8781 Tilghman Island Road • Wittman, MD 21676

$2,995,000 Beds: 5 • Baths: 5 full 1 partial • Sq. Feet: 6487 • MLS ID: MDTA2014280 • Subdivision: WITTMAN • School Dist: TALBOT COUNTY PUBLIC SCHOOLS
8781 Tilghman Island Road presents a rare opportunity to own a custom-designed, Daffin-built Chesapeake Bay estate set on 21±acres between historic St. Michaels and Tilghman Island. Constructed with a timeless brick exterior and encompassing approximately 6,500± square feet, this five-bedroom, five-and-a-half-bath residence was thoughtfully designed to embrace its extraordinary waterfront 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 662± 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 21± 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. View this listing at: http://www.bobspeelmanrealtor.com/mls=MDTA2014280

Property Features

  • Garage: 5
  • Taxes: $15,421
  • Exterior: Brick
  • Parking Notes: 11 Total Parking Spaces
  • Lot Size: 21.36 Acres
  • Lot Dimensions: 21.36 Acre(S)
  • Heating: Heat Pump(s)
  • Fuel Type: Electric
  • Cooling: Central A/C
  • Year Built: 2007
  • Fireplaces: 2
  • Water: Well
  • Sewer: Public Sewer
  • Stories: 3.0
  • Additional Structures: Above Grade,Below Grade
  • Structure Type: Detached
  • Total Garage/Parking Spaces: 11
  • Parking Features: Asphalt Driveway
  • Appliances: Built-In Microwave,Built-In Range,Central Vacuum,Cooktop,Dishwasher,Dryer,Washer,Water Heater,Stainless Steel Appliances,Refrigerator,Oven - Wall,Extra Refrigerator/Freezer
  • Rooms: Living Room,Dining Room,Primary Bedroom,Sitting Room,Bedroom 2,Bedroom 3,Bedroom 4,Bedroom 5,Kitchen,Sun/Florida Room,Office,Storage Room,Bonus Room
  • SQFT Total Finished: 6487
  • SQFT Above Finished: 6487
  • Exterior: Outbuilding(s)
  • Interior: 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
  • Fireplace: Gas/Propane
  • Waterfront: Rip-Rap

Room Sizes

  • Living Room: 22 x 21 Level: Main
  • Primary Bedroom: 20 x 18 Level: Main
  • Dining Room: 21 x 17 Level: Main
  • Sun/Florida Room: 42 x 10 Level: Main
  • Kitchen: 19 x 16 Level: Main
  • Bedroom 2: 16 x 14 Level: Upper 1
  • Bedroom 3: 15 x 14 Level: Upper 1
  • Bedroom 4: 19 x 14 Level: Upper 1
  • Office: 19 x 14 Level: Upper 1
  • Sitting Room: 21 x 19 Level: Upper 1
  • Storage Room: 33 x 14 Level: Upper 1
  • Bedroom 5: 16 x 17 Level: Upper 2
  • Bonus Room: 12 x 16 Level: Upper 2

School Information

  • School District: TALBOT COUNTY PUBLIC SCHOOLS
Printed July 03, 2026


Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 07/03/2026. The listing information on this page last changed on 07/03/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 07/03/2026 12:05:06 AM EST) or Bright MLS (last updated Thu 07/02/2026 11:57:42 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
Privacy Policy / DMCA Notice / ADA Accessibility
Federal Housing Equal Opportunity Realtor
Corporate Office - 215 S Centerville Rd. Lancaster, PA 17603
James J Hafer - West Virginia Broker of Record

©2026 BHH Affiliates, LLC. An independently owned and operated franchisee of BHH Affiliates, LLC. Berkshire Hathaway HomeServices and the Berkshire Hathaway HomeServices symbol are registered service marks of Columbia Insurance Company, a Berkshire Hathaway affiliate. Equal Housing Opportunity.


Agent License Information: 
Licensed in Pennsylvania & Maryland
Bob Speelman 

11949 Robinwood Drive #100, Hagerstown, MD 21742
301-745-1620