4440 Baildon Road
Trappe, MD 21673

$2,895,000

Beds: 4
Baths: 3 full 2 partial
Sq. Feet: 3589
MLS ID: MDTA2014482
Subdivision: BAILDON
School Dist: TALBOT COUNTY PUBLIC SCHOOLS
With sweeping sunset views, this picturesque estate—perfectly sited on a deepwater point with a private dock on Island Creek just off the Choptank River—offers the rare combination of privacy, acreage, and refined Eastern Shore living. Just ten minutes from Easton, Oxford, and Cambridge, the property features an impressive two‑story Tidewater Colonial of approximately 3,500± fsf that includes a first‑floor primary suite with a private library, multiple walk‑in closets, and a beautifully finished bath; two additional bedrooms and full bath upstairs; a guest apartment with separate kitchenette, bedroom and full bath; a large two‑car garage; and a stunning concrete pool framed by expansive stone patios. The current owners thoughtfully reimagined and upgraded the interior, relocating the kitchen to the waterside, expanding and renovating the spacious family room and first‑floor primary suite, adding an exceptional bar/butler’s pantry with custom cabinetry, refrigerator, dishwasher, and icemaker, and creating a central multi-purpose laundry room. Exterior features include low‑maintenance brick and siding, new roof on the renovated waterside, paved drive with ample parking, and an attached two‑car garage with a separate climate‑controlled workout room and half bath. The fully protected, riprapped shoreline spans approximately 665 feet and features a new pier with two deepwater slips (6’+ MLW), electric and water service, plus a separate kayak dock and launch. From any of the property’s many vantage points, enjoy majestic shade trees, mature landscaping, and an ever-changing panorama of natural beauty—schools of fish, abundant waterfowl, and diverse wildlife—making this an ideal Eastern Shore retreat. View this listing at: http://markhess.homesale.com/mls=MDTA2014482

Property Features

Room Sizes

School Information

  • High School: EASTON
  • Elementary School: WHITE MARSH
  • School District: TALBOT COUNTY PUBLIC SCHOOLS
Printed July 14, 2026


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Mark Hess 

16 Greenmeadow Drive, Suite 300, Timonium, MD 21093
410-561-0044