10,714

Oakland, MD Homes

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  • 202 Penelacre Ln, Oakland, MD 21550
    202 Penelacre Ln, Oakland, MD 21550
    202 Penelacre Ln, Oakland, MD 21550
    /85

    $975,000 Sold Nov 24, 2025

    202 Penelacre Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • Built 1985

    Last Sold Summary

    • $592/SF
    • 12 Days On Market

    Last Listing Agent Justin Liller Railey Realty, Inc.

    202 Penelacre Ln, Oakland, MD 21550
    • 512 Roanoke Ave, Oakland, MD 21550
      512 Roanoke Ave, Oakland, MD 21550
      512 Roanoke Ave, Oakland, MD 21550
      /25

      Est $143,682 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft

      512 Roanoke Ave, Oakland, MD 21550

      512 Roanoke Ave, Oakland, MD 21550
  • 870 Holy Cross Dr, Oakland, MD 21550
    870 Holy Cross Dr, Oakland, MD 21550
    870 Holy Cross Dr, Oakland, MD 21550
    /93

    $3,375,000 Sold Nov 13, 2025

    870 Holy Cross Dr, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 5,681 Sq Ft
    • Built 2007

    Last Sold Summary

    • $594/SF
    • 5 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    870 Holy Cross Dr, Oakland, MD 21550
    • 204 D St, Oakland, MD 21550
      204 D St, Oakland, MD 21550
      204 D St, Oakland, MD 21550
      /19

      Est $154,522 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft

      204 D St, Oakland, MD 21550

      204 D St, Oakland, MD 21550
  • 5 Warnick Way, Oakland, MD 21550
    5 Warnick Way, Oakland, MD 21550
    5 Warnick Way, Oakland, MD 21550
    /10

    $30,000 Sold Apr 21, 2025

    5 Warnick Way, Oakland, MD 21550

    • Land
    • 0.84 Acre
    • $35,714 per Acre

    Last Sold Summary

    • 590 Days On Market

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    5 Warnick Way, Oakland, MD 21550
    • 132 Hillside Dr, Oakland, MD 21550
      132 Hillside Dr, Oakland, MD 21550
      132 Hillside Dr, Oakland, MD 21550
      /61

      Est $267,003 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,488 Sq Ft

      132 Hillside Dr, Oakland, MD 21550

      132 Hillside Dr, Oakland, MD 21550
  • 4012 Maryland Hwy, Oakland, MD 21550
    4012 Maryland Hwy, Oakland, MD 21550
    4012 Maryland Hwy, Oakland, MD 21550
    /55

    $280,000 Sold Jul 31, 2025

    4012 Maryland Hwy, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,824 Sq Ft
    • Built 1968

    Last Sold Summary

    • $154/SF
    • 32 Days On Market

    Current Estimated Value $280,152

    Last Listing Agent Michael Fenton Railey Realty, Inc.

    4012 Maryland Hwy, Oakland, MD 21550
    • 1306 Wheeling Ave, Oakland, MD 21550
      1306 Wheeling Ave, Oakland, MD 21550
      1306 Wheeling Ave, Oakland, MD 21550
      /22

      Est $273,175 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,624 Sq Ft

      1306 Wheeling Ave, Oakland, MD 21550

      1306 Wheeling Ave, Oakland, MD 21550
  • 4.00 Acres Moose Crossing, Oakland, MD 21550
    4.00 Acres Moose Crossing, Oakland, MD 21550
    4.00 Acres Moose Crossing, Oakland, MD 21550
    /18

    $75,000 Sold Sep 25, 2025

    4.00 Acres Moose Crossing, Oakland, MD 21550

    • Land
    • 4 Acres
    • $18,750 per Acre

    Last Sold Summary

    • 27 Days On Market

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    4.00 Acres Moose Crossing, Oakland, MD 21550
    • 410 K St, Oakland, MD 21550
      410 K St, Oakland, MD 21550
      410 K St, Oakland, MD 21550
      /21

      Est $129,098 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,440 Sq Ft

      410 K St, Oakland, MD 21550

      410 K St, Oakland, MD 21550
  • 0 Lot#2 Farmview Ln, Oakland, MD 21550
    0 Lot#2 Farmview Ln, Oakland, MD 21550
    0 Lot#2 Farmview Ln, Oakland, MD 21550
    /17

    $28,000 Sold Feb 28, 2025

    0 Lot#2 Farmview Ln, Oakland, MD 21550

    • Land
    • 0.95 Acre
    • $29,474 per Acre

    Last Sold Summary

    • 192 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    0 Lot#2 Farmview Ln, Oakland, MD 21550
    • 1100 Oakland Ave, Oakland, MD 21550
      1100 Oakland Ave, Oakland, MD 21550
      1100 Oakland Ave, Oakland, MD 21550
      /25

      Est $192,836 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 1,920 Sq Ft

      1100 Oakland Ave, Oakland, MD 21550

      1100 Oakland Ave, Oakland, MD 21550
  • 16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    /70

    $555,000 Sold Nov 20, 2025

    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft
    • Built 2009

    Last Sold Summary

    • $206/SF
    • 68 Days On Market

    Last Listing Agent Justin Liller Railey Realty, Inc.

    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    • 1107 Oakland Ave, Oakland, MD 21550
      1107 Oakland Ave, Oakland, MD 21550
      1107 Oakland Ave, Oakland, MD 21550
      /42

      Est $162,556 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,152 Sq Ft

      1107 Oakland Ave, Oakland, MD 21550

      1107 Oakland Ave, Oakland, MD 21550
  • 3941 Pleasant Valley Rd, Oakland, MD 21550
    3941 Pleasant Valley Rd, Oakland, MD 21550
    3941 Pleasant Valley Rd, Oakland, MD 21550
    /46

    $110,000 Sold Apr 04, 2025

    3941 Pleasant Valley Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,060 Sq Ft
    • Built 1900

    Last Sold Summary

    • $53/SF
    • 82 Days On Market

    Current Estimated Value $141,445

    Last Listing Agent Ben Maust Railey Realty, Inc.

    3941 Pleasant Valley Rd, Oakland, MD 21550
    • 13 Hazel Glade Dr, Oakland, MD 21550
      13 Hazel Glade Dr, Oakland, MD 21550
      13 Hazel Glade Dr, Oakland, MD 21550
      /64

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft

      13 Hazel Glade Dr, Oakland, MD 21550

      13 Hazel Glade Dr, Oakland, MD 21550
  • 206 N 10th St, Oakland, MD 21550
    206 N 10th St, Oakland, MD 21550
    206 N 10th St, Oakland, MD 21550
    /103

    $320,000 Sold Jul 18, 2025

    206 N 10th St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,772 Sq Ft
    • Built 1972

    Last Sold Summary

    • $115/SF
    • 37 Days On Market

    Current Estimated Value $332,277

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    206 N 10th St, Oakland, MD 21550
    • 318 Allegheny Dr, Oakland, MD 21550
      318 Allegheny Dr, Oakland, MD 21550
      318 Allegheny Dr, Oakland, MD 21550
      /47

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft

      318 Allegheny Dr, Oakland, MD 21550

      318 Allegheny Dr, Oakland, MD 21550
  • 111 Tarn Dr, Oakland, MD 21550
    111 Tarn Dr, Oakland, MD 21550
    111 Tarn Dr, Oakland, MD 21550
    /20

    $40,000 Sold Oct 20, 2025

    111 Tarn Dr, Oakland, MD 21550

    • Land
    • 1 Acre
    • $40,000 per Acre

    Last Sold Summary

    • 260 Days On Market

    Last Listing Agent Amy Grubby AEK Real Estate, LLC

    111 Tarn Dr, Oakland, MD 21550
    • 700 I St, Oakland, MD 21550
      700 I St, Oakland, MD 21550
      700 I St, Oakland, MD 21550
      /48

      Est $169,535 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,168 Sq Ft

      700 I St, Oakland, MD 21550

      700 I St, Oakland, MD 21550
  • 20241 Garrett Hwy Unit 5, Oakland, MD 21550
    20241 Garrett Hwy Unit 5, Oakland, MD 21550
    20241 Garrett Hwy Unit 5, Oakland, MD 21550
    /47

    $407,000 Sold Apr 18, 2025

    20241 Garrett Hwy Unit 5, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,330 Sq Ft
    • Built 1989

    Last Sold Summary

    • $175/SF
    • 9 Days On Market

    Current Estimated Value $421,266

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    20241 Garrett Hwy Unit 5, Oakland, MD 21550
    • 409 M St, Oakland, MD 21550
      409 M St, Oakland, MD 21550
      409 M St, Oakland, MD 21550
      /29

      Est $186,508 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,208 Sq Ft

      409 M St, Oakland, MD 21550

      409 M St, Oakland, MD 21550
  • 230 Moose Crossing, Oakland, MD 21550
    230 Moose Crossing, Oakland, MD 21550
    230 Moose Crossing, Oakland, MD 21550
    /100

    $455,000 Sold Mar 28, 2025

    230 Moose Crossing, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,441 Sq Ft
    • Built 1980

    Last Sold Summary

    • $186/SF
    • 115 Days On Market

    Current Estimated Value $457,537

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    230 Moose Crossing, Oakland, MD 21550
    • 513 K St, Oakland, MD 21550
      513 K St, Oakland, MD 21550
      513 K St, Oakland, MD 21550
      /36

      Est $85,091 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,404 Sq Ft

      513 K St, Oakland, MD 21550

      513 K St, Oakland, MD 21550
  • 465 Pergin Farm Rd, Oakland, MD 21550
    465 Pergin Farm Rd, Oakland, MD 21550
    465 Pergin Farm Rd, Oakland, MD 21550
    /79

    $735,000 Sold Dec 18, 2025

    465 Pergin Farm Rd, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,960 Sq Ft
    • Built 2006

    Last Sold Summary

    • $248/SF
    • 9 Days On Market

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    465 Pergin Farm Rd, Oakland, MD 21550
    • 1107 Broadford Rd, Oakland, MD 21550
      1107 Broadford Rd, Oakland, MD 21550
      1107 Broadford Rd, Oakland, MD 21550
      /5

      Est $256,739 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,568 Sq Ft

      1107 Broadford Rd, Oakland, MD 21550

      1107 Broadford Rd, Oakland, MD 21550
  • p/o parcel 206 G Swauger Rd, Oakland, MD 21550
    p/o parcel 206 G Swauger Rd, Oakland, MD 21550
    p/o parcel 206 G Swauger Rd, Oakland, MD 21550
    /4

    $61,125 Sold Jun 25, 2025

    p/o parcel 206 G Swauger Rd, Oakland, MD 21550

    • Land
    • 6.75 Acres
    • $9,056 per Acre

    Last Sold Summary

    Last Listing Agent Rich Orr Railey Realty, Inc.

    p/o parcel 206 G Swauger Rd, Oakland, MD 21550
    • 505 Shenandoah Ave, Oakland, MD 21550
      505 Shenandoah Ave, Oakland, MD 21550
      505 Shenandoah Ave, Oakland, MD 21550
      /23

      Est $151,794 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,632 Sq Ft

      505 Shenandoah Ave, Oakland, MD 21550

      505 Shenandoah Ave, Oakland, MD 21550
  • TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550
    TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550
    TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550
    /10

    $414,100 Sold Jan 20, 2025

    TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550

    • Land
    • 51.31 Acres
    • $8,071 per Acre

    Last Sold Summary

    • 42 Days On Market

    Last Listing Agent Kaleb Hurley Hurley Real Estate & Auctions

    TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550
    • 113 Jubb Meadows Ln, Oakland, MD 21550
      113 Jubb Meadows Ln, Oakland, MD 21550
      113 Jubb Meadows Ln, Oakland, MD 21550
      /95

      Est $897,153 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,185 Sq Ft

      113 Jubb Meadows Ln, Oakland, MD 21550

      113 Jubb Meadows Ln, Oakland, MD 21550
  • 408 Shenandoah Ave, Oakland, MD 21550
    408 Shenandoah Ave, Oakland, MD 21550
    408 Shenandoah Ave, Oakland, MD 21550
    /43

    $110,000 Sold Jul 16, 2025

    408 Shenandoah Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1950

    Last Sold Summary

    • $115/SF
    • 2 Days On Market

    Current Estimated Value $112,559

    Last Listing Agent Rich Orr Railey Realty, Inc.

    408 Shenandoah Ave, Oakland, MD 21550
    • 932 Underwood Rd, Oakland, MD 21550
      932 Underwood Rd, Oakland, MD 21550
      932 Underwood Rd, Oakland, MD 21550
      /80

      Est $338,781 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,340 Sq Ft

      932 Underwood Rd, Oakland, MD 21550

      932 Underwood Rd, Oakland, MD 21550
  • 19956 Garrett Hwy Unit 2, Oakland, MD 21550
    19956 Garrett Hwy Unit 2, Oakland, MD 21550
    19956 Garrett Hwy Unit 2, Oakland, MD 21550
    /57

    $1,200,000 Sold Jun 13, 2025

    19956 Garrett Hwy Unit 2, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 3,012 Sq Ft
    • Built 2007

    Last Sold Summary

    • $398/SF
    • 5 Days On Market

    Current Estimated Value $1,195,953

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    19956 Garrett Hwy Unit 2, Oakland, MD 21550
    • 242 Interlude Ln, Oakland, MD 21550
      242 Interlude Ln, Oakland, MD 21550
      242 Interlude Ln, Oakland, MD 21550
      /10

      Est $293,581 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,544 Sq Ft

      242 Interlude Ln, Oakland, MD 21550

      242 Interlude Ln, Oakland, MD 21550
  • 88 Knoll Crest Heights Dr, Oakland, MD 21550
    88 Knoll Crest Heights Dr, Oakland, MD 21550
    88 Knoll Crest Heights Dr, Oakland, MD 21550
    /38

    $225,000 Sold Oct 16, 2025

    88 Knoll Crest Heights Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,867 Sq Ft
    • Built 1974

    Last Sold Summary

    • $121/SF
    • 31 Days On Market

    Last Listing Agent Justin Liller Railey Realty, Inc.

    88 Knoll Crest Heights Dr, Oakland, MD 21550
    • 2078 Sanders Ln, Oakland, MD 21550
      2078 Sanders Ln, Oakland, MD 21550
      2078 Sanders Ln, Oakland, MD 21550
      /85

      Est $459,467 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,904 Sq Ft

      2078 Sanders Ln, Oakland, MD 21550

      2078 Sanders Ln, Oakland, MD 21550
  • 22 Black Oak Dr, Oakland, MD 21550
    22 Black Oak Dr, Oakland, MD 21550
    22 Black Oak Dr, Oakland, MD 21550
    /29

    $220,000 Sold May 30, 2025

    22 Black Oak Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1998

    Last Sold Summary

    • $170/SF
    • 16 Days On Market

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Vacations & Sales

    22 Black Oak Dr, Oakland, MD 21550
    • 181 Glotfelty Dr, Oakland, MD 21550
      181 Glotfelty Dr, Oakland, MD 21550
      181 Glotfelty Dr, Oakland, MD 21550
      /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft

      181 Glotfelty Dr, Oakland, MD 21550

      181 Glotfelty Dr, Oakland, MD 21550
  • 10178 Garrett Hwy, Oakland, MD 21550
    10178 Garrett Hwy, Oakland, MD 21550
    10178 Garrett Hwy, Oakland, MD 21550
    /12

    $86,000 Sold Apr 17, 2025

    10178 Garrett Hwy, Oakland, MD 21550

    • Land
    • 3.04 Acres
    • $28,289 per Acre

    Last Sold Summary

    • 7 Days On Market

    Current Estimated Value $90,796

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    10178 Garrett Hwy, Oakland, MD 21550
    • 367 Underwood Rd, Oakland, MD 21550
      367 Underwood Rd, Oakland, MD 21550
      367 Underwood Rd, Oakland, MD 21550
      /56

      Est $244,548 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,400 Sq Ft

      367 Underwood Rd, Oakland, MD 21550

      367 Underwood Rd, Oakland, MD 21550

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