Coldwell Banker Home Page
Local Realty Service Provided By: Coldwell Banker Hearthside
Property view
Listing view 2
Listing view 3

106 Queen St S, 
Chestertown, MD 21620

$865,000


3

Beds


4

Baths


2,472

Sq Ft


Single Family

Coming Soon

Listed by

Maryn J. Leclair

Chesapeake Real Estate Associates, LLC.

Last updated:

March 28, 2026, 01:37 PM

MLS#

MDKE2006152

Source:

BRIGHTMLS

About This Home

106 Queen St S

*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.

Home Facts

Single Family

4 Baths

3 Bedrooms

Built in 1750

Price Summary

865,000

$349 per Sq. Ft.

MLS #:

MDKE2006152

Last Updated:

March 28, 2026, 01:37 PM

Added:

10 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

3

Interior

Living Area:

2,472 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial, Georgian

Building Area:

2,472 Sq. Ft.

Year Built:

1750


Lot

Lot Size (Sq. Ft):

6,098


Finances & Disclosures

Finances

Price:

$865,000

Price per Sq. Ft:

$349 per Sq. Ft.

Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.
See this home in person
106 Queen St S
Attend an upcoming open house
Fri, Apr 3
05:00 PM07:00 PM
Sat, Apr 4
10:00 AM12:00 PM

Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.

Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.