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105 N Water Street , #2

CHESTERTOWN, MD 21620
  • $475,000
  • STATUS: Active
  • ON SITE: 21 Days
  • ID#: MDKE2006680
$475,000
  • 2
    BEDS
  • N/A
    ACRES
  • 2
    BATHS
  • 0
    1/2 BATHS
  • 1,011
    SQFT
  • $470
    $/SQFT
Neighborhood:
Type:
Condo
Built:
1900
County:

School Ratings & Info

School District:

Description

Open House Friday July 3rd 4-6pm! 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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©2026 Bright MLS, All Rights Reserved. IDX information is provided exclusively 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. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or EXIT Realty Enterprises. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Data last updated: 2026-07-16T23:53:35.82.
www.exitrealtyenterprises.com/homes/178138532
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105 N Water Street , #2 CHESTERTOWN, MD 21620

  • Price: $475,000
  • Status: Active
  • On Site: 21 Days
  • ID#: MDKE2006680
2
Beds
2
Baths
0
½ Baths
N/A
Acres
1,011
SQFT
$470
$/SQFT
1900
Built
Neighborhood:
Water Street
County:
Kent
School District:
Kent County Public Schools
Property Description
Open House Friday July 3rd 4-6pm! 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.
Exterior Features

Architectural Style Federal Construction Materials BrickWood Siding Distance To Body Of Water 30 Docks 1 Door Features Six PanelFrenchDouble Entry Exterior Features Exterior Lighting Fencing Rear Garage YN No Location Type River Lot Features BulkheadedLandscapingRear Yard Parking Types On Street Patio And Porch Features BalconyPorch(es) Pool No Pool Road Responsibility Public Roof Metal Slips 1 Unit Building Type Garden 1 - 4 Floors View Water Water Access Features Private AccessCanoe/KayakFishing AllowedBoat - PoweredSwimming Allowed Water Access YN Yes Water Body Name CHESTER RIVER Water Body Type River Water View YN Yes Waterfront Features Private Dock SiteShared Waterfront YN Yes

Interior Features

Above Grade Fin SQFT 1011 Appliances DryerWasherDishwasherDisposalMicrowaveRefrigeratorIcemakerStove Basement YN No Below Grade Finished Area 0 Below Grade Unfinished Area 0 Cooling Central A/C Fireplace Features ScreenGas/PropaneMantel(s) Fireplace YN Yes Fireplaces Total 1 Flooring Ceramic TileSolid Hardwood Heating Heat Pump(s) Heating YN Yes Interior Features Combination Kitchen/DiningFloor Plan - TraditionalBathroom - Tub ShowerBathroom - Walk-In ShowerBuilt-InsCeiling Fan(s)Entry Level BedroomKitchen - Eat-InKitchen - GourmetKitchen - Table SpaceRecessed LightingSprinkler SystemWood FloorsWindow TreatmentsUpgraded Countertops Laundry Type Has Laundry Levels 1 Main Level Bedrooms 2 Pets Allowed No Pet Restrictions Room List Living RoomPrimary BedroomBedroom 2Kitchen Security Features Sprinkler System - Indoor Unit Floors 1 Walls Ceilings 9'+ CeilingsPlaster Walls

Property Features

Acceptable Financing ConventionalCash Accessibility Features None Association Amenities Boat Dock/SlipExtra StorageMooring AreaPier/DockWater/Lake Privileges Association Fee Includes Common Area MaintenanceExt Bldg MaintManagementInsuranceSnow RemovalTaxesTrashOther Association Fee2 460.03 Association Fee2 Frequency Monthly Association Name CHESTERTOWN Association YN No Central Air YN Yes Condo YN Yes Cooling Fuel Electric Elevators 0 Entry Level 1 Federal Flood Zone YES Federal Flood Zone YN Yes Foundation Details Other Heating Fuel Natural Gas Hot Water Electric Lease Considered YN No Municipality Chestertown Navigable Water YN Y New Construction YN No Original MLSNumber 805051017586 Ownership Interest Condominium Pets Allowed YN Yes Sale Type Standard Senior Community YN No Sewer Public Sewer Structure Design Type Unit/Flat/Apartment Tax Annual Amount 5799.00 Tax Lot 2 Vacation Rental YN No Water Source Public Window Features ScreensWood FrameDouble HungDouble Pane Year Built Effective 2005 Zoning R-3

Listing courtesy of Northrop Realty: .


©2026 Bright MLS, All Rights Reserved. IDX information is provided exclusively 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. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or EXIT Realty Enterprises. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Data last updated: 2026-07-16T23:53:35.82.
 
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