10,714

Oakland, MD Homes

Section Image
  • 0 E Reese St, Oakland, MD 21550
    0 E Reese St, Oakland, MD 21550
    0 E Reese St, Oakland, MD 21550
    /4

    $12,000 Sold Sep 25, 2025

    0 E Reese St, Oakland, MD 21550

    • Land
    • 0.25 Acre
    • $48,000 per Acre

    Last Sold Summary

    • 4 Days On Market

    Last Listing Agent Thomas Long Railey Realty, Inc.

    0 E Reese St, Oakland, MD 21550
    • 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

    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

Showing Results 521 - 560, Page 14 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