12,296

Homes in ZIP Code 21550

Section Image
    • /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

  • /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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /13

    $119,900

    • Land
    • 33,976 Sq Ft
    • $153,718 per Acre

    120 Sundance Way, McHenry, MD 21541

    Level wooded building lot with scenic mountain views! This .78-acre homesite is centrally located minutes from Wisp Resort, Deep Creek Lake, Lodestone Golf Course, local restaurants, and nearby state parks, all while tucked away in a private mountaintop community. Ready to build with public water and sewer hookups to site. A straightforward opportunity to build your mountain dream home right in

    Mike Fenton Railey Realty, Inc.

    120 Sundance Way, McHenry, MD 21541
  • /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
    • /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

  • /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
  • /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
    • /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

  • /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
  • /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 $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

  • /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
  • /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
    • /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

  • /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
  • /67

    $790,000

    Sold Apr 24, 2026

    116 Chimney Rock Ln, McHenry, MD 21541

    • 5 Beds
    • 4.5 Baths
    • 2,964 Sq Ft
    • Built 2025

    Last Sold Summary

    • $267/SF
    • 246 Days On Market

    Current Estimated Value $789,875

    Last Listing Agent Jon Bell Railey Realty, Inc.

    116 Chimney Rock Ln, McHenry, MD 21541
    • /46

      Est $2,104,859

      Not Listed For Sale

      1425 Sandy Shores Rd, Mc Henry, MD 21541

      • 5 Beds
      • 5.5 Baths
      • 4,644 Sq Ft
      • Built 1998
      1425 Sandy Shores Rd, Mc Henry, MD 21541

      Last Sold Summary

      • 33 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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /9

    $77,900

    • Land
    • 23,086 Sq Ft
    • $146,981 per Acre

    42 Sandstone Cir, Sang Run, MD 21541

    Discover an exceptional opportunity at Lot 42 Sandstone Circle in the prestigious Lodestone community. Level, wooded homesite positioned just steps from the renowned Lodestone Championship Golf Course, offering both privacy and refined mountain living.The approved half-acre parcel is fully prepared for your custom residence, with public utilities available at the lot line. Nestled in the

    Rich Orr Railey Realty, Inc.

    42 Sandstone Cir, Sang Run, MD 21541
  • /42

    $545,000

    Sold Sep 22, 2025

    793 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,564 Sq Ft
    • Built 1995

    Last Sold Summary

    • $348/SF
    • 23 Days On Market

    Current Estimated Value $569,537

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    793 Mountainview Dr, 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

  • /29

    $75,000

    $15K PRICE DROP
    • Land
    • 26,136 Sq Ft
    • $125,000 per Acre

    40 Fern Loop, Sang Run, MD 21541

    Escape to the mountains and relax on your own piece of paradise on "Fern Loop". Build your dream home on this beautiful wooded homesite-"Lot 40" in the peaceful community of Sandy Shores Heights. On the mountaintop with easy access to the Lodestone Golf Course and a convenient hop to Deep Creek Lake, Fork Run, Yough River & Wisp Ski Resort. Utilities to site with public water & sewer hookups

    Kathy Gibson Railey Realty, Inc.

    40 Fern Loop, Sang Run, MD 21541
  • /13

    $62,000

    Sold Aug 01, 2025

    500 Seneca Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,284 Sq Ft
    • Built 1940

    Last Sold Summary

    • $48/SF
    • 577 Days On Market

    Current Estimated Value $105,288

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    500 Seneca Ave, 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

  • /56

    $1,285,000

    $10K PRICE DROP
    • 5 Beds
    • 6 Baths
    • 4,137 Sq Ft

    206 Highline Dr, Mc Henry, MD 21541

    Experience mountain living at its finest in this stunning 5-bedroom, 6-bath retreat nestled directly on the slopes of Wisp Resort with breathtaking views of Deep Creek Lake. Designed for those who love skiing, nature, and luxury mountain escapes, this exceptional home offers over 4,000 square feet of beautifully designed living space. The open-concept layout is filled with natural light, creating

    Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

    206 Highline Dr, Mc Henry, MD 21541
  • /48

    $250,000

    Sold Mar 27, 2026

    702 Sunshine Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 2009

    Last Sold Summary

    • 9% Below List Price
    • $135/SF
    • 16 Days On Market

    Current Estimated Value $257,103

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

    702 Sunshine Dr, 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

  • /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
  • /21

    $5,500

    Sold Mar 05, 2026

    5.5 Acres Lake Ford Rd, Mount Lake Park, MD 21550

    • Land
    • 5.5 Acres
    • $1,000 per Acre

    Last Sold Summary

    • 89% Below List Price
    • 126 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    5.5 Acres Lake Ford Rd, Mount Lake Park, 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

Showing Results 201 - 240, Page 6 of 18

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