Search location…
178 Winding Trail Ln # 5b photo 1
for sale
47 photos
1 / 47
178 Winding Trail Ln # 5b photo 2
2 / 47
178 Winding Trail Ln # 5b photo 3
3 / 47
178 Winding Trail Ln # 5b photo 4
4 / 47
178 Winding Trail Ln # 5b photo 5
5 / 47
178 Winding Trail Ln # 5b photo 6
6 / 47
178 Winding Trail Ln # 5b photo 7
7 / 47
178 Winding Trail Ln # 5b photo 8
8 / 47
178 Winding Trail Ln # 5b photo 9
9 / 47
178 Winding Trail Ln # 5b photo 10
10 / 47
178 Winding Trail Ln # 5b photo 11
11 / 47
178 Winding Trail Ln # 5b photo 12
12 / 47
178 Winding Trail Ln # 5b photo 13
13 / 47
178 Winding Trail Ln # 5b photo 14
14 / 47
178 Winding Trail Ln # 5b photo 15
15 / 47
178 Winding Trail Ln # 5b photo 16
16 / 47
178 Winding Trail Ln # 5b photo 17
17 / 47
178 Winding Trail Ln # 5b photo 18
18 / 47
178 Winding Trail Ln # 5b photo 19
19 / 47
178 Winding Trail Ln # 5b photo 20
20 / 47
178 Winding Trail Ln # 5b photo 21
21 / 47
178 Winding Trail Ln # 5b photo 22
22 / 47
178 Winding Trail Ln # 5b photo 23
23 / 47
178 Winding Trail Ln # 5b photo 24
24 / 47
178 Winding Trail Ln # 5b photo 25
25 / 47
178 Winding Trail Ln # 5b photo 26
26 / 47
178 Winding Trail Ln # 5b photo 27
27 / 47
178 Winding Trail Ln # 5b photo 28
28 / 47
178 Winding Trail Ln # 5b photo 29
29 / 47
178 Winding Trail Ln # 5b photo 30
30 / 47
178 Winding Trail Ln # 5b photo 31
31 / 47
178 Winding Trail Ln # 5b photo 32
32 / 47
178 Winding Trail Ln # 5b photo 33
33 / 47
178 Winding Trail Ln # 5b photo 34
34 / 47
178 Winding Trail Ln # 5b photo 35
35 / 47
178 Winding Trail Ln # 5b photo 36
36 / 47
178 Winding Trail Ln # 5b photo 37
37 / 47
178 Winding Trail Ln # 5b photo 38
38 / 47
178 Winding Trail Ln # 5b photo 39
39 / 47
178 Winding Trail Ln # 5b photo 40
40 / 47
178 Winding Trail Ln # 5b photo 41
41 / 47
178 Winding Trail Ln # 5b photo 42
42 / 47
178 Winding Trail Ln # 5b photo 43
43 / 47
178 Winding Trail Ln # 5b photo 44
44 / 47
178 Winding Trail Ln # 5b photo 45
45 / 47
178 Winding Trail Ln # 5b photo 46
46 / 47
178 Winding Trail Ln # 5b photo 47
47 / 47

$589,000

5beds
|
5baths
|
3,300sqft
|
2006built
178 Winding Trail Ln # 5b,Oakland, MD 21550

Est.$3,873/moCustomize payment

What's special

$178/sqft

Price per square foot

Built in 2006

20 years old

1 parking spaces

Garage

Overview

Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lake has to offer, Whispering Pines is the ultimate turnkey mountain retreat. This impeccably maintained 5-bedroom townhome spans three levels of inviting living space and features an attached garage - perfect for hosting family, friends, or guests year-round. Enjoy the best of both worlds: a private, serene atmosphere with the ease of low-maintenance living and a welcoming community feel through the HOA. Already an established and successful vacation rental, this property is truly ready to enjoy or generate...

Listed on January 8, 2026 · Source: MLS #MDGA2010960

Property details

Cost estimate

Est. monthly payment

$4,212/mo
Principal & interest
$3,088
Property tax
$528
Home insurance (est.)
$196
HOA fee
$400

Down payment

$117,80020% of list price
Adjust down payment20%
0%25%50%

Based on 20% down ($117,800), 6.85% interest rate, 30-year fixed. Insurance is an estimate. Actual costs may vary.

Customize scenario

Price history

DateEventPrice
Jan 8, 2026Listed for sale$589,000

Location

178 Winding Trail Ln # 5b, Oakland, MD 21550

Nearby homes

$589,000

5 beds · 5 baths · 3,300 sqft