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Under contract
    • $1,195,000

    114 W Chestnut St, St Michaels, MD 21663

    4beds
    3,528sqft
    : 
    $8,214/mo
    Get pre-qualified
    Single Family Residence
    Built in 1850
    7,200 Square Feet Lot
    $1,144,100 Zestimate®
    $339/sqft
    $-- HOA

    What's special

    Grand elongated foyerAmple storageIn-ground irrigation systemMultiple built-insClassic architectural detailsGorgeous hardwood floors throughoutBright living spaces
    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.
    39 days
    719
    34

    Zillow last checked:

    Listing updated:

    Listed by:

    Robert Lacaze 410-310-7835,

    TTR Sotheby's International Realty 410-745-2596

    Source: Bright MLS,MLS#: MDTA2014898MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 4
      • Main level bathrooms: 1
      Rooms
      • Room types: Living Room, Dining Room, Kitchen, Family Room, Foyer, Laundry, Office
      Dining room
      • Level: Main
      Family room
      • Level: Main
      Foyer
      • Level: Main
      Kitchen
      • Level: Main
      Laundry
      • Level: Main
      Living room
      • Level: Main
      Office
      • Level: Main
      Heating
      • Heat Pump, Electric
      Cooling
      • Central Air, Electric
      Appliances
      • Included: Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Oven/Range - Gas, Refrigerator, Washer, Water Heater, Tankless Water Heater, Electric Water Heater
      • Laundry: Laundry Room
      Features
      • Flooring: Ceramic Tile, Hardwood
      • Has basement: No
      • Number of fireplaces: 4
      • Fireplace features: Wood Burning
      Interior area
      • Total structure area: 3,528
      • Total interior livable area: 3,528 sqft
      • Finished area above ground: 3,528
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 2
      • Parking features: Alley Access, On Street, Off Street, Driveway
      • Uncovered spaces: 2
      Accessibility
      • Accessibility features: None
      Features
      • Levels: Three
      • Stories: 3
      • Exterior features: Street Lights
      • Pool features: Community
      • Waterfront features: Cove
      Lot
      • Size: 7,200 Square Feet
      Details
      • Additional structures: Above Grade, Below Grade
      • Parcel number: 2102064200
      • Zoning: R-1
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Traditional
      • Property subtype: Single Family Residence
      Materials
      • Frame
      • Foundation: Crawl Space
      • Roof: Architectural Shingle
      Condition
      • Excellent
      • New construction: No
      • Year built: 1850

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Connected, Electricity Available

      Community & HOA

      Community
      • Subdivision: None Available
      HOA
      • Has HOA: No
      Location
      • Region: St Michaels
      • Municipality: St Michaels

      Financial & listing details

      • Price per square foot: $339/sqft
      • Tax assessed value: $850,067
      • Annual tax amount: $9,815
      • Date on market: 8/28/2026
      • Listing agreement: Exclusive Right To Sell
      • Listing terms: Cash,Conventional
      • Exclusions: Shelving In Shed
      • Ownership: Fee Simple

        Estimated market value

        $1,144,100

        $1.09M - $1.20M

        $3,669/mo

        Price history

        DateEventPrice
        9/27/2026Contingent$1,195,000$339/sqft
        Source: Bright MLS #MDTA2014898 Report a problem
        8/28/2026Listed for sale$1,195,000$339/sqft
        Source: Bright MLS #MDTA2014898 Report a problem
        8/25/2026Listing removed$1,195,000$339/sqft
        Source: Bright MLS #MDTA2013116 Report a problem
        6/12/2026Price change$1,195,000-7%$339/sqft
        Source: Bright MLS #MDTA2013116 Report a problem
        5/29/2026Price change$1,285,000-4.8%$364/sqft
        Source: Bright MLS #MDTA2013116 Report a problem
        3/17/2026Listed for sale$1,350,000+110.9%$383/sqft
        Source: Bright MLS #MDTA2013116 Report a problem
        7/15/2020Sold$640,000-3%$181/sqft
        Source: Public Record Report a problem
        5/20/2020Pending sale$660,000$187/sqft
        Source: Chesapeake Bay Real Estate Plus, LLC #MDTA137092 Report a problem
        3/21/2020Price change$660,000-2.2%$187/sqft
        Source: Chesapeake Bay Real Estate Plus, LLC #MDTA137092 Report a problem
        3/13/2020Price change$675,000-3.4%$191/sqft
        Source: Chesapeake Bay Real Estate Plus, LLC #MDTA137092 Report a problem
        2/21/2020Price change$699,000-1.5%$198/sqft
        Source: Chesapeake Bay Real Estate Plus, LLC #MDTA137092 Report a problem
        2/7/2020Price change$710,000-1.1%$201/sqft
        Source: Chesapeake Bay Real Estate Plus, LLC #MDTA137092 Report a problem
        1/8/2020Listed for sale$718,000+19.9%$204/sqft
        Source: Chesapeake Bay Real Estate Plus, LLC #MDTA137092 Report a problem
        7/7/2017Sold$599,000$170/sqft
        Source: Public Record Report a problem
        4/27/2017Pending sale$599,000$170/sqft
        Source: Long & Foster Real Estate, Inc. #TA9789211 Report a problem
        4/8/2017Price change$599,000-9.1%$170/sqft
        Source: Long & Foster Real Estate, Inc. #TA9789211 Report a problem
        3/10/2017Price change$659,000-2.9%$187/sqft
        Source: Long & Foster Real Estate, Inc. #TA9789211 Report a problem
        3/8/2017Listing removed$3,000$1/sqft
        Source: Long & Foster Real Estate, Inc. #TA9836895 Report a problem
        1/20/2017Listed for rent$3,000$1/sqft
        Source: Long & Foster Real Estate, Inc. #TA9836895 Report a problem
        10/15/2016Price change$679,000-2.9%$192/sqft
        Source: Long & Foster Real Estate, Inc. #TA9789211 Report a problem
        9/12/2016Price change$699,000-5.5%$198/sqft
        Source: Long & Foster Real Estate, Inc. #TA9562370 Report a problem
        7/26/2016Price change$739,999-3.8%$210/sqft
        Source: Long & Foster Real Estate, Inc. #TA9562370 Report a problem
        6/10/2016Price change$769,000-2.5%$218/sqft
        Source: Long & Foster Real Estate, Inc. #TA9562370 Report a problem
        5/4/2016Price change$789,000-2.5%$224/sqft
        Source: Long & Foster Real Estate, Inc. #TA9562370 Report a problem
        3/31/2016Listed for sale$809,000+8.4%$229/sqft
        Source: Long & Foster Real Estate, Inc. #TA9562370 Report a problem
        8/18/2005Sold$746,000+29.7%$211/sqft
        Source: Public Record Report a problem
        11/26/2003Sold$575,000+51.7%$163/sqft
        Source: Public Record Report a problem
        9/7/2000Sold$379,000$107/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$9,815 +9.5%$780,100 +8.5%
        2024$8,961 +13.6%$719,200 +9.3%
        2023$7,890 +14.1%$658,300 +10.2%
        2022$6,912 +0.9%$597,400
        2021$6,847 $597,400
        2020$6,847 -11.6%$597,400 -11.6%
        2019$7,744 +8.2%$675,600 +5.3%
        2018$7,157 +9%$641,833 +5.6%
        2017$6,566 +18.8%$608,067 +5.9%
        2016$5,527 $574,300
        2015$5,527 -18.7%$574,300
        2014$6,802 $574,300 -15.8%
        2013-- $682,000 +0.4%
        2012-- $679,520 +0.4%
        2011-- $677,040 -14.7%
        2010-- $793,610 +3.4%
        2009-- $767,526 -2.1%
        2008-- $784,193 +37.8%
        2007-- $568,880 +11.7%
        2006-- $509,252 +13.3%
        2005-- $449,626 +15.3%
        2004-- $390,000 +19.4%
        2003-- $326,542 +24.1%
        2002-- $263,086 +31.8%
        2001-- $199,630
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        See how much you could borrow to make a competitive offer.
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        Climate risks

        Neighborhood: 21663

        Getting around

        64 / 100
        Somewhat Walkable
        66 / 100
        Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • District: Talbot County Public Schools

        Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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