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
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
New photos just added—capturing the truly one-of-a-kind gardens now in full bloom! This is a property you need to experience in person to fully appreciate the timeless character and breathtaking setting of this remarkable legacy home. The Bedingfield Hands House, circa 1750, traces its roots 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:66 day(s) ago
- Updated:May 25, 2026 at 01:42 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:$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
- New
$285,000Active3 beds 1 baths1,248 sq. ft.956 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006394Listed by: DOUG ASHLEY REALTORS, LLC
$1,500,000Pending5 beds 3 baths2,700 sq. ft.7761 Broad Neck Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006542Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY- Coming Soon
$3,000,000Coming Soon3 beds 4 baths25440 Learman Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006468Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY - New
$55,000Active0.7 AcresMap 36 Parcel 80 Watertower Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006592Listed by: DOUG ASHLEY REALTORS, LLC - Coming SoonOpen Sat, 12 to 2pm
$457,500Coming Soon3 beds 2 baths118 Grant Ct, CHESTERTOWN, MD 21620
MLS# MDQA2017356Listed by: RE/MAX EXECUTIVE - New
$138,000Active3 beds 2 baths1,666 sq. ft.127 Wood Duck Ln, CHESTERTOWN, MD 21620
MLS# MDQA2017354Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY - New
$339,900Active3 beds 3 baths1,896 sq. ft.102 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006586Listed by: LONG & FOSTER REAL ESTATE, INC. - Coming Soon
$1,450,000Coming Soon4 beds 4 baths22470 Fairgale Farm Ln, CHESTERTOWN, MD 21620
MLS# MDKE2006502Listed by: GUNTHER-MCCLARY REAL ESTATE - New
$185,000Active3 beds 2 baths1,136 sq. ft.423 Calvert St, CHESTERTOWN, MD 21620
MLS# MDKE2006578Listed by: COMPASS - New
$6,000Active0.69 Acres23683 L Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006580Listed by: ALEX COOPER AUCTIONEERS, INC.