Date
Details
Price
Change
Source
4/02/2026
Listed
$865,000
—
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
*Open House Friday April 3rd 5-7pm and Saturday April 4th 10am-12pm *The Bedingfield Hands House, circa 1750, traces its routes back to pre-revolutionary times and has a story to tell. One of the few downtown homes to offer a large front courtyard, the property features beautifully landscaped gardens and a mature magnolia tree creating a private and welcoming outdoor retreat. Offering approximately 2,472 square feet, the home includes three generously sized bedrooms and three-and-a-half updated bathrooms with elegant details throughout, including crown moulding, original wide-plank hardwood floors, and timeless architectural charm. Major renovations completed in the 1950s -include a kitchen, laundry room, and baths-while preserving the home's historic integrity. Central heating and air conditioning provide comfortable modern living within this classic setting. The property is also one of the few downtown homes to include a garage. Currently operating as one of the most successful Airbnbs in the area with a strong rental history ($32K in bookings last year!), this property offers the best of both worlds-an ideal vacation home and a turn-key income-producing investment. Furniture is negotiable. Ideally located in the heart of Chestertown's historic district, the home is just steps from art galleries, gift shops, the local farmers market, and beloved annual events like the Chestertown Tea Party Festival, Downrigging Weekend, and the Dickens of a Christmas. The Chester River located just down the street offers endless opportunities for boating and waterfront recreation, while the town itself maintains a relaxed pace of life where history, culture, and community come together. A rare and remarkable offering, the Bedingfield Hands House now stands ready for its next owner to continue its story-preserving its past, enjoying its present, and carrying its legacy forward for generations to come.
Full Property Details
Full Property Details for 106 Queen Street S
General
- Price: $865,000
- Taxes: $11,448 (2025)
- Status: Active
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDKE2006152
- Updated: 4/2/2026
- Added to Site: 2 day(s) ago
Interior
- Rooms/Areas: Living Room, Dining Room, Bedroom 2, Bedroom 3, Kitchen, Library, Foyer, Breakfast Room, Bedroom 1, Laundry, Bathroom 1, Bathroom 2, Bathroom 3, Half Bath
- Interior Features: Breakfast Area, Built-Ins, Ceiling Fan(s), Crown Moldings, Formal/Separate Dining Room, Kitchen - Island, Wood Floors, Pantry
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Gas/Propane
- Appliances: Dishwasher, Disposal, Dryer, Instant Hot Water, Range Hood, Refrigerator, Oven/Range - Gas, Stainless Steel Appliances, Washer, Water Heater - Tankless
- Flooring: Wood
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
- Upper Floor Baths: 2
- Upper - Full Baths: 2
- Main Floor Baths: 2
- Main - Full Baths: 1
- Main - 1/2 Baths: 1
Bedrooms
- Total Bedrooms: 3
- Bedrooms Upper: 3
Other Rooms
- Laundry: Main Floor, Dryer In Unit, Washer In Unit
Additional Information
- Security/Safety: Security System
Exterior
- Porch/Patio/Deck: Patio(s), Screened
Parking
- Garage: Yes
- Garage Spaces: 1
- Total Spaces: 1
- Parking Features: Electric Vehicle Charging Station(s), Parking Space Conveys
- Parking Type: Detached Garage, Off Street
- Garage Description: Garage - Rear Entry
Location
- Municipality: Chestertown
- County: KENT
- Subdivision: HISTORIC CHESTERTOWN
- Cross Streets: Cross and Water
- Driving Directions: gps
- Direction Faces: Northeast
- Location Details: Middle Of Block
- Historic District: Yes
- City Limits: Yes
School Information
- School District: Kent County Public Schools
Heating & Cooling
- Cooling Type: Ductless/Mini-Split
- Cooling Fuel: Electric
- Heating Type: Baseboard - Hot Water
- Heating Fuel: Propane - Leased
- Water Heater: Tankless, Propane
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Propane, Above Ground
Structural Information
- Architectural Style: Colonial, Georgian
- Structure Type: Detached
- Builder: Bedingfield Hands
- Construction: Frame
- Foundation: Crawl Space
- Roof: Shingle
- Windows: Storm, Screens, Wood Frame
- Doors: Storm
- Entry Floor Number: 1
- Stories Description: Main, Upper 1
- Square Feet: 2,472
- Sq. Ft. Source: Assessor
- Living Area: 2,472 Sq. Ft.
- Finished Above Grnd: 2,472 Sq. Ft.
- Year Built: 1750
- Year Built Source: Assessor
- Property Condition: Excellent
Lot Features
- Property View: Street, Garden/Lawn
- Lot Size (Acres): 0.14
- Lot Size (Sq. Ft.): 6,000
- Lot Size Source: Assessor
- Frontage Feet: 50
- Street/Road Desc.: Black Top
- Zoning: RB
- Lot Description: Front Yard, Landscaping, Rear Yard, SideYard(s)
- Fencing (Description): Picket
Financial Considerations
- Price Per Sq. Ft.: $349.92
- Assessment Year: 2026
- City/TownTax: $3,164
- City/TownTax Freq: Annually
- County Tax: $8,284
- County Tax Freq: Annually
- Tax w/Assessment: $743,100
- Tax Amount: $11,448
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 2472
Disclosures and Reports
- Ownership: Fee Simple
Listed by Chesapeake Real Estate Associates, LLC, Maryn J. LeClair
We Value Your Privacy
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Listing agent
— 106 Queen Street S —
Maryn J. LeClair
Chesapeake Real Estate Associates, LLC
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 106 Queen Street S
School District:Kent County Public Schools
| Name | Grades | Distance |
|---|---|---|
H. H. Garnett Elementary School 320 Calvert Street, Chestertown, MD 21620 | PK-5 | 0.4 mi |
Kent County Middle School 402 East Campus Avenue, Chestertown, MD 21620 | 6-8 | 0.6 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 106 Queen Street S
Tax History
Tax History for 106 Queen Street S
Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,389
4%
$407,700
4%
2024
$6,156
9%
$392,833
4%
2023
$5,654
—
$377,967
4%
2022
$5,654
—
$363,100
—
2020
$5,680
—
$362,767
—
2020
$5,663
1%
$362,100
—
2019
$5,627
3%
$362,067
—
2018
$5,445
—
$362,033
—
2017
$5,444
307%
$362,000
—
2016
$1,339
-75%
$362,000
—
2015
$5,444
-1%
$362,000
-1%
2014
$5,526
—
$367,400
—
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 106 Queen Street S
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Listed by Lisa Knotts (302) 362-6365
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106 Queen Street S, Chestertown, MD 21620 (MLS# MDKE2006152) is a Single Family property with 3 bedrooms, 3 full bathrooms and 1 partial bathroom. 106 Queen Street S is currently listed for $865,000 and was received on April 02, 2026. Want to learn more about 106 Queen Street S? Do you have questions about finding other Single Family real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.