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.
Pending
$2,995,000
8781 Tilghman Island Rd, Wittman, MD 21676
5beds
6,487sqft
:
Get pre-qualified$19,763/mo
Single Family Residence
Built in 2007
21.36 Acres Lot
$2,840,700 Zestimate®
$462/sqft
$-- HOA
What's special
Unforgettable western sunsetsStacked waterfront porchesExtraordinary waterfront settingTwo gas fireplacesTimeless brick exteriorWalk-in closetAbundant storage
- 26 days |
- 1,036 |
- 44 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Chuck Mangold JR. 410-924-8832,
Benson & Mangold, LLC 4108226665
Source: Bright MLS,MLS#: MDTA2014280
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
- Main level bathrooms: 2
- Main level bedrooms: 1
Rooms
- Room types: 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
Primary bedroom
- Features: Flooring - HardWood
- Level: Main
- Area: 360 Square Feet
- Dimensions: 18 X 20
Bedroom 2
- Level: Upper
- Area: 224 Square Feet
- Dimensions: 14 X 16
Bedroom 3
- Level: Upper
- Area: 210 Square Feet
- Dimensions: 14 X 15
Bedroom 4
- Level: Upper
- Area: 266 Square Feet
- Dimensions: 14 X 19
Bedroom 5
- Level: Upper
- Area: 272 Square Feet
- Dimensions: 17 X 16
Bonus room
- Level: Upper
- Area: 192 Square Feet
- Dimensions: 16 X 12
Dining room
- Features: Flooring - HardWood
- Level: Main
- Area: 357 Square Feet
- Dimensions: 17 X 21
Kitchen
- Features: Kitchen Island, Kitchen - Gas Cooking
- Level: Main
- Area: 304 Square Feet
- Dimensions: 16 X 19
Living room
- Features: Flooring - HardWood, Fireplace - Gas
- Level: Main
- Area: 462 Square Feet
- Dimensions: 21 X 22
Office
- Features: Built-in Features
- Level: Upper
- Area: 266 Square Feet
- Dimensions: 14 X 19
Sitting room
- Features: Fireplace - Gas
- Level: Upper
- Area: 399 Square Feet
- Dimensions: 19 X 21
Storage room
- Features: Attic - Finished
- Level: Upper
- Area: 462 Square Feet
- Dimensions: 14 X 33
Other
- Level: Main
- Area: 420 Square Feet
- Dimensions: 10 X 42
Heating
- Heat Pump, Electric
Cooling
- Central Air, Electric
Appliances
- Included: Microwave, Built-In Range, Central Vacuum, Cooktop, Dishwasher, Dryer, Washer, Water Heater, Stainless Steel Appliance(s), Refrigerator, Oven, Extra Refrigerator/Freezer, Electric Water Heater
- Laundry: Main Level
Features
- Attic, Bathroom - Walk-In Shower, Bathroom - Tub Shower, Built-in Features, 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)
- Flooring: Carpet, Wood
- Has basement: No
- Number of fireplaces: 2
- Fireplace features: Gas/Propane
Interior area
- Total structure area: 6,487
- Total interior livable area: 6,487 sqft
- Finished area above ground: 6,487
- Finished area below ground: 0
Video & virtual tour
Property
Parking
- Total spaces: 11
- Parking features: Garage Faces Side, Inside Entrance, Asphalt, Detached, Driveway, Attached
- Attached garage spaces: 5
- Uncovered spaces: 6
Accessibility
- Accessibility features: None
Features
- Levels: Three
- Stories: 3
- Patio & porch: Brick, Patio, Porch, Enclosed
- Exterior features: Balcony
- Pool features: None
- On waterfront: Yes
- Waterfront features: Rip-Rap, Bay
- Frontage length: Water Frontage Ft: 662
Lot
- Size: 21.36 Acres
Details
- Additional structures: Above Grade, Below Grade, Outbuilding
- Parcel number: 2105185726
- Zoning: RC
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Brick
- Foundation: Crawl Space
Condition
- New construction: No
- Year built: 2007
Utilities & green energy
- Sewer: Public Sewer
- Water: Well
Community & HOA
Community
- Subdivision: Wittman
HOA
- Has HOA: No
Location
- Region: Wittman
Financial & listing details
- Price per square foot: $462/sqft
- Tax assessed value: $1,870,300
- Annual tax amount: $15,421
- Date on market: 7/2/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
$2,840,700
$2.70M - $2.98M
$5,180/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/17/2026 | Pending sale | $2,995,000$462/sqft |
Source:  Bright MLS #MDTA2014280 Report a problem | ||
| 7/2/2026 | Listed for sale | $2,995,000-14.3%$462/sqft |
Source: Bright MLS #MDTA2014280 Report a problem | ||
| 6/24/2026 | Listing removed | $3,495,000$539/sqft |
Source: Bright MLS #MDTA2011878 Report a problem | ||
| 5/25/2026 | Price change | $3,495,000-4.2%$539/sqft |
Source: Bright MLS #MDTA2011878 Report a problem | ||
| 3/24/2026 | Price change | $3,650,000-3.8%$563/sqft |
Source: Bright MLS #MDTA2011878 Report a problem | ||
| 10/6/2025 | Price change | $3,795,000-2.6%$585/sqft |
Source: Bright MLS #MDTA2011878 Report a problem | ||
| 10/3/2025 | Listed for sale | $3,895,000-2.5%$600/sqft |
Source: Bright MLS #MDTA2011878 Report a problem | ||
| 7/22/2024 | Listing removed | -- |
Source: Bright MLS #MDTA2007354 Report a problem | ||
| 3/20/2024 | Listed for sale | $3,995,000+305.6%$616/sqft |
Source: Bright MLS #MDTA2007354 Report a problem | ||
| 1/18/2006 | Sold | $985,000$152/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $1,685,000 +6.2% |
| 2024 | $14,331 +12.5% | $1,587,000 +6.6% |
| 2023 | $12,737 +15.3% | $1,489,000 +7% |
| 2022 | $11,045 +8.1% | $1,391,000 +2% |
| 2021 | $10,219 +2% | $1,363,967 +2% |
| 2020 | $10,016 +2.1% | $1,336,933 +2.1% |
| 2019 | $9,814 +4.3% | $1,309,900 |
| 2018 | $9,406 +5.2% | $1,309,900 |
| 2017 | $8,944 +1.9% | $1,309,900 -4.1% |
| 2016 | $8,777 | $1,365,800 |
| 2015 | $8,777 +11.7% | $1,365,800 |
| 2014 | $7,855 | $1,365,800 -3.4% |
| 2013 | -- | $1,414,000 |
| 2012 | -- | $1,414,000 |
| 2011 | -- | $1,414,000 -25.5% |
| 2010 | -- | $1,898,310 +7.1% |
| 2009 | -- | $1,772,412 +3.6% |
| 2008 | -- | $1,711,406 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 21676
Nearby schools
GreatSchools rating
- 4/10Tilghman Elementary SchoolGrades: PK-5Distance: 5.8 mi
- 5/10St. Michaels Middle/High SchoolGrades: 6-12Distance: 5.1 mi
Schools provided by the listing agent
- District: Talbot County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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