27295 Southside Island Creek Rd, Trappe, MD 21673
Local realty services provided by:ERA OakCrest Realty, Inc.
27295 Southside Island Creek Rd,Trappe, MD 21673
$8,750,000
- 6 Beds
- 6 Baths
- 9,566 sq. ft.
- Single family
- Active
Listed by: coard a benson, schuyler g. benson
Office: benson & mangold, llc.
MLS#:MDTA2006798
Source:BRIGHTMLS
Price summary
- Price:$8,750,000
- Price per sq. ft.:$914.7
About this home
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 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....
Contact an agent
Home facts
- Year built:1800
- Listing ID #:MDTA2006798
- Added:814 day(s) ago
- Updated:March 16, 2026 at 01:41 PM
Rooms and interior
- Bedrooms:6
- Total bathrooms:6
- Full bathrooms:4
- Half bathrooms:2
- Rooms Total:24
- Flooring:Wood
- Dining Description:Dining Room, Formal/Separate Dining Room
- Bathrooms Description:Bathroom 2, Bathroom 3, Full Bath, Primary Bathroom
- Kitchen Description:2nd Kitchen, Breakfast Area, Built-Ins, Butlers Pantry, Dishwasher, Kitchen - Country, Kitchen - Eat-In, Refrigerator, Stove
- Bedroom Description:Primary Bedroom
- Basement:Yes
- Basement Description:Drainage System, Partial, Poured Concrete, Sump Pump, Unfinished, Workshop
- Living area:9,566 sq. ft.
Heating and cooling
- Cooling:Central A/C, Ductless/Mini-Split, Geothermal
- Heating:Forced Air, Geo-thermal, Oil, Zoned
Structure and exterior
- Roof:Metal
- Year built:1800
- Building area:9,566 sq. ft.
- Lot area:234 Acres
- Lot Features:Fishing Available, Hunting Available, Landscaping, Open, Partly Wooded, Pond, Premium, Private, River, Rural
- Architectural Style:Traditional
- Construction Materials:Brick
- Exterior Features:Boat Storage, Brick, Extensive Hardscape, Exterior Lighting, Kennels, Outbuilding(s), Porch(es), Private Beach, Tennis Court(s)
- Foundation Description:Brick/Mortar
- Levels:3 Story
Utilities
- Water:Well
- Sewer:On Site Septic
Finances and disclosures
- Price:$8,750,000
- Price per sq. ft.:$914.7
- Tax amount:$26,077 (2024)
Features and amenities
- Laundry features:Dryer, Washer
- Amenities:200+ Amp Service, Built-Ins, Exterior Cameras, Phone, Resident Manager
- Pool features:Concrete
New listings near 27295 Southside Island Creek Rd
- New
$1,550,000Active37.86 Acres4502 Old Trappe Rd, TRAPPE, MD 21673
MLS# MDTA2012968Listed by: MEREDITH FINE PROPERTIES - New
$319,000Active4 beds 1 baths1,680 sq. ft.3961 School St, TRAPPE, MD 21673
MLS# MDTA2013124Listed by: COLDWELL BANKER REALTY 
$331,440Pending3 beds 3 baths2,254 sq. ft.1415 Lake Geneva Dr, TRAPPE, MD 21673
MLS# MDTA2013080Listed by: BUILDER SOLUTIONS REALTY- New
$344,440Active3 beds 3 baths2,254 sq. ft.1417 Lake Geneva Dr, TRAPPE, MD 21673
MLS# MDTA2013078Listed by: BUILDER SOLUTIONS REALTY - New
$361,940Active3 beds 3 baths1,600 sq. ft.1686 Lake Placid Dr, TRAPPE, MD 21673
MLS# MDTA2013082Listed by: BUILDER SOLUTIONS REALTY - New
$399,990Active4 beds 4 baths2,170 sq. ft.1233 Lake Meade Dr, TRAPPE, MD 21673
MLS# MDTA2013084Listed by: BUILDER SOLUTIONS REALTY - New
$331,440Active3 beds 3 baths2,254 sq. ft.1423 Lake Geneva Dr, TRAPPE, MD 21673
MLS# MDTA2013068Listed by: BUILDER SOLUTIONS REALTY 
$595,000Pending6 beds 4 baths3860 Main St, TRAPPE, MD 21673
MLS# MDTA2012966Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$1,495,000Active10.88 Acres29569 Porpoise Creek Rd, TRAPPE, MD 21673
MLS# MDTA2012908Listed by: BENSON & MANGOLD, LLC- Open Sun, 3 to 5pm
$599,990Active4 beds 4 baths3,566 sq. ft.1262 Lake Michigan Dr, TRAPPE, MD 21673
MLS# MDTA2012888Listed by: COLDWELL BANKER REALTY
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2023 - 2026 ERA Franchise Systems LLC. All rights reserved. ERA Franchise Systems LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. ERA, ERA Real Estate powered, and their respective logos are registered service marks of ERA Franchise Systems LLC. Each office is independently owned and operated.