Date
Details
Price
Change
Source
6/25/2026
Listed
$475,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
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.
Full Property Details
Full Property Details for 105 N Water St #2
General
- Price: $475,000
- HOA FEE: $460/month
- Taxes: $5,799 (2025)
- Status: Active
- Type: Condo
- Source: BrightMLSMidAtlantic
- MLS ID: MDKE2006680
- Updated: 6/25/2026
- Added to Site: 1 day(s) ago
Interior
- Rooms/Areas: Living Room, Primary Bedroom, Bedroom 2, Kitchen
- 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
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Screen, Gas/Propane, Mantel(s)
- Appliances: Dryer, Washer, Dishwasher, Disposal, Microwave, Refrigerator, Icemaker, Stove
- Flooring: Ceramic Tile, Solid Hardwood
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
- Main Floor Baths: 2
- Main - Full Baths: 2
Bedrooms
- Total Bedrooms: 2
- Bedrooms Main & Up: 2
Other Rooms
- Laundry: Has Laundry
Additional Information
- Shared Amenities: Boat Dock/Slip, Extra Storage, Mooring Area, Pier/Dock, Water/Lake Privileges
- Security/Safety: Sprinkler System - Indoor
Exterior
- Exterior Features: Exterior Lighting
- Porch/Patio/Deck: Balcony, Porch(es)
Parking
- Parking Type: On Street
Location
- Municipality: Chestertown
- County: KENT
- Subdivision: WATER STREET
- Building Name: WATER STREET
- Driving Directions: Take MD-213 N to N Water St in Chestertown. Arrive at 105 N Water St Chestertown, MD 21620.
- Location Details: River
- City Limits: Yes
School Information
- School District: Kent County Public Schools
Community
- Assoc. Name: CHESTERTOWN
- Assoc. Fees Include: Common Area Maintenance, Ext Bldg Maint, Management, Insurance, Snow Removal, Taxes, Trash, Other
- Pets Allowed: Yes
- Pets: No Pet Restrictions
Heating & Cooling
- Central air: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Natural Gas
- Water Heater: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Dist. to Water: 30 Feet
Structural Information
- Architectural Style: Federal
- Structure Type: Garden 1 - 4 Floors
- Construction: Brick, Wood Siding
- Foundation: Other
- Roof: Metal
- Walls/Ceilings: 9'+ Ceilings, Plaster Walls
- Windows: Screens, Wood Frame, Double Hung, Double Pane
- Doors: Six Panel, French, Double Entry
- Entry Floor Number: 1
- Stories Description: Main
- Square Feet: 1,011
- Sq. Ft. Source: Assessor
- Living Area: 1,011 Sq. Ft.
- Finished Above Grnd: 1,011 Sq. Ft.
- Year Built: 1900
- Year Built Source: Assessor
Unit Information
- Unit Floor in Bldg.: 1
Lot Features
- Property View: Water
- Zoning: R-3
- Lot Description: Bulkheaded, Landscaping, Rear Yard
- Fencing (Description): Rear
Water Features
- Water Front: Yes
- Water View: Yes
- Navigable Water: Yes
- Water Access: Yes
- Water Access Desc: Private Access, Canoe/Kayak, Fishing Allowed, Boat - Powered, Swimming Allowed
- Water Front Type: River
- Water Front Name: CHESTER RIVER
- Dock/Slip Conveys: Yes
- Docks: 1
Financial Considerations
- Price Per Sq. Ft.: $469.83
- Condo Fee: $460
- Condo Fee Freq: Monthly
- Assessment Year: 2026
- City/TownTax: $1,602
- City/TownTax Freq: Annually
- County Tax: $4,196
- County Tax Freq: Annually
- Tax w/Assessment: $370,000
- Tax Amount: $5,799
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 1011
Disclosures and Reports
- Ownership: Condominium
- Condo: Yes
- Flood Zone: Yes
- Lot Number: 2
Listed by Northrop Realty, Missy A Aldave and Northrop Realty, Megan Miller Minderlein
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agents
— 105 N Water St #2 —
Missy A Aldave
Northrop Realty
Megan Miller Minderlein
Northrop Realty
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 105 N Water St #2
School District:Kent County Public Schools
| Name | Grades | Distance |
|---|---|---|
H. H. Garnett Elementary School 320 Calvert Street, Chestertown, MD 21620 | PK-5 | 0.5 mi |
Kent County Middle School 402 East Campus Avenue, Chestertown, MD 21620 | 6-8 | 0.7 mi |
Kent County High School 25301 Lambs Meadow Road, Worton, MD 21678 | 9-12 | 5.5 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 105 N Water St #2
Tax History
Tax History for 105 N Water St #2
Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,799
—
$370,000
—
2024
$5,799
1%
$370,000
—
2023
$5,762
—
$370,000
—
2022
$5,762
-8%
$370,000
—
2020
$6,269
—
$370,000
-8%
2021
$6,269
-20%
$400,000
-20%
2020
$7,820
2%
$500,000
2%
2019
$7,641
5%
$491,667
2%
2018
$7,269
2%
$483,333
2%
2017
$7,144
306%
$475,000
—
2016
$1,758
-75%
$475,000
-5%
2015
$7,144
-10%
$500,000
-5%
2014
$7,896
—
$525,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 105 N Water St #2
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105 N Water Street #2, Chestertown, MD 21620 (MLS# MDKE2006680) is a Condo property with 2 bedrooms and 2 full bathrooms. 105 N Water Street #2 is currently listed for $475,000 and was received on June 25, 2026. Want to learn more about 105 N Water Street #2? Do you have questions about finding other Condo real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.