10,714

Oakland, MD Homes

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  • 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
    • 375 Glendale Rd, Oakland, MD 21550
      375 Glendale Rd, Oakland, MD 21550
      375 Glendale Rd, Oakland, MD 21550
      /54

      Est $2,459,781 Not Listed For Sale

      • 8 Beds
      • 6.5 Baths
      • 5,638 Sq Ft

      375 Glendale Rd, Oakland, MD 21550

      375 Glendale Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit 116, Oakland, MD 21550
    565 Glendale Rd Unit 116, Oakland, MD 21550
    565 Glendale Rd Unit 116, Oakland, MD 21550
    /29

    $169,000

    • 1 Bed
    • 1 Bath
    • 484 Sq Ft

    565 Glendale Rd Unit 116, Oakland, MD 21550

    Don't miss this rare opportunity to own a beautifully updated 1-bedroom unit at Silver Tree Suites on Deep Creek Lake! This turn-key condo features recent upgrades and is being sold fully furnished, making it perfect as a vacation getaway or income-generating rental. The unit boasts a solid rental history, offering immediate investment potential. Enjoy access to a wide range of on-site amenities,

    Nina Beitzel Railey Realty, Inc.

    565 Glendale Rd Unit 116, 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 $175,511

    Last Listing Agent Thomas Long Railey Realty, Inc.

    112 B St, Oakland, MD 21550
    • 9 Laurel Brook Dr, Oakland, MD 21550
      9 Laurel Brook Dr, Oakland, MD 21550
      9 Laurel Brook Dr, Oakland, MD 21550
      /18

      Est $249,177 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,200 Sq Ft

      9 Laurel Brook Dr, Oakland, MD 21550

      9 Laurel Brook Dr, Oakland, MD 21550
  • 66 Paradise Ridge Rd, Oakland, MD 21550
    66 Paradise Ridge Rd, Oakland, MD 21550
    66 Paradise Ridge Rd, Oakland, MD 21550
    /24

    $619,900

    • 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
  • 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
    • 1557 Mountainview Dr, Oakland, MD 21550
      1557 Mountainview Dr, Oakland, MD 21550
      1557 Mountainview Dr, Oakland, MD 21550
      /55

      Est $818,297 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
  • 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
    • 106 H St, Oakland, MD 21550
      106 H St, Oakland, MD 21550
      106 H St, Oakland, MD 21550
      /91

      Est $297,319 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
  • 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

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

    1101 Wheeling Ave, 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 $2,773,006 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
  • 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

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

    110 W Pennington St, Oakland, MD 21550
    • 6663 Gorman Rd, Oakland, MD 21550
      6663 Gorman Rd, Oakland, MD 21550
      6663 Gorman Rd, Oakland, MD 21550
      /65

      Est $246,815 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
  • 2 E Center St, Oakland, MD 21550
    2 E Center St, Oakland, MD 21550
    2 E Center St, Oakland, MD 21550
    /17

    $114,000 Sold Jan 30, 2025

    2 E Center St, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1910

    Last Sold Summary

    • $74/SF
    • 63 Days On Market

    Current Estimated Value $129,935

    Last Listing Agent Tim Macauley Taylor Made Deep Creek Vacations & Sales

    2 E Center St, Oakland, MD 21550
    • 10 Sunset Dr, Oakland, MD 21550
      10 Sunset Dr, Oakland, MD 21550
      10 Sunset Dr, Oakland, MD 21550
      /83

      Est $367,337 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
  • 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 $149,876

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

    414 D St, 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 $238,451 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
  • 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 $540,090

    Last Listing Agent Robert Krop Keller Williams Realty Centre

    3554 Lake Shore Dr, 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 $305,318 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
  • 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
    • 38 Traders Ln, Oakland, MD 21550
      38 Traders Ln, Oakland, MD 21550
      38 Traders Ln, Oakland, MD 21550
      /47

      Est $551,438 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
  • 483 Skippers Point Rd, Oakland, MD 21550
    483 Skippers Point Rd, Oakland, MD 21550
    483 Skippers Point Rd, Oakland, MD 21550
    /53

    $1,180,500 Sold Dec 30, 2024

    483 Skippers Point Rd, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,286 Sq Ft
    • Built 1983

    Last Sold Summary

    • $516/SF
    • 127 Days On Market

    Current Estimated Value $1,263,280

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Vacations & Sales

    483 Skippers Point Rd, 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 $2,599,162 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
  • 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
    • 1865 Paradise Point Rd, Oakland, MD 21550
      1865 Paradise Point Rd, Oakland, MD 21550
      1865 Paradise Point Rd, Oakland, MD 21550
      /76

      Est $1,065,916 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
  • 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
    • 227 W Liberty St, Oakland, MD 21550
      227 W Liberty St, Oakland, MD 21550
      227 W Liberty St, Oakland, MD 21550
      /39

      Est $217,124 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
  • 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 $562,562

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

    258 Winding Trail Ln Unit 8B, 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 $814,804 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
  • 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 $234,852

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

    114 Waterwheel Rd, Oakland, MD 21550
    • 255 Foster Rd, Oakland, MD 21550
      255 Foster Rd, Oakland, MD 21550
      255 Foster Rd, Oakland, MD 21550
      /84

      Est $326,343 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 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 $404,662

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    142 Lemley Dr Unit I, 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 $227,972 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
  • 11 Laurel Brook Dr, Oakland, MD 21550
    11 Laurel Brook Dr, Oakland, MD 21550
    11 Laurel Brook Dr, Oakland, MD 21550
    /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 $263,816

    Last Listing Agent Dan Shockey Taylor Made Deep Creek Vacations & Sales

    11 Laurel Brook Dr, Oakland, MD 21550
    • 2675 Stockslager Rd, Oakland, MD 21550
      2675 Stockslager Rd, Oakland, MD 21550
      2675 Stockslager Rd, Oakland, MD 21550
      /83

      Est $1,319,953 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
  • 5914 Maryland Hwy, Oakland, MD 21550
    5914 Maryland Hwy, Oakland, MD 21550
    5914 Maryland Hwy, Oakland, MD 21550
    /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 $159,528

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Vacations & Sales

    5914 Maryland Hwy, 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 $745,907 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

Showing Results 401 - 440, Page 11 of 18

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