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218 Properties

218 Properties Available

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  • 20676 GARRETT HWY, Oakland, MD 21550
    1/25 25
    Open Sun 4PM-7PM

    $1,499,950

    5 Beds5 Baths2,280 SqFt

    20676 GARRETT HWY, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009852

    Listed by HomeZu by Simple Choice

    Bright MLS (BMLS)

    READ MORE

  • 321 DEER PARK HOTEL RD, Oakland, MD 21550
    1/104 104
    Open Sat 11AM-1PM

    $386,500

    3 Beds2 Baths2,516 SqFt

    321 DEER PARK HOTEL RD, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009244

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)

    READ MORE

  • 25 SILVER TREE LN, Oakland, MD 21550
    3D
    Open Sat 12PM-3PM

    $775,000

    5 Beds4 Baths2,364 SqFt

    25 SILVER TREE LN, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009038

    Listed by Taylor Made Deep Creek Vacations & Sales

    Bright MLS (BMLS)

    READ MORE

  • 20698 GARRETT HWY, Oakland, MD 21550
    1/49 49
    Open 7/2 12PM-3PM

    $1,299,000

    4 Beds3 Baths1,844 SqFt

    20698 GARRETT HWY, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2008636

    Listed by Taylor Made Deep Creek Vacations & Sales

    Bright MLS (BMLS)

    READ MORE

  • 19956 GARRETT HWY #6, Oakland, MD 21550
    3D
    New

    $1,349,000

    4 Beds4 Baths3,000 SqFt

    19956 GARRETT HWY #6, Oakland, MD 21550

    Condo

    MLS# MDGA2009898

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)

    READ MORE

  • 113 PARADISE LN, Oakland, MD 21550
    1/57 57
    New

    $1,389,000

    5 Beds3 Baths2,056 SqFt

    113 PARADISE LN, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009890

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)

    READ MORE

  • 939 GLENDALE RD #2, Oakland, MD 21550
    1/61 61
    New

    $849,900

    3 Beds3 Baths

    939 GLENDALE RD #2, Oakland, MD 21550

    Condo

    MLS# MDGA2009876

    Listed by Taylor Made Deep Creek Vacations & Sales

    Bright MLS (BMLS)

    READ MORE

  • 1006 LAKE SHORE DR, Oakland, MD 21550
    1/61 61
    New

    $689,000

    4 Beds3 Baths1,935 SqFt

    1006 LAKE SHORE DR, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009868

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)

    READ MORE

  • 170 TANNERY RD, Oakland, MD 21550
    1/35 35
    New

    $219,000

    3 Beds2 Baths1,850 SqFt

    170 TANNERY RD, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009844

    Listed by Homecoin.com

    Bright MLS (BMLS)

    READ MORE

  • 1001 SUTTER LN, Oakland, MD 21550
    1/81 81
    New

    $899,900

    5 Beds6 Baths6,588 SqFt

    1001 SUTTER LN, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009800

    Listed by Northrop Realty

    Bright MLS (BMLS)

    READ MORE

  • 20160 GARRETT HWY #H708, Oakland, MD 21550
    3D
    New

    $300,000

    1 Bed1 Bath550 SqFt

    20160 GARRETT HWY #H708, Oakland, MD 21550

    Condo

    MLS# MDGA2009826

    Listed by The KW Collective

    Bright MLS (BMLS)

    READ MORE

  • 1484 PARADISE POINT RD, Oakland, MD 21550
    1/47 47
    New

    $1,799,900

    5 Beds5 Baths3,360 SqFt

    1484 PARADISE POINT RD, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009848

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)

    READ MORE

  • 793 MOUNTAINVIEW DR, Oakland, MD 21550
    1/42 42
    New

    $576,000

    3 Beds3 Baths1,564 SqFt

    793 MOUNTAINVIEW DR, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009762

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)

    READ MORE

  • 511 E GREEN ST, Oakland, MD 21550
    1/37 37
    New

    $309,000

    4 Beds2 Baths1,880 SqFt

    511 E GREEN ST, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009822

    Listed by Taylor Made Deep Creek Vacations & Sales

    Bright MLS (BMLS)

    READ MORE

  • 237 GLENDALE RD, Oakland, MD 21550
    1/100 100
    New

    $2,159,000

    7 Beds7 Baths3,735 SqFt

    237 GLENDALE RD, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009792

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)

    READ MORE

  • 1100 S BLAKESLEE RD, Oakland, MD 21550
    1/127 127
    Pending

    $2,775,000

    5 Beds6 Baths6,572 SqFt

    1100 S BLAKESLEE RD, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009688

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)

    READ MORE

  • 333 SLOAN TRACT RD, Oakland, MD 21550
    1/40 40
    New

    $475,000

    4 Beds4 Baths1,492 SqFt

    333 SLOAN TRACT RD, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009836

    Listed by Taylor Made Deep Creek Vacations & Sales

    Bright MLS (BMLS)

    READ MORE

  • 1681 SHADY DELL RD, Oakland, MD 21550
    1/31 31
    Under Contract

    $189,000

    3 Beds1 Bath960 SqFt

    1681 SHADY DELL RD, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009834

    Listed by Taylor Made Deep Creek Vacations & Sales

    Bright MLS (BMLS)

    READ MORE

  • 408 SHENANDOAH, Loch Lynn Heights, MD 21550
    1/43 43
    Under Contract

    $105,000

    2 Beds1 Bath960 SqFt

    408 SHENANDOAH, Loch Lynn Heights, MD 21550

    Single Family Home

    MLS# MDGA2009810

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)

    READ MORE

  • 609 SOUTHERN PINES DR, Oakland, MD 21550
    1/57 57
    Active

    $460,000

    4 Beds3 Baths2,030 SqFt

    609 SOUTHERN PINES DR, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009816

    Listed by BHHS Touchdown Home Pros Realty

    Bright MLS (BMLS)

    READ MORE

  • 285 WINDING TRAIL LN #10A, Oakland, MD 21550
    1/50 50
    Active

    $589,000

    5 Beds5 Baths3,300 SqFt

    285 WINDING TRAIL LN #10A, Oakland, MD 21550

    Condo

    MLS# MDGA2009744

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)

    READ MORE

  • 320 COOLIDGE AVE, Oakland, MD 21550
    1/28 28
    Active

    $139,000

    2 Beds1 Bath720 SqFt

    320 COOLIDGE AVE, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009796

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)

    READ MORE

  • 62 MIDDLETON RD, Oakland, MD 21550
    1/67 67
    Active

    $849,900

    3 Beds3 Baths2,397 SqFt

    62 MIDDLETON RD, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009756

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)

    READ MORE

  • 5914 MARYLAND HWY, Oakland, MD 21550
    1/38 38
    Under Contract

    $139,000

    4 Beds2 Baths1,775 SqFt

    5914 MARYLAND HWY, Oakland, MD 21550

    Single Family Home

    MLS# MDGA2009752

    Listed by Taylor Made Deep Creek Vacations & Sales

    Bright MLS (BMLS)

    READ MORE

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Skip Tolley License ID: 528296

+1(410) 935-7500 skip@captainwaterfront.com

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WFI_Logo_Wideexp and realty insider logo_larger 2
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Skip Tolley License ID: 528296

+1(410) 935-7500 skip@captainwaterfront.com

    • Home
      Market Snapshot
    • Buy
      Contact
    • Sell
      1. Sell
      2. Recently Sold

Get My App

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.