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5 Bedroom Homes in Oakland, MD
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5 Bedroom Homes in Oakland, MD

5 Bedroom Homes in Oakland, MD

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16 Listings
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5 Bedroom Homes in Oakland, MD

16 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 5979 Cranesville Rd — photo65Active

    $339,000

    5 bd · 4 ba · 2,628 sqft

    5979 Cranesville Rd, Oakland, MD

    Laura C Newhall · Taylor-Made Deep Creek Sales

  2. 607 Pin Oak Cir — photo77Active

    $499,000

    5 bd · 4 ba · 3,800 sqft

    607 Pin Oak Cir, Oakland, MD

    Rachel Bruch · Railey Realty, Inc.

  3. 704 Old Crellin Rd — photo31Active

    $430,000

    5 bd · 3 ba · 2,507 sqft

    704 Old Crellin Rd, Oakland, MD

    Andrew C Orr · The KW Collective

  4. 395 Woodlands Hill Ln — photo66Active

    $899,900

    5 bd · 6 ba · 3,160 sqft

    395 Woodlands Hill Ln, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  5. 5154 Maryland Hwy — photo68Active

    $460,000

    5 bd · 2 ba · 2,860 sqft

    5154 Maryland Hwy, Oakland, MD

    Wilda Charlene Deremer Aburn · Coldwell Banker Home Town Realty

  6. 251 Robinwood Dr — photoPrice Reduced62Active

    $750,000

    5 bd · 5 ba · 4,284 sqft

    251 Robinwood Dr, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  7. 615 E Oak St — photo60Active

    $365,000

    5 bd · 3 ba · 2,652 sqft

    615 E Oak St, Oakland, MD

    Lucas Alan Muenchow · Railey Realty, Inc.

  8. 943 Paradise Hts — photoPrice Reduced62Active

    $699,000

    5 bd · 3 ba · 2,200 sqft

    943 Paradise Hts, Oakland, MD

    Lucas Alan Muenchow · Railey Realty, Inc.

  9. 308 Winding Trail Ln #11B — photoPrice Reduced61Active

    $599,999

    5 bd · 5 ba · 3,300 sqft

    308 Winding Trail Ln #11B, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  10. 428 Sam Snead Cir — photoPrice Reduced86Active

    $549,000

    5 bd · 4 ba · 3,542 sqft

    428 Sam Snead Cir, Oakland, MD

    Justin D Liller · Railey Realty, Inc.

  11. 321 N 3rd St — photoPrice Reduced48Active

    $350,000

    5 bd · 2 ba · 3,660 sqft

    321 N 3rd St, Oakland, MD

    Christina M Ford · CENTURY 21 New Millennium

  12. 251 Robinwood Dr — photoPrice Reduced63Active

    $850,000

    5 bd · 5 ba · 4,284 sqft

    251 Robinwood Dr, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  13. 312 Moss Creek Cir — photoPrice Reduced55Active

    $699,000

    5 bd · 4 ba · 4,230 sqft

    312 Moss Creek Cir, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  14. 638 Glendale Rd — photo58Active

    $745,000

    5 bd · 3 ba · 2,640 sqft

    638 Glendale Rd, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  15. 660 Glendale Rd — photoPrice Reduced62Active

    $949,000

    5 bd · 3 ba · 2,592 sqft

    660 Glendale Rd, Oakland, MD

    Nick Fratz-Orr · Railey Realty, Inc.

  16. 25 Silver Tree Ln — photoPrice Reduced54Active

    $735,000

    5 bd · 4 ba · 2,364 sqft

    25 Silver Tree Ln, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

About 5 Bedroom Homes in Oakland, MD

5 Bedroom Homes in Oakland, MD: 16 active listings as of November 5, 2026, 13:48 UTC.

Explore Oakland homes

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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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. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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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 Realty.com 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. 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.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-10-28 18:48:43 UTC
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    Oakland, MD community profile

    Population
    1,810
    Median income
    $67,177
    Housing units
    929
    People per sq. mi.
    8.8
    Area
    205.5 sq. mi.

    Source: HJN community data

    Oakland housing market

    October 2026 · This period is still settling

    Oakland 12-month median sale price trend

    Homes that sold · County records, as of Oct 9, 2026

    Median sale price
    $529,000$239,000–$535,000 typical range
    Sales
    14
    Paid in cash
    50.0%

    Homes on the market · MLS, as of Oct 25, 2026

    Median list price
    $454,500
    Homes for sale
    76

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    1,536 sq. ft.