USAMDChestertownHistoric Chestertown106 S Queen St

106 S Queen St, Chestertown, MD

Name: 106 S Queen St, For Sale in Chestertown - eXp Realty
Brand: Chesapeake Real Estate Associates, LLC
SKU: MDKE2006152
Price: 865000 USD

House

For Sale

Listed price in listed location currency (USD).

$865,000

341

MLS® MDKE2006152

Key Facts
Description
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 2472 sqft

Garage Yes

Taxes $11,448

Days Active 43

Lot Size

Approx. Age 1750

Avg. Price Per Sqft $349

MLS® Number MDKE2006152

Property Address: 106 S Queen St, CHESTERTOWN, MD, 21620-1522

Average square foot calculated using Size range provided by listing agent.

Description

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.

MLS® NumberMDKE2006152

Laundry LevelMain

Central VacNo

FireplaceNo

Acreage

Exterior

GarageYes

Approx. Age1750

Basement

DrivewayElectric Vehicle Charging Station(s), Parking Space Conveys, Detached Garage, Off Street

Garage Spaces

Heat

A/C

Heating Fuel

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

Mar 19, 2026List Date

$865,000List Price

Home Appraisal

This property is estimated to sell between: $676,000 and $960,000.

Similar properties in this area sold on average for: $676,900

Expected to sell in 31 days. Similar properties sold in 74 days. This home has been on eXp Realty for 43 days.

The estimated sale price does not take into account many variables such as recent renovations, type of appliances, school district etc. To get a more accurate estimate please contact agent.

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Starting Address

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