10,739

Oakland, MD Homes

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  • /8

    $99,000 Sold Jan 30, 2026

    125 N 2nd St, Oakland, MD 21550

    • Land
    • 0.22 Acre
    • $450,000 per Acre

    Last Sold Summary

    • 38 Days On Market

    Current Estimated Value $100,594

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    125 N 2nd St, Oakland, MD 21550
    • /82

      Est $1,625,866 Not Listed For Sale

      1597 Lake Shore Dr, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 1,904 Sq Ft
      • Built 2006
      1597 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 4% Below List Price
      • $893/SF
      • 2 Days On Market

      Last Sold Price $1,700,000

      Last Listing Agent Kathy Gibson Railey Realty, Inc.

  • /10

    $59,900 Under Contract

    • 768 Sq Ft

    114 C St, Oakland, MD 21550

    24x32 garage with heat (propane tank needed), electric service and finished at a very high level inside with metal ceilings, drywall and slab concrete floor. This level lot has both public water & sewer hookups, and can be used as-is or improved upon. Verify with town of Mountain Lake Park for costs to connect to water/sewer and any specifics on how the property would transition to a buildable

    Jay Ferguson Taylor Made Deep Creek Real Estate

    114 C St, Oakland, MD 21550
  • /114

    $1,000,000 Sold Feb 05, 2026

    1720 Pysell Crosscut Rd, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 8,000 Sq Ft
    • Built 1976

    Last Sold Summary

    • $125/SF
    • 52 Days On Market

    Current Estimated Value $527,201

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

    1720 Pysell Crosscut Rd, Oakland, MD 21550
    • /29

      Est $184,107 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

      • 2% Above List Price
      • $122/SF
      • 4 Days On Market

      Last Sold Price $180,000

      Last Listing Agent Sheila Howell Lake Homes Realty, LLC

  • /17

    $765,000

    • 4 Beds
    • 3 Baths
    • 2,112 Sq Ft

    519 Paradise Heights, Oakland, MD 21550

    Secluded 4 bedroom 3 bath log home with lake access and single dock slip located in the heart of Deep Creek Lake Resort Area Full unfinished basement, front covered porch and rear deck. Call Office for particulares.

    Linda Deremer Appalachian Realty

    519 Paradise Heights, 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
    • /33

      Est $433,167 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

      • 2% Above List Price
      • $267/SF
      • 35 Days On Market

      Last Sold Price $425,000

      Last Listing Agent Autumn McDaniel The KW Collective

  • /18

    $4,000

    • Land
    • 0.47 Acre
    • $8,511 per Acre

    Lot 36 Fox Tail Rd, Oakland, MD 21550

    Discover your mountain escape in Yough Mountain Resort, a gated recreational community in the scenic mountains of Western Maryland, just a short drive to Deep Creek Lake. This amenity-rich community is designed for outdoor enthusiasts, offering ATV and snowmobile trails, Yough River access, nearby state parks, hunting opportunities, plus a playground and pavilion area for gathering.This

    Shannon McWilliams The KW Collective

    Lot 36 Fox Tail Rd, 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 $1,280,064

    Last Listing Agent Lauren McCann Railey Realty, Inc.

    215 Lower Penn Point Dr, Oakland, MD 21550
    • /7

      Est $332,495 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

      • 15% Below List Price
      • $734/SF
      • 0 Days On Market

      Last Sold Price $389,000

      Last Listing Agent Russell Bounds Railey Realty, Inc.

  • /115

    $2,350,000

    • 5 Beds
    • 6.5 Baths
    • 5,376 Sq Ft

    2725 Stockslager Rd, Oakland, MD 21550

    Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This custom-built log home is set against a picturesque landscape in Western Maryland, offering breathtaking nature views and embodying mountain charm and adventure. This home showcases impeccable craftsmanship, seamlessly blending with its natural surroundings while providing unrivaled comfort. Nestled on 1.03

    Shelia McCracken Taylor Made Deep Creek Real Estate

    2725 Stockslager Rd, Oakland, MD 21550
  • /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 $2,848,937

    Last Listing Agent Susan Bell Railey Realty, Inc.

    56 Bee Tree Ln, Oakland, MD 21550
    • /52

      Est $239,623 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

      • 2% Above List Price
      • $205/SF
      • 19 Days On Market

      Last Sold Price $235,000

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

  • /33

    $875,000

    • 3 Beds
    • 3.5 Baths
    • 3,897 Sq Ft

    39 Leo Friend Rd, Oakland, MD 21550

    **In the process of having new pictures taken. To see the pictures on the prior listing, go to MSL listing

    Andrew Orr The KW Collective

    39 Leo Friend Rd, 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 $246,646

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

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    • /70

      Est $1,647,229 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

      • 3% Below List Price
      • $862/SF
      • 5 Days On Market

      Last Sold Price $1,692,500

      Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

  • /5

    $27,500

    • Land
    • 0 Acre

    Lot 54 Gallatin Spur Rd, Oakland, MD 21550

    Building lot located in the premier subdivision - Gallatin Woods! This beautifully wooded community is located in the heart of the Deep Creek Lake. This is a condominium ownership type in regards to the land itself, but is buildable for a single family home! There are 8 pre-approved building plans designed and engineered by Mountaineer Log Homes that range anywhere from 1571 to 3908 square feet.

    Nina Beitzel Railey Realty, Inc.

    Lot 54 Gallatin Spur Rd, 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
    • /71

      Est $745,308 Not Listed For Sale

      10 Ortiz Ct, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 3,440 Sq Ft
      • Built 2005
      10 Ortiz Ct, Oakland, MD 21550

      Last Sold Summary

      • 26% Above List Price
      • $171/SF
      • 181 Days On Market

      Last Sold Price $589,900

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /22

    $207,500

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft

    1307 Broadford Rd, Oakland, MD 21550

    Nestled in the scenic countryside of Oakland, this charming ready to move in 2 bed 1 Bath home offers the perfect blend of privacy, space, and small-town convenience. Situated on a beautiful property along Broadford Road, the home provides peaceful surroundings while remaining just minutes from downtown Oakland, schools, shopping, and plenty of outdoor recreation areas.. Properties in this area

    Bill Kenny Keller Williams Realty Centre

    1307 Broadford Rd, 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 $451,861

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    50 Village Dr Unit 7, Oakland, MD 21550
    • /41

      Est $369,016 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

      • 25% Above List Price
      • $132/SF
      • 45 Days On Market

      Last Sold Price $295,000

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /22

    $60,000

    • 2 Beds
    • 1 Bath
    • 1,600 Sq Ft

    422 Maple Ave, Oakland, MD 21550

    Investor opportunity in a highly desirable location! This property has been gutted and is ready for your vision. A rare chance to renovate and customize to your exact specifications. Ideal for resale, rental investment, or personal use. Ideally located near Loch Lynn Heights Wetland Trails, soccer complex, and community park. Great potential for the right buyer. RAILEY REALTY IS NOT THE CARETAKER

    Nicole Jackson Railey Realty, Inc.

    422 Maple Ave, 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 $572,532

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    • /83

      Est $2,484,957 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

      • 10% Below List Price
      • $1,164/SF
      • 111 Days On Market

      Last Sold Price $2,750,000

      Last Listing Agent Lauren McCann Railey Realty, Inc.

  • /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
  • /13

    $155,000 Sold Jan 08, 2026

    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550

    • Land
    • 0.72 Acre
    • $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
    • /95

      Est $548,821 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

      • 12% Above List Price
      • $216/SF
      • 5 Days On Market

      Last Sold Price $490,000

      Last Listing Agent Susan Bell Railey Realty, Inc.

  • /5

    $25,000

    • Land
    • 0.34 Acre
    • $73,529 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
  • /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 $569,633

    Last Listing Agent Andrew Orr The KW Collective

    710 Hunters Ridge Dr, Oakland, MD 21550
    • /73

      Est $1,040,535 Not Listed For Sale

      144 Middleton Rd, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,440 Sq Ft
      • Built 1990
      144 Middleton Rd, Oakland, MD 21550

      Last Sold Summary

      • 16% Above List Price
      • $369/SF
      • 4 Days On Market

      Last Sold Price $899,900

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /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
  • /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 $253,056

    Last Listing Agent Susan Bell Railey Realty, Inc.

    655 Bray School Rd, Oakland, MD 21550
    • /58

      Est $1,485,585 Not Listed For Sale

      2411 Lake Shore Dr, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 3,200 Sq Ft
      • Built 1979
      2411 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 17% Below List Price
      • $562/SF
      • 14 Days On Market

      Last Sold Price $1,800,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /30

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 3,278 Sq Ft

    267 San Francisco St, Oakland, MD 21550

    Welcome to your secluded Deep Creek retreat! This stunning property offers expansive lake views! So clear you’ll catch the slopes of Wisp in the distance. Includes 3 lots and the privacy is unmatched. This house was torn down to the foundation and a new house was built in 2009. Inside, you’ll find four spacious bedrooms, two and a half baths, and soaring vaulted ceilings and a grand fireplace.

    Bradley West HomeSmart

    267 San Francisco St, 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
    • /132

      Est $3,605,953 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

      • 2% Above List Price
      • $387/SF
      • 15 Days On Market

      Last Sold Price $3,537,000

      Last Listing Agent Melissa Goodfellow Railey Realty, Inc.

  • /50

    $359,000

    • 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 Real Estate

    961 Cedar Ln, 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 $650,142

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    155 Basswood Way, Oakland, MD 21550

Showing Results 281 - 320, Page 8 of 18

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