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For sale
  • $589,000

    285 Winding Trail Ln UNIT 10A, Oakland, MD 21550

    5beds
    3,300sqft
    : 
    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
    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!
    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#: MDGA2009744MLS Logo
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    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
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