10,771

Oakland, MD Homes

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  • /50

    $499,900

    $30K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,235 Sq Ft

    126 Leo Friend Rd, Oakland, MD 21550

    Perched above the treetops with panoramic lake views, this three-level retreat blends comfort with clean, considered upgrades. Vaulted ceilings and a spacious loft crown 2,235 square feet of living space, wrapped in new flooring with fresh paint inside and out. The kitchen, smartly updated with new countertops, connects to open dining and living anchored by a wood stove. A detached garage sits

    Jon Bell Railey Realty, Inc.

    126 Leo Friend Rd, Oakland, MD 21550
  • /65

    $375,000

    Sold Jul 29, 2025

    5154 Maryland Hwy, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 2,860 Sq Ft
    • Built 1980

    Last Sold Summary

    • $131/SF
    • 23 Days On Market

    Current Estimated Value $385,590

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    5154 Maryland Hwy, Oakland, MD 21550
    • /7

      Not Listed For Sale

      Lot 5 Bobcat Hill Ln, Oakland, MD 21550

      Lot 5 Bobcat Hill Ln, Oakland, MD 21550

      Last Sold Summary

      • 43 Days On Market

  • /30

    $169,000

    • Land
    • 9.75 Acres
    • $17,333 per Acre

    9.75 AC. Dennett Rd, Oakland, MD 21550

    9.75 acres of prime land in a highly convenient Oakland location! This versatile property offers outstanding potential for development or the ideal setting for a private estate-sized homesite. Seller has already completed a proposed subdivision engineering plan, providing added value and future possibilities. Public water and sewer taps available per Oakland Town Administrator. Gently rolling

    Nina Beitzel Railey Realty, Inc.

    9.75 AC. Dennett Rd, Oakland, MD 21550
  • /63

    $920,000

    Sold Aug 22, 2025

    254 Middleton Rd, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 2,400 Sq Ft
    • Built 1994

    Last Sold Summary

    • $383/SF
    • 19 Days On Market

    Current Estimated Value $919,012

    Last Listing Agent Jon Bell Railey Realty, Inc.

    254 Middleton Rd, Oakland, MD 21550
    • /7

      Not Listed For Sale

      25 Acres Lot D Bailiff Ln, Oakland, MD 21550

      25 Acres Lot D Bailiff Ln, Oakland, MD 21550

      Last Sold Summary

      • 20 Days On Market

  • /27

    $229,900

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 106B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs in a gas fireplace, full bath with tub/shower, and a tidy kitchenette with microwave, dishwasher, and full fridge. Balcony doors open to Deep Creek air and filtered lake scenes. Community perks include sauna, gym, game room and more. Sold turn-key, fully furnished. Ductless units for heat and A/C. Monthly

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 106B, Oakland, MD 21550
  • /33

    $150,000

    Sold Dec 17, 2025

    111 Knoll Crest Heights Dr, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 3,504 Sq Ft
    • Built 1971

    Last Sold Summary

    • $43/SF
    • 48 Days On Market

    Current Estimated Value $158,784

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    111 Knoll Crest Heights Dr, Oakland, MD 21550
    • /82

      Est $1,220,549

      Not Listed For Sale

      20476 Garrett Hwy, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 2,635 Sq Ft
      • Built 1998
      20476 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 53 Days On Market

  • /9

    $35,000

    • Land
    • 20,037 Sq Ft
    • $76,087 per Acre

    Lot 233 Cumberland Rd, Oakland, MD 21550

    Seize the opportunity to own a beautiful parcel of land just minutes from Deep Creek Lake—one of the region’s most sought-after destinations for recreation and relaxation. This nearly half-acre property offers the rare combination of no HOA and no restrictions, giving you the freedom to bring your vision to life without limitations. Whether you're dreaming of building a cozy getaway cabin, a

    Sheila Howell Lake Homes Realty, LLC

    Lot 233 Cumberland Rd, Oakland, MD 21550
  • /43

    $460,000

    Sold Oct 24, 2025

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,200 Sq Ft
    • Built 2009

    Last Sold Summary

    • $209/SF
    • 16 Days On Market

    Current Estimated Value $466,930

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    • /10

      Not Listed For Sale

      0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550

      0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550

      Last Sold Summary

  • /52

    $3,249,000

    New Construction
    • 4 Beds
    • 5 Baths
    • 6,036 Sq Ft

    415 Nazelrod Rd, Oakland, MD 21550

    One of Garrett County's most unique and breathtaking mountain estates, this completely custom masterpiece was designed and built with exceptional craftsmanship and attention to detail. The 6000 +/- sq ft custom newly built home is located in the beautiful mountains of Garrett County, Maryland and offers the new owner one-of-a-kind unobstructed panoramic views, serenity, privacy and endless

    Larry Smith Railey Realty, Inc.

    415 Nazelrod Rd, Oakland, MD 21550
  • /32

    $139,000

    Sold Aug 15, 2025

    4960 Hutton Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • Built 1971

    Last Sold Summary

    • $129/SF
    • 205 Days On Market

    Current Estimated Value $142,008

    Last Listing Agent Justin Liller Railey Realty, Inc.

    4960 Hutton Rd, Oakland, MD 21550
    • /10

      Not Listed For Sale

      TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550

      TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550

      Last Sold Summary

      • 42 Days On Market

  • /42

    $245,000

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft

    13 Laurel Brook Dr, Oakland, MD 21550

    Affordable well maintained 2 Bedroom 2 Bath townhouse style condominium less than 1 mile from Deep Creek Lake. Offering low maintenance and a pleasant setting, the property works well for full and part time ownership. The unit offers recent upgrades and Includes 2 parking spaces along with public water, sewer and weekly trash pickup. Shown by appointment only.

    Bill Weissgerber Railey Realty, Inc.

    13 Laurel Brook Dr, Oakland, MD 21550
  • /72

    $310,000

    Sold Jun 18, 2025

    202 Deerfield Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,720 Sq Ft
    • Built 1987

    Last Sold Summary

    • $114/SF
    • 128 Days On Market

    Current Estimated Value $325,054

    Last Listing Agent Sharon Murray Coldwell Banker Home Town Realty

    202 Deerfield Dr, Oakland, MD 21550
    • /37

      Not Listed For Sale

      278 Basswood Way Unit 19, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 3,084 Sq Ft
      • Built 2005
      278 Basswood Way Unit 19, Oakland, MD 21550

      Last Sold Summary

      • 87 Days On Market

  • /51

    $170,000

    Under Contract
    • 1 Bed
    • 1 Bath
    • 484 Sq Ft

    565 Glendale Rd Unit 208, Oakland, MD 21550

    Enjoy easy vacation living in this fully furnished one-bedroom suite at Silver Tree Suites. Ideally located on the second floor, this unit offers a private deck and convenient access to the library, sitting lounge, and lake-view common areas overlooking the grand lobby fireplaces. Owners and guests enjoy access to a fitness center, sauna, game room, laundry facilities, and meeting spaces. Silver

    Jesse Shimrock Railey Realty, Inc.

    565 Glendale Rd Unit 208, Oakland, MD 21550
  • /108

    $370,000

    Sold Oct 10, 2025

    220 N 11th St, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 3,159 Sq Ft
    • Built 1972

    Last Sold Summary

    • $117/SF
    • 12 Days On Market

    Current Estimated Value $368,828

    Last Listing Agent Justin Liller Railey Realty, Inc.

    220 N 11th St, Oakland, MD 21550
    • /47

      Est $297,328

      Not Listed For Sale

      33 Laurel Brook Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,120 Sq Ft
      • Built 1989
      33 Laurel Brook Dr, Oakland, MD 21550

      Last Sold Summary

      • 48 Days On Market

  • /13

    $63,000

    • 792 Sq Ft

    809 N St, Oakland, MD 21550

    Bring your vision and TLC to explore the possibilities here for rehab. Mt. Lake Park home being sold "As Is" Buyer to confirm with the county and the town of Mt. Lake Park for permits and building stipulations. Take a look & enjoy the ambiance of this historic area. RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. PROSPECTIVE PURCHASERS AND THEIR AGENTS ASSUME ALL LIABILITY

    Kathy Gibson Railey Realty, Inc.

    809 N St, Oakland, MD 21550
  • /45

    $435,000

    Sold Jul 02, 2025

    256 Jeffrey Ln Unit 28, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 1,838 Sq Ft
    • Built 2004

    Last Sold Summary

    • $237/SF
    • 626 Days On Market

    Current Estimated Value $427,925

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

    256 Jeffrey Ln Unit 28, Oakland, MD 21550
    • /64

      Est $1,649,791

      Not Listed For Sale

      1200 Mountainview Dr, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 5,926 Sq Ft
      • Built 1998
      1200 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 78 Days On Market

  • /11

    $19,500

    $6K PRICE DROP
    • Land
    • 5,227 Sq Ft
    • $162,500 per Acre

    Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550

    Fantastic bargain for this homesite! Gallatin Woods is a unique log home community located on Lakeshore Drive in the innermost part of Deep Creek Lake. Each owner may build within the building cylinder indicated on the plat and have exclusive use of the parking area and the additional land that immediately surrounds the home site. All other land within the community is condominiumized to keep the

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

    Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550
  • /37

    $199,000

    Sold Feb 25, 2026

    1108 Hutton Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1989

    Last Sold Summary

    • $207/SF
    • 3 Days On Market

    Current Estimated Value $200,580

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1108 Hutton Rd, Oakland, MD 21550
    • /6

      Not Listed For Sale

      223 Old Crellin Rd, Oakland, MD 21550

      • 1 Bed
      • 1 Bath
      • 980 Sq Ft
      • Built 1986
      223 Old Crellin Rd, Oakland, MD 21550

      Last Sold Summary

      • 67 Days On Market

  • /50

    $679,900

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    4A Mystic Creek Trail, Oakland, MD 21550

    Discover refined mountain-lake living in this new construction townhome at Mystic Creek on Deep Creek Lake. Designed with today’s lifestyle in mind, the home features a modern open-concept main level ideal for entertaining, with clean lines, abundant natural light, and seamless flow between living, dining, and kitchen spaces. This spacious residence offers three primary suites, each with upscale

    Justin Liller Railey Realty, Inc.

    4A Mystic Creek Trail, Oakland, MD 21550
  • /40

    $311,500

    Sold Aug 22, 2025

    181 Jeffrey Ln Unit 23D, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 800 Sq Ft
    • Built 1997

    Last Sold Summary

    • $389/SF
    • 167 Days On Market

    Current Estimated Value $301,117

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

    181 Jeffrey Ln Unit 23D, Oakland, MD 21550
    • /21

      Est $260,018

      Not Listed For Sale

      35 Weber Ct, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 2009
      35 Weber Ct, Oakland, MD 21550

      Last Sold Summary

      • 159 Days On Market

  • /61

    $969,000

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

    251 Robinwood Dr, Oakland, MD 21550

    One-of-a-kind Youghiogheny riverfront estate offering 400 feet of water frontage on 5+ acres and 2 separate lots. 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

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    251 Robinwood Dr, Oakland, MD 21550
  • /79

    $925,000

    Sold Oct 07, 2025

    1473 Pergin Farm Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,230 Sq Ft
    • Built 1945

    Last Sold Summary

    • $415/SF
    • 93 Days On Market

    Current Estimated Value $1,406,673

    Last Listing Agent Tony Migliaccio Long & Foster Real Estate, Inc.

    1473 Pergin Farm Rd, Oakland, MD 21550
    • /4

      Est $3,111,932

      Not Listed For Sale

      214 McComas Beach Terrace, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 6,890 Sq Ft
      • Built 2010
      214 McComas Beach Terrace, Oakland, MD 21550

      Last Sold Summary

  • /55

    $795,000

    • 5 Beds
    • 3.5 Baths
    • 4,230 Sq Ft

    312 Moss Creek Cir, Oakland, MD 21550

    Tucked away on a picturesque 1.83-acre parcel, this charming log home offers the perfect blend of rustic character and modern comfort. Amongst the 4,200+ SF, you will find five spacious bedrooms, two family rooms, a playroom, an office/den, a large loft, spacious pantry, granite counter tops, hardwood flooring and two fireplaces. The warm wood interior and classic log construction create a cozy,

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

    312 Moss Creek Cir, Oakland, MD 21550
  • /73

    $285,000

    Sold Oct 06, 2025

    122 Earl Hauser Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft
    • Built 2012

    Last Sold Summary

    • $171/SF
    • 3 Days On Market

    Current Estimated Value $281,815

    Last Listing Agent Rich Orr Railey Realty, Inc.

    122 Earl Hauser Rd, Oakland, MD 21550
    • /72

      Est $607,290

      Not Listed For Sale

      145 Ridgewood Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 3,838 Sq Ft
      • Built 1999
      145 Ridgewood Dr, Oakland, MD 21550

      Last Sold Summary

      • 1 Day On Market

  • /81

    $399,900

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft

    3930 Mayhew Inn Rd, Oakland, MD 21550

    2 for 1 on 2 .3 +/- acres! Remodeled 2BR 2BA cottage with auxiliary building that has an oversized garage, multiple workshop areas and 1BR 1BA apartment on the second level. New Maryland legislation, Accessory Dwelling Units Act of 2025, will allow expanded access to use the apartment above the garage in a more meaningful manner. Cabin boasts high end finishes and open living space with a cozy

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    3930 Mayhew Inn Rd, Oakland, MD 21550
  • /27

    $712,500

    Sold Dec 30, 2025

    939 Glendale Rd Unit 19, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • Built 1994

    Last Sold Summary

    • $498/SF
    • 91 Days On Market

    Last Listing Agent Rick Davis Richard A. Davis & Associates

    939 Glendale Rd Unit 19, 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

Showing Results 121 - 160, Page 4 of 18

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