#MDGA2008554, Elizabeth S Spiker Holcomb, Listing office: Taylor Made Deep Creek Vacations & Sales
285 Winding Trail Ln Unit 10A Oakland, MD 21550
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
(ACTIVE)
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
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Price information
Property sales
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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
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.
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.
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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.