12,296

Homes in ZIP Code 21550

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  • /37

    $120,000

    Sold Dec 04, 2025

    204 E St, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 2,084 Sq Ft
    • Built 1975

    Last Sold Summary

    • $58/SF
    • 1 Day On Market

    Current Estimated Value $122,290

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    204 E St, Oakland, MD 21550
    • /65

      Est $147,535

      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

  • /15

    $39,000

    • Land
    • 2.57 Acres
    • $15,175 per Acre

    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550

    2 lots (7 & 8) totaling 2.57 acres, on gently sloping wooded area. Nestled between Cannan Valley & Deep Creek Lake, this promises to be a perfect blend of convenience and tranquility. Nature surrounds you - the perfect spot for a cozy cabin! Call agent for more information!

    Julie Mead The KW Collective

    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
  • /64

    $1,010,000

    Sold Jan 09, 2026

    635 Biltmore Ridge Trail, Mc Henry, MD 21541

    • 5 Beds
    • 5 Baths
    • 4,437 Sq Ft
    • Built 2024

    Last Sold Summary

    • $228/SF
    • 91 Days On Market

    Current Estimated Value $1,040,379

    Last Listing Agent Edward Bass EXP Realty, LLC

    635 Biltmore Ridge Trail, Mc Henry, MD 21541
    • /76

      Est $202,077

      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

  • /23

    $38,500

    $6K PRICE DROP
    • Land
    • 25,700 Sq Ft
    • $65,254 per Acre

    LOT 13 Bray Run Rd, 14, West Oakland, MD 21550

    Build your dream home or vacation retreat on this beautiful 0.59 acre lot in Bray Run! Just a short drive to the Deep Creek Lake area, you’ll have easy access to boating, paddling, fishing, and state park facilities. This ready to build site is part of a peaceful mountain community offering excellent amenities. Enjoy a playground, basketball court, scenic hiking trails, and the beauty of Bray Run

    Nicole Jackson Railey Realty, Inc.

    LOT 13 Bray Run Rd, 14, West Oakland, MD 21550
  • /11

    $375,000

    Sold Apr 30, 2026

    2173 King Wildesen Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • Built 2025

    Last Sold Summary

    • 0 Days On Market

    Current Estimated Value $374,428

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

    2173 King Wildesen Rd, Oakland, MD 21550
    • /42

      Est $176,126

      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

  • /51

    $434,900

    • 4 Beds
    • 3 Baths
    • 2,406 Sq Ft

    511 Hilltop Rd, Oakland, MD 21550

    Tucked away on a quiet cul-de-sac in the desirable Royal Charlotte community, this stunning 4-bedroom, 3-bathroom home is the kind of property you'll fall in love with the moment you arrive. Surrounded by the beauty and tranquility of the mountains and accessed by county-maintained roads, this impeccably maintained home showcases pride of ownership throughout. From the expansive Trex decking that

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    511 Hilltop Rd, Oakland, MD 21550
  • /47

    $270,000

    Sold Jun 20, 2025

    403 O St, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,240 Sq Ft
    • Built 1976

    Last Sold Summary

    • $121/SF
    • 329 Days On Market

    Current Estimated Value $262,327

    Last Listing Agent ANGELA BOSLEY Taylor-Made Deep Creek Real Estate, LLC

    403 O St, Oakland, MD 21550
    • /6

      Est $646,205

      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

  • /7

    $36,000

    $10K PRICE INCREASE Pending
    • Land
    • 2 Acres
    • $18,000 per Acre

    0 Hutton Road(2 Acres), Oakland, MD 21550

    2 acres off Hutton Rd, raw land, endless possibilities. No restrictions, county zoning applies. Manly tree covered.

    Julie Mead The KW Collective

    0 Hutton Road(2 Acres), Oakland, MD 21550
  • /47

    $260,000

    Sold Feb 27, 2026

    20160 Garrett Hwy Unit H708, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft
    • Built 1972

    Last Sold Summary

    • $473/SF
    • 234 Days On Market

    Current Estimated Value $262,544

    Last Listing Agent Charlotte Savoy The KW Collective

    20160 Garrett Hwy Unit H708, Oakland, MD 21550
    • /80

      Est $716,531

      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

  • /5

    $18,000

    • Land
    • 27,007 Sq Ft
    • $29,032 per Acre

    13 Birchwood Dr, Oakland, MD 21550

    Discover your own mountain escape in the gated community of Youghiogheny Mountain Resort! This 0.62-acre lot is perfect for building a dream home or weekend retreat, surrounded by miles of ATV trails, hunting, and fishing. Ideally located near Wisp Resort, Deep Creek Lake, Herrington Manor State Park, and Swallow Falls State Park, you’ll enjoy year-round outdoor adventure. Approved for a sand

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    13 Birchwood Dr, Oakland, MD 21550
  • /107

    $1,350,000

    Sold Sep 19, 2025

    421 Penn Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 4,284 Sq Ft
    • Built 1986

    Last Sold Summary

    • $315/SF
    • 54 Days On Market

    Current Estimated Value $1,425,284

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    421 Penn Cove Rd, Oakland, MD 21550
    • /85

      Est $1,734,425

      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

  • /69

    $2,100,000

    • 5 Beds
    • 5 Baths
    • 4,074 Sq Ft

    1038 S Blakeslee Rd, Oakland, MD 21550

    Welcome to 1038 S Blakeslee Road! A spacious lakefront retreat on Deep Creek Lake offering effortless lakeside living. A Rare opportunity to own in one of Deep Creek’s most sought-after lakeside communities. This five-bedroom, five-bath home sits on a large 1.11-acre level lot with easy access to the water and generous outdoor space for recreation and entertaining. Inside, the home is warm and

    Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    1038 S Blakeslee Rd, Oakland, MD 21550
  • /61

    $820,000

    Sold Sep 02, 2025

    939 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1990

    Last Sold Summary

    • 18 Days On Market

    Current Estimated Value $822,708

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

    939 Glendale Rd, Oakland, MD 21550
    • /73

      Est $236,275

      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

  • /24

    $18,000

    • Land
    • 20,473 Sq Ft
    • $38,298 per Acre

    27 Gobbler Run Rd, Oakland, MD 21550

    Build your ideal mountain retreat in the gated community of Youghiogheny Mountain Resort! This level 0.47-acre lot offers an easy build site and is Health Department approved for a shallow trench gravity septic system. Enjoy access to ATV trails, hunting, and fishing, all just minutes from Wisp Resort, Deep Creek Lake, and Swallow Falls State Park. Whether you're planning a full-time home or

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    27 Gobbler Run Rd, Oakland, MD 21550
  • /4

    $150,000

    Sold Jun 25, 2025

    7 Swan Meadow Dr, Mount Lake Park, MD 21550

    • Land
    • 10 Acres
    • $15,000 per Acre

    Last Sold Summary

    Last Listing Agent Rich Orr Railey Realty, Inc.

    7 Swan Meadow Dr, Mount Lake Park, MD 21550
    • /130

      Est $1,087,919

      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

  • /17

    $35,000

    • Land
    • 1.92 Acres
    • $18,229 per Acre

    233 Rhododendron Dr, Oakland, MD 21550

    Fantastic opportunity in the gated community of Youghiogheny Mountain Resort. This 1.92-acre lot is perfect for outdoor enthusiasts, offering ATV riding, hunting, fishing, and more. Build your dream home or a recreational retreat. Approved for a 2-bedroom conventional system, with the option to expand using a sand mound system. Located just minutes from Wisp Resort, Deep Creek Lake, Herrington

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    233 Rhododendron Dr, Oakland, MD 21550
  • /100

    $1,860,000

    Sold Oct 06, 2025

    237 Glendale Rd, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 3,735 Sq Ft
    • Built 2002

    Last Sold Summary

    • $498/SF
    • 88 Days On Market

    Current Estimated Value $1,868,816

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    237 Glendale Rd, Oakland, MD 21550
    • /88

      Est $374,566

      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

  • /32

    $114,000

    $6K PRICE DROP Under Contract
    • 2 Beds
    • 1 Bath
    • 1,029 Sq Ft

    5151 Hutton Rd, Oakland, MD 21550

    REDUCED - Nearly an acre convenient to town - Some upgrades; newer metal roof, electrical panel box, furnace and other areas - Rear carport/patio area has easy at level access to main level - Large front porch with low maintenance entry area with wash/dryer hook-up - Good one level living layout - Sold as-is - No utilities currently active - No repairs before purchase or a lending requirement

    Mark Van Tyne Julian Agency Real Estate

    5151 Hutton Rd, Oakland, MD 21550
  • /46

    $660,000

    Sold Aug 22, 2025

    181 Grand Estates Dr, Mc Henry, MD 21541

    • 4 Beds
    • 2.5 Baths
    • 2,640 Sq Ft
    • Built 2018

    Last Sold Summary

    • $250/SF
    • 56 Days On Market

    Current Estimated Value $692,687

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

    181 Grand Estates Dr, Mc Henry, MD 21541
    • /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

  • /5

    $89,900

    • Land
    • 15.75 Acres
    • $5,708 per Acre

    TBD 15 75 Acres Bethlehem Rd, Oakland, MD 21550

    Tucked away just minutes from town, this 15.75± acre wooded parcel offers a quiet country setting with the privacy many buyers are searching for. Located off Bethlehem Road near the Potomac State Forest, the property features largely level terrain, mature trees, and abundant wildlife—an ideal backdrop for a private residence, weekend retreat, or recreational use. The surrounding area provides

    Thomas Long Railey Realty, Inc.

    TBD 15 75 Acres Bethlehem Rd, Oakland, MD 21550
  • /56

    $157,000

    Sold Aug 29, 2025

    416 Shenandoah Ave, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • Built 1940

    Last Sold Summary

    • $161/SF
    • 4 Days On Market

    Current Estimated Value $151,815

    Last Listing Agent Rich Orr Railey Realty, Inc.

    416 Shenandoah Ave, Oakland, MD 21550
    • /54

      Est $2,394,960

      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

  • /11

    $89,900

    • Land
    • 37,026 Sq Ft
    • $105,765 per Acre

    106 Snowhaven Ln, McHenry, MD 21541

    Build Your Dream Home on the Mountaintop!Don't miss this rare opportunity to own a spacious 0.85-acre lot in one of Deep Creek Lake’s most desirable communities — the Wisp mountaintop. Located on Snowhaven Lane, this lot offers the perfect setting with expansive views for your custom mountain retreat. Just minutes from Wisp Resort, ASCI Whitewater Course, Deep Creek Lake, hiking and biking

    Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

    106 Snowhaven Ln, McHenry, MD 21541
  • /51

    $425,000

    Sold Oct 22, 2025

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,202 Sq Ft
    • Built 2012

    Last Sold Summary

    • $193/SF
    • 130 Days On Market

    Current Estimated Value $436,847

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    • /18

      Est $243,525

      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

  • /25

    $335,000

    • Land
    • 70 Acres
    • $4,786 per Acre

    TBD Highway 50, Gormania, WV 26720

    This uniquely located 70+/- AC property is in close proximity to both Canaan Valley, Timberline Mountain Resort, and Deep Creek Lake, MD with approximately 1 mile of stocked trout water frontage on the North Branch of the Potomac River. An old homestead site along the river would make for a beautiful flat building site. Marketable timber with timber report available. Excellent Hunting. Property

    Steve Galusky Railey WV Properties

    TBD Highway 50, Gormania, WV 26720
  • /17

    $118,800

    Sold Jun 16, 2026

    1995 Bethlehem Rd, Oakland, MD 21550

    • Land
    • 7.33 Acres
    • $16,207 per Acre

    Last Sold Summary

    • 6 Days On Market

    Last Listing Agent Lana Roby The KW Collective

    1995 Bethlehem Rd, Oakland, MD 21550
    • /55

      Est $761,542

      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

  • /34

    $399,900

    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    565 Glendale Rd Unit 303B, Oakland, MD 21550

    Experience lakefront living at its finest in the premier unit at Silver Tree Suites! This beautifully updated 2-bedroom, 1-bath condo showcases rustic charm with custom woodworking throughout. Featuring two separate living areas, there's plenty of space to relax and entertain. Enjoy year-round lake views from the private balcony, unwind by either of the two fireplaces, and appreciate the added

    Sean Sober Taylor-Made Deep Creek Real Estate, LLC

    565 Glendale Rd Unit 303B, Oakland, MD 21550
  • /10

    $55,000

    Sold May 25, 2026

    114 C St, Oakland, MD 21550

    • 768 Sq Ft
    • Built 1999

    Last Sold Summary

    • 8% Below List Price
    • $72/SF
    • 60 Days On Market

    Current Estimated Value $59,602

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

    114 C St, Oakland, MD 21550

Showing Results 401 - 440, Page 11 of 18

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