21550

Luxury Homes For Sale in Oakland MD

19Results

Browse beautiful luxury homes for sale in Oakland, Maryland, today! Get in touch with Railey Realty or give us a call at 301-387-2000 for expert guidance to find your dream home in Oakland. Don’t forget to register and unlock features like saving favorites and receiving alerts on the latest listings.

Newest
New Listing
415 Nazelrod Road Oakland MD 21550

$3,249,000

Oakland, MD

415 Nazelrod Road

  • 4 Beds
  • 5 Baths
  • 63.42 Acres
  • 6,036 SqFt
  • 16 Days on Market
MLS#: MDGA2012154
New Listing

$1,350,000

Oakland, MD

211 High Point Ridge Road

  • 4 Beds
  • 4 Baths
  • 7.68 Acres
  • 3,472 SqFt
  • 30 Days on Market
MLS#: MDGA2011990

$1,579,900

Oakland, MD

2311 Boy Scout Road

  • 4 Beds
  • 3 Baths
  • 0.93 Acres
  • 3,278 SqFt
  • 31 Days on Market
MLS#: MDGA2012046
Open House

$1,200,000

Oakland, MD

122 Woodlands Hill Lane

NEXT OPEN HOUSE:

Tue 6/30 1:00 PM to 4:00 PM

  • 4 Beds
  • 5 Baths
  • 6.89 Acres
  • 2,656 SqFt
  • 32 Days on Market
MLS#: MDGA2011982

$1,689,000

Oakland, MD

670 Woodlands Hill Lane

  • 5 Beds
  • 5 Baths
  • 1.95 Acre
  • 3,714 SqFt
  • 38 Days on Market
MLS#: MDGA2011904

$1,189,000

Oakland, MD

248 Tarn Drive

  • 6 Beds
  • 6 Baths
  • 1 Acre
  • 3,482 SqFt
  • 40 Days on Market
MLS#: MDGA2011874

$2,499,900

Oakland, MD

83 Bethlehem Road

  • 4 Beds
  • 2 Baths
  • 327.72 Acres
  • 2,190 SqFt
  • 41 Days on Market
MLS#: MDGA2011892

$1,025,000

Oakland, MD

127 Paradise Heights

  • 3 Beds
  • 3 Baths
  • 1.26 Acre
  • 2,240 SqFt
  • 52 Days on Market
MLS#: MDGA2011804

$1,400,000

Oakland, MD

827 Penn Point Road

  • 5 Beds
  • 4 Baths
  • 0.76 Acres
  • 2,832 SqFt
  • 67 Days on Market
MLS#: MDGA2011664

$1,100,000

Oakland, MD

660 Glendale Road

  • 5 Beds
  • 3 Baths
  • 0.3 Acres
  • 2,592 SqFt
  • 73 Days on Market
MLS#: MDGA2011188

$1,074,900

Oakland, MD

52 Dam View Drive

  • 4 Beds
  • 6 Baths
  • 0.59 Acres
  • 3,032 SqFt
  • 129 Days on Market
MLS#: MDGA2011104

$2,500,000

Oakland, MD

19530 Garrett Highway

  • 1988 Year Built
  • 6.62 Acres
  • 129 Days on Market
MLS#: MDGA2010798

Oakland, MD boasts a remarkable selection of luxury homes, featuring stunning architecture, high-end finishes, and prime locations. Many properties provide breathtaking views of Deep Creek Lake, private lake access, and custom amenities such as gourmet kitchens, spacious outdoor spaces, and spa-like retreats. Whether nestled in a serene wooded area or perched along the lakefront, these residences offer unparalleled comfort and exclusivity. Living in one of Oakland’s luxury homes means enjoying a blend of sophistication, privacy, and access to the area's outdoor and recreational activities.

Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Railey Realty, Inc participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated June 29, 2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.