Oakland, MD

4+ Bedroom Homes for Sale in Oakland, MD

48Results

Houses with four or more bedrooms make up just over half of the single-family homes for sale in Oakland. Compare all Oakland houses for sale, 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
2296 Lake Shore Drive Oakland MD 21550

$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

$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

$679,000

Oakland, MD

870 Hunters Ridge Drive

  • 4 Beds
  • 3 Baths
  • 4.4 Acres
  • 2,896 SqFt
  • 27 Days on Market
MLS#: MDGA2012844

$499,000

Oakland, MD

607 Pin Oak Circle

  • 5 Beds
  • 4 Baths
  • 0.56 Acres
  • 3,800 SqFt
  • 38 Days on Market
MLS#: MDGA2012740

$289,000

Oakland, MD

586 Bray School Road

  • 4 Beds
  • 2 Baths
  • 1 Acre
  • 2,240 SqFt
  • 43 Days on Market
MLS#: MDGA2012712

$899,900

Oakland, MD

395 Woodlands Hill Lane

  • 5 Beds
  • 6 Baths
  • 2.03 Acres
  • 3,160 SqFt
  • 57 Days on Market
MLS#: MDGA2012628

$444,700

Oakland, MD

333 Sloan Tract Road

  • 4 Beds
  • 4 Baths
  • 0.41 Acres
  • 1,585 SqFt
  • 64 Days on Market
MLS#: MDGA2012576

$1,199,000

Oakland, MD

20698 Garrett Highway

  • 4 Beds
  • 3 Baths
  • 0.28 Acres
  • 1,844 SqFt
  • 65 Days on Market
MLS#: MDGA2012616

$430,000

Oakland, MD

704 Old Crellin Road

  • 5 Beds
  • 3 Baths
  • 3.91 Acres
  • 2,507 SqFt
  • 66 Days on Market
MLS#: MDGA2012604

$3,950,000

Oakland, MD

1131 Lake Shore Drive

  • 8 Beds
  • 10 Baths
  • 1.53 Acre
  • 6,486 SqFt
  • 72 Days on Market
MLS#: MDGA2012514

Oakland, Maryland Houses with Four or More Bedrooms

Larger homes in Oakland include older Victorians and farmhouses near town, lake area homes built for gatherings of family and friends, and newer homes on wooded lots outside town. Extra bedrooms are popular with second home owners who host guests or rent their homes during ski and summer seasons, and with full time residents who want room for a home office. Many of these homes include finished lower levels, decks and garages. This search lists every single-family house in Oakland with four or more bedrooms. Railey Realty can help you compare layout and location. See Oakland homes over $500K or browse Oakland homes with a garage.

Frequently Asked Questions

Why are larger homes popular in Oakland?
Many owners host family and guests at the lake, and some rent their homes during the ski and summer seasons.
Do larger Oakland homes have garages?
Many do, along with finished lower levels and decks. The listing details show garage spaces.

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.