10,771

Oakland, MD Homes

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  • 19956 Garrett Hwy Unit 6, Oakland, MD 21550
    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    /81

    $1,200,000

    Sold Jan 16, 2026

    19956 Garrett Hwy Unit 6, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 3,000 Sq Ft
    • Built 2007

    Last Sold Summary

    • $400/SF
    • 162 Days On Market

    Current Estimated Value $1,178,422

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    • 700 I St, Oakland, MD 21550
      700 I St, Oakland, MD 21550
      700 I St, Oakland, MD 21550
      /48

      Est $161,343

      Not Listed For Sale

      700 I St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,168 Sq Ft
      • Built 1960
      700 I St, Oakland, MD 21550

      Last Sold Summary

      • 7 Days On Market

  • 53 Bird Ave, Oakland, MD 21550
    53 Bird Ave, Oakland, MD 21550
    53 Bird Ave, Oakland, MD 21550
    /31

    $229,000

    $11K PRICE DROP Under Contract
    • 3 Beds
    • 3 Baths
    • 1,104 Sq Ft

    53 Bird Ave, Oakland, MD 21550

    Opportunity and a peaceful country setting on 1.55 acres in Deer Park. This 3BR, 2BA ranch offers 1,872 sq ft with solid bones and room to make it your own. The spacious kitchen with hickory cabinets, gas stove, and propane fireplace creates a warm gathering space at the heart of the home. Outside, several outbuildings—including a large shop and secondary wood shop with heat and electric, a

    Rachel Bruch Railey Realty, Inc.

    53 Bird Ave, Oakland, MD 21550
    • 409 M St, Oakland, MD 21550
      409 M St, Oakland, MD 21550
      409 M St, Oakland, MD 21550
      /29

      Est $181,297

      Not Listed For Sale

      409 M St, Oakland, MD 21550

      • 2 Beds
      • 2 Baths
      • 1,208 Sq Ft
      • Built 1950
      409 M St, Oakland, MD 21550

      Last Sold Summary

      • 28 Days On Market

  • 4 Laurel Brook Dr, Oakland, MD 21550
    4 Laurel Brook Dr, Oakland, MD 21550
    4 Laurel Brook Dr, Oakland, MD 21550
    /22

    $212,000

    Sold Dec 05, 2025

    4 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • Built 1989

    Last Sold Summary

    • 166 Days On Market

    Current Estimated Value $215,591

    Last Listing Agent Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    4 Laurel Brook Dr, Oakland, MD 21550
    • 513 K St, Oakland, MD 21550
      513 K St, Oakland, MD 21550
      513 K St, Oakland, MD 21550
      /36

      Est $120,500

      Not Listed For Sale

      513 K St, Oakland, MD 21550

      • 4 Beds
      • 1.5 Baths
      • 1,404 Sq Ft
      • Built 1900
      513 K St, Oakland, MD 21550

      Last Sold Summary

      • 46 Days On Market

  • 273 Glendale Rd, Oakland, MD 21550
    273 Glendale Rd, Oakland, MD 21550
    273 Glendale Rd, Oakland, MD 21550
    /74

    $2,450,000

    Sold Oct 30, 2025

    273 Glendale Rd, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 5,141 Sq Ft
    • Built 2008

    Last Sold Summary

    • $477/SF
    • 7 Days On Market

    Current Estimated Value $2,422,125

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

    273 Glendale Rd, 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

      Est $145,293

      Not Listed For Sale

      3941 Pleasant Valley Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,060 Sq Ft
      • Built 1900
      3941 Pleasant Valley Rd, Oakland, MD 21550

      Last Sold Summary

      • 82 Days On Market

  • 101 Sunset Dr, Oakland, MD 21550
    101 Sunset Dr, Oakland, MD 21550
    101 Sunset Dr, Oakland, MD 21550
    /66

    $499,000

    Sold Jul 15, 2025

    101 Sunset Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 3,024 Sq Ft
    • Built 1987

    Last Sold Summary

    • $165/SF
    • 11 Days On Market

    Current Estimated Value $451,456

    Last Listing Agent Rich Orr Railey Realty, Inc.

    101 Sunset Dr, Oakland, MD 21550
    • 242 Interlude Ln, Oakland, MD 21550
      242 Interlude Ln, Oakland, MD 21550
      242 Interlude Ln, Oakland, MD 21550
      /10

      Est $268,831

      Not Listed For Sale

      242 Interlude Ln, Oakland, MD 21550

      • 2 Beds
      • 2 Baths
      • 1,544 Sq Ft
      • Built 1997
      242 Interlude Ln, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

  • Lot 31 Fawn Dr, Oakland, MD 21550
    Lot 31 Fawn Dr, Oakland, MD 21550
    Lot 31 Fawn Dr, Oakland, MD 21550
    /24

    $17,000

    Sold Aug 22, 2025

    Lot 31 Fawn Dr, Oakland, MD 21550

    • Land
    • 30,056 Sq Ft
    • $24,638 per Acre

    Last Sold Summary

    • 19 Days On Market

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

    Lot 31 Fawn Dr, Oakland, MD 21550
    • 2078 Sanders Ln, Oakland, MD 21550
      2078 Sanders Ln, Oakland, MD 21550
      2078 Sanders Ln, Oakland, MD 21550
      /85

      Est $432,513

      Not Listed For Sale

      2078 Sanders Ln, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,904 Sq Ft
      • Built 1988
      2078 Sanders Ln, Oakland, MD 21550

      Last Sold Summary

      • 171 Days On Market

  • 0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    /4

    $115,000

    Sold Sep 26, 2025

    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550

    • Land
    • 22,651 Sq Ft
    • $221,154 per Acre

    Last Sold Summary

    • 32 Days On Market

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    0 Paradise Heights Rd Unit MDGA2010024, 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

      181 Glotfelty Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft
      • Built 2000
      181 Glotfelty Dr, Oakland, MD 21550

      Last Sold Summary

      • 22 Days On Market

  • 0 Longview Ln, Oakland, MD 21550
    0 Longview Ln, Oakland, MD 21550
    0 Longview Ln, Oakland, MD 21550
    /9

    $40,000

    Sold May 29, 2026

    0 Longview Ln, Oakland, MD 21550

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

    Last Sold Summary

    • 219 Days On Market

    Last Listing Agent Linda Deremer Appalachian Realty

    0 Longview Ln, 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

      Est $467,452

      Not Listed For Sale

      234 Maple Del Ln, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,750 Sq Ft
      • Built 1995
      234 Maple Del Ln, Oakland, MD 21550

      Last Sold Summary

      • 306 Days On Market

  • 170 Tannery Rd, Oakland, MD 21550
    170 Tannery Rd, Oakland, MD 21550
    170 Tannery Rd, Oakland, MD 21550
    /28

    $174,500

    Sold Oct 30, 2025

    170 Tannery Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft
    • Built 1974

    Last Sold Summary

    • $94/SF
    • 96 Days On Market

    Current Estimated Value $173,455

    Last Listing Agent Jonathan Minerick Homecoin.com

    170 Tannery Rd, Oakland, MD 21550
    • 367 Underwood Rd, Oakland, MD 21550
      367 Underwood Rd, Oakland, MD 21550
      367 Underwood Rd, Oakland, MD 21550
      /56

      Est $218,198

      Not Listed For Sale

      367 Underwood Rd, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 1,400 Sq Ft
      • Built 1986
      367 Underwood Rd, Oakland, MD 21550

      Last Sold Summary

      • 44 Days On Market

  • 202 Penelacre Ln, Oakland, MD 21550
    202 Penelacre Ln, Oakland, MD 21550
    202 Penelacre Ln, Oakland, MD 21550
    /85

    $975,000

    Sold Nov 24, 2025

    202 Penelacre Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • Built 1985

    Last Sold Summary

    • $592/SF
    • 12 Days On Market

    Current Estimated Value $956,202

    Last Listing Agent Justin Liller Railey Realty, Inc.

    202 Penelacre Ln, Oakland, MD 21550
    • 912 Snowy Creek Rd, Oakland, MD 21550
      912 Snowy Creek Rd, Oakland, MD 21550
      912 Snowy Creek Rd, Oakland, MD 21550
      /12

      Est $77,187

      Not Listed For Sale

      912 Snowy Creek Rd, Oakland, MD 21550

      • 4 Beds
      • 1 Bath
      • 1,482 Sq Ft
      • Built 1922
      912 Snowy Creek Rd, Oakland, MD 21550

      Last Sold Summary

      • 16 Days On Market

  • 870 Holy Cross Dr, Oakland, MD 21550
    870 Holy Cross Dr, Oakland, MD 21550
    870 Holy Cross Dr, Oakland, MD 21550
    /93

    $3,375,000

    Sold Nov 13, 2025

    870 Holy Cross Dr, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 5,681 Sq Ft
    • Built 2007

    Last Sold Summary

    • $594/SF
    • 5 Days On Market

    Current Estimated Value $3,365,037

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    870 Holy Cross Dr, Oakland, MD 21550
    • 920 Mayhew Inn Rd, Oakland, MD 21550
      920 Mayhew Inn Rd, Oakland, MD 21550
      920 Mayhew Inn Rd, Oakland, MD 21550
      /35

      Est $271,179

      Not Listed For Sale

      920 Mayhew Inn Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,314 Sq Ft
      • Built 1959
      920 Mayhew Inn Rd, Oakland, MD 21550

      Last Sold Summary

      • 1 Day On Market

  • 143 Manor Dr, Oakland, MD 21550
    143 Manor Dr, Oakland, MD 21550
    143 Manor Dr, Oakland, MD 21550
    /48

    $285,000

    Sold Feb 19, 2026

    143 Manor Dr, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 1,786 Sq Ft
    • Built 1977

    Last Sold Summary

    • 5% Below List Price
    • $160/SF
    • 2 Days On Market

    Current Estimated Value $288,409

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    143 Manor Dr, Oakland, MD 21550
    • 13873 Garrett Hwy, Oakland, MD 21550
      13873 Garrett Hwy, Oakland, MD 21550
      13873 Garrett Hwy, Oakland, MD 21550
      /24

      Est $182,334

      Not Listed For Sale

      13873 Garrett Hwy, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 2,472 Sq Ft
      • Built 1962
      13873 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 17 Days On Market

  • 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 $274,519

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    4012 Maryland Hwy, Oakland, MD 21550
    • 3900 Mayhew Inn Rd, Oakland, MD 21550
      3900 Mayhew Inn Rd, Oakland, MD 21550
      3900 Mayhew Inn Rd, Oakland, MD 21550
      /19

      Est $536,932

      Not Listed For Sale

      3900 Mayhew Inn Rd, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,160 Sq Ft
      • Built 1992
      3900 Mayhew Inn Rd, Oakland, MD 21550

      Last Sold Summary

      • 6 Days On Market

  • 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
    • 3821 Underwood Rd, Oakland, MD 21550
      3821 Underwood Rd, Oakland, MD 21550
      3821 Underwood Rd, Oakland, MD 21550
      /21

      Est $161,662

      Not Listed For Sale

      3821 Underwood Rd, Oakland, MD 21550

      • 4 Beds
      • 1 Bath
      • 1,232 Sq Ft
      • Built 1964
      3821 Underwood Rd, Oakland, MD 21550

      Last Sold Summary

      • 10 Days On Market

  • 41 Fox Den Rd, Oakland, MD 21550
    41 Fox Den Rd, Oakland, MD 21550
    41 Fox Den Rd, Oakland, MD 21550
    /25

    $215,000

    Sold Mar 20, 2026

    41 Fox Den Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,569 Sq Ft
    • Built 1940

    Last Sold Summary

    • 19% Below List Price
    • $137/SF
    • 310 Days On Market

    Current Estimated Value $328,778

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

    41 Fox Den Rd, Oakland, MD 21550
    • 198 Crellin Underwood Rd, Oakland, MD 21550
      198 Crellin Underwood Rd, Oakland, MD 21550
      198 Crellin Underwood Rd, Oakland, MD 21550
      /26

      Est $192,255

      Not Listed For Sale

      198 Crellin Underwood Rd, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1982
      198 Crellin Underwood Rd, Oakland, MD 21550

      Last Sold Summary

      • 59 Days On Market

  • 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

    Current Estimated Value $546,764

    Last Listing Agent Justin Liller Railey Realty, Inc.

    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    • 479 Underwood Rd, Oakland, MD 21550
      479 Underwood Rd, Oakland, MD 21550
      479 Underwood Rd, Oakland, MD 21550
      /70

      Est $266,045

      Not Listed For Sale

      479 Underwood Rd, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,944 Sq Ft
      • Built 1961
      479 Underwood Rd, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

  • 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 $329,984

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    206 N 10th St, Oakland, MD 21550
    • 450 Fern Dr, Oakland, MD 21550
      450 Fern Dr, Oakland, MD 21550
      450 Fern Dr, Oakland, MD 21550
      /36

      Est $270,589

      Not Listed For Sale

      450 Fern Dr, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 861 Sq Ft
      • Built 1967
      450 Fern Dr, Oakland, MD 21550

      Last Sold Summary

      • 152 Days On Market

  • 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 $935,612

    Last Listing Agent Amy Grubby AEK Real Estate, LLC

    111 Tarn Dr, Oakland, MD 21550
    • 377 Fingerboard Rd, Oakland, MD 21550
      377 Fingerboard Rd, Oakland, MD 21550
      377 Fingerboard Rd, Oakland, MD 21550
      /78

      Est $495,872

      Not Listed For Sale

      377 Fingerboard Rd, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,824 Sq Ft
      • Built 1970
      377 Fingerboard Rd, Oakland, MD 21550

      Last Sold Summary

      • 44 Days On Market

  • 18025B Garrett Hwy Unit B, Oakland, MD 21550
    18025B Garrett Hwy Unit B, Oakland, MD 21550
    18025B Garrett Hwy Unit B, Oakland, MD 21550
    /54

    $425,000

    Sold May 15, 2026

    18025B Garrett Hwy Unit B, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • Built 2006

    Last Sold Summary

    • $221/SF
    • 3 Days On Market

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

    18025B Garrett Hwy Unit B, Oakland, MD 21550
    • 195 Fingerboard Rd, Oakland, MD 21550
      195 Fingerboard Rd, Oakland, MD 21550
      195 Fingerboard Rd, Oakland, MD 21550
      /67

      Est $180,968

      Not Listed For Sale

      195 Fingerboard Rd, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,613 Sq Ft
      • Built 1943
      195 Fingerboard Rd, Oakland, MD 21550

      Last Sold Summary

      • 184 Days On Market

  • 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

    Current Estimated Value $717,267

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

    465 Pergin Farm Rd, Oakland, MD 21550
    • 3931 Hutton Rd, Oakland, MD 21550
      3931 Hutton Rd, Oakland, MD 21550
      3931 Hutton Rd, Oakland, MD 21550
      /70

      Est $187,312

      Not Listed For Sale

      3931 Hutton Rd, Oakland, MD 21550

      • 2 Beds
      • 1.5 Baths
      • 1,104 Sq Ft
      • Built 1972
      3931 Hutton Rd, Oakland, MD 21550

      Last Sold Summary

      • 15 Days On Market

Showing Results 641 - 680, Page 17 of 18

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