12,296

Homes in ZIP Code 21550

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  • /74

    $915,000

    Sold Sep 15, 2025

    186 Thornberry Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,347 Sq Ft
    • Built 1992

    Last Sold Summary

    • $390/SF
    • 48 Days On Market

    Current Estimated Value $984,230

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

    186 Thornberry Rd, Oakland, MD 21550
    • /48

      Est $308,261

      Not Listed For Sale

      314 Allegheny Dr, Oakland, MD 21550

      • 3 Beds
      • 3.5 Baths
      • 1,750 Sq Ft
      • Built 2007
      314 Allegheny Dr, Oakland, MD 21550

      Last Sold Summary

      • 9 Days On Market

  • /64

    $400,000

    • 2 Beds
    • 1 Bath
    • 1,800 Sq Ft

    2967 Pysell Crosscut Rd, Oakland, MD 21550

    Discover the charm and comfort of this beautifully maintained manufactured home, nestled on a generous 2.07-acre lot. With a unique blend of rustic appeal and modern convenience, this property is perfect for those seeking a serene retreat without sacrificing accessibility. Step inside to find a warm and inviting interior with carpeting and laminate flooring that flows seamlessly throughout. The

    Larry Smith Railey Realty, Inc.

    2967 Pysell Crosscut Rd, Oakland, MD 21550
  • /30

    $200,000

    Sold Oct 09, 2025

    929 Dogwood Dr, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1973

    Last Sold Summary

    • $174/SF
    • 15 Days On Market

    Current Estimated Value $211,827

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

    929 Dogwood Dr, Oakland, MD 21550
    • /87

      Est $448,844

      Not Listed For Sale

      2702 Mayhew Inn Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1982
      2702 Mayhew Inn Rd, Oakland, MD 21550

      Last Sold Summary

      • 9 Days On Market

  • /2

    $134,000

    • Land
    • 1 Acre
    • $134,000 per Acre

    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550

    Wooded lot with spectacular views of Paradise Point area of lake. Great privacy. Sewer tap available

    John Zorzit Eagle Commercial Realty

    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
  • /110

    $1,900,000

    Under Contract
    • 5 Beds
    • 3.5 Baths
    • 4,619 Sq Ft

    815 Chadderton School Rd, Oakland, MD 21550

    Experience lakefront living at its finest in this exceptional 5-bedroom, 3.5-bath home offering over 4,600 square feet of living space on a private lot of more than one acre. Featuring an incredibly spacious primary suite on the main level, as well as an additional master suite on the second level, this home is ideal for both full-time living and hosting guests. Enjoy breathtaking lake views from

    Kevin Liller Railey Realty, Inc.

    815 Chadderton School Rd, Oakland, MD 21550
    • /42

      Est $169,914

      Not Listed For Sale

      112 B St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1972
      112 B St, Oakland, MD 21550

      Last Sold Summary

      • 23 Days On Market

  • /19

    $89,900

    • Land
    • 1 Acre
    • $89,900 per Acre

    36 Fern Loop, Sang Run, MD 21541

    1.00 acre building lot in Sandy Shores Heights at Wisp Mountain Resort. Centrally located just minutes from Local Restaurants, State Parks, Wisp Resort and Deep Creek Lake! Public utilities to site. Strong location & ready for your plans!

    Jon Bell Railey Realty, Inc.

    36 Fern Loop, Sang Run, MD 21541
  • /15

    $82,500

    Sold Jun 20, 2025

    Lot 112 Biltmore View, Mc Henry, MD 21541

    • Land
    • 27,878 Sq Ft
    • $128,906 per Acre

    Last Sold Summary

    • 33% Below List Price
    • 751 Days On Market

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

    Lot 112 Biltmore View, Mc Henry, MD 21541
    • /64

      Est $177,887

      Not Listed For Sale

      608 I St, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,674 Sq Ft
      • Built 1900
      608 I St, Oakland, MD 21550

      Last Sold Summary

      • 83 Days On Market

  • /8

    $24,900

    • Land
    • 13,503 Sq Ft
    • $80,323 per Acre

    460 W Liberty St, Oakland, MD 21550

    Lot within the town limits of Oakland with water and sewer hookups. This lot had a mobile home that was taken off. According to the owner, both Garrett County Planning and Zoning and the Town of Oakland have indicated that another mobile home can be placed on the lot but it has to be a NEW mobile home. According to P & Z, it must be a new mobile home and will have to be elevated 2' (three blocks)

    Kevin Liller Railey Realty, Inc.

    460 W Liberty St, Oakland, MD 21550
  • /70

    $465,000

    Sold Aug 12, 2025

    612 Harvey Winters Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,473 Sq Ft
    • Built 2010

    Last Sold Summary

    • $188/SF
    • 6 Days On Market

    Current Estimated Value $465,328

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    612 Harvey Winters Dr, Oakland, MD 21550
    • /42

      Est $224,054

      Not Listed For Sale

      19 A St, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,920 Sq Ft
      • Built 1973
      19 A St, Oakland, MD 21550

      Last Sold Summary

      • 152 Days On Market

  • /10

    $375,000

    • 5 Beds
    • 1.5 Baths
    • 1,536 Sq Ft

    511 Main St, Oakland, MD 21550

    The property offered for sale is 32.20 acres located on the southwest & northwest corners of Maryland Highway, State Route 135 at Main Street & Sand Flat Road, Deer Park. The Single Family Residence built in 1920 has 5 bedrooms, 1 full bathroom and 1 half bathroom. The residence is being sold "As Is". The residence is prime for renovation; the parcel may have commercial potential. The current

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    511 Main St, Oakland, MD 21550
  • /31

    $745,000

    Sold Sep 02, 2025

    200 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,559 Sq Ft
    • Built 2025

    Last Sold Summary

    • $291/SF
    • 16 Days On Market

    Current Estimated Value $752,441

    Last Listing Agent Jonathan Minerick Homecoin.com

    200 Lake Shore Dr, Oakland, MD 21550
    • /74

      Est $699,347

      Not Listed For Sale

      14 Wanderer Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,355 Sq Ft
      • Built 1973
      14 Wanderer Ln, Oakland, MD 21550

      Last Sold Summary

      • 1 Day On Market

  • /6

    $4,000

    • Land
    • 20,037 Sq Ft
    • $8,696 per Acre

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550

    Here is an affordable chance to own a lot and have access to all of Youghiogheny Mountain Resort's beautiful and fun amenities!

    Jonathan Price Railey Realty, Inc.

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550
  • /9

    $25,000

    Sold Jan 14, 2026

    18 Hoye Crest Rd, Oakland, MD 21550

    • Land
    • 7.51 Acres
    • $3,329 per Acre

    Last Sold Summary

    • 63 Days On Market

    Last Listing Agent Kellyann Green Railey Realty, Inc.

    18 Hoye Crest Rd, Oakland, MD 21550
    • /62

      Est $326,932

      Not Listed For Sale

      103 Overlook Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,640 Sq Ft
      • Built 1985
      103 Overlook Dr, Oakland, MD 21550

      Last Sold Summary

      • 63 Days On Market

  • /28

    $185,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft

    512 Roanoke Ave, Oakland, MD 21550

    The first thing you will notice as you approach 512 Roanoke Ave in loch Lynn heights is the towering maple trees lining the street. (In early spring they provide syrup for a lucky few!) Framing this post-card perfect snap shot is a park on either side. The Loch Lynn Wetlands Trail is the beating heart of the neighborhood, and the Loch Lynn Community Park and Pavillion hosts the annual town

    Brady Harden Coldwell Banker Premier

    512 Roanoke Ave, Oakland, MD 21550
  • /68

    $1,060,000

    Sold Apr 10, 2026

    444 Woodlands Hill Ln, Oakland, MD 21550

    • 4 Beds
    • 6 Baths
    • 4,744 Sq Ft
    • Built 2007

    Last Sold Summary

    • 12% Below List Price
    • $223/SF
    • 50 Days On Market

    Current Estimated Value $1,081,707

    Last Listing Agent Corbin Griffith Compass

    444 Woodlands Hill Ln, Oakland, MD 21550
    • /38

      Est $286,478

      Not Listed For Sale

      644 Silver Knob Rd, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,728 Sq Ft
      • Built 1967
      644 Silver Knob Rd, Oakland, MD 21550

      Last Sold Summary

      • 9 Days On Market

  • /24

    $16,000

    • Land
    • 21,344 Sq Ft
    • $32,653 per Acre

    21 Bear Dr E, Oakland, MD 21550

    Don’t miss this great opportunity in the gated community of Youghiogheny Mountain Resort! This flat 0.49-acre lot offers an easy build site. Perfect for your dream home or weekend escape. Enjoy access to ATV trails, hunting, and fishing, all while being just a short drive to Wisp Resort, Deep Creek Lake, and Swallow Falls State Park. Approved for a sand mound septic system and set within a

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    21 Bear Dr E, Oakland, MD 21550
  • /8

    $99,000

    Sold Jan 30, 2026

    125 N 2nd St, Oakland, MD 21550

    • Land
    • 9,583 Sq Ft
    • $450,000 per Acre

    Last Sold Summary

    • 38 Days On Market

    Current Estimated Value $99,070

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    125 N 2nd St, Oakland, MD 21550
    • /57

      Est $332,215

      Not Listed For Sale

      840 Smouse Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,863 Sq Ft
      • Built 1980
      840 Smouse Rd, Oakland, MD 21550

      Last Sold Summary

      • 17 Days On Market

  • /7

    $24,900

    $5K PRICE DROP
    • Land
    • 4 Acres
    • $6,225 per Acre

    Lot 7 Backbone Ridge Rd, Oakland, MD 21550

    This 4-acre building lot in the Backbone Ridge community offers breathtaking mountain views and a 3-bedroom perc approval — ready for your dream home. Perfectly positioned near Deep Creek Lake, WISP Ski Resort, Canaan Valley, Timberline Ski Resort, and Blackwater Falls State Park, outdoor adventure is just minutes away. Whether you're building a year-round residence or a weekend escape, enjoy the

    Brent Housley Railey Realty, Inc.

    Lot 7 Backbone Ridge Rd, Oakland, MD 21550
  • /114

    $1,000,000

    Sold Feb 05, 2026

    1720 Pysell Crosscut Rd, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 8,000 Sq Ft
    • Built 1976

    Last Sold Summary

    • $125/SF
    • 52 Days On Market

    Current Estimated Value $540,710

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

    1720 Pysell Crosscut Rd, Oakland, MD 21550
    • /30

      Est $362,442

      Not Listed For Sale

      968 Paradise Heights, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,080 Sq Ft
      • Built 1993
      968 Paradise Heights, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /11

    $49,900

    • Land
    • 1.38 Acres
    • $36,159 per Acre

    LOT 6B Betts Ln, Oakland, MD 21550

    This 1.38-acre property offers a private, quiet setting with level ground and easy access from a well maintained road. Located just a short drive from Deep Creek Lake and Oakland, MD, it gives you the feel of being in the country while still being close to town. The lot is surrounded by woods and is a great spot to enjoy nature, with plenty of wildlife in the area. A solid option for a future

    Thomas Long Railey Realty, Inc.

    LOT 6B Betts Ln, Oakland, MD 21550
  • /6

    $57,500

    Sold Aug 27, 2025

    3 Edens Ridge Rd, Oakland, MD 21550

    • Land
    • 5 Acres
    • $11,500 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    3 Edens Ridge Rd, Oakland, MD 21550
    • /105

      Est $391,833

      Not Listed For Sale

      1265 Bray School Rd, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 1983
      1265 Bray School Rd, Oakland, MD 21550

      Last Sold Summary

      • 66 Days On Market

  • /50

    $325,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,016 Sq Ft

    29 Woodmont Ln, Oakland, MD 21550

    Immaculate 4-bedroom/3-bath countryside home less than 10 minutes from Oakland. This property has been exceptionally well-maintained — truly move-in ready and prepared for you to make your own memories. A private in-ground pool awaits you out back - perfect for summer entertaining. Enjoy the western exposure and stunning sunsets from your elevated deck. A .86 acre lot provides a great yard and

    Brent Housley Railey Realty, Inc.

    29 Woodmont Ln, Oakland, MD 21550
  • /64

    $385,000

    Sold Jun 03, 2026

    1204 Alexander Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,266 Sq Ft
    • Built 1989

    Last Sold Summary

    • 4% Below List Price
    • $170/SF
    • 4 Days On Market

    Current Estimated Value $394,763

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1204 Alexander Ln, Oakland, MD 21550
    • /95

      Est $1,524,141

      Not Listed For Sale

      478 Lake Forest Dr, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 2,688 Sq Ft
      • Built 1996
      478 Lake Forest Dr, Oakland, MD 21550

      Last Sold Summary

      • 48 Days On Market

  • /26

    $425,000

    • Land
    • 1.34 Acres
    • $317,164 per Acre

    LOT 25 Holy Cross Dr, Oakland, MD 21550

    Discover the perfect blend of privacy, prestige, and natural beauty with Lot 25 in The Reserve at Holy Cross—a premier wooded lakefront homesite tucked into a serene private cove on Deep Creek Lake. Boasting 1.34 acres and an impressive 251 feet of lake frontage, this exceptional lot offers the ideal setting to build your dream retreat. Enjoy direct access to the water with up to two boat slips

    Nina Beitzel Railey Realty, Inc.

    LOT 25 Holy Cross Dr, Oakland, MD 21550
  • /39

    $405,000

    Sold Jun 15, 2026

    232 Jeffrey Ln Unit 33, Oakland, MD 21550

    • 2 Beds
    • 2.5 Baths
    • 2,960 Sq Ft
    • Built 2002

    Last Sold Summary

    • 5% Below List Price
    • $137/SF
    • 99 Days On Market

    Current Estimated Value $419,874

    Last Listing Agent Sean Brink Samson Properties

    232 Jeffrey Ln Unit 33, Oakland, MD 21550
    • /75

      Est $1,674,865

      Not Listed For Sale

      771 Marsh Hill Rd, Mc Henry, MD 21541

      • 6 Beds
      • 5.5 Baths
      • 3,860 Sq Ft
      • Built 2021
      771 Marsh Hill Rd, Mc Henry, MD 21541

      Last Sold Summary

      • 100 Days On Market

  • /78

    $1,579,900

    • 4 Beds
    • 3 Baths
    • 3,278 Sq Ft

    2311 Boy Scout Rd, Oakland, MD 21550

    Experience the best of Deep Creek Lake living from this private waterfront retreat tucked among mature trees on nearly an acre of land. With over 100 feet of lake frontage, a private Type-A dock, and a gentle distance to deep water, this property offers the kind of shoreline that's increasingly hard to find. Thoughtfully positioned to capture expansive lake views while preserving a sense of

    Jon Bell Railey Realty, Inc.

    2311 Boy Scout Rd, Oakland, MD 21550
  • /139

    $2,625,000

    Sold Mar 31, 2026

    56 Bee Tree Ln, Oakland, MD 21550

    • 6 Beds
    • 7.5 Baths
    • 5,100 Sq Ft
    • Built 2000

    Last Sold Summary

    • $515/SF
    • 305 Days On Market

    Current Estimated Value $2,641,772

    Last Listing Agent Susan Bell Railey Realty, Inc.

    56 Bee Tree Ln, Oakland, MD 21550

Showing Results 281 - 320, Page 8 of 18

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