106 Queen St S, Chestertown, MD 21620
Local realty services provided by:Better Homes and Gardens Real Estate Cassidon Realty
106 Queen St S,Chestertown, MD 21620
$865,000
- 3 Beds
- 4 Baths
- 2,472 sq. ft.
- Single family
- Active
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
- Price per sq. ft.:$349.92
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....
Contact an agent
Home facts
- Year built:1750
- Listing ID #:MDKE2006152
- Added:14 day(s) ago
- Updated:April 03, 2026 at 10:19 AM
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:$865,000
- Price per sq. ft.:$349.92
- 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
New listings near 106 Queen St S
- Coming Soon
$695,000Coming Soon3 beds 2 baths10087 John Carvill Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006324Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY - New
$325,000Active3 beds 2 baths1,404 sq. ft.217 Philosophers Ter, CHESTERTOWN, MD 21620
MLS# MDKE2006332Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY - New
$115,000Active3 beds 1 baths910 sq. ft.108 Pine St, CHESTERTOWN, MD 21620
MLS# MDKE2006322Listed by: REAL BROKER, LLC - Coming Soon
$319,900Coming Soon2 beds 2 baths10584 Klamath Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006328Listed by: REAL BROKER, LLC - New
$435,000Active3 beds 2 baths1,588 sq. ft.201 Birch Run Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006316Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$339,900Pending3 beds 3 baths1,724 sq. ft.103 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006154Listed by: AMERICAN PREMIER REALTY, LLC- New
$3,000Active0.34 AcresCogar Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006304Listed by: ASHLAND AUCTION GROUP LLC - New
$55,000Active0.52 Acres144 Char Nor Manor Blvd, CHESTERTOWN, MD 21620
MLS# MDQA2016682Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY - New
$225,000Active0.87 AcresHaacke Drive Lot 3, CHESTERTOWN, MD 21620
MLS# MDKE2006274Listed by: SELECT LAND & HOMES, LLC - New
$250,000Active0.85 AcresScheeler Road Lot 2, CHESTERTOWN, MD 21620
MLS# MDKE2006290Listed by: SELECT LAND & HOMES, LLC