Newhouse
1/58
$8,219/mo
$1,250,0004bd·3ba·1,936sf
5480 Windward Drive, Tilghman, MD 21671
Listing Courtesy of Benson & Mangold, LLC
sold
83 photos
1 / 83
2 / 83
3 / 83
4 / 83
5 / 83
6 / 83
7 / 83
8 / 83
9 / 83
10 / 83
11 / 83
12 / 83
13 / 83
14 / 83
15 / 83
16 / 83
17 / 83
18 / 83
19 / 83
20 / 83
21 / 83
22 / 83
23 / 83
24 / 83
25 / 83
26 / 83
27 / 83
28 / 83
29 / 83
30 / 83
31 / 83
32 / 83
33 / 83
34 / 83
35 / 83
36 / 83
37 / 83
38 / 83
39 / 83
40 / 83
41 / 83
42 / 83
43 / 83
44 / 83
45 / 83
46 / 83
47 / 83
48 / 83
49 / 83
50 / 83
51 / 83
52 / 83
53 / 83
54 / 83
55 / 83
56 / 83
57 / 83
58 / 83
59 / 83
60 / 83
61 / 83
62 / 83
63 / 83
64 / 83
65 / 83
66 / 83
67 / 83
68 / 83
69 / 83
70 / 83
71 / 83
72 / 83
73 / 83
74 / 83
75 / 83
76 / 83
77 / 83
78 / 83
79 / 83
80 / 83
81 / 83
82 / 83
83 / 83
$1,000,000
Sold5beds
|3baths
|4,214sqft
|2005built
5520 Leeward Lane,Tilghman, MD 21671
Sold onJune 18, 2026· Listed at $1,100,000
This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.
Overview
Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a spacious main-level layout designed to impress. The expansive living room is flooded with natural light and flanked by a formal dining area, a warm and inviting den, and a breakfast nook with vaulted ...
Listing updated: June 18, 2026 at 8:25 PM
Listed by:
Samantha Kay Jackson (484) 889-9364, Keller Williams Realty
Source: Bright MLS · MLS #MDTA2010832
Property details
Price history
| Date | Event | Price |
|---|---|---|
| Jun 18, 2026 | Sold | $1,000,000 |
| May 27, 2025 | Listed for sale | $1,100,000 |
Location
5520 Leeward Lane, Tilghman, MD 21671
Get matched
Looking for something like this?
Tell us what you're looking for and we'll send fresh matches near Tilghman the moment they list.
Find homes like thisFree, takes about a minute
Recently sold nearby
Similar homes sold within 0.5 miles in the last 90 days.
This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.
Homes for sale near here
Active listings within ~5 miles of this address.
