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21384 Coopertown Rd, 
Tilghman, MD 21671

$5,200,000


20

Beds


24

Baths


14,035

Sq Ft


Single Family

Active

Listed by

Angela Pellerano Simonelli

Compass

Last updated:

December 19, 2025, 01:08 PM

MLS#

MDTA2012516

Source:

BRIGHTMLS

About This Home

21384 Coopertown Rd

*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**

Home Facts

Single Family

24 Baths

20 Bedrooms

Built in 1920

Price Summary

5,200,000

$370 per Sq. Ft.

MLS #:

MDTA2012516

Last Updated:

December 19, 2025, 01:08 PM

Added:

1 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

20

Bathrooms

Total Bathrooms:

24

Full Bathrooms:

21

Interior

Living Area:

14,035 Sq. Ft.


Structure

Structure

Building Area:

14,035 Sq. Ft.

Year Built:

1920


Lot

Lot Size (Sq. Ft):

217,800


Finances & Disclosures

Finances

Price:

$5,200,000

Price per Sq. Ft:

$370 per Sq. Ft.

Source:BRIGHTMLS
The information being provided by Bright Mls 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. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2025 Bright Mls All rights reserved.

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