21550

Homes For Sale in Oakland MD

68Results

Browse all 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
953 Bray School Road Oakland MD 21550

$299,900

Oakland, MD

953 Bray School Road

  • 3 Beds
  • 1 Bath
  • 1.38 Acre
  • 1,008 SqFt
  • 0 Days on Market
MLS#: MDGA2012238
New Listing

$399,900

Oakland, MD

321 Deer Park Hotel Road

  • 3 Beds
  • 2 Baths
  • 0.96 Acres
  • 2,476 SqFt
  • 7 Days on Market
MLS#: MDGA2012166
New Listing

$249,000

Mountain Lake Park, MD

106 G

  • 4 Beds
  • 1 Bath
  • 0.28 Acres
  • 1,432 SqFt
  • 10 Days on Market
MLS#: MDGA2012192
New Listing

$340,000

Oakland, MD

254 Little Mountain Road

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

$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

$415,000

Oakland, MD

1499 Foster Road

  • 4 Beds
  • 2 Baths
  • 1.17 Acre
  • 2,234 SqFt
  • 22 Days on Market
MLS#: MDGA2012068
Open House

$434,900

Oakland, MD

511 Hilltop Road

NEXT OPEN HOUSE:

Fri 7/3 1:00 PM to 4:00 PM

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

$195,000

Oakland, MD

2918 Oakland Sang Run Road

  • 3 Beds
  • 1 Bath
  • 4.88 Acres
  • 1,382 SqFt
  • 31 Days on Market
MLS#: MDGA2012034

$969,000

Oakland, MD

251 Robinwood Drive

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

Oakland, MD boasts a wide selection of homes, ranging from cozy cottages to expansive estates, catering to diverse lifestyles. Many properties feature desirable amenities like scenic views, spacious interiors, and modern upgrades. With its charming small-town atmosphere and proximity to recreational activities and local attractions, Oakland offers an inviting place to settle down. Whether you're looking for a tranquil retreat or a welcoming community setting, Oakland's real estate options provide something for everyone.

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.