10,739

Oakland, MD Homes

Section Image
    • /65

      Est $154,270 Not Listed For Sale

      94 Tannery Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,108 Sq Ft
      • Built 1900
      94 Tannery Rd, Oakland, MD 21550

      Last Sold Summary

      • 34% Above List Price
      • $104/SF
      • 63 Days On Market

      Last Sold Price $115,000

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /24

    $619,900 Pending

    • 4 Beds
    • 4 Baths
    • 2,550 Sq Ft

    66 Paradise Ridge Rd, Oakland, MD 21550

    Welcome to 66 Paradise Ridge Rd, a charming single-familyhome in the picturesque town of Oakland, MD. LAKE ACCESS WITH DEEDED DOCK. Builtin 1984, this two-story residence offers a spacious layout with 4 bathrooms and 2,550square feet of finished living space. Situated on a generous 21,780-square-foot lot, theproperty provides plenty of room to roam and enjoy the natural

    Joseph Hawkins Hawkins Real Estate Company

    66 Paradise Ridge Rd, Oakland, MD 21550
  • /5

    $44,000 Sold Aug 11, 2025

    142 Matthew Rd, Oakland, MD 21550

    • Land
    • 1.83 Acres
    • $24,044 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    142 Matthew Rd, Oakland, MD 21550
    • /66

      Est $192,056 Not Listed For Sale

      1606 Wheeling Ave, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,502 Sq Ft
      • Built 1976
      1606 Wheeling Ave, Oakland, MD 21550

      Last Sold Summary

      • 9% Below List Price
      • $140/SF
      • 2 Days On Market

      Last Sold Price $211,000

      Last Listing Agent Kevin Liller Railey Realty, Inc.

  • /15

    $199,900

    • Land
    • 9.64 Acres
    • $20,737 per Acre

    0 8th & Dennett Road St Unit MDGA2009886, Oakland, MD 21550

    A rare opportunity to acquire a high-potential 9.64 acre parcel located in the heart of Oakland. The location is very close to schools, grocery stores, restaurants, hospital and shopping. This site offers an ideal setting for residential, mixed-use, multifamily, or commercial development (subject to zoning approval). Easy access to infrastructure, with public utilities nearby at the street. This

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    0 8th & Dennett Road St Unit MDGA2009886, Oakland, MD 21550
  • /48

    $229,000 Sold Dec 15, 2025

    104 G St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft
    • Built 1900

    Last Sold Summary

    • $142/SF
    • 26 Days On Market

    Current Estimated Value $225,689

    Last Listing Agent Julie Mead The KW Collective

    104 G St, Oakland, MD 21550
    • /24

      Est $216,149 Not Listed For Sale

      123 Spruce St, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,392 Sq Ft
      • Built 1990
      123 Spruce St, Oakland, MD 21550

      Last Sold Summary

      • 1% Above List Price
      • $154/SF
      • 7 Days On Market

      Last Sold Price $215,000

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

  • /2

    $369,000

    • Land
    • 0.47 Acre
    • $785,106 per Acre

    8946 Oakland Sang Run Rd, Oakland, MD 21550

    There are 3 adjacent parcels included with this sale :Tax ID - 1206034144, 1206020860, 1206007082 All parcels together are 8 acres WARNING: The house on this property is condemned and ready for tear down. Enter at your own risk.

    Joe Zorzit Eagle Commercial Realty

    8946 Oakland Sang Run Rd, Oakland, MD 21550
  • /20

    $195,000 Sold Nov 12, 2025

    210 Seneca Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,204 Sq Ft
    • Built 1996

    Last Sold Summary

    • $162/SF
    • 2 Days On Market

    Current Estimated Value $197,321

    Last Listing Agent Andrew Orr The KW Collective

    210 Seneca Ave, Oakland, MD 21550
    • /69

      Est $882,227 Not Listed For Sale

      79 Hummingbird Ct, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,800 Sq Ft
      • Built 1999
      79 Hummingbird Ct, Oakland, MD 21550

      Last Sold Summary

      • 22% Above List Price
      • $259/SF
      • 59 Days On Market

      Last Sold Price $725,000

      Last Listing Agent Jessie Railey Railey Realty, Inc.

  • /40

    $560,000 Sold Jun 20, 2025

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2009

    Last Sold Summary

    • $170/SF
    • 52 Days On Market

    Current Estimated Value $558,057

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

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    • /32

      Est $736,191 Not Listed For Sale

      1118 Lake Shore Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,446 Sq Ft
      • Built 1994
      1118 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 16% Above List Price
      • $260/SF
      • 3 Days On Market

      Last Sold Price $635,000

      Last Listing Agent Eric Crawford Taylor Made Deep Creek Real Estate

  • /32

    $232,500 Sold Jul 10, 2025

    114 Waterwheel Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1965

    Last Sold Summary

    • $242/SF
    • 138 Days On Market

    Current Estimated Value $246,561

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Real Estate

    114 Waterwheel Rd, Oakland, MD 21550
    • /86

      Est $863,516 Not Listed For Sale

      105 Meadow Ct, Oakland, MD 21550

      • 4 Beds
      • 6 Baths
      • 3,192 Sq Ft
      • Built 2004
      105 Meadow Ct, Oakland, MD 21550

      Last Sold Summary

      • 17% Above List Price
      • $231/SF
      • 47 Days On Market

      Last Sold Price $737,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /26

    $400,000 Sold Apr 21, 2025

    142 Lemley Dr Unit I, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • Built 1987

    Last Sold Summary

    • 146 Days On Market

    Current Estimated Value $399,590

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    142 Lemley Dr Unit I, Oakland, MD 21550
    • /59

      Est $434,011 Not Listed For Sale

      57 Allegro Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,524 Sq Ft
      • Built 2004
      57 Allegro Ln, Oakland, MD 21550

      Last Sold Summary

      • 13% Above List Price
      • $153/SF
      • 67 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Chris Nichols Taylor Made Deep Creek Real Estate

  • /26

    $237,500 Sold Apr 15, 2025

    11 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • Built 1989

    Last Sold Summary

    • 157 Days On Market

    Current Estimated Value $259,283

    Last Listing Agent Dan Shockey Taylor Made Deep Creek Real Estate

    11 Laurel Brook Dr, Oakland, MD 21550
    • /73

      Est $635,993 Not Listed For Sale

      491 Edens Ridge Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 3,318 Sq Ft
      • Built 2003
      491 Edens Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 18% Above List Price
      • $163/SF
      • 9 Days On Market

      Last Sold Price $540,000

      Last Listing Agent Julie Mead The KW Collective

  • /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 $1,164,119

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    636 Paradise Heights, Oakland, MD 21550
    • /49

      Est $360,513 Not Listed For Sale

      19398 Garrett Hwy, Oakland, MD 21550

      • 5 Beds
      • 2 Baths
      • 2,414 Sq Ft
      • Built 1940
      19398 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 22% Above List Price
      • $122/SF
      • 168 Days On Market

      Last Sold Price $295,000

      Last Listing Agent Chris Nichols Taylor Made Deep Creek Real Estate

  • /38

    $100,000 Sold Jul 11, 2025

    5914 Maryland Hwy, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,775 Sq Ft
    • Built 1973

    Last Sold Summary

    • $56/SF
    • 4 Days On Market

    Current Estimated Value $180,876

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Real Estate

    5914 Maryland Hwy, Oakland, MD 21550
    • /33

      Est $238,864 Not Listed For Sale

      1070 Sunrise Dr, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,144 Sq Ft
      • Built 1988
      1070 Sunrise Dr, Oakland, MD 21550

      Last Sold Summary

      • 17% Above List Price
      • $96/SF
      • 3 Days On Market

      Last Sold Price $205,000

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

  • /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 $199,582

    Last Listing Agent Jon Bell Railey Realty, Inc.

    4643 Oakland Sang Run Rd, Oakland, MD 21550
    • /45

      Est $191,645 Not Listed For Sale

      607 L St, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,920 Sq Ft
      • Built 1980
      607 L St, Oakland, MD 21550

      Last Sold Summary

      • 24% Above List Price
      • $81/SF
      • 13 Days On Market

      Last Sold Price $155,000

      Last Listing Agent Duane Stein II Keller Williams Realty Centre

  • /45

    $750,000 Sold Jan 16, 2026

    198 Grandview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,744 Sq Ft
    • Built 2003

    Last Sold Summary

    • $273/SF
    • 150 Days On Market

    Current Estimated Value $778,208

    Last Listing Agent Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, MD 21550
    • /48

      Est $454,234 Not Listed For Sale

      482 Pergin Farm Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 2,160 Sq Ft
      • Built 1980
      482 Pergin Farm Rd, Oakland, MD 21550

      Last Sold Summary

      • 17% Above List Price
      • $180/SF
      • 128 Days On Market

      Last Sold Price $389,500

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /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

    Current Estimated Value $564,465

    Last Listing Agent Larry Smith Railey Realty, Inc.

    72 Cliff Dr, Oakland, MD 21550
    • /46

      Est $1,405,192 Not Listed For Sale

      2127 Lake Shore Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,546 Sq Ft
      • Built 1960
      2127 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 5% Below List Price
      • $579/SF
      • 20 Days On Market

      Last Sold Price $1,475,000

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

  • /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

    Current Estimated Value $385,075

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

    113 G St, Oakland, MD 21550
    • /97

      Est $2,457,780 Not Listed For Sale

      1738 Paradise Point Rd, Oakland, MD 21550

      • 7 Beds
      • 5.5 Baths
      • 4,260 Sq Ft
      • Built 2002
      1738 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 14% Above List Price
      • $505/SF
      • 127 Days On Market

      Last Sold Price $2,150,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /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 $189,046

    Last Listing Agent Tim Macauley Taylor Made Deep Creek Real Estate

    1681 Shady Dell Rd, Oakland, MD 21550
    • /78

      Est $221,947 Not Listed For Sale

      1400 Oakland Ave, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 1972
      1400 Oakland Ave, Oakland, MD 21550

      Last Sold Summary

      • 1% Above List Price
      • $115/SF
      • 8 Days On Market

      Last Sold Price $219,900

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /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 Real Estate

    28 Wild Turkey Ln, Oakland, MD 21550
    • /69

      Est $472,091 Not Listed For Sale

      1014 Madison St, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 3,016 Sq Ft
      • Built 1988
      1014 Madison St, Oakland, MD 21550

      Last Sold Summary

      • 5% Above List Price
      • $149/SF
      • 21 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /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 $476,004

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

    234 Maple Del Ln, Oakland, MD 21550
    • /24

      Est $699,359 Not Listed For Sale

      8 Arrowhead Ln, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • Built 1988
      8 Arrowhead Ln, Oakland, MD 21550

      Last Sold Summary

      • 7% Below List Price
      • 80 Days On Market

      Last Sold Price $750,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /34

    $275,000 Sold Jan 02, 2026

    34 Laurel Brook Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1992

    Last Sold Summary

    • 13 Days On Market

    Current Estimated Value $315,432

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Real Estate

    34 Laurel Brook Dr, Oakland, MD 21550
    • /88

      Est $473,409 Not Listed For Sale

      189 Whistle Pig Way, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,777 Sq Ft
      • Built 1998
      189 Whistle Pig Way, Oakland, MD 21550

      Last Sold Summary

      • 14% Above List Price
      • $234/SF
      • 4 Days On Market

      Last Sold Price $415,000

      Last Listing Agent Debra Savage Railey Realty, Inc.

  • /48

    $205,000 Sold Mar 20, 2026

    565 Glendale Rd Unit 312, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft
    • Built 2006

    Last Sold Summary

    • 10% Below List Price
    • $261/SF
    • 6 Days On Market

    Current Estimated Value $292,039

    Last Listing Agent Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 312, Oakland, MD 21550
    • /80

      Est $1,434,027 Not Listed For Sale

      2236 Paradise Point Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,004 Sq Ft
      • Built 1956
      2236 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 10% Below List Price
      • $798/SF
      • 2 Days On Market

      Last Sold Price $1,599,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

Showing Results 441 - 480, Page 12 of 18

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