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Off market
  • $942,500

    111 E Chestnut St, Saint Michaels, MD 21663

    4beds
    1,852sqft
    Single Family Residence
    Built in ----
    -- sqft lot
    $942,500 Zestimate®
    $509/sqft
    $2,703 Estimated rent

    Home value

    $942,500

    $839,000 - $1.06M

    $2,703/mo

    Zestimate® history
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    What's special

    Charming historic homeBbq grillPrivate fenced courtyardStainless steel appliancesPropane rangeAmple cabinetsFire pit

    Historic Home for Long-Term Lease in Vibrant St. Michaels - 111 E. Chestnut St, St. Michaels, MD 21663 Discover a charming, historic home on the corner of East Chestnut Street and St. Mary's Square, perfect for a single person, young couple, or family seeking a year-round retreat in St. Michaels. Carefully preserved and updated, this residence blends timeless character with practical comforts, offering a serene base in the heart of a lively waterfront town. This house is an ideal home for you: Walkable Lifestyle: Steps from St. Michaels Harbor, world-class restaurants, boutique shops, and cultural treasures like the Chesapeake Bay Maritime Museum and St. Michaels Museum (across the street). Enjoy quiet privacy despite the central location. Outdoor Adventures: Enjoy sailing summer camps, yacht racing, or log canoe racing at the Chesapeake Bay Maritime Museum, Miles River Yacht Club, or Tred Avon Yacht Club. Bike or jog the St. Michaels Nature Trail, or tee off at premier golf courses like Links at Perry Cabin (a Pete Dye design), Hog Neck Golf Course, or Blue Heron Golf Course. Community Gems: Unwind at Muskrat Park's harbor gazebo (0.5 acres), explore Hollis Park's pirate ship playground (1.9 acres), or reflect at Frederick Douglass Park's historic kiosk (0.1 acres). Clint S. Bradley Park (2 acres) offers play structures, while Canton Farm Nature Preserve (40 acres) beckons nature lovers. Work & Play: High-speed Wi-Fi and cable make remote work seamless ideal for museum staff, freelancers, or nearby employers. Celebrate your special events at the five-star Inn at Perry Cabin or nearby four-star hotels and restaurants with your friends and family. Seasonal Delights: St. Michaels offers year-round activities. Summer buzzes with sailing and festivals; winter events are full of joy and happiness. Or just wrap yourself in cozy charm with tree-lined streets glowing under old-fashioned lamp posts, visible from every upstairs bedroom. Home Features: Rare Private Garage: A St. Michaels rarity, with pantry access for easy grocery unloading. Inviting Kitchen: Granite countertops of the highest grade, stainless steel appliances, propane range, and ample cabinets for cozy meals. Private Fenced Courtyard: Relax by the BBQ grill or fire pit, or grow a small garden a tranquil haven. Flexible Layout: Four bedrooms, including a first-floor master suite tied to the family room. Three upstairs rooms, each framing the picturesque street, double as offices or a gym. Lease Details: Perfect for year-round living in a high-demand area. Dog-friendly! St. Michaels welcomes pups with water bowls at shops, restaurants, and ample dog-walking paths along parks, trails, brick sidewalks, and quiet streets. This home is your gateway to St. Michaels' tight-knit community, rich history, and endless activities from sailing to golfing to savoring local flavors. Whether you're working remotely or raising a family, settle into a space where every season shines. Contact Us to Secure Your Lease Today! Tenant pays utilities: electricity, water, sewer, propane, and optional cable. Tenant takes care of the landscaping of the front, side, and courtyard. We suggest that you obtain renters insurance.

    This property is off market, which means it's not currently listed for sale or rent on Zillow. This may be different from what's available on other websites or public sources.

    Zillow last checked:

    Listing updated:

    Source: Zillow Rentals

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 3
    • Full bathrooms: 2
    • 1/2 bathrooms: 1
    Heating
    • Baseboard, Forced Air, Heat Pump, Wall Furnace
    Cooling
    • Central Air
    Appliances
    • Included: Dishwasher, Dryer, Microwave, Oven, Refrigerator, Washer
    • Laundry: In Unit
    Features
    • Flooring: Hardwood, Tile
    Interior area
    • Total interior livable area: 1,852 sqft

    Property

    Parking
    • Parking features: Attached, Garage, Off Street
    • Has attached garage: Yes
    • Details: Contact manager
    Features
    • Exterior features: Bicycle storage, Cable not included in rent, Electricity not included in rent, Heating system: Baseboard, Heating system: Forced Air, Heating system: Wall, Pets welcome., Sewage not included in rent, Water not included in rent
    Details
    • Parcel number: 02063018

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence

    Community & neighborhood

    Location
    • Region: Saint Michaels

    HOA & financial

    Other fees
    • Deposit fee: $3,990

    Other

    Other facts
    • Available date: 05/15/2026

    Price history

    DateEventPrice
    4/12/2026Listing removed$3,990$2/sqft
    Source: Zillow Rentals Report a problem
    3/22/2026Listed for rent$3,990+33.4%$2/sqft
    Source: Zillow Rentals Report a problem
    10/15/2025Listing removed$2,990$2/sqft
    Source: Zillow Rentals Report a problem
    9/3/2025Price change$2,990-14.3%$2/sqft
    Source: Zillow Rentals Report a problem
    8/4/2025Price change$3,490-10.5%$2/sqft
    Source: Zillow Rentals Report a problem
    6/23/2025Price change$3,900-13.1%$2/sqft
    Source: Zillow Rentals Report a problem
    4/15/2025Listed for rent$4,490+13.7%$2/sqft
    Source: Zillow Rentals Report a problem
    10/14/2024Listing removed$3,950$2/sqft
    Source: Zillow Rentals Report a problem
    7/29/2024Listing removed--
    Source: Zillow Rentals Report a problem
    7/4/2024Price change$3,950-12.2%$2/sqft
    Source: Zillow Rentals Report a problem
    5/8/2024Price change$4,500-6.3%$2/sqft
    Source: Zillow Rentals Report a problem
    5/2/2024Listed for rent$4,800$3/sqft
    Source: Zillow Rentals Report a problem
    4/17/2024Listing removed--
    Source: Zillow Rentals Report a problem
    3/22/2024Listed for rent$4,800-3%$3/sqft
    Source: Zillow Rentals Report a problem
    6/5/2022Listing removed--
    Source: Zillow Rental Manager Report a problem
    5/5/2022Listed for rent$4,950+76.8%$3/sqft
    Source: Zillow Rental Manager Report a problem
    8/17/2020Listing removed$549,900$297/sqft
    Source: Chesapeake Bay Real Estate Plus, LLC #MDTA138624 Report a problem
    7/8/2020Price change$549,900-6.6%$297/sqft
    Source: Chesapeake Bay Real Estate Plus, LLC #MDTA138624 Report a problem
    7/8/2020Listing removed$2,800$2/sqft
    Source: Owner Report a problem
    6/30/2020Listed for rent$2,800+27.3%$2/sqft
    Source: Owner Report a problem
    6/9/2020Listed for sale$589,000+10.1%$318/sqft
    Source: Chesapeake Bay Real Estate Plus, LLC #MDTA138346 Report a problem
    6/28/2019Listing removed$2,200$1/sqft
    Source: Chesapeake Bay Real Estate Plus, LLC #MDTA135350 Report a problem
    6/20/2019Listed for rent$2,200$1/sqft
    Source: Chesapeake Bay Real Estate Plus, LLC #MDTA135350 Report a problem
    6/20/2019Listing removed$535,000+52.9%$289/sqft
    Source: Chesapeake Bay Real Estate Plus, LLC #MDTA133046 Report a problem
    8/13/2009Sold$350,000$189/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025-- $499,100 +3.1%
    2024$6,034 +7.2%$484,267 +3.2%
    2023$5,626 +7%$469,433 +3.3%
    2022$5,260 +0.9%$454,600
    2021$5,211 $454,600
    2020$5,211 -2.5%$454,600 -2.5%
    2019$5,346 +5.5%$466,400 +2.6%
    2018$5,067 +6.1%$454,433 +2.7%
    2017$4,778 +15.3%$442,467 +2.8%
    2016$4,143 $430,500
    2015$4,143 -7.6%$430,500
    2014$4,485 $430,500 -3.3%
    2013-- $445,000
    2012-- $445,000
    2011-- $445,000 -28.5%
    2010-- $622,780 +11.7%
    2009-- $557,542 +13.3%
    2008-- $492,306 +15.3%
    2007-- $427,070 +11.7%
    2006-- $382,402 +13.2%
    2005-- $337,736 +15.2%
    2004-- $293,070 +11%
    2003-- $264,096 +12.3%
    2002-- $235,123 +14.1%
    2001-- $206,150

    Find assessor info on the county website

    Neighborhood: 21663

    Nearby schools

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    Estimated market value
    $942,500
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    Estimated market value
    $942,500