10,714

Oakland, MD Homes

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  • 3 Edens Ridge Rd, Oakland, MD 21550
    3 Edens Ridge Rd, Oakland, MD 21550
    3 Edens Ridge Rd, Oakland, MD 21550
    /6

    $57,500 Sold Aug 27, 2025

    3 Edens Ridge Rd, Oakland, MD 21550

    • Land
    • 5 Acres
    • $11,500 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    3 Edens Ridge Rd, Oakland, MD 21550
    • 644 Silver Knob Rd, Oakland, MD 21550
      644 Silver Knob Rd, Oakland, MD 21550
      644 Silver Knob Rd, Oakland, MD 21550
      /38

      Est $321,009 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,728 Sq Ft

      644 Silver Knob Rd, Oakland, MD 21550

      644 Silver Knob Rd, Oakland, MD 21550
  • 181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    /25

    $269,900

    • 2 Beds
    • 1 Bath
    • 670 Sq Ft

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550

    Discover comfort and convenience in this charming 2-bedroom, 1-bath unit ideally located in the desirable Roman Ridge at Traders Landing community. Enjoy peaceful lake views from your covered front deck—the perfect spot to relax with your morning coffee or unwind in the evening. Inside, you’ll find a warm and inviting living space featuring a wood-burning fireplace to take the chill off during

    Larry Smith Railey Realty, Inc.

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
  • 215 Lower Penn Point Dr, Oakland, MD 21550
    215 Lower Penn Point Dr, Oakland, MD 21550
    215 Lower Penn Point Dr, Oakland, MD 21550
    /49

    $1,250,000 Sold Apr 11, 2025

    215 Lower Penn Point Dr, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,580 Sq Ft
    • Built 2001

    Last Sold Summary

    • $484/SF
    • 51 Days On Market

    Current Estimated Value $1,232,265

    Last Listing Agent Lauren McCann Railey Realty, Inc.

    215 Lower Penn Point Dr, Oakland, MD 21550
    • 840 Smouse Rd, Oakland, MD 21550
      840 Smouse Rd, Oakland, MD 21550
      840 Smouse Rd, Oakland, MD 21550
      /57

      Est $345,743 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,863 Sq Ft

      840 Smouse Rd, Oakland, MD 21550

      840 Smouse Rd, Oakland, MD 21550
  • 609 Southern Pines Dr, Oakland, MD 21550
    609 Southern Pines Dr, Oakland, MD 21550
    609 Southern Pines Dr, Oakland, MD 21550
    /59

    $440,000

    • 4 Beds
    • 2.5 Baths
    • 2,030 Sq Ft

    609 Southern Pines Dr, Oakland, MD 21550

    Welcome to your next dream home! Nestled on a 4-acre wooded lot, this custom built traditional-style residence combines comfort, and convenience. Just minutes from Broadford Lake Park, healthcare, shopping, Deep Creek Lake, and Wisp Ski Resort, this peaceful property offers easy access to all the local amenities. Two story stone & cedar, 4BR, 2.5 Bath w/ 2 - car attached garage, & 2 - car

    Brian Covell BHHS Touchdown Home Pros Realty

    609 Southern Pines Dr, Oakland, MD 21550
  • 36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    36 Jeffrey Ln Unit 6B, 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

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

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    • 968 Paradise Heights, Oakland, MD 21550
      968 Paradise Heights, Oakland, MD 21550
      968 Paradise Heights, Oakland, MD 21550
      /30

      Est $383,418 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,080 Sq Ft

      968 Paradise Heights, Oakland, MD 21550

      968 Paradise Heights, Oakland, MD 21550
  • 13209 Garrett Hwy, Oakland, MD 21550
    13209 Garrett Hwy, Oakland, MD 21550
    13209 Garrett Hwy, Oakland, MD 21550
    /10

    $649,000 Under Contract

    • Land
    • 37.8 Acres
    • $17,169 per Acre

    13209 Garrett Hwy, Oakland, MD 21550

    Access to Public Utilities and Natural Gas within the Town of Oakland Utility systems.Access to Public Utilities and Natural Gas within the Town of Oakland Utility systems. Property has State Highway Entrance completed. New Owner would utilize this access Road to develop property. Recorded plat and Covenants available online.

    Rich Orr Railey Realty, Inc.

    13209 Garrett Hwy, Oakland, MD 21550
  • 20160 Garrett Hwy Unit F503, Oakland, MD 21550
    20160 Garrett Hwy Unit F503, Oakland, MD 21550
    20160 Garrett Hwy Unit F503, Oakland, MD 21550
    /68

    $540,000 Sold Mar 31, 2025

    20160 Garrett Hwy Unit F503, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Built 1972

    Last Sold Summary

    • $318/SF
    • 0 Days On Market

    Current Estimated Value $536,601

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

    20160 Garrett Hwy Unit F503, Oakland, MD 21550
    • 1265 Bray School Rd, Oakland, MD 21550
      1265 Bray School Rd, Oakland, MD 21550
      1265 Bray School Rd, Oakland, MD 21550
      /105

      Est $425,335 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,920 Sq Ft

      1265 Bray School Rd, Oakland, MD 21550

      1265 Bray School Rd, Oakland, MD 21550
  • 198 Grandview Dr, Oakland, MD 21550
    198 Grandview Dr, Oakland, MD 21550
    198 Grandview Dr, Oakland, MD 21550
    /45

    $775,000 Under Contract

    • 3 Beds
    • 3 Baths
    • 2,744 Sq Ft

    198 Grandview Dr, Oakland, MD 21550

    Lake views for days and room to relax in every direction!Welcome to 198 Grandview Drive, a 3-bedroom, 3-bath log home perfectly perched to capture sweeping views of Deep Creek Lake and the surrounding mountains. With three finished levels of living space, this home blends rustic charm with modern comfort. Hardwood floors span the main and upper levels, while the finished lower level features

    Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, MD 21550
  • Lots 59 & 60 Cedar Ln, Oakland, MD 21550
    Lots 59 & 60 Cedar Ln, Oakland, MD 21550
    Lots 59 & 60 Cedar Ln, Oakland, MD 21550
    /17

    $18,000 Sold Nov 14, 2025

    Lots 59 & 60 Cedar Ln, Oakland, MD 21550

    • Land
    • 0.98 Acre
    • $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
    • 325 Coolidge Ave, Oakland, MD 21550
      325 Coolidge Ave, Oakland, MD 21550
      325 Coolidge Ave, Oakland, MD 21550
      /29

      Est $168,367 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 834 Sq Ft

      325 Coolidge Ave, Oakland, MD 21550

      325 Coolidge Ave, Oakland, MD 21550
  • 0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
    /5

    $30,000

    • Land
    • 0.34 Acre
    • $88,235 per Acre

    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550

    Love Deep Creek Lake living. This 0.34 acre wooded lot sits near the heart of everything that makes the lake special. Launch the boat at nearby marinas, hike and swim at Deep Creek Lake State Park, and enjoy four season adventure at Wisp Resort with skiing, tubing, and mountain rides. Restaurants, shops, and local events are just down the road, while your homesite feels peaceful and private. Do

    Debra Hayne Cummings & Co. Realtors

    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
  • 50 Village Dr Unit 7, Oakland, MD 21550
    50 Village Dr Unit 7, Oakland, MD 21550
    50 Village Dr Unit 7, 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

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    50 Village Dr Unit 7, Oakland, MD 21550
    • 11 Trailside Ct, Oakland, MD 21550
      11 Trailside Ct, Oakland, MD 21550
      11 Trailside Ct, Oakland, MD 21550
      /56

      Est $570,289 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,442 Sq Ft

      11 Trailside Ct, Oakland, MD 21550

      11 Trailside Ct, Oakland, MD 21550
  • Lot 14 Warnick Way, Oakland, MD 21550
    Lot 14 Warnick Way, Oakland, MD 21550
    Lot 14 Warnick Way, Oakland, MD 21550
    /3

    $45,900

    • Land
    • 1.02 Acres
    • $45,000 per Acre

    Lot 14 Warnick Way, Oakland, MD 21550

    Enjoy mountain views from this 1.02-acre, mostly wooded lot! No mobile homes permitted. No HOA. Easy access off Spring Glade Rd. Ideally situated between Oakland and Deep Creek Lake. Contact me today for more info!

    Nicole Jackson Railey Realty, Inc.

    Lot 14 Warnick Way, Oakland, MD 21550
  • 285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    285 Winding Trail Ln Unit 10A, 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 $561,751

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    • 478 Lake Forest Dr, Oakland, MD 21550
      478 Lake Forest Dr, Oakland, MD 21550
      478 Lake Forest Dr, Oakland, MD 21550
      /95

      Est $1,591,142 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 2,688 Sq Ft

      478 Lake Forest Dr, Oakland, MD 21550

      478 Lake Forest Dr, Oakland, MD 21550
  • 34 Laurel Brook Dr, Oakland, MD 21550
    34 Laurel Brook Dr, Oakland, MD 21550
    34 Laurel Brook Dr, Oakland, MD 21550
    /34

    $299,500 Under Contract

    • 3 Beds
    • 3 Baths

    34 Laurel Brook Dr, Oakland, MD 21550

    Welcome to 34 Laurel Brook Drive! An impeccably remodeled townhome just moments from Deep Creek Lake and Oakland, Maryland. Renovated in 2019 and among the larger homes in the neighborhood, this property features 3 bedrooms, 3 full bathrooms, and over 2,000 sq ft of finished space. Highlights include stylish flooring, a modern kitchen, and recent upgrades such as new skylights and primary bedroom

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    34 Laurel Brook Dr, Oakland, MD 21550
  • 710 Hunters Ridge Dr, Oakland, MD 21550
    710 Hunters Ridge Dr, Oakland, MD 21550
    710 Hunters Ridge Dr, 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 $547,019

    Last Listing Agent Andrew Orr The KW Collective

    710 Hunters Ridge Dr, Oakland, MD 21550
    • 29 Crescent Ln, Oakland, MD 21550
      29 Crescent Ln, Oakland, MD 21550
      29 Crescent Ln, Oakland, MD 21550
      /38

      Est $445,270 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,536 Sq Ft

      29 Crescent Ln, Oakland, MD 21550

      29 Crescent Ln, Oakland, MD 21550
  • 961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    /50

    $379,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    961 Cedar Ln, Oakland, MD 21550

    Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat offers privacy, comfort, and plenty of space to unwind. Step inside to find a warm and inviting main level highlighted by a stone fireplace, cozy dining area, and galley-style kitchen. Relax on the screened-in porch complete with a hot tub under roof, perfect for year-round enjoyment. The finished basement

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    961 Cedar Ln, Oakland, MD 21550
  • 655 Bray School Rd, Oakland, MD 21550
    655 Bray School Rd, Oakland, MD 21550
    655 Bray School Rd, Oakland, MD 21550
    /67

    $259,000 Sold May 14, 2025

    655 Bray School Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1984

    Last Sold Summary

    • $270/SF
    • 4 Days On Market

    Current Estimated Value $263,805

    Last Listing Agent Susan Bell Railey Realty, Inc.

    655 Bray School Rd, Oakland, MD 21550
    • 148 Wanderer Ln, Oakland, MD 21550
      148 Wanderer Ln, Oakland, MD 21550
      148 Wanderer Ln, Oakland, MD 21550
      /56

      Est $686,367 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,355 Sq Ft

      148 Wanderer Ln, Oakland, MD 21550

      148 Wanderer Ln, Oakland, MD 21550
  • LOT 181 Santa fe Trail, Oakland, MD 21550
    LOT 181 Santa fe Trail, Oakland, MD 21550
    LOT 181 Santa fe Trail, Oakland, MD 21550
    /12

    $45,000

    • Land
    • 0.34 Acre
    • $132,353 per Acre

    LOT 181 Santa fe Trail, Oakland, MD 21550

    Don't miss the opportunity to own a lake area lot near the one and only Deep Creek Lake. 0.34 acre wooded lot, close to multiple local attractions. Call today! Verify utilities with Garrett County Environmental Department. Being sold subject to successful perc.

    Amy Skipper Railey Realty, Inc.

    LOT 181 Santa fe Trail, Oakland, MD 21550
  • 1517 Upperman Rd, Oakland, MD 21550
    1517 Upperman Rd, Oakland, MD 21550
    1517 Upperman Rd, Oakland, MD 21550
    /7

    $389,000 Sold Jan 24, 2025

    1517 Upperman Rd, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 530 Sq Ft
    • Built 2024

    Last Sold Summary

    • $734/SF
    • 0 Days On Market

    Current Estimated Value $396,505

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1517 Upperman Rd, Oakland, MD 21550
    • 1597 Lake Shore Dr, Oakland, MD 21550
      1597 Lake Shore Dr, Oakland, MD 21550
      1597 Lake Shore Dr, Oakland, MD 21550
      /82

      Est $1,712,790 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 1,904 Sq Ft

      1597 Lake Shore Dr, Oakland, MD 21550

      1597 Lake Shore Dr, Oakland, MD 21550
  • 0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
    /4

    $29,900

    • Land
    • 1.09 Acres
    • $27,431 per Acre

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550

    1+ acre building lot. Fairly leveled cleared lot with some distant mountain views. Paved County road frontage with private road/drive access to lot. Approved for private septic and well. Electric on-site. Located approx. 10+ mins from Deep Creek Lake and approx. less than 5 minutes from Oakland. Located within small 8 lot development, "The Homestead".

    Chip Smith 1 Real Estate Source LLC

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
  • 0 Oakland Sang Run Rd Unit MDGA2008132, Oakland, MD 21550
    0 Oakland Sang Run Rd Unit MDGA2008132, Oakland, MD 21550
    0 Oakland Sang Run Rd Unit MDGA2008132, Oakland, MD 21550
    /13

    $34,500 Sold Feb 12, 2025

    0 Oakland Sang Run Rd Unit MDGA2008132, Oakland, MD 21550

    • Land
    • 3.18 Acres
    • $10,849 per Acre

    Last Sold Summary

    • 114 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    0 Oakland Sang Run Rd Unit MDGA2008132, Oakland, MD 21550
    • 216 E Center St, Oakland, MD 21550
      216 E Center St, Oakland, MD 21550
      216 E Center St, Oakland, MD 21550
      /29

      Est $182,974 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,472 Sq Ft

      216 E Center St, Oakland, MD 21550

      216 E Center St, Oakland, MD 21550
  • 222 Skippers Point Rd, Oakland, MD 21550
    222 Skippers Point Rd, Oakland, MD 21550
    222 Skippers Point Rd, Oakland, MD 21550
    /59

    $779,000

    • 5 Beds
    • 1.5 Baths
    • 1,278 Sq Ft

    222 Skippers Point Rd, Oakland, MD 21550

    Lovely level lot with path to your own private class A dock, directly across the street. This comfy cottage sits on 1.8 level acres with 2 storage garages and mature landscaping. 5BRs, open living, dinning & kitchen area, with lots of sunlight. 1 full & 1-1/2 bath, large closet for storge, laundry room off back of the home. 2 garages with plenty of storge for your lake and yard toys. The lot has

    Julie Mead The KW Collective

    222 Skippers Point Rd, Oakland, MD 21550
  • 341 Doe Dr, Oakland, MD 21550
    341 Doe Dr, Oakland, MD 21550
    341 Doe Dr, Oakland, MD 21550
    /40

    $410,000 Sold Feb 28, 2025

    341 Doe Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 2024

    Last Sold Summary

    • $237/SF
    • 189 Days On Market

    Current Estimated Value $412,777

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

    341 Doe Dr, Oakland, MD 21550
    • 1012 Hemlock Cir, Oakland, MD 21550
      1012 Hemlock Cir, Oakland, MD 21550
      1012 Hemlock Cir, Oakland, MD 21550
      /33

      Est $474,894 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,590 Sq Ft

      1012 Hemlock Cir, Oakland, MD 21550

      1012 Hemlock Cir, Oakland, MD 21550
  • Lot 40 W Big Piney Dr, Oakland, MD 21550
    Lot 40 W Big Piney Dr, Oakland, MD 21550
    Lot 40 W Big Piney Dr, Oakland, MD 21550
    /8

    $17,000

    • Land
    • 0.77 Acre
    • $22,078 per Acre

    Lot 40 W Big Piney Dr, Oakland, MD 21550

    Located in the Youghiogheny Mountain Resort community, this .77ac lot offers the ultimate gateway to peaceful surroundings, beautiful views, and abundant wildlife. Approved for a sand mound sewage system, this lot provides the perfect opportunity to build your future outdoor enthusiast retreat! Enjoy exclusive access to over 50 miles of private roads and trails perfect for ATV and side-by-side

    Elizabeth Broadwater Taylor Made Deep Creek Vacations & Sales

    Lot 40 W Big Piney Dr, Oakland, MD 21550
  • 278 Basswood Way Unit 19, Oakland, MD 21550
    278 Basswood Way Unit 19, Oakland, MD 21550
    278 Basswood Way Unit 19, Oakland, MD 21550
    /37

    $715,000 Sold Jan 30, 2025

    278 Basswood Way Unit 19, Oakland, MD 21550

    • 5 Beds
    • 4 Baths
    • 3,084 Sq Ft
    • Built 2005

    Last Sold Summary

    • $232/SF
    • 87 Days On Market

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

    278 Basswood Way Unit 19, Oakland, MD 21550
    • 1865 Garrett Rd, Oakland, MD 21550
      1865 Garrett Rd, Oakland, MD 21550
      1865 Garrett Rd, Oakland, MD 21550
      /52

      Est $253,072 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,144 Sq Ft

      1865 Garrett Rd, Oakland, MD 21550

      1865 Garrett Rd, Oakland, MD 21550
  • 62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    /30

    $249,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,390 Sq Ft

    62 Wild Turkey Ct, Oakland, MD 21550

    Current new home construction project underway, but Builder not going to complete at this time due too busy. So, ready for who may wish to complete project themselves or have completed by others, or current Builder may consider completing for Buyer. Current structure is a custom engineered modular home. This is not a completed or intended by Builder to be completed house project at this time .

    Chip Smith 1 Real Estate Source LLC

    62 Wild Turkey Ct, Oakland, MD 21550
  • Lot 24 Laurel Dr, Oakland, MD 21550
    Lot 24 Laurel Dr, Oakland, MD 21550
    /2

    $25,000 Sold Apr 24, 2025

    Lot 24 Laurel Dr, Oakland, MD 21550

    • Land
    • 0.58 Acre
    • $43,103 per Acre

    Last Sold Summary

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

    Lot 24 Laurel Dr, Oakland, MD 21550

Showing Results 281 - 320, Page 8 of 18

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