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Oakland, MD Homes for Sale — Page 3 | Realty.com
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Homes for Sale in Oakland, MD

Homes for Sale in Oakland, MD

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24 of 82 Listings
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Homes for Sale in Oakland, MD

24 of 82 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 20160 Garrett Hwy #C307 — photo49Active

    $379,500

    1 bd · 1 ba · 636 sqft

    20160 Garrett Hwy #C307, Oakland, MD

    Justin D Liller · Railey Realty, Inc.

  2. 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.

  3. 122 Woodlands Hill Ln — photoPrice Reduced59Active

    $1,089,000

    4 bd · 5 ba · 2,656 sqft

    122 Woodlands Hill Ln, Oakland, MD

    Brian P Homberg · Taylor-Made Deep Creek Sales

  4. 1499 Foster Rd — photoPrice Reduced64Active

    $375,000

    4 bd · 2 ba · 2,234 sqft

    1499 Foster Rd, Oakland, MD

    Kelsey Lynn Meyers · Railey Realty, Inc.

  5. 560 Glendale Rd — photoPrice Reduced24Active

    $374,900

    2 bd · 1 ba · 700 sqft

    560 Glendale Rd, Oakland, MD

    Lauren McCann · Railey Realty, Inc.

  6. 20160 Garrett Hwy #H706 — photoPrice Reduced27Active

    $299,000

    1 bd · 1 ba · 550 sqft

    20160 Garrett Hwy #H706, Oakland, MD

    James Calvin Matthews · Taylor-Made Deep Creek Sales

  7. 127 Paradise Hts — photoPrice Reduced24Active

    $999,999

    3 bd · 3 ba · 2,240 sqft

    127 Paradise Hts, Oakland, MD

    Norman S Domingo · XRealty.NET LLC

  8. 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

  9. 251 Robinwood Dr — photoPrice Reduced63Active

    $899,900

    5 bd · 5 ba · 4,284 sqft

    251 Robinwood Dr, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  10. 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

  11. 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

  12. 83 Bethlehem Rd — photo43Active

    $2,499,900

    4 bd · 2 ba · 2,190 sqft

    83 Bethlehem Rd, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  13. 206 Mayhew Inn Rd — photo31Active

    $224,900

    1 bd · 1 ba · 0 sqft

    206 Mayhew Inn Rd, Oakland, MD

    Thomas Jay Quinn · Taylor-Made Deep Creek Sales

  14. 827 Penn Point Rd — photo64Active

    $1,400,000

    5 bd · 4 ba · 2,832 sqft

    827 Penn Point Rd, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  15. 565 Glendale Rd #306 — photoPrice Reduced32Active

    $229,900

    2 bd · 1 ba · 772 sqft

    565 Glendale Rd #306, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  16. 135 Jeffrey Ln #19a — photo22Active

    $294,999

    2 bd · 1 ba · 2,344 sqft

    135 Jeffrey Ln #19a, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  17. 400 Bear Dr E — photoPrice Reduced42Active

    $235,000

    2 bd · 2 ba · 560 sqft

    400 Bear Dr E, Oakland, MD

    Danielle Luscombe · Taylor-Made Deep Creek Sales

  18. 565 Glendale Rd #125 — photo55Active

    $329,900

    1 bd · 1 ba · 496 sqft

    565 Glendale Rd #125, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  19. 1167 Tall Oaks Dr — photoPrice Reduced59Active

    $349,000

    2 bd · 3 ba · 1,920 sqft

    1167 Tall Oaks Dr, Oakland, MD

    Coelian M Green · Railey Realty, Inc.

  20. 113 Jubb Meadows Ln — photoPrice Reduced69Active

    $869,900

    4 bd · 4 ba · 3,185 sqft

    113 Jubb Meadows Ln, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  21. 163 Mitchell Dr — photoPrice Reduced65Active

    $279,000

    3 bd · 3 ba · 2,242 sqft

    163 Mitchell Dr, Oakland, MD

    Andrew L Eiswert · Railey Realty, Inc.

  22. 164 Grandview Dr — photoPrice Reduced53Active

    $849,900

    3 bd · 3 ba · 2,368 sqft

    164 Grandview Dr, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  23. 141 Montana Ln — photo57Active

    $219,000

    1 bd · 2 ba · 912 sqft

    141 Montana Ln, Oakland, MD

    Larry E Smith · Railey Realty, Inc.

  24. 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.

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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: 2026-10-07 01:47:43 UTC
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    Nearby areas

    ZIP codes

    • 21550 (85)
    • 21541 (76)
    • 21561 (41)
    • 21562 (15)
    • 21536 (9)
    • 21539 (9)
    • 21531 (8)
    • 21520 (7)

    Cities

    • Mc Henry (74)
    • Swanton (41)
    • Westernport (14)
    • Grantsville (9)
    • Lonaconing (9)
    • Friendsville (8)
    • Accident (7)
    • 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

    September 2026

    Oakland 12-month median sale price trend

    Selling at 96.5% of asking price

    Buyers here are paying below asking. MLS · 21 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 18, 2026

    Median sale price
    $318,500$115,000–$520,000 typical range
    Price per sq. ft.
    $192
    Sales
    29
    Paid in cash
    44.8%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $454,500
    Homes for sale
    78
    Median days on market
    53 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    64.3%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

    Median home size
    1,536 sq. ft.