*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**
Under contract
$5,200,000
21384 Coopertown Rd, Tilghman, MD 21671
20beds
14,035sqft
Est.:
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
- 101 days |
- 330 |
- 14 |
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#: MDTA2012516
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
Estimated market value
Not available
Estimated sales range
Not available
$1,828/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 3/3/2026 | Contingent | $5,200,000$371/sqft |
Source: | ||
| 12/18/2025 | Listed for sale | $5,200,000$371/sqft |
Source: | ||
Public tax history
Public tax history
Tax history is unavailable.BuyAbility℠ payment
Est. payment
$29,168/mo
Principal & interest
$26308
Property taxes
$2860
More affordability tools
Climate risks
Neighborhood: 21671
Nearby schools
GreatSchools rating
- 4/10Tilghman Elementary SchoolGrades: PK-5Distance: 0.5 mi
- 5/10St. Michaels Middle/High SchoolGrades: 6-12Distance: 7.6 mi
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.
Local experts in 21671
- Maryland
- Talbot County
- Tilghman
- 21671
- 21384 Coopertown Rd
