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$589,000

285 Winding Trail Ln Unit 10A Oakland, MD 21550

5 beds
4 full, 1 partial
3,300 sqft
$178 / sqft
Townhouse

Property details

About 285 Winding Trail Ln Unit 10A

Welcome to this stunning 5-bedroom, 4.5-bathroom duplex-style home at Deep Creek Lake, offering the perfect blend of mountain charm, modern finishes, and exceptional rental potential. This meticulously maintained retreat spans three finished levels and boasts a spacious, professionally designed lower-level patio featuring a cozy fire pit, relaxing mountain views, and a brand-new 2024 hot tub—perfect for entertaining or unwinding after a day on the slopes or lake. Inside, the main level showcases an open-concept kitchen with granite countertops, stainless steel appliances, and a rustic shiplap accent wall that adds warmth and character. The inviting living area features a gas fireplace and access to a covered deck—ideal for enjoying all-season outdoor living. The home offers three bedroom suites, each with private bathrooms featuring tile-accented tub/shower combos, offering comfort and privacy for guests or family members. The fully finished lower level includes a large recreation room with a pool table, wet bar, and easy access to the outdoor patio space. A thoughtfully modified garage space includes an owner’s storage area and a main level laundry room for added convenience. Located just minutes from Deep Creek Lake State Park, Wisp Resort, marinas, restaurants, and area attractions, this home is ideally situated for four-season fun. Currently operating as a high-performing Airbnb rental, this property generated over $50,000 in income last year with strong occupancy and room to grow! Whether you're seeking a private getaway, an income-producing investment, or both—this Deep Creek gem checks all the boxes. Don't miss your chance to own a piece of the lake life!

Highlights

Home typeTownhouse
HeatingForced Air
StatusActive
(ACTIVE)
CoolingCentral Air, Ceiling Fan(s)
Size3,300 sqft
BasementYes
Year built2008
ParkingAssigned,Paved Driveway, Driveway
MLS #MDGA2009744
ViewMountain(s)

Summary

  • Partial Bathrooms: 1
  • Full Bathrooms: 4
  • Appliances: Microwave, Dishwasher, Disposal, Dryer, Oven, Electric Range, Refrigerator, Stainless Steel Appliances, Washer
  • Basement: Yes
  • Flooring Type: Ceramic Tile, Hardwood, Carpet
  • Interior: Bar, Bathroom - Tub Shower, Carpet, Ceiling Fan(s), Combination Dining/Living, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Open, Primary Bath(s), Recessed Lighting, Upgraded Countertops, Walk-in Closet(s), WhirlPool/HotTub, Wood Floors
  • Total Bedroom Count: 5
  • Parking: Assigned,Paved Driveway, Driveway
  • View: Mountain(s)
  • Exterior: Extensive Hardscape, Hot Tub
  • Architectural Style: Villa
  • Heating: Forced Air
  • Cooling: Central Air, Ceiling Fan(s)
  • List Price: $589,000
  • Price/SqFt: $178
  • Lot: Trees, Landscaped
  • Directions: Rt. 219 to Glendale Road. Turn right onto Zeddock Miller Road. Turn right into Timberlake Village. Follow Winding Trail Lane up hill and unit will be on the left.
  • Year Built: 2008
  • Stories: 3
  • Living Area: 3,300 SqFt
  • MLS Number: MDGA2009744
  • MLS Name: BRIGHT
  • Office Name: Railey Realty, Inc.
  • Office Phone: (301) 387-2000
  • Listing Agent: Michael N Kennedy
  • Agent Phone: (301) 616-6106
  • Agent Email: mkennedy@railey.com

IDX 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: 7/10/2025, 10:45:34 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.

Price information

Property sales

We're sorry, we currently don't have property sales data for this listing.

Tax history

We're sorry, we currently don't have tax history data for this listing.

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

8.0 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.

All data from GreatSchools

Neighborhood

The neighbors living near this home have an average income of $53,750. Residents of Oakland, MD typically earn less than $<35k each year. Most families are married, no kids. The most common level of education of people living in this area is post secondary degree.

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?

  • HuntingHunting
  • Figure SkatingFigure Skating
  • NASCARNASCAR

Where do the neighbors shop?

  • DillardsDillards
  • Dollar GeneralDollar General
  • Dick's Sporting GoodsDick's Sporting Goods

Where do the neighbors go to eat?

  • Cracker BarrelCracker Barrel
  • ApplebeesApplebees
  • Texas RoadhouseTexas Roadhouse

What do the neighbors drive?

  • CadillacCadillac
  • SubaruSubaru
  • RamRam

What do the neighbors listen to?

  • News/Talk/InformationNews/Talk/Information
  • Classic CountryClassic Country
  • New CountryNew Country
All data provided by Home Junction and Claritas

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Frequently asked questions

About 285 Winding Trail Ln Unit 10A

The listing price of 285 Winding Trail Ln Unit 10A property is $589,000.

The property 285 Winding Trail Ln Unit 10A is a townhouse located in Oakland, Maryland, 21550.

Active Listing: 285 Winding Trail Ln Unit 10A is For Sale (Active/New) which means the seller is accepting offers.

The nearby schools for 285 Winding Trail Ln Unit 10A 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 285 Winding Trail Ln Unit 10A has 5 bedrooms and 4 full and 1 half bathrooms.

The property 285 Winding Trail Ln Unit 10A is 3,300 SqFt (source: MLS/tax record).

The year of construction for 285 Winding Trail Ln Unit 10A is 2008.

This home is located at 285 Winding Trail Ln Unit 10A in Oakland, MD and zip code 21550. This 3,300 square foot home was built in 2008. Features: 5 bedrooms, 5 bathrooms. It has been listed on Rocket Homes since June 11, 2025 and is currently priced at $589,000.

The number of homes for sale in Oakland, MD increased by 32.7% between May and June 2025. In June 2025, listings were on the market for 106 days. During the same period, the median list price in this real estate market was $475,000.

From Rocket Homes Real Estate and based on county public records data.

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