10,549

Oakland, MD Homes

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  • /38

    $265,000

    Sold Dec 30, 2025

    968 Hutton Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 2012

    Last Sold Summary

    • $148/SF
    • 25 Days On Market

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    968 Hutton Rd, Oakland, MD 21550
    • /125

      Est $2,288,122

      Not Listed For Sale

      427 Lake Shore Dr, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 4,584 Sq Ft
      • Built 1987
      427 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /5

    $27,500

    • Land
    • 0 Sq Ft

    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
  • /50

    $1,200,000

    Sold Jun 30, 2026

    209 Black Angus Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,156 Sq Ft
    • Built 1991

    Last Sold Summary

    • $1,038/SF
    • 0 Days On Market

    Current Estimated Value $1,175,618

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    209 Black Angus Dr, Oakland, MD 21550
    • /65

      Est $3,864,736

      Not Listed For Sale

      2276 Paradise Point Rd, Oakland, MD 21550

      • 8 Beds
      • 5.5 Baths
      • 8,453 Sq Ft
      • Built 2006
      2276 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

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

  • /25

    $249,900

    • 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
  • /18

    $3,500

    Sold Jun 24, 2026

    Lot 36 Fox Tail Rd, Oakland, MD 21550

    • Land
    • 20,473 Sq Ft
    • $7,447 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 107 Days On Market

    Last Listing Agent Shannon McWilliams Taylor-Made Deep Creek Real Estate, LLC

    Lot 36 Fox Tail Rd, Oakland, MD 21550
    • /56

      Est $370,576

      Not Listed For Sale

      5289 Oakland Sang Run Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,638 Sq Ft
      • Built 2006
      5289 Oakland Sang Run Rd, Oakland, MD 21550

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /24

    $398,000

    $21K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    560 Glendale Rd, Oakland, MD 21550

    Charming vintage Deep Creek Lake log cabin ideally located in the heart of Deep Creek Lake just minutes from area amenities. Full of character and thoughtfully restored, this established rental property is being sold completely furnished and turnkey. Enjoy filtered lake views from the inviting covered front porch, then unwind in the hot tub or gather around the fire pit after a day on the lake.

    Lauren McCann Railey Realty, Inc.

    560 Glendale Rd, Oakland, MD 21550
  • /21

    $295,000

    Sold Dec 23, 2025

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 752 Sq Ft
    • Built 1997

    Last Sold Summary

    • $392/SF
    • 21 Days On Market

    Current Estimated Value $304,865

    Last Listing Agent James Matthews Taylor-Made Deep Creek Real Estate, LLC

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    • /65

      Est $154,426

      Not Listed For Sale

      620 E Green St, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,668 Sq Ft
      • Built 1922
      620 E Green St, Oakland, MD 21550

      Last Sold Summary

      • 81 Days On Market

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

  • /52

    $225,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,260 Sq Ft

    210 F St, Oakland, MD 21550

    Welcome to 210 F St! This well-maintained 3-bedroom, 1-bath home offers a functional two-level floor plan with a partially finished basement, providing flexible living and storage space. Recent improvements, including a new roof and replacement windows, add value and peace of mind. Enjoy outdoor living from the covered front porch, covered back porch, or spacious rear deck overlooking the

    Zach Wesolowski Railey Realty, Inc.

    210 F St, Oakland, MD 21550
  • /50

    $567,500

    Sold Mar 13, 2026

    189 Red Run Rd Unit 1C2, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Below List Price
    • $473/SF
    • 227 Days On Market

    Current Estimated Value $563,205

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    189 Red Run Rd Unit 1C2, Oakland, MD 21550
    • /76

      Est $206,856

      Not Listed For Sale

      501 G St, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,520 Sq Ft
      • Built 1979
      501 G St, Oakland, MD 21550

      Last Sold Summary

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /104

    $948,000

    $50K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 5,547 Sq Ft

    17240 Garrett Hwy, Oakland, MD 21550

    Luxury Living Meets Timeless Country Charm! Perfectly positioned on 10.33 picturesque acres between Oakland and Deep Creek Lake, this exceptional 6-bedroom, 4.5-bath home offers the ideal blend of refined comfort, modern updates, and peaceful privacy. Step inside to discover an inviting open floor plan highlighted by soaring wood ceilings, a dramatic floor-to-ceiling stone fireplace, and

    Justin Liller Railey Realty, Inc.

    17240 Garrett Hwy, Oakland, MD 21550
  • /44

    $145,000

    Sold Jul 03, 2026

    1099 Table Rock Rd, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 1,728 Sq Ft
    • Built 1940

    Last Sold Summary

    • $84/SF
    • 0 Days On Market

    Current Estimated Value $131,026

    Last Listing Agent Rich Orr Railey Realty, Inc.

    1099 Table Rock Rd, Oakland, MD 21550
    • /42

      Est $173,726

      Not Listed For Sale

      603 Oak St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,200 Sq Ft
      • Built 1965
      603 Oak St, Oakland, MD 21550

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Andrew Orr The KW Collective

  • /12

    $39,000

    • Land
    • 1.02 Acres
    • $38,235 per Acre

    Lot 14 Warnick Way, Oakland, MD 21550

    Enjoy scenic mountain views from this 1.02 acre mostly wooded homesite. This property offers a peaceful setting with convenient access off Spring Glade Road and is ideally located between Oakland and Deep Creek Lake. No HOA and mobile homes are not permitted, helping maintain the character of the area. Do not miss this great opportunity to build your getaway or full time residence. Contact me

    Nicole Jackson Railey Realty, Inc.

    Lot 14 Warnick Way, Oakland, MD 21550
  • /67

    $1,542,000

    Sold Nov 13, 2025

    1567 Pergin Farm Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,200 Sq Ft
    • Built 2002

    Last Sold Summary

    • $482/SF
    • 15 Days On Market

    Current Estimated Value $1,634,779

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1567 Pergin Farm Rd, Oakland, MD 21550
    • /6

      Est $664,777

      Not Listed For Sale

      20488 Garrett Hwy, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 840 Sq Ft
      • Built 1946
      20488 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 125 Days On Market

      Last Listing Agent Michael Cumerlato Jason Mitchell Group

  • /24

    $18,000

    • Land
    • 26,136 Sq Ft
    • $30,000 per Acre

    22 Elm Dr, Oakland, MD 21550

    Build your dream getaway in the gated community of Youghiogheny Mountain Resort! This flat 0.60-acre lot offers an ideal setting for easy building. Perfect for a full-time home or weekend retreat. Enjoy miles of ATV trails, hunting, and fishing, all while being just minutes from Wisp Resort, Deep Creek Lake, and Swallow Falls State Park. Approved for a sand mound septic system and located within

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    22 Elm Dr, Oakland, MD 21550
  • /50

    $295,000

    Sold May 20, 2026

    163 Crestview Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,416 Sq Ft
    • Built 1997

    Last Sold Summary

    • $208/SF
    • 275 Days On Market

    Current Estimated Value $287,402

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

    163 Crestview Dr, Oakland, MD 21550
    • /80

      Est $716,550

      Not Listed For Sale

      1489 Mountainview Dr, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 3,066 Sq Ft
      • Built 2001
      1489 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 170 Days On Market

      Last Listing Agent Larry Smith Railey Realty, Inc.

  • /14

    $119,900

    Pending
    • Land
    • 28,749 Sq Ft
    • $181,667 per Acre

    20 Fern Loop, Oakland, MD 21550

    Experience mountain living at its finest on this exceptional .65-acre level homesite in the sought-after Sandy Shores Heights community. Perfectly positioned on Wisp Mountain, this property offers a beautiful setting near hole #12 and the tee hole on #13 on the renowned Lodestone Golf Course and is just minutes from year-round recreation, including skiing, golf, hiking, and whitewater adventures.

    Jon Bell Railey Realty, Inc.

    20 Fern Loop, Oakland, MD 21550
  • /65

    $537,000

    Sold Feb 27, 2026

    77 Meadow Ct, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,436 Sq Ft
    • Built 2006

    Last Sold Summary

    • $220/SF
    • 100 Days On Market

    Current Estimated Value $595,222

    Last Listing Agent Jon Bell Railey Realty, Inc.

    77 Meadow Ct, Oakland, MD 21550
    • /85

      Est $1,765,835

      Not Listed For Sale

      739 Glendale Rd, Oakland, MD 21550

      • 6 Beds
      • 6.5 Baths
      • 4,160 Sq Ft
      • Built 2003
      739 Glendale Rd, Oakland, MD 21550

      Last Sold Summary

      • 90 Days On Market

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

  • /6

    $40,000

    • Land
    • 3.46 Acres
    • $11,561 per Acre

    0 Grey Squirrel Rd, Oakland, MD 21550

    Discover the perfect opportunity to own nearly 3.5 acres in the beautiful Youghiogheny Mountain Resort! This spacious vacant lot offers a peaceful mountain setting with plenty of room to create your ideal getaway, vacation retreat, or future home. Outdoor enthusiasts will love the recreational opportunities nearby, including 50+ miles of ATV riding, hiking, snowmobiling, fishing and hunting.

    Danielle Tasker Taylor-Made Deep Creek Real Estate, LLC

    0 Grey Squirrel Rd, Oakland, MD 21550
  • /60

    $505,000

    Sold Nov 14, 2025

    36 Ridgewood Dr, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 1,713 Sq Ft
    • Built 2000

    Last Sold Summary

    • $295/SF
    • 228 Days On Market

    Current Estimated Value $540,895

    Last Listing Agent Larry Smith Railey Realty, Inc.

    36 Ridgewood Dr, Oakland, MD 21550
    • /73

      Est $244,100

      Not Listed For Sale

      723 E Alder St, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft
      • Built 1950
      723 E Alder St, Oakland, MD 21550

      Last Sold Summary

      Last Listing Agent Jesse Shimrock Railey Realty, Inc.

  • /56

    $299,000

    • 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, LLC

    961 Cedar Ln, Oakland, MD 21550
  • /24

    $85,000

    Sold Oct 03, 2025

    1101 Wheeling Ave, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,718 Sq Ft
    • Built 1950

    Last Sold Summary

    • $49/SF
    • 25 Days On Market

    Current Estimated Value $157,992

    Last Listing Agent Tanavia Greer Long & Foster Real Estate, Inc.

    1101 Wheeling Ave, Oakland, MD 21550
    • /130

      Est $1,088,960

      Not Listed For Sale

      943 S Blakeslee Rd, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 3,426 Sq Ft
      • Built 1990
      943 S Blakeslee Rd, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /47

    $559,000

    $30K PRICE DROP Under Contract
    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550

    Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lake has to offer, Whispering Pines is the ultimate turnkey mountain retreat. This impeccably maintained 5-bedroom townhome spans three levels of inviting living space and features an attached garage—perfect for hosting family, friends, or guests year-round. Enjoy the best of both worlds: a private, serene

    Nina Beitzel Railey Realty, Inc.

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
  • /24

    $110,000

    Sold Sep 26, 2025

    110 W Pennington St, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1946

    Last Sold Summary

    • $143/SF
    • 12 Days On Market

    Current Estimated Value $120,931

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

    110 W Pennington St, Oakland, MD 21550
    • /88

      Est $376,885

      Not Listed For Sale

      223 N 2nd St, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 3,120 Sq Ft
      • Built 1920
      223 N 2nd St, Oakland, MD 21550

      Last Sold Summary

      • 109 Days On Market

      Last Listing Agent Sean Sober Taylor-Made Deep Creek Real Estate, LLC

  • /12

    $45,000

    • Land
    • 14,810 Sq Ft
    • $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
  • /50

    $425,000

    Sold Jun 03, 2026

    609 Southern Pines Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,250 Sq Ft
    • Built 1989

    Last Sold Summary

    • 8% Below List Price
    • $189/SF
    • 295 Days On Market

    Current Estimated Value $414,783

    Last Listing Agent Brian Covell BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    609 Southern Pines Dr, Oakland, MD 21550
    • /29

      Not Listed For Sale

      22 Black Oak Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1998
      22 Black Oak Dr, Oakland, MD 21550

      Last Sold Summary

      • 16 Days On Market

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

  • /55

    $359,000

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 3 Baths
    • 2,388 Sq Ft

    215 H St, Oakland, MD 21550

    Welcome to the Maggie Watson Cottage, where historic charm meets modern convenience in the heart of Mountain Lake Park. This beautifully renovated home offers 3 bedrooms and 3 full bathrooms, thoughtfully updated to provide today’s comforts while preserving its timeless character. The interior features updated paint, both refinished and brand new hardwood flooring, and a modern gourmet kitchen

    Rachel Bruch Railey Realty, Inc.

    215 H St, Oakland, MD 21550
  • /22

    $185,000

    Sold May 22, 2026

    1307 Broadford Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • Built 2005

    Last Sold Summary

    • 11% Below List Price
    • $195/SF
    • 46 Days On Market

    Current Estimated Value $190,466

    Last Listing Agent Bill Kenny Keller Williams Realty Centre

    1307 Broadford Rd, Oakland, MD 21550

Showing Results 401 - 440, Page 11 of 18

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