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285 Winding Trail Ln #10a, 
Oakland, MD 21550

$589,000


5

Beds


5

Baths


3,300

Sq Ft


Single Family

Active

Listed by

Michael N Kennedy

Railey Realty, Inc.

Last updated:

June 22, 2025, 02:14 PM

MLS#

MDGA2009744

Source:

BRIGHTMLS

About This Home

285 Winding Trail Ln #10a

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!

Home Facts

Single Family

5 Baths

5 Bedrooms

Built in 2008

Price Summary

589,000

$178 per Sq. Ft.

MLS #:

MDGA2009744

Last Updated:

June 22, 2025, 02:14 PM

Added:

11 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

4

Interior

Living Area:

3,300 Sq. Ft.


Structure

Structure

Architectural Style:

Villa

Building Area:

3,300 Sq. Ft.

Year Built:

2008


Finances & Disclosures

Finances

Price:

$589,000

Price per Sq. Ft:

$178 per Sq. Ft.

Source:BRIGHTMLS
The information being provided by Bright MLS is for the consumer’s 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 is deemed reliable but not guaranteed and should therefore be independently verified. © 2025 Bright MLS All rights reserved.

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