms Total9
CoolingOther, Zoned, Multi Units
Heating Yes / NoYes
HeatingHeat Pump(s), Heat Pump - Oil Back Up
Interior FeaturesBar, 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
Window FeaturesScreens, Wood Frame, Storm
FurnishedNo
AppliancesCooktop, Dishwasher, Disposal, Dryer - Front Loading, Exhaust Fan, Icemaker, Oven - Double, Range Hood, Stainless Steel Appliances, Washer - Front Loading, Water Heater - Tankless

Exterior

Exterior FeaturesSidewalks, Stone Retaining Walls, Underground Lawn Sprinkler
RoofSlate, Metal
Security FeaturesCarbon Monoxide Detectors, Smoke Detector, Security System
Construction MaterialsWood Siding, Stucco
Foundation DetailsConcrete Perimeter
Lot FeaturesFront Yard, Rear Yard

Parking

Garage Yes / NoNo
Parking FeaturesGravel Driveway

Utilities

UtilitiesPropane, Cable TV, Electric Available

Taxes

Tax Annual Amount11124

Area Information

StateMD
CountyKENT MD
CityCHESTERTOWN
Zip Code21620
AreaKENT MD
Community NameDOWNTOWN CHESTERTOWN
School DistrictKENT COUNTY PUBLIC SCHOOLS
Listing VS Median (in DOWNTOWN CHESTERTOWN)
Price:
$1,125,000
low | high
Med:
$712,500
86.666666666667% of Average
sqft:
3,031
low | high
Med:
2,417
70.273837017486% of Average
$ / sqft:
$371
low | high
Med:
$269
77.573066962634% of Average
On site:
3
low | high
Med:
17.5
17.142857142857% of Average
Sourced by Back At You

Market Activity 21620

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Learn More About This Property

StateMD
CountyKENT MD
CityCHESTERTOWN
Zip Code21620
AreaKENT MD
Community NameDOWNTOWN CHESTERTOWN
School DistrictKENT COUNTY PUBLIC SCHOOLS
Listing VS Median (in DOWNTOWN CHESTERTOWN)
Price:
$1,125,000
low | high
Med:
$712,500
86.666666666667% of Average
sqft:
3,031
low | high
Med:
2,417
70.273837017486% of Average
$ / sqft:
$371
low | high
Med:
$269
77.573066962634% of Average
On site:
3
low | high
Med:
17.5
17.142857142857% of Average
Sourced by Back At You
Nearby Listings (Within 1/10 mile)
Price: $843K - $1.406M
sqft: 2,000 - 3,500
Nearby Listings Property ImageNearby Listings Details
105 HIGH ST Property Photo 1
$1,195,000
105 High St
Chestertown, MD 21620
Listing Updated: November 3, 2026 at 8:15:29 PM PST