Listed By:
Benson & Mangold, LLC
27295 Southside Island Creek Road, Trappe, MD
$ 8,800,000
Property Attributes
  • MLS#MDTA2006798
  • TypeSingle Family
  • CountyTALBOT
  • CityTrappe
  • NeighborhoodTrappe
  • Zip21673
  • StyleTraditional
  • Year Built1800
  • Taxes$ 23991
  • Price$ 8,800,000
  • Bedrooms6
  • Full Bathrooms4
  • Half Bathrooms2
  • Sqr Footage9566
  • Lot Size47.99 Acres
Data Source:
Bright MLS
Property Description

Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47 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 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 owners grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Marylands 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 houses 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 houses 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 artists studio with cabinetry and sink that has a myriad uses family 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.

Price History
12/22/2023 Listed $8,800,000

General Features

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
Sewer On Site Septic
Heating Zoned,Forced Air
Cooling Geothermal,Central A/C,Ductless/Mini-Split
Utilities Phone
Possession Settlement
Roof Metal
Appliances Stove,Refrigerator,Dishwasher,Washer,Dryer
Exterior Features Boat Storage,Extensive Hardscape,Exterior Lighting,Kennels,Outbuilding(s),Private Beach,Tennis Court(s),Other
Zoning A2
Pool Y/N Yes - Personal
Patio/Porch Features Porch(es),Brick
Architectural Style Traditional
Pool Features Concrete
Security Features Resident Manager,Exterior Cameras
Construction Materials Brick
Year Built 1800
Electric 200+ Amp Service
View Water,Scenic Vista,River,Pasture,Panoramic,Bay
Levels 3
Tax Year 2024
Percent Ownership Fee Simple
Cool Fuel Geothermal,Electric
Waterfront Features Rip-Rap,Sandy Beach
Accessibility None
New Construction No
Property Type Residential
HOA / Comm Assn No
Subdivision Name TRAPPE
Facing Direction South
Garage Y/N No
Water Access Y/N Yes
Other Structures Above Grade,Below Grade
Total Rooms 24
Directions RT 50,turn West onto Sanderstown Rd,turn right onto Island Creek,turn left onto S. Side Island Creek. Property on left,first entry to house,second to barns and beach house. By Appointment Only.
ModificationTimestamp 2024-03-22T15:02:12
Buyer Agent Compensation 2.5
Body of Water Choptank River
Disclosures Lead Based Paint - Federal,Historic Property
Senior Community Y/N No
Lot Size Square Feet 2090444.40
Tax Assessed Value 2804600.0
Waterfront Y/N Yes
Tax Annual Amount 23991.0
Home Warranty Y/N No
Property Condition Excellent
Structure Type Detached
Condo/Coop Association Y/N No
Bathrooms Count Main Level 2.00
Price Per Sq Ft 919.92
Additional Parcels Y/N No
Historic Y/N Yes
Lease Considered Y/N No
Vacation Rental Y/N No
Virtual Tour
Total SQFT 9566
Days on Market 117
Location Type River
Standard Status Active
Year Built Source Assessor
Legal Subdivision *
Buyer Agent Compensation Type % Of Gross

Interior Features

Heating Fuel Oil,Geo-thermal
Basement Drainage System,Partial,Poured Concrete,Sump Pump,Unfinished,Workshop,Other
Flooring Wood
Total Fireplaces 8
Hot Water Oil
Basement (Y/N) Yes
Heating Y/N Yes
Fireplace Y/N Yes
Above Grade Finished Area 9566
Full Baths 4
Half Baths 2
Street Suffix ROAD
Central Air Y/N Yes
Total Bedrooms 6
Room Type Living Room,Dining Room,Primary Bedroom,Bedroom 2,Bedroom 3,Bedroom 4,Bedroom 5,Kitchen,Den,Foyer,Breakfast Room,Study,Sun/Florida Room,Recreation Room,Bedroom 6,Bathroom 2,Bathroom 3,Primary Bathroo
Below Grade Finished Area Unit Type Square Feet
LivingAreaSource Assessor
Below Grade Unfin Area Units Square Feet
Below Grade Unfin SQFT Source Assessor
Below Grade Finished Area Source Assessor
Bedrooms Count All Upper Levels 6
Bedrooms Count Upper Level 1 3
Bedrooms Count Upper Level 2 3
Bathrooms Half Main Level 2
Bathrooms Full Upper Level 2 1
Bathrooms Full Upper Level 1 3
Bathrooms Full All Upper Levels 4
Bathrooms Count Upper Level 2 1.00
Bathrooms Count Upper Level 1 3.00
Bathrooms Count All Upper Levels 4
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 6

Exterior Features

Lot Features Rural,Fishing Available,Hunting Available,Landscaping,Open,Partly Wooded,Pond,Premium,Private
Water Source Well
Type of Parking Other
Foundation Details Brick/Mortar
Spa No
Water View Y/N Yes
Lot Size Acres 47.99
Water Body Type River
Lot Size Units Square Feet
Lot Size Source Estimated
Water Access Features Sail,Canoe/Kayak,Fishing Allowed,Boat - Powered,Personal Watercraft (PWC),Private Access
Number of Docks 1
Land Assessed Value 2034300.00
Navigable Water Y/N Yes
Number of Slips 3
Water Oriented Y/N Yes
Dock/Slip Conveys YN Yes
Dock Type and Features Private,Storage Area,Material - Treated Lumber,Hoist/Lift Electric,Pier (Perpendicular)

Room Details

Room Dimensions Level Flooring Details
Bathroom 2 Upper 1
Bathroom 3 Upper 1
Bedroom 2 Upper 1
Bedroom 3 Upper 1
Bedroom 4 Upper 2
Bedroom 5 Upper 2
Bedroom 6 Upper 2
Breakfast Room Main
Den Main
Dining Room Main
Foyer Main
Full Bath Upper 2
Kitchen Upper 1
Kitchen Main
Living Room Main
Living Room Upper 1
Primary Bathroom Upper 1
Primary Bedroom Upper 1
Recreation Room Upper 2
Study Main
Sun/Florida Room Main


  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Property vs Single Family Average in 21673

AVG $1.97M
AVG $8,521
AVG 214
Data Provided by Inside Real Estate®
Year Built
AVG 1978