Search location…
27293 Southside Island Creek Rd photo 1
for saleNew — 1d on market
91 photos
1 / 91
27293 Southside Island Creek Rd photo 2
2 / 91
27293 Southside Island Creek Rd photo 3
3 / 91
27293 Southside Island Creek Rd photo 4
4 / 91
27293 Southside Island Creek Rd photo 5
5 / 91
27293 Southside Island Creek Rd photo 6
6 / 91
27293 Southside Island Creek Rd photo 7
7 / 91
27293 Southside Island Creek Rd photo 8
8 / 91
27293 Southside Island Creek Rd photo 9
9 / 91
27293 Southside Island Creek Rd photo 10
10 / 91
27293 Southside Island Creek Rd photo 11
11 / 91
27293 Southside Island Creek Rd photo 12
12 / 91
27293 Southside Island Creek Rd photo 13
13 / 91
27293 Southside Island Creek Rd photo 14
14 / 91
27293 Southside Island Creek Rd photo 15
15 / 91
27293 Southside Island Creek Rd photo 16
16 / 91
27293 Southside Island Creek Rd photo 17
17 / 91
27293 Southside Island Creek Rd photo 18
18 / 91
27293 Southside Island Creek Rd photo 19
19 / 91
27293 Southside Island Creek Rd photo 20
20 / 91
27293 Southside Island Creek Rd photo 21
21 / 91
27293 Southside Island Creek Rd photo 22
22 / 91
27293 Southside Island Creek Rd photo 23
23 / 91
27293 Southside Island Creek Rd photo 24
24 / 91
27293 Southside Island Creek Rd photo 25
25 / 91
27293 Southside Island Creek Rd photo 26
26 / 91
27293 Southside Island Creek Rd photo 27
27 / 91
27293 Southside Island Creek Rd photo 28
28 / 91
27293 Southside Island Creek Rd photo 29
29 / 91
27293 Southside Island Creek Rd photo 30
30 / 91
27293 Southside Island Creek Rd photo 31
31 / 91
27293 Southside Island Creek Rd photo 32
32 / 91
27293 Southside Island Creek Rd photo 33
33 / 91
27293 Southside Island Creek Rd photo 34
34 / 91
27293 Southside Island Creek Rd photo 35
35 / 91
27293 Southside Island Creek Rd photo 36
36 / 91
27293 Southside Island Creek Rd photo 37
37 / 91
27293 Southside Island Creek Rd photo 38
38 / 91
27293 Southside Island Creek Rd photo 39
39 / 91
27293 Southside Island Creek Rd photo 40
40 / 91
27293 Southside Island Creek Rd photo 41
41 / 91
27293 Southside Island Creek Rd photo 42
42 / 91
27293 Southside Island Creek Rd photo 43
43 / 91
27293 Southside Island Creek Rd photo 44
44 / 91
27293 Southside Island Creek Rd photo 45
45 / 91
27293 Southside Island Creek Rd photo 46
46 / 91
27293 Southside Island Creek Rd photo 47
47 / 91
27293 Southside Island Creek Rd photo 48
48 / 91
27293 Southside Island Creek Rd photo 49
49 / 91
27293 Southside Island Creek Rd photo 50
50 / 91
27293 Southside Island Creek Rd photo 51
51 / 91
27293 Southside Island Creek Rd photo 52
52 / 91
27293 Southside Island Creek Rd photo 53
53 / 91
27293 Southside Island Creek Rd photo 54
54 / 91
27293 Southside Island Creek Rd photo 55
55 / 91
27293 Southside Island Creek Rd photo 56
56 / 91
27293 Southside Island Creek Rd photo 57
57 / 91
27293 Southside Island Creek Rd photo 58
58 / 91
27293 Southside Island Creek Rd photo 59
59 / 91
27293 Southside Island Creek Rd photo 60
60 / 91
27293 Southside Island Creek Rd photo 61
61 / 91
27293 Southside Island Creek Rd photo 62
62 / 91
27293 Southside Island Creek Rd photo 63
63 / 91
27293 Southside Island Creek Rd photo 64
64 / 91
27293 Southside Island Creek Rd photo 65
65 / 91
27293 Southside Island Creek Rd photo 66
66 / 91
27293 Southside Island Creek Rd photo 67
67 / 91
27293 Southside Island Creek Rd photo 68
68 / 91
27293 Southside Island Creek Rd photo 69
69 / 91
27293 Southside Island Creek Rd photo 70
70 / 91
27293 Southside Island Creek Rd photo 71
71 / 91
27293 Southside Island Creek Rd photo 72
72 / 91
27293 Southside Island Creek Rd photo 73
73 / 91
27293 Southside Island Creek Rd photo 74
74 / 91
27293 Southside Island Creek Rd photo 75
75 / 91
27293 Southside Island Creek Rd photo 76
76 / 91
27293 Southside Island Creek Rd photo 77
77 / 91
27293 Southside Island Creek Rd photo 78
78 / 91
27293 Southside Island Creek Rd photo 79
79 / 91
27293 Southside Island Creek Rd photo 80
80 / 91
27293 Southside Island Creek Rd photo 81
81 / 91
27293 Southside Island Creek Rd photo 82
82 / 91
27293 Southside Island Creek Rd photo 83
83 / 91
27293 Southside Island Creek Rd photo 84
84 / 91
27293 Southside Island Creek Rd photo 85
85 / 91
27293 Southside Island Creek Rd photo 86
86 / 91
27293 Southside Island Creek Rd photo 87
87 / 91
27293 Southside Island Creek Rd photo 88
88 / 91
27293 Southside Island Creek Rd photo 89
89 / 91
27293 Southside Island Creek Rd photo 90
90 / 91
27293 Southside Island Creek Rd photo 91
91 / 91

$5,995,000

6beds
|
6baths
|
9,566sqft
|
1800built
27293 Southside Island Creek Rd,Trappe, MD 21673

Est.$39,420/moCustomize payment

What's special

Just listed

On the market for 1 day

$627/sqft

Price per square foot

Built in 1800

226 years old

Overview

Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47b1; 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, ...

Listed by Coard A Benson, Benson & Mangold, LLC

410-310-4909 · coard@coardbenson.com · Office 410-770-9255

Co-listed by Schuyler G. Benson · Benson & Mangold, LLC · 410-822-1415 · sbenson@bensonandmangold.com

MLS #MDTA2013522 · Listed April 23, 2026

Property details

Cost estimate

Est. monthly payment

$35,690/mo
Principal & interest
$31,426
Property tax
$2,266
Home insurance (est.)
$1,998

Down payment

$1,199,00020% of list price
Adjust down payment20%
0%25%50%

Based on 20% down ($1,199,000), 6.85% interest rate, 30-year fixed. Insurance is an estimate. Actual costs may vary.

Rates provided by Mable Loans.

Customize scenario

Price history

DateEventPrice
Apr 23, 2026Listed for sale$5,995,000

Location

27293 Southside Island Creek Rd, Trappe, MD 21673

Nearby homes

$5,995,000

6 beds · 6 baths · 9,566 sqft