10,731

Oakland, MD Homes

Section Image
  • 0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    /3

    $13,000 Sold Apr 14, 2025

    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550

    • Land
    • 2 Acres
    • $6,500 per Acre

    Last Sold Summary

    • 35 Days On Market

    Last Listing Agent Julie Mead The KW Collective

    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    • 1557 Mountainview Dr, Oakland, MD 21550
      1557 Mountainview Dr, Oakland, MD 21550
      1557 Mountainview Dr, Oakland, MD 21550
      /55

      Est $828,725 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,590 Sq Ft

      1557 Mountainview Dr, Oakland, MD 21550

      1557 Mountainview Dr, Oakland, MD 21550
  • 0 8th & Dennett Road St Unit MDGA2009886, Oakland, MD 21550
    0 8th & Dennett Road St Unit MDGA2009886, Oakland, MD 21550
    0 8th & Dennett Road St Unit MDGA2009886, Oakland, MD 21550
    /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 Vacations & Sales

    0 8th & Dennett Road St Unit MDGA2009886, Oakland, MD 21550
  • 216 Tarn Dr, Oakland, MD 21550
    216 Tarn Dr, Oakland, MD 21550
    216 Tarn Dr, Oakland, MD 21550
    /86

    $1,100,000 Sold Aug 27, 2025

    216 Tarn Dr, Oakland, MD 21550

    • 6 Beds
    • 4.5 Baths
    • 4,769 Sq Ft
    • Built 2020

    Last Sold Summary

    • $231/SF
    • 122 Days On Market

    Current Estimated Value $1,161,836

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

    216 Tarn Dr, Oakland, MD 21550
    • 106 H St, Oakland, MD 21550
      106 H St, Oakland, MD 21550
      106 H St, Oakland, MD 21550
      /91

      Est $306,483 Not Listed For Sale

      • 7 Beds
      • 3 Baths
      • 2,934 Sq Ft

      106 H St, Oakland, MD 21550

      106 H St, Oakland, MD 21550
  • 8946 Oakland Sang Run Rd, Oakland, MD 21550
    8946 Oakland Sang Run Rd, Oakland, MD 21550
    /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
  • 968 Hutton Rd, Oakland, MD 21550
    968 Hutton Rd, Oakland, MD 21550
    968 Hutton Rd, Oakland, MD 21550
    /38

    $265,000 Sold Dec 30, 2025

    968 Hutton Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 2012

    Last Sold Summary

    • $148/SF
    • 25 Days On Market

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

    968 Hutton Rd, Oakland, MD 21550
    • 25 Old Chestnut Dr, Oakland, MD 21550
      25 Old Chestnut Dr, Oakland, MD 21550
      25 Old Chestnut Dr, Oakland, MD 21550
      /63

      Est $2,905,415 Not Listed For Sale

      • 9 Beds
      • 9 Baths
      • 5,362 Sq Ft

      25 Old Chestnut Dr, Oakland, MD 21550

      25 Old Chestnut Dr, Oakland, MD 21550
  • 3416 Broadford Rd, Oakland, MD 21550
    3416 Broadford Rd, Oakland, MD 21550
    3416 Broadford Rd, Oakland, MD 21550
    /23

    $85,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,462 Sq Ft

    3416 Broadford Rd, Oakland, MD 21550

    Charming ranch-style cottage nestled in a beautiful, peaceful setting. This 3-bedroom, 1-bath home, situated on a 1.12-acre lot, features an enclosed porch, perfect for enjoying the surrounding nature year-round. A small natural run, Broadford Run, gently crosses the property, adding to the serene atmosphere. The property also offers a detached garage and a newer roof, providing a solid starting

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    3416 Broadford Rd, Oakland, MD 21550
  • 157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    /21

    $295,000 Sold Dec 23, 2025

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 752 Sq Ft
    • Built 1997

    Last Sold Summary

    • $392/SF
    • 21 Days On Market

    Last Listing Agent James Matthews Taylor Made Deep Creek Vacations & Sales

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    • 6663 Gorman Rd, Oakland, MD 21550
      6663 Gorman Rd, Oakland, MD 21550
      6663 Gorman Rd, Oakland, MD 21550
      /65

      Est $250,418 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,982 Sq Ft

      6663 Gorman Rd, Oakland, MD 21550

      6663 Gorman Rd, Oakland, MD 21550
  • 946 Glendale Rd, Oakland, MD 21550
    946 Glendale Rd, Oakland, MD 21550
    946 Glendale Rd, Oakland, MD 21550
    /100

    $1,765,000 Sold Mar 14, 2025

    946 Glendale Rd, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 3,546 Sq Ft
    • Built 2001

    Last Sold Summary

    • $498/SF
    • 16 Days On Market

    Current Estimated Value $1,772,515

    Last Listing Agent Jon Bell Railey Realty, Inc.

    946 Glendale Rd, Oakland, MD 21550
    • 10 Sunset Dr, Oakland, MD 21550
      10 Sunset Dr, Oakland, MD 21550
      10 Sunset Dr, Oakland, MD 21550
      /83

      Est $370,363 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,167 Sq Ft

      10 Sunset Dr, Oakland, MD 21550

      10 Sunset Dr, Oakland, MD 21550
  • 1567 Pergin Farm Rd, Oakland, MD 21550
    1567 Pergin Farm Rd, Oakland, MD 21550
    1567 Pergin Farm Rd, Oakland, MD 21550
    /67

    $1,542,000 Sold Nov 13, 2025

    1567 Pergin Farm Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,200 Sq Ft
    • Built 2002

    Last Sold Summary

    • $482/SF
    • 15 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1567 Pergin Farm Rd, Oakland, MD 21550
    • 601 E Oak St, Oakland, MD 21550
      601 E Oak St, Oakland, MD 21550
      601 E Oak St, Oakland, MD 21550
      /32

      Est $237,319 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,744 Sq Ft

      601 E Oak St, Oakland, MD 21550

      601 E Oak St, Oakland, MD 21550
  • 112 B St, Oakland, MD 21550
    112 B St, Oakland, MD 21550
    112 B St, Oakland, MD 21550
    /42

    $175,000 Sold Mar 21, 2025

    112 B St, Oakland, MD 21550

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

    Last Sold Summary

    • $182/SF
    • 23 Days On Market

    Current Estimated Value $176,535

    Last Listing Agent Thomas Long Railey Realty, Inc.

    112 B St, Oakland, MD 21550
    • 3416 Wilson Corona Rd, Oakland, MD 21550
      3416 Wilson Corona Rd, Oakland, MD 21550
      3416 Wilson Corona Rd, Oakland, MD 21550
      /78

      Est $307,290 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,936 Sq Ft

      3416 Wilson Corona Rd, Oakland, MD 21550

      3416 Wilson Corona Rd, Oakland, MD 21550
  • Lot 9 Pheasant Run, Oakland, MD 21550
    Lot 9 Pheasant Run, Oakland, MD 21550
    Lot 9 Pheasant Run, Oakland, MD 21550
    /10

    $59,000 Sold Jun 26, 2025

    Lot 9 Pheasant Run, Oakland, MD 21550

    • Land
    • 6.22 Acres
    • $9,486 per Acre

    Last Sold Summary

    • 15 Days On Market

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    Lot 9 Pheasant Run, Oakland, MD 21550
    • 38 Traders Ln, Oakland, MD 21550
      38 Traders Ln, Oakland, MD 21550
      38 Traders Ln, Oakland, MD 21550
      /47

      Est $557,946 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 2,582 Sq Ft

      38 Traders Ln, Oakland, MD 21550

      38 Traders Ln, Oakland, MD 21550
  • 36 Ridgewood Dr, Oakland, MD 21550
    36 Ridgewood Dr, Oakland, MD 21550
    36 Ridgewood Dr, Oakland, MD 21550
    /60

    $505,000 Sold Nov 14, 2025

    36 Ridgewood Dr, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 1,713 Sq Ft
    • Built 2000

    Last Sold Summary

    • $295/SF
    • 228 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    36 Ridgewood Dr, Oakland, MD 21550
    • 1983 Lake Shore Dr, Oakland, MD 21550
      1983 Lake Shore Dr, Oakland, MD 21550
      1983 Lake Shore Dr, Oakland, MD 21550
      /82

      Est $2,675,836 Not Listed For Sale

      • 5 Beds
      • 6.5 Baths
      • 4,074 Sq Ft

      1983 Lake Shore Dr, Oakland, MD 21550

      1983 Lake Shore Dr, Oakland, MD 21550
  • 1101 Wheeling Ave, Oakland, MD 21550
    1101 Wheeling Ave, Oakland, MD 21550
    1101 Wheeling Ave, Oakland, MD 21550
    /24

    $85,000 Sold Oct 03, 2025

    1101 Wheeling Ave, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,718 Sq Ft
    • Built 1950

    Last Sold Summary

    • $49/SF
    • 25 Days On Market

    Current Estimated Value $168,667

    Last Listing Agent Tanavia Greer Long & Foster Real Estate, Inc.

    1101 Wheeling Ave, Oakland, MD 21550
    • 1865 Paradise Point Rd, Oakland, MD 21550
      1865 Paradise Point Rd, Oakland, MD 21550
      1865 Paradise Point Rd, Oakland, MD 21550
      /76

      Est $1,033,539 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 2,158 Sq Ft

      1865 Paradise Point Rd, Oakland, MD 21550

      1865 Paradise Point Rd, Oakland, MD 21550
  • 110 W Pennington St, Oakland, MD 21550
    110 W Pennington St, Oakland, MD 21550
    110 W Pennington St, Oakland, MD 21550
    /24

    $110,000 Sold Sep 26, 2025

    110 W Pennington St, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1946

    Last Sold Summary

    • $143/SF
    • 12 Days On Market

    Current Estimated Value $113,172

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

    110 W Pennington St, Oakland, MD 21550
    • 227 W Liberty St, Oakland, MD 21550
      227 W Liberty St, Oakland, MD 21550
      227 W Liberty St, Oakland, MD 21550
      /39

      Est $219,298 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,232 Sq Ft

      227 W Liberty St, Oakland, MD 21550

      227 W Liberty St, Oakland, MD 21550
  • 414 D St, Oakland, MD 21550
    414 D St, Oakland, MD 21550
    414 D St, Oakland, MD 21550
    /45

    $150,000 Sold Aug 14, 2025

    414 D St, Oakland, MD 21550

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

    Last Sold Summary

    • $160/SF
    • 4 Days On Market

    Current Estimated Value $150,397

    Last Listing Agent Michelle Clark Taylor Made Deep Creek Vacations & Sales

    414 D St, Oakland, MD 21550
    • 889 Paradise Ridge Rd, Oakland, MD 21550
      889 Paradise Ridge Rd, Oakland, MD 21550
      889 Paradise Ridge Rd, Oakland, MD 21550
      /61

      Est $838,350 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,004 Sq Ft

      889 Paradise Ridge Rd, Oakland, MD 21550

      889 Paradise Ridge Rd, Oakland, MD 21550
  • 3554 Lake Shore Dr, Oakland, MD 21550
    3554 Lake Shore Dr, Oakland, MD 21550
    3554 Lake Shore Dr, Oakland, MD 21550
    /48

    $525,000 Sold Jul 11, 2025

    3554 Lake Shore Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1993

    Last Sold Summary

    • $405/SF
    • 232 Days On Market

    Current Estimated Value $531,727

    Last Listing Agent Robert Krop Keller Williams Realty Centre

    3554 Lake Shore Dr, Oakland, MD 21550
    • 255 Foster Rd, Oakland, MD 21550
      255 Foster Rd, Oakland, MD 21550
      255 Foster Rd, Oakland, MD 21550
      /84

      Est $328,269 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,272 Sq Ft

      255 Foster Rd, Oakland, MD 21550

      255 Foster Rd, Oakland, MD 21550
  • 142 Matthew Rd, Oakland, MD 21550
    142 Matthew Rd, Oakland, MD 21550
    142 Matthew 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
    • 324 W Liberty St, Oakland, MD 21550
      324 W Liberty St, Oakland, MD 21550
      324 W Liberty St, Oakland, MD 21550
      /64

      Est $241,897 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,725 Sq Ft

      324 W Liberty St, Oakland, MD 21550

      324 W Liberty St, Oakland, MD 21550
  • 104 G St, Oakland, MD 21550
    104 G St, Oakland, MD 21550
    104 G St, 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

    Last Listing Agent Julie Mead The KW Collective

    104 G St, Oakland, MD 21550
    • 2675 Stockslager Rd, Oakland, MD 21550
      2675 Stockslager Rd, Oakland, MD 21550
      2675 Stockslager Rd, Oakland, MD 21550
      /83

      Est $1,337,957 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,024 Sq Ft

      2675 Stockslager Rd, Oakland, MD 21550

      2675 Stockslager Rd, Oakland, MD 21550
  • 210 Seneca Ave, Oakland, MD 21550
    210 Seneca Ave, Oakland, MD 21550
    210 Seneca Ave, 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

    Last Listing Agent Andrew Orr The KW Collective

    210 Seneca Ave, Oakland, MD 21550
    • 630 Paradise Ridge Rd, Oakland, MD 21550
      630 Paradise Ridge Rd, Oakland, MD 21550
      630 Paradise Ridge Rd, Oakland, MD 21550
      /75

      Est $750,201 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,044 Sq Ft

      630 Paradise Ridge Rd, Oakland, MD 21550

      630 Paradise Ridge Rd, Oakland, MD 21550
  • 258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    /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 $562,641

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

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    • 111 W Liberty St, Oakland, MD 21550
      111 W Liberty St, Oakland, MD 21550
      111 W Liberty St, Oakland, MD 21550
      /4

      Est $74,357 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,528 Sq Ft

      111 W Liberty St, Oakland, MD 21550

      111 W Liberty St, Oakland, MD 21550
  • 114 Waterwheel Rd, Oakland, MD 21550
    114 Waterwheel Rd, Oakland, MD 21550
    114 Waterwheel Rd, Oakland, MD 21550
    /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 $238,631

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

    114 Waterwheel Rd, Oakland, MD 21550
    • 378 Lower Penn Point Dr, Oakland, MD 21550
      378 Lower Penn Point Dr, Oakland, MD 21550
      378 Lower Penn Point Dr, Oakland, MD 21550
      /25

      Est $1,131,610 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,114 Sq Ft

      378 Lower Penn Point Dr, Oakland, MD 21550

      378 Lower Penn Point Dr, Oakland, MD 21550
  • 142 Lemley Dr Unit I, Oakland, MD 21550
    142 Lemley Dr Unit I, Oakland, MD 21550
    142 Lemley Dr Unit I, Oakland, MD 21550
    /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 $405,653

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    142 Lemley Dr Unit I, Oakland, MD 21550

Showing Results 401 - 440, Page 11 of 18

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