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285 Winding Trail Lane Unit 10A

OAKLAND, MD 21550

5 beds
5 baths
3,300 sqft
$178 per sqft
2008 build

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!

Listing courtesy of BRIGHT / Railey Realty, Inc.

Last checked: Checking… • Last updated Jun 11, 2025 •

MLS# MDGA2009744 —

The Building

Year Built:

2008
Year Built Source:

Assessor
Roof:

Shingle
New Construction:

No
Construction Materials:

HardiPlank Type, Stone
Structure Type:

Twin/Semi-Detached
Architectural Style:

Villa
Levels:

3
Door Features:

Sliding Glass
Window Features:

Casement
Accessibility Features:

None
Foundation Details:

Block
Basement:

Yes
Basement Type:

Fully Finished, Heated, Improved, Walkout Level, Connecting Stairway
Unit Number:

10A
Total SqFt Source:

Assessor
Total Below Grade SqFt Source:

Assessor
Above Grade Finished Area Units:

Square Feet
Above Grade Finished SqFt:

3300
Above Grade Finished SqFt Source:

Assessor
Below Grade Finished Area Units:

Square Feet
Below Grade Unfinished Area Units:

Square Feet
Below Grade Finished SqFt Source:

Assessor
Below Grade Unfinished SqFt Source:

Assessor
Tax Total Finished SqFt:

3300

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
Flooring Type:

Ceramic Tile, Hardwood, Carpet
Fireplace:

No
Wall & Ceilings:

Dry Wall
Living Area SqFt Source:

Assessor

Room Dimensions

Total SqFt:

3300
Living Area SqFt:

3,300 Sqft

Financial & Terms

Sale Type:

Standard
Acceptable Financing:

Conventional, Cash
Possession:

Settlement

Location

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.
Latitude:

39.49854000
Longitude:

-79.32627000
Location Type:

Lake

The Property

Property Type:

Residential
Lot Features:

Backs to Trees, Backs - Open Common Area, Landscaping, No Thru Street
Zoning:

TR
Zoning Description:

Town Residential
Road Responsibility:

HOA
View:

Mountain
In City Limits:

No
Outdoor Living Structures:

Deck(s), Patio(s), Porch(es)
Other Structures:

Above Grade, Below Grade
Waterview:

No
Waterfront:

No
Water Oriented:

No
Water Access:

No
Navigable Water:

No
Tidal Water:

No
Land Use Code:

U
Riparian Rights:

No

Listing Agent

Contact info:

Taxes

Tax ID Number:

1218087111
Tax Year:

2024
Tax Lot:

771
Tax Annual Amount:

$5,684
Tax Assessed Value:

$560,000
Year Assessed:

2025
County Tax:

5684.00
Total Taxes Payment Frequency:

Annually

Beds

Bedrooms:

5
Bedrooms Main Level:

1
Upper Level Bedrooms:

2
Upper Level 1 Bedrooms:

2
Lower Level Bedrooms:

2
Lower Level Bedrooms:

2

Baths

Total Baths:

5
Full Baths:

4
Half Baths:

1
Main Level Baths:

2.00
Main Level Full Baths:

1
Main Level Half Baths:

1
Upper Level Full Baths:

2
Lower Level Full Baths:

1
Upper Level Total Baths:

2
Upper Level Total Baths:

2.00
All Lower Levels Total Baths:

1
Lower Level Total Baths:

1.00
Upper Level Full Baths:

2
Lower Level Full Baths:

1

Heating & Cooling

Cooling Type:

Central A/C, Ceiling Fan(s)
Central Air:

Yes
Cooling Fuel:

Electric
Heating:

Yes
Heating Type:

Forced Air
Heating Fuel:

Propane - Leased

Utilities

Sewer/Septic:

Public Sewer
Hot Water:

Electric
Water Source:

Public
Internet Services:

Cable

Appliances

Appliances:

Built-In Microwave, Dishwasher, Disposal, Dryer, Oven/Range - Electric, Refrigerator, Stainless Steel Appliances, Washer
Laundry Type:

Lower Floor

Schools

School District Name:

Garrett County Public Schools
School District Source:

Listing Agent

The Community

Subdivision Name:

Timberlake Village
Senior Community:

No
Exterior Features:

Extensive Hardscape, Hot Tub
Pool:

No Pool
HOA:

No
Condo/Coop Association:

Yes
HOA/Condo/Coop Amenities:

Common Grounds
Condo/Coop Fee:

$400
Condo/Coop Fee Frequency:

Monthly
HOA/Condo/Coop Fee:

Common Area Maintenance, Ext Bldg Maint, Lawn Maintenance, Road Maintenance, Snow Removal
Condo/Coop Name:

Timberlake Village

Parking

Garage:

No
Type of Parking:

Driveway
Parking Features:

Assigned, Paved Driveway
Assigned Spaces Count:

4

Extra Units

Vacation Rental:

Yes

Monthly cost estimate

Asking price

$589,000

Expense	Monthly cost
Mortgage	$3,153
Taxes	$473
Insurance	$161
HOA fees	$400
Utilities	$151 See report
Total	$4,338/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
6/11/25 Jun 11, 2025	Listed / Active	BRIGHT	$589,000

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This condo located in MD 21550 is currently for sale for $589,000. 285 Winding Trail Lane Unit 10A is a 3,300 square foot condo with 5 beds and 5 baths. This condo is in the attendance area of Southern Garrett High School, Southern Middle School, and Broad Ford Elementary School.

Listing Courtesy of: BRIGHT and Railey Realty, Inc..

The information included in this listing is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. BRIGHT MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller.