10,771

Oakland, MD Homes

Section Image
  • /8

    $79,900

    Sold Apr 03, 2026

    Lot 2 Pergin Farm Rd, Oakland, MD 21550

    • Land
    • 3.67 Acres
    • $21,771 per Acre

    Last Sold Summary

    • 3 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    Lot 2 Pergin Farm Rd, Oakland, MD 21550
    • /61

      Est $231,107

      Not Listed For Sale

      4368 Underwood Rd, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 1,760 Sq Ft
      • Built 1952
      4368 Underwood Rd, Oakland, MD 21550

      Last Sold Summary

      • 8 Days On Market

  • /59

    $739,000

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft

    12 Arrowhead Ln, Oakland, MD 21550

    Arrowhead 3BR, 3 full BA lakefront, end-unit condo, WITH a dedicated dock slip! Easy walk out to level lakefront just steps to your dock slip! 3 Level unit includes an updated kitchen, cozy wood burning fireplace, multiple living areas, lakefront patio & deck with great water views! Enjoy a private, level lakefront peninsula boasting a large common lakefront area! Surrounded by mature pine trees,

    Julie Mead The KW Collective

    12 Arrowhead Ln, Oakland, MD 21550
  • /92

    $635,000

    Sold Sep 26, 2025

    5 Arrowhead Ln, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft
    • Built 1988

    Last Sold Summary

    • $385/SF
    • 116 Days On Market

    Current Estimated Value $630,227

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    5 Arrowhead Ln, Oakland, MD 21550
    • /83

      Est $1,618,455

      Not Listed For Sale

      2203 Lake Shore Dr, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,403 Sq Ft
      • Built 1984
      2203 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 20 Days On Market

  • /61

    $615,000

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

    308 Winding Trail Ln Unit 11B, Oakland, MD 21550

    5BR, 4.5BA duplex with LAKE VIEWS! Enjoy 3300sf of living space in the heart of Deep Creek Lake. Features include 3 spacious suites, multiple stacked stone fireplaces and two living room areas, plus an impressive outdoor fire pit. You will love the open kitchen/dining area and the covered back deck. Other features include wood floors, granite, instant hot water, pool table and hot tub. Attached

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    308 Winding Trail Ln Unit 11B, Oakland, MD 21550
  • /2

    $280,000

    Sold Feb 23, 2026

    1359 Cedar Ln, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 1,440 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Above List Price
    • $194/SF
    • 8 Days On Market

    Current Estimated Value $280,495

    Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    1359 Cedar Ln, Oakland, MD 21550
    • /51

      Est $313,520

      Not Listed For Sale

      18361 Garrett Hwy, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,112 Sq Ft
      • Built 1977
      18361 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 131 Days On Market

  • /10

    $99,900

    Under Contract
    • Land
    • 1.7 Acres
    • $58,765 per Acre

    0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550

    Ready to bring your Deep Creek Lake dream home to life? This beautiful 1.7-acre lot in the sought after community of Paradise Ridge offers the perfect blend of peace, privacy, and lake access. Spend your summer days down by the water, where owners enjoy access to one of the area’s best lakefront spots, complete with a sandy beach, picnic pavilions, and kayak or swimming areas. When the day winds

    Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550
  • /12

    $154,900

    Sold Aug 25, 2025

    Lots 54 & 53 Sloan Tract Rd, Oakland, MD 21550

    • Land
    • 26,136 Sq Ft
    • $258,167 per Acre

    Last Sold Summary

    • 17 Days On Market

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    Lots 54 & 53 Sloan Tract Rd, Oakland, MD 21550
    • /58

      Est $464,004

      Not Listed For Sale

      2734 Mayhew Inn Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1974
      2734 Mayhew Inn Rd, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • /3

    $115,000

    • Land
    • 1 Acre
    • $115,000 per Acre

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550

    Centrally located 1-acre lake access homesite with a dock slip! This property has endless possibilities to build, and depending on where you decide to position your new home, there could be potential for lake views. Offering public sewer and no HOA fees. The only decision left to be made is what style home you will build. Just minutes to the DCL State Park, several restaurants, convenience store,

    Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550
  • /71

    $899,900

    Sold Jun 26, 2025

    145 Lower Penn Point Dr, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,106 Sq Ft
    • Built 2007

    Last Sold Summary

    • $427/SF
    • 135 Days On Market

    Current Estimated Value $893,249

    Last Listing Agent Emillie Albrecht Real Broker, LLC

    145 Lower Penn Point Dr, Oakland, MD 21550
    • /67

      Est $242,751

      Not Listed For Sale

      655 Bray School Rd, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1984
      655 Bray School Rd, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • /46

    $150,000

    • Land
    • 21.46 Acres
    • $6,990 per Acre

    0 Sanders Ln Unit MDGA2011678, Oakland, MD 21550

    Endless Possibilities on 21.46 Acres! A rare private setting featuring gently rolling, pastoral land along scenic Sanders Lane-just 4 miles from Oakland. Enjoy open fields, and woods on a private and a peaceful setting in a desirable area. Enjoy wide-open skies, room to roam, and the serenity of nature—all within minutes of town conveniences, and all the activities Garrett County has to offer!

    Susan Bell Railey Realty, Inc.

    0 Sanders Ln Unit MDGA2011678, Oakland, MD 21550
  • /58

    $1,425,000

    Sold Oct 28, 2025

    20676 Garrett Hwy, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,280 Sq Ft
    • Built 2015

    Last Sold Summary

    • $625/SF
    • 17 Days On Market

    Current Estimated Value $1,415,082

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    20676 Garrett Hwy, Oakland, MD 21550
    • /38

      Est $238,908

      Not Listed For Sale

      87 Mitchell Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,858 Sq Ft
      • Built 1971
      87 Mitchell Dr, Oakland, MD 21550

      Last Sold Summary

      • 28 Days On Market

  • /41

    $424,900

    New Construction $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    654 N Bradley Ln, Oakland, MD 21550

    NEW CONSTRUCTION from Lyv Homes with anticipated mid-June completion. 3BR/2BA, 1464sf contemporary style home fronting on the 13th hole of the Oakland golf course. This property combines scenic views with modern design and outdoor living. Key features include multiple wood-burning fireplaces, Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets and

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    654 N Bradley Ln, Oakland, MD 21550
  • /35

    $285,000

    Sold Jul 03, 2025

    506 Cedar Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1979

    Last Sold Summary

    • $212/SF
    • 16 Days On Market

    Current Estimated Value $268,746

    Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    506 Cedar Ln, Oakland, MD 21550
    • /5

      Est $138,673

      Not Listed For Sale

      133 Fox Den Rd, Oakland, MD 21550

      • Built 1945
      133 Fox Den Rd, Oakland, MD 21550

      Last Sold Summary

      • 7 Days On Market

  • /57

    $219,000

    • 1 Bed
    • 1.5 Baths
    • 912 Sq Ft

    141 Montana Ln, Oakland, MD 21550

    Nestled on nearly 3 acres across two parcels, this chalet-style home offers a rare opportunity to create your retreat just minutes from the lake. Renovate the existing structure, or start fresh and build the lake-area retreat or cabin you’ve always imagined. The level, wooded setting provides privacy, peace, and plenty of room to expand, garden, or simply enjoy nature. With well and septic

    Larry Smith Railey Realty, Inc.

    141 Montana Ln, Oakland, MD 21550
  • /28

    $339,000

    Sold Aug 01, 2025

    20160 Garrett Hwy Unit H712, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Built 1972

    Last Sold Summary

    • $753/SF
    • 124 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    20160 Garrett Hwy Unit H712, Oakland, MD 21550
    • /53

      Est $1,272,675

      Not Listed For Sale

      483 Skippers Point Rd, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,286 Sq Ft
      • Built 1983
      483 Skippers Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 127 Days On Market

  • /64

    $400,000

    • 2 Beds
    • 1 Bath
    • 1,800 Sq Ft

    2967 Pysell Crosscut Rd, Oakland, MD 21550

    Discover the charm and comfort of this beautifully maintained manufactured home, nestled on a generous 2.07-acre lot. With a unique blend of rustic appeal and modern convenience, this property is perfect for those seeking a serene retreat without sacrificing accessibility. Step inside to find a warm and inviting interior with carpeting and laminate flooring that flows seamlessly throughout. The

    Larry Smith Railey Realty, Inc.

    2967 Pysell Crosscut Rd, Oakland, MD 21550
  • /4

    $3,000

    Sold Oct 24, 2025

    Lot 27 Stool Rock Rd, Oakland, MD 21550

    • Land
    • 22,215 Sq Ft
    • $5,882 per Acre

    Last Sold Summary

    • 67 Days On Market

    Last Listing Agent Elizabeth Broadwater Taylor-Made Deep Creek Real Estate, LLC

    Lot 27 Stool Rock Rd, Oakland, MD 21550
    • /35

      Est $62,547

      Not Listed For Sale

      830 N 4th St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,656 Sq Ft
      • Built 1930
      830 N 4th St, Oakland, MD 21550

      Last Sold Summary

      • 68 Days On Market

  • /2

    $134,000

    • Land
    • 1 Acre
    • $134,000 per Acre

    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550

    Wooded lot with spectacular views of Paradise Point area of lake. Great privacy. Sewer tap available

    John Zorzit Eagle Commercial Realty

    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
  • /113

    $900,000

    Sold Nov 14, 2025

    102 Mountainview Ct, Oakland, MD 21550

    • 7 Beds
    • 4.5 Baths
    • 5,376 Sq Ft
    • Built 2010

    Last Sold Summary

    • $167/SF
    • 139 Days On Market

    Current Estimated Value $1,028,190

    Last Listing Agent Kathy Gibson Railey Realty, Inc.

    102 Mountainview Ct, Oakland, MD 21550
    • /31

      Est $371,294

      Not Listed For Sale

      1793 Kempton Rd, Oakland, MD 21550

      • 5 Beds
      • 1 Bath
      • 2,280 Sq Ft
      • Built 1880
      1793 Kempton Rd, Oakland, MD 21550

      Last Sold Summary

      • 23 Days On Market

  • /8

    $24,900

    • Land
    • 13,503 Sq Ft
    • $80,323 per Acre

    460 W Liberty St, Oakland, MD 21550

    Lot within the town limits of Oakland with water and sewer hookups. This lot had a mobile home that was taken off. According to the owner, both Garrett County Planning and Zoning and the Town of Oakland have indicated that another mobile home can be placed on the lot but it has to be a NEW mobile home. According to P & Z, it must be a new mobile home and will have to be elevated 2' (three blocks)

    Kevin Liller Railey Realty, Inc.

    460 W Liberty St, Oakland, MD 21550
  • /32

    $255,000

    Sold Apr 13, 2026

    6485 Oakland Sang Run Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,170 Sq Ft
    • Built 1966

    Last Sold Summary

    • 7% Below List Price
    • $218/SF
    • 6 Days On Market

    Current Estimated Value $259,070

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

    6485 Oakland Sang Run Rd, Oakland, MD 21550
    • /67

      Est $253,132

      Not Listed For Sale

      218 Weber Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,605 Sq Ft
      • Built 1930
      218 Weber Rd, Oakland, MD 21550

      Last Sold Summary

      • 56 Days On Market

  • /10

    $375,000

    • 5 Beds
    • 1.5 Baths
    • 1,536 Sq Ft

    511 Main St, Oakland, MD 21550

    The property offered for sale is 32.20 acres located on the southwest & northwest corners of Maryland Highway, State Route 135 at Main Street & Sand Flat Road, Deer Park. The Single Family Residence built in 1920 has 5 bedrooms, 1 full bathroom and 1 half bathroom. The residence is being sold "As Is". The residence is prime for renovation; the parcel may have commercial potential. The current

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    511 Main St, Oakland, MD 21550
  • /51

    $180,000

    Sold Mar 20, 2026

    565 Glendale Rd Unit 204B, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 460 Sq Ft
    • Built 2006

    Last Sold Summary

    • $391/SF
    • 83 Days On Market

    Last Listing Agent Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 204B, Oakland, MD 21550
    • /71

      Est $843,019

      Not Listed For Sale

      589 Mountainview Dr, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 2,665 Sq Ft
      • Built 1993
      589 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 247 Days On Market

  • /6

    $4,000

    • Land
    • 20,037 Sq Ft
    • $8,696 per Acre

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550

    Here is an affordable chance to own a lot and have access to all of Youghiogheny Mountain Resort's beautiful and fun amenities!

    Jonathan Price Railey Realty, Inc.

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550
  • /10

    $240,000

    Sold Apr 01, 2026

    Lot G Randall Way, Oakland, MD 21550

    • Land
    • 2.07 Acres
    • $115,942 per Acre

    Last Sold Summary

    • 47% Below List Price
    • 352 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    Lot G Randall Way, Oakland, MD 21550
    • /100

      Est $407,009

      Not Listed For Sale

      3241 Pleasant Valley Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,496 Sq Ft
      • Built 1972
      3241 Pleasant Valley Rd, Oakland, MD 21550

      Last Sold Summary

      • 69 Days On Market

  • /28

    $185,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft

    512 Roanoke Ave, Oakland, MD 21550

    The first thing you will notice as you approach 512 Roanoke Ave in loch Lynn heights is the towering maple trees lining the street. (In early spring they provide syrup for a lucky few!) Framing this post-card perfect snap shot is a park on either side. The Loch Lynn Wetlands Trail is the beating heart of the neighborhood, and the Loch Lynn Community Park and Pavillion hosts the annual town

    Brady Harden Coldwell Banker Premier

    512 Roanoke Ave, Oakland, MD 21550
  • /98

    $399,000

    Sold Feb 13, 2026

    180 Paradise Ridge Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1979

    Last Sold Summary

    • $346/SF
    • 334 Days On Market

    Current Estimated Value $420,348

    Last Listing Agent Justin Liller Railey Realty, Inc.

    180 Paradise Ridge Rd, Oakland, MD 21550

Showing Results 161 - 200, Page 5 of 18

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