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Under contract
  • $5,200,000

    21384 Coopertown Rd, Tilghman, MD 21671

    20beds
    14,035sqft
    : 
    Single Family Residence
    Built in 1920
    5 Acres Lot
    $-- Zestimate®
    $371/sqft
    $-- HOA

    What's special

    Set on five acresLush gardensExpansive outdoor dining terracesExpansive private docking
    *A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering – The Iconic Tilghman Island Inn* NOTE: Has public sewer and well. Welcome to a rare opportunity to own one of the most beautiful, fully reimagined waterfront hospitality properties on Maryland’s Eastern Shore. Set on five acres with sweeping views of the Chesapeake Bay, the Tilghman Island Inn is that extraordinary blend of romance, lifestyle, and investment that rarely becomes available. Established more than 50 years ago, the Inn has been transformed from top to bottom through a meticulous, comprehensive renovation. Today, it lives as a boutique luxury retreat with 20 uniquely designed guest rooms (five with gas fireplaces), a full-service waterfront restaurant and bar, expansive outdoor dining terraces, a sparkling 20' x 40' pool, lush gardens, and expansive private docking with the relaxed charm and quiet sophistication that define the Chesapeake Bay. Guests return year after year for the Inn’s serenity, sunset views, on-site dining, and proximity to St. Michaels, Easton, and Annapolis. For buyers, the value is just as clear: major improvements are already complete, systems are up to date, and recent guest ratings average about 95% across major travel platforms. Whether you envision this as a turnkey boutique hotel, a private family compound, a luxury event destination, or a future waterfront condominium development, the property is positioned for success. The Inn is legally configured as 20 residential condominium units offering flexibility. Property Features: 5-acre waterfront property, 15,000+ sq. ft. hotel and restaurant, 345 ft. vinyl seawall, 20 x 30 ft. T-Dock, 175 ft. floating dock with 7 additional boat slips, 20 uniquely designed guest rooms, 20 x 40 ft. in-ground pool, 30 x 12 ft. fully functional greenhouse, and Lush ornamental and raised bed vegetable gardens For investors seeking a premier turnkey hospitality venture or a high-value waterfront development opportunity, the Tilghman Island Inn presents a rare chance to own an Eastern Shore gem with limitless potential. **NOTE: FOR BROCHURE & VIDEO CONTACT AGENT**
    101 days
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    330
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    14
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    Zillow last checked: 7 hours ago

    Listing updated: March 03, 2026 at 10:03am

    Listed by:

    Angela Simonelli 410-200-0414,

    Compass (410) 429-7425,

    Co-Listing Agent: Stephen M Karbelk 571-481-1037,

    CENTURY 21 Commercial New Millennium

    Source: Bright MLS,MLS#: MDTA2012516MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 20
      • Bathrooms: 24
      • Full bathrooms: 21
      • 1/2 bathrooms: 3
      • Main level bathrooms: 14
      • Main level bedrooms: 10
      Basement
      • Area: 0
      Heating
      • Heat Pump, Natural Gas
      Cooling
      • Central Air, Ductless, Electric
      Appliances
      • Included: Water Heater
      Features
      • Has basement: No
      • Has fireplace: No
      Interior area
      • Total structure area: 14,035
      • Total interior livable area: 14,035 sqft
      • Finished area above ground: 14,035
      • Finished area below ground: 0

      Property

      Parking
      • Parking features: Parking Lot
      Accessibility
      • Accessibility features: 2+ Access Exits
      Features
      • Levels: Two
      • Stories: 2
      • Has private pool: Yes
      • Pool features: Private
      • Has view: Yes
      • View description: Panoramic, Water
      • Has water view: Yes
      • Water view: Water
      Lot
      • Size: 5 Acres
      Details
      • Additional structures: Above Grade, Below Grade
      • Parcel number: MULTIPLE TAX RECORDS
      • Zoning: COMMERCIAL/RESIDENTIAL
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Other
      • Property subtype: Single Family Residence
      Materials
      • Frame
      Condition
      • New construction: No
      • Year built: 1920
      • Major remodel year: 2020

      Utilities & green energy

      • Sewer: Grinder Pump
      • Water: Well

      Community & HOA

      Community
      • Subdivision: None Available
      HOA
      • Has HOA: No
      Location
      • Region: Tilghman

      Financial & listing details

      • Price per square foot: $371/sqft
      • Date on market: 12/18/2025
      • Listing agreement: Exclusive Right To Sell
      • Ownership: Fee Simple
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        $1,828/mo

        Price history

        Price history
        DateEventPrice
        3/3/2026Contingent$5,200,000$371/sqft
        Source: Bright MLS #MDTA2012516 Report a problem
        12/18/2025Listed for sale$5,200,000$371/sqft
        Source: Bright MLS #MDTA2012516 Report a problem

        Public tax history

        Public tax history
        Tax history is unavailable.

        BuyAbility℠ payment

        Est. payment
        $29,168/mo
        Principal & interest
        $26308
        Property taxes
        $2860
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          Climate risks

          Neighborhood: 21671

          Getting around

          17 / 100
          Car-Dependent
          35 / 100
          Somewhat 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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