106 QUEEN ST S, Chestertown, MD 21620

• 3 beds |
• 4 baths |
• 2,472 sqft

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.

Listing Status:

Coming Soon

Date Added:

April 2, 2026

Data Last Updated:

March 24, 2026 at 12:18AM

Listing Office:

Chesapeake Real Estate Associates, LLC : 4432154663

Listing Agent:

Maryn J. LeClair : 4434802837

MLS ID:

MDKE2006152

Interior

• General: Breakfast AreaBuilt-InsCeiling Fan(s)Crown MoldingsFormal/Separate Dining RoomKitchen - IslandWood FloorsPantry
• Rooms: Living RoomDining RoomBedroom 2Bedroom 3KitchenLibraryFoyerBreakfast RoomBedroom 1LaundryBathroom 1Bathroom 2Bathroom 3Half Bath
• Appliances: DishwasherDisposalDryerInstant Hot WaterRange HoodRefrigeratorOven/Range - GasStainless Steel AppliancesWasherWater Heater - Tankless
• Laundry: Main FloorDryer In UnitWasher In Unit
• Flooring: Wood
• A/C: Ductless/Mini-Split
• Heating: Baseboard - Hot WaterPropane - Leased
• Fireplace: Gas/PropaneFireplaceFireplaces: 1
• Disability Feature: None

Exterior

• General: Above GradeBelow Grade
• Style: ColonialGeorgian
• Other Structures: ScreenedPatio
• Parking: ElectricVehicleChargingStationsParking Space Conveys

Construction

• Roofing: Shingle
• Windows: StormScreensWood frame
• General: Frame2Crawl Space

Location

• Road/Access: 50
• Originating MLS: BRIGHT_MAIN
• School District: KENT COUNTY PUBLIC SCHOOLS
• County: KENT-MD

Lot

• Zoning: RB1504018206
• View: StreetGarden/Lawn
• Fencing: Picket

Utilities

• Utilities: PropaneAbove ground200 amp service
• Water: Public
• Sewer: Public Sewer

Financial

• Source: BRIGHT_MAIN