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MLS: #MDKE2006152, Listed By: Maryn LeClair, Chesapeake Real Estate Associates, LLC, Source:Bright MLS

106 Queen Street

CHESTERTOWN, MD 21620
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Bed 3

Bed

Bath 4

Bath

SqFt2,472

Sqft

Acres0.14

Acre(Lot)

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.

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Detail Ic Property Details

Property Type : Residential

Price : $865,000

AD Id : 76701181

MLS Id : MDKE2006152

Beds : 3

Lot Size : 0.14 Acre

Living Area Size : 2,472

Year Built : 1750

Garage : 1

County : KENT

Subdivision: Historic Chestertown

  • Map Map

Map

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Feature Features

  • Bedroom Information

    Total beds: 3

    Bathroom Information

    Total Baths: 4 Full Baths: 3 Half Baths: 1

    Room Information

    Basement: Crawl Space
  • Flooring Information

    Wood
  • Roofing Information

    Shingle
  • Interior Features

    Ceiling Fan(s), Kitchen Island, Pantry, Built-in Features, Crown Molding Roof: Shingle Appliances: Gas Range, Gas Oven, Gas Water Heater, Washer, Dishwasher, Disposal, Dryer, Instant Hot Water, Range Hood, Refrigerator, Stainless Steel Appliance(s), Tankless Water Heater Laundry Features: Laundry Room, Main Level Window Features: Storm Window(s), Screens, Wood Frames
  • Heating & Cooling

    Has Heating: Yes Heating: Propane, Baseboard Has Cooling: Yes Cooling: Ceiling Fan(s), Ductless, Electric

  • Building Information

    Year Built: 1750 Building Area Total: 2472 Construction Materials: Frame Stories: 2 Patio And Porch Features: Patio, Screened Pool Features: None Private Pool: No View: Street, Garden

  • Lot Information

    Lot Size Acres: 0.14 Lot Size Source: Assessor Lot Size Square Feet: 6000 Lot Description: Front Yard, Back Yard

    Property Information

    Subdivision: HISTORIC CHESTERTOWN Source Property Type: Residential Postal Code Plus 4: 1522 Property SubType: Single Family Residence Direction Faces: Northeast Levels: Two Property Age: 276

  • Listing Price Information

    Listing Price: $865000

  • Tax Information

    Parcel Number: 1504018206 Tax Year: 2025 Annual Tax: $11448

  • Parking Information

    Parking Total: 1 Off Street, Electric Vehicle Charging Station(s), Garage, Detached

    Garage Information

    Has Garage: Yes Garage Space: 1

  • Utility Information

    Propane
  • Location Information

    Direction: gps WaterSource: Public Security Features: Security System
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
1904 Pondtown Road, Chestertown, MD, 21620 $265,000 3 1 1,967 1,967 SqFt
204 Double Creek Road, Chestertown, MD, 21620 $565,000 3 3 2,927 2,927 SqFt
240 Merganser Drive, Chestertown, MD, 21620 $399,000 3 2 1,120 1,120 SqFt
118 Grant Court, Chestertown, MD, 21620 $457,500 3 2 1,664 1,664 SqFt
109 Wilton Road, Chestertown, MD, 21620 $344,900 3 2 1,392 1,392 SqFt
215 Fairview Drive, Chestertown, MD, 21620 $425,000 3 3 1,784 1,784 SqFt
208 Central Drive, Chestertown, MD, 21620 $299,000 3 1 1,120 1,120 SqFt
704 Truslow Road, Chestertown, MD, 21620 $440,000 3 3 2,060 2,060 SqFt
101 Coleman Drive, Chestertown, MD, 21620 $524,900 3 3 2,268 2,268 SqFt
231 Richard Drive, Chestertown, MD, 21620 $1,150,000 5 3 2,956 2,956 SqFt

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ByOwner last updated this listing 06/12/2026 @ 23:31

MLS: MDKE2006152 LISTED BY: Maryn LeClair, Chesapeake Real Estate Associates, LLC 443-215-4663 SOURCE: Bright MLS

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