285 Winding Trail Ln #10a, OAKLAND, MD 21550
Local realty services provided by:Better Homes and Gardens Real Estate Community Realty



285 Winding Trail Ln #10a,OAKLAND, MD 21550
$575,000
- 5 Beds
- 5 Baths
- 3,300 sq. ft.
- Single family
- Pending
Listed by:michael n kennedy
Office:railey realty, inc.
MLS#:MDGA2009744
Source:BRIGHTMLS
Price summary
- Price:$575,000
- Price per sq. ft.:$174.24
About this home
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!
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Home facts
- Year built:2008
- Listing Id #:MDGA2009744
- Added:65 day(s) ago
- Updated:August 16, 2025 at 07:27 AM
Rooms and interior
- Bedrooms:5
- Total bathrooms:5
- Full bathrooms:4
- Half bathrooms:1
- Living area:3,300 sq. ft.
Heating and cooling
- Cooling:Ceiling Fan(s), Central A/C
- Heating:Forced Air, Propane - Leased
Structure and exterior
- Roof:Shingle
- Year built:2008
- Building area:3,300 sq. ft.
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$575,000
- Price per sq. ft.:$174.24
- Tax amount:$5,684 (2024)
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