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
$7,985,000
- 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:$7,985,000
- Price per sq. ft.:$834.73
About this home
The Wilderness presents an extraordinary opportunity to acquire 234± acres across five recorded parcels in Trappe, Maryland, including three waterfront parcels along the Choptank River and two inland parcels. With over 3,000 feet of combined shoreline, broad southerly views, deep water, agricultural fields, and mature woodlands, this significant Eastern Shore estate offers remarkable privacy, history, and recreational opportunities. Two additional residential development rights, each associated with a separate recorded parcel, are subject to building size limitations, applicable land-use regulations, and required approvals. Convenient to Oxford, Easton, Cambridge, and St. Michaels.
The land is among the property's most compelling features. One inland parcel comprises approximately 52 wooded acres offering excellent deer and turkey. A tidal pond, waterfront habitat, and surrounding farmland provide further opportunities for waterfowl and upland game. The diverse landscape supports outdoor recreation, sporting pursuits, and continued agricultural use.
Set among distinguished waterfront estates and majestic specimen trees, the improvements include a historic main residence, waterside guest cottage, beach house, pool house, swimming pool, private pier, tennis court, early 20th-century barn, and accessory buildings. Across the four residential structures are a combined 12 bedrooms, 9 full bathrooms, and 3 half bathrooms, providing exceptional accommodations for family and guests.
The main house is the former home of Daniel Martin, Maryland's 20th Governor, who served in 1829 and 1831. Martin, the grandson of an earlier owner, constructed the larger Federal-style wing around 1815. Listed on the National Register of Historic Places in 1974, The Wilderness is recognized for its significance in Maryland's domestic architecture. The original brick wing dates to the late 18th century, with an early 19th-century addition distinguished by unusual telescoping architecture that increases in scale. White brick, and olive-green shutters and trim complement the mature grounds and an immense sycamore.
A long gravel drive beneath a canopy of trees passes the barn and outbuildings before reaching the residence. Inside, an elegant foyer and stair hall feature an elliptical arch, while a rear French door frames views of the lawn and Choptank River. Two gracious parlors have period fireplace mantels historically attributed to English artisans Grinling Gibbons and Robert Adam.
The main level includes a living room, dining room, original and additional kitchens, pantry, two powder rooms, and a sunroom opening to a riverside terrace. Upstairs are bedrooms with fireplaces and walk-in closets, an artist's studio with cabinetry and sink, and a primary suite with river views, fireplace, and two bathrooms. The attic level includes additional bedrooms and a spacious game room. The main residence totals 6 bedrooms, 5 full bathrooms, and 2 half bathrooms.
Additional accommodations include a waterside guest cottage with 2 bedrooms and 1 full bath; a beach house with 3 bedrooms, 2 full baths, and 1 half bath; and a pool house with 1 bedroom and 1 full bath.
With its combination of historic architecture, extensive shoreline, wooded hunting grounds, farmland, multiple residences, and recreational amenities, The Wilderness offers an exceptional opportunity for long-term stewardship of a remarkable Eastern Shore estate. Explore the virtual tour to appreciate the full scope of this offering....
Contact an agent
Home facts
- Year built:1800
- Subdivision & Development:TRAPPE
- Listing ID #:MDTA2006798
- Added:1042 day(s) ago
- Updated:October 30, 2026 at 02:35 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:$7,985,000
- Price per sq. ft.:$834.73
- 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
- Coming Soon
$289,900Coming Soon3 beds 2 baths1,120 sq. ft.3967 Harrison Cir, TRAPPE, MD 21673
MLS# MDTA2015292Listed by: LPT REALTY, LLC - Coming Soon
$470,000Coming Soon3 beds 3 baths2,184 sq. ft.5935 Bay Acres Dr, TRAPPE, MD 21673
MLS# MDTA2014976Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY 
$100,000Pending2 beds 1 baths1,380 sq. ft.31321 Bruceville Rd, TRAPPE, MD 21673
MLS# MDTA2015484Listed by: MEREDITH FINE PROPERTIES- New
$478,940Active4 beds 3 baths2,340 sq. ft.285 Silver Lake Ln, TRAPPE, MD 21673
MLS# MDTA2015468Listed by: BROOKFIELD MID-ATLANTIC BROKERAGE, LLC 
$349,900Active3 beds 2 baths1,008 sq. ft.4072 Main St, TRAPPE, MD 21673
MLS# MDTA2015374Listed by: BENSON & MANGOLD, LLC
$527,415Pending4 beds 4 baths2,340 sq. ft.1955 Silver Lake Ln, TRAPPE, MD 21673
MLS# MDTA2013576Listed by: BROOKFIELD MID-ATLANTIC BROKERAGE, LLC
$225,000Pending3 beds 2 baths1,472 sq. ft.3908 Harrison Cir, TRAPPE, MD 21673
MLS# MDTA2015230Listed by: MEREDITH FINE PROPERTIES
$450,999Active3 beds 2 baths1,734 sq. ft.1258 Lake Michigan Dr, TRAPPE, MD 21673
MLS# MDTA2015160Listed by: BERKSHIRE HATHAWAY HOMESERVICES HOMESALE REALTY
$235,000Active3 beds 2 baths1,292 sq. ft.29499 Laurwayn Dr, TRAPPE, MD 21673
MLS# MDTA2015202Listed by: LONG & FOSTER REAL ESTATE, INC.
$879,000Pending4 beds 3 baths3,839 sq. ft.29629 Ferry Point Dr, TRAPPE, MD 21673
MLS# MDTA2014994Listed by: MEREDITH FINE PROPERTIES
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.