10,714

Oakland, MD Homes

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  • 247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    /82

    $554,999 Sold Oct 03, 2025

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2007

    Last Sold Summary

    • $168/SF
    • 164 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    247 Winding Trail Ln Unit 6B, 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 $538,727 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
  • Lot 76 S Blakeslee Rd, Oakland, MD 21550
    Lot 76 S Blakeslee Rd, Oakland, MD 21550
    Lot 76 S Blakeslee Rd, Oakland, MD 21550
    /12

    $380,000 Sold May 30, 2025

    Lot 76 S Blakeslee Rd, Oakland, MD 21550

    • Land
    • 1.06 Acres
    • $358,491 per Acre

    Last Sold Summary

    • 4 Days On Market

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

    Lot 76 S Blakeslee Rd, 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 $1,195,440 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      187 Lower Penn Point Dr, Oakland, MD 21550

      187 Lower Penn Point Dr, Oakland, MD 21550
  • 0 Lot 4 Sect 1 Blk B Piney Mtn Corp Sub Fawn Dr Unit MDGA2008660, Oakland, MD 21550
    0 Lot 4 Sect 1 Blk B Piney Mtn Corp Sub Fawn Dr Unit MDGA2008660, Oakland, MD 21550
    /2

    $3,000 Sold Jan 31, 2025

    0 Lot 4 Sect 1 Blk B Piney Mtn Corp Sub Fawn Dr Unit MDGA2008660, Oakland, MD 21550

    • Land
    • 0.5 Acre
    • $6,000 per Acre

    Last Sold Summary

    Last Listing Agent Robert Krop Keller Williams Realty Centre

    0 Lot 4 Sect 1 Blk B Piney Mtn Corp Sub Fawn Dr Unit MDGA2008660, 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 $1,444,400 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
  • 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
    • 91 Mallard Loop, Oakland, MD 21550
      91 Mallard Loop, Oakland, MD 21550
      91 Mallard Loop, Oakland, MD 21550
      /48

      Est $778,084 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
  • 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 $686,434

    Last Listing Agent Kellyann Green Railey Realty, Inc.

    26 Arrowhead Ln, Oakland, MD 21550
    • 1356 Stockslager Rd, Oakland, MD 21550
      1356 Stockslager Rd, Oakland, MD 21550
      1356 Stockslager Rd, Oakland, MD 21550
      /63

      Est $1,826,376 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 #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
    • 1174 Stockslager Rd, Oakland, MD 21550
      1174 Stockslager Rd, Oakland, MD 21550
      1174 Stockslager Rd, Oakland, MD 21550
      /108

      Est $1,972,971 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
  • 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

    Last Listing Agent Susan Bell Railey Realty, Inc.

    1087 Pergin Farm Rd, 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 $347,226 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
  • 1638 Memorial Dr, Oakland, MD 21550
    1638 Memorial Dr, Oakland, MD 21550
    1638 Memorial Dr, Oakland, MD 21550
    /59

    $275,000 Sold Jan 16, 2025

    1638 Memorial Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,328 Sq Ft
    • Built 1991

    Last Sold Summary

    • $207/SF
    • 5 Days On Market

    Current Estimated Value $285,681

    Last Listing Agent Julie Mead The KW Collective

    1638 Memorial Dr, Oakland, MD 21550
    • 1262 Memorial Dr, Oakland, MD 21550
      1262 Memorial Dr, Oakland, MD 21550
      1262 Memorial Dr, Oakland, MD 21550
      /55

      Est $375,164 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
  • 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
    • 600 S 3rd St, Oakland, MD 21550
      600 S 3rd St, Oakland, MD 21550
      600 S 3rd St, Oakland, MD 21550
      /42

      Est $260,870 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
  • 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
    • 153 N Scott St, Oakland, MD 21550
      153 N Scott St, Oakland, MD 21550
      153 N Scott St, Oakland, MD 21550
      /67

      Est $385,321 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
  • 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 $196,998

    Last Listing Agent Larry Smith Railey Realty, Inc.

    422 Underwood Rd, 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 $407,560 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
  • 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 $285,599

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    2360 Garrett Rd, Oakland, MD 21550
    • 109 N 2nd St, Oakland, MD 21550
      109 N 2nd St, Oakland, MD 21550
      109 N 2nd St, Oakland, MD 21550
      /45

      Est $338,318 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,614 Sq Ft

      109 N 2nd St, Oakland, MD 21550

      109 N 2nd 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

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

    2805 Shady Dell Rd, Oakland, MD 21550
    • 309 Woodland Dr, Oakland, MD 21550
      309 Woodland Dr, Oakland, MD 21550
      309 Woodland Dr, Oakland, MD 21550
      /56

      Est $290,928 Not Listed For Sale

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

      309 Woodland Dr, Oakland, MD 21550

      309 Woodland Dr, 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

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    197 Black Angus 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 $235,000 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
  • 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
    • 413 N 2nd St, Oakland, MD 21550
      413 N 2nd St, Oakland, MD 21550
      413 N 2nd St, Oakland, MD 21550
      /98

      Est $363,926 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
  • 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

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

    273 Glendale Rd, 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 $211,107 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
  • 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 $483,182

    Last Listing Agent Rich Orr Railey Realty, Inc.

    101 Sunset 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 $241,159 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
  • 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
    • 514 E Alder St, Oakland, MD 21550
      514 E Alder St, Oakland, MD 21550
      514 E Alder St, Oakland, MD 21550
      /36

      Est $264,617 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
  • 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
    • 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
  • 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

    Last Listing Agent Jonathan Minerick Homecoin.com

    170 Tannery Rd, Oakland, MD 21550
    • 1405 Wheeling Ave, Oakland, MD 21550
      1405 Wheeling Ave, Oakland, MD 21550
      1405 Wheeling Ave, Oakland, MD 21550
      /67

      Est $215,373 Not Listed For Sale

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

      1405 Wheeling Ave, Oakland, MD 21550

      1405 Wheeling Ave, Oakland, MD 21550

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