10,714

Oakland, MD Homes

Section Image
    • 301 Oak St, Oakland, MD 21550
      301 Oak St, Oakland, MD 21550
      301 Oak St, Oakland, MD 21550
      /67

      Est $332,717 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,400 Sq Ft

      301 Oak St, Oakland, MD 21550

      301 Oak St, Oakland, MD 21550
  • 805 Hunters Ridge Dr, Oakland, MD 21550
    805 Hunters Ridge Dr, Oakland, MD 21550
    805 Hunters Ridge Dr, Oakland, MD 21550
    /63

    $689,000 Sold Mar 18, 2025

    805 Hunters Ridge Dr, Oakland, MD 21550

    • 4 Beds
    • 4.5 Baths
    • 3,756 Sq Ft
    • Built 2010

    Last Sold Summary

    • $183/SF

    Current Estimated Value $696,058

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

    805 Hunters Ridge Dr, Oakland, MD 21550
    • 106 E 3rd Ave, Oakland, MD 21550
      106 E 3rd Ave, Oakland, MD 21550
      106 E 3rd Ave, Oakland, MD 21550
      /7

      Est $134,372 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 708 Sq Ft

      106 E 3rd Ave, Oakland, MD 21550

      106 E 3rd Ave, Oakland, MD 21550
  • 445 Dennett Rd, Oakland, MD 21550
    445 Dennett Rd, Oakland, MD 21550
    445 Dennett Rd, Oakland, MD 21550
    /62

    $305,000 Sold Nov 07, 2025

    445 Dennett Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,410 Sq Ft
    • Built 1955

    Last Sold Summary

    • $216/SF
    • 5 Days On Market

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    445 Dennett Rd, Oakland, MD 21550
    • 702 Pocahontas St, Oakland, MD 21550
      702 Pocahontas St, Oakland, MD 21550
      702 Pocahontas St, Oakland, MD 21550
      /64

      Est $542,906 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,288 Sq Ft

      702 Pocahontas St, Oakland, MD 21550

      702 Pocahontas St, Oakland, MD 21550
  • 1385 Mountainview Dr, Oakland, MD 21550
    1385 Mountainview Dr, Oakland, MD 21550
    1385 Mountainview Dr, Oakland, MD 21550
    /54

    $595,000 Sold Apr 30, 2025

    1385 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,660 Sq Ft
    • Built 2000

    Last Sold Summary

    • $224/SF
    • 26 Days On Market

    Current Estimated Value $609,360

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1385 Mountainview Dr, Oakland, MD 21550
    • 3529 Lake Shore Dr, Oakland, MD 21550
      3529 Lake Shore Dr, Oakland, MD 21550
      3529 Lake Shore Dr, Oakland, MD 21550
      /38

      Est $1,107,274 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,150 Sq Ft

      3529 Lake Shore Dr, Oakland, MD 21550

      3529 Lake Shore Dr, Oakland, MD 21550
  • 335 Mountainview Dr, Oakland, MD 21550
    335 Mountainview Dr, Oakland, MD 21550
    335 Mountainview Dr, Oakland, MD 21550
    /81

    $749,000 Sold Dec 31, 2024

    335 Mountainview Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,142 Sq Ft
    • Built 2001

    Last Sold Summary

    • $238/SF
    • 29 Days On Market

    Current Estimated Value $788,356

    Last Listing Agent Larry Smith Railey Realty, Inc.

    335 Mountainview Dr, Oakland, MD 21550
    • 250 N 4th St, Oakland, MD 21550
      250 N 4th St, Oakland, MD 21550
      250 N 4th St, Oakland, MD 21550
      /40

      Est $323,845 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,580 Sq Ft

      250 N 4th St, Oakland, MD 21550

      250 N 4th St, Oakland, MD 21550
  • 648 S 3rd St, Oakland, MD 21550
    648 S 3rd St, Oakland, MD 21550
    648 S 3rd St, Oakland, MD 21550
    /61

    $275,000 Sold Sep 05, 2025

    648 S 3rd St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1940

    Last Sold Summary

    • $185/SF
    • 3 Days On Market

    Current Estimated Value $282,287

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    648 S 3rd St, Oakland, MD 21550
    • 122 N 8th St, Oakland, MD 21550
      122 N 8th St, Oakland, MD 21550
      122 N 8th St, Oakland, MD 21550
      /51

      Est $253,127 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,376 Sq Ft

      122 N 8th St, Oakland, MD 21550

      122 N 8th St, Oakland, MD 21550
  • 35 Tenderfoot Rd, Oakland, MD 21550
    35 Tenderfoot Rd, Oakland, MD 21550
    35 Tenderfoot Rd, Oakland, MD 21550
    /51

    $425,000 Sold Dec 27, 2024

    35 Tenderfoot Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1999

    Last Sold Summary

    • $328/SF
    • 168 Days On Market

    Current Estimated Value $457,884

    Last Listing Agent Sandy Bello Taylor Made Deep Creek Vacations & Sales

    35 Tenderfoot Rd, Oakland, MD 21550
    • 140 Tender Foot Rd, Oakland, MD 21550
      140 Tender Foot Rd, Oakland, MD 21550
      140 Tender Foot Rd, Oakland, MD 21550
      /76

      Est $1,008,785 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,499 Sq Ft

      140 Tender Foot Rd, Oakland, MD 21550

      140 Tender Foot Rd, Oakland, MD 21550
  • 1746 Stockslager Rd, Oakland, MD 21550
    1746 Stockslager Rd, Oakland, MD 21550
    1746 Stockslager Rd, Oakland, MD 21550
    /131

    $2,250,000 Sold Mar 31, 2025

    1746 Stockslager Rd, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 4,713 Sq Ft
    • Built 1983

    Last Sold Summary

    • $477/SF
    • 131 Days On Market

    Current Estimated Value $2,348,109

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1746 Stockslager Rd, Oakland, MD 21550
    • 697 Mountainview Dr, Oakland, MD 21550
      697 Mountainview Dr, Oakland, MD 21550
      697 Mountainview Dr, Oakland, MD 21550
      /50

      Est $649,731 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,420 Sq Ft

      697 Mountainview Dr, Oakland, MD 21550

      697 Mountainview Dr, Oakland, MD 21550
  • 1220 Broadford Rd, Oakland, MD 21550
    1220 Broadford Rd, Oakland, MD 21550
    1220 Broadford Rd, Oakland, MD 21550
    /52

    $365,000 Sold Aug 12, 2025

    1220 Broadford Rd, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,092 Sq Ft
    • Built 1971

    Last Sold Summary

    • $174/SF
    • 58 Days On Market

    Current Estimated Value $364,839

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1220 Broadford Rd, Oakland, MD 21550
    • 1612 Mountainview Dr, Oakland, MD 21550
      1612 Mountainview Dr, Oakland, MD 21550
      1612 Mountainview Dr, Oakland, MD 21550
      /100

      Est $805,358 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,607 Sq Ft

      1612 Mountainview Dr, Oakland, MD 21550

      1612 Mountainview Dr, Oakland, MD 21550
  • 425 Mountainview Dr, Oakland, MD 21550
    425 Mountainview Dr, Oakland, MD 21550
    425 Mountainview Dr, Oakland, MD 21550
    /50

    $739,000 Sold Oct 17, 2025

    425 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,586 Sq Ft
    • Built 1998

    Last Sold Summary

    • $466/SF
    • 32 Days On Market

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

    425 Mountainview Dr, Oakland, MD 21550
    • 1194 Lake Shore Dr, Oakland, MD 21550
      1194 Lake Shore Dr, Oakland, MD 21550
      1194 Lake Shore Dr, Oakland, MD 21550
      /51

      Est $699,836 Not Listed For Sale

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

      1194 Lake Shore Dr, Oakland, MD 21550

      1194 Lake Shore Dr, Oakland, MD 21550
  • 1073 George Washington Hwy, Oakland, MD 21550
    1073 George Washington Hwy, Oakland, MD 21550
    1073 George Washington Hwy, Oakland, MD 21550
    /89

    $365,000 Sold Feb 28, 2025

    1073 George Washington Hwy, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,910 Sq Ft
    • Built 1876

    Last Sold Summary

    • $125/SF

    Current Estimated Value $365,838

    Last Listing Agent Justin Liller Railey Realty, Inc.

    1073 George Washington Hwy, Oakland, MD 21550
    • 219 Mountainview Dr, Oakland, MD 21550
      219 Mountainview Dr, Oakland, MD 21550
      219 Mountainview Dr, Oakland, MD 21550
      /95

      Est $812,590 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,041 Sq Ft

      219 Mountainview Dr, Oakland, MD 21550

      219 Mountainview Dr, Oakland, MD 21550
  • 3094 Cranesville Rd, Oakland, MD 21550
    3094 Cranesville Rd, Oakland, MD 21550
    3094 Cranesville Rd, Oakland, MD 21550
    /52

    $479,000 Sold Feb 07, 2025

    3094 Cranesville Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,490 Sq Ft
    • Built 1938

    Last Sold Summary

    • $321/SF
    • 0 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    3094 Cranesville Rd, Oakland, MD 21550
    • 221 Randall Way, Oakland, MD 21550
      221 Randall Way, Oakland, MD 21550
      221 Randall Way, Oakland, MD 21550
      /106

      Est $1,781,099 Not Listed For Sale

      • 5 Beds
      • 6 Baths
      • 5,155 Sq Ft

      221 Randall Way, Oakland, MD 21550

      221 Randall Way, Oakland, MD 21550
  • 3273 Lake Shore Dr, Oakland, MD 21550
    3273 Lake Shore Dr, Oakland, MD 21550
    3273 Lake Shore Dr, Oakland, MD 21550
    /80

    $1,270,000 Sold Oct 16, 2025

    3273 Lake Shore Dr, Oakland, MD 21550

    • 6 Beds
    • 3 Baths
    • 1,714 Sq Ft
    • Built 1930

    Last Sold Summary

    • $741/SF
    • 6 Days On Market

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

    3273 Lake Shore Dr, Oakland, MD 21550
    • 939 Glendale Rd Unit 16, Oakland, MD 21550
      939 Glendale Rd Unit 16, Oakland, MD 21550
      939 Glendale Rd Unit 16, Oakland, MD 21550
      /33

      Est $599,932 Not Listed For Sale

      • 2 Beds
      • 2 Baths

      939 Glendale Rd Unit 16, Oakland, MD 21550

      939 Glendale Rd Unit 16, Oakland, MD 21550
  • 1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    /93

    $3,000,000 Sold Dec 02, 2025

    1931 Lake Shore Dr, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 5,100 Sq Ft
    • Built 2009

    Last Sold Summary

    • $588/SF
    • 430 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1931 Lake Shore Dr, Oakland, MD 21550
    • 262 Penn Cove Rd, Oakland, MD 21550
      262 Penn Cove Rd, Oakland, MD 21550
      262 Penn Cove Rd, Oakland, MD 21550
      /106

      Est $1,030,893 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,700 Sq Ft

      262 Penn Cove Rd, Oakland, MD 21550

      262 Penn Cove Rd, Oakland, MD 21550
  • 267 Woodlands Hill Ln, Oakland, MD 21550
    267 Woodlands Hill Ln, Oakland, MD 21550
    267 Woodlands Hill Ln, Oakland, MD 21550
    /72

    $975,000 Sold Sep 25, 2025

    267 Woodlands Hill Ln, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,232 Sq Ft
    • Built 2021

    Last Sold Summary

    • $437/SF
    • 136 Days On Market

    Current Estimated Value $999,285

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

    267 Woodlands Hill Ln, Oakland, MD 21550
    • 545 Cumberland Rd, Oakland, MD 21550
      545 Cumberland Rd, Oakland, MD 21550
      545 Cumberland Rd, Oakland, MD 21550
      /100

      Est $573,925 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft

      545 Cumberland Rd, Oakland, MD 21550

      545 Cumberland Rd, Oakland, MD 21550
  • 1100 S Blakeslee Rd, Oakland, MD 21550
    1100 S Blakeslee Rd, Oakland, MD 21550
    1100 S Blakeslee Rd, Oakland, MD 21550
    /127

    $2,550,000 Sold Aug 01, 2025

    1100 S Blakeslee Rd, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 6,572 Sq Ft
    • Built 1998

    Last Sold Summary

    • $388/SF
    • 0 Days On Market

    Current Estimated Value $2,731,196

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    1100 S Blakeslee 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 $410,652 Not Listed For Sale

      • 1 Bed
      • 1.5 Baths
      • 665 Sq Ft

      3598 Lake Shore Dr, Oakland, MD 21550

      3598 Lake Shore Dr, Oakland, MD 21550
  • 346 Skippers Point Rd, Oakland, MD 21550
    346 Skippers Point Rd, Oakland, MD 21550
    346 Skippers Point Rd, Oakland, MD 21550
    /73

    $530,000 Sold Oct 03, 2025

    346 Skippers Point Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Built 1976

    Last Sold Summary

    • $294/SF
    • 50 Days On Market

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    346 Skippers Point Rd, 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 $1,263,863 Not Listed For Sale

      • 3 Beds
      • 4.5 Baths
      • 1,968 Sq Ft

      3003 Lake Shore Dr, Oakland, MD 21550

      3003 Lake Shore Dr, Oakland, MD 21550
  • 15705 Garrett Hwy, Oakland, MD 21550
    15705 Garrett Hwy, Oakland, MD 21550
    15705 Garrett Hwy, Oakland, MD 21550
    /50

    $275,000 Sold Jan 22, 2025

    15705 Garrett Hwy, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,046 Sq Ft
    • Built 1965

    Last Sold Summary

    • $134/SF
    • 146 Days On Market

    Current Estimated Value $306,763

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    15705 Garrett Hwy, 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 $3,068,205 Not Listed For Sale

      • 6 Beds
      • 4.5 Baths
      • 5,859 Sq Ft

      2303 Lake Shore Dr, Oakland, MD 21550

      2303 Lake Shore Dr, Oakland, MD 21550
  • 735 Winston Rd, Oakland, MD 21550
    735 Winston Rd, Oakland, MD 21550
    735 Winston Rd, Oakland, MD 21550
    /53

    $1,300,000 Sold Apr 30, 2025

    735 Winston Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 2,076 Sq Ft
    • Built 1985

    Last Sold Summary

    • $626/SF
    • 10 Days On Market

    Current Estimated Value $82,000

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    735 Winston Rd, Oakland, MD 21550
    • 568 Skippers Point Rd, Oakland, MD 21550
      568 Skippers Point Rd, Oakland, MD 21550
      568 Skippers Point Rd, Oakland, MD 21550
      /60

      Est $541,081 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 960 Sq Ft

      568 Skippers Point Rd, Oakland, MD 21550

      568 Skippers Point Rd, Oakland, MD 21550
  • 18361 Garrett Hwy, Oakland, MD 21550
    18361 Garrett Hwy, Oakland, MD 21550
    18361 Garrett Hwy, Oakland, MD 21550
    /51

    $268,000 Sold Feb 27, 2025

    18361 Garrett Hwy, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,112 Sq Ft
    • Built 1977

    Last Sold Summary

    • $127/SF
    • 131 Days On Market

    Current Estimated Value $282,849

    Last Listing Agent Jon Bell Railey Realty, Inc.

    18361 Garrett Hwy, Oakland, MD 21550
    • 50 Hooppole Ct, Oakland, MD 21550
      50 Hooppole Ct, Oakland, MD 21550
      50 Hooppole Ct, Oakland, MD 21550
      /48

      Est $751,202 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,436 Sq Ft

      50 Hooppole Ct, Oakland, MD 21550

      50 Hooppole Ct, Oakland, MD 21550
  • 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

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