10,771

Oakland, MD Homes

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  • /139

    $2,625,000

    Sold Mar 31, 2026

    56 Bee Tree Ln, Oakland, MD 21550

    • 6 Beds
    • 7.5 Baths
    • 5,100 Sq Ft
    • Built 2000

    Last Sold Summary

    • $515/SF
    • 305 Days On Market

    Current Estimated Value $2,641,772

    Last Listing Agent Susan Bell Railey Realty, Inc.

    56 Bee Tree Ln, Oakland, MD 21550
    • /29

      Est $173,584

      Not Listed For Sale

      216 E Center St, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,472 Sq Ft
      • Built 1932
      216 E Center St, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • /7

    $36,000

    $10K PRICE INCREASE Pending
    • Land
    • 2 Acres
    • $18,000 per Acre

    0 Hutton Road(2 Acres), Oakland, MD 21550

    2 acres off Hutton Rd, raw land, endless possibilities. No restrictions, county zoning applies. Manly tree covered.

    Julie Mead The KW Collective

    0 Hutton Road(2 Acres), Oakland, MD 21550
  • /15

    $75,000

    Sold Apr 10, 2026

    60 Gorman St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,488 Sq Ft
    • Built 1920

    Last Sold Summary

    • $50/SF
    • 126 Days On Market

    Current Estimated Value $75,525

    Last Listing Agent Jennifer Jackson Charis Realty Group

    60 Gorman St, Oakland, MD 21550
    • /33

      Est $416,570

      Not Listed For Sale

      1012 Hemlock Cir, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,590 Sq Ft
      • Built 2002
      1012 Hemlock Cir, Oakland, MD 21550

      Last Sold Summary

      • 35 Days On Market

  • /5

    $18,000

    • Land
    • 27,007 Sq Ft
    • $29,032 per Acre

    13 Birchwood Dr, Oakland, MD 21550

    Discover your own mountain escape in the gated community of Youghiogheny Mountain Resort! This 0.62-acre lot is perfect for building a dream home or weekend retreat, surrounded by miles of ATV trails, hunting, and fishing. Ideally located near Wisp Resort, Deep Creek Lake, Herrington Manor State Park, and Swallow Falls State Park, you’ll enjoy year-round outdoor adventure. Approved for a sand

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    13 Birchwood Dr, Oakland, MD 21550
  • /35

    $235,000

    Sold Oct 08, 2025

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 660 Sq Ft
    • Built 1990

    Last Sold Summary

    • $356/SF
    • 11 Days On Market

    Current Estimated Value $240,781

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

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    • /7

      Est $300,927

      Not Listed For Sale

      1517 Upperman Rd, Oakland, MD 21550

      • 1 Bed
      • 1 Bath
      • 530 Sq Ft
      • Built 2024
      1517 Upperman Rd, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

  • /69

    $2,100,000

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

    1038 S Blakeslee Rd, Oakland, MD 21550

    Welcome to 1038 S Blakeslee Road! A spacious lakefront retreat on Deep Creek Lake offering effortless lakeside living. A Rare opportunity to own in one of Deep Creek’s most sought-after lakeside communities. This five-bedroom, five-bath home sits on a large 1.11-acre level lot with easy access to the water and generous outdoor space for recreation and entertaining. Inside, the home is warm and

    Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    1038 S Blakeslee Rd, Oakland, MD 21550
  • /93

    $785,000

    Sold Jun 01, 2026

    1001 Sutter Ln, Oakland, MD 21550

    • 5 Beds
    • 6 Baths
    • 6,550 Sq Ft
    • Built 2000

    Last Sold Summary

    • $120/SF
    • 172 Days On Market

    Current Estimated Value $787,171

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1001 Sutter Ln, Oakland, MD 21550
    • /52

      Est $230,555

      Not Listed For Sale

      1865 Garrett Rd, Oakland, MD 21550

      • 4 Beds
      • 1 Bath
      • 1,144 Sq Ft
      • Built 1994
      1865 Garrett Rd, Oakland, MD 21550

      Last Sold Summary

      • 19 Days On Market

  • /24

    $18,000

    • Land
    • 20,473 Sq Ft
    • $38,298 per Acre

    27 Gobbler Run Rd, Oakland, MD 21550

    Build your ideal mountain retreat in the gated community of Youghiogheny Mountain Resort! This level 0.47-acre lot offers an easy build site and is Health Department approved for a shallow trench gravity septic system. Enjoy access to ATV trails, hunting, and fishing, all just minutes from Wisp Resort, Deep Creek Lake, and Swallow Falls State Park. Whether you're planning a full-time home or

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    27 Gobbler Run Rd, Oakland, MD 21550
  • /17

    $18,000

    Sold Nov 14, 2025

    Lots 59 & 60 Cedar Ln, Oakland, MD 21550

    • Land
    • 42,688 Sq Ft
    • $18,367 per Acre

    Last Sold Summary

    • 17 Days On Market

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

    Lots 59 & 60 Cedar Ln, Oakland, MD 21550
    • /21

      Est $273,565

      Not Listed For Sale

      17 Laurel Brook Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,840 Sq Ft
      • Built 1991
      17 Laurel Brook Dr, Oakland, MD 21550

      Last Sold Summary

      • 171 Days On Market

  • /17

    $35,000

    • Land
    • 1.92 Acres
    • $18,229 per Acre

    233 Rhododendron Dr, Oakland, MD 21550

    Fantastic opportunity in the gated community of Youghiogheny Mountain Resort. This 1.92-acre lot is perfect for outdoor enthusiasts, offering ATV riding, hunting, fishing, and more. Build your dream home or a recreational retreat. Approved for a 2-bedroom conventional system, with the option to expand using a sand mound system. Located just minutes from Wisp Resort, Deep Creek Lake, Herrington

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    233 Rhododendron Dr, Oakland, MD 21550
  • /34

    $459,000

    Sold Nov 25, 2025

    50 Village Dr Unit 7, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 2006

    Last Sold Summary

    • $455/SF
    • 17 Days On Market

    Current Estimated Value $430,829

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    50 Village Dr Unit 7, Oakland, MD 21550
    • /70

      Est $1,661,983

      Not Listed For Sale

      22 Duck Cove Rd, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 1,964 Sq Ft
      • Built 1960
      22 Duck Cove Rd, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /32

    $114,000

    $6K PRICE DROP Under Contract
    • 2 Beds
    • 1 Bath
    • 1,029 Sq Ft

    5151 Hutton Rd, Oakland, MD 21550

    REDUCED - Nearly an acre convenient to town - Some upgrades; newer metal roof, electrical panel box, furnace and other areas - Rear carport/patio area has easy at level access to main level - Large front porch with low maintenance entry area with wash/dryer hook-up - Good one level living layout - Sold as-is - No utilities currently active - No repairs before purchase or a lending requirement

    Mark Van Tyne Julian Agency Real Estate

    5151 Hutton Rd, Oakland, MD 21550
  • /50

    $559,250

    Sold Sep 02, 2025

    285 Winding Trail Ln Unit 10A, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2008

    Last Sold Summary

    • $169/SF
    • 62 Days On Market

    Current Estimated Value $561,066

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    • /41

      Est $337,865

      Not Listed For Sale

      139 Hunters Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,240 Sq Ft
      • Built 1991
      139 Hunters Dr, Oakland, MD 21550

      Last Sold Summary

      • 45 Days On Market

  • /5

    $89,900

    • Land
    • 15.75 Acres
    • $5,708 per Acre

    TBD 15 75 Acres Bethlehem Rd, Oakland, MD 21550

    Tucked away just minutes from town, this 15.75± acre wooded parcel offers a quiet country setting with the privacy many buyers are searching for. Located off Bethlehem Road near the Potomac State Forest, the property features largely level terrain, mature trees, and abundant wildlife—an ideal backdrop for a private residence, weekend retreat, or recreational use. The surrounding area provides

    Thomas Long Railey Realty, Inc.

    TBD 15 75 Acres Bethlehem Rd, Oakland, MD 21550
  • /13

    $155,000

    Sold Jan 08, 2026

    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550

    • Land
    • 31,363 Sq Ft
    • $215,278 per Acre

    Last Sold Summary

    • 16 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550
    • /49

      Est $908,258

      Not Listed For Sale

      158 Silver Tree Ln, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 2,250 Sq Ft
      • Built 2003
      158 Silver Tree Ln, Oakland, MD 21550

      Last Sold Summary

      • 79 Days On Market

  • /34

    $399,900

    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    565 Glendale Rd Unit 303B, Oakland, MD 21550

    Experience lakefront living at its finest in the premier unit at Silver Tree Suites! This beautifully updated 2-bedroom, 1-bath condo showcases rustic charm with custom woodworking throughout. Featuring two separate living areas, there's plenty of space to relax and entertain. Enjoy year-round lake views from the private balcony, unwind by either of the two fireplaces, and appreciate the added

    Sean Sober Taylor-Made Deep Creek Real Estate, LLC

    565 Glendale Rd Unit 303B, Oakland, MD 21550
  • /54

    $550,000

    Sold Aug 29, 2025

    710 Hunters Ridge Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft
    • Built 2007

    Last Sold Summary

    • $317/SF
    • 70 Days On Market

    Current Estimated Value $540,866

    Last Listing Agent Andrew Orr The KW Collective

    710 Hunters Ridge Dr, Oakland, MD 21550
    • /83

      Est $2,284,410

      Not Listed For Sale

      320 Lake Forest Dr, Oakland, MD 21550

      • 6 Beds
      • 4.5 Baths
      • 2,363 Sq Ft
      • Built 1997
      320 Lake Forest Dr, Oakland, MD 21550

      Last Sold Summary

      • 111 Days On Market

  • /89

    $2,100,000

    Under Contract
    • 6 Beds
    • 4.5 Baths
    • 3,882 Sq Ft

    209 Glendale Rd, Oakland, MD 21550

    If you're in the market for location, convenience, and rental income, this inviting 6 Bedroom 4.5 bath Lakefront home is calling for you! Located in the heart of the action on Deep Creek Lake, the 3 level chateau has been updated and upgraded both inside and out. Restaurants, the movie theatre, shopping and Deep Creek Lake State Park are all within walking distance. Offering an open layout with

    Bill Weissgerber Railey Realty, Inc.

    209 Glendale Rd, Oakland, MD 21550
  • /20

    $200,000

    Sold Feb 06, 2026

    123 Mountainview Ct, Oakland, MD 21550

    • Land
    • 1.69 Acres
    • $118,343 per Acre

    Last Sold Summary

    • 72 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    123 Mountainview Ct, Oakland, MD 21550
    • /95

      Est $545,488

      Not Listed For Sale

      204 Farm View Ln, Oakland, MD 21550

      • 3 Beds
      • 4 Baths
      • 2,268 Sq Ft
      • Built 2007
      204 Farm View Ln, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /32

    $249,900

    • 2 Beds
    • 1 Bath
    • 772 Sq Ft

    565 Glendale Rd Unit 306, Oakland, MD 21550

    Experience the best of Deep Creek Lake living from this beautifully appointed studio loft at Silver Tree Suites—one of the lake’s most sought-after locations! Offering two separate sleeping areas, a kitchenette, gas fireplace, and private balcony, this unit is designed for comfort and easy getaway living. Tastefully updated with new carpet and flooring, as well as kitchen and bathroom

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 306, Oakland, MD 21550
  • /51

    $660,000

    Sold Jan 30, 2026

    155 Basswood Way, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,792 Sq Ft
    • Built 2003

    Last Sold Summary

    • $236/SF
    • 268 Days On Market

    Current Estimated Value $640,242

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    155 Basswood Way, Oakland, MD 21550
    • /132

      Est $3,441,621

      Not Listed For Sale

      2524 Stockslager Rd, Oakland, MD 21550

      • 5 Beds
      • 7 Baths
      • 9,134 Sq Ft
      • Built 2006
      2524 Stockslager Rd, Oakland, MD 21550

      Last Sold Summary

      • 15 Days On Market

  • /43

    $220,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    1256 Boiling Spring Rd, Oakland, MD 21550

    Spacious home nestled in a beautifully wooded area in Deer Park! This 3 bedroom, 2 bath home has a primary suite, main floor laundry, and tons of storage space in the basement. The fenced in backyard allows for privacy and enjoying the outdoors. Let your imagination go wild with all the unfinished space in the basement that you can transform into additional living space. Brand new mini-split

    Angie House Railey Realty, Inc.

    1256 Boiling Spring Rd, Oakland, MD 21550
  • /37

    $250,000

    Sold Dec 31, 2025

    511 E Green St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft
    • Built 1924

    Last Sold Summary

    • $133/SF
    • 176 Days On Market

    Current Estimated Value $247,685

    Last Listing Agent Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    511 E Green St, Oakland, MD 21550
    • /42

      Est $474,592

      Not Listed For Sale

      426 Pergin Farm Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,596 Sq Ft
      • Built 1985
      426 Pergin Farm Rd, Oakland, MD 21550

      Last Sold Summary

      • 15 Days On Market

  • /64

    $415,000

    • 4 Beds
    • 2 Baths
    • 2,234 Sq Ft

    1499 Foster Rd, Oakland, MD 21550

    Welcome to Ricky's Retreat, a beautifully renovated mountain retreat nestled on 1.17 private wooded acres in the heart of Garrett County. Ideally located just minutes from Deep Creek Lake, Wisp Resort, Swallow Falls State Park, and downtown Oakland, this turnkey property offers the perfect balance of privacy, recreation, and modern comfort. Originally built as a raised ranch, the home has

    Kelsey Meyers Railey Realty, Inc.

    1499 Foster Rd, Oakland, MD 21550
  • /98

    $590,000

    Sold Oct 10, 2025

    2719 Broadford Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 4,253 Sq Ft
    • Built 1984

    Last Sold Summary

    • $139/SF
    • 168 Days On Market

    Current Estimated Value $575,993

    Last Listing Agent Rich Orr Railey Realty, Inc.

    2719 Broadford Rd, Oakland, MD 21550
    • /81

      Est $651,704

      Not Listed For Sale

      43 Robinwood Dr, Oakland, MD 21550

      • 3 Beds
      • 3.5 Baths
      • 2,921 Sq Ft
      • Built 2005
      43 Robinwood Dr, Oakland, MD 21550

      Last Sold Summary

      • 148 Days On Market

  • /62

    $735,000

    Under Contract
    • 5 Beds
    • 5 Baths
    • 3,664 Sq Ft

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    Check out this beautifully built and maintained 5 bedroom 5 bathroom lake area chalet style home. Located on the Southern side of the lake, near the headwaters of Deep Creek. The namesake stream that feeds into the nearby lake. This property offers it's new owners a tremendous amount of room for storage and entertaining and three levels of finished living space. The top floor is designed as an

    Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • /47

    $405,000

    Sold Aug 08, 2025

    343 Maple Del Ln, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,404 Sq Ft
    • Built 1993

    Last Sold Summary

    • $288/SF
    • 3 Days On Market

    Current Estimated Value $397,724

    Last Listing Agent Julie Mead The KW Collective

    343 Maple Del Ln, Oakland, MD 21550

Showing Results 281 - 320, Page 8 of 18

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