10,549

Oakland, MD Homes

Section Image
    • /54

      Est $2,499,977

      Not Listed For Sale

      375 Glendale Rd, Oakland, MD 21550

      • 8 Beds
      • 6.5 Baths
      • 5,638 Sq Ft
      • Built 2001
      375 Glendale Rd, Oakland, MD 21550

      Last Sold Summary

      • 134 Days On Market

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • /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
  • /48

    $229,000

    Sold Dec 15, 2025

    104 G St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft
    • Built 1900

    Last Sold Summary

    • $142/SF
    • 26 Days On Market

    Current Estimated Value $230,979

    Last Listing Agent Julie Mead The KW Collective

    104 G St, Oakland, MD 21550
    • /18

      Est $223,694

      Not Listed For Sale

      9 Laurel Brook Dr, Oakland, MD 21550

      • 2 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1989
      9 Laurel Brook Dr, Oakland, MD 21550

      Last Sold Summary

      • 13 Days On Market

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

  • /8

    $17,000

    Pending
    • Land
    • 33,541 Sq Ft
    • $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 Real Estate, LLC

    Lot 40 W Big Piney Dr, Oakland, MD 21550
  • /22

    $38,000

    Sold Jun 16, 2026

    422 Maple Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,600 Sq Ft
    • Built 1940

    Last Sold Summary

    • 37% Below List Price
    • $24/SF
    • 34 Days On Market

    Current Estimated Value $56,774

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    422 Maple Ave, Oakland, MD 21550
    • /55

      Est $762,057

      Not Listed For Sale

      1557 Mountainview Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,590 Sq Ft
      • Built 1992
      1557 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 163 Days On Market

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

  • /64

    $769,900

    $30K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,780 Sq Ft

    467 Paradise Ridge Rd, Oakland, MD 21550

    Panoramic mountain and lake views set the tone at this lake access home in Paradise Ridge, one of Deep Creek’s most sought-after communities! Perched at the top of the hill on 1.29 acres, this 4-bedroom, 3 full and 1 half bath retreat offers 3,780 finished square feet across three levels. Abundant glass frames the surrounding ridgelines with views of Deep Creek Lake from every room in the house!

    Jon Bell Railey Realty, Inc.

    467 Paradise Ridge Rd, Oakland, MD 21550
  • /20

    $195,000

    Sold Nov 12, 2025

    210 Seneca Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,204 Sq Ft
    • Built 1996

    Last Sold Summary

    • $162/SF
    • 2 Days On Market

    Current Estimated Value $202,503

    Last Listing Agent Andrew Orr The KW Collective

    210 Seneca Ave, Oakland, MD 21550
    • /91

      Est $320,740

      Not Listed For Sale

      106 H St, Oakland, MD 21550

      • 7 Beds
      • 3 Baths
      • 2,934 Sq Ft
      • Built 1900
      106 H St, Oakland, MD 21550

      Last Sold Summary

      • 1,050 Days On Market

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

  • /113

    $715,000

    • 4 Beds
    • 5 Baths
    • 3,240 Sq Ft

    250 Lehman Ln Unit 39, Oakland, MD 21550

    Immaculate 4-bedroom log home in the highly sought after Gallatin Woods community. Custom built with custom finishes throughout. Granite counters, hardwood floors, 2 fireplaces, extensive hardscaped patio and outdoor fireplace, and the list of upgrades literally goes on and is available on request for the discerning buyer. Minutes from Deep Creek Lake and all of the area amenities yet tucked away

    Richard Candy Synergy Realty

    250 Lehman Ln Unit 39, Oakland, MD 21550
  • /71

    $950,000

    Sold Jul 29, 2026

    137 Paradise Gardens Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,730 Sq Ft
    • Built 1979

    Last Sold Summary

    • 9% Below List Price
    • $348/SF
    • 76 Days On Market

    Current Estimated Value $1,006,592

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

    137 Paradise Gardens Rd, Oakland, MD 21550
    • /65

      Est $252,771

      Not Listed For Sale

      6663 Gorman Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,982 Sq Ft
      • Built 1978
      6663 Gorman Rd, Oakland, MD 21550

      Last Sold Summary

      • 113 Days On Market

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /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
  • /33

    $130,000

    Sold May 22, 2026

    565 Glendale Rd Unit 210-A, Oakland, MD 21550

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

    Last Sold Summary

    • 26% Below List Price
    • $340/SF
    • 225 Days On Market

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

    565 Glendale Rd Unit 210-A, Oakland, MD 21550
    • /83

      Est $347,595

      Not Listed For Sale

      10 Sunset Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,167 Sq Ft
      • Built 1979
      10 Sunset Dr, Oakland, MD 21550

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Thomas Long Railey Realty, Inc.

  • /53

    $269,500

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    315 Coolidge Ave, Oakland, MD 21550

    Well maintained brick rancher located in the heart of Oakland. This home offers a large kitchen open to the living room with a built-in fireplace, separate dining room, and new carpet through out. The basement is very clean, offering a clean slate for whatever you would like to do. The rear covered porch, deck and fenced in yard makes a great space to enjoy family and friends. The location is

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

    315 Coolidge Ave, Oakland, MD 21550
  • /22

    $180,000

    Sold Sep 12, 2025

    4643 Oakland Sang Run Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 1979

    Last Sold Summary

    • $208/SF
    • 4 Days On Market

    Current Estimated Value $207,625

    Last Listing Agent Jon Bell Railey Realty, Inc.

    4643 Oakland Sang Run Rd, Oakland, MD 21550
    • /32

      Est $226,704

      Not Listed For Sale

      601 E Oak St, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 1,744 Sq Ft
      • Built 1922
      601 E Oak St, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

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

  • /38

    $629,000

    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft

    231 Santa fe Trail, Oakland, MD 21550

    Brand new roof July 2026! 3/4BR 3BA chalet with LAKE VIEWS! 2300sf vacation home fronting on a mountain stream, overlooking Deep Creek Lake! Enjoy an eat-in kitchen, exposed beams and a loft area that the current owners use as a 4th BR with bathroom. NO HOA! Conveys fully furnished. Features include central AC, exposed beams, updated flooring, gas fireplace on main level, lower level rec room

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    231 Santa fe Trail, Oakland, MD 21550
  • /45

    $750,000

    Sold Jan 16, 2026

    198 Grandview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,744 Sq Ft
    • Built 2003

    Last Sold Summary

    • $273/SF
    • 150 Days On Market

    Current Estimated Value $804,608

    Last Listing Agent Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, MD 21550
    • /78

      Est $310,136

      Not Listed For Sale

      3416 Wilson Corona Rd, Oakland, MD 21550

      • 4 Beds
      • 1.5 Baths
      • 1,936 Sq Ft
      • Built 1973
      3416 Wilson Corona Rd, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kevin Liller Railey Realty, Inc.

  • /64

    $275,900

    • 4 Beds
    • 2 Baths
    • 1,928 Sq Ft

    449 S 3rd St, Oakland, MD 21550

    Welcome to this beautifully updated 1901 home in the heart of downtown Oakland, where historic character meets modern convenience. Situated on a charming lot with mature landscaping and blooming trees, this home offers timeless curb appeal with a welcoming covered front porch perfect for relaxing and enjoying the neighborhood. Inside, you’ll find modern updates throughout while preserving classic

    Justin Liller Railey Realty, Inc.

    449 S 3rd St, Oakland, MD 21550
  • /48

    $250,000

    Sold Jun 11, 2026

    18 Ollie North Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,956 Sq Ft
    • Built 1975

    Last Sold Summary

    • 13% Below List Price
    • $128/SF
    • 31 Days On Market

    Current Estimated Value $252,420

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    18 Ollie North Rd, Oakland, MD 21550
    • /47

      Est $520,918

      Not Listed For Sale

      38 Traders Ln, Oakland, MD 21550

      • 4 Beds
      • 4.5 Baths
      • 2,582 Sq Ft
      • Built 2003
      38 Traders Ln, Oakland, MD 21550

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Taylor Kiggins Coldwell Banker Home Town Realty

  • /18

    $2,000

    $2K PRICE DROP Under Contract
    • Land
    • 24,393 Sq Ft
    • $3,571 per Acre

    Lot 40 Fawn Dr, Oakland, MD 21550

    Lot 40 Fawn Drive is a 0.56-acre wooded, NON-BUILDABLE membership lot located in Youghiogheny Mountain Resort community in Oakland, MD. This lot's ownership offers full membership access to the community’s amenities, including over 50 miles of private roads and trails perfect for ATV riding, UTVs, dirt bikes, hiking, and outdoor recreation. Ideal for outdoor enthusiasts seeking a private escape

    Shannon McWilliams Taylor-Made Deep Creek Real Estate, LLC

    Lot 40 Fawn Dr, Oakland, MD 21550
  • /65

    $558,000

    Sold Nov 10, 2025

    72 Cliff Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft
    • Built 1988

    Last Sold Summary

    • $256/SF
    • 32 Days On Market

    Current Estimated Value $579,048

    Last Listing Agent Larry Smith Railey Realty, Inc.

    72 Cliff Dr, Oakland, MD 21550
    • /82

      Est $2,524,105

      Not Listed For Sale

      1983 Lake Shore Dr, Oakland, MD 21550

      • 5 Beds
      • 6.5 Baths
      • 4,074 Sq Ft
      • Built 2000
      1983 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 236 Days On Market

      Last Listing Agent Randy Ritchie Taylor-Made Deep Creek Real Estate, LLC

  • /99

    $799,000

    • 5 Beds
    • 4 Baths
    • 3,480 Sq Ft

    18 Mountainside Ct, Oakland, MD 21550

    Welcome to your mountain retreat in the highly sought-after Mountainside community at Deep Creek Lake! This spacious 5-bedroom, 4-bath cedar-sided chalet blends classic mountain charm with the perfect layout for unforgettable lake getaways, family vacations, or a proven investment opportunity. Step inside to soaring walls of glass that frame filtered seasonal views of Deep Creek Lake, filling the

    Justin Liller Railey Realty, Inc.

    18 Mountainside Ct, Oakland, MD 21550
  • /6

    $30,000

    Sold Oct 23, 2025

    28 Wild Turkey Ln, Oakland, MD 21550

    • Land
    • 1 Acre
    • $30,000 per Acre

    Last Sold Summary

    • 14 Days On Market

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

    28 Wild Turkey Ln, Oakland, MD 21550
    • /76

      Est $944,964

      Not Listed For Sale

      1865 Paradise Point Rd, Oakland, MD 21550

      • 6 Beds
      • 3.5 Baths
      • 2,158 Sq Ft
      • Built 2005
      1865 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Randy Ritchie Taylor-Made Deep Creek Real Estate, LLC

  • /5

    $90,000

    $110K PRICE DROP
    • Land
    • 5 Acres
    • $18,000 per Acre

    3500 Area Maryland Hwy, Oakland, MD 21550

    The parcel is being sold by an estate. Wooded vacant land located at the 3400 area of Maryland Highway, Route 135. There is no record of Perc test on file at the Garrett County Health Department.

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    3500 Area Maryland Hwy, Oakland, MD 21550
  • /62

    $349,900

    Sold May 08, 2026

    16 Lemley Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 1,104 Sq Ft
    • Built 1974

    Last Sold Summary

    • $317/SF
    • 128 Days On Market

    Current Estimated Value $346,538

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    16 Lemley Dr, Oakland, MD 21550
    • /39

      Est $202,113

      Not Listed For Sale

      227 W Liberty St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,232 Sq Ft
      • Built 1910
      227 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 44 Days On Market

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

  • /62

    $775,000

    • 5 Beds
    • 4.5 Baths
    • 4,284 Sq Ft

    251 Robinwood Dr, Oakland, MD 21550

    One-of-a-kind Youghiogheny riverfront estate offering 224 feet of water frontage . Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to ceiling fireplace, log accent

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    251 Robinwood Dr, Oakland, MD 21550
  • /34

    $275,000

    Sold Jan 02, 2026

    34 Laurel Brook Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1992

    Last Sold Summary

    • 13 Days On Market

    Current Estimated Value $308,756

    Last Listing Agent Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    34 Laurel Brook Dr, Oakland, MD 21550
    • /61

      Est $805,710

      Not Listed For Sale

      889 Paradise Ridge Rd, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 3,004 Sq Ft
      • Built 2004
      889 Paradise Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • /13

    $34,900

    Pending
    • 3 Beds
    • 1 Bath
    • 1,920 Sq Ft

    3482 Oakland Sang Run Rd, Oakland, MD 21550

    Situated in a prime location just minutes from Wisp Resort and Deep Creek Lake. The value here is in the land and location. With nearly one acre, the property offers strong potential to build a custom home or vacation retreat in a highly desirable area. This home is in very poor condition. Do not enter the home or step onto the front porch, as both are unsafe. This property is ready for a buyer

    Casey Oleynikov Pearson Smith Realty, LLC

    3482 Oakland Sang Run Rd, Oakland, MD 21550
  • /48

    $205,000

    Sold Mar 20, 2026

    565 Glendale Rd Unit 312, Oakland, MD 21550

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

    Last Sold Summary

    • 10% Below List Price
    • $261/SF
    • 6 Days On Market

    Current Estimated Value $252,949

    Last Listing Agent Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 312, Oakland, MD 21550
    • /84

      Est $309,660

      Not Listed For Sale

      255 Foster Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,272 Sq Ft
      • Built 1962
      255 Foster Rd, Oakland, MD 21550

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Susan Bell Railey Realty, Inc.

Showing Results 441 - 480, Page 12 of 18

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