Oakland, MD

Oakland MD Real Estate for Sale

208Results

View all currently available real estate for sale in Oakland, Maryland. A charming town in Garrett County, Oakland is known for its rich history, beautiful natural surroundings, and proximity to Deep Creek Lake. With a picturesque downtown, it offers local shops, restaurants, and access to outdoor recreation like hiking, fishing, and skiing. Questions? Contact Railey Realty or call 301-387-2000 to schedule a showing! Don't Forget! Register to save your favorite listings and receive updates on similar properties.

Newest
New Listing
308 Winding Trail Lane Oakland MD 21550

$615,000

Oakland, MD

308 Winding Trail Lane, Unit 11B

  • 5 Beds
  • 5 Baths
  • 3,300 SqFt
  • 1 Day on Market
MLS#: MDGA2012146
New Listing

$3,249,000

Oakland, MD

415 Nazelrod Road

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

$340,000

Oakland, MD

254 Little Mountain Road

  • 4 Beds
  • 2 Baths
  • 4.96 Acres
  • 1,792 SqFt
  • 3 Days on Market
MLS#: MDGA2012150
New Listing

$739,000

Oakland, MD

12 Arrowhead Lane, Unit 12

  • 3 Beds
  • 3 Baths
  • 1,650 SqFt
  • 5 Days on Market
MLS#: MDGA2012110
New Listing

$19,900

Oakland, MD

Lot 18 Buck Drive

  • Land
  • 1.35 Acre
  • 5 Days on Market
MLS#: MDGA2011342
New Listing

$220,000

Oakland, MD

1256 Boiling Spring Road

  • 3 Beds
  • 2 Baths
  • 1.72 Acre
  • 1,456 SqFt
  • 6 Days on Market
MLS#: MDGA2012084
New Listing

$42,000

Oakland, MD

Maple Del Lane

  • Land
  • 1.05 Acre
  • 6 Days on Market
MLS#: MDGA2012116
New Listing

$599,000

Oakland, MD

428 Sam Snead Circle

  • 5 Beds
  • 4 Baths
  • 0.71 Acres
  • 3,542 SqFt
  • 8 Days on Market
MLS#: MDGA2012104
New Listing

$415,000

Oakland, MD

1499 Foster Road

  • 4 Beds
  • 2 Baths
  • 1.17 Acre
  • 2,234 SqFt
  • 9 Days on Market
MLS#: MDGA2012068
New Listing

$19,000

Oakland, MD

6 Cedar Lane

  • Land
  • 0.49 Acres
  • 11 Days on Market
MLS#: MDGA2012062
New Listing

$379,500

Oakland, MD

20160 Garrett Highway, Unit C307

  • 1 Bed
  • 1 Bath
  • 636 SqFt
  • 11 Days on Market
MLS#: MDGA2012092
New Listing

$434,900

Oakland, MD

511 Hilltop Road

  • 4 Beds
  • 3 Baths
  • 4.09 Acres
  • 2,406 SqFt
  • 12 Days on Market
MLS#: MDGA2012082

Oakland MD Properties for Sale

Oakland, Maryland is a charming town situated in Garrett County. Serving as the county seat, Oakland is known for its rich history and beautiful natural surroundings. The town features a picturesque downtown area lined with historic buildings, local shops, and restaurants. Oakland is also a gateway to outdoor recreation, as it is located near the stunning Deep Creek Lake and offers access to hiking trails, fishing spots, and skiing during the winter months. With its blend of small-town charm, cultural attractions, and proximity to nature, Oakland is a delightful destination for residents and visitors alike.

Browse Garrett County Real Estate:
Accident | Deer Park | Friendsville | Frostburg | Grantsville | Kitzmiller | Loch Lynn Heights | Lonaconing | Mountain Lake Park | Swanton

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 16, 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.