10,731

Oakland, MD Homes

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    • 26 Paradise Ridge Rd, Oakland, MD 21550
      26 Paradise Ridge Rd, Oakland, MD 21550
      26 Paradise Ridge Rd, Oakland, MD 21550
      /63

      Est $564,251 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,104 Sq Ft

      26 Paradise Ridge Rd, Oakland, MD 21550

      26 Paradise Ridge Rd, Oakland, MD 21550
  • 1056 Sunrise Dr, Oakland, MD 21550
    1056 Sunrise Dr, Oakland, MD 21550
    1056 Sunrise Dr, Oakland, MD 21550
    /60

    $280,000 Sold Nov 14, 2025

    1056 Sunrise Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 1,528 Sq Ft
    • Built 1976

    Last Sold Summary

    • $183/SF
    • 59 Days On Market

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

    1056 Sunrise Dr, Oakland, MD 21550
    • 187 Lower Penn Point Dr, Oakland, MD 21550
      187 Lower Penn Point Dr, Oakland, MD 21550
      187 Lower Penn Point Dr, Oakland, MD 21550
      /30

      Est $1,196,195 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      187 Lower Penn Point Dr, Oakland, MD 21550

      187 Lower Penn Point Dr, Oakland, MD 21550
  • 26 Arrowhead Ln, Oakland, MD 21550
    26 Arrowhead Ln, Oakland, MD 21550
    26 Arrowhead Ln, Oakland, MD 21550
    /42

    $675,000 Sold Mar 14, 2025

    26 Arrowhead Ln, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,000 Sq Ft
    • Built 1988

    Last Sold Summary

    • $338/SF
    • 389 Days On Market

    Current Estimated Value $693,442

    Last Listing Agent Kellyann Green Railey Realty, Inc.

    26 Arrowhead Ln, Oakland, MD 21550
    • 156 Sunrise Point Ln, Oakland, MD 21550
      156 Sunrise Point Ln, Oakland, MD 21550
      156 Sunrise Point Ln, Oakland, MD 21550
      /35

      Est $1,621,345 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft

      156 Sunrise Point Ln, Oakland, MD 21550

      156 Sunrise Point Ln, Oakland, MD 21550
  • Lot #5 Swan Meadow Dr, Oakland, MD 21550
    Lot #5 Swan Meadow Dr, Oakland, MD 21550
    Lot #5 Swan Meadow Dr, Oakland, MD 21550
    /5

    $135,000 Sold Jun 25, 2025

    Lot #5 Swan Meadow Dr, Oakland, MD 21550

    • Land
    • 10 Acres
    • $13,500 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    Lot #5 Swan Meadow Dr, Oakland, MD 21550
    • 91 Mallard Loop, Oakland, MD 21550
      91 Mallard Loop, Oakland, MD 21550
      91 Mallard Loop, Oakland, MD 21550
      /48

      Est $798,073 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,508 Sq Ft

      91 Mallard Loop, Oakland, MD 21550

      91 Mallard Loop, Oakland, MD 21550
  • 1087 Pergin Farm Rd, Oakland, MD 21550
    1087 Pergin Farm Rd, Oakland, MD 21550
    1087 Pergin Farm Rd, Oakland, MD 21550
    /149

    $2,975,000 Sold Oct 03, 2025

    1087 Pergin Farm Rd, Oakland, MD 21550

    • 6 Beds
    • 5.5 Baths
    • 4,481 Sq Ft
    • Built 1984

    Last Sold Summary

    • $664/SF
    • 16 Days On Market

    Current Estimated Value $2,965,827

    Last Listing Agent Susan Bell Railey Realty, Inc.

    1087 Pergin Farm Rd, Oakland, MD 21550
    • 1356 Stockslager Rd, Oakland, MD 21550
      1356 Stockslager Rd, Oakland, MD 21550
      1356 Stockslager Rd, Oakland, MD 21550
      /63

      Est $1,766,480 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,070 Sq Ft

      1356 Stockslager Rd, Oakland, MD 21550

      1356 Stockslager Rd, Oakland, MD 21550
  • Lot 9 Birchwood Dr, Oakland, MD 21550
    Lot 9 Birchwood Dr, Oakland, MD 21550
    Lot 9 Birchwood Dr, Oakland, MD 21550
    /23

    $18,000 Sold Jul 03, 2025

    Lot 9 Birchwood Dr, Oakland, MD 21550

    • Land
    • 0.8 Acre
    • $22,500 per Acre

    Last Sold Summary

    • 5 Days On Market

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

    Lot 9 Birchwood Dr, Oakland, MD 21550
    • 1174 Stockslager Rd, Oakland, MD 21550
      1174 Stockslager Rd, Oakland, MD 21550
      1174 Stockslager Rd, Oakland, MD 21550
      /108

      Est $1,870,002 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,616 Sq Ft

      1174 Stockslager Rd, Oakland, MD 21550

      1174 Stockslager Rd, Oakland, MD 21550
  • 30 Village Dr Unit 3, Oakland, MD 21550
    30 Village Dr Unit 3, Oakland, MD 21550
    30 Village Dr Unit 3, Oakland, MD 21550
    /35

    $390,000 Sold Dec 12, 2025

    30 Village Dr Unit 3, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 916 Sq Ft
    • Built 2005

    Last Sold Summary

    • $426/SF
    • 34 Days On Market

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    30 Village Dr Unit 3, Oakland, MD 21550
    • 470 W Liberty St, Oakland, MD 21550
      470 W Liberty St, Oakland, MD 21550
      470 W Liberty St, Oakland, MD 21550
      /42

      Est $343,545 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,598 Sq Ft

      470 W Liberty St, Oakland, MD 21550

      470 W Liberty St, Oakland, MD 21550
  • 422 Underwood Rd, Oakland, MD 21550
    422 Underwood Rd, Oakland, MD 21550
    422 Underwood Rd, Oakland, MD 21550
    /45

    $195,000 Sold Jul 11, 2025

    422 Underwood Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1972

    Last Sold Summary

    • $203/SF
    • 17 Days On Market

    Current Estimated Value $198,482

    Last Listing Agent Larry Smith Railey Realty, Inc.

    422 Underwood Rd, Oakland, MD 21550
    • 1262 Memorial Dr, Oakland, MD 21550
      1262 Memorial Dr, Oakland, MD 21550
      1262 Memorial Dr, Oakland, MD 21550
      /55

      Est $379,418 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,345 Sq Ft

      1262 Memorial Dr, Oakland, MD 21550

      1262 Memorial Dr, Oakland, MD 21550
  • 2360 Garrett Rd, Oakland, MD 21550
    2360 Garrett Rd, Oakland, MD 21550
    /2

    $285,000 Sold Sep 05, 2025

    2360 Garrett Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Built 2016

    Last Sold Summary

    • $271/SF
    • 0 Days On Market

    Current Estimated Value $290,858

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    2360 Garrett Rd, Oakland, MD 21550
    • 600 S 3rd St, Oakland, MD 21550
      600 S 3rd St, Oakland, MD 21550
      600 S 3rd St, Oakland, MD 21550
      /42

      Est $257,900 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,890 Sq Ft

      600 S 3rd St, Oakland, MD 21550

      600 S 3rd St, Oakland, MD 21550
  • 2805 Shady Dell Rd, Oakland, MD 21550
    2805 Shady Dell Rd, Oakland, MD 21550
    2805 Shady Dell Rd, Oakland, MD 21550
    /47

    $208,550 Sold Sep 26, 2025

    2805 Shady Dell Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1966

    Last Sold Summary

    • $143/SF
    • 42 Days On Market

    Current Estimated Value $221,632

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

    2805 Shady Dell Rd, Oakland, MD 21550
    • 153 N Scott St, Oakland, MD 21550
      153 N Scott St, Oakland, MD 21550
      153 N Scott St, Oakland, MD 21550
      /67

      Est $383,697 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 3,250 Sq Ft

      153 N Scott St, Oakland, MD 21550

      153 N Scott St, Oakland, MD 21550
  • 197 Black Angus Dr, Oakland, MD 21550
    197 Black Angus Dr, Oakland, MD 21550
    197 Black Angus Dr, Oakland, MD 21550
    /111

    $2,600,000 Sold Oct 20, 2025

    197 Black Angus Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,156 Sq Ft
    • Built 1975

    Last Sold Summary

    • $626/SF
    • 15 Days On Market

    Current Estimated Value $2,559,289

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    197 Black Angus Dr, Oakland, MD 21550
    • 305 Crook Crest Rd, Oakland, MD 21550
      305 Crook Crest Rd, Oakland, MD 21550
      305 Crook Crest Rd, Oakland, MD 21550
      /51

      Est $443,491 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,800 Sq Ft

      305 Crook Crest Rd, Oakland, MD 21550

      305 Crook Crest Rd, Oakland, MD 21550
  • 19956 Garrett Hwy Unit 6, Oakland, MD 21550
    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    /81

    $1,200,000 Sold Jan 16, 2026

    19956 Garrett Hwy Unit 6, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 3,000 Sq Ft
    • Built 2007

    Last Sold Summary

    • $400/SF
    • 162 Days On Market

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    • 309 Woodland Dr, Oakland, MD 21550
      309 Woodland Dr, Oakland, MD 21550
      309 Woodland Dr, Oakland, MD 21550
      /56

      Est $295,007 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,184 Sq Ft

      309 Woodland Dr, Oakland, MD 21550

      309 Woodland Dr, Oakland, MD 21550
  • 4 Laurel Brook Dr, Oakland, MD 21550
    4 Laurel Brook Dr, Oakland, MD 21550
    4 Laurel Brook Dr, Oakland, MD 21550
    /22

    $212,000 Sold Dec 05, 2025

    4 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • Built 1989

    Last Sold Summary

    • 166 Days On Market

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Vacations & Sales

    4 Laurel Brook Dr, Oakland, MD 21550
    • 219 W Liberty St, Oakland, MD 21550
      219 W Liberty St, Oakland, MD 21550
      219 W Liberty St, Oakland, MD 21550
      /31

      Est $226,667 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,360 Sq Ft

      219 W Liberty St, Oakland, MD 21550

      219 W Liberty St, Oakland, MD 21550
  • 273 Glendale Rd, Oakland, MD 21550
    273 Glendale Rd, Oakland, MD 21550
    273 Glendale Rd, Oakland, MD 21550
    /74

    $2,450,000 Sold Oct 30, 2025

    273 Glendale Rd, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 5,141 Sq Ft
    • Built 2008

    Last Sold Summary

    • $477/SF
    • 7 Days On Market

    Current Estimated Value $2,478,468

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

    273 Glendale Rd, Oakland, MD 21550
    • 413 N 2nd St, Oakland, MD 21550
      413 N 2nd St, Oakland, MD 21550
      413 N 2nd St, Oakland, MD 21550
      /98

      Est $358,814 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 3,472 Sq Ft

      413 N 2nd St, Oakland, MD 21550

      413 N 2nd St, Oakland, MD 21550
  • 101 Sunset Dr, Oakland, MD 21550
    101 Sunset Dr, Oakland, MD 21550
    101 Sunset Dr, Oakland, MD 21550
    /66

    $499,000 Sold Jul 15, 2025

    101 Sunset Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 3,024 Sq Ft
    • Built 1987

    Last Sold Summary

    • $165/SF
    • 11 Days On Market

    Current Estimated Value $484,234

    Last Listing Agent Rich Orr Railey Realty, Inc.

    101 Sunset Dr, Oakland, MD 21550
    • 708 E Reese St, Oakland, MD 21550
      708 E Reese St, Oakland, MD 21550
      708 E Reese St, Oakland, MD 21550
      /73

      Est $208,639 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,944 Sq Ft

      708 E Reese St, Oakland, MD 21550

      708 E Reese St, Oakland, MD 21550
  • Lot 31 Fawn Dr, Oakland, MD 21550
    Lot 31 Fawn Dr, Oakland, MD 21550
    Lot 31 Fawn Dr, Oakland, MD 21550
    /24

    $17,000 Sold Aug 22, 2025

    Lot 31 Fawn Dr, Oakland, MD 21550

    • Land
    • 0.69 Acre
    • $24,638 per Acre

    Last Sold Summary

    • 19 Days On Market

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

    Lot 31 Fawn Dr, Oakland, MD 21550
    • 132 N 8th St, Oakland, MD 21550
      132 N 8th St, Oakland, MD 21550
      132 N 8th St, Oakland, MD 21550
      /69

      Est $245,454 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,248 Sq Ft

      132 N 8th St, Oakland, MD 21550

      132 N 8th St, Oakland, MD 21550
  • 0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    /4

    $115,000 Sold Sep 26, 2025

    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550

    • Land
    • 0.52 Acre
    • $221,154 per Acre

    Last Sold Summary

    • 32 Days On Market

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    • 514 E Alder St, Oakland, MD 21550
      514 E Alder St, Oakland, MD 21550
      514 E Alder St, Oakland, MD 21550
      /36

      Est $264,659 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,152 Sq Ft

      514 E Alder St, Oakland, MD 21550

      514 E Alder St, Oakland, MD 21550
  • 170 Tannery Rd, Oakland, MD 21550
    170 Tannery Rd, Oakland, MD 21550
    170 Tannery Rd, Oakland, MD 21550
    /28

    $174,500 Sold Oct 30, 2025

    170 Tannery Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft
    • Built 1974

    Last Sold Summary

    • $94/SF
    • 96 Days On Market

    Current Estimated Value $176,086

    Last Listing Agent Jonathan Minerick Homecoin.com

    170 Tannery Rd, Oakland, MD 21550
    • 1400 Wheeling Ave, Oakland, MD 21550
      1400 Wheeling Ave, Oakland, MD 21550
      1400 Wheeling Ave, Oakland, MD 21550
      /21

      Not Listed For Sale

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

      1400 Wheeling Ave, Oakland, MD 21550

      1400 Wheeling Ave, Oakland, MD 21550
  • 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
    • 1405 Wheeling Ave, Oakland, MD 21550
      1405 Wheeling Ave, Oakland, MD 21550
      1405 Wheeling Ave, Oakland, MD 21550
      /67

      Est $218,633 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,530 Sq Ft

      1405 Wheeling Ave, Oakland, MD 21550

      1405 Wheeling Ave, 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
    • 1204 Alexander Ln, Oakland, MD 21550
      1204 Alexander Ln, Oakland, MD 21550
      1204 Alexander Ln, Oakland, MD 21550
      /64

      Est $342,514 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,376 Sq Ft

      1204 Alexander Ln, Oakland, MD 21550

      1204 Alexander Ln, 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

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