SoldAug 14, 2019

Listed by Thomas Crouch from Benson & Mangold, LLC

Source: Bright MLS #MDTA135066

106 E Chestnut St, St. Michaels, MD, 21663

$582,000

3
2
1
2282 sq. ft.
9600 sq. ft.

SingleFam

30+ days on the market

Sold: Aug 14, 2019

What's around 106 E Chestnut St

About this property

Located on one of the town's prettiest, tree-lined streets, mid-way between the center of town and the harbor, this circa 1830 home is one of St. Michaels' historic treasures. Sited on one of the largest lots on the street (double lot), the house was expanded in 1870 and again in 2002, when a wonderful conservatory/family room was added. This is the owner's favorite room in the house! The conservatory overlooks the side and back yard, which has been landscaped with walkways, patio, pergola, magnificent perennial gardens and flowering trees. There is always something in bloom, from early spring through late fall. A variety of birds, including humming birds, appreciate the flowers, too! The house has been tastefully updated, with care to preserve the 19th century charm. The house features bright, spacious rooms, beautiful wood floors and a modern kitchen, which is centrally located between the breakfast room and the conservatory. This is a comfortable, well-designed home! There is an inviting Victorian porch in front, where you will want to sit and relax, just as people did 100 years ago. In back, you will find a detached 1-car garage plus a separate studio, which could function as an office, project room or workshop. Always lovingly maintained, the house, garage and studio have just been freshly painted.

Looking for more information on 106 E Chestnut St?

Explore comparables, sales history and growth for this property.
Learn more

Similar properties sold nearby

SoldMay 22, 2026
$2,435,000
24830 Deepwater Point Dr
Talbot County MD 21663
3
3
4
Single-Family
Listing courtesy of Long & Foster Real Estate, Inc. and Benson & Mangold, LLC
SoldMay 1, 2026
$740,000
23869 Mt Misery Rd
Talbot County MD 21663
3
2
2
Single-Family
Listing courtesy of Benson & Mangold, LLC and Unrepresented Buyer Office
SoldApr 30, 2026
$785,000
24822 Swan Road
St. Michaels MD 21663
3
3
2
Single-Family
Listing courtesy of Benson & Mangold, LLC and Coldwell Banker Waterman Realty

Other properties sold by Benson & Mangold, LLC

SoldMay 29, 2026
$345,000
20/24354 Widgeon Place
St. Michaels MD 21663
2
3
1
Townhouse
Listing courtesy of TTR Sotheby's International Realty and Benson & Mangold, LLC
SoldMay 27, 2026
$218,000
927 Susquehanna Rd
Madison MD 21648
3
1
4
Single-Family
Listing courtesy of Keller Williams Select Realtors of Cambridge and Benson & Mangold, LLC
SoldMay 18, 2026
$425,000
111 Glory Avenue
St. Michaels MD 21663
2
2
2
Single-Family
Listing courtesy of Benson & Mangold, LLC and Chesapeake Real Estate Associates, LLC

Browse properties sold in nearby areas

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 Benson & Mangold, LLC 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.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Email
© 2026 RateMyAgent