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114 W Chestnut St, 
St Michaels, MD 21663

$1,195,000


4

Beds


4

Baths


3,528

Sq Ft


Single Family

Active

Listed by

Robert D Lacaze

Ttr Sotheby'S International Realty

Last updated:

August 28, 2026, 06:49 PM

MLS#

MDTA2014898

Source:

BRIGHTMLS

About This Home

114 W Chestnut St

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.

Home Facts

Single Family

4 Baths

4 Bedrooms

Built in 1850

Subdivision & Development:

NONE AVAILABLE

Price Summary

1,195,000

$338 per Sq. Ft.

MLS #:

MDTA2014898

Last Updated:

August 28, 2026, 06:49 PM

Added:

21 hour(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

4

Interior

Living Area:

3,528 Sq. Ft.


Structure

Structure

Architectural Style:

Traditional

Building Area:

3,528 Sq. Ft.

Year Built:

1850


Lot

Lot Size (Sq. Ft):

7,405


Finances & Disclosures

Finances

Price:

$1,195,000

Price per Sq. Ft:

$338 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
114 W Chestnut St
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Sun, Aug 30
01:00 PM03:00 PM

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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.