Active

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

106 Queen Street

CHESTERTOWN, MD 21620
Mark as Favorite
Bed 3

Bed

Bath 4

Bath

SqFt2,472

Sqft

Acres0.14

Acre(Lot)

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 q uiet 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.

Read More Expand

Detail Ic Property Details

Property Type : Residential

Price : $829,000

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

Map What's Nearby

Map Nearby Areas

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 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: $829000

  • 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
Sell a home like this and save $49,241 Find out How

How much is this property worth?

Curious about this home's true market value? Use our free Home Evaluation Tool to instantly get a personalized Comparative Market Analysis (CMA) report. Make smarter, data-driven decisions before you buy.

Images
Loading, please wait...

Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
Preston Lane, Chestertown, MD, 21620 $525,000 3 3 2,824 2,824 SqFt
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 $365,000 3 2 1,120 1,120 SqFt
222 Dutchess Road, Chestertown, MD, 21620 $320,000 3 2 1,096 1,096 SqFt
517 Round Top Road, Chestertown, MD, 21620 $299,900 3 1 1,248 1,248 SqFt
101 Coleman Drive, Chestertown, MD, 21620 $519,900 3 3 2,268 2,268 SqFt
201 River Road, Chestertown, MD, 21620 $629,900 3 2 2,430 2,430 SqFt
103 Maple Avenue, Chestertown, MD, 21620 $615,000 4 3 4,536 4,536 SqFt
210 N Queen Street, Chestertown, MD, 21620 $735,000 4 3 2,730 2,730 SqFt

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which ByOwner participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright © 2026 Bright MLS. All rights reserved.

ByOwner last updated this listing 07/28/2026 @ 11:10

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

Homes around $829,000

Selling? Save $49,241 when you sell a home like this

Tour with a ByOwner Agent