* 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 * *
Single-familyProperty Type
1920Year Built
5 acresLot Size
$278Price/Sq.Ft.
Listed by Angela Simonelli• Compass
•410-429-7425 (broker)
Listed by Stephen Karbelk• CENTURY 21 Commercial New Millennium
•703-753-7910 (broker)
•wendy.dean@c21nm.com (broker)
Bought with Cornelia C Heckenbach• Long & Foster Real Estate, Inc.
Est. $2,915 per month, based on comparable rentals
Sale and tax history for 21384 Coopertown Rd
Sale History
Tax History
Date
Event
Price
BRIGHT MLS #MDTA2012516
Jun 1, 2026
Sold
$3,900,000
$278/sq ft
Jun 1, 2026
Sold
$3,900,000
$278/sq ft
May 29, 2026
Pending
—
Mar 3, 2026
Contingent
—
Dec 18, 2025
Listed
$5,200,000
$371/sq ft
As the MLS and public records start to fill up, we'll list the details here.
Public record
Beds
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Baths
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Stories
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Lot width
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Lot depth
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Lot size
—
Year renovated
—
Sq. Ft.
—
Year built
—
Style
Single Family Residential
County
Talbot County
APN
—
Parking Spaces
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Basement
—
Accessible
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HOA Dues
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Garage
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Features
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Last updated by owner on Apr 6, 2023.
Property details
Parking
Parking Information
Parking Lot
Interior
Bedroom Information
# of Bedrooms On 1st Upper Level: 10
# of Bedrooms On Main Level: 10
Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 10
# of Bathrooms (Half) On Main Level: 3
# of Bathrooms (Full) On Main Level: 11
# of Bathrooms (Full) On All Upper Levels: 10
# of Bathrooms (Half): 3
# of Bathrooms (Full): 21
Interior Information
Living Area Sq.Ft. Source: Assessor
Basement Information
Basement: No
Exterior
Property Information
Total Below Grade Sq. Ft.: 0
Accessibility Features: 2+ Access Exits
Ownership Interest: Fee Simple
Year Built Source: Assessor
Year Major Reno/Remodel: 2020
Building Information
Construction Materials: Frame
Other Structures: Above Grade, Below Grade
Pool Information
Personal Pool
Lot Information
Has Water View
Tidal Water: No
Above Grade Information
Finished Sq.Ft.: 14,035
Finished Sq.Ft. Source: Assessor
Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor
Financial
Tax Information
Tax Year: 2025
Assessments Information
Year Assessed: 2025
Utilities
Utilities Information
Central Air
Cooling Type: Central A/C, Ductless/Mini-Split
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Natural Gas
Hot Water: Multi-tank
Sewer Septic: Grinder Pump
Water Source: Well
Location
School Information
School District Name: TALBOT COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent
Location Information
Outside City Limits
Directions: Turn left onto the ramp toward US-50 E/US-301 N, then take the exit toward US-50 E/Ocean City. Turn right onto Easton Bypass (MD-322), then right again onto St Michaels Road (MD-33). Keep left to stay on MD-33/Tilghman Island Road, then turn right onto Coopertown Road and right again into The Tilghman Island Inn.
Public facts
Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: —
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Talbot County
APN: —
Home facts updated by county records on Apr 6, 2023
Around this home
Schools
Tilghman Elementary School
Public PreK-5 • Assigned • 0.4mi
2/10
St. Michaels Middle/High School
Public 6-12 • Assigned • 7.7mi
6/10
Provided by GreatSchools
Historical weather
Tilghman, MD • 21671
Average low and high temperatures (°F)
38
27
42
31
57
43
66
52
72
60
82
70
87
75
80
69
77
66
68
56
58
47
44
34
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
99/ 100
Exceptional sunlight
Sunscore
This home ranks in the top 11% for direct sun exposure in Tilghman. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10 hrs
6.5 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$4.86M – $5.88M
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