27295 Southside Island Creek Rd
Trappe, MD 21673

$8,750,000

Price

Beds

Baths

9,566 Sq. Ft.

$915 / Sq. Ft.

9,566

Sq. Ft.

$915

per Sq. Ft.

Virtual Tour

27295 Southside Island Creek Road Trappe, MD 21673 - Photo 1 of 91

a view of a garden with a building in the background

a view of entryway and hall with wooden floor

a view of staircase with railing and a window

a view of a water heater and a floor to ceiling window

a view of entryway with a flower pot and a wooden floor

a living room with furniture and a fireplace

a living room with furniture and wooden floor

a living room with furniture and floor to ceiling windows

a kitchen with stainless steel appliances granite countertop a sink a stove a refrigerator and cabinets

a very nice looking living room with a large window and a book shelf

a living room with furniture and a wooden floor

a bedroom with a bed and a mirror on dresser

a living room with furniture a fireplace and a large window with wooden floor

a living room with furniture and a couch

a bedroom with furniture and a baby crib

a living room with furniture and a floor to ceiling window

a bedroom with furniture and a wooden floor

a view of a garden with an outdoor space

a view of a house with backyard and sitting area

a front view of a house with a yard and garage

a view of a green field with lots of bushes

a view of a terrace with outdoor seating and city view

a view of hall way with furniture and wooden floor

a front view of house with yard and green space

a view of a backyard with a garden and entertaining space

Description

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...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.

Listed by Coard A Benson • Benson & Mangold, LLC
P: (410)-310-4909 coard@coardbenson.com
Listed by Schuyler G. Benson • Benson & Mangold, LLC
P: (410)-822-1415 sbenson@bensonandmangold.com

Property Details for 27295 Southside Island Creek Road

Tax ID Number

2103131645

Ownership

Fee Simple

Condo Coop Association

HOA

Structure Type

Detached

Style

Traditional

Levels/Stories

Furnished

LISTING UPDATED: 01/22/2026 11:39 AM

Property Details for 27295 Southside Island Creek Road

Status	Active
MLS #	MDTA2006798
Days on Market	775
Taxes	$26,077 / year
HOA Fees	-
Condo/Co-op Fees	-
Compass Type	Single Family
MLS Type	Residential / Fee Simple
Year Built	1800
Lot Size	234.00 AC / 10,193,040 SF
County	Talbot County

Location

Compass
MD
Talbot County
Trappe
21673
27295 Southside Island Creek Rd

Listing Courtesy of Benson & Mangold, LLC

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Virtual Tour

Building Information for 27295 Southside Island Creek Road

Stories3Year Built1800Building Size-Lot Size234.00 AC / 10,193,040 SF

Payment Calculator

$44,819 per month

30 year fixed, 6.15% Interest

Principal and Interest

$42,646

Property Taxes

$2,173

HOA Dues

The Payment Calculator is for illustrative purposes only.

Property Information for 27295 Southside Island Creek Road

Location

In City Limits: No
School District Name: TALBOT COUNTY PUBLIC SCHOOLS

School District County ID: 121138072466
SchoolDistrictSource: Listing Agent
County: TALBOT

Waterfront / Water Access

Water View: Yes
Water Access: Yes

Water Access Features: Sail, Canoe/Kayak, Fishing Allowed, Boat - Powered, Personal Watercraft (PWC), Private Access
Water Oriented: Yes
Navigable Water: Yes
Tidal Water: Yes
Water Body Name: Choptank River
Water Body Type: River
Water Frontage In Feet: 3100.0
Riparian Rights Y/N: Yes
Docks Count: 1
Dock Type and Features: Private, Storage Area, Material - Treated Lumber, Hoist/Lift Electric, Pier (Perpendicular)
Dock/Slip Conveys Y/N: true
Dock/Slip Conveyance: Physical Dock/Slip Conveys
Slips Count: 3
Boats Power Count: 2
Boats Nonpower Count: 2
Mean Low Water Feet: 9.00

Association / Community Info

Senior Community: No

Taxes and Assessment

Tax Year: 2024
Tax Assessed Value: $2,887,833

Year Assessed: 2024
County Tax: $26,077
Improvement Assessed Value: $770,300
Land Assessed Value: $2,034,300
Land Use Code: AGRICULTURAL
Agricultural Tax Due: No
Historic: Yes
Zoning: A2
Automatically Update Tax Values Y/N: Yes
TaxDataUpdatedYN: No

Rooms

Main

# Bedrooms Count Main Level: 0
# Bathrooms Count Main Level: 2

# Bathrooms Full Main Level: 0
# Bathrooms Half Main Level: 2

All Upper Levels

# Bedrooms Count All Upper Levels: 6
# Bathrooms Count All Upper Levels: 4

# Bathrooms Full All Upper Levels: 4

Upper Level 1

# Bedrooms Count Upper Level: 3
# Bathrooms Count Upper Level: 3

# Bathrooms Full Upper Level: 3

Upper Level 2

# Bedrooms Count Upper Level: 3
# Bathrooms Count Upper Level: 1

# Bathrooms Full Upper Level: 1

Rooms

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
Stories: Main, Upper 1, Upper 2

Rooms Information

Room 1

Room Type: Foyer
Room Length: 10.0

Room Width: 34.0
Room Level: Main
Room Exists: Yes

Room 2

Room Type: Den
Room Length: 20.0

Room Width: 16.0
Room Level: Main
Room Exists: Yes

Room 3

Room Type: Study
Room Length: 20.0

Room Width: 16.0
Room Level: Main
Room Exists: Yes

Room 4

Room Type: Living Room
Room Length: 21.0

Room Width: 27.0
Room Level: Main
Room Exists: Yes

Room 5

Room Type: Dining Room
Room Length: 12.0

Room Width: 17.0
Room Level: Main
Room Exists: Yes

Room 6

Room Type: Sun/Florida Room
Room Length: 36.0

Room Width: 10.0
Room Level: Main
Room Exists: Yes

Room 7

Room Type: Kitchen
Room Length: 12.0

Room Width: 11.0
Room Level: Main
Room Exists: Yes

Room 8

Room Type: Breakfast Room
Room Length: 12.0

Room Width: 13.0
Room Level: Main
Room Exists: Yes

Room 9

Room Type: Bedroom 2
Room Length: 20.0

Room Width: 16.0
Room Level: Upper 1
Room Exists: Yes

Room 10

Room Type: Bedroom 3
Room Length: 20.0

Room Width: 13.0
Room Level: Upper 1
Room Exists: Yes

Room 11

Room Type: Bathroom 2
Room Length: 10.0

Room Width: 11.0
Room Level: Upper 1
Room Exists: Yes

Room 12

Room Type: Living Room
Room Length: 16.0

Room Width: 18.0
Room Level: Upper 1
Room Exists: Yes

Room 13

Room Type: Kitchen
Room Length: 10.0

Room Width: 10.0
Room Level: Upper 1
Room Exists: Yes

Room 14

Room Type: Primary Bedroom
Room Length: 12.0

Room Width: 18.0
Room Level: Upper 1
Room Exists: Yes

Room 15

Room Type: Primary Bathroom
Room Length: 9.0

Room Width: 9.0
Room Level: Upper 1
Room Exists: Yes

Room 16

Room Type: Bathroom 3
Room Length: 8.0

Room Width: 9.0
Room Level: Upper 1
Room Exists: Yes

Room 17

Room Type: Recreation Room
Room Length: 25.0

Room Width: 35.0
Room Level: Upper 2
Room Exists: Yes

Room 18

Room Type: Bedroom 4
Room Length: 9.0

Room Width: 12.0
Room Level: Upper 2
Room Exists: Yes

Room 19

Room Type: Full Bath
Room Length: 9.0

Room Width: 7.0
Room Level: Upper 2
Room Exists: Yes

Room 20

Room Type: Bedroom 5
Room Length: 16.0

Room Width: 18.0
Room Level: Upper 2
Room Exists: Yes

Room 21

Room Type: Bedroom 6
Room Length: 12.0

Room Width: 18.0
Room Level: Upper 2
Room Exists: Yes

Building Info

Total Finished SQFT: 9,566.00
Total Finished SQFT Source: Assessor

Total SQFT: 9,566.00
Total SQFT Source: Assessor
Main Entrance Orientation: South
Construction Materials: Brick
Roof: Metal
Ext Main Mid-res: http://bright-media02.prd.brightmls.com/bright/images/0000/8027/0008/9312/802700089312_512_384_WM_60YY4IOBlZRsWAf6.jpg
Wall and Ceiling Types: Plaster Walls
Flooring Type: Wood
Basement Type: Drainage System, Partial, Poured Concrete, Sump Pump, Unfinished, Workshop, Other
Foundation Details: Brick/Mortar
Room and Floor: Bathrooms Half-Main Level-1, Bathrooms Half-Main Level-2, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2, Bathrooms Full-Upper Level 1-3, Bedrooms-Upper Level 2-1, Bedrooms-Upper Level 2-2, Bedrooms-Upper Level 2-3, Bathrooms Full-Upper Level 2-1
# Bathrooms Full: 4
# Bathrooms Half: 2
Other Structure: Barn, Bank Barn, Barn/Farm Building, Garage(s), Guest House, Machine Shed, Office/Studio, Poultry House, Shed, Spring House, Utility Building

Lot / Land Information

Lot Size Source: Estimated
Lot Features: Rural, Fishing Available, Hunting Available, Landscaping, Open, Partly Wooded, Pond, Premium, Private

Location Type: River
Parcel ID: 5297334
Additional Parcels: No
Addl Parcels Descrp: Revised offering includes 5 parcels of record with two remaining development rights.
Ground Rent Exists: No

Parking

Type Of Parking: Other

Interior Features

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
Fireplace: Yes

Fireplaces Count: 8
Appliances: Stove, Refrigerator, Dishwasher, Washer, Dryer
Accessibility Features: None
Security Features: Resident Manager, Exterior Cameras
Virtual Tour URL Unbranded: https://my.matterport.com/show/?m=iYdtnVo4ePy&help=1&hl=1&nozoom=1&mls=1

Exterior Features

Spa: No
Exterior Features: Boat Storage, Extensive Hardscape, Exterior Lighting, Kennels, Outbuilding(s), Private Beach, Tennis Court(s), Other

Outdoor Living Structures: Porch(es), Brick
Pool: Yes - Personal
Personal Pool Features: Concrete

Utilities

Utilities: Phone
Heating: Yes

Cooling Type: Geothermal, Central A/C, Ductless/Mini-Split
Cooling Fuel: Geothermal, Electric
Heating Type: Zoned, Forced Air
Heating Fuel: Oil, Geo-thermal
Hot Water: Oil
Water Source: Well
Sewer Septic: On Site Septic
Electric Service: 200+ Amp Service
Internet Services: Cable

Confidential Data

Listing Office

List Agent AOR: Mid-Shore Board of REALTORS
List Agent URL: www.coardbenson.com

Property History for 27295 Southside Island Creek Road

Date	Event & Source	Price	Appreciation
Jun 27, 2025	Price Change BRIGHT #MDTA2006798	$8,750,000	—
Dec 22, 2023	Price Change BRIGHT #MDTA2006798	$8,800,000	—
Dec 22, 2023	Listed (Active) BRIGHT #MDTA2006798	$8,750,000	—

Date	Event & Source	Price
06/27/2025	Price Change BRIGHT #MDTA2006798	$8,750,000
12/22/2023	Price Change BRIGHT #MDTA2006798	$8,800,000
12/22/2023	Listed (Active) BRIGHT #MDTA2006798	$8,750,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Schools near 27295 Southside Island Creek Road

This home is within Talbot County Public Schools.


Rating	School	Type	Grades	Distance
9/10	White Marsh Elementary School	Public - Serves this home	PK to 5	4.1 mi
4/10	Easton Middle School	Public - Serves this home	6 to 8	9.0 mi
5/10	Easton High School	Public - Serves this home	9 to 12	8.8 mi


Rating	School	Distance
9/10	White Marsh Elementary School PublicPK to 5 Serves this home	4.1 mi
4/10	Easton Middle School Public6 to 8 Serves this home	9.0 mi
5/10	Easton High School Public9 to 12 Serves this home	8.8 mi

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 27295 Southside Island Creek Road, Trappe, MD 21673

27295 Southside Island Creek Road is a single family home for sale in Trappe, MD 21673. This property was listed for sale on December 22, 2023 by Benson & Mangold, LLC, it's currently listed at $8,750,000. This listing's school district is Talbot County Public Schools. Nearby schools include White Marsh Elementary School, Easton Middle School and Easton High School. 27295 Southside Island Creek Road is a 6-bed, 6-bath, 9,566 sqft single family home built in 1800.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Benson & Mangold, LLC

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 01/22/2026 11:39 AM

27295 Southside Island Creek RdTrappe, MD 21673

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More information about 27295 Southside Island Creek Road, Trappe, MD 21673

27295 Southside Island Creek Rd
Trappe, MD 21673