Listing provided courtesy of Benson & Mangold, LLC- MLS# MDTA2013522
Contact Information: [email protected] - 4107709255
Contact Information: [email protected] - 4107709255Images
Request Info27293 SOUTHSIDE ISLAND CREEK ROADTRAPPE, MD 21673
Single Family · 6 Beds · 4 Full Baths · 2 Half Baths · 9,566 Sq. ft. | 47.99 Acres$5,995,000
ACTIVE
27293 SOUTHSIDE ISLAND CREEK ROAD Overview
- Time on Site:
- 67 days
- Visits:
- 4
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. 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 was at one time, 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.
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27293 SOUTHSIDE ISLAND CREEK ROAD Facts & Features
- Type Single Family
- Sq. ft. 9,566
- Price/Sq.ft. $627
- Lot 47.99 Acres
Details
General
Association/HOA
- Association: No
- Condo/Coop Association: No
Listing Information
- Real Estate Owned: No
- Short Sale: No
Building Information
- New Construction: No
- Pool: Yes - Personal
- Total SQFT: 9566
- Year Built: 1800
Location/Region
- Country: US
- County: TALBOT
- County Or Parish: TALBOT
- In City Limits: No
- Subdivision Name: TRAPPE
Parking Information
- Type of Parking: Other
Rent/Lease Information
- Lease Considered: No
Tax Information
- Tax Annual Amount: $27,191.00
- Tax Assessed Value: 3054300.00
- Tax Year: 2026
General Information
- Furnished: No
- Property Condition: Excellent
- Property Type: Residential
- School District Name: TALBOT COUNTY PUBLIC SCHOOLS
- Senior Community: No
- Special Listing Conditions: Standard
- Vacation Rental: No
- Zoning: A-2 / RC
Interior
Building Information
- Building Winterized: No
- Cooling Fuel: Geothermal,Electric
- Heating Fuel: Oil,Geo-thermal
Parking Information
- Garage: No
Beds/Baths
- Bathrooms Full: 4
- Bathrooms Full Main Level: 0
- Bathrooms Half: 2
- Bathrooms Half Main Level: 2
- Bathrooms Total: 6
- Bedrooms Total: 6
Building Exterior/Construction
- Structure Type: Detached
- Wall & Ceiling Types: Plaster Walls
Building Interior
- Above Grade Finished Area: 9566
- Above Grade Finished Area Source: Assessor
- Above Grade Finished Area Units: Square Feet
- Below Grade Finished Area: 0
- Below Grade Finished Area Source: Assessor
- Below Grade Finished Area Units: Square Feet
- Central Air: Yes
- Hot Water: Oil
General Information
- Accessibility Features: None
- Appliances: Stove, Refrigerator, Dishwasher, Washer, Dryer
- Cooling: Geothermal, Central A/C, Ductless/Mini-Split
- Electric: 200+ Amp Service
- Fireplace: Yes
- Fireplaces Total: 8
- Flooring: Wood
- Foundation Details: Brick/Mortar
- 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
- Internet Services: Cable,Fiber Optic
- Levels: 3
- Living Area: 9566
- Living Area Source: Assessor
- Main Level Bathrooms: 2.00
- Main Level Bedrooms: 0
- Rooms Total: 24
- Security Features: Resident Manager,Exterior Cameras
- Spa: No
Room Information
- Room List: 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
Exterior
Lot Information
- Additional Parcels: No
- Lot Features: Rural, Fishing Available, Landscaping, Open, Premium, Private
- Lot Size Acres: 47.99
- Lot Size Source: Estimated
- Lot Size Square Feet: 2090444.00
- Lot Size Units: Square Feet
- Water Source: Well
Waterfront/View
- View: Water, Scenic Vista, River, Pasture, Panoramic, Bay
- Water Body Name: Choptank River
- Water Body Type: River
- Water Oriented: Yes
- Water View: Yes
- Waterfront Features: Sandy Beach
- Waterfront: Yes
Building Exterior/Construction
- Architectural Style: Traditional
- Construction Materials: Brick
- Direction Faces: South
- Dock Type and Features: Pier (Perpendicular)
- Docks Count: 1
- Patio And Porch Features: Porch(es), Brick
- Roof: Metal
General Information
- Exterior Features: Boat Storage, Extensive Hardscape, Exterior Lighting, Kennels, Outbuilding(s), Private Beach, Tennis Court(s), Other
- Other Structures: Above Grade,Below Grade
- Pool Features: Concrete
- Sewer: On Site Septic
- Utilities: Phone
- Water Access Features: Private Beach
- Water Access: Yes
Room Information
Room: Breakfast Room
- Level: Main
- Length: 12
- Width: 13
Room: Den
- Level: Main
- Length: 20
- Width: 16
Room: Dining Room
- Level: Main
- Length: 12
- Width: 17
Room: Foyer
- Level: Main
- Length: 10
- Width: 34
Room: Kitchen
- Level: Main
- Length: 12
- Width: 11
Room: Living Room
- Level: Main
- Length: 21
- Width: 27
Room: Study
- Level: Main
- Length: 20
- Width: 16
Room: Sun/Florida Room
- Level: Main
- Length: 36
- Width: 10
Room: Bathroom 2
- Level: Upper 1
- Length: 10
- Width: 11
Room: Bathroom 3
- Level: Upper 1
- Length: 8
- Width: 9
Room: Bedroom 2
- Level: Upper 1
- Length: 20
- Width: 16
Room: Bedroom 3
- Level: Upper 1
- Length: 20
- Width: 13
Room: Kitchen
- Level: Upper 1
- Length: 10
- Width: 10
Room: Living Room
- Level: Upper 1
- Length: 16
- Width: 18
Room: Primary Bathroom
- Level: Upper 1
- Length: 9
- Width: 9
Room: Primary Bedroom
- Level: Upper 1
- Length: 12
- Width: 18
Room: Bedroom 4
- Level: Upper 2
- Length: 9
- Width: 12
Room: Bedroom 5
- Level: Upper 2
- Length: 16
- Width: 18
Room: Bedroom 6
- Level: Upper 2
- Length: 12
- Width: 18
Room: Full Bath
- Level: Upper 2
- Length: 9
- Width: 7
Room: Recreation Room
- Level: Upper 2
- Length: 25
- Width: 35
27293 SOUTHSIDE ISLAND CREEK ROAD Neighborhood
Community
21673 (TRAPPE) Demographics
49
Median Age
44
Population Density (per sq. mile)
43%
College Educated
$71,723
Estimated Median Income
1,019
Estimated Total Home Owners
318
Estimated Total Renters
76% / 24%
Estimated Owner / Renter Divide
2
Estimated Average Household Size
Schools
School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.27293 SOUTHSIDE ISLAND CREEK ROAD Monthly Cost
27293 SOUTHSIDE ISLAND CREEK ROAD Market Data
Based on the last 30 days in this zip code
$1,185,529
Average List Price
$392
Average Price per Square Foot
2
Properties Sold
130
Average Days on Market
35
Properties for Sale
27293 SOUTHSIDE ISLAND CREEK ROAD History
| Date | Value | Agent |
|---|---|---|
| 4/23/2026Source: BRIGHT MLS | April 23, 2026 |