27295 SOUTHSIDE ISLAND CREEK ROAD, TRAPPE, MD 21673

$8,750,000

Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the… Read More Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look and appreciation for the scope of this offering. The main house has great historical significance not only for the original owner's grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland's domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house's architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house's majestic specimen trees around the property, including a gigantic Sycamore that is the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist's studio with cabinetry and sink that has a myriad uses- TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite. The revised offering of The Wilderness, providing 234 acres comprised of 5 recorded parcels with over 3,000 feet of shoreline is a remarkable opportunity to witness life on the Shore. Read Less

Courtesy of Coard A Benson, Benson & Mangold, LLC 410-770-9255

Listing Snapshot

Days Online

741

Last Updated

Jan 15, 2026

Property Type

Single Family Residential

Beds

Full Baths

Partial Baths

Square Ft.

9,566

Lot Size

234 Acres

Year Built

1800

MLS Number

MDTA2006798

Additional Details

Appliances & Equipment

Stove, Refrigerator, Dishwasher, Washer, Dryer

Basement

Drainage System, Partial, Poured Concrete, Sump Pump, Unfinished, Workshop

Building

Built in 1800, Living area: 9566, Building faces South, Levels: 3, Construction Materials: Brick

Cooling

Geothermal, Central A/C, Ductless/Mini-Split

Accessibility Features

None

Exterior Features

Patio/Porch Features: Porch(es), Brick, Boat Storage, Extensive Hardscape, Exterior Lighting, Kennels, Outbuilding(s), Private Beach, Tennis Court(s)

Fireplaces

8 fireplaces

Floors

Wood

Foundation

Brick/Mortar

Heating

Zoned, Forced Air

Interior Features

2nd Kitchen, Additional Stairway, Breakfast Area, Built-Ins, Butlers Pantry, Floor Plan - Traditional, Formal/Separate Dining Room, Kitchen - Country, Kitchen - Eat-In, Wood Floors

Lot

234 acres, Rural, Fishing Available, Hunting Available, Landscaping, Open, Partly Wooded, Pond, Premium, Private

Pool

Concrete

Property

Excellent, Other structures: Above Grade, Below Grade, Water, Scenic Vista, River, Pasture, Panoramic, Bay

Roof

Metal

Security Features

Resident Manager, Exterior Cameras

Sewer

On Site Septic

Taxes

Additional parcels description:, Annual Amount: $26,077, Year: 2024, Zoning: A2

Utilities

Phone, Water Source: Well, 200+ Amp Service

Water Features

Water Body Name: Choptank River, Rip-Rap, Sandy Beach

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Heather Brummell