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114 W Chestnut Street , Saint Michaels, MD 21663

$1,195,000
  • 114 W Chestnut Street , Saint Michaels, MD 21663 Main Photo

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New to the Market
BEDS4 BATHS4 full SQUARE FEET3,528 MLS#MDTA2014898
STATUSACTIVE PROPERTY TYPEResidential - Single Family SCHOOLTALBOT COUNTY PUBLIC SCHOOLS

Property Description

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.

114 W Chestnut Street | MLS# MDTA2014898

This single family home located at 114 W Chestnut Street , Saint Michaels, MD 21663 is currently listed for sale with an asking price of $1,195,000. This property was built in 1850 and has 4 bedrooms and 4 full baths with 3528 sq. ft. W Chestnut Street is located within the TALBOT COUNTY PUBLIC SCHOOLS school district. Search Saint Michaels real estate on www.katiehallteam.com today.

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Property Features

Property Type: Residential - Single Family
Cooling: Central A/C
Fireplaces: 4
Fuel Type: Electric
Heating: Heat Pump(s)
Home Style: Traditional
Lot Size: 0.17 Acres
Roof Type: Architectural Shingle
Stories: 3.0
Taxes: $9,815
Year Built: 1850

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Oven/Range - Gas, Refrigerator, Washer, Water Heater, Water Heater - Tankless
Exterior: Frame
Exterior: Street Lights
Fireplace: Wood
Flooring: Ceramic Tile, Hardwood
Lot Dimensions: 0.17 Acre(S)
Municipality: St Michaels
Parking Notes: 2 Total Parking Spaces
Rooms: Living Room, Dining Room, Kitchen, Family Room, Foyer, Laundry, Office
Sewer: Public Sewer
SQFT Above Finished: 3528
SQFT Total Finished: 3528
Structure Type: Detached
Total Garage/Parking Spaces: 2
Utilities: Cable TV, Electric Available
Water: Public

Local Schools

School District: TALBOT COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: TTR Sotheby's International Realty
Agency Phone: 4107452596

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Estimated Payment

$ 3,826.01 per month $2,659.55 Principal & Interest $817.92 Property Tax $348.54 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 08/30/2026. The listing information on this page last changed on 08/30/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sun 08/30/2026 12:00:00 AM EST) or Bright MLS (last updated Sat 08/29/2026 11:48:51 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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The Katie Hall and Amanda Stevens Team
Katie Hall, Amanda Stevens, Jennifer McDowell, Kyle Stively, Diane Boyd, Jason Williams 

309 West Fourth Street, Quarryville, PA 17566
717-786-1300

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