10,771

Oakland, MD Homes

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  • 313 W Liberty St, Oakland, MD 21550
    313 W Liberty St, Oakland, MD 21550
    313 W Liberty St, Oakland, MD 21550
    /59

    $210,000

    Sold May 06, 2026

    313 W Liberty St, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,064 Sq Ft
    • Built 1947

    Last Sold Summary

    • 5% Below List Price
    • $197/SF
    • 39 Days On Market

    Current Estimated Value $213,923

    Last Listing Agent Justin Liller Railey Realty, Inc.

    313 W Liberty St, Oakland, MD 21550
    • 1262 Memorial Dr, Oakland, MD 21550
      1262 Memorial Dr, Oakland, MD 21550
      1262 Memorial Dr, Oakland, MD 21550
      /55

      Est $354,732

      Not Listed For Sale

      1262 Memorial Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,345 Sq Ft
      • Built 1992
      1262 Memorial Dr, Oakland, MD 21550

      Last Sold Summary

      • 95 Days On Market

  • 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 $971,414

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

    267 Woodlands Hill Ln, Oakland, MD 21550
    • 600 S 3rd St, Oakland, MD 21550
      600 S 3rd St, Oakland, MD 21550
      600 S 3rd St, Oakland, MD 21550
      /42

      Est $248,260

      Not Listed For Sale

      600 S 3rd St, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,890 Sq Ft
      • Built 1955
      600 S 3rd St, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • 621 Paradise Heights, Oakland, MD 21550
    621 Paradise Heights, Oakland, MD 21550
    621 Paradise Heights, Oakland, MD 21550
    /107

    $575,000

    Sold Apr 30, 2026

    621 Paradise Heights, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 3,242 Sq Ft
    • Built 1988

    Last Sold Summary

    • 25% Below List Price
    • $177/SF
    • 502 Days On Market

    Current Estimated Value $654,420

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

    621 Paradise Heights, Oakland, MD 21550
    • 112 E Pennington St, Oakland, MD 21550
      112 E Pennington St, Oakland, MD 21550
      112 E Pennington St, Oakland, MD 21550
      /4

      Est $130,509

      Not Listed For Sale

      112 E Pennington St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,380 Sq Ft
      • Built 1916
      112 E Pennington St, Oakland, MD 21550

      Last Sold Summary

      • 1 Day On Market

  • 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 $2,693,188

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    1100 S Blakeslee Rd, Oakland, MD 21550
    • 305 Crook Crest Rd, Oakland, MD 21550
      305 Crook Crest Rd, Oakland, MD 21550
      305 Crook Crest Rd, Oakland, MD 21550
      /51

      Est $406,261

      Not Listed For Sale

      305 Crook Crest Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 2,800 Sq Ft
      • Built 1891
      305 Crook Crest Rd, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

  • 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

    Current Estimated Value $558,250

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    346 Skippers Point Rd, Oakland, MD 21550
    • 309 Woodland Dr, Oakland, MD 21550
      309 Woodland Dr, Oakland, MD 21550
      309 Woodland Dr, Oakland, MD 21550
      /56

      Est $265,678

      Not Listed For Sale

      309 Woodland Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,184 Sq Ft
      • Built 1970
      309 Woodland Dr, Oakland, MD 21550

      Last Sold Summary

      • 8 Days On Market

  • 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

    Current Estimated Value $549,616

    Last Listing Agent Jon Bell Railey Realty, Inc.

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    • 219 W Liberty St, Oakland, MD 21550
      219 W Liberty St, Oakland, MD 21550
      219 W Liberty St, Oakland, MD 21550
      /31

      Est $216,667

      Not Listed For Sale

      219 W Liberty St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,360 Sq Ft
      • Built 1925
      219 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 185 Days On Market

  • 139 Overlook Ridge Dr, Oakland, MD 21550
    139 Overlook Ridge Dr, Oakland, MD 21550
    139 Overlook Ridge Dr, Oakland, MD 21550
    /72

    $835,000

    Sold Mar 27, 2026

    139 Overlook Ridge Dr, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,846 Sq Ft
    • Built 2004

    Last Sold Summary

    • $293/SF
    • 340 Days On Market

    Current Estimated Value $812,095

    Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    139 Overlook Ridge Dr, Oakland, MD 21550
    • 413 N 2nd St, Oakland, MD 21550
      413 N 2nd St, Oakland, MD 21550
      413 N 2nd St, Oakland, MD 21550
      /98

      Est $339,429

      Not Listed For Sale

      413 N 2nd St, Oakland, MD 21550

      • 5 Beds
      • 2.5 Baths
      • 3,472 Sq Ft
      • Built 1962
      413 N 2nd St, Oakland, MD 21550

      Last Sold Summary

      • 10 Days On Market

  • 711 Heritage Dr, Oakland, MD 21550
    711 Heritage Dr, Oakland, MD 21550
    711 Heritage Dr, Oakland, MD 21550
    /58

    $249,000

    Sold Mar 20, 2026

    711 Heritage Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2000

    Last Sold Summary

    • $178/SF
    • 6 Days On Market

    Current Estimated Value $249,373

    Last Listing Agent Rich Orr Railey Realty, Inc.

    711 Heritage Dr, Oakland, MD 21550
    • 132 N 8th St, Oakland, MD 21550
      132 N 8th St, Oakland, MD 21550
      132 N 8th St, Oakland, MD 21550
      /69

      Est $232,105

      Not Listed For Sale

      132 N 8th St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,248 Sq Ft
      • Built 1940
      132 N 8th St, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

  • 1056 Sunrise Dr, Oakland, MD 21550
    1056 Sunrise Dr, Oakland, MD 21550
    1056 Sunrise Dr, Oakland, MD 21550
    /60

    $280,000

    Sold Nov 14, 2025

    1056 Sunrise Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 1,528 Sq Ft
    • Built 1976

    Last Sold Summary

    • $183/SF
    • 59 Days On Market

    Current Estimated Value $269,967

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

    1056 Sunrise Dr, Oakland, MD 21550
    • 514 E Alder St, Oakland, MD 21550
      514 E Alder St, Oakland, MD 21550
      514 E Alder St, Oakland, MD 21550
      /36

      Est $242,697

      Not Listed For Sale

      514 E Alder St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,152 Sq Ft
      • Built 1928
      514 E Alder St, Oakland, MD 21550

      Last Sold Summary

      • 22 Days On Market

  • 1544 Stockslager Rd, Oakland, MD 21550
    1544 Stockslager Rd, Oakland, MD 21550
    1544 Stockslager Rd, Oakland, MD 21550
    /63

    $1,750,000

    Sold May 20, 2026

    1544 Stockslager Rd, Oakland, MD 21550

    • 5 Beds
    • 4 Baths
    • 3,456 Sq Ft
    • Built 1979

    Last Sold Summary

    • $506/SF
    • 6 Days On Market

    Current Estimated Value $1,722,226

    Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    1544 Stockslager Rd, Oakland, MD 21550
    • 1400 Wheeling Ave, Oakland, MD 21550
      1400 Wheeling Ave, Oakland, MD 21550
      1400 Wheeling Ave, Oakland, MD 21550
      /21

      Not Listed For Sale

      1400 Wheeling Ave, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1990
      1400 Wheeling Ave, Oakland, MD 21550

      Last Sold Summary

      • 27 Days On Market

  • 226 N Hammond St, Oakland, MD 21550
    226 N Hammond St, Oakland, MD 21550
    /2

    $276,000

    Sold May 08, 2026

    226 N Hammond St, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Built 2026

    Last Sold Summary

    • 5% Below List Price
    • $276/SF
    • 39 Days On Market

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    226 N Hammond St, Oakland, MD 21550
    • 1405 Wheeling Ave, Oakland, MD 21550
      1405 Wheeling Ave, Oakland, MD 21550
      1405 Wheeling Ave, Oakland, MD 21550
      /67

      Est $204,002

      Not Listed For Sale

      1405 Wheeling Ave, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,530 Sq Ft
      • Built 1992
      1405 Wheeling Ave, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

  • Lot #5 Swan Meadow Dr, Oakland, MD 21550
    Lot #5 Swan Meadow Dr, Oakland, MD 21550
    Lot #5 Swan Meadow Dr, Oakland, MD 21550
    /5

    $135,000

    Sold Jun 25, 2025

    Lot #5 Swan Meadow Dr, Oakland, MD 21550

    • Land
    • 10 Acres
    • $13,500 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    Lot #5 Swan Meadow Dr, Oakland, MD 21550
    • 204 D St, Oakland, MD 21550
      204 D St, Oakland, MD 21550
      204 D St, Oakland, MD 21550
      /19

      Est $134,276

      Not Listed For Sale

      204 D St, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1973
      204 D St, Oakland, MD 21550

      Last Sold Summary

      • 216 Days On Market

  • 1087 Pergin Farm Rd, Oakland, MD 21550
    1087 Pergin Farm Rd, Oakland, MD 21550
    1087 Pergin Farm Rd, Oakland, MD 21550
    /149

    $2,975,000

    Sold Oct 03, 2025

    1087 Pergin Farm Rd, Oakland, MD 21550

    • 6 Beds
    • 5.5 Baths
    • 4,481 Sq Ft
    • Built 1984

    Last Sold Summary

    • $664/SF
    • 16 Days On Market

    Current Estimated Value $2,957,251

    Last Listing Agent Susan Bell Railey Realty, Inc.

    1087 Pergin Farm Rd, Oakland, MD 21550
    • 132 Hillside Dr, Oakland, MD 21550
      132 Hillside Dr, Oakland, MD 21550
      132 Hillside Dr, Oakland, MD 21550
      /61

      Est $256,467

      Not Listed For Sale

      132 Hillside Dr, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,488 Sq Ft
      • Built 1964
      132 Hillside Dr, Oakland, MD 21550

      Last Sold Summary

      • 12 Days On Market

  • Lot 9 Birchwood Dr, Oakland, MD 21550
    Lot 9 Birchwood Dr, Oakland, MD 21550
    Lot 9 Birchwood Dr, Oakland, MD 21550
    /23

    $18,000

    Sold Jul 03, 2025

    Lot 9 Birchwood Dr, Oakland, MD 21550

    • Land
    • 34,848 Sq Ft
    • $22,500 per Acre

    Last Sold Summary

    • 5 Days On Market

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

    Lot 9 Birchwood Dr, Oakland, MD 21550
    • 1306 Wheeling Ave, Oakland, MD 21550
      1306 Wheeling Ave, Oakland, MD 21550
      1306 Wheeling Ave, Oakland, MD 21550
      /22

      Est $270,771

      Not Listed For Sale

      1306 Wheeling Ave, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,624 Sq Ft
      • Built 1960
      1306 Wheeling Ave, Oakland, MD 21550

      Last Sold Summary

      • 77 Days On Market

  • 30 Village Dr Unit 3, Oakland, MD 21550
    30 Village Dr Unit 3, Oakland, MD 21550
    30 Village Dr Unit 3, Oakland, MD 21550
    /35

    $390,000

    Sold Dec 12, 2025

    30 Village Dr Unit 3, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 916 Sq Ft
    • Built 2005

    Last Sold Summary

    • $426/SF
    • 34 Days On Market

    Current Estimated Value $379,551

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    30 Village Dr Unit 3, Oakland, MD 21550
    • 410 K St, Oakland, MD 21550
      410 K St, Oakland, MD 21550
      410 K St, Oakland, MD 21550
      /21

      Est $137,185

      Not Listed For Sale

      410 K St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,440 Sq Ft
      • Built 1900
      410 K St, Oakland, MD 21550

      Last Sold Summary

      • 21 Days On Market

  • 422 Underwood Rd, Oakland, MD 21550
    422 Underwood Rd, Oakland, MD 21550
    422 Underwood Rd, Oakland, MD 21550
    /45

    $195,000

    Sold Jul 11, 2025

    422 Underwood Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1972

    Last Sold Summary

    • $203/SF
    • 17 Days On Market

    Current Estimated Value $190,054

    Last Listing Agent Larry Smith Railey Realty, Inc.

    422 Underwood Rd, Oakland, MD 21550
    • 1100 Oakland Ave, Oakland, MD 21550
      1100 Oakland Ave, Oakland, MD 21550
      1100 Oakland Ave, Oakland, MD 21550
      /25

      Est $197,296

      Not Listed For Sale

      1100 Oakland Ave, Oakland, MD 21550

      • 5 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 1900
      1100 Oakland Ave, Oakland, MD 21550

      Last Sold Summary

      • 90 Days On Market

  • 2360 Garrett Rd, Oakland, MD 21550
    2360 Garrett Rd, Oakland, MD 21550
    /2

    $285,000

    Sold Sep 05, 2025

    2360 Garrett Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Built 2016

    Last Sold Summary

    • $271/SF
    • 0 Days On Market

    Current Estimated Value $286,096

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    2360 Garrett Rd, Oakland, MD 21550
    • 1107 Oakland Ave, Oakland, MD 21550
      1107 Oakland Ave, Oakland, MD 21550
      1107 Oakland Ave, Oakland, MD 21550
      /42

      Est $148,398

      Not Listed For Sale

      1107 Oakland Ave, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,152 Sq Ft
      • Built 1950
      1107 Oakland Ave, Oakland, MD 21550

      Last Sold Summary

      • 70 Days On Market

  • 355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    /70

    $610,000

    Sold May 19, 2026

    355 Lonesome Pine Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 4,720 Sq Ft
    • Built 2010

    Last Sold Summary

    • 16% Above List Price
    • $129/SF
    • 34 Days On Market

    Current Estimated Value $514,955

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    355 Lonesome Pine Rd, Oakland, MD 21550
    • 501 Spruce St, Oakland, MD 21550
      501 Spruce St, Oakland, MD 21550
      501 Spruce St, Oakland, MD 21550
      /42

      Est $210,491

      Not Listed For Sale

      501 Spruce St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,176 Sq Ft
      • Built 1978
      501 Spruce St, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • 2805 Shady Dell Rd, Oakland, MD 21550
    2805 Shady Dell Rd, Oakland, MD 21550
    2805 Shady Dell Rd, Oakland, MD 21550
    /47

    $208,550

    Sold Sep 26, 2025

    2805 Shady Dell Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1966

    Last Sold Summary

    • $143/SF
    • 42 Days On Market

    Current Estimated Value $214,441

    Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    2805 Shady Dell Rd, 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

      13 Hazel Glade Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2000
      13 Hazel Glade Dr, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • 197 Black Angus Dr, Oakland, MD 21550
    197 Black Angus Dr, Oakland, MD 21550
    197 Black Angus Dr, Oakland, MD 21550
    /111

    $2,600,000

    Sold Oct 20, 2025

    197 Black Angus Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,156 Sq Ft
    • Built 1975

    Last Sold Summary

    • $626/SF
    • 15 Days On Market

    Current Estimated Value $2,606,135

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    197 Black Angus Dr, 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

      318 Allegheny Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1995
      318 Allegheny Dr, Oakland, MD 21550

      Last Sold Summary

      • 152 Days On Market

Showing Results 601 - 640, Page 16 of 18

Maryland Garrett County Oakland

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