Oakland, MD

Oakland, MD Homes for Sale Over $500K

47Results

View homes priced over $500,000 in Oakland, Maryland, located near Deep Creek Lake, local parks, and year-round outdoor recreation. This price tier includes spacious homes, custom builds, and investment-ready properties with desirable features and locations. Listings are regularly updated to provide the most current availability. Contact Railey Realty for property details or register to save listings and get email alerts for new homes.

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
  • 14 Days on Market
MLS#: MDGA2012146
New Listing

$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

$739,000

Oakland, MD

12 Arrowhead Lane, Unit 12

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

$599,000

Oakland, MD

428 Sam Snead Circle

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

$715,000

Oakland, MD

250 Lehman Lane, Unit 39

  • 4 Beds
  • 5 Baths
  • 3,240 SqFt
  • 25 Days on Market
MLS#: MDGA2011896
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

$969,000

Oakland, MD

251 Robinwood Drive

  • 5 Beds
  • 5 Baths
  • 5.62 Acres
  • 4,284 SqFt
  • 31 Days on Market
MLS#: MDGA2011890
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

$795,000

Oakland, MD

312 Moss Creek Circle

  • 5 Beds
  • 4 Baths
  • 1.83 Acre
  • 4,230 SqFt
  • 39 Days on Market
MLS#: MDGA2011736

$1,189,000

Oakland, MD

248 Tarn Drive

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

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.