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For sale
  • $718,000

    21939 Sherwood Landing Rd, Sherwood, MD 21665

    3beds
    1,696sqft
    : 
    $4,593/mo
    Get pre-qualified
    Single Family Residence
    Built in 1905
    0.29 Acres Lot
    $619,100 Zestimate®
    $423/sqft
    $-- HOA

    What's special

    Fenced rear yardBeautifully landscaped backyard oasisAntiqued farmhouse staircaseHardwood floorsLovely screened porchCozy family roomGranite counters
    OPEN HOUSE CANCELED. Homes like these rarely come along in Talbot County: a totally updated cottage with a beautiful in-ground saltwater swimming pool and every update imaginable – all less than 300 feet from the Sherwood Landing pier, where you might launch your kayak, take a morning swim, or even dock your boat for the season. You’ll enjoy greeting neighbors on sunny mornings and cool afternoon naps on the lovely screened porch. Just inside, you’ll find a beautiful living room with so many original early 1900’s details, including an antiqued farmhouse staircase, hardwood floors, and a beautiful mantle and fireplace (propane-fired but easily converted back to wood). There is also a cozy family room that can easily be used as a first-floor bedroom, a powder room, a laundry closet, and a gorgeous kitchen fully remodeled in 2019. The kitchen features a large center island hub, granite counters, new cabinetry, and replaced appliances, including a gas cooking range, plus an enlarged Pella bay window above the sink that offers sunny views of the backyard and pool. Just off the kitchen is a dining area with banquette seating and a neat wet bar, easily accessed through replaced Pella sliders to the expansive rear deck. This home is built for entertaining! Upstairs, you will be pleased to find 3 nicely proportioned bedrooms, all with hardwood flooring and two of which have views over Harris Creek’s Waterhole Cove. A full bath features more original detailing along with a jetted bathtub. A small basement with an encapsulated crawl space houses many of the home’s systems, including the water heater, a sump pump, and a zoned hybrid fuel heat pump (2023) with oil-fired backup. A second heat pump (2010) in the attic services the top floor. While the interior of this home offers so much charm and character, along with every thoughtful amenity possible, the real star of the show is the fenced rear yard. The sellers have invested years of sweat equity into creating a beautifully landscaped backyard oasis complete with a kidney-shaped saltwater concrete pool with travertine decking. The gardens burst all season with hydrangea, verbena, hibiscus, crepe myrtle, and many native perennials. The large deck offers multiple dining and entertaining areas for summer cookouts and crab feasts. Bonus! A single bay garage provides ample storage for all your bikes, boats, tools, and yard and pool equipment. A full list of updates and upgrades is available, including but not limited to: 50 year architectural shingle roof (2025), front porch (2025), heat pump (2023), blown in hardpack insulation (2018), chimney liners and flue (2021), whole house water treatment system (2021), oil tank (2021), kitchen (2019) and over $35,000 of landscaping and hardscaping. The list goes on and on. Life in Talbot County's quaint Village of Sherwood doesn't get much better than this. You’ll be nestled solidly on the banks of Waterhole Cove on the Harris Creek and in the heart of this small community of approximately 20 turn-of-the-Century homes. An 8-minute drive from Saint Michaels, Sherwood is known for its friendly, caring neighbors, beautiful sunrises, community pier enjoyed by residents, and a wonderful 4th of July celebration.
    11 hours
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    Zillow last checked:

    Listing updated:

    Listed by:

    James M. Baldwin 443-255-2502,

    Compass (410) 886-7342,

    Listing Team: The Baldwin & Griffin Group Of Compass, Co-Listing Team: The Baldwin & Griffin Group Of Compass,Co-Listing Agent: Andrea G Griffin 410-591-9183,

    Compass

    Source: Bright MLS,MLS#: MDTA2014838MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 1
      • 1/2 bathrooms: 1
      • Main level bathrooms: 1
      Rooms
      • Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Basement, Primary Bathroom, Half Bath
      Primary bedroom
      • Features: Flooring - HardWood
      • Level: Upper
      Bedroom 2
      • Features: Flooring - HardWood
      • Level: Upper
      Bedroom 3
      • Features: Flooring - HardWood
      • Level: Upper
      Primary bathroom
      • Features: Bathroom - Jetted Tub
      • Level: Upper
      Basement
      • Features: Basement - Unfinished
      • Level: Lower
      Dining room
      • Features: Breakfast Room, Wet Bar, Window Treatments
      • Level: Main
      Family room
      • Features: Flooring - HardWood, Fireplace - Gas, Fireplace - Wood Burning
      • Level: Main
      Half bath
      • Level: Main
      Kitchen
      • Features: Flooring - HardWood, Granite Counters, Dining Area, Kitchen Island, Lighting - Ceiling, Kitchen - Propane Cooking
      • Level: Main
      Living room
      • Features: Flooring - HardWood
      • Level: Main
      Screened porch
      • Level: Main
      Heating
      • Central, Forced Air, Heat Pump, Programmable Thermostat, Radiator, Zoned, Electric, Oil
      Cooling
      • Central Air, Electric
      Appliances
      • Included: Electric Water Heater
      Features
      • Floor Plan - Traditional, Kitchen Island, Family Room Off Kitchen, Beamed Ceilings, Dry Wall, Plaster Walls
      • Flooring: Ceramic Tile, Hardwood
      • Basement: Drainage System,Exterior Entry,Concrete,Sump Pump,Unfinished
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 1,696
      • Total interior livable area: 1,696 sqft
      • Finished area above ground: 1,696
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 4
      • Parking features: Storage, Garage Faces Front, Inside Entrance, Parking Space Conveys, Private, Shared Driveway, Driveway, Detached, Off Street
      • Garage spaces: 1
      • Has uncovered spaces: Yes
      Accessibility
      • Accessibility features: None
      Features
      • Levels: Three
      • Stories: 3
      • Patio & porch: Deck, Porch, Screened, Screened Porch
      • Exterior features: Outdoor Shower, Storage
      • Has private pool: Yes
      • Pool features: In Ground, Private
      • Fencing: Full
      • Has view: Yes
      • View description: Water, Bay
      • Has water view: Yes
      • Water view: Water,Bay
      • Waterfront features: Bayblock, Canoe/Kayak, Fishing Allowed, Public Access, Swimming Allowed, Bay
      • Body of water: Harris Creek
      Lot
      • Size: 0.29 Acres
      • Features: Backs to Trees, Front Yard, Landscaped, Level, No Thru Street, Open Lot, Rear Yard, Rural, Poolside
      Details
      • Additional structures: Above Grade, Below Grade
      • Parcel number: 2105188067
      • Zoning: RESIDENTIAL
      • Zoning description: Rural residential -Talbot County Village
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Coastal,Cottage
      • Property subtype: Single Family Residence
      Materials
      • Wood Siding, Blown-In Insulation
      • Foundation: Crawl Space, Brick/Mortar
      • Roof: Architectural Shingle
      Condition
      • Excellent
      • New construction: No
      • Year built: 1905

      Utilities & green energy

      • Sewer: Septic Exists
      • Water: Public

      Community & HOA

      Community
      • Subdivision: Sherwood
      HOA
      • Has HOA: No
      Location
      • Region: Sherwood

      Financial & listing details

      • Price per square foot: $423/sqft
      • Tax assessed value: $316,667
      • Annual tax amount: $2,827
      • Date on market: 8/28/2026
      • Listing agreement: Exclusive Right To Sell
      • Inclusions: Parking Included In Listprice, parking Included In Saleprice
      • Ownership: Fee Simple

        Estimated market value

        $619,100

        $557,000 - $687,000

        $1,674/mo

        Price history

        DateEventPrice
        8/28/2026Listed for sale$718,000+52.8%$423/sqft
        Source: Bright MLS #MDTA2014838 Report a problem
        9/8/2009Sold$470,000-14.4%$277/sqft
        Source: Public Record Report a problem
        5/2/2009Price change$549,000-7.7%$324/sqft
        Source: Lacaze Meredith Real Estate #TA6788157 Report a problem
        7/21/2008Price change$595,000-7.8%$351/sqft
        Source: Lacaze Meredith Real Estate #TA6788157 Report a problem
        6/18/2008Listed for sale$645,000+145.7%$380/sqft
        Source: Lacaze Meredith Real Estate #TA6788157 Report a problem
        9/30/2005Sold$262,500$155/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$2,540 -4.5%$308,900 +4.9%
        2024$2,659 +11%$294,500 +5.1%
        2023$2,396 +13.6%$280,100 +5.4%
        2022$2,110 +6%$265,700
        2021$1,991 $265,700
        2020$1,991 -4.9%$265,700 -4.9%
        2019$2,093 +4.3%$279,300
        2018$2,006 +5.2%$279,300
        2017$1,907 -11.6%$279,300 -14.4%
        2016$2,157 $326,300
        2015$2,157 +8.6%$326,300
        2014$1,987 $326,300 -15.3%
        2013-- $385,100 +4.5%
        2012-- $368,687 +4.7%
        2011-- $352,273 +4.9%
        2010-- $335,860 +12%
        2009-- $299,866 +13.6%
        2008-- $263,873 +15.8%
        2007-- $227,880 +14.9%
        2006-- $198,362 +17.5%
        2005-- $168,846 +21.2%
        2004-- $139,330 +11.7%
        2003-- $124,752 +13.2%
        2002-- $110,176 +15.2%
        2001-- $95,600
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        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.
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        Climate risks

        Neighborhood: 21665

        Getting around

        0 / 100
        Car-Dependent
        25 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Tilghman
        • Middle: St. Michaels
        • High: St. Michaels
        • 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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