106 Queen St S, Chestertown, MD 21620
Local realty services provided by:ERA OakCrest Realty, Inc.
106 Queen St S,Chestertown, MD 21620
$829,000
- 3 Beds
- 4 Baths
- 2,472 sq. ft.
- Single family
- Active
Listed by: maryn j. leclair
Office: chesapeake real estate associates, llc.
MLS#:MDKE2006152
Source:BRIGHTMLS
Price summary
- Price:$829,000
- Price per sq. ft.:$335.36
About this home
Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic District
The Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make historic homes so special. History is woven into every corner of the property—from the prominence of past owners down to the foundation, which contains the mast of a ship.
The only home downtown with such a generous private front courtyard framed by mature landscaping, vibrant seasonal gardens, brick herringbone paths, and mature trees that create a peaceful retreat just steps from town. Whether enjoying a quiet morning coffee, entertaining guests, or simply admiring the blooms, the outdoor spaces are truly a stand-out feature.
Approaching the home, guests are welcomed by a wide red front door, a traditional symbol of hospitality in early America, inviting visitors inside just as it has for centuries. Inside, approximately 2,472 square feet of thoughtfully preserved living space blends historic character with modern comfort. Original wide-plank hardwood floors, period moldings and built-in cabinetry, reflect the home's 18th-century origins, while updated kitchens, baths, and central air/heat provide the conveniences expected today.
To the right of the grand foyer, a cozy study lined with built-in bookshelves provides the perfect home office or library and could easily be converted into a first-floor bedroom for those seeking single-level living flexibility. A first floor full bathroom with walk in shower is located conveniently around the corner straight through the foyer.
To the left of the foyer and at the forefront of the home, the stunningly preserved parlor, featuring 12x12 wavy glass windows, original panel walls and stunning gas fireplace with pine panel surround, offers an elegant setting for entertaining guests or enjoying quiet evenings at home. Just beyond, the large dining room serves as a memorable gathering space, complete with another fireplace, built-in cabinetry, and a charming pop-out window seat overlooking the side gardens. Just beyond that is a chef's kitchen featuring updated appliances, abundant storage cabinetry, generous island workspace, and a soaring tapered tray ceiling that creates an airy and inviting atmosphere. The kitchen breakfast nook is highlighted by panoramic bay window wall.
Off the breakfast nook is a convenient half bath and steps to the side courtyard with pergola and a screened porch. The garage—another rarity in the Historic District—provides valuable storage and convenience.
Upstairs, the spacious primary suite blends historic character with thoughtful updates, featuring a practical double closet and an en-suite bath highlighted by distinctive MacKenzie-Childs tile floors and decorative vanity hardware. Two additional generously sized bedrooms and a full bathroom provide comfortable accommodations for guests.
Beyond its appeal as a private residence, it has proven itself as one of Chestertown's most successful Airbnb properties, generating approximately $32,000 in bookings last year. Whether you're seeking a full-time residence, weekend retreat, or income-producing investment, this property offers exceptional flexibility. Furniture is negotiable for a truly turnkey opportunity.
Step outside and enjoy everything that makes Chestertown so beloved. Stroll to art galleries, locally owned shops, restaurants, the farmers market, and waterfront parks along the Chester River. Enjoy annual traditions such as the Tea Party Festival, Downrigging Weekend, and Dickens of a Christmas, all just moments from your front door. Become the steward of a treasured landmark while enjoying the comfort, beauty, and lifestyle that have made it one of Chestertown's most admired homes for generations....
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Home facts
- Year built:1750
- Subdivision & Development:HISTORIC CHESTERTOWN
- Listing ID #:MDKE2006152
- Added:148 day(s) ago
- Updated:August 14, 2026 at 01:59 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
- Living area:2,472 sq. ft.
Heating and cooling
- Cooling:Ductless/Mini-Split
- Heating:Baseboard - Hot Water, Propane - Leased
Structure and exterior
- Roof:Shingle
- Year built:1750
- Building area:2,472 sq. ft.
- Lot area:0.14 Acres
- 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:$829,000
- Price per sq. ft.:$335.36
- 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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