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Oakland, MD Homes for Sale — Page 3 | 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. 321 N 3rd St — photoPrice Reduced48Active

    $365,000

    5 bd · 2 ba · 3,660 sqft

    321 N 3rd St, Oakland, MD

    Christina M Ford · CENTURY 21 New Millennium

  2. 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

  3. 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

  4. 638 Glendale Rd — photo56Active

    $745,000

    5 bd · 3 ba · 2,640 sqft

    638 Glendale Rd, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  5. 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.

  6. 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

  7. 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

  8. 565 Glendale Rd #306 — photo32Active

    $249,900

    2 bd · 1 ba · 772 sqft

    565 Glendale Rd #306, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  9. 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

  10. 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

  11. 13 Laurel Brook Dr #13 — photo42Active

    $259,500

    2 bd · 2 ba · 1,320 sqft

    13 Laurel Brook Dr #13, Oakland, MD

    Bill G Weissgerber Jr. · Railey Realty, Inc.

  12. 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.

  13. 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.

  14. 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.

  15. 163 Mitchell Dr — photoPrice Reduced62Active

    $279,000

    3 bd · 3 ba · 2,242 sqft

    163 Mitchell Dr, Oakland, MD

    Andrew L Eiswert · Railey Realty, Inc.

  16. 449 S 3rd St — photo64Active

    $275,900

    4 bd · 2 ba · 1,928 sqft

    449 S 3rd St, Oakland, MD

    Justin D Liller · Railey Realty, Inc.

  17. 164 Grandview Dr — photoPrice Reduced53Active

    $912,000

    3 bd · 3 ba · 2,368 sqft

    164 Grandview Dr, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  18. 141 Montana Ln — photo57Active

    $219,000

    1 bd · 2 ba · 912 sqft

    141 Montana Ln, Oakland, MD

    Larry E Smith · Railey Realty, Inc.

  19. 660 Glendale Rd — photoPrice Reduced62Active

    $999,000

    5 bd · 3 ba · 2,592 sqft

    660 Glendale Rd, Oakland, MD

    Nick Fratz-Orr · Railey Realty, Inc.

  20. 231 Santa Fe Trl — photo38Active

    $629,000

    4 bd · 3 ba · 2,280 sqft

    231 Santa Fe Trl, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  21. 157 Jeffrey Ln #21B — photoPrice Reduced29Active

    $294,000

    2 bd · 1 ba · 550 sqft

    157 Jeffrey Ln #21B, Oakland, MD

    James Calvin Matthews · Taylor-Made Deep Creek Sales

  22. 467 Paradise Ridge Rd — photoPrice Reduced64Active

    $769,900

    4 bd · 4 ba · 3,780 sqft

    467 Paradise Ridge Rd, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  23. 52 Dam View Dr — photoPrice Reduced97Active

    $1,059,900

    4 bd · 6 ba · 3,032 sqft

    52 Dam View Dr, Oakland, MD

    Michael Fenton · Railey Realty, Inc.

  24. 62 Wild Turkey Ct — photo30Active

    $249,000

    4 bd · 3 ba · 2,390 sqft

    62 Wild Turkey Ct, Oakland, MD

    Melvin E Smith Jr. · 1 Real Estate Source LLC

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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

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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: 2026-09-17 15:03:14 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 (40)
    • 21562 (15)
    • 21536 (12)
    • 21531 (8)
    • 21539 (7)
    • 21520 (5)

    Cities

    • Mc Henry (73)
    • Swanton (40)
    • Westernport (15)
    • Grantsville (12)
    • Friendsville (8)
    • Lonaconing (7)
    • Accident (5)
    • Barton (5)