Property Search

Save
Ask
Tour
Hide
Share
$1,195,000
16 Days On Site

114 W CHESTNUT STREET
ST MICHAELS, MD 21663

For Sale|Single Family Residence|Active
4
Beds
4
Total Baths
4
Full Baths
3,528
SqFt
$339
/SqFt
1850
Built
County:
TALBOT
Listing courtesy of TTR Sotheby's International Realty
Call Now: (703) 898-3565
Is this the listing for you? We can help make it yours.
(703) 898-3565
114 W CHESTNUT STREET114 W CHESTNUT STREET114 W CHESTNUT STREET114 W CHESTNUT STREET
Save
Ask
Tour
Hide
Share

Mortgage Calculator

Monthly Payment (Est.)

$5,452
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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.

Save
Ask
Tour
Hide
Share
Listing Snapshot
Price 
$1,195,000
Days On Site 
16 Days
Bedrooms 
4
Inside Area (SqFt) 
3,528 sqft
Total Baths 
4
Full Baths 
4
Partial Baths 
N/A
Lot Size 
0.17 Acres
Year Built 
1850
MLS® Number 
MDTA2014898
Status 
Active
Property Tax 
$9,815
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Assessor
Friends & Family
Recent Activity
3 days agoListing updated with changes from the MLS®
2 weeks agoListing first seen on site
General Features
Acres 
0.17
Levels 
Three Or More
Parking 
Off StreetOn StreetAlley AccessDriveway
Parking Spaces 
2
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
Special Circumstances 
Standard
SqFt Above 
3528
SqFt Total 
3528
Style 
Traditional
Utilities 
Cable AvailableElectricity Available
Water Source 
Public
Zoning 
R-1
Interior Features
Appliances 
Gas RangeGas OvenElectric Water HeaterDishwasherDisposalDryerExhaust FanMicrowaveRefrigeratorWasherWater HeaterTankless Water Heater
Basement 
Crawl Space
Cooling 
Central AirElectric
Fireplace 
Yes
Fireplace Features 
Wood Burning
Fireplaces 
4
Flooring 
Ceramic TileHardwood
Heating 
Exhaust FanElectricHeat Pump
Laundry Features 
Laundry Room
Dining Room 
Level - Main
Family Room 
Level - Main
Foyer 
Level - Main
Kitchen 
Level - Main
Laundry 
Level - Main
Living Room 
Level - Main
Office 
Level - Main
Save
Ask
Tour
Hide
Share
Exterior Features
Construction Details 
Frame
Pool Features 
Community
Roof 
Shingle
Community Features
Community Features 
PoolStreet Lights
School District 
TALBOT COUNTY PUBLIC SCHOOLS
Schools
School District
TALBOT COUNTY PUBLIC SCHOOLS
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Listing courtesy of TTR Sotheby's International Realty



The real estate listing information is 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 consumer may be interested in purchasing. Any information relating to real estate for sale or lease referenced on this web site comes from the Internet Data Exchange (IDX) program of the Bright MLS. This web site references real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties in listings may have been sold or may no longer be available. The data contained herein is copyrighted by Bright MLS and is protected by all applicable copyright laws. Any unauthorized collection or dissemination of this information is in violation of copyright laws and is strictly prohibited. Copyright © 2020 Bright MLS. All rights reserved.

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
Save
Ask
Tour
Hide
Share
Popular areas we serve

Northern Virginia Communities

  1. Aldie
  2. Alexandria
  3. Annandale
  4. Arlington
  5. Ashburn
  6. Bluemont
  7. Brambleton
  8. Bristow
  9. Broadlands
  10. Burke
  11. Centreville
  12. Chantilly
  13. Fairfax
  14. Falls Church
  15. Gainesville
  16. Great Falls
  17. Herndon
  18. Leesburg
  19. Manassas
  20. Manassas Park
  21. McLean
  22. Middleburg
  23. Oakton
  24. Reston
  25. South Riding
  26. Springfield
  27. Sterling
  28. Stone Ridge
  29. Vienna
  30. Winchester
  31. Woodbridge

Browse by Area

Start A Custom Search