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178 Winding Trail Ln #5b, 
Oakland, MD 21550

$589,000

5

Beds

5

Baths

3,300

Sq Ft

Single Family

Active

Listed by

Nina A Beitzel

Railey Realty, Inc.

Last updated:

January 14, 2026, 03:14 PM

MLS#

MDGA2010960

Source:

BRIGHTMLS

About This Home

178 Winding Trail Ln #5b

Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lake has to offer, Whispering Pines is the ultimate turnkey mountain retreat. This impeccably maintained 5-bedroom townhome spans three levels of inviting living space and features an attached garage—perfect for hosting family, friends, or guests year-round. Enjoy the best of both worlds: a private, serene atmosphere with the ease of low-maintenance living and a welcoming community feel through the HOA. Already an established and successful vacation rental, this property is truly ready to enjoy or generate income from day one. Just minutes from Wisp Resort, Deep Creek Lake State Park, restaurants, shopping, and endless outdoor adventure—this is the lifestyle and investment opportunity you’ve been waiting for!

Home Facts

Single Family

5 Baths

5 Bedrooms

Built in 2006

Price Summary

589,000

$178 per Sq. Ft.

MLS #:

MDGA2010960

Last Updated:

January 14, 2026, 03:14 PM

Added:

6 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:

Contemporary

Building Area:

3,300 Sq. Ft.

Year Built:

2006

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. © 2026 Bright Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.