21384 Coopertown Rd
$5,200,000
Price
20
Beds
24
Baths
14,035 Sq. Ft.
$371 / Sq. Ft.
14,035
Sq. Ft.
$371
per Sq. Ft.
Listed By Compass
Listed By Compass
Description
*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...*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**
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...*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**
Listing Agent
![Angela Simonelli]()
angela.simonelli@compass.comP: (410)-200-0414
Property Details for 21384 Coopertown Road
Tax ID Number
MULTIPLE TAX RECORDS
OwnershipFee Simple
Condo Coop AssociationNo
HOANo
Structure TypeOther
StyleOther
Levels/Stories2
WaterfrontNo
LISTING UPDATED: 12/19/2025 10:40 AM
Property Details for 21384 Coopertown Road
| Status | Active |
|---|---|
| MLS # | MDTA2012516 |
| Days on Market | 7 |
| Taxes | - |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Compass Type | Single Family |
| MLS Type | Residential / Fee Simple |
| Year Built | 1920 |
| Lot Size | 5.00 AC / 217,800 SF |
| County | Talbot County |
Location
Add your commute
Building Information for 21384 Coopertown Road
Stories2Year Built1920Building Size-Lot Size5.00 AC / 217,800 SF
Payment Calculator
$25,695 per month
30 year fixed, 6.28% Interest
Principal and Interest
$25,695
Property Taxes
$0
HOA Dues
$0
The Payment Calculator is for illustrative purposes only.
Property Information for 21384 Coopertown Road
Location
Location
- In City Limits: No
- School District Name: TALBOT COUNTY PUBLIC SCHOOLS
- School District County ID: 121138072466
- SchoolDistrictSource: Listing Agent
- County: TALBOT
Waterfront / Water Access
Waterfront / Water Access
- Water View: Yes
- Water Access: No
- Water Oriented: No
- Navigable Water: No
- Tidal Water: No
- Riparian Rights Y/N: No
Association / Community Info
Association / Community Info
- Senior Community: No
Taxes and Assessment
Taxes and Assessment
- Tax Year: 2025
- Tax Assessed Value: $0
- Year Assessed: 2025
- County Tax: $0
- Improvement Assessed Value: $0
- Land Assessed Value: $0
- Clean Green Assessed: No
- Land Use Code: C
- Zoning: COMMERCIAL/RESIDENTIAL
- School Tax: $0
- Automatically Update Tax Values Y/N: Yes
Rooms
Main
- # Bedrooms Count Main Level: 10
- # Bathrooms Count Main Level: 14
- # Bathrooms Full Main Level: 11
- # Bathrooms Half Main Level: 3
All Upper Levels
- # Bedrooms Count All Upper Levels: 10
- # Bathrooms Count All Upper Levels: 10
- # Bathrooms Full All Upper Levels: 10
Upper Level 1
- # Bedrooms Count Upper Level: 10
- # Bathrooms Count Upper Level: 10
- # Bathrooms Full Upper Level: 10
Rooms
- Stories: Main, Upper 1
Building Info
Building Info
- Year Major Reno Remodel: 2020
- Total Finished SQFT: 14,035.00
- Total Finished SQFT Source: Assessor
- Tax Total Finished SQFT: 14,035.00
- Total SQFT: 14,035.00
- Total SQFT Source: Assessor
- Construction Materials: Frame
- Room and Floor: Bedrooms-Main Level-1, Bedrooms-Main Level-2, Bedrooms-Main Level-3, Bedrooms-Main Level-4, Bedrooms-Main Level-5, Bedrooms-Main Level-6, Bedrooms-Main Level-7, Bedrooms-Main Level-8, Bedrooms-Main Level-9, Bedrooms-Main Level-10, Bathrooms Full-Main Level-1, Bathrooms Full-Main Level-2, Bathrooms Full-Main Level-3, Bathrooms Full-Main Level-4, Bathrooms Full-Main Level-5, Bathrooms Full-Main Level-6, Bathrooms Full-Main Level-7, Bathrooms Full-Main Level-8, Bathrooms Full-Main Level-9, Bathrooms Full-Main Level-10, Bathrooms Full-Main Level-11, Bathrooms Half-Main Level-1, Bathrooms Half-Main Level-2, Bathrooms Half-Main Level-3, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bedrooms-Upper Level 1-4, Bedrooms-Upper Level 1-5, Bedrooms-Upper Level 1-6, Bedrooms-Upper Level 1-7, Bedrooms-Upper Level 1-8, Bedrooms-Upper Level 1-9, Bedrooms-Upper Level 1-10, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2, Bathrooms Full-Upper Level 1-3, Bathrooms Full-Upper Level 1-4, Bathrooms Full-Upper Level 1-5, Bathrooms Full-Upper Level 1-6, Bathrooms Full-Upper Level 1-7, Bathrooms Full-Upper Level 1-8, Bathrooms Full-Upper Level 1-9, Bathrooms Full-Upper Level 1-10
- # Bathrooms Full: 21
- # Bathrooms Half: 3
- Other Structure: Above Grade, Below Grade
Lot / Land Information
Lot / Land Information
- Lot Size Source: Estimated
- Parcel ID: 9526254
Parking
Parking
- Type Of Parking: Parking Lot
Interior Features
Interior Features
- Fireplace: No
- Accessibility Features: 2+ Access Exits
Exterior Features
Exterior Features
- Pool: Yes - Personal
Utilities
Utilities
- Heating: Yes
- Cooling Type: Central A/C, Ductless/Mini-Split
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Natural Gas
- Hot Water: Multi-tank
- Water Source: Well
- Sewer Septic: Grinder Pump
Confidential Data
Listing Office
- List Agent AOR: Mid-Shore Board of REALTORS
- List Agent URL: AngelaSimonelli.com
Property History for 21384 Coopertown Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Dec 18, 2025 | Listed (Active) BRIGHT #MDTA2012516 | $5,200,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 12/18/2025 | Listed (Active) BRIGHT #MDTA2012516 | $5,200,000 |
For completeness, Compass often displays two records for one sale: the MLS record and the public record.
Public Records for 21384 Coopertown Road
Taxable ValueLand-Additions-Total-
Home Facts
Total Finished SqFt14,035 SqFtAbove Grade Finished SqFt14,035 SqFtStories2StyleHotel / MotelYear Built1920CountyTALBOTAPN05-198795
Schools near 21384 Coopertown Road
This home is within Talbot County Public Schools.
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 5 | |||
| Public - | 6 to 12 | |||
| Public - | 9 to 12 |
Rating | School | Distance |
|---|---|---|
Tilghman Elementary School PublicPK to 5 | ||
St. Michaels Middle/High School Public6 to 12 | ||
Easton High School Public9 to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.
© 2025 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 12/19/2025 10:40 AM