Leave a Message

By providing your contact information to Benson & Mangold Real Estate, your personal information will be processed in accordance with Benson & Mangold Real Estate's Privacy Policy. By checking the box(es) below, you expressly consent to receive marketing or promotional real estate communication from Benson & Mangold Real Estate in the manner selected by you. For SMS text messages, message frequency varies. Message and data rates may apply. Consent is not a condition of purchase of any goods or services. You may opt out of receiving further communications from Benson & Mangold Real Estate at any time. To opt out of receiving SMS text messages, reply STOP to unsubscribe. SMS text messaging is subject to our Terms of Use.

Thank you for your message. We will be in touch with you shortly.

Home Search

Property Description

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.

Overview

Property Status
For Sale
Lot Size
21.36 Acres
MLS ID
MDTA2014280
Property Type
Residential
Year Built
2007

Features & Amenities

Total Area
6,487 Sq.Ft.
Neighborhood
St. Michaels
Architecture Styles
Colonial
Water Frontage
Rip-Rap
Stories
3
Garage Spaces
5.0
Water Source
Well
Pool
No Pool
Parking
Detached Garage, Driveway, Attached Garage
Heat Type
Heat Pump(s)
Air Conditioning
Central A/C
Laundry Room
Main Floor
Fireplace
Gas/Propane
Appliances
Built-In Microwave, Built-In Range, Central Vacuum, Cooktop, Dishwasher, Dryer, Washer, Water Heater, Stainless Steel Appliances, Refrigerator, Oven - Wall, Extra Refrigerator/Freezer
Other 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
Sewer
Public Sewer
Substructure
Crawl Space
Disability Features
None
Other Exterior Features
Outbuilding(s)
School District
TALBOT COUNTY PUBLIC SCHOOLS
Sales Price
$2,995,000
Real Estate Tax
$15,421/yr
Zoning
RC

Downloads

8781 TILGHMAN ISLAND ROAD

Schedule a Tour

We would love to help you see this beautiful home! As a full-service brokerage, we can help you tour. Please submit an offer, and answer questions about the buying process.

Thank you

for your interest in 8781 TILGHMAN ISLAND ROAD, WITTMAN, MD 21676

8781 TILGHMAN ISLAND ROAD
Navigate
St. Michaels

Explore St. Michaels

A charming waterfront town on Maryland’s Eastern Shore, known for its maritime heritage, scenic harbor views, and relaxed coastal lifestyle.

read more

Mortgage Calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.
$0,000 Your Payment 20 15 65
$0,000 Your Payment

I'm Interested In

8781 TILGHMAN ISLAND ROAD

or
  • CallChuck Mangold Jr.

    License #74958

    (410) 924-8832
  • Featured Properties

    • 7508 COOPER POINT ROAD For Sale

      $7,500,000

      7508 COOPER POINT ROAD, BOZMAN, MD 21612

      • 6 Beds
      • 8 Baths
      • 8,476 Sq.Ft.
    • 24390 DEEP NECK FARM LANE For Sale

      $6,995,000

      24390 DEEP NECK FARM LANE, ROYAL OAK, MD 21662

      • 7 Beds
      • 6 Baths
      • 8,478 Sq.Ft.
    • 24679 DEEP NECK ROAD For Sale

      $6,495,000

      24679 DEEP NECK ROAD, ROYAL OAK, MD 21662

      • 4 Beds
      • 5 Baths
      • 6,731 Sq.Ft.
    • 7288 BOZMAN NEAVITT ROAD Active Under Contract

      $3,950,000

      7288 BOZMAN NEAVITT ROAD, BOZMAN, MD 21612

      • 4 Beds
      • 6 Baths
      • 6,963 Sq.Ft.
    • 24678 NEW POST ROAD For Sale

      $3,795,000

      24678 NEW POST ROAD, SAINT MICHAELS, MD 21663

      • 4 Beds
      • 5 Baths
      • 6,404 Sq.Ft.
    • 25610 CHANCE FARM COURT For Sale

      $3,595,000

      25610 CHANCE FARM COURT, ROYAL OAK, MD 21662

      • 5 Beds
      • 6 Baths
      • 5,947 Sq.Ft.
    • 5995 ELSTON SHORE ROAD Active Under Contract

      $3,295,000

      5995 ELSTON SHORE ROAD, NEAVITT, MD 21652

      • 5 Beds
      • 5 Baths
      • 4,843 Sq.Ft.
    • 601 COVE ROAD Pending

      $3,250,000

      601 COVE ROAD, SAINT MICHAELS, MD 21663

      • 4 Beds
      • 5 Baths
      • 3,289 Sq.Ft.
    • 23961 LYNNEWOOD DRIVE For Sale

      $3,100,000

      23961 LYNNEWOOD DRIVE, SAINT MICHAELS, MD 21663

      • 4 Beds
      • 4 Baths
      • 4,035 Sq.Ft.
    • 7543 BOZMAN NEAVITT ROAD For Sale

      $2,750,000

      7543 BOZMAN NEAVITT ROAD, BOZMAN, MD 21612

      • 4 Beds
      • 3 Baths
      • 6,361 Sq.Ft.
    • 24878 W FERRY NECK ROAD Pending

      $2,495,000

      24878 W FERRY NECK ROAD, ROYAL OAK, MD 21662

      • 3 Beds
      • 3 Baths
      • 2,663 Sq.Ft.
    • 203 CHEW AVENUE E Pending

      $2,195,000

      203 CHEW AVENUE E, SAINT MICHAELS, MD 21663

      • 5 Beds
      • 6 Baths
      • 4,673 Sq.Ft.
    • 7421 QUAKER NECK ROAD For Sale

      $1,995,000

      7421 QUAKER NECK ROAD, BOZMAN, MD 21612

      • 6 Beds
      • 5 Baths
      • 4,352 Sq.Ft.
    • 9020 BOZMAN NEAVITT ROAD For Sale

      $1,995,000

      9020 BOZMAN NEAVITT ROAD, SAINT MICHAELS, MD 21663

      • 4 Beds
      • 3 Baths
      • 3,028 Sq.Ft.
    • 9788 PINTAIL PL Active Under Contract

      $1,895,000

      9788 PINTAIL PL, SAINT MICHAELS, MD 21663

      • 4 Beds
      • 3 Baths
      • 2,320 Sq.Ft.
    • 24390 OAKWOOD PARK ROAD For Sale

      $1,679,000

      24390 OAKWOOD PARK ROAD, SAINT MICHAELS, MD 21663

      • 4 Beds
      • 4 Baths
      • 2,839 Sq.Ft.
    • 602 LANDING Active Under Contract

      $1,650,000

      602 LANDING ROAD, SAINT MICHAELS, MD 21663

      • 3 Beds
      • 3 Baths
      • 3,078 Sq.Ft.
    • 9251 MALLARD POINT COURT For Sale

      $1,295,000

      9251 MALLARD POINT COURT, MCDANIEL, MD 21647

      • 3 Beds
      • 3 Baths
      • 1,816 Sq.Ft.
    • 114 E CHESTNUT STREET For Sale

      $1,195,000

      114 W CHESTNUT STREET, SAINT MICHAELS, MD 21663

      • 4 Beds
      • 5 Baths
      • 3,528 Sq.Ft.
    • 109 W MARENGO STREET For Sale

      $1,049,000

      109 W MARENGO STREET, SAINT MICHAELS, MD 21663

      • 4 Beds
      • 3 Baths
      • 2,250 Sq.Ft.
    • 504 SEYMOUR AVENUE For Sale

      $1,049,000

      504 SEYMOUR AVENUE, SAINT MICHAELS, MD 21663

      • 3 Beds
      • 3 Baths
      • 2,200 Sq.Ft.
    • 8684 SEWELL POINT ROAD Pending

      $995,000

      8684 SEWELL POINT ROAD, WITTMAN, MD 21676

      • 3 Beds
      • 3 Baths
      • 2,016 Sq.Ft.
    • 8090 BOZMAN NEAVITT ROAD For Sale

      $993,000

      8090 BOZMAN NEAVITT ROAD, BOZMAN, MD 21612

      • 3 Beds
      • 2 Baths
      • 1,362 Sq.Ft.
    • 25826 Orchard Ter For Sale

      $850,000

      25826 ORCHARD TERRACE, ROYAL OAK, MD 21662

    • 6355 BOZMAN NEAVITT For Sale

      $849,900

      6355 BOZMAN NEAVITT, NEAVITT, MD 21652

      • 3 Beds
      • 2 Baths
      • 1,176 Sq.Ft.
    • 25831 TURNER AVENUE For Sale

      $774,000

      25831 TURNER AVENUE, ROYAL OAK, MD 21662

      • 3 Beds
      • 3 Baths
      • 2,200 Sq.Ft.
    • 24965 BACK CREEK DRIVE For Sale

      $739,000

      24965 BACK CREEK DRIVE, ST MICHAELS, MD 21663

      • 4 Beds
      • 3 Baths
      • 2,798 Sq.Ft.
    • 21869 ALBIE ROAD For Sale

      $575,000

      21869 ALBIE ROAD, SHERWOOD, MD 21665

      • 3 Beds
      • 2 Baths
      • 1,680 Sq.Ft.
    • 6705 TILGHMAN ISLAND ROAD For Sale

      $575,000

      6705 TILGHMAN ISLAND ROAD, SHERWOOD, MD 21665

      • 4 Beds
      • 3 Baths
      • 2,424 Sq.Ft.
    • 8000 BOZMAN NEAVITT ROAD For Sale

      $499,000

      8000 BOZMAN NEAVITT ROAD, BOZMAN, MD 21612

      • 3 Beds
      • 2 Baths
      • 1,761 Sq.Ft.
    • 934 CALVERT AVENUE Pending

      $499,000

      934 CALVERT AVENUE, ST MICHAELS, MD 21663

      • 3 Beds
      • 2 Baths
      • 1,574 Sq.Ft.
    • 8658 CUMMINGS ROAD For Sale

      $495,000

      8658 CUMMINGS ROAD, WITTMAN, MD 21676

      • 3 Beds
      • 2 Baths
      • 1,664 Sq.Ft.
    • 9518 QUAIL HOLLOW 702 For Sale

      $455,000

      9518 QUAIL HOLLOW 702, SAINT MICHAELS, MD 21663

      • 3 Beds
      • 3 Baths
      • 1,800 Sq.Ft.
    • 6390 BOZMAN NEAVITT ROAD For Sale

      $449,000

      6390 BOZMAN NEAVITT ROAD, NEAVITT, MD 21652

      • 3 Beds
      • 2 Baths
      • 1,520 Sq.Ft.
    • 101 BROOKS LANE For Sale

      $425,000

      101 BROOKS LANE, SAINT MICHAELS, MD 21663

      • 3 Beds
      • 2 Baths
      • 1,120 Sq.Ft.
    • 8805 CUMMINGS ROAD For Sale

      $375,000

      8805 CUMMINGS ROAD, WITTMAN, MD 21676

      • 2 Beds
      • 2 Baths
      • 1,364 Sq.Ft.
    • 5658 GATES STREET For Sale

      $365,000

      5658 GATES STREET, ROYAL OAK, MD 21662

      • 3 Beds
      • 2 Baths
      • 1,480 Sq.Ft.
    • 108 MILES AVENUE For Sale

      $295,000

      108 MILES AVENUE, SAINT MICHAELS, MD 21663

    • 25835 TURNER AVENUE For Sale

      $210,400

      25835 TURNER AVENUE, ROYAL OAK, MD 21662

    • 21891 SHERWOOD LANDING ROAD For Sale

      $155,000

      21891 SHERWOOD LANDING ROAD, SHERWOOD, MD 21665

      • 2 Beds
      • 1 Bath
      • 1,304 Sq.Ft.
    • 7998 BOZMAN NEAVITT ROAD Pending

      $149,000

      7998 BOZMAN NEAVITT ROAD, BOZMAN, MD 21612

      • 1,200 Sq.Ft.
    • 25832 TURNER AVENUE For Sale

      $147,200

      25832 TURNER AVENUE, ROYAL OAK, MD 21662

    • 25833 TURNER AVENUE For Sale

      $126,400

      25833 TURNER AVENUE, ROYAL OAK, MD 21662

    • 107 S TALBOT For Lease

      $3,500/mo

      107 S TALBOT, ST MICHAELS, MD 21663

    • 310 TALBOT For Lease

      $3,500/mo

      310 TALBOT STREET, SAINT MICHAELS, MD 21663

      • 2,364 Sq.Ft.
    • 101 BROOKS LANE For Lease

      $2,500/mo

      101 BROOKS LANE, SAINT MICHAELS, MD 21663

      • 3 Beds
      • 2 Baths
      • 1,120 Sq.Ft.
    • 203 E. Chew Avenue For Sale

      Price Upon Request

      203 E. Chew Avenue, St, Michaels, MD 21663

    View All Properties

    Follow Us On Instagram