12,226

Homes in ZIP Code 21550

Section Image
  • /71

    $912,500 Sold Dec 05, 2025

    78 Mountainside Ct, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,492 Sq Ft
    • Built 2002

    Last Sold Summary

    • $261/SF
    • 61 Days On Market

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    78 Mountainside Ct, Oakland, MD 21550
    • /73

      Est $1,004,119 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,440 Sq Ft

      144 Middleton Rd, Oakland, MD 21550

      144 Middleton Rd, Oakland, MD 21550
  • /10

    $649,000 Under Contract

    • Land
    • 37.8 Acres
    • $17,169 per Acre

    13209 Garrett Hwy, Oakland, MD 21550

    Access to Public Utilities and Natural Gas within the Town of Oakland Utility systems.Access to Public Utilities and Natural Gas within the Town of Oakland Utility systems. Property has State Highway Entrance completed. New Owner would utilize this access Road to develop property. Recorded plat and Covenants available online.

    Rich Orr Railey Realty, Inc.

    13209 Garrett Hwy, Oakland, MD 21550
  • /76

    $420,000 Sold Oct 15, 2025

    783 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,971 Sq Ft
    • Built 2002

    Last Sold Summary

    • $213/SF
    • 122 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    783 Mountainview Dr, Oakland, MD 21550
    • /58

      Est $1,533,652 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,200 Sq Ft

      2411 Lake Shore Dr, Oakland, MD 21550

      2411 Lake Shore Dr, Oakland, MD 21550
  • /45

    $775,000 Under Contract

    • 3 Beds
    • 3 Baths
    • 2,744 Sq Ft

    198 Grandview Dr, Oakland, MD 21550

    Lake views for days and room to relax in every direction!Welcome to 198 Grandview Drive, a 3-bedroom, 3-bath log home perfectly perched to capture sweeping views of Deep Creek Lake and the surrounding mountains. With three finished levels of living space, this home blends rustic charm with modern comfort. Hardwood floors span the main and upper levels, while the finished lower level features

    Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, MD 21550
  • /35

    $380,000 Sold Sep 26, 2025

    20160 Garrett Hwy Unit G509, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1974

    Last Sold Summary

    • $594/SF
    • 24 Days On Market

    Last Listing Agent Tim Macauley Taylor Made Deep Creek Vacations & Sales

    20160 Garrett Hwy Unit G509, Oakland, MD 21550
    • /132

      Est $3,656,455 Not Listed For Sale

      • 5 Beds
      • 7 Baths
      • 9,134 Sq Ft

      2524 Stockslager Rd, Oakland, MD 21550

      2524 Stockslager Rd, Oakland, MD 21550
  • /5

    $30,000

    • Land
    • 0.34 Acre
    • $88,235 per Acre

    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550

    Love Deep Creek Lake living. This 0.34 acre wooded lot sits near the heart of everything that makes the lake special. Launch the boat at nearby marinas, hike and swim at Deep Creek Lake State Park, and enjoy four season adventure at Wisp Resort with skiing, tubing, and mountain rides. Restaurants, shops, and local events are just down the road, while your homesite feels peaceful and private. Do

    Debra Hayne Cummings & Co. Realtors

    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
  • /13

    $20,000 Sold Nov 05, 2025

    0 Weber Ct, Oakland, MD 21550

    • Land
    • 0.24 Acre
    • $83,333 per Acre

    Last Sold Summary

    • 10 Days On Market

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    0 Weber Ct, Oakland, MD 21550
    • /32

      Est $581,650 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft

      1519 Mayhew Inn Rd, Oakland, MD 21550

      1519 Mayhew Inn Rd, Oakland, MD 21550
  • /3

    $45,900

    • Land
    • 1.02 Acres
    • $45,000 per Acre

    Lot 14 Warnick Way, Oakland, MD 21550

    Enjoy mountain views from this 1.02-acre, mostly wooded lot! No mobile homes permitted. No HOA. Easy access off Spring Glade Rd. Ideally situated between Oakland and Deep Creek Lake. Contact me today for more info!

    Nicole Jackson Railey Realty, Inc.

    Lot 14 Warnick Way, Oakland, MD 21550
  • /7

    $90,000 Sold Feb 07, 2025

    Lot 5 Bobcat Hill Ln, Oakland, MD 21550

    • Land
    • 2.36 Acres
    • $38,136 per Acre

    Last Sold Summary

    • 43 Days On Market

    Last Listing Agent Kim Palmer Marquee Properties, Inc.

    Lot 5 Bobcat Hill Ln, Oakland, MD 21550
    • /21

      Est $550,188 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 3,612 Sq Ft

      471 Clifton Dr, Oakland, MD 21550

      471 Clifton Dr, Oakland, MD 21550
  • /34

    $299,500 Under Contract

    • 3 Beds
    • 3 Baths

    34 Laurel Brook Dr, Oakland, MD 21550

    Welcome to 34 Laurel Brook Drive! An impeccably remodeled townhome just moments from Deep Creek Lake and Oakland, Maryland. Renovated in 2019 and among the larger homes in the neighborhood, this property features 3 bedrooms, 3 full bathrooms, and over 2,000 sq ft of finished space. Highlights include stylish flooring, a modern kitchen, and recent upgrades such as new skylights and primary bedroom

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    34 Laurel Brook Dr, Oakland, MD 21550
  • /40

    $335,000 Sold May 23, 2025

    465 King Wildesen Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1988

    Last Sold Summary

    • 22% Below List Price
    • $436/SF
    • 123 Days On Market

    Current Estimated Value $332,490

    Last Listing Agent ADAM MURRAY BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    465 King Wildesen Rd, Oakland, MD 21550
    • /68

      Est $1,416,448 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,854 Sq Ft

      1835 Marsh Hill Rd, Mc Henry, MD 21541

      1835 Marsh Hill Rd, Mc Henry, MD 21541
  • /50

    $379,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    961 Cedar Ln, Oakland, MD 21550

    Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat offers privacy, comfort, and plenty of space to unwind. Step inside to find a warm and inviting main level highlighted by a stone fireplace, cozy dining area, and galley-style kitchen. Relax on the screened-in porch complete with a hot tub under roof, perfect for year-round enjoyment. The finished basement

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    961 Cedar Ln, Oakland, MD 21550
  • /20

    $17,000 Sold Oct 29, 2025

    9 & 10 Grouse Run Rd, Oakland, MD 21550

    • Land
    • 0.96 Acre
    • $17,708 per Acre

    Last Sold Summary

    • 50 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    9 & 10 Grouse Run Rd, Oakland, MD 21550
    • /81

      Est $797,229 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,921 Sq Ft

      43 Robinwood Dr, Oakland, MD 21550

      43 Robinwood Dr, Oakland, MD 21550
  • /12

    $45,000

    • Land
    • 0.34 Acre
    • $132,353 per Acre

    LOT 181 Santa fe Trail, Oakland, MD 21550

    Don't miss the opportunity to own a lake area lot near the one and only Deep Creek Lake. 0.34 acre wooded lot, close to multiple local attractions. Call today! Verify utilities with Garrett County Environmental Department. Being sold subject to successful perc.

    Amy Skipper Railey Realty, Inc.

    LOT 181 Santa fe Trail, Oakland, MD 21550
  • /2

    $8,000 Sold Aug 29, 2025

    0 E Water St, Oakland, MD 21550

    • Land
    • 0.33 Acre
    • $24,242 per Acre

    Last Sold Summary

    • 2 Days On Market

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

    0 E Water St, Oakland, MD 21550
    • /16

      Est $66,345 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 964 Sq Ft

      36 Preston Ln, Oakland, MD 21550

      36 Preston Ln, Oakland, MD 21550
  • /26

    $169,000

    • Land
    • 0.57 Acre
    • $296,491 per Acre

    Lot 47 Mountaintop Rd, McHenry, MD 21550

    Build your dream mountain retreat in the prestigious Deep Creek Highlands! This prime building lot is ideally situated next to a serene association common area, offering added privacy and natural beauty. Distinctive rock outcroppings on the property create the perfect canvas for a truly unique architectural design that blends seamlessly with the landscape. Enjoy all the community amenities

    Larry Smith Railey Realty, Inc.

    Lot 47 Mountaintop Rd, McHenry, MD 21550
  • /2

    $110,000 Sold May 09, 2025

    Lot 22 Winding Estates Dr, Mc Henry, MD 21550

    • Land
    • 1.07 Acres
    • $102,804 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    Lot 22 Winding Estates Dr, Mc Henry, MD 21550
    • /44

      Est $746,238 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,896 Sq Ft

      870 Hunters Ridge Dr, Oakland, MD 21550

      870 Hunters Ridge Dr, Oakland, MD 21550
  • /4

    $29,900

    • Land
    • 1.09 Acres
    • $27,431 per Acre

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550

    1+ acre building lot. Fairly leveled cleared lot with some distant mountain views. Paved County road frontage with private road/drive access to lot. Approved for private septic and well. Electric on-site. Located approx. 10+ mins from Deep Creek Lake and approx. less than 5 minutes from Oakland. Located within small 8 lot development, "The Homestead".

    Chip Smith 1 Real Estate Source LLC

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
  • /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

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    204 E St, Oakland, MD 21550
    • /36

      Est $648,341 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,053 Sq Ft

      21651 Garrett Hwy, Deer Park, MD 21550

      21651 Garrett Hwy, Deer Park, MD 21550
  • /59

    $779,000

    • 5 Beds
    • 1.5 Baths
    • 1,278 Sq Ft

    222 Skippers Point Rd, Oakland, MD 21550

    Lovely level lot with path to your own private class A dock, directly across the street. This comfy cottage sits on 1.8 level acres with 2 storage garages and mature landscaping. 5BRs, open living, dinning & kitchen area, with lots of sunlight. 1 full & 1-1/2 bath, large closet for storge, laundry room off back of the home. 2 garages with plenty of storge for your lake and yard toys. The lot has

    Julie Mead The KW Collective

    222 Skippers Point Rd, Oakland, MD 21550
  • /52

    $250,000 Sold Mar 21, 2025

    5267 George Washington Hwy, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,352 Sq Ft
    • Built 1974

    Last Sold Summary

    • $106/SF
    • 153 Days On Market

    Current Estimated Value $250,595

    Last Listing Agent Jennifer Jackson Charis Realty Group

    5267 George Washington Hwy, Oakland, MD 21550
    • /125

      Est $2,369,370 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,584 Sq Ft

      427 Lake Shore Dr, Oakland, MD 21550

      427 Lake Shore Dr, Oakland, MD 21550
  • /8

    $17,000

    • Land
    • 0.77 Acre
    • $22,078 per Acre

    Lot 40 W Big Piney Dr, Oakland, MD 21550

    Located in the Youghiogheny Mountain Resort community, this .77ac lot offers the ultimate gateway to peaceful surroundings, beautiful views, and abundant wildlife. Approved for a sand mound sewage system, this lot provides the perfect opportunity to build your future outdoor enthusiast retreat! Enjoy exclusive access to over 50 miles of private roads and trails perfect for ATV and side-by-side

    Elizabeth Broadwater Taylor Made Deep Creek Vacations & Sales

    Lot 40 W Big Piney Dr, 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 $269,679

    Last Listing Agent ANGELA BOSLEY Taylor Made Deep Creek Vacations & Sales

    403 O St, Oakland, MD 21550
    • /65

      Est $4,099,735 Not Listed For Sale

      • 8 Beds
      • 5.5 Baths
      • 8,453 Sq Ft

      2276 Paradise Point Rd, Oakland, MD 21550

      2276 Paradise Point Rd, Oakland, MD 21550
  • /11

    $122,500

    • Land
    • 13.57 Acres
    • $9,027 per Acre

    Lot 3 Deer Run Rd, 14, West Oakland, MD 21550

    Rare Opportunity in Youghiogheny Mountain Resort – 13.57 Acres on Deer Run RoadThis is a unique chance to own a substantial 13.57-acre parcel in Youghiogheny Mountain Resort (YMR), a private, gated community where most lots have already been subdivided into much smaller parcels. Whether you're seeking privacy, recreation, or a place to build your dream home or cabin, Lot 3 on Deer Run

    Thomas Long Railey Realty, Inc.

    Lot 3 Deer Run Rd, 14, West Oakland, MD 21550
  • /80

    $696,000 Sold Apr 02, 2025

    1489 Mountainview Dr, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,066 Sq Ft
    • Built 2001

    Last Sold Summary

    • $227/SF
    • 170 Days On Market

    Current Estimated Value $706,991

    Last Listing Agent Larry Smith Railey Realty, Inc.

    1489 Mountainview Dr, Oakland, MD 21550
    • /84

      Est $541,117 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,400 Sq Ft

      1113 White Pine Cir, Oakland, MD 21550

      1113 White Pine Cir, Oakland, MD 21550
  • /13

    $70,000 Under Contract

    • Land
    • 1 Acre
    • $70,000 per Acre

    Lot 38 Winding Estates Dr, Mc Henry, MD 21550

    Discover the perfect spot to build your mountain retreat in Lago Vista, just minutes from Deep Creek Lake! This beautiful building lot offers stunning mountain views and access to public utility hookups for added convenience. Located close to Wisp Resort, state parks, and all the area's top amenities, it’s an ideal setting for year-round living or a vacation getaway. With an affordable price tag

    Nina Beitzel Railey Realty, Inc.

    Lot 38 Winding Estates Dr, Mc Henry, 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 $1,414,329

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    421 Penn Cove Rd, Oakland, MD 21550

Showing Results 401 - 440, Page 11 of 18

How to Buy a Home How to Finance a Home How to Sell a Home