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    ZIP Code: 21550
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    32 Properties Available

    32 Properties Available

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    • Square Feet (Biggest)
    308 WINDING TRAIL LN #11B, Oakland, MD 21550
    1/61
    New

    $615,000

    5 Beds5 Baths3,300 SqFt

    308 WINDING TRAIL LN #11B, Oakland, MD 21550

    MLS# MDGA2012146

    Listed by Taylor-Made Deep Creek Sales

    Bright MLS (BMLS)
    511 HILLTOP RD, Oakland, MD 21550
    1/51
    Active

    $434,900

    4 Beds3 Baths2,406 SqFt

    511 HILLTOP RD, Oakland, MD 21550

    MLS# MDGA2012082

    Listed by Taylor-Made Deep Creek Sales

    Bright MLS (BMLS)
    20160 GARRETT HWY #H706, Oakland, MD 21550
    1/27
    Active
    3D

    $309,000

    1 Bed1 Bath550 SqFt

    20160 GARRETT HWY #H706, Oakland, MD 21550

    MLS# MDGA2011894

    Listed by Taylor-Made Deep Creek Sales

    Bright MLS (BMLS)
    312 MOSS CREEK CIR, Oakland, MD 21550
    1/55
    Active

    $795,000

    5 Beds4 Baths4,230 SqFt

    312 MOSS CREEK CIR, Oakland, MD 21550

    MLS# MDGA2011736

    Listed by Taylor-Made Deep Creek Sales

    Bright MLS (BMLS)
    17921 GARRETT HWY, Oakland, MD 21550
    1/56
    Price Dropped by $34K

    $325,000

    4 Beds2 Baths1,563 SqFt

    17921 GARRETT HWY, Oakland, MD 21550

    MLS# MDGA2011818

    Listed by Taylor-Made Deep Creek Sales

    Bright MLS (BMLS)
    8 HIDDEN COVE CT, Oakland, MD 21550
    1/65
    Under Contract
    3D

    $949,000

    4 Beds3 Baths2,856 SqFt

    8 HIDDEN COVE CT, Oakland, MD 21550

    MLS# MDGA2011746

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
    638 GLENDALE RD, Oakland, MD 21550
    1/56
    Active

    $745,000

    5 Beds3 Baths2,640 SqFt

    638 GLENDALE RD, Oakland, MD 21550

    MLS# MDGA2011738

    Listed by Taylor-Made Deep Creek Sales

    Bright MLS (BMLS)
    55 VILLAGE DR #5, Oakland, MD 21550
    1/45
    Price Dropped by $10K
    3D

    $585,000

    3 Beds3 Baths2,280 SqFt

    55 VILLAGE DR #5, Oakland, MD 21550

    MLS# MDGA2011682

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
    1010 HOLY CROSS DR, Oakland, MD 21550
    1/147
    Active
    3D

    $5,150,000

    8 Beds9 Baths10,300 SqFt

    1010 HOLY CROSS DR, Oakland, MD 21550

    MLS# MDGA2011388

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
    113 JUBB MEADOWS LN, Oakland, MD 21550
    1/69
    Active
    3D

    $899,900

    4 Beds4 Baths3,185 SqFt

    113 JUBB MEADOWS LN, Oakland, MD 21550

    MLS# MDGA2011494

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
    565 GLENDALE RD #124, Oakland, MD 21550
    1/30
    Price Dropped by $15K

    $144,000

    1 Bed1 Bath382 SqFt

    565 GLENDALE RD #124, Oakland, MD 21550

    MLS# MDGA2011422

    Listed by Taylor-Made Deep Creek Sales

    Bright MLS (BMLS)
    163 MITCHELL DR, Oakland, MD 21550
    1/60
    Price Dropped by $10K
    3D

    $289,000

    3 Beds3 Baths2,242 SqFt

    163 MITCHELL DR, Oakland, MD 21550

    MLS# MDGA2011294

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
    164 GRANDVIEW DR, Oakland, MD 21550
    1/50
    Active

    $950,000

    3 Beds3 Baths2,368 SqFt

    164 GRANDVIEW DR, Oakland, MD 21550

    MLS# MDGA2011052

    Listed by Taylor-Made Deep Creek Sales

    Bright MLS (BMLS)
    157 JEFFREY LN #21B, Oakland, MD 21550
    1/29
    Price Dropped by $2K

    $297,000

    2 Beds1 Bath550 SqFt

    157 JEFFREY LN #21B, Oakland, MD 21550

    MLS# MDGA2011174

    Listed by Taylor-Made Deep Creek Sales

    Bright MLS (BMLS)
    505 SOUTHERN PINES DR, Oakland, MD 21550
    1/38
    Price Dropped by $5K

    $287,500

    3 Beds2 Baths1,248 SqFt

    505 SOUTHERN PINES DR, Oakland, MD 21550

    MLS# MDGA2011242

    Listed by Taylor-Made Deep Creek Sales

    Bright MLS (BMLS)
    52 DAM VIEW DR, Oakland, MD 21550
    1/91
    Price Dropped by $13K
    3D

    $1,074,900

    4 Beds6 Baths3,032 SqFt

    52 DAM VIEW DR, Oakland, MD 21550

    MLS# MDGA2011104

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
    815 CHADDERTON SCHOOL RD, Oakland, MD 21550
    1/110
    Under Contract
    3D

    $1,900,000

    5 Beds4 Baths4,619 SqFt

    815 CHADDERTON SCHOOL RD, Oakland, MD 21550

    MLS# MDGA2011092

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
    130 TIMBERLOFT CIR #14, Oakland, MD 21550
    1/79
    Active
    3D

    $749,000

    3 Beds3 Baths1,900 SqFt

    130 TIMBERLOFT CIR #14, Oakland, MD 21550

    MLS# MDGA2011146

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
    130 MYSTIC CREEK TRL #1B, Oakland, MD 21550
    1/69
    Pending
    3D

    $639,000

    5 Beds5 Baths2,200 SqFt

    130 MYSTIC CREEK TRL #1B, Oakland, MD 21550

    MLS# MDGA2011072

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
    20160 GARRETT HWY #F501-701, Oakland, MD 21550
    1/68
    Active
    3D

    $575,000

    3 Beds2 Baths1,700 SqFt

    20160 GARRETT HWY #F501-701, Oakland, MD 21550

    MLS# MDGA2010702

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
    47 HOLY CROSS, Oakland, MD 21550
    1/109
    Active
    3D

    $6,499,900

    8 Beds9 Baths11,417 SqFt

    47 HOLY CROSS, Oakland, MD 21550

    MLS# MDGA2010560

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
    5024 CRANESVILLE RD, Oakland, MD 21550
    1/67
    Under Contract
    3D

    $399,000

    3 Beds3 Baths2,128 SqFt

    5024 CRANESVILLE RD, Oakland, MD 21550

    MLS# MDGA2010510

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
    333 SLOAN TRACT RD, Oakland, MD 21550
    1/43
    Active

    $475,000

    4 Beds4 Baths1,492 SqFt

    333 SLOAN TRACT RD, Oakland, MD 21550

    MLS# MDGA2009836

    Listed by Taylor-Made Deep Creek Sales

    Bright MLS (BMLS)
    328 STOOL ROCK RD, Oakland, MD 21550
    1/134
    Active
    3D

    $545,000

    4 Beds3 Baths1,860 SqFt

    328 STOOL ROCK RD, Oakland, MD 21550

    MLS# MDGA2009150

    Listed by Railey Realty, Inc.

    Bright MLS (BMLS)
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    Aspen Johnson

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      • Home
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        1. Rental Listings
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        1. All Listings
        2. Featured Listings
        About Aspen
        1. About Me
      • Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Market Snapshot
    Homes With Aspen LLC
    Aspen Johnson

    +1(804) 735-6627 homeswithaspenllc@gmail.com

    Get My App

    Powered by Lofty Inc. Copyright 2026. 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.