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Oakland, MD Homes for Sale — Page 2 | Realty.com
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Homes for Sale in Oakland, MD

Homes for Sale in Oakland, MD

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24 of 84 Listings
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Homes for Sale in Oakland, MD

24 of 84 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 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.

  2. 139 S Oakhall Dr — photo52Active

    $229,000

    3 bd · 2 ba · 1,612 sqft

    139 S Oakhall Dr, Oakland, MD

    Laura C Newhall · Taylor-Made Deep Creek Sales

  3. 586 Bray School Rd — photoPrice Reduced32Active

    $269,000

    4 bd · 2 ba · 2,240 sqft

    586 Bray School Rd, Oakland, MD

    Julia Mead · The KW Collective

  4. 482 Pergin Farm Rd — photo34Active

    $449,000

    3 bd · 2 ba · 2,160 sqft

    482 Pergin Farm Rd, Oakland, MD

    Laura C Newhall · Taylor-Made Deep Creek Sales

  5. 100 San Francisco St — photo52Active

    $645,000

    2 bd · 2 ba · 1,520 sqft

    100 San Francisco St, Oakland, MD

    Nick Fratz-Orr · Railey Realty, Inc.

  6. 333 Sloan Tract Rd — photo61Active

    $444,700

    4 bd · 4 ba · 1,585 sqft

    333 Sloan Tract Rd, Oakland, MD

    Debra A Beitzel · Long & Foster Real Estate, Inc.

  7. 20698 Garrett Hwy — photo53Active

    $1,199,000

    4 bd · 3 ba · 1,844 sqft

    20698 Garrett Hwy, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  8. 1407 Broadford Rd — photo52Active

    $399,900

    3 bd · 2 ba · 1,464 sqft

    1407 Broadford Rd, Oakland, MD

    Laura C Newhall · Taylor-Made Deep Creek Sales

  9. 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

  10. 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.

  11. 180 Paradise Ridge Rd — photo59Active

    $689,000

    4 bd · 3 ba · 2,402 sqft

    180 Paradise Ridge Rd, Oakland, MD

    Brian P Homberg · Taylor-Made Deep Creek Sales

  12. 1131 Lake Shore Dr — photo124Active

    $3,950,000

    8 bd · 10 ba · 6,486 sqft

    1131 Lake Shore Dr, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  13. 565 Glendale Rd #213 — photoPrice Reduced23Active

    $200,000

    1 bd · 1 ba · 0 sqft

    565 Glendale Rd #213, Oakland, MD

    Charlotte Savoy · The KW Collective

  14. 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

  15. 181 Glotfelty Dr — photoPrice Reduced51Active

    $374,900

    3 bd · 2 ba · 1,456 sqft

    181 Glotfelty Dr, Oakland, MD

    Kathy L Gibson · Railey Realty, Inc.

  16. 325 Markwood Dr — photoPrice Reduced66Active

    $769,000

    4 bd · 4 ba · 3,376 sqft

    325 Markwood Dr, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  17. 15 Byran Dr — photo60Active

    $799,900

    4 bd · 4 ba · 0 sqft

    15 Byran Dr, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  18. 5 Laurel Brook Dr #5 — photoPrice Reduced29Active

    $259,900

    2 bd · 2 ba · 1,400 sqft

    5 Laurel Brook Dr #5, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  19. 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

  20. 206 W Liberty St — photoPrice Reduced35Active

    $129,000

    2 bd · 1 ba · 2,008 sqft

    206 W Liberty St, Oakland, MD

    Nicole Jackson · Railey Realty, Inc.

  21. 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.

  22. 102 N 3rd St — photo43Active

    $259,900

    3 bd · 2 ba · 1,998 sqft

    102 N 3rd St, Oakland, MD

    Kevin D Liller · Railey Realty, Inc.

  23. 826 G Swauger Rd — photoPrice Reduced33Active

    $1,095,000

    2 bd · 3 ba · 2,914 sqft

    826 G Swauger Rd, Oakland, MD

    Larry E. Roth · Railey Realty, Inc.

  24. 941 Mountainview Dr — photoPrice Reduced60Active

    $719,999

    4 bd · 4 ba · 4,377 sqft

    941 Mountainview Dr, Oakland, MD

    Nicole Jackson · Railey Realty, Inc.

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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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Listing data & MLS disclosures

Bright MLS
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: 2026-10-31 16:34:13 UTC
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    Nearby areas

    ZIP codes

    • 21550 (91)
    • 21541 (86)
    • 21561 (37)
    • 21562 (14)
    • 21531 (9)
    • 21536 (7)
    • 21539 (6)
    • 21520 (5)

    Cities

    • Mc Henry (86)
    • Swanton (37)
    • Westernport (12)
    • Friendsville (9)
    • Grantsville (6)
    • Lonaconing (6)
    • Accident (5)
    • Barton (5)

    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.