10,731

Oakland, MD Homes

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    • 94 Tannery Rd, Oakland, MD 21550
      94 Tannery Rd, Oakland, MD 21550
      94 Tannery Rd, Oakland, MD 21550
      /65

      Est $155,188 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,108 Sq Ft

      94 Tannery Rd, Oakland, MD 21550

      94 Tannery Rd, Oakland, MD 21550
  • 11 Laurel Brook Dr, Oakland, MD 21550
    11 Laurel Brook Dr, Oakland, MD 21550
    11 Laurel Brook Dr, Oakland, MD 21550
    /26

    $237,500 Sold Apr 15, 2025

    11 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • Built 1989

    Last Sold Summary

    • 157 Days On Market

    Current Estimated Value $257,598

    Last Listing Agent Dan Shockey Taylor Made Deep Creek Vacations & Sales

    11 Laurel Brook Dr, Oakland, MD 21550
    • 1606 Wheeling Ave, Oakland, MD 21550
      1606 Wheeling Ave, Oakland, MD 21550
      1606 Wheeling Ave, Oakland, MD 21550
      /66

      Est $206,357 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,502 Sq Ft

      1606 Wheeling Ave, Oakland, MD 21550

      1606 Wheeling Ave, Oakland, MD 21550
  • 636 Paradise Heights, Oakland, MD 21550
    636 Paradise Heights, Oakland, MD 21550
    636 Paradise Heights, Oakland, MD 21550
    /46

    $1,120,000 Sold Jul 08, 2025

    636 Paradise Heights, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,028 Sq Ft
    • Built 1986

    Last Sold Summary

    • $552/SF
    • 11 Days On Market

    Current Estimated Value $1,110,707

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    636 Paradise Heights, Oakland, MD 21550
    • 123 Spruce St, Oakland, MD 21550
      123 Spruce St, Oakland, MD 21550
      123 Spruce St, Oakland, MD 21550
      /24

      Est $232,492 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,392 Sq Ft

      123 Spruce St, Oakland, MD 21550

      123 Spruce St, Oakland, MD 21550
  • 5914 Maryland Hwy, Oakland, MD 21550
    5914 Maryland Hwy, Oakland, MD 21550
    5914 Maryland Hwy, Oakland, MD 21550
    /38

    $100,000 Sold Jul 11, 2025

    5914 Maryland Hwy, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,775 Sq Ft
    • Built 1973

    Last Sold Summary

    • $56/SF
    • 4 Days On Market

    Current Estimated Value $150,686

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

    5914 Maryland Hwy, Oakland, MD 21550
    • 79 Hummingbird Ct, Oakland, MD 21550
      79 Hummingbird Ct, Oakland, MD 21550
      79 Hummingbird Ct, Oakland, MD 21550
      /69

      Est $878,494 Not Listed For Sale

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

      79 Hummingbird Ct, Oakland, MD 21550

      79 Hummingbird Ct, Oakland, MD 21550
  • 4643 Oakland Sang Run Rd, Oakland, MD 21550
    4643 Oakland Sang Run Rd, Oakland, MD 21550
    4643 Oakland Sang Run Rd, Oakland, MD 21550
    /22

    $180,000 Sold Sep 12, 2025

    4643 Oakland Sang Run Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 1979

    Last Sold Summary

    • $208/SF
    • 4 Days On Market

    Current Estimated Value $190,901

    Last Listing Agent Jon Bell Railey Realty, Inc.

    4643 Oakland Sang Run Rd, Oakland, MD 21550
  • 198 Grandview Dr, Oakland, MD 21550
    198 Grandview Dr, Oakland, MD 21550
    198 Grandview Dr, Oakland, MD 21550
    /45

    $750,000 Sold Jan 16, 2026

    198 Grandview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,744 Sq Ft
    • Built 2003

    Last Sold Summary

    • $273/SF
    • 150 Days On Market

    Last Listing Agent Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, MD 21550
    • 105 Meadow Ct, Oakland, MD 21550
      105 Meadow Ct, Oakland, MD 21550
      105 Meadow Ct, Oakland, MD 21550
      /86

      Est $887,392 Not Listed For Sale

      • 4 Beds
      • 6 Baths
      • 3,192 Sq Ft

      105 Meadow Ct, Oakland, MD 21550

      105 Meadow Ct, Oakland, MD 21550
  • 72 Cliff Dr, Oakland, MD 21550
    72 Cliff Dr, Oakland, MD 21550
    72 Cliff Dr, Oakland, MD 21550
    /65

    $558,000 Sold Nov 10, 2025

    72 Cliff Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft
    • Built 1988

    Last Sold Summary

    • $256/SF
    • 32 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    72 Cliff Dr, Oakland, MD 21550
    • 57 Allegro Ln, Oakland, MD 21550
      57 Allegro Ln, Oakland, MD 21550
      57 Allegro Ln, Oakland, MD 21550
      /59

      Est $433,775 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,524 Sq Ft

      57 Allegro Ln, Oakland, MD 21550

      57 Allegro Ln, Oakland, MD 21550
  • 113 G St, Oakland, MD 21550
    113 G St, Oakland, MD 21550
    113 G St, Oakland, MD 21550
    /65

    $379,000 Sold Oct 08, 2025

    113 G St, Oakland, MD 21550

    • 9 Beds
    • 3.5 Baths
    • 3,840 Sq Ft
    • Built 1903

    Last Sold Summary

    • $99/SF
    • 40 Days On Market

    Current Estimated Value $378,042

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

    113 G St, Oakland, MD 21550
    • 491 Edens Ridge Rd, Oakland, MD 21550
      491 Edens Ridge Rd, Oakland, MD 21550
      491 Edens Ridge Rd, Oakland, MD 21550
      /73

      Est $650,711 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,318 Sq Ft

      491 Edens Ridge Rd, Oakland, MD 21550

      491 Edens Ridge Rd, Oakland, MD 21550
  • 1681 Shady Dell Rd, Oakland, MD 21550
    1681 Shady Dell Rd, Oakland, MD 21550
    1681 Shady Dell Rd, Oakland, MD 21550
    /31

    $189,000 Sold Jul 24, 2025

    1681 Shady Dell Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1985

    Last Sold Summary

    • $197/SF
    • 2 Days On Market

    Current Estimated Value $188,945

    Last Listing Agent Tim Macauley Taylor Made Deep Creek Vacations & Sales

    1681 Shady Dell Rd, Oakland, MD 21550
    • 2918 Oakland Sang Run Rd, Oakland, MD 21550
      2918 Oakland Sang Run Rd, Oakland, MD 21550
      2918 Oakland Sang Run Rd, Oakland, MD 21550
      /57

      Est $289,689 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,382 Sq Ft

      2918 Oakland Sang Run Rd, Oakland, MD 21550

      2918 Oakland Sang Run Rd, Oakland, MD 21550
  • 28 Wild Turkey Ln, Oakland, MD 21550
    28 Wild Turkey Ln, Oakland, MD 21550
    28 Wild Turkey Ln, Oakland, MD 21550
    /6

    $30,000 Sold Oct 23, 2025

    28 Wild Turkey Ln, Oakland, MD 21550

    • Land
    • 1 Acre
    • $30,000 per Acre

    Last Sold Summary

    • 14 Days On Market

    Last Listing Agent Dan Shockey Taylor Made Deep Creek Vacations & Sales

    28 Wild Turkey Ln, Oakland, MD 21550
    • 19398 Garrett Hwy, Oakland, MD 21550
      19398 Garrett Hwy, Oakland, MD 21550
      19398 Garrett Hwy, Oakland, MD 21550
      /49

      Est $334,321 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,414 Sq Ft

      19398 Garrett Hwy, Oakland, MD 21550

      19398 Garrett Hwy, Oakland, MD 21550
  • 234 Maple Del Ln, Oakland, MD 21550
    234 Maple Del Ln, Oakland, MD 21550
    234 Maple Del Ln, Oakland, MD 21550
    /51

    $435,000 Sold May 27, 2025

    234 Maple Del Ln, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,750 Sq Ft
    • Built 1995

    Last Sold Summary

    • $158/SF
    • 306 Days On Market

    Current Estimated Value $458,329

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

    234 Maple Del Ln, Oakland, MD 21550
    • 1070 Sunrise Dr, Oakland, MD 21550
      1070 Sunrise Dr, Oakland, MD 21550
      1070 Sunrise Dr, Oakland, MD 21550
      /33

      Est $264,230 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,144 Sq Ft

      1070 Sunrise Dr, Oakland, MD 21550

      1070 Sunrise Dr, Oakland, MD 21550
  • 34 Laurel Brook Dr, Oakland, MD 21550
    34 Laurel Brook Dr, Oakland, MD 21550
    34 Laurel Brook Dr, Oakland, MD 21550
    /34

    $275,000 Sold Jan 02, 2026

    34 Laurel Brook Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1992

    Last Sold Summary

    • 13 Days On Market

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

    34 Laurel Brook Dr, Oakland, MD 21550
    • 607 L St, Oakland, MD 21550
      607 L St, Oakland, MD 21550
      607 L St, Oakland, MD 21550
      /45

      Est $189,822 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,920 Sq Ft

      607 L St, Oakland, MD 21550

      607 L St, Oakland, MD 21550
  • 1764 Underwood Rd, Oakland, MD 21550
    1764 Underwood Rd, Oakland, MD 21550
    1764 Underwood Rd, Oakland, MD 21550
    /47

    $285,000 Sold Oct 31, 2025

    1764 Underwood Rd, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,304 Sq Ft
    • Built 1968

    Last Sold Summary

    • $124/SF
    • 175 Days On Market

    Current Estimated Value $278,744

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

    1764 Underwood Rd, Oakland, MD 21550
    • 482 Pergin Farm Rd, Oakland, MD 21550
      482 Pergin Farm Rd, Oakland, MD 21550
      482 Pergin Farm Rd, Oakland, MD 21550
      /48

      Est $470,660 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,160 Sq Ft

      482 Pergin Farm Rd, Oakland, MD 21550

      482 Pergin Farm Rd, Oakland, MD 21550
  • 969 Hoyes Run Rd, Oakland, MD 21550
    969 Hoyes Run Rd, Oakland, MD 21550
    969 Hoyes Run Rd, Oakland, MD 21550
    /56

    $697,000 Sold Dec 19, 2025

    969 Hoyes Run Rd, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,614 Sq Ft
    • Built 1998

    Last Sold Summary

    • $193/SF
    • 180 Days On Market

    Last Listing Agent Roberta McNamara RE/MAX Results

    969 Hoyes Run Rd, Oakland, MD 21550
    • 2127 Lake Shore Dr, Oakland, MD 21550
      2127 Lake Shore Dr, Oakland, MD 21550
      2127 Lake Shore Dr, Oakland, MD 21550
      /46

      Est $1,486,285 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,546 Sq Ft

      2127 Lake Shore Dr, Oakland, MD 21550

      2127 Lake Shore Dr, Oakland, MD 21550
  • 36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    /29

    $225,000 Sold Nov 17, 2025

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 520 Sq Ft
    • Built 1990

    Last Sold Summary

    • $433/SF
    • 26 Days On Market

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    • 1738 Paradise Point Rd, Oakland, MD 21550
      1738 Paradise Point Rd, Oakland, MD 21550
      1738 Paradise Point Rd, Oakland, MD 21550
      /97

      Est $2,497,535 Not Listed For Sale

      • 7 Beds
      • 5.5 Baths
      • 4,260 Sq Ft

      1738 Paradise Point Rd, Oakland, MD 21550

      1738 Paradise Point Rd, Oakland, MD 21550
  • 501 Christophers Way, Oakland, MD 21550
    501 Christophers Way, Oakland, MD 21550
    501 Christophers Way, Oakland, MD 21550
    /39

    $195,000 Sold Nov 12, 2025

    501 Christophers Way, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • Built 1994

    Last Sold Summary

    • $121/SF
    • 138 Days On Market

    Last Listing Agent Dan Shockey Taylor Made Deep Creek Vacations & Sales

    501 Christophers Way, Oakland, MD 21550
    • 1400 Oakland Ave, Oakland, MD 21550
      1400 Oakland Ave, Oakland, MD 21550
      1400 Oakland Ave, Oakland, MD 21550
      /78

      Est $226,385 Not Listed For Sale

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

      1400 Oakland Ave, Oakland, MD 21550

      1400 Oakland Ave, Oakland, MD 21550
  • 1136 Black Oak Dr, Oakland, MD 21550
    1136 Black Oak Dr, Oakland, MD 21550
    1136 Black Oak Dr, Oakland, MD 21550
    /41

    $218,000 Sold Dec 01, 2025

    1136 Black Oak Dr, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1971

    Last Sold Summary

    • $206/SF
    • 7 Days On Market

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

    1136 Black Oak Dr, Oakland, MD 21550
    • 1054 Lake Shore Dr, Oakland, MD 21550
      1054 Lake Shore Dr, Oakland, MD 21550
      1054 Lake Shore Dr, Oakland, MD 21550
      /56

      Est $715,915 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,667 Sq Ft

      1054 Lake Shore Dr, Oakland, MD 21550

      1054 Lake Shore Dr, Oakland, MD 21550
  • 2571 Shady Dell Rd, Oakland, MD 21550
    2571 Shady Dell Rd, Oakland, MD 21550
    2571 Shady Dell Rd, Oakland, MD 21550
    /18

    $200,000 Sold Sep 15, 2025

    2571 Shady Dell Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • Built 1985

    Last Sold Summary

    • $119/SF
    • 62 Days On Market

    Current Estimated Value $214,778

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    2571 Shady Dell Rd, Oakland, MD 21550
    • 8 Arrowhead Ln, Oakland, MD 21550
      8 Arrowhead Ln, Oakland, MD 21550
      8 Arrowhead Ln, Oakland, MD 21550
      /24

      Est $717,560 Not Listed For Sale

      • 3 Beds
      • 3 Baths

      8 Arrowhead Ln, Oakland, MD 21550

      8 Arrowhead Ln, Oakland, MD 21550
  • 128 Big Bass Dr, Oakland, MD 21550
    128 Big Bass Dr, Oakland, MD 21550
    128 Big Bass Dr, Oakland, MD 21550
    /93

    $1,445,000 Sold Nov 14, 2025

    128 Big Bass Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,305 Sq Ft
    • Built 2023

    Last Sold Summary

    • $336/SF
    • 13 Days On Market

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    128 Big Bass Dr, Oakland, MD 21550
    • 189 Whistle Pig Way, Oakland, MD 21550
      189 Whistle Pig Way, Oakland, MD 21550
      189 Whistle Pig Way, Oakland, MD 21550
      /88

      Est $498,948 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,777 Sq Ft

      189 Whistle Pig Way, Oakland, MD 21550

      189 Whistle Pig Way, Oakland, MD 21550
  • 531 S 3rd St, Oakland, MD 21550
    531 S 3rd St, Oakland, MD 21550
    531 S 3rd St, Oakland, MD 21550
    /56

    $320,000 Sold Nov 05, 2025

    531 S 3rd St, Oakland, MD 21550

    • 5 Beds
    • 2.5 Baths
    • 2,477 Sq Ft
    • Built 1920

    Last Sold Summary

    • $129/SF
    • 118 Days On Market

    Current Estimated Value $317,076

    Last Listing Agent Jennifer Jackson Charis Realty Group

    531 S 3rd St, Oakland, MD 21550
    • 2236 Paradise Point Rd, Oakland, MD 21550
      2236 Paradise Point Rd, Oakland, MD 21550
      2236 Paradise Point Rd, Oakland, MD 21550
      /80

      Est $1,478,652 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,004 Sq Ft

      2236 Paradise Point Rd, Oakland, MD 21550

      2236 Paradise Point Rd, Oakland, MD 21550
  • 405 Sunnyside Rd, Oakland, MD 21550
    405 Sunnyside Rd, Oakland, MD 21550
    405 Sunnyside Rd, Oakland, MD 21550
    /44

    $185,000 Sold Apr 14, 2025

    405 Sunnyside Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,184 Sq Ft
    • Built 1974

    Last Sold Summary

    • $85/SF
    • 100 Days On Market

    Current Estimated Value $197,953

    Last Listing Agent Steve DuBrueler Coldwell Banker Premier

    405 Sunnyside Rd, Oakland, MD 21550

Showing Results 441 - 480, Page 12 of 18

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