1 day on Rocket
$6,994 Closing Credit¹
#MDGA2009744, Michael N Kennedy, Listing office: Railey Realty, Inc.
$598,000 List price
258 Winding Trail Ln Unit 8B Oakland, MD 21550
$7,101
Closing credit¹
5 beds
4 full, 1 partial
3,300 sqft
$181 / sqft
Townhouse
Property details
About 258 Winding Trail Ln Unit 8B
258 Winding Trail Lane is a luxurious duplex home located in the serene yet convenient community of Timberlake Village. The home feels warm and inviting from the moment you enter. Offering 3,300 SF with an open floorplan, three levels of living space, a large kitchen with granite countertops, two stone propane fireplaces, and LVF on the main and lower levels. This home boasts many recent upgrades, including a tankless water heater and a new washer and dryer. The location feels very private, and the wooded setting makes for an ideal backdrop to this great property. Step outside to enjoy a nice covered deck, fenced in backyard, hot tub and a firepit. If you are looking for a home that checks off all the boxes to enjoy family and friends with plenty of space, this is it. You are also just minutes to Wisp Ski Resort and Deep Creek Lake. Established rental *Wright off the Lake".
Highlights
Home typeTownhouse
HeatingForced Air
StatusAccepting Backup Offers
(ACTIVE UNDER CONTRACT)
(ACTIVE UNDER CONTRACT)
CoolingCentral Air
Size3,300 sqft
BasementYes
Year built2009
ParkingDriveway
MLS #MDGA2008966
FireplaceStone
ViewMountain(s), Trees/Woods
Summary
- Partial Bathrooms: 1
- Full Bathrooms: 4
- Appliances: Microwave, Dishwasher, Dryer, Oven, Electric Range, Refrigerator, Washer
- Basement: Yes
- Flooring Type: Carpet, Hardwood
- Interior: Dining Area, Entry Level Bedroom, Floor Plan - Open, Wood Floors
- Fireplace: Stone
- Total Bedroom Count: 5
- Parking: Driveway
- View: Mountain(s), Trees/Woods
- Exterior: Hot Tub
- Architectural Style: Contemporary
- Heating: Forced Air
- Cooling: Central Air
- List Price: $598,000
- Price/SqFt: $181
- Lot: Trees
- Directions: Garrett Highway South to left on Glendale Road, right on Zeddock Miller, right into Timberlake.
- Year Built: 2009
- Stories: 3
- Living Area: 3,300 SqFt
- MLS Number: MDGA2008966
- MLS Name: BRIGHT
- Office Name: Taylor Made Deep Creek Vacations & Sales
- Office Phone: (301) 387-4700
- Listing Agent: Elizabeth S Spiker Holcomb
- Agent Phone: (301) 616-5022
- Agent Email: betsy@deepcreeksales.com
Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which participates, and is provided by BRIGHT through a licensing agreement.
The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. 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. ©2025 BrightMLS. All rights reserved.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 6/13/2025, 8:45:37 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
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$598,000
258 Winding Trail Ln Unit 8B
$7,101
closing credit¹
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Price information
Property sales
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Tax history
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Nearby schools
5
Broad Ford Elementary School
Public District PK-5
6.4 mi
•607 Harvey Winters Dr
6
Yough Glades Elementary School
Public District PK-5
7.9 mi
•70 Wolf Acres Dr
8
Accident Elementary School
Public District PK-5
8.9 mi
•534 Accident Bittinger Rd
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $53,750. Most Oakland, MD residents have annual incomes less than $<35k. Typical family type is married, no kids. The majority of residents in this area have post secondary degree education.
How much money do the neighbors make?
37%
<35k
36%
35k-100k
25%
100k-200k
2%
200k+
What level of education do the neighbors have?
High School Diploma
Post Secondary Degree
Masters Degree
Doctorate
What types of families live nearby?
40%
Single, No Kids
4%
Single, with Kids
41%
Married, No Kids
15%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
9%
<11 yrs old
8%
12-17 yrs old
11%
18-34 yrs old
49%
35-64 yrs old
23%
65+ yrs old
What do the neighbors do for fun?
Hunting
Figure Skating
NASCAR
Where do the neighbors shop?
Dillards
Dollar General
Dick's Sporting Goods
Where do the neighbors go to eat?
Cracker Barrel
Applebees
Texas Roadhouse
What do the neighbors drive?
Cadillac
Subaru
Ram
What do the neighbors listen to?
News/Talk/Information
Classic Country
New Country
All data provided by Home Junction and Claritas
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Frequently asked questions
About 258 Winding Trail Ln Unit 8B
The listing price of 258 Winding Trail Ln Unit 8B property is $598,000.
The property 258 Winding Trail Ln Unit 8B is a townhouse located in Oakland, Maryland, 21550.
Accepting Backup Offers: 258 Winding Trail Ln Unit 8B is Accepting Backup Offers (Active Under Contract), there is still a chance to have your real estate agent submit an offer.
The nearby schools for 258 Winding Trail Ln Unit 8B are: Broad Ford Elementary School (GreatSchools Rating 5/10), Yough Glades Elementary School (GreatSchools Rating 6/10), Accident Elementary School (GreatSchools Rating 8/10), Southern Middle School (GreatSchools Rating 4/10), Northern Middle School (GreatSchools Rating 9/10), Terra Alta/East Preston School (GreatSchools Rating 5/10), Southern Garrett High School (GreatSchools Rating 5/10), Northern Garrett High School (GreatSchools Rating 8/10), Union Educational Complex (GreatSchools Rating 3/10).
The property at 258 Winding Trail Ln Unit 8B has 5 bedrooms and 4 full and 1 half bathrooms.
The property 258 Winding Trail Ln Unit 8B is 3,300 SqFt (source: MLS/tax record).
The year of construction for 258 Winding Trail Ln Unit 8B is 2009.
This home is located at 258 Winding Trail Ln Unit 8B in Oakland, MD and zip code 21550. This 3,300 square foot home was built in 2009. Features: 5 bedrooms, 5 bathrooms. It has been listed on Rocket Homes since February 27, 2025 and is currently priced at $598,000.
Between April and May 2025, Oakland, MD real estate market has seen increase in the number of listings by 41.9%. In May 2025, listings were on the market for 111 days. During the same period, the median list price in this real estate market was $485,500.
From Rocket Homes Real Estate and based on county public records data.