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4 Beds
4 Baths
3,528 sqft

$1,195,000

114 W Chestnut Street, St Michaels MD, 21663

Price per sqft$338.72
Built in1850
Property size3,528 sqft
Property typeResidential

Overview

Active

Listed Aug 28, 2026

Updated 10 days ago

Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant harbor, boutique shops, and award-winning restaurants. Enter from the wide, covered front porch - ideal for morning coffee or greeting neighbors - into a grand, elongated foyer that sets a welcoming tone. The interior features gorgeous hardwood floors throughout, seamlessly connecting the bright living spaces. This home offers four spacious bedrooms, generously sized bathrooms, and ample storage, providing comfort for family and guests alike. The rear yard is a private retreat designed for both relaxation and entertaining. Tucked into the lush landscaping (which includes an in-ground irrigation system) is a fully finished, detached accessory building. This versatile, light-filled structure is perfect for a dedicated craft studio, hobby workshop, private home office, or fitness room. This property also includes rare, highly coveted off-street parking. Situated just steps from San Domingo creek and less than a block from Talbot Street, the house provides quick access to the waterfront park/kayak launch and the nature trail as well to the town's maritime attractions, local ice cream parlors, and fine dining. An 1850 historic treasure in a premier in-town location doesn't come along often-schedule your private tour today and make the magic of the Eastern Shore your reality.

$7,950/mo

Est. mortgage payment based on a $1,195,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
MDTA2014898
Available since
August 28, 2026

Interior Features

Bedrooms
4
Bathrooms
4
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.17 Acres

Other Property Details

Taxes
$9,815
Tax Frequency
Annually

 Courtesy of Robert Lacaze | TTR Sotheby's International Realty

Based on information from DASH - Sotheby's International Realty (SIR) as of 9/11/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. The display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent. 

©2026 DASH - Sotheby's International Realty (SIR). All rights reserved. 

Data last updated 10:09 AM UTC, 9/11/2026

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