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$559,250

  • Sold
  • Closed
  • Condo
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 3,300 Sq. Ft.
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See This Home
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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!

Full Property Details for 285 Winding Trail Ln #10A

General

  • Sold For: $559,250
  • Taxes: $5,684 (2024)
  • Status: Closed
  • Type: Condo
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDGA2009744
  • Added to Site: 220 day(s) ago

Interior

  • Interior Features: 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
  • Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer, Oven/Range - Electric, Refrigerator, Stainless Steel Appliances, Washer
  • Flooring: Ceramic Tile, Hardwood, Carpet

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 2
  • Main - Full Baths: 1
  • Main - 1/2 Baths: 1
  • Lower Floor Baths: 1
  • Lower - Full Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 2
  • Bedrooms Lower: 2
  • Bedrooms Main & Up: 1

Other Rooms

  • Laundry: Lower Floor

Additional Information

  • Shared Amenities: Common Grounds

Exterior

  • Exterior Features: Extensive Hardscape, Hot Tub
  • Porch/Patio/Deck: Deck(s), Patio(s), Porch(es)

Parking

  • Assigned Spaces: 4
  • Parking Features: Assigned, Paved Driveway
  • Parking Type: Driveway

Location

  • County: Garrett
  • Development Name: Timberlake Village
  • Subdivision: Timberlake Village
  • Driving 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.
  • Location Details: Lake

School Information

  • School District: Garrett County Public Schools

Community

  • Assoc. Fees Include: Common Area Maintenance, Ext Bldg Maint, Lawn Maintenance, Road Maintenance, Snow Removal
  • Pets Allowed: Yes
  • Pets: Dogs OK

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Ceiling Fan(s)
  • Cooling Fuel: Electric
  • Heating Type: Forced Air
  • Heating Fuel: Propane - Leased
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Info: Villa
  • Architectural Style: Villa
  • Structure Type: Twin/Semi-Detached
  • Construction: HardiPlank Type, Stone
  • Basement: Yes
  • Basement Desc.: Fully Finished, Heated, Improved, Walkout Level, Connecting Stairway
  • Foundation: Block
  • Roof: Shingle
  • Walls/Ceilings: Dry Wall
  • Windows: Casement
  • Doors: Sliding Glass
  • Stories/Levels: 0
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 3,300
  • Sq. Ft. Source: Assessor
  • Living Area: 3,300 Sq. Ft.
  • Year Built: 2008
  • Year Built Source: Assessor

Unit Information

Unit 1

  • Bathrooms-Lower: 1
  • Bedrooms-Lower: 2

Lot Features

  • Property View: Mountain
  • Lot Features: Backs to Trees, Backs - Open Common Area, Landscaping, No Thru Street
  • Zoning: TR
  • Lot Description: Backs to Trees, Backs - Open Common Area, Landscaping, No Thru Street

Financial Considerations

  • Price Per Sq. Ft.: $174.24
  • Assessment Year: 2025
  • County Tax: $5,684
  • County Tax Freq: Annually
  • Tax w/Assessment: $560,000
  • Tax Amount: $5,684
  • Tax Year: 2024
  • Terms: Standard Sale
  • Tax Total Finished Sq. Ft.: 3300

Disclosures and Reports

  • Ownership: Condominium
  • Condo: Yes
  • Lot Number: 771

Listed by Railey Realty, Inc., Michael N Kennedy
Sold by The KW Collective, Julia Mead

Listing agent

— 285 Winding Trail Ln #10A —

  • Michael N Kennedy

    Railey Realty, Inc.

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 285 Winding Trail Ln #10A

School District:Garrett County Public Schools
NameGradesDistance
Broad Ford Elementary School
607 Harvey Winters Drive, Oakland, MD 21550
PK-56.4 mi
Southern Middle School, Oakland, MD
605 Harvey Winters Drive, Oakland, MD 21550
6-86.4 mi
Southern Garrett High School
345 Oakland Drive, Oakland, MD 21550
9-127.4 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 285 Winding Trail Ln #10A

Date
Details
Price
Change
Source
9/02/2025
Sold
$559,250
-2.74%
MLS
7/31/2025
Price Reduced
$575,000
-2.38%
MLS
6/11/2025
Listed
$589,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Railey Realty, Inc., Michael N Kennedy
Sold by The KW Collective, Julia Mead

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285 Winding Trail Lane #10A, Oakland, MD 21550 (MLS# MDGA2009744) is a Condo property that was sold at $559,250 on September 02, 2025. Want to learn more about 285 Winding Trail Lane #10A? Do you have questions about finding other Condo real estate for sale in Oakland? You can browse all Oakland real estate or contact a Coldwell Banker agent to request more information.