10,549

Oakland, MD Homes

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  • 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 $3,129,789

    Last Listing Agent Susan Bell Railey Realty, Inc.

    1087 Pergin Farm Rd, Oakland, MD 21550
    • 3598 Lake Shore Dr, Oakland, MD 21550
      3598 Lake Shore Dr, Oakland, MD 21550
      3598 Lake Shore Dr, Oakland, MD 21550
      /48

      Est $385,972

      Not Listed For Sale

      3598 Lake Shore Dr, Oakland, MD 21550

      • 1 Bed
      • 1.5 Baths
      • 665 Sq Ft
      • Built 1948
      3598 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Kevin Liller Railey Realty, Inc.

  • 62 Whispering Pines Ln, Oakland, MD 21550
    62 Whispering Pines Ln, Oakland, MD 21550
    62 Whispering Pines Ln, Oakland, MD 21550
    /77

    $850,000

    Sold Jul 08, 2026

    62 Whispering Pines Ln, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,464 Sq Ft
    • Built 2025

    Last Sold Summary

    • 9% Below List Price
    • $345/SF
    • 81 Days On Market

    Current Estimated Value $890,333

    Last Listing Agent Justin Liller Railey Realty, Inc.

    62 Whispering Pines Ln, Oakland, MD 21550
    • 3003 Lake Shore Dr, Oakland, MD 21550
      3003 Lake Shore Dr, Oakland, MD 21550
      3003 Lake Shore Dr, Oakland, MD 21550
      /87

      Est $1,231,380

      Not Listed For Sale

      3003 Lake Shore Dr, Oakland, MD 21550

      • 3 Beds
      • 4.5 Baths
      • 1,968 Sq Ft
      • Built 1940
      3003 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 104 Days On Market

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • 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

    Current Estimated Value $385,628

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    30 Village Dr Unit 3, Oakland, MD 21550
    • 2303 Lake Shore Dr, Oakland, MD 21550
      2303 Lake Shore Dr, Oakland, MD 21550
      2303 Lake Shore Dr, Oakland, MD 21550
      /92

      Est $2,775,418

      Not Listed For Sale

      2303 Lake Shore Dr, Oakland, MD 21550

      • 6 Beds
      • 4.5 Baths
      • 5,859 Sq Ft
      • Built 2001
      2303 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 84 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • 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 $306,725

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    2360 Garrett Rd, Oakland, MD 21550
    • 228 Paradise Heights, Oakland, MD 21550
      228 Paradise Heights, Oakland, MD 21550
      228 Paradise Heights, Oakland, MD 21550
      /82

      Est $1,835,000

      Not Listed For Sale

      228 Paradise Heights, Oakland, MD 21550

      • 4 Beds
      • 4.5 Baths
      • 2,249 Sq Ft
      • Built 1989
      228 Paradise Heights, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Jay Quinn Taylor-Made Deep Creek Real Estate, LLC

  • 355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    /70

    $610,000

    Sold May 19, 2026

    355 Lonesome Pine Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 4,720 Sq Ft
    • Built 2010

    Last Sold Summary

    • 16% Above List Price
    • $129/SF
    • 34 Days On Market

    Current Estimated Value $559,930

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    355 Lonesome Pine Rd, Oakland, MD 21550
    • 26 Paradise Ridge Rd, Oakland, MD 21550
      26 Paradise Ridge Rd, Oakland, MD 21550
      26 Paradise Ridge Rd, Oakland, MD 21550
      /63

      Est $527,559

      Not Listed For Sale

      26 Paradise Ridge Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,104 Sq Ft
      • Built 1975
      26 Paradise Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 178 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • 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 $229,964

    Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    2805 Shady Dell Rd, 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 $1,366,922

      Not Listed For Sale

      156 Sunrise Point Ln, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft
      • Built 1950
      156 Sunrise Point Ln, Oakland, MD 21550

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Steven Ritchie Railey Realty, Inc.

  • 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 $2,798,020

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    197 Black Angus Dr, Oakland, MD 21550
    • 91 Mallard Loop, Oakland, MD 21550
      91 Mallard Loop, Oakland, MD 21550
      91 Mallard Loop, Oakland, MD 21550
      /48

      Est $758,190

      Not Listed For Sale

      91 Mallard Loop, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 4,508 Sq Ft
      • Built 1997
      91 Mallard Loop, Oakland, MD 21550

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

  • 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

    Current Estimated Value $1,205,668

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    • 1356 Stockslager Rd, Oakland, MD 21550
      1356 Stockslager Rd, Oakland, MD 21550
      1356 Stockslager Rd, Oakland, MD 21550
      /63

      Est $1,797,337

      Not Listed For Sale

      1356 Stockslager Rd, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 3,070 Sq Ft
      • Built 1997
      1356 Stockslager Rd, Oakland, MD 21550

      Last Sold Summary

      • 229 Days On Market

      Last Listing Agent Steven Ritchie Railey Realty, Inc.

  • 53 Bird Ave, Oakland, MD 21550
    53 Bird Ave, Oakland, MD 21550
    /2

    $220,000

    Sold Jun 16, 2026

    53 Bird Ave, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,104 Sq Ft
    • Built 1980

    Last Sold Summary

    • 8% Below List Price
    • $199/SF
    • 49 Days On Market

    Current Estimated Value $223,180

    Last Listing Agent Rachel Bruch Railey Realty, Inc.

    53 Bird Ave, Oakland, MD 21550
    • 1174 Stockslager Rd, Oakland, MD 21550
      1174 Stockslager Rd, Oakland, MD 21550
      1174 Stockslager Rd, Oakland, MD 21550
      /108

      Est $1,926,033

      Not Listed For Sale

      1174 Stockslager Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 2,616 Sq Ft
      • Built 2011
      1174 Stockslager Rd, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • 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

    Current Estimated Value $216,936

    Last Listing Agent Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    4 Laurel Brook Dr, 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 $330,448

      Not Listed For Sale

      470 W Liberty St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 1,598 Sq Ft
      • Built 2006
      470 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

  • 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 $2,572,123

    Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    273 Glendale Rd, Oakland, MD 21550
    • 1262 Memorial Dr, Oakland, MD 21550
      1262 Memorial Dr, Oakland, MD 21550
      1262 Memorial Dr, Oakland, MD 21550
      /55

      Est $363,775

      Not Listed For Sale

      1262 Memorial Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,345 Sq Ft
      • Built 1992
      1262 Memorial Dr, Oakland, MD 21550

      Last Sold Summary

      • 95 Days On Market

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • 407 Seneca Ave, Oakland, MD 21550
    407 Seneca Ave, Oakland, MD 21550
    407 Seneca Ave, Oakland, MD 21550
    /37

    $217,350

    Sold Jul 20, 2026

    407 Seneca Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft
    • Built 1977

    Last Sold Summary

    • 1% Below List Price
    • $199/SF
    • 62 Days On Market

    Current Estimated Value $214,725

    Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    407 Seneca Ave, 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 $253,554

      Not Listed For Sale

      600 S 3rd St, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,890 Sq Ft
      • Built 1955
      600 S 3rd St, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

  • 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
    • 30,056 Sq Ft
    • $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
    • 600 Hope Ave, Oakland, MD 21550
      600 Hope Ave, Oakland, MD 21550
      600 Hope Ave, Oakland, MD 21550
      /44

      Est $242,055

      Not Listed For Sale

      600 Hope Ave, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 2,480 Sq Ft
      • Built 1981
      600 Hope Ave, Oakland, MD 21550

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

  • 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
    • 22,651 Sq Ft
    • $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
    • 305 Crook Crest Rd, Oakland, MD 21550
      305 Crook Crest Rd, Oakland, MD 21550
      305 Crook Crest Rd, Oakland, MD 21550
      /51

      Est $400,450

      Not Listed For Sale

      305 Crook Crest Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 2,800 Sq Ft
      • Built 1891
      305 Crook Crest Rd, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

  • 0 Longview Ln, Oakland, MD 21550
    0 Longview Ln, Oakland, MD 21550
    0 Longview Ln, Oakland, MD 21550
    /9

    $40,000

    Sold May 29, 2026

    0 Longview Ln, Oakland, MD 21550

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

    Last Sold Summary

    • 219 Days On Market

    Last Listing Agent Linda Deremer Appalachian Realty

    0 Longview Ln, Oakland, MD 21550
    • 309 Woodland Dr, Oakland, MD 21550
      309 Woodland Dr, Oakland, MD 21550
      309 Woodland Dr, Oakland, MD 21550
      /56

      Est $275,591

      Not Listed For Sale

      309 Woodland Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,184 Sq Ft
      • Built 1970
      309 Woodland Dr, Oakland, MD 21550

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Brent Housley Railey Realty, Inc.

  • 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 $184,133

    Last Listing Agent Jonathan Minerick Homecoin.com

    170 Tannery Rd, 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 $194,333

      Not Listed For Sale

      219 W Liberty St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,360 Sq Ft
      • Built 1925
      219 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 185 Days On Market

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • 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

    Current Estimated Value $1,013,457

    Last Listing Agent Justin Liller Railey Realty, Inc.

    202 Penelacre Ln, 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 $332,315

      Not Listed For Sale

      413 N 2nd St, Oakland, MD 21550

      • 5 Beds
      • 2.5 Baths
      • 3,472 Sq Ft
      • Built 1962
      413 N 2nd St, Oakland, MD 21550

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

  • 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

    Current Estimated Value $3,598,649

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    870 Holy Cross 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 $231,066

      Not Listed For Sale

      132 N 8th St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,248 Sq Ft
      • Built 1940
      132 N 8th St, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

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

  • 105 Jasper Riley Rd, Oakland, MD 21550
    105 Jasper Riley Rd, Oakland, MD 21550
    105 Jasper Riley Rd, Oakland, MD 21550
    /61

    $318,500

    Sold Aug 07, 2026

    105 Jasper Riley Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,052 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $155/SF
    • 23 Days On Market

    Last Listing Agent Julie Mead The KW Collective

    105 Jasper Riley Rd, 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 $242,886

      Not Listed For Sale

      514 E Alder St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,152 Sq Ft
      • Built 1928
      514 E Alder St, Oakland, MD 21550

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

  • 143 Manor Dr, Oakland, MD 21550
    143 Manor Dr, Oakland, MD 21550
    143 Manor Dr, Oakland, MD 21550
    /48

    $285,000

    Sold Feb 19, 2026

    143 Manor Dr, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 1,786 Sq Ft
    • Built 1977

    Last Sold Summary

    • 5% Below List Price
    • $160/SF
    • 2 Days On Market

    Current Estimated Value $303,762

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    143 Manor Dr, 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

      1400 Wheeling Ave, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1990
      1400 Wheeling Ave, Oakland, MD 21550

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

Showing Results 641 - 680, Page 17 of 18

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