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!
For sale
$589,000
285 Winding Trail Ln UNIT 10A, Oakland, MD 21550
5beds
3,300sqft
Est.:
Condominium
Built in 2008
-- sqft lot
$566,600 Zestimate®
$178/sqft
$500/mo HOA
What's special
Gas fireplaceRelaxing mountain viewsMain level laundry roomCovered deckProfessionally designed lower-level patioCozy fire pitPool table
- 44 days
- on Zillow |
- 318 |
- 15 |
Zillow last checked: 7 hours ago
Listing updated: July 07, 2025 at 09:03am
Listed by:
Mike Kennedy 301-616-6106,
Railey Realty, Inc. 301-387-2000
Source: Bright MLS,MLS#: MDGA2009744

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
- Main level bathrooms: 2
- Main level bedrooms: 1
Basement
- Area: 0
Heating
- Forced Air, Propane
Cooling
- Central Air, Ceiling Fan(s), Electric
Appliances
- Included: Microwave, Dishwasher, Disposal, Dryer, Oven/Range - Electric, Refrigerator, Stainless Steel Appliance(s), Washer, Electric Water Heater
- Laundry: Lower Level
Features
- Bar, Bathroom - Tub Shower, Ceiling Fan(s), Combination Dining/Living, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Open Floorplan, Primary Bath(s), Recessed Lighting, Upgraded Countertops, Walk-In Closet(s), Dry Wall
- Flooring: Ceramic Tile, Hardwood, Carpet, Wood
- Doors: Sliding Glass
- Windows: Casement
- Basement: Finished,Heated,Improved,Walk-Out Access,Connecting Stairway
- Has fireplace: No
Interior area
- Total structure area: 3,300
- Total interior livable area: 3,300 sqft
- Finished area above ground: 3,300
- Finished area below ground: 0
Property
Parking
- Parking features: Assigned, Driveway
- Has uncovered spaces: Yes
- Details: Assigned Parking
Accessibility
- Accessibility features: None
Features
- Levels: Three
- Stories: 3
- Patio & porch: Deck, Patio, Porch
- Exterior features: Extensive Hardscape
- Pool features: None
- Has spa: Yes
- Spa features: Bath, Hot Tub
- Has view: Yes
- View description: Mountain(s)
- Waterfront features: Lake
Lot
- Features: Backs to Trees, Backs - Open Common Area, Landscaped, No Thru Street
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1218087111
- Zoning: TR
- Zoning description: Town Residential
- Special conditions: Standard
Construction
Type & style
- Home type: Condo
- Architectural style: Villa
- Property subtype: Condominium
- Attached to another structure: Yes
Materials
- HardiPlank Type, Stone
- Foundation: Block
- Roof: Shingle
Condition
- New construction: No
- Year built: 2008
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable
Community & HOA
Community
- Subdivision: Timberlake Village
HOA
- Has HOA: No
- Amenities included: Common Grounds
- Services included: Common Area Maintenance, Maintenance Structure, Maintenance Grounds, Road Maintenance, Snow Removal
- HOA name: Timberlake Village
- Condo and coop fee: $500 monthly
Location
- Region: Oakland
Financial & listing details
- Price per square foot: $178/sqft
- Tax assessed value: $560,000
- Annual tax amount: $5,684
- Date on market: 6/11/2025
- Listing agreement: Exclusive Right To Sell
- Listing terms: Conventional,Cash
- Ownership: Condominium
- Loading
- Loading