top of page
main house.jpg

Circa 1780

A historical marker and cornerstone for American history on Maryland’s Eastern Shore, The Wilderness provides a commanding presence among old-growth trees along the Choptank River with broad southerly views.  With original structures that are impeccably well-kept and improved with modern amenities, The Wilderness represents a unique opportunity to enjoy the best of the Eastern Shore.

 

This offering is comprised of 47±acres.  As part of a 1659 land patent from Lord Baltimore, the farm has been maintained for generations preserving its rural and agricultural heritage.  

 ​Tax Map 57 | Parcel 11

Wilderness Estate

27293 Southside Island Creek Road

Trappe, Maryland 21673

RESOURCES

PROPERTY HIGHLIGHTS

BARN
The distinctive barn was constructed in 1912. Beginning in 1967 and spanning more than two decades, it was carefully restored to reflect the style of the Victorian era during which it was originally constructed. The barn is a combination of alternating red and green doors and trim on bright white. Additional outbuildings include an original corn crib, oil shed, sheep shed, workshop, dairy and smokehouse.

RESIDENCE
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. 
Floorplan

BEACH HOUSE
Just steps away from the expansive 1,700 foot shoreline and beach, the two-story Beach House offers water views and tranquility in a private setting.  At approximately 2,182 square feet, the main living areas are on the first floor, including the kitchen, dining, living room, laundry, bath, and mudroom. 
On the second floor, there are three spacious bedrooms and two full baths. 

Beach House Floorplan
Guest Cottage Floorplan

WATERFRONT & GROUNDS
The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. The 400-foot pier extends from a sandy beach with kayak and canoe racks. With eight feet of water depth, this pier is perfect for the sailing and yacht enthusiast. Entertain guests with an array of other outdoor features, including the pool, tennis court, putting green, croquet court and more. A two-bedroom waterfront guest cottage and a one-bedroom pool house provide additional accommodations for extended stays.

reach out

Quick Contact

Easton, Maryland natives, Coard and Schuyler Benson are experts in Eastern Shore real estate

drawing of house
  • Facebook
  • YouTube
  • Instagram
  • LinkedIn

Coard Benson, Associate Broker at Benson & Mangold

contact

(410) 310-4909

(410) 770-9255

coard@coardbenson.com

24 N. Washington St. Easton, MD 21601

useful links

business logo

Copyright 2025© All Rights Reserved

 business logo
The Country School logo
Ducks Unlimited logo
Young Life logo

All information herein is believed to be accurate, but should not be relied upon without verification. Listing information is provided courtesy of The Metropolitan Regional Information Systems, which neither guarantees nor is in any way responsible for its accuracy. The data relating to real estate for sale on this website comes in part from the Broker Reciprocity Program of The Metropolitan Regional Information Systems. The materials contained within this page may not be reproduced without the express written consent of this broker. The information contained within this page is for personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All room dimensions and other measurements are approximate. All information is deemed reliable but is not guaranteed. Prospective purchasers should verify the information to their own satisfaction. All data is provided 'AS IS' and with all faults. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Some real estate firms do not participate in Internet Data Exchange®, and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Some or all of the listings displayed may not belong to the firm whose website is being visited. Information deemed reliable but not guaranteed. | Benson and Mangold Real Estate is licensed in Maryland. © Benson and Mangold Real Estate and its related entities. An independently owned and operated business used under licenses. Equal Housing Opportunity.

bottom of page