12,296

Homes in ZIP Code 21550

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    • /42

      Est $684,913

      Not Listed For Sale

      26 Arrowhead Ln, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,000 Sq Ft
      • Built 1988
      26 Arrowhead Ln, Oakland, MD 21550

      Last Sold Summary

      • 389 Days On Market

  • /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
  • /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 $253,284

    Last Listing Agent Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 312, Oakland, MD 21550
    • /26

      Est $159,683

      Not Listed For Sale

      419 Seneca Ave, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,184 Sq Ft
      • Built 1920
      419 Seneca Ave, Oakland, MD 21550

      Last Sold Summary

      • 46 Days On Market

  • /28

    $335,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,288 Sq Ft

    1740 Old Crellin Rd, Oakland, MD 21550

    Come see this beautifully maintained 3-bedroom, 3-bath Colonial-style residence nestled on a private 1-acre lot along Old Crellin Road in Oakland. Offering 2,300 square feet of living space, this home combines classic charm with modern comfort in an ideal location just outside town limits. Step inside to find a spacious and inviting layout, perfect for both everyday living and entertaining. The

    Andrew Orr The KW Collective

    1740 Old Crellin Rd, Oakland, MD 21550
  • /47

    $285,000

    Sold Oct 31, 2025

    1764 Underwood Rd, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,304 Sq Ft
    • Built 1968

    Last Sold Summary

    • $124/SF
    • 175 Days On Market

    Current Estimated Value $275,248

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

    1764 Underwood Rd, Oakland, MD 21550
    • /62

      Est $1,307,043

      Not Listed For Sale

      581 Skippers Point Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,100 Sq Ft
      • Built 1977
      581 Skippers Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

  • /37

    $629,000

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

    231 Santa fe Trail, Oakland, MD 21550

    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 with pool table and

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    231 Santa fe Trail, Oakland, MD 21550
  • /52

    $920,000

    Sold Jun 15, 2026

    1295 Mountainview Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 3,550 Sq Ft
    • Built 2003

    Last Sold Summary

    • $259/SF
    • 3 Days On Market

    Current Estimated Value $935,537

    Last Listing Agent Debbie Roberts Long & Foster Real Estate, Inc.

    1295 Mountainview Dr, Oakland, MD 21550
    • /87

      Est $310,188

      Not Listed For Sale

      233 N 2nd St, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 2,218 Sq Ft
      • Built 1914
      233 N 2nd St, Oakland, MD 21550

      Last Sold Summary

      • 432 Days On Market

  • /14

    $130,000

    $20K PRICE DROP
    • Land
    • 34,412 Sq Ft
    • $164,557 per Acre

    12 Greenbrier Dr, Mc Henry, MD 21541

    Homesite #12 in the mountaintop and golf course community of Lodestone is a perfect spot to build your dream home. This lot has public water and sewer hookup available, making the possibilities endless. Offering beautiful mountain and golf course views. You are also just minutes to Lodestone Golf Course, Deep Creek Lake, Wisp Ski Resort and the whitewater course.

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

    12 Greenbrier Dr, Mc Henry, MD 21541
  • /56

    $697,000

    Sold Dec 19, 2025

    969 Hoyes Run Rd, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,614 Sq Ft
    • Built 1998

    Last Sold Summary

    • $193/SF
    • 180 Days On Market

    Current Estimated Value $709,977

    Last Listing Agent Roberta McNamara RE/MAX Results

    969 Hoyes Run Rd, Oakland, MD 21550
    • /76

      Est $593,694

      Not Listed For Sale

      1094 Eagle Rock Rd, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 3,780 Sq Ft
      • Built 2008
      1094 Eagle Rock Rd, Oakland, MD 21550

      Last Sold Summary

      • 109 Days On Market

  • /53

    $260,000

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 103B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites! This inviting one-bedroom layout features a gas fireplace, full bath with tub/shower, and a tidy kitchenette equipped with a microwave, dishwasher, and full-size refrigerator. Balcony doors open to fresh Deep Creek air and filtered lake views, with a private deck that is perfect for relaxing after a day on the water. Enjoy a variety of

    Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 103B, Oakland, MD 21550
  • /2

    $10,000

    Sold Dec 19, 2025

    0 Maryland Hwy, Swanton, MD 21561

    • Land
    • 1.6 Acres
    • $6,250 per Acre

    Last Sold Summary

    • 220 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    0 Maryland Hwy, Swanton, MD 21561
    • /34

      Est $202,713

      Not Listed For Sale

      700 N St, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,724 Sq Ft
      • Built 1973
      700 N St, Oakland, MD 21550

      Last Sold Summary

      • 57 Days On Market

  • /38

    $389,000

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    20160 Garrett Hwy Unit G507, Oakland, MD 21550

    Experience lakefront living with this charming two-level condo at Will O the Wisp at Deep Creek Lake! Offering 2 bedrooms and 1 full bathroom, it captures breathtaking lake views from both levels. The main floor features a functional kitchen and a cozy living area with a wood-burning fireplace—perfect for relaxing after a day on the water. Upstairs, you’ll find two comfortable bedrooms and a full

    Nina Beitzel Railey Realty, Inc.

    20160 Garrett Hwy Unit G507, Oakland, MD 21550
  • /29

    $225,000

    Sold Nov 17, 2025

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 520 Sq Ft
    • Built 1990

    Last Sold Summary

    • $433/SF
    • 26 Days On Market

    Current Estimated Value $225,025

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    • /46

      Est $318,882

      Not Listed For Sale

      134 Skippers Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,497 Sq Ft
      • Built 1990
      134 Skippers Ln, Oakland, MD 21550

      Last Sold Summary

      • 59 Days On Market

  • /59

    $820,000

    $55K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,178 Sq Ft

    448 Biltmore View, Mc Henry, MD 21541

    Welcome to this beautifully crafted 5-bedroom, 3-bath, two-story home in the desirable Biltmore community at Lodestone Golf Course. Built in 2022, this thoughtfully designed property blends modern mountain style with quality craftsmanship, offering solid finishes inside and out and a layout ideal for both everyday living and vacation enjoyment. The open-concept main level features spacious living

    Nina Beitzel Railey Realty, Inc.

    448 Biltmore View, Mc Henry, MD 21541
  • /39

    $195,000

    Sold Nov 12, 2025

    501 Christophers Way, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • Built 1994

    Last Sold Summary

    • $121/SF
    • 138 Days On Market

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

    501 Christophers Way, Oakland, MD 21550
    • /48

      Est $224,201

      Not Listed For Sale

      1634 Shady Dell Rd, Oakland, MD 21550

      • 4 Beds
      • 1 Bath
      • 1,176 Sq Ft
      • Built 1950
      1634 Shady Dell Rd, Oakland, MD 21550

      Last Sold Summary

      • 21 Days On Market

  • /13

    $425,000

    • 3 Beds
    • 3.5 Baths
    • 1,596 Sq Ft

    104 Pine Top Trail, Oakland, MD 21550

    Here's your chance to purchase a cute Chalet with just about 7 acres. .This home and acreage is right next to the Common Grounds and gives you immediate river access.

    laura Flynn 1 Real Estate Source LLC

    104 Pine Top Trail, Oakland, MD 21550
  • /41

    $218,000

    Sold Dec 01, 2025

    1136 Black Oak Dr, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1971

    Last Sold Summary

    • $206/SF
    • 7 Days On Market

    Current Estimated Value $221,447

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

    1136 Black Oak Dr, Oakland, MD 21550
    • /51

      Est $245,729

      Not Listed For Sale

      685 Oakland Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,378 Sq Ft
      • Built 1975
      685 Oakland Dr, Oakland, MD 21550

      Last Sold Summary

      • 21 Days On Market

  • /7

    $15,000

    $15K PRICE DROP
    • Land
    • 40,075 Sq Ft
    • $16,304 per Acre

    0 Maryland Hwy Unit MDGA2011452, Oakland, MD 21550

    This is an estate listing. The parcel is 0.92 Acre that is wooded and vacant.The lot failed to Perc.

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    0 Maryland Hwy Unit MDGA2011452, Oakland, MD 21550
  • /18

    $200,000

    Sold Sep 15, 2025

    2571 Shady Dell Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • Built 1985

    Last Sold Summary

    • $119/SF
    • 62 Days On Market

    Current Estimated Value $265,030

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    2571 Shady Dell Rd, Oakland, MD 21550
    • /40

      Est $169,891

      Not Listed For Sale

      5459 Hutton Rd, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 1940
      5459 Hutton Rd, Oakland, MD 21550

      Last Sold Summary

      • 113 Days On Market

  • /82

    $875,000

    Under Contract
    • 3 Beds
    • 4 Baths
    • 3,990 Sq Ft

    891 Mountainview Dr, Oakland, MD 21550

    Discover the perfect blend of rustic charm and modern comfort in this inviting turnkey 3‐bedroom mountaintop chalet with lake access, set on 1.17 private acres with expansive outdoor entertainment space. Whether you're hosting friends or enjoying quiet mountain evenings, this fully-furnished home delivers an unforgettable retreat. Inside, the great room impresses with a soaring stacked‐stone

    Brent Housley Railey Realty, Inc.

    891 Mountainview Dr, Oakland, MD 21550
  • /93

    $1,445,000

    Sold Nov 14, 2025

    128 Big Bass Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,305 Sq Ft
    • Built 2023

    Last Sold Summary

    • $336/SF
    • 13 Days On Market

    Current Estimated Value $1,400,033

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    128 Big Bass Dr, Oakland, MD 21550
    • /22

      Est $182,210

      Not Listed For Sale

      615 E High St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,180 Sq Ft
      • Built 1920
      615 E High St, Oakland, MD 21550

      Last Sold Summary

      • 257 Days On Market

  • /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
  • /78

    $1,780,000

    Sold Dec 19, 2025

    2345 Marsh Hill Rd, Mc Henry, MD 21541

    • 6 Beds
    • 6 Baths
    • 5,373 Sq Ft
    • Built 1990

    Last Sold Summary

    • $331/SF
    • 53 Days On Market

    Current Estimated Value $1,801,879

    Last Listing Agent James Matthews Taylor-Made Deep Creek Real Estate, LLC

    2345 Marsh Hill Rd, Mc Henry, MD 21541
    • /87

      Est $463,273

      Not Listed For Sale

      524 Bray School Rd, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,536 Sq Ft
      • Built 2003
      524 Bray School Rd, Oakland, MD 21550

      Last Sold Summary

      • 11 Days On Market

  • /18

    $3,000

    • Land
    • 24,393 Sq Ft
    • $5,357 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
  • /56

    $320,000

    Sold Nov 05, 2025

    531 S 3rd St, Oakland, MD 21550

    • 5 Beds
    • 2.5 Baths
    • 2,477 Sq Ft
    • Built 1920

    Last Sold Summary

    • $129/SF
    • 118 Days On Market

    Current Estimated Value $316,080

    Last Listing Agent Jennifer Jackson Charis Realty Group

    531 S 3rd St, Oakland, MD 21550
    • /38

      Est $167,267

      Not Listed For Sale

      514 M St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,326 Sq Ft
      • Built 1945
      514 M St, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /8

    $100,000

    $100K PRICE DROP
    • Land
    • 5 Acres
    • $20,000 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
  • /52

    $840,000

    Sold Jan 31, 2026

    35 Blue Mountain View, McHenry, MD 21541

    • 5 Beds
    • 4.5 Baths
    • 2,832 Sq Ft
    • Built 2022

    Last Sold Summary

    • 16% Below List Price
    • $297/SF
    • 221 Days On Market

    Current Estimated Value $850,375

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    35 Blue Mountain View, McHenry, MD 21541
    • /50

      Est $330,831

      Not Listed For Sale

      15705 Garrett Hwy, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,046 Sq Ft
      • Built 1965
      15705 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 146 Days On Market

Showing Results 561 - 600, Page 15 of 18

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