10,549

Oakland, MD Homes

Section Image
  • /28

    $199,900

    • Land
    • 3.32 Acres
    • $60,211 per Acre

    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550

    OAKLAND, MD – 3.318 UNRESTRICTED ACRES “READY TO BUILD” THAT VACATION HOME OR FULL TIME RESIDENCE. THE SUBJECT PROPERTY IS IN THE DEEP CREEK LAKE RESORT AREA. ALL AMENITIES ASSOCIATED WITH A MAJOR RESORT AREA ARE WITHIN A SHORT DRIVE OF THE SUBJECT PROPERTY. FULLY WOODED. MATURE HARDWOOD THRU-OUT. LEVEL TOPOGRAPHY. CLOSE PROXIMITY TO BOAT LAUNCH.

    Mike Haywood The Mike Haywood Group

    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
  • /47

    $285,000

    Sold Oct 31, 2025

    1764 Underwood Rd, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,304 Sq Ft
    • Built 1968

    Last Sold Summary

    • $124/SF
    • 175 Days On Market

    Current Estimated Value $292,198

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

    1764 Underwood Rd, Oakland, MD 21550
    • /64

      Est $228,931

      Not Listed For Sale

      324 W Liberty St, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,725 Sq Ft
      • Built 1900
      324 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /69

    $699,000

    • 5 Beds
    • 3 Baths
    • 2,560 Sq Ft

    170 Cherrywood Dr, Oakland, MD 21550

    Private Mountain Retreat on 8+ Acres Near Oakland Discover the peace and beauty of Garrett County living on over 8 private wooded acres filled with mountain views, abundant wildlife, and endless opportunities to enjoy the outdoors. Deer, turkey, songbirds, and other native wildlife are frequent visitors, creating a true nature lover's paradise. Conveniently located just minutes from Oakland's

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    170 Cherrywood Dr, Oakland, MD 21550
  • /52

    $920,000

    Sold Jun 15, 2026

    1295 Mountainview Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 3,550 Sq Ft
    • Built 2003

    Last Sold Summary

    • $259/SF
    • 3 Days On Market

    Current Estimated Value $924,656

    Last Listing Agent Debbie Roberts Long & Foster Real Estate, Inc.

    1295 Mountainview Dr, Oakland, MD 21550
    • /83

      Est $1,204,751

      Not Listed For Sale

      2675 Stockslager Rd, Oakland, MD 21550

      • 4 Beds
      • 4.5 Baths
      • 3,024 Sq Ft
      • Built 2003
      2675 Stockslager Rd, Oakland, MD 21550

      Last Sold Summary

      Last Listing Agent Russell Bounds Railey Realty, Inc.

  • /31

    $430,000

    • 5 Beds
    • 2.5 Baths
    • 2,507 Sq Ft

    704 Old Crellin Rd, Oakland, MD 21550

    Beautiful five-bedroom, 2.5-bath home situated on four acres in a peaceful country setting, yet conveniently located just two miles from town limits.The main level features three bedrooms, a spacious sunroom, living room, kitchen, separate dining area, full bathroom, and half bath. The lower level offers both interior and exterior access and includes a large family room, two additional

    Andrew Orr The KW Collective

    704 Old Crellin Rd, Oakland, MD 21550
  • /56

    $697,000

    Sold Dec 19, 2025

    969 Hoyes Run Rd, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,614 Sq Ft
    • Built 1998

    Last Sold Summary

    • $193/SF
    • 180 Days On Market

    Current Estimated Value $741,572

    Last Listing Agent Roberta McNamara RE/MAX Results

    969 Hoyes Run Rd, Oakland, MD 21550
    • /75

      Est $707,061

      Not Listed For Sale

      630 Paradise Ridge Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,044 Sq Ft
      • Built 1997
      630 Paradise Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /32

    $299,900

    $29K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 780 Sq Ft

    565 Glendale Rd Unit B206, Oakland, MD 21550

    Charming true 1-bedroom + loft (can be used as 2nd bedroom) condo at Silver Tree Suites, LAKEFRONT living at its finest! This spacious second-floor unit features a private balcony, fully equipped kitchenette, cozy gas fireplace and abundant natural light. Enjoy resort-style amenities including a fitness center, sauna, on-site laundry and game room, plus steps-away fine dining at Dutch’s at Silver

    Carlos Espinoza Jason Mitchell Group

    565 Glendale Rd Unit B206, Oakland, MD 21550
  • /29

    $225,000

    Sold Nov 17, 2025

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550

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

    Last Sold Summary

    • $433/SF
    • 26 Days On Market

    Current Estimated Value $234,056

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    • /4

      Est $107,712

      Not Listed For Sale

      111 W Liberty St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,528 Sq Ft
      • Built 1914
      111 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Adam Shpritz Ashland Auction Group LLC

  • /24

    $1,025,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    127 Paradise Heights, Oakland, MD 21550

    Beautifully renovated lake access log cabin with a deeded dock slip in a quiet cove with private 29 acres of trails (ATVs/snowmobiles permitted). Recent renovations (approx. $200K) include new wrap around deck, new roof, re-stained siding, new kitchen with granite counters, new appliances, new bathrooms, new LVFs throughout the house, new 2 car garage doors, new mini-split heat and A/C units, and

    Norman Domingo XRealty.NET LLC

    127 Paradise Heights, Oakland, MD 21550
  • /39

    $195,000

    Sold Nov 12, 2025

    501 Christophers Way, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • Built 1994

    Last Sold Summary

    • $121/SF
    • 138 Days On Market

    Last Listing Agent Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    501 Christophers Way, Oakland, MD 21550
    • /25

      Est $1,092,942

      Not Listed For Sale

      378 Lower Penn Point Dr, Oakland, MD 21550

      • 4 Beds
      • 1 Bath
      • 1,114 Sq Ft
      • Built 1950
      378 Lower Penn Point Dr, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • /19

    $185,000

    Under Contract
    • Land
    • 1.35 Acres
    • $137,037 per Acre

    0 Pysell Crosscut Rd Unit MDGA2012040, Oakland, MD 21550

    Discover the perfect canvas for your dream home on this expansive 1.35-acre parcel of land, where possibilities abound and nature's beauty surrounds you. Nestled in a serene setting, this property offers a unique opportunity to create a personalized retreat tailored to your lifestyle. Imagine waking up each morning to the gentle rustle of leaves and the soft sounds of nature, all while being just

    Larry Smith Railey Realty, Inc.

    0 Pysell Crosscut Rd Unit MDGA2012040, Oakland, MD 21550
  • /41

    $218,000

    Sold Dec 01, 2025

    1136 Black Oak Dr, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1971

    Last Sold Summary

    • $206/SF
    • 7 Days On Market

    Current Estimated Value $237,755

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

    1136 Black Oak Dr, Oakland, MD 21550
    • /89

      Est $1,698,289

      Not Listed For Sale

      1019 Lake Shore Dr, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 2,605 Sq Ft
      • Built 1962
      1019 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Susan Bell Railey Realty, Inc.

  • /42

    $139,900

    Under Contract
    • 2 Beds
    • 1 Bath
    • 816 Sq Ft

    509 E St, Oakland, MD 21550

    Charming 2-bedroom, 1-bath home in Mountain Lake Park, MD, featuring gorgeous hardwood floors throughout, a large covered front porch, and a fully fenced backyard perfect for pets, kids, or relaxing outdoors. The home is connected to public water, sewer, and natural gas for added convenience. Conveniently located just minutes from Garrett Regional Medical Center, nearby grocery stores, and

    Brent Housley Railey Realty, Inc.

    509 E St, Oakland, MD 21550
  • /18

    $200,000

    Sold Sep 15, 2025

    2571 Shady Dell Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • Built 1985

    Last Sold Summary

    • $119/SF
    • 62 Days On Market

    Current Estimated Value $255,686

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    2571 Shady Dell Rd, Oakland, MD 21550
    • /65

      Est $148,534

      Not Listed For Sale

      94 Tannery Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,108 Sq Ft
      • Built 1900
      94 Tannery Rd, Oakland, MD 21550

      Last Sold Summary

      • 63 Days On Market

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /28

    $160,000

    • Land
    • 3.04 Acres
    • $52,632 per Acre

    132 &132A Tarn Dr, Oakland, MD 21550

    Lake Access Lots 132 & 132A in the Mountainside Community offer 3.04 acres of privacy at the end of a quiet cul-de-sac on Tarn Drive. Combined and recorded in the land records as one building site, this property is already serviced by public water and sewer—making it ready for your future build. The gently wooded setting provides a peaceful, natural backdrop with plenty of space to design your

    Rich Orr Railey Realty, Inc.

    132 &132A Tarn Dr, Oakland, MD 21550
  • /93

    $1,445,000

    Sold Nov 14, 2025

    128 Big Bass Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,305 Sq Ft
    • Built 2023

    Last Sold Summary

    • $336/SF
    • 13 Days On Market

    Current Estimated Value $1,470,926

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    128 Big Bass Dr, Oakland, MD 21550
    • /68

      Est $332,416

      Not Listed For Sale

      707 Sunshine Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,052 Sq Ft
      • Built 2004
      707 Sunshine Dr, Oakland, MD 21550

      Last Sold Summary

      • 94 Days On Market

      Last Listing Agent Tyler Burch Burch Real Estate Group, LLC

  • /21

    $99,000

    • Land
    • 1.84 Acres
    • $53,804 per Acre

    0 Robinwood Dr Unit 13, Oakland, MD 21550

    RARE opportunity to own a Youghiogheny river access lot! Lot 13 is a 1.84 AC building lot with seasonal & filtered views of the water. River Run is an exclusive and highly sought-after waterfront community with a common access area that feels like a private park setting. Benches & picnic tables adorn a grassy, mostly level shoreline area along the river. Lot is perc approved for a three bedroom

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    0 Robinwood Dr Unit 13, Oakland, MD 21550
  • /56

    $320,000

    Sold Nov 05, 2025

    531 S 3rd St, Oakland, MD 21550

    • 5 Beds
    • 2.5 Baths
    • 2,477 Sq Ft
    • Built 1920

    Last Sold Summary

    • $129/SF
    • 118 Days On Market

    Current Estimated Value $333,964

    Last Listing Agent Jennifer Jackson Charis Realty Group

    531 S 3rd St, Oakland, MD 21550
    • /66

      Est $191,824

      Not Listed For Sale

      1606 Wheeling Ave, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,502 Sq Ft
      • Built 1976
      1606 Wheeling Ave, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Kevin Liller Railey Realty, Inc.

  • /60

    $799,900

    New Construction Pending
    • 4 Beds
    • 4 Baths

    15 Byran Dr, Oakland, MD 21550

    Experience modern mountain living in this brand-new 2026 construction. This beautifully designed 4-bedroom, 4-bath home offers two spacious levels, quality finishes, and plenty of room for family and guests. Open layout with modern kitchen, island bar, and stone fireplace. Stamped concrete patio with covered fireplace and outdoor kitchen. Over half an acre of private wooded mountain-top space

    Jon Bell Railey Realty, Inc.

    15 Byran Dr, Oakland, MD 21550
  • /71

    $590,000

    Sold Jan 16, 2026

    3084 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,464 Sq Ft
    • Built 1999

    Last Sold Summary

    • $239/SF
    • 305 Days On Market

    Current Estimated Value $653,128

    Last Listing Agent Jon Bell Railey Realty, Inc.

    3084 Lake Shore Dr, Oakland, MD 21550
    • /69

      Est $852,521

      Not Listed For Sale

      79 Hummingbird Ct, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,800 Sq Ft
      • Built 1999
      79 Hummingbird Ct, Oakland, MD 21550

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Jessie Railey Railey Realty, Inc.

  • /6

    $175,000

    • Land
    • 3.46 Acres
    • $50,578 per Acre

    0 Robinwood Dr Unit 9, Oakland, MD 21550

    Rare riverfront building lot on the Youghiogheny river offering 175+ feet of water frontage on 3.46 acres. Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. Enjoy a picturesque setting in a riverfront setting with NO HOA restraints. Perc approved. While parts of this lot may be in the flood plain, the

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    0 Robinwood Dr Unit 9, Oakland, MD 21550
  • /30

    $17,000

    Sold May 28, 2026

    Lots 37 & 38 Fir Tree Dr, Oakland, MD 21550

    • Land
    • 1.58 Acres
    • $10,759 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 12 Days On Market

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

    Lots 37 & 38 Fir Tree Dr, Oakland, MD 21550
    • /86

      Est $806,200

      Not Listed For Sale

      105 Meadow Ct, Oakland, MD 21550

      • 4 Beds
      • 6 Baths
      • 3,192 Sq Ft
      • Built 2004
      105 Meadow Ct, Oakland, MD 21550

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /64

    $1,400,000

    • 5 Beds
    • 3.5 Baths
    • 2,832 Sq Ft

    827 Penn Point Rd, Oakland, MD 21550

    Custom built by the original owners and thoughtfully expanded with a recent addition, this exceptional five-bedroom, 3.5-bath home is set on 100 feet of split lakefront in desirable Penn Cove. Featuring a coveted Type A dock permit, lakeside fire pit and pavilion, and easy shoreline access, the property is designed to embrace lake living in every season. Set on a generously sized lot with

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

    827 Penn Point Rd, Oakland, MD 21550
  • /80

    $893,000

    Sold Aug 05, 2026

    208 Cliff Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,219 Sq Ft
    • Built 1997

    Last Sold Summary

    • 6% Below List Price
    • $402/SF
    • 15 Days On Market

    Current Estimated Value $946,554

    Last Listing Agent Kellyann Green Railey Realty, Inc.

    208 Cliff Dr, Oakland, MD 21550
    • /59

      Est $431,833

      Not Listed For Sale

      57 Allegro Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,524 Sq Ft
      • Built 2004
      57 Allegro Ln, Oakland, MD 21550

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Chris Nichols Taylor-Made Deep Creek Real Estate, LLC

  • /68

    $789,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    116 Wanderer Ln, Oakland, MD 21550

    Rare opportunity to own at Deep Creek Lake's most enjoyable and desirable condominium spot, Four Hooppole Spot. Located on the southern end of the lake, including prime lake frontage, a private beach and beautiful views and sunsets, Four Hooppole South is certainly a one of a kind living experience.Unit F5 offers a great setting and is situated close to the dock area where your assigned

    Bill Weissgerber Railey Realty, Inc.

    116 Wanderer Ln, Oakland, MD 21550
  • /35

    $285,000

    Sold Nov 13, 2025

    473 Cumberland Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,389 Sq Ft
    • Built 1989

    Last Sold Summary

    • $205/SF
    • 155 Days On Market

    Current Estimated Value $316,557

    Last Listing Agent Jeremy McDonough Mr. Lister Realty

    473 Cumberland Rd, Oakland, MD 21550
    • /73

      Est $702,910

      Not Listed For Sale

      491 Edens Ridge Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 3,318 Sq Ft
      • Built 2003
      491 Edens Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Julie Mead The KW Collective

  • /57

    $575,000

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,340 Sq Ft

    193 Red Run Rd Unit 1B3, Oakland, MD 21550

    Ultimate lakefront living awaits at Red Run! This stunning 2-3BR, 2BA condo features a second-floor loft and a versatile den easily used as a 3rd bedroom. Enjoy breathtaking lake views from your gorgeous primary suite and private lakeside balcony. Extensively upgraded with a extensively upgraded kitchen boasting granite countertops and soft-close cabinetry, a newly remodeled laundry room with a

    John McNamara RE/MAX Results

    193 Red Run Rd Unit 1B3, Oakland, MD 21550

Showing Results 481 - 520, Page 13 of 18

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