106 Queen Street S
Chestertown, MD 21620

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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.

Features

• Property Type: Single Family Home
• Sub Type: Detached
• Listing Status: Active
• County/Area: Kent County
• Zip Code: 21620
• Year Built: 1750
• Subdivision/Neighborhood: Historic Chestertown
• School District: Kent County Public Schools
• Sq.Ft.: 2,472 sq ft
• Style: Colonial, Georgian
• Stories: 2 Story
• Bedrooms: 3
• Full Baths: 3
• Half Baths: 1
• Garage: 1 Car, Garage - Rear Entry
• # of Parking Spaces: 1
• Fireplace: Gas/Propane, 1
• Lot Size: 6098 sq ft lot
• Baths: 4
• View: Street, Garden/Lawn
• Zoning: RB
• Above Grade Finished Area: 2472
• Above Grade Finished Area Source: Assessor
• Above Grade Finished Area Units: Square Feet
• Appliances: Dishwasher, Disposal, Dryer, Instant Hot Water, Range Hood, Refrigerator, Oven/Range - Gas, Stainless Steel Appliances, Washer, Water Heater - Tankless
• Area Total: 2472
• Area Total Source: Assessor
• Assessment Year: 2026
• Below Grade Area Total Source: Assessor
• Below Grade Finished Area Source: Assessor
• Below Grade Finished Area Units: Square Feet
• Below Grade Unfinished Area Source: Assessor
• Below Grade Unfinished Area Units: Square Feet
• Builder Name: Bedingfield Hands
• City Town Tax: 3164
• City Town Tax Payment Frequency: Annually
• Construction Materials: Frame
• Cooling: Ductless/Mini-Split
• Cooling Fuel: Electric
• Country: US
• County Tax: 8284
• County Tax Payment Frequency: Annually
• Cross Street: Cross and Water
• Direction Faces: Northeast
• Directions: gps
• Door Features: Storm
• Electric: 200+ Amp Service
• Entry Level: 1
• Fencing: Picket
• Flooring: Wood
• Foundation Details: Crawl Space
• Heating: Baseboard - Hot Water
• Heating Fuel: Propane - Leased
• Historic: Yes
• Hot Water: Tankless, Propane
• In City Limits: Yes
• Interior Features: Breakfast Area, Built-Ins, Ceiling Fan(s), Crown Moldings, Formal/Separate Dining Room, Kitchen - Island, Wood Floors, Pantry
• Laundry Type: Main Floor, Dryer In Unit, Washer In Unit
• List: Living Room, Dining Room, Bedroom 2, Bedroom 3, Kitchen, Library, Foyer, Breakfast Room, Bedroom 1, Laundry, Bathroom 1, Bathroom 2, Bathroom 3, Half Bath
• Listing Locale: 200004363592
• Living Area Source: Assessor
• Location Type: Middle Of Block
• Lot Features: Front Yard, Landscaping, Rear Yard, SideYard(s)
• Lot Size Source: Assessor
• Lot Size Square Feet: 6000
• Lot Size Units: Square Feet
• Main Level Full Baths: 1
• Main Level Half Baths: 1
• Main Level Total Baths: 2
• Main Type: Residential
• Municipal Trash: Yes
• Num Detached Garage Spaces: 1
• Other Structures: Above Grade, Below Grade
• Ownership Interest: Fee Simple
• Parking Features: ElectricVehicleChargingStations, Parking Space Conveys
• Parking Types: Detached Garage, Off Street
• Patio And Porch Features: Patio, Screened
• Possession: 0-30 Days CD, 31-60 Days CD
• Property Condition: Excellent
• Road Frontage Size: 50
• Road Responsibility: City/County
• Road Surface Type: Black Top
• Roof: Shingle
• Sale Type: Standard
• Security Features: SecuritySystem
• Sewer: Public Sewer
• Tax Annual Amount: 11448
• Tax Total Finished Sq Ft: 2472
• Tax Year: 2025
• Total Actual Rent: 32000
• Total Public Open Houses: 2
• Total Stories: 2
• Total Taxes Payment Frequency: Annually
• Upper Level 1 Bedrooms: 3
• Upper Level 1 Full Baths: 2
• Upper Level 1 Total Baths: 2
• Upper Levels Total Baths: 2
• Upper Levels Total Bedrooms: 3
• Upper Levels Total Full Baths: 2
• Utilities: Propane, Above Ground
• Vacation Rental: Yes
• Water Source: Public
• Window Features: Storm, Screens, Wood Frame
• Year Built Effective: 1950
• Year Built Source: Assessor