house
1/55
$55,233/mo
$8,400,0003bd·2ba·1,966sf
3750 Windy Hill Rd, Trappe, MD 21673
Listing Courtesy of VYBE Realty
for sale
91 photos
1 / 91
2 / 91
3 / 91
4 / 91
5 / 91
6 / 91
7 / 91
8 / 91
9 / 91
10 / 91
11 / 91
12 / 91
13 / 91
14 / 91
15 / 91
16 / 91
17 / 91
18 / 91
19 / 91
20 / 91
21 / 91
22 / 91
23 / 91
24 / 91
25 / 91
26 / 91
27 / 91
28 / 91
29 / 91
30 / 91
31 / 91
32 / 91
33 / 91
34 / 91
35 / 91
36 / 91
37 / 91
38 / 91
39 / 91
40 / 91
41 / 91
42 / 91
43 / 91
44 / 91
45 / 91
46 / 91
47 / 91
48 / 91
49 / 91
50 / 91
51 / 91
52 / 91
53 / 91
54 / 91
55 / 91
56 / 91
57 / 91
58 / 91
59 / 91
60 / 91
61 / 91
62 / 91
63 / 91
64 / 91
65 / 91
66 / 91
67 / 91
68 / 91
69 / 91
70 / 91
71 / 91
72 / 91
73 / 91
74 / 91
75 / 91
76 / 91
77 / 91
78 / 91
79 / 91
80 / 91
81 / 91
82 / 91
83 / 91
84 / 91
85 / 91
86 / 91
87 / 91
88 / 91
89 / 91
90 / 91
91 / 91
$8,750,000
6beds
|6baths
|9,566sqft
|1800built
27295 Southside Island Creek Rd,Trappe, MD 21673
Est.$57,535/moCustomize payment
What's special
$915/sqft
Price per square foot
Built in 1800
226 years old
Overview
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 ...
Listing updated: June 2, 2026 at 9:00 AM
Listed by:
Coard A Benson 410-310-4909, Benson & Mangold, LLC, Co-Listing Agent: Schuyler G. Benson 410-822-1415, Benson & Mangold, LLC
Source: Bright MLS · MLS #MDTA2006798
Property details
Cost estimate
Est. monthly payment
$50,958/mo
Principal & interest
$45,868Property tax
$2,173Home insurance (est.)
$2,917Down payment
$1,750,00020% of list price
Adjust down payment20%
0%25%50%
Based on 20% down ($1,750,000), 6.85% interest rate, 30-year fixed. Insurance is an estimate. Actual costs may vary.
Rates provided by Mable Loans.
Price history
| Date | Event | Price |
|---|---|---|
| Dec 22, 2023 | Listed for sale | $8,750,000 |
Location
27295 Southside Island Creek Rd, Trappe, MD 21673