8781 TILGHMAN ISLAND ROAD, WITTMAN, MD 21676

$2,995,000

8781 Tilghman Island Road presents a rare opportunity to own a custom-designed, Daffin-built Chesapeake Bay estate set on 21b1;acres between historic St. Michaels and Tilghman Island. Constructed with a timeless brick exterior and encompassing approximately 6,500b1; square feet, this five-bedroom, five-and-a-half-bath residence was thoughtfully designed to embrace its extraordinary waterfront… Read More setting, where expansive Chesapeake Bay views and unforgettable western sunsets become part of everyday life. The home's classic architecture is highlighted by stacked waterfront porches, a spacious front balcony, and walls of windows that capture panoramic views from nearly every principal room. Two gas fireplaces add warmth to the generous living spaces, while abundant storage and a thoughtful floor plan provide comfort and functionality for both everyday living and entertaining. The main level is anchored by a spacious waterfront primary suite featuring a walk-in closet, oversized water closet, an en-suite bath with a tile walk-in shower and a separate tub, and a private enclosed porch overlooking the Bay. Upstairs, three generously sized en-suite bedrooms offer exceptional accommodations. Two bedrooms open to the front balcony, while the waterfront suite enjoys direct access to the upper waterfront porch. The third floor offers an additional en-suite bedroom along with a versatile bonus room ideal as a home office, craft room, playroom, fitness space, or additional storage. Outside, approximately 662b1; feet of riprapped Chesapeake Bay shoreline frames the property, while mature trees create a beautiful natural setting. Approximately four acres lie outside of the agricultural assessment, with the remaining acreage benefiting from agricultural tax status. Positioned along the Eastern Bay Water Trail, the property offers experienced kayakers direct access to one of the region's premier paddling routes and the opportunity to explore the Chesapeake Bay from your own shoreline. A detached garage offers exceptional flexibility and could serve as a future pool house, workshop, studio, or, where permitted, guest accommodations. The home is equipped with five-zone heat pumps with central air conditioning, along with separate ductless HVAC systems serving both waterfront porches and the detached garage, providing year-round comfort throughout the property. Combining quality craftsmanship, a premier Chesapeake Bay location, and over 21b1; acres of land, this exceptional waterfront estate offers an increasingly rare opportunity to enjoy privacy, space, and some of the Eastern Shore's most spectacular sunset views. Read Less

Courtesy of Chuck V Mangold Jr., Benson & Mangold, LLC 410-822-6665

Listing Snapshot

Days Online

Last Updated

Jul 17, 2026

Property Type

Single Family Residential

Beds

Full Baths

Partial Baths

Square Ft.

6,487

Lot Size

21.36 Acres

Year Built

2007

MLS Number

MDTA2014280

Additional Details

Appliances & Equipment

Built-In Microwave, Built-In Range, Central Vacuum, Cooktop, Dishwasher, Dryer, Washer, Water Heater, Stainless Steel Appliances, Refrigerator, Oven - Wall, Extra Refrigerator/Freezer

Building

Built in 2007, Living area: 6487, Levels: 3, Construction Materials: Brick

Cooling

Central A/C

Accessibility Features

None

Exterior Features

Patio/Porch Features: Balcony, Brick, Patio(s), Porch(es), Enclosed, Outbuilding(s)

Fireplaces

2 fireplaces, Gas/Propane

Foundation

Crawl Space

Garage

5 spaces

Heating

Heat Pump(s)

Interior Features

Attic, Bathroom - Walk-In Shower, Bathroom - Tub Shower, Built-Ins, Carpet, Ceiling Fan(s), Central Vacuum, Dining Area, Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Island, Primary Bath(s), Primary Bedroom - Bay Front, Walk-in Closet(s), Wood Floors

Lot

21.36 acres

Parking

Asphalt Driveway

Property

Other structures: Above Grade, Below Grade

Sewer

Public Sewer

Taxes

Annual Amount: $15,421, Year: 2025, Zoning: RC

Utilities

Water Source: Well

Water Features

Rip-Rap

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