101 N Water Street

Chestertown, MD
$ 4,150,000 Beds 6 Baths 6 Sq 7,440 Virtual Tour
Monthly Estimate* How much can I afford?

"Widehall" is the most acclaimed historic downtown waterfront estate in Chestertown MD, since 1769. The many stewards of this magnificent residence, including two Maryland governors and two US Senators, have been ambassadors of hospitality for both town folk and national leaders. Each have protected and enhanced its authentic beauty ... from the original mahogany hanging staircase (c 1769) to geothermal heating and air (c 2013). Widehall is quite special to our town. The more formal main floor rooms provide the ideal setting for both parties and intimate gatherings. The flow between each of the rooms is perfect. Three of the six wood burning fireplaces add only a part of the warmth and ambiance of the main level of this residence. The chilled air or warm summer breeze is steps away on the first of two grand verandas overlooking the Chester River, thoughtfully added in 1911. Ascending the mahogany stairs to the second floor maintains the elegant feel of a grand home but immediately establishes a feeling of comfort and relaxation with a large family room. Surrounded by three bedrooms, each with their private baths, there are two doorways to the second of the very large waterfront verandas. A former servants wing provides for a bath, laundry room and windowed closet space. The top floor (number three) boasts three bedrooms, two baths and an additional laundry. Architects of a by-gone era creatively used dormer space for exquisite closet and storage space. Currently, each bedroom is named in honor of an acclaimed figure with close connections to Chestertown and the Eastern Shore. Your journey is not quite finished. A gracious staircase, discreetly hidden behind a wainscoted door, brings you to the unmatched "Widow's Walk" or rooftop deck with the most spectacular views of the Chester River and Chestertown. In many cities, a visit to this rooftop would be worth the price of a hefty admission. Our beautiful town and its people want to welcome you to continue the history and stories of "Widehall". Prospective buyers should be informed of the vital socio-economic trend this small town of America is experiencing and that of its acclaimed Arts & Entertainment District. Yes, our weekly Farmer's Market is "gossip central" and awesome for river and farm fresh provisions .... but it is the community that makes us a great place to to live. From monthly First Friday evenings for gallery and shop visits to a variety of annual festivals that include Downrigging weekend, Legacy Day, the Chestertown Tea Party reenactment, Dickens of a Christmas, and more add to the vibrancy of our town with Widehall enjoying the best viewing action. The convenience of a deep water dock and great lawn combined with short-walks to morning coffee and fresh pastries, evening cocktails and fine dining is unparalleled on the Eastern Shore.

Single Family

  • Price
  • $ 4,150,000
  • Lot Size
  • 0.94 Acres
  • Bedrooms
  • 6
  • Sqr Footage
  • 7,440
  • Full Bathrooms
  • 5
  • Year Built
  • 1769
  • Half Bathrooms
  • 2
  • City, Zip
  • Chestertown
  • Taxes
  • $ 34483
  • County
  • KENT
  • Style
  • Georgian
  • Area
  • MLS#
  • MDKE2000342
  • Zip
  • 21620
Listing Provided by: Cross Street Realtors LLC
Data Source: Bright MLS - 382 - MD



Accessibility None
Appliances Commercial Range, Dishwasher, Disposal, Dryer, Icemaker, Refrigerator, Stainless Steel Appliances, Washer, Water Conditioner - Owned
Architectural Style Georgian
Association Y/N No
Basement Combination, Connecting Stairway, Drainage System, Partially Finished, Poured Concrete, Rear Entrance
Bathrooms Count Main Level 1.00
Condo/Coop Association Y/N No
Construction Materials Brick
Cool Fuel Geothermal, Electric
Cooling Geothermal, Central A/C
County KENT
Days on Market 114
Garage Y/N No
Heating Zoned, Central
Historic Y/N Yes
Interior Features Additional Stairway, Air Filter System, Bar, Breakfast Area, Built-Ins, Butlers Pantry, Chair Railings, Crown Moldings, Floor Plan - Traditional, Kitchen - Eat-In, Kitchen - Gourmet, Kitchen - Island, Pantry
Levels 3
Lot Size Square Feet 41000.00
Municipality Chestertown
New Construction No
Other Structures Above Grade, Below Grade
Ownership Fee Simple
Patio/Porch Features Balconies- Multiple, Roof
Pool Y/N No Pool
Possession Settlement
Price Per Sq Ft 557.8
Property Type Residential
PropertyCondition Excellent
Roof Slate
School District 121139164602
Security Features 24 hour security, Carbon Monoxide Detector(s), Fire Detection System, Exterior Cameras, Sprinkler System - Indoor
Senior Community Y/N No
Sewer Public Sewer
Structure Type Detached
Tax Annual Amount 34483.0
Tax Year 2021
Vacation Rental Y/N No
Water Access Y/N Yes
Water Body Name Chester
Zoning R-3

Interior Features

Above Grade Finished Area 7440
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Basement Y/N Yes
Bathrooms Count All Lower Levels 1
Bathrooms Count All Upper Levels 5
Bathrooms Count Lower Level 1 1.00
Bathrooms Count Upper Level 1 3.00
Bathrooms Count Upper Level 2 2.00
Bathrooms Full All Upper Levels 5
Bathrooms Full Upper Level 1 3
Bathrooms Full Upper Level 2 2
Bathrooms Half All Lower Levels 1
Bathrooms Half Lower Level 1 1
Bathrooms Half Main Level 1
Bedrooms Count All Upper Levels 6
Bedrooms Count Upper Level 1 3
Bedrooms Count Upper Level 2 3
Below Grade Finished Area Source Assessor
Below Grade Finished Area Unit Type Square Feet
Below Grade Unfin Area Units Square Feet
Below Grade Unfin Sqft Source Assessor
Central Air Y/N Yes
Fireplace Features Brick
Fireplace Y/N Yes
Full Baths 5
Half Baths 2
Heating Fuel Geo-thermal, Oil
Heating Y/N Yes
Hot Water Oil
Laundry Type Upper Floor
Living Area 7440
Room Type Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 4, Bedroom 5, Kitchen, Family Room, Foyer, Breakfast Room, Study, Great Room, Laundry, Other, Recreation Room, Utility Room, Workshop, Bedroom 6
Total Baths 7
Total Bedrooms 6
Total Fireplaces 6

Exterior Features

Horse Y/N No
Lot Size Acres 0.94
Lot Size Source Assessor
Navigable Water Y/N Yes
Parking Features Crushed Stone
Spa No
Total Parking Spaces 10
Type of Parking Driveway, On Street
Water Body Type River
Water Oriented Y/N Yes
Water Source Public
Water View Y/N No
Waterfront Y/N Yes

Room Details

Bathroom 2 Upper 1
Bathroom 3 # 2 Upper 2
Bathroom 3 Upper 1
Bedroom 2 Upper 1
Bedroom 4 Upper 2
Bedroom 5 Upper 2
Bedroom 6 Upper 2
Breakfast Room Main
Dining Room Main
Family Room Upper 1
Foyer Main
Full Bath Upper 2
Great Room Main
Half Bath Main
Kitchen Main
Laundry Upper 1
Laundry # 2 Upper 2
Living Room Main
Living Room # 2 Main
Other Main
Primary Bathroom Upper 1
Primary Bedroom Upper 1
Recreation Room Lower 1
Study Upper 1
Utility Room Lower 1
Workshop Lower 1


  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator


Per Month

Based on the average sale price from the ALEXANDRIA, VA office

  • Monthly Principal & interest $1,740
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Default based on a 30-year fixed rate of 2.99% 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.


Elementary School Unknown Elementary School
Middle School Unknown Middle School
High School Unknown High School

Price History

8/14/2021 Listed $4,400,000
11/8/2021 6% - $4,150,000

Property vs Zip Code Average in 21620

AVG $680K
AVG $4,944
AVG 75
Year Built
AVG 1951
AVG 27
Data Provided by Walkscore ® not using MLS data


101 N Water Street Chestertown, MD is a Single Family Home for sale at $4150000 with 7440 sqft and a lot size of 0.94 Acres Acre(s). 101 N Water Street Chestertown has 6 bedrooms, 5 baths and was built in 1769. The property's zip code is 21620 which is in Chestertown, MD

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 2.99% 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.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided 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.