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Oakland, MD Homes for Sale | Realty.com
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3 beds
83 listings
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New construction
With a pool

Homes for Sale in Oakland, MD

Homes for Sale in Oakland, MD

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24 of 83 Listings
Map

Homes for Sale in Oakland, MD

24 of 83 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 870 Hunters Ridge Dr — photo65Active

    $699,000

    4 bd · 3 ba · 2,896 sqft

    870 Hunters Ridge Dr, Oakland, MD

    Justin D Liller · Railey Realty, Inc.

  2. 565 Glendale Rd #316 — photo26Active

    $279,000

    2 bd · 1 ba · 772 sqft

    565 Glendale Rd #316, Oakland, MD

    Brent Daniel Housley · Railey Realty, Inc.

  3. 127 Jeffrey Ln #4 — photo49Active

    $279,000

    2 bd · 1 ba · 700 sqft

    127 Jeffrey Ln #4, Oakland, MD

    Kathy L Gibson · Railey Realty, Inc.

  4. 1959 Birchwood Dr — photo36Active

    $235,000

    2 bd · 2 ba · 1,152 sqft

    1959 Birchwood Dr, Oakland, MD

    Laura C Newhall · Taylor-Made Deep Creek Sales

  5. 1529 Paradise Point Rd — photo67Active

    $639,000

    3 bd · 3 ba · 1,933 sqft

    1529 Paradise Point Rd, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  6. 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.

  7. 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

  8. 20160 Garett Hwy #105a — photo25Active

    $296,500

    1 bd · 1 ba · 600 sqft

    20160 Garett Hwy #105a, Oakland, MD

    Richard B Orr · Railey Realty, Inc.

  9. 102 Roanoke Ave — photoPrice Reduced38Active

    $69,990

    3 bd · 1 ba · 1,932 sqft

    102 Roanoke Ave, Oakland, MD

    Heidi J Heiderman · Samson Properties

  10. 586 Bray School Rd — photo32Active

    $289,000

    4 bd · 2 ba · 2,240 sqft

    586 Bray School Rd, Oakland, MD

    Julia Mead · The KW Collective

  11. 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

  12. 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.

  13. 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.

  14. 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

  15. 184 Upper Penn Point Dr — photoPrice Reduced53Active

    $895,000

    3 bd · 2 ba · 1,152 sqft

    184 Upper Penn Point Dr, Oakland, MD

    Amy Webster Mangum · Railey Realty, Inc.

  16. 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

  17. 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.

  18. 18948 Garrett Hwy — photo41Active

    $375,000

    2 bd · 2 ba · 1,404 sqft

    18948 Garrett Hwy, Oakland, MD

    Daniel Patrick Duggan Sr. · 1 Real Estate Source LLC

  19. 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

  20. 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

  21. 565 Glendale Rd #213 — photoPrice Reduced24Active

    $215,000

    1 bd · 1 ba · 0 sqft

    565 Glendale Rd #213, Oakland, MD

    Charlotte Savoy · The KW Collective

  22. 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

  23. 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.

  24. 15 Byran Dr — photo60Active

    $799,900

    4 bd · 4 ba · 0 sqft

    15 Byran Dr, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

12…4

Explore Oakland homes

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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: 2026-09-26 13:50:47 UTC
    • New construction
    • With a pool

    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

    August 2026

    Oakland 12-month median sale price trend

    Selling at 95.5% of asking price

    Buyers here are paying below asking. MLS · 21 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 27, 2026

    Median sale price
    $289,250$116,000–$684,250 typical range
    Price per sq. ft.
    $281
    Sales
    26
    Paid in cash
    46.2%

    Homes on the market · MLS, as of Aug 31, 2026

    Median list price
    $464,900
    Homes for sale
    81
    Median days on market
    30 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    41.5%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,536 sq. ft.

    Nearby areas

    ZIP codes

    • 21550 (88)
    • 21541 (75)
    • 21561 (41)
    • 21562 (16)
    • 21536 (10)
    • 21539 (9)
    • 21531 (8)
    • 21521 (5)

    Cities

    • Mc Henry (74)
    • Swanton (41)
    • Westernport (15)
    • Grantsville (10)
    • Lonaconing (9)
    • Friendsville (8)
    • Barton (5)
    • Frostburg (5)