12,226

Homes in ZIP Code 21550

Section Image
    • 5289 Oakland Sang Run Rd, Oakland, MD 21550
      5289 Oakland Sang Run Rd, Oakland, MD 21550
      5289 Oakland Sang Run Rd, Oakland, MD 21550
      /56

      Est $410,402 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,638 Sq Ft

      5289 Oakland Sang Run Rd, Oakland, MD 21550

      5289 Oakland Sang Run Rd, Oakland, MD 21550
  • 62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    /30

    $249,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,390 Sq Ft

    62 Wild Turkey Ct, Oakland, MD 21550

    Current new home construction project underway, but Builder not going to complete at this time due too busy. So, ready for who may wish to complete project themselves or have completed by others, or current Builder may consider completing for Buyer. Current structure is a custom engineered modular home. This is not a completed or intended by Builder to be completed house project at this time .

    Chip Smith 1 Real Estate Source LLC

    62 Wild Turkey Ct, Oakland, MD 21550
  • 249 Marys Ln, Oakland, MD 21550
    249 Marys Ln, Oakland, MD 21550
    249 Marys Ln, Oakland, MD 21550
    /67

    $855,000 Sold May 12, 2025

    249 Marys Ln, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,874 Sq Ft
    • Built 2017

    Last Sold Summary

    • $297/SF
    • 7 Days On Market

    Current Estimated Value $869,383

    Last Listing Agent Jon Bell Railey Realty, Inc.

    249 Marys Ln, Oakland, MD 21550
    • 620 E Green St, Oakland, MD 21550
      620 E Green St, Oakland, MD 21550
      620 E Green St, Oakland, MD 21550
      /65

      Est $152,297 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,668 Sq Ft

      620 E Green St, Oakland, MD 21550

      620 E Green St, Oakland, MD 21550
  • 0 Highline Dr Unit MDGA2006792, Mc Henry, MD 21541
    0 Highline Dr Unit MDGA2006792, Mc Henry, MD 21541
    0 Highline Dr Unit MDGA2006792, Mc Henry, MD 21541
    /16

    $165,000

    • Land
    • 0.51 Acre
    • $323,529 per Acre

    0 Highline Dr Unit MDGA2006792, Mc Henry, MD 21541

    Mountaintop Lot-If you love the mountains, the lake and the snow-take a look at this location and bring your home plans that will take advantage of all these beautiful aspects of Garrett County! .51 AC lot with utilities to site and easy access to Main St. slope! Public water and sewer hook-ups available.

    Kathy Gibson Railey Realty, Inc.

    0 Highline Dr Unit MDGA2006792, Mc Henry, MD 21541
  • 939 Glendale Rd, Oakland, MD 21550
    939 Glendale Rd, Oakland, MD 21550
    939 Glendale 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 $825,699

    Last Listing Agent Sean Sober Taylor Made Deep Creek Vacations & Sales

    939 Glendale Rd, Oakland, MD 21550
    • 501 G St, Oakland, MD 21550
      501 G St, Oakland, MD 21550
      501 G St, Oakland, MD 21550
      /76

      Est $226,582 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,520 Sq Ft

      501 G St, Oakland, MD 21550

      501 G St, Oakland, MD 21550
  • 315 Coolidge Ave, Oakland, MD 21550
    315 Coolidge Ave, Oakland, MD 21550
    315 Coolidge Ave, Oakland, MD 21550
    /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 Vacations & Sales

    315 Coolidge Ave, Oakland, MD 21550
  • 7 Swan Meadow Dr, Mount Lake Park, MD 21550
    7 Swan Meadow Dr, Mount Lake Park, MD 21550
    7 Swan Meadow Dr, Mount Lake Park, 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
    • 107 Pleasant Hill Cir, Oakland, MD 21550
      107 Pleasant Hill Cir, Oakland, MD 21550
      107 Pleasant Hill Cir, Oakland, MD 21550
      /35

      Est $384,646 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,384 Sq Ft

      107 Pleasant Hill Cir, Oakland, MD 21550

      107 Pleasant Hill Cir, Oakland, MD 21550
  • 12 Greenbrier Dr, Mc Henry, MD 21541
    12 Greenbrier Dr, Mc Henry, MD 21541
    12 Greenbrier Dr, Mc Henry, MD 21541
    /14

    $150,000

    • Land
    • 0.79 Acre
    • $189,873 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 Vacations & Sales

    12 Greenbrier Dr, Mc Henry, MD 21541
  • 186 Sundance Way, McHenry, MD 21541
    186 Sundance Way, McHenry, MD 21541
    186 Sundance Way, McHenry, MD 21541
    /114

    $1,400,000 Sold May 19, 2025

    186 Sundance Way, McHenry, MD 21541

    • 6 Beds
    • 8 Baths
    • 5,758 Sq Ft
    • Built 2025

    Last Sold Summary

    • $243/SF
    • 49 Days On Market

    Current Estimated Value $1,438,464

    Last Listing Agent Michael Fenton Railey Realty, Inc.

    186 Sundance Way, McHenry, MD 21541
    • 125 Matthew Rd, Oakland, MD 21550
      125 Matthew Rd, Oakland, MD 21550
      125 Matthew Rd, Oakland, MD 21550
      /66

      Est $442,783 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,324 Sq Ft

      125 Matthew Rd, Oakland, MD 21550

      125 Matthew Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit 103B, Oakland, MD 21550
    565 Glendale Rd Unit 103B, Oakland, MD 21550
    565 Glendale Rd Unit 103B, Oakland, MD 21550
    /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
  • 237 Glendale Rd, Oakland, MD 21550
    237 Glendale Rd, Oakland, MD 21550
    237 Glendale Rd, 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

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    237 Glendale Rd, Oakland, MD 21550
    • 20488 Garrett Hwy, Oakland, MD 21550
      20488 Garrett Hwy, Oakland, MD 21550
      20488 Garrett Hwy, Oakland, MD 21550
      /6

      Est $684,831 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 840 Sq Ft

      20488 Garrett Hwy, Oakland, MD 21550

      20488 Garrett Hwy, Oakland, MD 21550
  • 20160 Garrett Hwy Unit G507, Oakland, MD 21550
    20160 Garrett Hwy Unit G507, Oakland, MD 21550
    20160 Garrett Hwy Unit G507, Oakland, MD 21550
    /34

    $399,000

    • 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
  • 181 Grand Estates Dr, Mc Henry, MD 21541
    181 Grand Estates Dr, Mc Henry, MD 21541
    181 Grand Estates Dr, Mc Henry, MD 21541
    /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 $688,004

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

    181 Grand Estates Dr, Mc Henry, MD 21541
    • 739 Glendale Rd, Oakland, MD 21550
      739 Glendale Rd, Oakland, MD 21550
      739 Glendale Rd, Oakland, MD 21550
      /85

      Est $1,822,610 Not Listed For Sale

      • 6 Beds
      • 6.5 Baths
      • 4,160 Sq Ft

      739 Glendale Rd, Oakland, MD 21550

      739 Glendale Rd, Oakland, MD 21550
  • 104 Pine Top Trail, Oakland, MD 21550
    104 Pine Top Trail, Oakland, MD 21550
    104 Pine Top Trail, Oakland, MD 21550
    /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
  • 416 Shenandoah Ave, Oakland, MD 21550
    416 Shenandoah Ave, Oakland, MD 21550
    416 Shenandoah Ave, 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 $152,978

    Last Listing Agent Rich Orr Railey Realty, Inc.

    416 Shenandoah Ave, Oakland, MD 21550
    • 723 E Alder St, Oakland, MD 21550
      723 E Alder St, Oakland, MD 21550
      723 E Alder St, Oakland, MD 21550
      /73

      Est $242,111 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft

      723 E Alder St, Oakland, MD 21550

      723 E Alder St, Oakland, MD 21550
  • Lot 69 Sundance Way, Mc Henry, MD 21541
    Lot 69 Sundance Way, Mc Henry, MD 21541
    Lot 69 Sundance Way, Mc Henry, MD 21541
    /15

    $94,000

    • Land
    • 0.69 Acre
    • $136,232 per Acre

    Lot 69 Sundance Way, Mc Henry, MD 21541

    Fabulous golf-front level building lot adjacent to the prestigious lodestone golf course. Build your dream home overlooking hole 6. Easy drive to Wisp ski area and the Adventure sport center international featuring a man made white water course. Great location minutes in quiet neighborhood only minutes from Deep Creek Lake and all area ammenities. Public water and sewer hook up

    Kellyann Green Railey Realty, Inc.

    Lot 69 Sundance Way, Mc Henry, MD 21541
  • 12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    /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

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    • 943 S Blakeslee Rd, Oakland, MD 21550
      943 S Blakeslee Rd, Oakland, MD 21550
      943 S Blakeslee Rd, Oakland, MD 21550
      /130

      Est $1,178,083 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,426 Sq Ft

      943 S Blakeslee Rd, Oakland, MD 21550

      943 S Blakeslee Rd, Oakland, MD 21550
  • Lot 42 Sandstone Cir, Sang Run, MD 21541
    Lot 42 Sandstone Cir, Sang Run, MD 21541
    Lot 42 Sandstone Cir, Sang Run, MD 21541
    /9

    $79,900

    • Land
    • 0.53 Acre
    • $150,755 per Acre

    Lot 42 Sandstone Cir, Sang Run, MD 21541

    Discover the perfect setting for your dream home on Lot 42 Sandstone Circle located in the Lodestone community, just minutes from Wisp Ski & Golf Resort. Enjoy year-round outdoor adventures with ASCI’s world-renowned whitewater course and Deep Creek Lake just a short drive away.With utilities on-site and public water & sewer hookup available, this property is ready for your vision. Whether

    Rich Orr Railey Realty, Inc.

    Lot 42 Sandstone Cir, Sang Run, MD 21541
  • 0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    /3

    $13,000 Sold Apr 14, 2025

    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550

    • Land
    • 2 Acres
    • $6,500 per Acre

    Last Sold Summary

    • 35 Days On Market

    Last Listing Agent Julie Mead The KW Collective

    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    • 223 N 2nd St, Oakland, MD 21550
      223 N 2nd St, Oakland, MD 21550
      223 N 2nd St, Oakland, MD 21550
      /88

      Est $407,559 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,120 Sq Ft

      223 N 2nd St, Oakland, MD 21550

      223 N 2nd St, Oakland, MD 21550
  • 18 Green Jacket Ct, Mc Henry, MD 21541
    18 Green Jacket Ct, Mc Henry, MD 21541
    18 Green Jacket Ct, Mc Henry, MD 21541
    /12

    $134,900

    • Land
    • 0.5 Acre
    • $269,800 per Acre

    18 Green Jacket Ct, Mc Henry, MD 21541

    Enjoy one of the most scenic lots Lodestone has to offer—this .49-acre parcel sits at the end of a quiet cul-de-sac and directly overlooks the #1 Green of the Lodestone Golf Course. You'll love the mountain views and stunning golf course setting. Just minutes from the top of Wisp Resort and the Adventure Sports Center International, this location offers easy access to year-round recreation

    Jessie Railey Railey Realty, Inc.

    18 Green Jacket Ct, Mc Henry, MD 21541
  • 216 Tarn Dr, Oakland, MD 21550
    216 Tarn Dr, Oakland, MD 21550
    216 Tarn Dr, Oakland, MD 21550
    /86

    $1,100,000 Sold Aug 27, 2025

    216 Tarn Dr, Oakland, MD 21550

    • 6 Beds
    • 4.5 Baths
    • 4,769 Sq Ft
    • Built 2020

    Last Sold Summary

    • $231/SF
    • 122 Days On Market

    Current Estimated Value $1,119,839

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

    216 Tarn Dr, Oakland, MD 21550
    • 375 Glendale Rd, Oakland, MD 21550
      375 Glendale Rd, Oakland, MD 21550
      375 Glendale Rd, Oakland, MD 21550
      /54

      Est $2,459,781 Not Listed For Sale

      • 8 Beds
      • 6.5 Baths
      • 5,638 Sq Ft

      375 Glendale Rd, Oakland, MD 21550

      375 Glendale Rd, Oakland, MD 21550
  • 3.35 acres </> 4th St, Oakland, MD 21550
    3.35 acres </> 4th St, Oakland, MD 21550
    3.35 acres </> 4th St, Oakland, MD 21550
    /3

    $150,000

    • Land
    • 3.4 Acres
    • $44,118 per Acre

    3.35 acres </> 4th St, Oakland, MD 21550

    Just over three acres in a prime location in Oakland, Maryland. Property borders the south side of Wal-Mart property and has deeded access from the south entrance of Wal-Mart. Property is wooded but has several flat spots perfect for building. Owner has hired a civil engineer to draw plans for a restaurant, and an office building. Plans are available for review.

    Andrew Orr The KW Collective

    3.35 acres </> 4th St, Oakland, MD 21550
  • 157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    /21

    $295,000 Sold Dec 23, 2025

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 752 Sq Ft
    • Built 1997

    Last Sold Summary

    • $392/SF
    • 21 Days On Market

    Last Listing Agent James Matthews Taylor Made Deep Creek Vacations & Sales

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    • 9 Laurel Brook Dr, Oakland, MD 21550
      9 Laurel Brook Dr, Oakland, MD 21550
      9 Laurel Brook Dr, Oakland, MD 21550
      /18

      Est $249,177 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,200 Sq Ft

      9 Laurel Brook Dr, Oakland, MD 21550

      9 Laurel Brook Dr, Oakland, MD 21550
  • 170 San Francisco St, Oakland, MD 21550
    170 San Francisco St, Oakland, MD 21550
    170 San Francisco St, Oakland, MD 21550
    /12

    $129,900

    • Land
    • 1.38 Acres
    • $94,130 per Acre

    170 San Francisco St, Oakland, MD 21550

    NEW in the Deep Creek Lake and WISP Resort area: three lots at .46 acres each (total is 1.38 acres)! Whether you envision a cozy cabin or a luxury lodge, this parcel offers the ideal blend of seclusion and accessibility. Property Highlights: Private well water source already in place, 200 AMP electric service connection, Approved perc test suitable for a 4-5 bedroom home, Privacy with

    Hunter Shank Coldwell Banker Realty

    170 San Francisco St, Oakland, MD 21550
  • 946 Glendale Rd, Oakland, MD 21550
    946 Glendale Rd, Oakland, MD 21550
    946 Glendale Rd, Oakland, MD 21550
    /100

    $1,765,000 Sold Mar 14, 2025

    946 Glendale Rd, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 3,546 Sq Ft
    • Built 2001

    Last Sold Summary

    • $498/SF
    • 16 Days On Market

    Current Estimated Value $1,784,264

    Last Listing Agent Jon Bell Railey Realty, Inc.

    946 Glendale Rd, Oakland, MD 21550
    • 1557 Mountainview Dr, Oakland, MD 21550
      1557 Mountainview Dr, Oakland, MD 21550
      1557 Mountainview Dr, Oakland, MD 21550
      /55

      Est $818,297 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,590 Sq Ft

      1557 Mountainview Dr, Oakland, MD 21550

      1557 Mountainview Dr, Oakland, MD 21550
  • 611 E Oak St, Oakland, MD 21550
    611 E Oak St, Oakland, MD 21550
    611 E Oak St, Oakland, MD 21550
    /14

    $295,000

    • 5 Beds
    • 3 Baths
    • 1,800 Sq Ft

    611 E Oak St, Oakland, MD 21550

    Investors, this is an income producing, three unit building with three separate apartments, just a few minutes walk to downtown Oakland. Main level and upper level are two bedroom units and basement unit is a one bedroom. All units have current leases in place. One renter has been renting for 12 years, one for 10 years, and the third for eight years. The entire building is in excellent condition.

    Justin Liller Railey Realty, Inc.

    611 E Oak St, Oakland, MD 21550
  • 1567 Pergin Farm Rd, Oakland, MD 21550
    1567 Pergin Farm Rd, Oakland, MD 21550
    1567 Pergin Farm Rd, Oakland, MD 21550
    /67

    $1,542,000 Sold Nov 13, 2025

    1567 Pergin Farm Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,200 Sq Ft
    • Built 2002

    Last Sold Summary

    • $482/SF
    • 15 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1567 Pergin Farm Rd, Oakland, MD 21550
    • 106 H St, Oakland, MD 21550
      106 H St, Oakland, MD 21550
      106 H St, Oakland, MD 21550
      /91

      Est $297,319 Not Listed For Sale

      • 7 Beds
      • 3 Baths
      • 2,934 Sq Ft

      106 H St, Oakland, MD 21550

      106 H St, Oakland, MD 21550

Showing Results 441 - 480, Page 12 of 18

Maryland Garrett County Oakland 21550

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