10,714

Oakland, MD Homes

Section Image
  • 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 $1,103,217

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    636 Paradise Heights, Oakland, MD 21550
    • 111 W Liberty St, Oakland, MD 21550
      111 W Liberty St, Oakland, MD 21550
      111 W Liberty St, Oakland, MD 21550
      /4

      Est $79,915 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,528 Sq Ft

      111 W Liberty St, Oakland, MD 21550

      111 W Liberty St, 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 $186,513

    Last Listing Agent Jon Bell Railey Realty, Inc.

    4643 Oakland Sang Run Rd, Oakland, MD 21550
    • 378 Lower Penn Point Dr, Oakland, MD 21550
      378 Lower Penn Point Dr, Oakland, MD 21550
      378 Lower Penn Point Dr, Oakland, MD 21550
      /25

      Est $1,150,015 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,114 Sq Ft

      378 Lower Penn Point Dr, Oakland, MD 21550

      378 Lower Penn Point Dr, 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
    • 94 Tannery Rd, Oakland, MD 21550
      94 Tannery Rd, Oakland, MD 21550
      94 Tannery Rd, Oakland, MD 21550
      /65

      Est $167,598 Not Listed For Sale

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

      94 Tannery Rd, Oakland, MD 21550

      94 Tannery Rd, 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

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

    113 G St, Oakland, MD 21550
    • 1606 Wheeling Ave, Oakland, MD 21550
      1606 Wheeling Ave, Oakland, MD 21550
      1606 Wheeling Ave, Oakland, MD 21550
      /66

      Est $205,986 Not Listed For Sale

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

      1606 Wheeling Ave, Oakland, MD 21550

      1606 Wheeling Ave, 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 $186,673

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

    1681 Shady Dell Rd, Oakland, MD 21550
    • 123 Spruce St, Oakland, MD 21550
      123 Spruce St, Oakland, MD 21550
      123 Spruce St, Oakland, MD 21550
      /24

      Est $233,964 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
  • 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
    • 79 Hummingbird Ct, Oakland, MD 21550
      79 Hummingbird Ct, Oakland, MD 21550
      79 Hummingbird Ct, Oakland, MD 21550
      /69

      Est $900,055 Not Listed For Sale

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

      79 Hummingbird Ct, Oakland, MD 21550

      79 Hummingbird Ct, 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 $465,812

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

    234 Maple Del Ln, Oakland, MD 21550
    • 105 Meadow Ct, Oakland, MD 21550
      105 Meadow Ct, Oakland, MD 21550
      105 Meadow Ct, Oakland, MD 21550
      /86

      Est $874,216 Not Listed For Sale

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

      105 Meadow Ct, Oakland, MD 21550

      105 Meadow Ct, Oakland, MD 21550
  • 510 Palmer Ln, Oakland, MD 21550
    510 Palmer Ln, Oakland, MD 21550
    510 Palmer Ln, Oakland, MD 21550
    /40

    $369,000 Sold Jan 23, 2025

    510 Palmer Ln, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,922 Sq Ft
    • Built 2024

    Last Sold Summary

    • $192/SF
    • 0 Days On Market

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

    510 Palmer Ln, 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 $648,452 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
  • 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

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

    1764 Underwood 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 $286,771 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
  • 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
    • 19398 Garrett Hwy, Oakland, MD 21550
      19398 Garrett Hwy, Oakland, MD 21550
      19398 Garrett Hwy, Oakland, MD 21550
      /49

      Est $338,770 Not Listed For Sale

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

      19398 Garrett Hwy, Oakland, MD 21550

      19398 Garrett Hwy, 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
    • 1070 Sunrise Dr, Oakland, MD 21550
      1070 Sunrise Dr, Oakland, MD 21550
      1070 Sunrise Dr, Oakland, MD 21550
      /33

      Est $257,457 Not Listed For Sale

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

      1070 Sunrise Dr, Oakland, MD 21550

      1070 Sunrise Dr, 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
    • 607 L St, Oakland, MD 21550
      607 L St, Oakland, MD 21550
      607 L St, Oakland, MD 21550
      /45

      Est $188,179 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
  • 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
    • 482 Pergin Farm Rd, Oakland, MD 21550
      482 Pergin Farm Rd, Oakland, MD 21550
      482 Pergin Farm Rd, Oakland, MD 21550
      /48

      Est $460,465 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
  • 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 $211,466

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    2571 Shady Dell 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 $1,526,781 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
  • 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
    • 1738 Paradise Point Rd, Oakland, MD 21550
      1738 Paradise Point Rd, Oakland, MD 21550
      1738 Paradise Point Rd, Oakland, MD 21550
      /97

      Est $2,725,579 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
  • 93 Skippers Point Rd, Oakland, MD 21550
    93 Skippers Point Rd, Oakland, MD 21550
    93 Skippers Point Rd, Oakland, MD 21550
    /64

    $1,950,000 Sold Dec 27, 2024

    93 Skippers Point Rd, Oakland, MD 21550

    • 5 Beds
    • 7 Baths
    • 3,300 Sq Ft
    • Built 2022

    Last Sold Summary

    • $591/SF
    • 20 Days On Market

    Current Estimated Value $2,113,594

    Last Listing Agent Lucas Muenchow Railey Realty, Inc.

    93 Skippers Point Rd, Oakland, MD 21550
    • 1400 Oakland Ave, Oakland, MD 21550
      1400 Oakland Ave, Oakland, MD 21550
      1400 Oakland Ave, Oakland, MD 21550
      /78

      Est $221,128 Not Listed For Sale

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

      1400 Oakland Ave, Oakland, MD 21550

      1400 Oakland Ave, 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

    Last Listing Agent Jennifer Jackson Charis Realty Group

    531 S 3rd St, Oakland, MD 21550
    • 25 Fern Dr, Oakland, MD 21550
      25 Fern Dr, Oakland, MD 21550
      25 Fern Dr, Oakland, MD 21550
      /48

      Est $377,690 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,536 Sq Ft

      25 Fern Dr, Oakland, MD 21550

      25 Fern Dr, 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 $196,959

    Last Listing Agent Steve DuBrueler Coldwell Banker Premier

    405 Sunnyside Rd, 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 $678,395 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
  • 707 Sunshine Dr, Oakland, MD 21550
    707 Sunshine Dr, Oakland, MD 21550
    707 Sunshine Dr, Oakland, MD 21550
    /68

    $310,000 Sold Jul 31, 2025

    707 Sunshine Dr, Oakland, MD 21550

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

    Last Sold Summary

    • $151/SF
    • 94 Days On Market

    Current Estimated Value $320,222

    Last Listing Agent Tyler Burch Burch Real Estate Group, LLC

    707 Sunshine Dr, Oakland, MD 21550
    • 8 Arrowhead Ln, Oakland, MD 21550
      8 Arrowhead Ln, Oakland, MD 21550
      8 Arrowhead Ln, Oakland, MD 21550
      /24

      Est $727,440 Not Listed For Sale

      • 3 Beds
      • 3 Baths

      8 Arrowhead Ln, Oakland, MD 21550

      8 Arrowhead Ln, Oakland, MD 21550
  • 1484 Paradise Point Rd, Oakland, MD 21550
    1484 Paradise Point Rd, Oakland, MD 21550
    1484 Paradise Point Rd, Oakland, MD 21550
    /47

    $1,762,500 Sold Jul 29, 2025

    1484 Paradise Point Rd, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,360 Sq Ft
    • Built 2022

    Last Sold Summary

    • $525/SF
    • 16 Days On Market

    Current Estimated Value $1,750,161

    Last Listing Agent Kelsey Meyers Railey Realty, Inc.

    1484 Paradise Point Rd, 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 $438,754 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

Showing Results 441 - 480, Page 12 of 18

Maryland Garrett County Oakland

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group