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Pending
  • $1,900,000

    3750 Windy Hill Rd, Trappe, MD 21673

    3beds
    2baths
    1,966sqft
    : 
    $11,670/mo
    Get pre-qualified
    Other
    Built in ----
    -- sqft lot
    $-- Zestimate®
    $966/sqft
    $-- HOA

    What's special

    This exceptional farm in Talbot County, Maryland, presents a rare opportunity to own a highly productive Eastern Shore property that combines agricultural value, quality improvements, and premier recreational appeal. Situated in a region known for its fertile soils and strong farming history, this 90A± acre home farm offers a balanced mix of tillable acreage, improved structures, and wildlife habitat, making it well-suited for farming operations, outdoor recreation, and long-term land investment. The property has a proven track record of row crop production, including corn, soybeans, and wheat. A diverse and productive soil profile supports continued agricultural use, with primary soils consisting of Mattapex silt loam and Nassawango silt loam across the majority of the fields. Additional areas include Mattapex-Woodstown soils located within previously enrolled CRP sections and wooded portions of the farm. These soils are well regarded across the Eastern Shore for their consistency and productivity, providing a solid foundation for both commercial farming and conservation practices. The farm is zoned agricultural, allowing flexibility for a variety of uses, including crop production, recreational enjoyment, and potential enrollment in conservation programs. A large portion of the acreage is tillable, offering income potential or lease opportunities, while the remaining mix of timber and habitat enhances the property's recreational value. At the center of the property sits a well-maintained 1,966 square foot brick ranch-style home built in 1997. The residence offers three bedrooms and two full bathrooms and has been thoughtfully designed for both comfort and functionality. The main living area features a spacious living room with a knotty pine accent wall and bowed window that brings in natural light. The dining room includes chair rail detailing, tongue-and-groove paneling, and a built-in glass-front cabinet, creating a functional and inviting setting. The kitchen is well-appointed with wood cabinetry extending to the ceiling, crown molding, stainless steel appliances, and a center island with seating. A pass-through connects the kitchen to the dining area, improving flow for daily use and gatherings. French doors lead to a sunroom that overlooks the surrounding farmland and wooded edges, providing a consistent view of the property throughout the seasons. The primary suite includes a private bathroom with a deep jetted soaking tub. Additional features of the home include a covered front porch and an attached two-car garage. Supporting the agricultural operation are several outbuildings, including a milk house and two additional structures, highlighted by a custom-built steel building. These improvements provide space for equipment storage, workshop use, and potential game processing. From a recreational standpoint, this Talbot County farm offers strong hunting opportunities. A large pond, complete with a strategically placed hunting pit, is heavily utilized by migratory Canada geese during the season. The combination of open ground, water, and surrounding timber creates an ideal setup for waterfowl hunting. The property also supports a healthy population of whitetail deer, adding to its appeal for hunting and outdoor recreation. For buyers seeking additional acreage, an adjoining 82.54A± acre tract is also available. This parcel includes a large portion of tillable ground, with sections previously enrolled in CRP. The additional tract provides an opportunity to expand the farming operation, increase recreational use, or secure additional investment acreage. It may be purchased together with the home farm or separately, offering flexibility for a range of buyers. It's location on Maryland's Eastern Shore places it within a well-established agricultural region while still providing access to nearby towns, waterways, and outdoor amenities.
    131 days
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    67
    |
    3
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    Zillow last checked:

    Listed by:

    Casey Kennedy,

    Whitetail Properties 217-285-9000

    Source: Whitetail Properties,MLS#: 108977

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      Features
      • Has basement: No
      • Has fireplace: No
      Interior area
      • Total structure area: 1,966
      • Total interior livable area: 1,966 sqft

      Property

      Details
      • Parcel number: 03159124

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Other

      Community & HOA

      Location
      • Region: Trappe

      Financial & listing details

      • Price per square foot: $966/sqft
      • Tax assessed value: $591,467
      • Annual tax amount: $5,413
      • Date on market: 4/17/2026
      • Lease term: Contact For Details

        Estimated market value

        Not available

        Estimated sales range

        Not available

        $2,283/mo

        Price history

        DateEventPrice
        8/20/2026Sold$1,600,000-23.8%$814/sqft
        Source: Bright MLS #MDTA2013664 Report a problem
        5/20/2026Sold$2,100,000+68%$1,068/sqft
        Source: Bright MLS #MDTA2013860 Report a problem
        5/6/2026Pending sale$1,250,000-34.2%$636/sqft
        Source: Whitetail Properties #109410 Report a problem
        4/17/2026Price change$1,900,000+52%$966/sqft
        Source: Whitetail Properties #108977 Report a problem
        4/17/2026Price change$1,250,000-85.1%$636/sqft
        Source: Whitetail Properties #109410 Report a problem
        2/12/2026Listed for sale$8,400,000+5183%$4,273/sqft
        Source: Bright MLS #MDTA2012586 Report a problem
        1/11/2006Sold$159,000$81/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$5,413 +7.8%$591,467 +6.3%
        2024$5,023 +12.7%$556,233 +6.8%
        2023$4,457 +9.5%$521,000
        2022$4,068 +7.8%$521,000 +3.4%
        2021$3,774 +1.7%$503,733 +1.7%
        2020$3,709 +0.5%$495,100
        2019$3,690 +4.9%$495,100 +1.1%
        2018$3,518 +5.7%$489,900 +0.5%
        2017$3,327 +11.8%$487,300 +0.7%
        2016$2,975 $484,067 +0.7%
        2015$2,975 +12.3%$480,833 +0.7%
        2014$2,649 $477,600
        2013-- $477,600
        2012-- $477,600 -7.3%
        2011-- $515,300 0%
        2010-- $515,330
        2009-- $515,330 -1.3%
        2008-- $522,120 +5.7%
        2007-- $493,762
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        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: 21673

        Getting around

        0 / 100
        Car-Dependent
        25 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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