Oakland, MD

Houses for Sale in Oakland, MD

86Results

Oakland is the most searched town on our site, and single-family houses make up a large share of its listings. See all Oakland real estate, create a free account to save this search and receive alerts, or call Railey Realty at 301-387-2000 to speak with an agent.

Newest
New Listing
74 Parks Road Oakland MD 21550

$59,900

Oakland, MD

74 Parks Road

  • 3 Beds
  • 1 Bath
  • 1.85 Acre
  • 792 SqFt
  • 8 Days on Market
MLS#: MDGA2012962
New Listing

$475,000

Oakland, MD

335 Pergin Farm Road

  • 3 Beds
  • 3 Baths
  • 2 Acres
  • 2,912 SqFt
  • 8 Days on Market
MLS#: MDGA2012876
New Listing

$269,900

Oakland, MD

1050 Christopher Way

  • 2 Beds
  • 2 Baths
  • 3 Acres
  • 1,050 SqFt
  • 8 Days on Market
MLS#: MDGA2012956
New Listing

$299,000

Oakland, MD

459 Santa Fe Trail

  • 3 Beds
  • 2 Baths
  • 0.5 Acres
  • 1,344 SqFt
  • 9 Days on Market
MLS#: MDGA2012948
New Listing

$909,000

Oakland, MD

2296 Lake Shore Drive

  • 4 Beds
  • 3 Baths
  • 1.15 Acre
  • 2,796 SqFt
  • 12 Days on Market
MLS#: MDGA2012922
New Listing

$295,000

Oakland, MD

228 N 4th Street

  • 3 Beds
  • 2 Baths
  • 0.31 Acres
  • 1,562 SqFt
  • 12 Days on Market
MLS#: MDGA2012944
New Listing

$225,000

Oakland, MD

5423 Gorman Road

  • 1 Bath
  • 1.93 Acre
  • 720 SqFt
  • 13 Days on Market
MLS#: MDGA2012924
New Listing

$349,000

Oakland, MD

2092 Gorman Road

  • 4 Beds
  • 2 Baths
  • 3.16 Acres
  • 4,004 SqFt
  • 14 Days on Market
MLS#: MDGA2012894
New Listing

$155,000

Oakland, MD

503 E Alder Street

  • 4 Beds
  • 2 Baths
  • 0.25 Acres
  • 2,512 SqFt
  • 14 Days on Market
MLS#: MDGA2012928
New Listing

$2,100,000

Oakland, MD

1038 S Blakeslee Road

  • 5 Beds
  • 6 Baths
  • 1.11 Acre
  • 4,074 SqFt
  • 18 Days on Market
MLS#: MDGA2012896
New Listing

$785,000

Oakland, MD

1515 Upperman Road

  • 1 Bed
  • 1 Bath
  • 150 Acres
  • 1,200 SqFt
  • 18 Days on Market
MLS#: MDGA2012760
New Listing

$225,000

Oakland, MD

210 Seneca Avenue

  • 3 Beds
  • 1 Bath
  • 0.16 Acres
  • 1,204 SqFt
  • 19 Days on Market
MLS#: MDGA2012886

Single-Family Homes in Oakland, Maryland

Oakland is the county seat of Garrett County, and its houses range from Victorian and early 1900s homes on the streets around the historic B&O railroad station to ranches and newer homes in the neighborhoods outside town and near the south end of Deep Creek Lake. Swallow Falls and Herrington Manor state parks are a short drive away, and Route 219 connects Oakland north to McHenry and the lake. Winters bring plenty of snow, so garages and covered parking are popular. This search lists every single-family house for sale in Oakland. Railey Realty works throughout Garrett County. See Oakland homes with a garage or browse 3 bedroom homes in Oakland.

Frequently Asked Questions

What is Oakland, MD known for?
Oakland is the Garrett County seat and is known for its historic B&O railroad station, its downtown and its location near Deep Creek Lake.
How far is Oakland from Deep Creek Lake?
The south end of Deep Creek Lake is only a few miles from downtown Oakland by Route 219.

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 October 20, 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.