27295 Southside Island Creek Road

Trappe, MD
$ 8,750,000 Beds 6 Baths 5 Sq 9,566 Virtual Tour
Monthly Estimate* How much can I afford?

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 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 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.

ACTIVE

  • Price
  • $ 8,750,000
  • City
  • Trappe
  • Bedrooms
  • 6
  • Full Bathrooms
  • 4
  • County
  • TALBOT
  • Half Bathrooms
  • 2
  • Area
  • Lot Size
  • 234 Acres
  • Zip
  • 21673
  • Sqr Footage
  • 9,566
  • Year Built
  • 1800
  • Taxes
  • $ 26077
  • Style
  • Traditional
  • MLS#
  • MDTA2006798
Listed By: Coard A Benson with Benson & Mangold, LLC - 4107709255;
Data Source: Bright MLS

Features

General

Living Area 9566
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
Zoning A2
Patio/Porch Features Porch(es),Brick
Architectural Style Traditional
Pool Features Concrete
Security Features Resident Manager,Exterior Cameras
Construction Materials Brick
School District TALBOT COUNTY PUBLIC SCHOOLS
Year Built 1800
Electric 200+ Amp Service
View Water,Scenic Vista,River,Pasture,Panoramic,Bay
Levels 3
Tax Year 2024
Ownership Fee Simple
Cool Fuel Geothermal,Electric
Waterfront Features Rip-Rap,Sandy Beach
Accessibility None
Additional Parcels Description Revised offering includes 5 parcels of record with two remaining development rights.
County TALBOT
New Construction No
Property Type Residential
HOA 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
Full Baths 4
Status ACTIVE
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.
City TRAPPE
Body of Water Choptank River
Disclosures Lead Based Paint - Federal,Historic Property
Senior Community Y/N No
Lot Size Units Square Feet
Lot Size Square Feet 10193040.00
Tax Assessed Value 2887833.0
Tax Annual Amount 26077.0
Home Warranty Y/N No
Property Condition Excellent
Structure Type Detached
Condo/Coop Association fee Y/N No
Bathrooms Count Main Level 2.00
Price Per Sq Ft Total AG 914.7
Additional Parcels Y/N No
Historic Y/N Yes
Lease Considered Y/N No
Vacation Rental Y/N No
Total SQFT 9566
Location Type River
Standard Status Active
Year Built Source Assessor
Legal Subdivision *

Interior Features

Interior Amenities 2nd Kitchen,Additional Stairway,Breakfast Area,Built-Ins,Butlers Pantry,Floor Plan - Traditional,Formal/Separate Dining Room,Kitchen - Country,Kitchen - Eat-In,Wood Floors
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
Half Baths 2
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

Exterior Amenities Boat Storage,Extensive Hardscape,Exterior Lighting,Kennels,Outbuilding(s),Private Beach,Tennis Court(s),Other
Pool Yes - Personal
Lot Features Rural,Fishing Available,Hunting Available,Landscaping,Open,Partly Wooded,Pond,Premium,Private
Water Source Well
Type of Parking Other
Land Use Code AGRICULTURAL
Foundation Details Brick/Mortar
Spa No
Water View Y/N Yes
Lot Size Acres 234.00
Water Body Type River
Lot Size Source Estimated
Waterfront Y/N Yes
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

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 # 2 Upper 1
Kitchen Main
Living Room Main
Living Room # 2 Upper 1
Primary Bathroom Upper 1
Primary Bedroom Upper 1
Recreation Room Upper 2
Study Main
Sun/Florida Room Main

Amenities

  • 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

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Bel Air, MD office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Unknown Elementary School
Middle School Unknown Middle School
High School Unknown High School

Price History

12/22/2023 Listed $8,800,000
6/28/2025 1% - $8,750,000

Property vs Zip Code Average in 21673

Price
AVG $1.68M
$8.75M
Taxes
AVG $7,463
$26,077
Year Built
AVG 1966
1800
Visits
AVG 749
4832
Data Provided by Inside Real Estate®

Areas That We Cover

27295 Southside Island Creek Road Trappe, MD is a Single Family Home for sale at $8750000 with 9566 sqft and a lot size of 234 Acres Acre(s). 27295 Southside Island Creek Road Trappe has 6 bedrooms, 4 baths and was built in 1800. The property's zip code is 21673 which is in Trappe, MD

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.