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!
Sold for $559,250
$559,250
285 Winding Trail Ln Unit 10A, Oakland, MD 21550
5beds
3,300sqft
Condominium
Built in 2008
-- sqft lot
$553,200 Zestimate®
$169/sqft
$3,862 Estimated rent
Home value
$553,200
$437,000 - $697,000
$3,862/mo
Zestimate® history
Owner options
List your home for rent
$3,862/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$3,862/mo
Rent Zestimate®
Refinance and save
$3,451/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$3,451/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Gas fireplaceRelaxing mountain viewsMain level laundry roomCovered deckProfessionally designed lower-level patioCozy fire pitPool table
Zillow last checked:
Listing updated:
Listed by:
Mike Kennedy 301-616-6106,
Railey Realty, Inc.
Bought with:
Julie Mead, 666198
The KW Collective
Source: Bright MLS,MLS#: MDGA2009744
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
- Condo and coop fee: $500 monthly
- 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
Location
- Region: Oakland
Financial & listing details
- Price per square foot: $169/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
Price history
| Date | Event | Price |
|---|---|---|
| 9/2/2025 | Sold | $559,250-2.7%$169/sqft |
Source:  Bright MLS #MDGA2009744 Report a problem | ||
| 8/12/2025 | Contingent | $575,000$174/sqft |
Source: Bright MLS #MDGA2009744 Report a problem | ||
| 7/31/2025 | Price change | $575,000-2.4%$174/sqft |
Source: Bright MLS #MDGA2009744 Report a problem | ||
| 6/11/2025 | Listed for sale | $589,000+68.3%$178/sqft |
Source: Bright MLS #MDGA2009744 Report a problem | ||
| 12/12/2019 | Sold | $350,000-2.5%$106/sqft |
Source: Public Record Report a problem | ||
| 11/18/2019 | Pending sale | $359,000$109/sqft |
Source: Railey Realty, Inc. #MDGA131518 Report a problem | ||
| 11/14/2019 | Price change | $359,000-2.7%$109/sqft |
Source: Railey Realty, Inc. #MDGA131518 Report a problem | ||
| 10/30/2019 | Listed for sale | $369,000$112/sqft |
Source: Railey Realty, Inc. #MDGA131518 Report a problem | ||
| 10/18/2019 | Pending sale | $369,000$112/sqft |
Source: Railey Realty, Inc. #MDGA131518 Report a problem | ||
| 10/10/2019 | Listed for sale | $369,000+7.6%$112/sqft |
Source: Railey Realty, Inc. #MDGA131518 Report a problem | ||
| 12/17/2013 | Sold | $343,000-1.7%$104/sqft |
Source: Public Record Report a problem | ||
| 9/17/2013 | Listed for sale | $349,000-20%$106/sqft |
Source: Long & Foster Real Estate #GA8183057 Report a problem | ||
| 5/6/2008 | Sold | $436,500$132/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $7,179 +26.3% | $560,000 +15.1% |
| 2024 | $5,684 +17.7% | $486,667 +17.7% |
| 2023 | $4,828 +21.6% | $413,333 +21.6% |
| 2022 | $3,971 | $340,000 |
| 2021 | $3,971 | $340,000 |
| 2020 | $3,971 | $340,000 |
| 2019 | $3,971 +6% | $340,000 |
| 2018 | $3,746 0% | $340,000 |
| 2017 | $3,747 | $340,000 |
| 2016 | -- | $340,000 |
| 2015 | -- | $340,000 |
| 2014 | -- | $340,000 -11.7% |
| 2013 | -- | $385,000 |
| 2012 | -- | $385,000 |
| 2011 | -- | $385,000 -4.9% |
| 2010 | -- | $405,000 +0.8% |
| 2009 | -- | $401,666 +372.5% |
| 2008 | -- | $85,000 |
Find assessor info on the county website
Neighborhood: 21550
Nearby homes
- $560,0005 bd5 ba3.3k sqft287 Winding Trail Ln #10B, Oakland, MD 21550Sold
- $579,300-- bd4 ba3.3k sqft267 Winding Trail Ln UNIT 9B, Oakland, MD 21550Off Market
- $603,600-- bd4 ba3.3k sqft265 Winding Trail Ln #9A, Oakland, MD 21550Off Market
- $43,900-- bd-- ba-- sqftZeddock Miller Rd, Oakland, MD 21550Off Market
- $554,9995 bd5 ba3.3k sqft247 Winding Trail Ln #6B, Oakland, MD 21550Sold
- $615,0005 bd5 ba3.3k sqft308 Winding Trail Ln #11B, Oakland, MD 21550For Sale
- $612,600-- bd4 ba3k sqft245 Winding Trail Ln #6A, Oakland, MD 21550Off Market
- $623,800-- bd4 ba3.3k sqft140 Winding Trail Ln UNIT 3B, Oakland, MD 21550Off Market
Nearby schools
GreatSchools rating
- 4/10Broad Ford Elementary SchoolGrades: PK-6Distance: 6.4 mi
- 5/10Southern Garrett High SchoolGrades: 7-12Distance: 7.4 mi
Schools provided by the listing agent
- District: Garrett County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Get pre-qualified for a loan
At Zillow Home Loans, we can pre-qualify you in as little as 5 minutes with no impact to your credit score.An equal housing lender. NMLS #10287.
- Maryland
- Garrett County
- Oakland
- 21550
- 285 Winding Trail Ln Unit 10A
Nearby cities
Nearby zip codes
Other Oakland Topics
