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21384 COOPERTOWN Road
TILGHMAN MD 21671 US

$5,200,000

Active Listing ID MDTA2012440
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Lot: 5.00 Acres
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$5,200,000

Active Listing ID MDTA2012440
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21384 COOPERTOWN Road *A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering - The Iconic Tilghman Island Inn* 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**

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Property Features

  • Facts
  • Lot Size: 5.00 Acres
  • Property Type: Other
  • Property Sub-type: Other
  • Features
  • Cooling System: Ductless, Central Air
  • Heating Fuels: Heat Pump (Heating)

Property

  • propertytype: Other
  • propertysubtype: Other
  • listprice: 5200000
  • unparsedaddress: 21384 COOPERTOWN Road
  • postalcity: TILGHMAN
  • stateorprovince: MD
  • country: US
  • postalcode: 21671
  • bathroomsfull: 0
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 5
  • lotsizeunits: Acres
  • lotsizearea: 5
  • livingarea: 0
  • livingareaunits: Square Feet
  • latitude: 38.71998
  • longitude: -76.33721
  • listagentfullname: Angela Pellerano Simonelli
  • listagentemail: angela.simonelli@compass.com
  • listagentkey: 3yd-TRENDPA-3317220
  • listagentmlsid: 3317220
  • listagentpreferredphone: 4102000414
  • listagentofficephone: 4107458060
  • listofficekey: 3yd-TRENDPA-COMPS15
  • listagentstatelicense: 5004882
  • listofficemlsid: COMPS15
  • disclaimer: Copyright © 2025 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: TRENDPA
  • yearbuilt: 1920
  • listingcontractdate: 2025-12-18
  • countyorparish: TALBOT
  • elementaryschooldistrict: TALBOT COUNTY PUBLIC SCHOOLS
  • middleorjuniorschooldistrict: TALBOT COUNTY PUBLIC SCHOOLS
  • highschooldistrict: TALBOT COUNTY PUBLIC SCHOOLS
  • cooling: Ductless, Central Air
  • constructionmaterials: Frame
  • heating: Heat Pump (Heating)
  • numberofunitstotal: 1
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 47
  • parkingfeatures: Parking Lot
  • waterfrontyn: False
  • franchiseaffiliation: None
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -76.33721, 38.71998
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Compass", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"angela.simonelli@compass.com", "ListBrokerageCity":"WASHINGTON", "ListBrokerageCountry":"US", "ListBrokerageEmail":"holly@compass.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"Compass", "ListBrokeragePhone":"(202) 491-1275", "ListBrokeragePostalCode":"20005", "ListBrokerageStateOrProvince":null, "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"1313 14th St NW", "ListBrokerageWebsiteUrl":null, "ListOfficeAddress1":"2077 Somerville Road unit: 200 ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"COMPS15", "ListOfficeCity":"Annapolis", "ListOfficeCountry":"USA", "ListOfficeEmail":"holly@compass.com", "ListOfficePostalCode":"21401", "ListOfficeStateOrProvince":"MD", "ListPriceCurrencyType":"USD", "ListingTitle":"Commercial Sale - TILGHMAN, MD", "ListingURL":null, "MLSModificationTimestamp":"2025-12-18 20:17:54", "Neighborhoods":[], "PostalCode":null, "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":0, "TaxDescription":null, "TaxYear":null}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 12/18/2025 10:11:57 PM GMT
Source Updated Date: 12/19/2025 12:52:45 PM GMT

Courtesy of: Angela Pellerano Simonelli, Compass, angela.simonelli@compass.com

Copyright © 2025 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.