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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

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Listed Aug 28, 2026

Updated 5 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

Interior Features

Bedrooms
4
Bathrooms
4
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.17 Acres

Other Property Details

Taxes
$9,815
Tax Frequency
Annually
55+/Senior Community
No
MLS provider logo

Listed by TTR Sotheby's International Realty
Listing Contact: 4103107835 

The IDX display contains information sourced from the Bright MLS, Inc. as of 9/16/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

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Data last updated on 9/16/2026 at 4:51 AM UTC

 

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