106 Queen St S, Chestertown, MD 21620
Local realty services provided by:CENTURY 21 Charles Smith Agency, Inc.
106 Queen St S,Chestertown, MD 21620
$865,000
- 3 Beds
- 4 Baths
- - sq. ft.
- Single family
- Coming Soon
Upcoming open houses
- Fri, Apr 0305:00 pm - 07:00 pm
- Sat, Apr 0410:00 am - 12:00 pm
Listed by: maryn j. leclair
Office: chesapeake real estate associates, llc.
MLS#:MDKE2006152
Source:BRIGHTMLS
Price summary
- Price:$865,000
About this home
*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....
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Home facts
- Year built:1750
- Listing ID #:MDKE2006152
- Added:1 day(s) ago
- Updated:March 20, 2026 at 01:36 PM
Rooms and interior
- Bedrooms:3
- Total bathrooms:4
- Full bathrooms:3
- Half bathrooms:1
- Flooring:Wood
- Dining Description:Dining Room, Formal/Separate Dining Room
- Bathrooms Description:Bathroom 1, Bathroom 2, Bathroom 3, Half Bath
- Kitchen Description:Breakfast Area, Built-Ins, Crown Moldings, Dishwasher, Disposal, Instant Hot Water, Kitchen - Island, Oven/Range - Gas, Pantry, Range Hood, Refrigerator, Stainless Steel Appliances, Water Heater - Tankless
Heating and cooling
- Cooling:Ductless/Mini-Split
- Heating:Baseboard - Hot Water, Propane - Leased
Structure and exterior
- Roof:Shingle
- Year built:1750
- Lot Features:Front Yard, Landscaping, Middle Of Block, Rear Yard, SideYard(s)
- Architectural Style:Colonial, Georgian
- Construction Materials:Frame
- Exterior Features:Patio(s), Screened
- Foundation Description:Crawl Space
- Levels:2 Stories
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$865,000
- Tax amount:$11,448 (2025)
Features and amenities
- Laundry features:Dryer, Dryer In Unit, Laundry, Washer, Washer In Unit
- Amenities:200+ Amp Service, Above Ground Utilities, Built-Ins, Ceiling Fan(s), Crown Moldings, Security System, Storm Windows
Parking
- Parking description:Detached Garage, Electric Vehicle Charging Station(s), Garage - Rear Entry, Off Street, Parking Space Conveys
- Garage:Yes
- Garage spaces:1
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