$1,350,000

114 W CHESTNUT ST, Saint Michaels, MD 21663

  • 4 beds |
  • 5 baths |
  • 3,528 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1850
  • Property Lot Size Icon7,405sqft lot
  • Property Parking Icon —— car garage
  • Property Price Per Square Feet Icon $383/sqft
  • Property List Date Icon Listed 16 days ago

Property Description

Ideally located in the heart of the St. Michaels Historic District, this beautifully maintained three-story home offers exceptional walkability just a half block from the waterfront, scenic walking trail, public park and kayak launch, as well as the shops, restaurants, and other amenities that make St. Michaels such a sought-after place to live. A welcoming front porch introduces an inviting interior with hardwood floors, multiple comfortable living areas, and four wood-burning fireplaces that add warmth and character throughout. The spacious layout includes four bedrooms and four and one-half baths, providing flexibility for everyday living and hosting guests, along with a dedicated office, custom built-ins, and abundant storage. Outside, the beautifully landscaped and fenced yard offers privacy and space for outdoor enjoyment, complemented by a detached studio/workshop ideal for creative pursuits or hobbies. Off-street parking adds convenience in this prime in-town setting. With a prime location, generous living and storage space, and historic charm, this distinctive property represents exceptional value in the heart of St. Michaels.

Listing Status:
Active
Date Added:
March 17, 2026
Data Last Updated:
April 2, 2026 at 8:20PM
Listing Office:
Benson & Mangold, LLC : 4107450415
Listing Agent:
Winifred C Cowee : 4103100208
MLS ID:
MDTA2013116
  • Rooms: Living RoomDining RoomPrimary BedroomBedroom 2Bedroom 3Bedroom 4KitchenFamily RoomGreat RoomLaundryMud RoomOfficeBathroom 1Bathroom 2Bathroom 3Primary BathroomHalf Bath
  • Appliances: DishwasherDisposalDryerExhaust FanMicrowaveOven/Range - GasWasherWater Heater - TanklessWaterHeaterRefrigerator
  • Flooring: HardwoodCeramic tile
  • A/C: Other
  • Heating: Heat Pump(s)Electric
  • Fireplace: WoodFireplaceFireplaces: 3
  • Disability Feature: None
  • General: Street LightsAbove GradeBelow Grade
  • Style: Traditional
  • Roofing: Architectural Shingle
  • General: Frame3Crawl Space
  • Originating MLS: BRIGHT_MAIN
  • School District: TALBOT COUNTY PUBLIC SCHOOLS
  • County: TALBOT-MD
  • Zoning: R-12102064200
  • Water: Public
  • Sewer: Public Sewer
  • Source: BRIGHT_MAIN

This listing courtesy of Winifred C Cowee , Benson & Mangold, LLC

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

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Location

Schools Nearby

S

St. Michaels Elementary School

100 Seymour Ave, Saint Michaels, MD, 21663

Grades PK-5

0.36 miles away

S

St. Michaels Middle/High School

200 Seymour Ave, Saint Michaels, MD, 21663

Grades 6-12

0.45 miles away

S

St. Michaels Middle/High School

200 Seymour Ave, Saint Michaels, MD, 21663

Grades 6-12

0.45 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.

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#MDTA2013310 - Meredith Fine Properties