105 N WATER STREET #2CHESTERTOWN, MD 21620

Condo · 2 Beds · 2 Full Baths · 1,011 Sq. ft.
$475,000 ACTIVE

105 N WATER STREET #2 Overview

Time on Site:
5 days
Visits:
0

Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condominium offers an exceptional opportunity to enjoy life along the banks of the Chester River. Set within an architecturally significant 1800s building that reflects the timeless character of this remarkable town, the residence combines historic charm, modern comfort, and an enviable waterfront location. Filled with character and warmth, the home features beautiful hardwood floors, soaring ceilings, tall windows, built-ins, and a wonderful period gas fireplace that creates a welcoming focal point in the spacious living room. Two generously sized bedrooms and two beautifully appointed tiled bathrooms provide comfort and style, while an in-unit washer and dryer add everyday convenience. Generous room sizes and abundant natural light enhance the home's inviting atmosphere throughout. The heart of the home is the expansive kitchen and great room at the rear of the residence, overlooking the river. Designed for gathering, entertaining, and everyday living, this impressive space features gorgeous cabinetry, stainless steel appliances, gas cooking, abundant counter space, a farmhouse sink, sunny windows, and plenty of room for dining as well as additional living space. Whether hosting friends, enjoying a quiet morning coffee, or unwinding at the end of the day, it's a room you'll find yourself gravitating toward again and again. Just off the great room, the private balcony overlooks the Chester River and offers sweeping water views in a peaceful waterfront setting. Direct water access and a dedicated boat slip make it easy to enjoy the area's iconic Chester River and everything that life on the water has to offer. Chestertown is steeped in maritime tradition and widely admired for its extraordinary collection of Federal, Georgian, and Victorian architecture. One of the Eastern Shore's most desirable destinations, residents enjoy boutique shopping, fine dining, waterfront attractions, cultural events, and a thriving arts scene. Perfectly positioned along the Chester River, this residence is a historic treasure, a waterfront retreat, and an opportunity to experience the very best of life in one of the Eastern Shore's most cherished communities.

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  • PublicFri. Jul 34:00PM - 6:00PM EDT
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105 N WATER STREET #2 Facts & Features

  • Type Condo
  • Sq. ft. 1,011
  • Price/Sq.ft. $470

Details

General

Association/HOA

  • Association Amenities: Boat Dock/Slip, Extra Storage, Mooring Area, Pier/Dock, Water/Lake Privileges
  • Association Fee 2: 460.03
  • Association Fee 2 Frequency: Monthly
  • Association Fee Includes: Common Area Maintenance, Ext Bldg Maint, Management, Insurance, Snow Removal, Taxes, Trash, Other
  • Association Name: CHESTERTOWN
  • Association: No
  • Condo/Coop Association: Yes

Listing Information

  • Real Estate Owned: No
  • Short Sale: No

Building Information

  • Building Name: WATER STREET
  • New Construction: No
  • Pool: No Pool
  • Total SQFT: 1011
  • Year Built: 1900

Location/Region

  • Country: US
  • County: KENT
  • County Or Parish: KENT
  • In City Limits: Yes
  • Subdivision Name: WATER STREET

Parking Information

  • Type of Parking: On Street

Rent/Lease Information

  • Lease Considered: No

Tax Information

  • City/Town Tax: 1602.00
  • City/Town Tax Payment Frequency: Annually
  • County Tax: 4196.00
  • County Tax Payment Frequency: Annually
  • Tax Annual Amount: $5,799.00
  • Tax Assessed Value: 370000.00
  • Tax Year: 2025

General Information

  • Property Type: Residential
  • School District Name: KENT COUNTY PUBLIC SCHOOLS
  • Senior Community: No
  • Special Listing Conditions: Standard
  • Vacation Rental: No
  • Year Assessed: 2026
  • Zoning: R-3

Interior

Building Information

  • Building Winterized: Yes
  • Cooling Fuel: Electric
  • Heating Fuel: Natural Gas

Parking Information

  • Garage: No

Beds/Baths

  • Bathrooms Full: 2
  • Bathrooms Full Main Level: 2
  • Bathrooms Half: 0
  • Bathrooms Half Main Level: 0
  • Bathrooms Total: 2
  • Bedrooms Total: 2

Building Exterior/Construction

  • Structure Type: Unit/Flat/Apartment
  • Wall & Ceiling Types: 9'+ Ceilings,Plaster Walls

Building Interior

  • Above Grade Finished Area: 1011
  • Above Grade Finished Area Source: Assessor
  • Above Grade Finished Area Units: Square Feet
  • Below Grade Finished Area: 0
  • Below Grade Finished Area Source: Assessor
  • Below Grade Finished Area Units: Square Feet
  • Central Air: Yes
  • Elevators Count: 0
  • Hot Water: Electric
  • Laundry Type: Has Laundry

General Information

  • Accessibility Features: None
  • Appliances: Dryer, Washer, Dishwasher, Disposal, Microwave, Refrigerator, Icemaker, Stove
  • Basement: No
  • Cooling: Central A/C
  • Door Features: Six Panel,French,Double Entry
  • Entry Level: 1
  • Fireplace Features: Screen,Gas/Propane,Mantel(s)
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Ceramic Tile, Solid Hardwood
  • Foundation Details: Other
  • Interior Features: Combination Kitchen/Dining, Floor Plan - Traditional, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Built-Ins, Ceiling Fan(s), Entry Level Bedroom, Kitchen - Eat-In, Kitchen - Gourmet, Kitchen - Table Space, Recessed Lighting, Sprinkler System, Wood Floors, Window Treatments, Upgraded Countertops
  • Levels: 1
  • Living Area: 1011
  • Living Area Source: Assessor
  • Main Level Bathrooms: 2.00
  • Main Level Bedrooms: 2
  • Security Features: Sprinkler System - Indoor
  • Window Features: Screens, Wood Frame, Double Hung, Double Pane

Unit Information

  • Unit Number: 2

Room Information

  • Room List: Living Room,Primary Bedroom,Bedroom 2,Kitchen

Exterior

Lot Information

  • Lot Features: Bulkheaded, Landscaping, Rear Yard
  • Road Responsibility: Public
  • Water Source: Public

Waterfront/View

  • View: Water
  • Water Body Name: CHESTER RIVER
  • Water Body Type: River
  • Water Oriented: Yes
  • Water View: Yes
  • Waterfront Features: Private Dock Site, Shared
  • Waterfront: Yes

Building Exterior/Construction

  • Architectural Style: Federal
  • Construction Materials: Brick, Wood Siding
  • Dock Type and Features: Private,Single Slip
  • Docks Count: 1
  • Patio And Porch Features: Balcony, Porch(es)
  • Roof: Metal

General Information

  • Exterior Features: Exterior Lighting
  • Fencing: Rear
  • Other Structures: Above Grade,Below Grade
  • Sewer: Public Sewer
  • Water Access Features: Private Access,Canoe/Kayak,Fishing Allowed,Boat - Powered,Swimming Allowed
  • Water Access: Yes

Room Information

Room: Bedroom 2

  • Level: Main
  • Length: 12
  • Width: 9
  • Features: Ceiling Fan(s),Flooring - HardWood,Window Treatments

Room: Kitchen

  • Level: Main
  • Length: 19
  • Width: 16
  • Features: Ceiling Fan(s),Countertop(s) - Granite,Dining Area,Flooring - HardWood,Kitchen - Eat-in,Kitchen - Gas Cooking,Lighting - Recessed,Window Treatments

Room: Living Room

  • Level: Main
  • Length: 18
  • Width: 15
  • Features: Fireplace - Gas,Flooring - HardWood,Window Treatments

Room: Primary Bedroom

  • Level: Main
  • Length: 12
  • Width: 11
  • Features: Ceiling Fan(s),Flooring - HardWood,Window Treatments

105 N WATER STREET #2 Neighborhood

Community

21620 (CHESTERTOWN) Demographics

41
Median Age
97
Population Density (per sq. mile)
48%
College Educated
$62,210
Estimated Median Income
3,408
Estimated Total Home Owners
1,835
Estimated Total Renters
65% / 35%
Estimated Owner / Renter Divide
2
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

105 N WATER STREET #2 Monthly Cost

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

105 N WATER STREET #2 Market Data

Based on the last 30 days in this zip code

$612,560
Average List Price
$288
Average Price per Square Foot
19
Properties Sold
106
Average Days on Market
84
Properties for Sale
Calculations provided by Reliance Network

105 N WATER STREET #2 History

Date Event Value Agent
6/25/2026Source: BRIGHT MLS Added to Database
June 25, 2026
Listing provided courtesy of Northrop Realty- MLS# MDKE2006680MLS ProviderContact Information: 4104651770