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.
For sale
$7,985,000
27295 Southside Island Creek Rd, Trappe, MD 21673
6beds
9,566sqft
Single Family Residence
Built in 1800
234 Acres Lot
$-- Zestimate®
$835/sqft
$-- HOA
What's special
Swimming poolWaterside guest cottageBeach houseAgricultural fieldsMature woodlandsAccessory buildingsHistoric main residence
- 1045 days
- 1,422
- 134
Zillow last checked:
Listing updated:
Listed by:
Coard Benson 410-310-4909,
Benson & Mangold, LLC (410) 770-9255,
Co-Listing Agent: Schuyler G. Benson 410-822-1415,
Benson & Mangold, LLC
Source: Bright MLS,MLS#: MDTA2006798
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 6
- Full bathrooms: 4
- 1/2 bathrooms: 2
- Main level bathrooms: 2
Rooms
- Room types: 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 Bathroom, Full Bath
Primary bedroom
- Level: Upper
- Area: 216 Square Feet
- Dimensions: 18 X 12
Bedroom 2
- Level: Upper
- Area: 320 Square Feet
- Dimensions: 16 X 20
Bedroom 3
- Level: Upper
- Area: 260 Square Feet
- Dimensions: 13 X 20
Bedroom 4
- Level: Upper
- Area: 108 Square Feet
- Dimensions: 12 X 9
Bedroom 5
- Level: Upper
- Area: 288 Square Feet
- Dimensions: 18 X 16
Bedroom 6
- Level: Upper
- Area: 216 Square Feet
- Dimensions: 18 X 12
Primary bathroom
- Level: Upper
- Area: 81 Square Feet
- Dimensions: 9 X 9
Bathroom 2
- Level: Upper
- Area: 110 Square Feet
- Dimensions: 11 X 10
Bathroom 3
- Level: Upper
- Area: 72 Square Feet
- Dimensions: 9 X 8
Breakfast room
- Level: Main
- Area: 156 Square Feet
- Dimensions: 13 X 12
Den
- Level: Main
- Area: 320 Square Feet
- Dimensions: 16 X 20
Dining room
- Level: Main
- Area: 204 Square Feet
- Dimensions: 17 X 12
Foyer
- Level: Main
- Area: 340 Square Feet
- Dimensions: 34 X 10
Other
- Level: Upper
- Area: 63 Square Feet
- Dimensions: 7 X 9
Kitchen
- Level: Main
- Area: 132 Square Feet
- Dimensions: 11 X 12
Kitchen
- Level: Upper
- Area: 100 Square Feet
- Dimensions: 10 X 10
Living room
- Level: Main
- Area: 567 Square Feet
- Dimensions: 27 X 21
Living room
- Level: Upper
- Area: 288 Square Feet
- Dimensions: 18 X 16
Recreation room
- Level: Upper
- Area: 875 Square Feet
- Dimensions: 35 X 25
Study
- Level: Main
- Area: 320 Square Feet
- Dimensions: 16 X 20
Other
- Level: Main
- Area: 360 Square Feet
- Dimensions: 10 X 36
Heating
- Zoned, Forced Air, Oil, Geothermal
Cooling
- Geothermal, Central Air, Ductless, Electric
Appliances
- Included: Cooktop, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
Features
- 2nd Kitchen, Additional Stairway, Breakfast Area, Built-in Features, Butlers Pantry, Floor Plan - Traditional, Formal/Separate Dining Room, Kitchen - Country, Eat-in Kitchen, Plaster Walls
- Flooring: Wood
- Basement: Drainage System,Partial,Concrete,Sump Pump,Unfinished,Workshop,Other
- Number of fireplaces: 8
Interior area
- Total structure area: 9,566
- Total interior livable area: 9,566 sqft
- Finished area above ground: 9,566
- Finished area below ground: 0
Video & virtual tour
Property
Parking
- Parking features: Other
Accessibility
- Accessibility features: None
Features
- Levels: Three
- Stories: 3
- Patio & porch: Porch, Brick
- Exterior features: Boat Storage, Extensive Hardscape, Lighting, Kennel, Private Beach, Tennis Court(s), Other
- Has private pool: Yes
- Pool features: Concrete, Private
- Has view: Yes
- View description: Water, Scenic Vista, River, Pasture, Panoramic, Bay
- Has water view: Yes
- Water view: Water,River,Bay
- Waterfront features: Rip-Rap, Sandy Beach, River, Sail, Canoe/Kayak, Fishing Allowed, Boat - Powered, Personal Watercraft (PWC), Private Access
- Body of water: Choptank River
- Frontage length: Water Frontage Ft: 3100
Lot
- Size: 234 Acres
- Features: Rural, Fishing Available, Hunting Available, Landscaped, Open Lot, Wooded, Pond, Premium, Private
Details
- Additional structures: Above Grade, Below Grade, Outbuilding
- Additional parcels included: Revised offering includes 5 parcels of record with two remaining development rights.
- Parcel number: 2103131645
- Zoning: A2
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Brick
- Foundation: Brick/Mortar
- Roof: Metal
Condition
- Excellent
- New construction: No
- Year built: 1800
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: On Site Septic
- Water: Well
- Utilities for property: Phone, Cable
Community & HOA
Community
- Security: Resident Manager, Exterior Cameras
- Subdivision: Trappe
HOA
- Has HOA: No
Location
- Region: Trappe
Financial & listing details
- Price per square foot: $835/sqft
- Tax assessed value: $2,887,833
- Annual tax amount: $26,077
- Date on market: 12/22/2023
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
Not available
Estimated sales range
Not available
$6,001/mo
Price history
| Date | Event | Price |
|---|---|---|
| 10/26/2026 | Listed for sale | $7,985,000-8.7%$835/sqft |
Source:  Bright MLS #MDTA2006798 Report a problem | ||
| 6/27/2025 | Listed for sale | $8,750,000-0.6%$915/sqft |
Source: Bright MLS #MDTA2006798 Report a problem | ||
| 12/22/2023 | Listed for sale | $8,800,000$920/sqft |
Source: Bright MLS #MDTA2006798 Report a problem | ||
Public tax history
Tax history is unavailable.
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 21673
Nearby schools
Schools provided by the listing agent
- District: Talbot County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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