10,731

Oakland, MD Homes

Section Image
    • 512 Roanoke Ave, Oakland, MD 21550
      512 Roanoke Ave, Oakland, MD 21550
      512 Roanoke Ave, Oakland, MD 21550
      /25

      Est $148,746 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft

      512 Roanoke Ave, Oakland, MD 21550

      512 Roanoke Ave, Oakland, MD 21550
  • 4012 Maryland Hwy, Oakland, MD 21550
    4012 Maryland Hwy, Oakland, MD 21550
    4012 Maryland Hwy, Oakland, MD 21550
    /55

    $280,000 Sold Jul 31, 2025

    4012 Maryland Hwy, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,824 Sq Ft
    • Built 1968

    Last Sold Summary

    • $154/SF
    • 32 Days On Market

    Current Estimated Value $281,620

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    4012 Maryland Hwy, Oakland, MD 21550
    • 204 D St, Oakland, MD 21550
      204 D St, Oakland, MD 21550
      204 D St, Oakland, MD 21550
      /19

      Est $155,911 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft

      204 D St, Oakland, MD 21550

      204 D St, Oakland, MD 21550
  • 4.00 Acres Moose Crossing, Oakland, MD 21550
    4.00 Acres Moose Crossing, Oakland, MD 21550
    4.00 Acres Moose Crossing, Oakland, MD 21550
    /18

    $75,000 Sold Sep 25, 2025

    4.00 Acres Moose Crossing, Oakland, MD 21550

    • Land
    • 4 Acres
    • $18,750 per Acre

    Last Sold Summary

    • 27 Days On Market

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

    4.00 Acres Moose Crossing, Oakland, MD 21550
    • 132 Hillside Dr, Oakland, MD 21550
      132 Hillside Dr, Oakland, MD 21550
      132 Hillside Dr, Oakland, MD 21550
      /61

      Est $271,733 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,488 Sq Ft

      132 Hillside Dr, Oakland, MD 21550

      132 Hillside Dr, Oakland, MD 21550
  • 0 Lot#2 Farmview Ln, Oakland, MD 21550
    0 Lot#2 Farmview Ln, Oakland, MD 21550
    0 Lot#2 Farmview Ln, Oakland, MD 21550
    /17

    $28,000 Sold Feb 28, 2025

    0 Lot#2 Farmview Ln, Oakland, MD 21550

    • Land
    • 0.95 Acre
    • $29,474 per Acre

    Last Sold Summary

    • 192 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    0 Lot#2 Farmview Ln, Oakland, MD 21550
    • 1306 Wheeling Ave, Oakland, MD 21550
      1306 Wheeling Ave, Oakland, MD 21550
      1306 Wheeling Ave, Oakland, MD 21550
      /22

      Est $281,295 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,624 Sq Ft

      1306 Wheeling Ave, Oakland, MD 21550

      1306 Wheeling Ave, Oakland, MD 21550
  • 16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    /70

    $555,000 Sold Nov 20, 2025

    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft
    • Built 2009

    Last Sold Summary

    • $206/SF
    • 68 Days On Market

    Last Listing Agent Justin Liller Railey Realty, Inc.

    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    • 410 K St, Oakland, MD 21550
      410 K St, Oakland, MD 21550
      410 K St, Oakland, MD 21550
      /21

      Est $128,847 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,440 Sq Ft

      410 K St, Oakland, MD 21550

      410 K St, Oakland, MD 21550
  • 3941 Pleasant Valley Rd, Oakland, MD 21550
    3941 Pleasant Valley Rd, Oakland, MD 21550
    3941 Pleasant Valley Rd, Oakland, MD 21550
    /46

    $110,000 Sold Apr 04, 2025

    3941 Pleasant Valley Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,060 Sq Ft
    • Built 1900

    Last Sold Summary

    • $53/SF
    • 82 Days On Market

    Current Estimated Value $141,097

    Last Listing Agent Ben Maust Railey Realty, Inc.

    3941 Pleasant Valley Rd, Oakland, MD 21550
    • 1100 Oakland Ave, Oakland, MD 21550
      1100 Oakland Ave, Oakland, MD 21550
      1100 Oakland Ave, Oakland, MD 21550
      /25

      Est $203,100 Not Listed For Sale

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

      1100 Oakland Ave, Oakland, MD 21550

      1100 Oakland Ave, Oakland, MD 21550
  • 206 N 10th St, Oakland, MD 21550
    206 N 10th St, Oakland, MD 21550
    206 N 10th St, Oakland, MD 21550
    /103

    $320,000 Sold Jul 18, 2025

    206 N 10th St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,772 Sq Ft
    • Built 1972

    Last Sold Summary

    • $115/SF
    • 37 Days On Market

    Current Estimated Value $334,139

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    206 N 10th St, Oakland, MD 21550
    • 1107 Oakland Ave, Oakland, MD 21550
      1107 Oakland Ave, Oakland, MD 21550
      1107 Oakland Ave, Oakland, MD 21550
      /42

      Est $162,412 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,152 Sq Ft

      1107 Oakland Ave, Oakland, MD 21550

      1107 Oakland Ave, Oakland, MD 21550
  • 111 Tarn Dr, Oakland, MD 21550
    111 Tarn Dr, Oakland, MD 21550
    111 Tarn Dr, Oakland, MD 21550
    /20

    $40,000 Sold Oct 20, 2025

    111 Tarn Dr, Oakland, MD 21550

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

    Last Sold Summary

    • 260 Days On Market

    Current Estimated Value $957,540

    Last Listing Agent Amy Grubby AEK Real Estate, LLC

    111 Tarn Dr, Oakland, MD 21550
    • 13 Hazel Glade Dr, Oakland, MD 21550
      13 Hazel Glade Dr, Oakland, MD 21550
      13 Hazel Glade Dr, Oakland, MD 21550
      /64

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft

      13 Hazel Glade Dr, Oakland, MD 21550

      13 Hazel Glade Dr, Oakland, MD 21550
  • 20241 Garrett Hwy Unit 5, Oakland, MD 21550
    20241 Garrett Hwy Unit 5, Oakland, MD 21550
    20241 Garrett Hwy Unit 5, Oakland, MD 21550
    /47

    $407,000 Sold Apr 18, 2025

    20241 Garrett Hwy Unit 5, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,330 Sq Ft
    • Built 1989

    Last Sold Summary

    • $175/SF
    • 9 Days On Market

    Current Estimated Value $419,969

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    20241 Garrett Hwy Unit 5, Oakland, MD 21550
    • 318 Allegheny Dr, Oakland, MD 21550
      318 Allegheny Dr, Oakland, MD 21550
      318 Allegheny Dr, Oakland, MD 21550
      /47

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft

      318 Allegheny Dr, Oakland, MD 21550

      318 Allegheny Dr, Oakland, MD 21550
  • 230 Moose Crossing, Oakland, MD 21550
    230 Moose Crossing, Oakland, MD 21550
    230 Moose Crossing, Oakland, MD 21550
    /100

    $455,000 Sold Mar 28, 2025

    230 Moose Crossing, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,441 Sq Ft
    • Built 1980

    Last Sold Summary

    • $186/SF
    • 115 Days On Market

    Current Estimated Value $460,730

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

    230 Moose Crossing, Oakland, MD 21550
    • 700 I St, Oakland, MD 21550
      700 I St, Oakland, MD 21550
      700 I St, Oakland, MD 21550
      /48

      Est $170,401 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,168 Sq Ft

      700 I St, Oakland, MD 21550

      700 I St, Oakland, MD 21550
  • 465 Pergin Farm Rd, Oakland, MD 21550
    465 Pergin Farm Rd, Oakland, MD 21550
    465 Pergin Farm Rd, Oakland, MD 21550
    /79

    $735,000 Sold Dec 18, 2025

    465 Pergin Farm Rd, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,960 Sq Ft
    • Built 2006

    Last Sold Summary

    • $248/SF
    • 9 Days On Market

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

    465 Pergin Farm Rd, Oakland, MD 21550
    • 409 M St, Oakland, MD 21550
      409 M St, Oakland, MD 21550
      409 M St, Oakland, MD 21550
      /29

      Est $190,706 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,208 Sq Ft

      409 M St, Oakland, MD 21550

      409 M St, Oakland, MD 21550
  • p/o parcel 206 G Swauger Rd, Oakland, MD 21550
    p/o parcel 206 G Swauger Rd, Oakland, MD 21550
    p/o parcel 206 G Swauger Rd, Oakland, MD 21550
    /4

    $61,125 Sold Jun 25, 2025

    p/o parcel 206 G Swauger Rd, Oakland, MD 21550

    • Land
    • 6.75 Acres
    • $9,056 per Acre

    Last Sold Summary

    Last Listing Agent Rich Orr Railey Realty, Inc.

    p/o parcel 206 G Swauger Rd, Oakland, MD 21550
    • 513 K St, Oakland, MD 21550
      513 K St, Oakland, MD 21550
      513 K St, Oakland, MD 21550
      /36

      Est $83,674 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,404 Sq Ft

      513 K St, Oakland, MD 21550

      513 K St, Oakland, MD 21550
  • 408 Shenandoah Ave, Oakland, MD 21550
    408 Shenandoah Ave, Oakland, MD 21550
    408 Shenandoah Ave, Oakland, MD 21550
    /43

    $110,000 Sold Jul 16, 2025

    408 Shenandoah Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1950

    Last Sold Summary

    • $115/SF
    • 2 Days On Market

    Current Estimated Value $109,631

    Last Listing Agent Rich Orr Railey Realty, Inc.

    408 Shenandoah Ave, Oakland, MD 21550
    • 1107 Broadford Rd, Oakland, MD 21550
      1107 Broadford Rd, Oakland, MD 21550
      1107 Broadford Rd, Oakland, MD 21550
      /5

      Est $244,047 Not Listed For Sale

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

      1107 Broadford Rd, Oakland, MD 21550

      1107 Broadford Rd, Oakland, MD 21550
  • 19956 Garrett Hwy Unit 2, Oakland, MD 21550
    19956 Garrett Hwy Unit 2, Oakland, MD 21550
    19956 Garrett Hwy Unit 2, Oakland, MD 21550
    /57

    $1,200,000 Sold Jun 13, 2025

    19956 Garrett Hwy Unit 2, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 3,012 Sq Ft
    • Built 2007

    Last Sold Summary

    • $398/SF
    • 5 Days On Market

    Current Estimated Value $1,194,955

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

    19956 Garrett Hwy Unit 2, Oakland, MD 21550
    • 505 Shenandoah Ave, Oakland, MD 21550
      505 Shenandoah Ave, Oakland, MD 21550
      505 Shenandoah Ave, Oakland, MD 21550
      /23

      Est $141,395 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,632 Sq Ft

      505 Shenandoah Ave, Oakland, MD 21550

      505 Shenandoah Ave, Oakland, MD 21550
  • 88 Knoll Crest Heights Dr, Oakland, MD 21550
    88 Knoll Crest Heights Dr, Oakland, MD 21550
    88 Knoll Crest Heights Dr, Oakland, MD 21550
    /38

    $225,000 Sold Oct 16, 2025

    88 Knoll Crest Heights Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,867 Sq Ft
    • Built 1974

    Last Sold Summary

    • $121/SF
    • 31 Days On Market

    Current Estimated Value $229,338

    Last Listing Agent Justin Liller Railey Realty, Inc.

    88 Knoll Crest Heights Dr, Oakland, MD 21550
    • 113 Jubb Meadows Ln, Oakland, MD 21550
      113 Jubb Meadows Ln, Oakland, MD 21550
      113 Jubb Meadows Ln, Oakland, MD 21550
      /95

      Est $888,688 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,185 Sq Ft

      113 Jubb Meadows Ln, Oakland, MD 21550

      113 Jubb Meadows Ln, Oakland, MD 21550
  • 22 Black Oak Dr, Oakland, MD 21550
    22 Black Oak Dr, Oakland, MD 21550
    22 Black Oak Dr, Oakland, MD 21550
    /29

    $220,000 Sold May 30, 2025

    22 Black Oak Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1998

    Last Sold Summary

    • $170/SF
    • 16 Days On Market

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

    22 Black Oak Dr, Oakland, MD 21550
    • 242 Interlude Ln, Oakland, MD 21550
      242 Interlude Ln, Oakland, MD 21550
      242 Interlude Ln, Oakland, MD 21550
      /10

      Est $286,888 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,544 Sq Ft

      242 Interlude Ln, Oakland, MD 21550

      242 Interlude Ln, Oakland, MD 21550
  • 10178 Garrett Hwy, Oakland, MD 21550
    10178 Garrett Hwy, Oakland, MD 21550
    10178 Garrett Hwy, Oakland, MD 21550
    /12

    $86,000 Sold Apr 17, 2025

    10178 Garrett Hwy, Oakland, MD 21550

    • Land
    • 3.04 Acres
    • $28,289 per Acre

    Last Sold Summary

    • 7 Days On Market

    Current Estimated Value $91,151

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    10178 Garrett Hwy, Oakland, MD 21550
    • 2078 Sanders Ln, Oakland, MD 21550
      2078 Sanders Ln, Oakland, MD 21550
      2078 Sanders Ln, Oakland, MD 21550
      /85

      Est $462,716 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,904 Sq Ft

      2078 Sanders Ln, Oakland, MD 21550

      2078 Sanders Ln, Oakland, MD 21550
  • 31 Mount Airy Ct, Oakland, MD 21550
    31 Mount Airy Ct, Oakland, MD 21550
    31 Mount Airy Ct, Oakland, MD 21550
    /13

    $122,000 Sold Apr 11, 2025

    31 Mount Airy Ct, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,092 Sq Ft
    • Built 2012

    Last Sold Summary

    • $112/SF
    • 22 Days On Market

    Current Estimated Value $123,773

    Last Listing Agent Katie Cantrell Taylor Made Deep Creek Vacations & Sales

    31 Mount Airy Ct, Oakland, MD 21550
    • 181 Glotfelty Dr, Oakland, MD 21550
      181 Glotfelty Dr, Oakland, MD 21550
      181 Glotfelty Dr, Oakland, MD 21550
      /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft

      181 Glotfelty Dr, Oakland, MD 21550

      181 Glotfelty Dr, Oakland, MD 21550
  • 83 Boston Post Rd, Oakland, MD 21550
    83 Boston Post Rd, Oakland, MD 21550
    83 Boston Post Rd, Oakland, MD 21550
    /41

    $247,500 Sold Oct 03, 2025

    83 Boston Post Rd, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 400 Sq Ft
    • Built 2019

    Last Sold Summary

    • $619/SF
    • 109 Days On Market

    Current Estimated Value $251,889

    Last Listing Agent Brent Housley Railey Realty, Inc.

    83 Boston Post Rd, Oakland, MD 21550
    • 367 Underwood Rd, Oakland, MD 21550
      367 Underwood Rd, Oakland, MD 21550
      367 Underwood Rd, Oakland, MD 21550
      /56

      Est $247,631 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,400 Sq Ft

      367 Underwood Rd, Oakland, MD 21550

      367 Underwood Rd, Oakland, MD 21550
  • 2463 Mayhew Inn Rd, Oakland, MD 21550
    2463 Mayhew Inn Rd, Oakland, MD 21550
    2463 Mayhew Inn Rd, Oakland, MD 21550
    /144

    $1,950,000 Sold Nov 25, 2025

    2463 Mayhew Inn Rd, Oakland, MD 21550

    • 6 Beds
    • 5.5 Baths
    • 5,389 Sq Ft
    • Built 1989

    Last Sold Summary

    • $362/SF
    • 329 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    2463 Mayhew Inn Rd, Oakland, MD 21550
    • 704 Old Crellin Rd, Oakland, MD 21550
      704 Old Crellin Rd, Oakland, MD 21550
      704 Old Crellin Rd, Oakland, MD 21550
      /42

      Est $373,769 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 2,507 Sq Ft

      704 Old Crellin Rd, Oakland, MD 21550

      704 Old Crellin Rd, Oakland, MD 21550
  • Lots 14 & 17 Mallard Loop, Oakland, MD 21550
    Lots 14 & 17 Mallard Loop, Oakland, MD 21550
    Lots 14 & 17 Mallard Loop, Oakland, MD 21550
    /11

    $79,900 Sold Apr 04, 2025

    Lots 14 & 17 Mallard Loop, Oakland, MD 21550

    • Land
    • 1.07 Acres
    • $74,673 per Acre

    Last Sold Summary

    • 4 Days On Market

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

    Lots 14 & 17 Mallard Loop, Oakland, MD 21550

Showing Results 601 - 640, Page 16 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 © 2026 CoStar Group