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105 N Water Street # 2 Chestertown, MD $ 475,000
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105 N Water Street # 2
$ 475,000
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105 N Water Street # 2

Chestertown, MD, 21620
$ 475,000
Bedrooms2 Baths2.0 Sq 1,011

Monthly Estimate*

$ 2,999

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Condo for sale in Chestertown, MD

for $475,000 with 2 bedrooms and 2 full baths. This 1,011 square foot condo was built in 1900.

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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Condo Active

Price

$ 475,000

Bedrooms

2

Full Bath

2

Property Type

Condo

Taxes

$ 5,799

Style

Federal

Year Built

1900

Town/City

Chestertown

County/Region

Kent

MLS | Web ID

MDKE2006680
Features
General
Living Area 1011
Sewer Public Sewer
Heating Heat Pump(s)
Cooling Central A/C
Possession Negotiable Coin w/Sell Sett
Roof Metal
Appliances Dryer Washer Dishwasher Disposal Microwave Refrigerator Icemaker Stove
Zoning R-3
Association Fee Includes Common Area Maintenance Ext Bldg Maint Management Insurance Snow Removal Taxes Trash Other
Patio/Porch Features Balcony Porch(es)
Architectural Style Federal
Security Features Sprinkler System - Indoor
Construction Materials Brick Wood Siding
School District KENT COUNTY PUBLIC SCHOOLS
Year Built 1900
View Water
Levels 1
Unit Number 2
Tax Year 2025
Ownership Condominium
Cool Fuel Electric
Municipality Chestertown
Waterfront Features Private Dock Site Shared
Building Name WATER STREET
Accessibility None
HOA Fee 2 460.03
County KENT
New Construction N
Property Type Residential
Association Amenities Boat Dock/Slip Extra Storage Mooring Area Pier/Dock Water/Lake Privileges
HOA N
Subdivision Name WATER STREET
Garage Y/N N
Water Access Y/N Y
Other Structures Above Grade Below Grade
Full Baths 2
Status ACTIVE
Directions Take MD-213 N to N Water St in Chestertown. Arrive at 105 N Water St Chestertown MD 21620.
City CHESTERTOWN
Body of Water CHESTER RIVER
Association Name CHESTERTOWN
Senior Community Y/N N
HOA Fee 2 Frequency Monthly
Tax Annual Amount 5799.0
Structure Type Unit/Flat/Apartment
Condo/Coop Association fee Y/N Y
Number of Community Slips 8
Bathrooms Full Main Level 2
Bathrooms Count Main Level 2.00
Price Per Sq Ft Total AG 469.83
Acceptable Financing Conventional Cash
Lease Considered Y/N N
Vacation Rental Y/N N
Virtual Tour https://media.homesight2020.com/105-North-Water-Street-2/idx
Location Type River
Standard Status Active
Year Built Source Assessor
Tax Lot 2
Federal Flood Zone YES
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Interior
Interior Amenities 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 Spa
Heating Fuel Natural Gas
Flooring Ceramic Tile Solid Hardwood
Total Fireplaces 1
Fireplace Features Screen Gas/Propane Mantel(s)
Hot Water Electric
Basement (Y/N) N
Heating Y/N Y
Window Features Screens Wood Frame Double Hung Double Pane
Fireplace Y/N Y
Above Grade Finished Area 1011
Half Baths 0
Central Air Y/N Y
Total Bedrooms 2
Below Grade Finished Area 0
Entry Level 1
Room Type Living Room Primary Bedroom Bedroom 2 Kitchen
Main Level Bedrooms 2
Below Grade Finished Area Unit Type Square Feet
Laundry Type Has Laundry
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 2
Number of Elevators 0
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Exterior
Exterior Amenities Exterior Lighting
Pool No Pool
Fencing Rear
Lot Features Bulkheaded Landscaping Rear Yard
Water Source Public
Type of Parking On Street
Foundation Details Other
Water View Y/N Y
Water Body Type River
Waterfront Y/N Y
Door Features Six Panel French Double Entry
Water Access Features Private Access Canoe/Kayak Fishing Allowed Boat - Powered Swimming Allowed
Road Responsibility Public
Number of Docks 1
Land Assessed Value 185000.00
Navigable Water Y/N Y
Number of Slips 1
Water Oriented Y/N Y
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Internal Only
Street Number 1 105
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* Excluded Features
List By
Northrop Realty

Broker

missy@millerteam.com

Email

Affordability Calculator

$3,482
Per Month
86%
14%
0%
Monthly Principal & Interest
$2,999
Monthly Property Taxes
$483
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3535796 Elementary School
3533824 Middle School
Unknown High School High School
See complete school information
Pricing History
DatePricePrice ChangeDescription
6/26/2026$475,000 Listed Price

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105 N Water Street # 2, Chestertown, MD, 21620 is a Condo for sale at $475,000 with 1,011 sqft. 105 N Water Street # 2 has 2 bedrooms, 2.0 baths, and was built in 1900. The property's zip code is 21620 which is in Chestertown, MD

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