Change Real Estate Presents:

106 Queen Street
Chestertown MD 21620

For Sale: $865,000.00 Active

List Date: 2026-04-02

Chestertown
3 bedrooms
4 bathrooms
2,472 build ft2
6,000 land ft2

About This Property

*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.

Listing Agent: Maryn J. LeClair. Chesapeake Real Estate Associates, LLC 443-480-2837 marynleclair@chesapeakerea.com

Property Features

Location Information
County:
Subdivision: HISTORIC CHESTERTOWN
click to open map in a new window
Interior Features
Appliances: Dishwasher, Disposal, Dryer, Instant Hot Water, Range Hood, Refrigerator, Oven/Range - Gas, Stainless Steel Appliances, Washer, Water Heater - Tankless
Interior: Breakfast Area, Built-Ins, Ceiling Fan(s), Crown Moldings, Formal/Separate Dining Room, Kitchen - Island, Wood Floors, Pantry
Laundry:
Furnished: None
Flooring: Wood
Water: Public
Cooling: Ductless/Mini-Split
Heating: Baseboard - Hot Water
Fireplaces: 1
Windows: Storm, Screens, Wood Frame
Utilities: Propane, Above Ground
Sewer: Public Sewer
Rooms
Room Type: Bedroom 1
Level: Upper 1
Room Type: Bathroom 2
Level: Upper 1
Room Type: Bedroom 2
Level: Upper 1
Room Type: Bedroom 3
Level: Upper 1
Room Type: Bathroom 3
Level: Upper 1
Room Type: Foyer
Features: Flooring - HardWood
Level: Main
Room Type: Bathroom 1
Level: Main
Room Type: Library
Level: Main
Room Type: Living Room
Level: Main
Room Type: Dining Room
Level: Main
Room Type: Kitchen
Features: Kitchen - Country
Level: Main
Room Type: Breakfast Room
Level: Main
Room Type: Laundry
Level: Main
Room Type: Half Bath
Level: Main
Exterior Features
Year Built: 1750
Subdivision Name: Historic Chestertown
Parking: ElectricVehicleChargingStations, Parking Space Conveys
Garage Spaces: 1.0
Schools
Elementary School: None
Junior High School: None
High School: None

IDXListing Courtesy of Maryn J. LeClair. Chesapeake Real Estate Associates, LLC 443-480-2837 marynleclair@chesapeakerea.com

Property Photos [Click to enlarge]

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