12,226

Homes in ZIP Code 21550

Section Image
  • 426 Pergin Farm Rd, Oakland, MD 21550
    426 Pergin Farm Rd, Oakland, MD 21550
    426 Pergin Farm Rd, Oakland, MD 21550
    /42

    $430,000 Sold Mar 27, 2025

    426 Pergin Farm Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,596 Sq Ft
    • Built 1985

    Last Sold Summary

    • $269/SF
    • 15 Days On Market

    Current Estimated Value $440,954

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    426 Pergin Farm Rd, Oakland, MD 21550
    • 135 Tarn Dr, Oakland, MD 21550
      135 Tarn Dr, Oakland, MD 21550
      135 Tarn Dr, Oakland, MD 21550
      /25

      Not Listed For Sale

      135 Tarn Dr, Oakland, MD 21550

      135 Tarn Dr, Oakland, MD 21550
  • 3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    /31

    $1,800,000

    • 4 Beds
    • 6 Baths
    • 5,117 Sq Ft

    3898 Underwood Rd, Oakland, MD 21550

    One of a kind 4 BR 4 BA brick Home. 5,100 sq. ft. + 3 car garage. Situated on 23.47 elevated acres with unbelievable panoramic views of Pleasant Valley and surrounding farming community. Living area on one level with full unfinished basement. Views from every room. Massive amount of closet space The opportunities are abundant with this property.

    Robert Custer Custer Realty & Auction

    3898 Underwood Rd, Oakland, MD 21550
  • 290 Crellin Underwood Rd, Oakland, MD 21550
    290 Crellin Underwood Rd, Oakland, MD 21550
    290 Crellin Underwood Rd, Oakland, MD 21550
    /65

    $280,500 Sold Sep 12, 2025

    290 Crellin Underwood Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,208 Sq Ft
    • Built 1982

    Last Sold Summary

    • $127/SF
    • 96 Days On Market

    Current Estimated Value $277,867

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    290 Crellin Underwood Rd, Oakland, MD 21550
    • 17 Old Chestnut Dr, Oakland, MD 21550
      17 Old Chestnut Dr, Oakland, MD 21550
      17 Old Chestnut Dr, Oakland, MD 21550
      /49

      Est $904,442 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 966 Sq Ft

      17 Old Chestnut Dr, Oakland, MD 21550

      17 Old Chestnut Dr, Oakland, MD 21550
  • 697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    /56

    $339,000

    • 5 Beds
    • 3.5 Baths
    • 3,682 Sq Ft

    697 Monte Vista Rd, Oakland, MD 21550

    Tucked away just minutes from downtown Oakland, MD, lies a home that truly surprises with over 3,500 sq. ft. of living space on 1.88 acres with breathtaking farm and mountain views. Step inside the main level, where the master suite awaits along with two additional large bedrooms and a full bath, plus a mudroom area with a convenient half bath—perfect for entertaining. Cozy evenings are made even

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    697 Monte Vista Rd, Oakland, MD 21550
  • 53 Oak St, Deer Park, MD 21550
    53 Oak St, Deer Park, MD 21550
    53 Oak St, Deer Park, MD 21550
    /52

    $160,000 Sold Mar 11, 2025

    53 Oak St, Deer Park, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 2007

    Last Sold Summary

    • $114/SF
    • 119 Days On Market

    Last Listing Agent Justin Liller Railey Realty, Inc.

    53 Oak St, Deer Park, MD 21550
    • 535 Deep Creek Highlands Rd, McHenry, MD 21550
      535 Deep Creek Highlands Rd, McHenry, MD 21550
      535 Deep Creek Highlands Rd, McHenry, MD 21550
      /122

      Not Listed For Sale

      • 7 Beds
      • 5.5 Baths
      • 4,320 Sq Ft

      535 Deep Creek Highlands Rd, McHenry, MD 21550

      535 Deep Creek Highlands Rd, McHenry, MD 21550
  • LOT 7 Grand Estates Dr, Sang Run, MD 21541
    LOT 7 Grand Estates Dr, Sang Run, MD 21541
    LOT 7 Grand Estates Dr, Sang Run, MD 21541
    /8

    $69,000

    • Land
    • 0.66 Acre
    • $104,545 per Acre

    LOT 7 Grand Estates Dr, Sang Run, MD 21541

    Looking for the perfect spot to build your Deep Creek Lake getaway? This prime mountaintop lot in Lago Vista is ready for your dream home. With public utilities available, you can start planning your mountain retreat, full-time residence, or investment property with ease. Enjoy having Wisp Resort and Lodestone Golf Club practically in your backyard, plus all the fun and adventure of Deep Creek

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    LOT 7 Grand Estates Dr, Sang Run, MD 21541
  • 502 E Oak St, Oakland, MD 21550
    502 E Oak St, Oakland, MD 21550
    502 E Oak St, Oakland, MD 21550
    /41

    $239,900 Sold Sep 12, 2025

    502 E Oak St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1956

    Last Sold Summary

    • $143/SF
    • 17 Days On Market

    Current Estimated Value $238,303

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    502 E Oak St, Oakland, MD 21550
    • 6 Greenbrier Dr, Mc Henry, MD 21541
      6 Greenbrier Dr, Mc Henry, MD 21541
      6 Greenbrier Dr, Mc Henry, MD 21541
      /13

      Not Listed For Sale

      6 Greenbrier Dr, Mc Henry, MD 21541

      6 Greenbrier Dr, Mc Henry, MD 21541
  • 126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    /50

    $529,900

    • 4 Beds
    • 3 Baths
    • 2,235 Sq Ft

    126 Leo Friend Rd, Oakland, MD 21550

    Perched above the treetops with panoramic lake views, this three-level retreat blends comfort with clean, considered upgrades. Vaulted ceilings and a spacious loft crown 2,235 square feet of living space, wrapped in new flooring with fresh paint inside and out. The kitchen, smartly updated with new countertops, connects to open dining and living anchored by a wood stove. A detached garage sits

    Jon Bell Railey Realty, Inc.

    126 Leo Friend Rd, Oakland, MD 21550
  • 116 Wanderer Ln Unit F5, Oakland, MD 21550
    116 Wanderer Ln Unit F5, Oakland, MD 21550
    116 Wanderer Ln Unit F5, Oakland, MD 21550
    /97

    $732,500 Sold Jun 09, 2025

    116 Wanderer Ln Unit F5, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1975

    Last Sold Summary

    • $509/SF
    • 6 Days On Market

    Current Estimated Value $727,914

    Last Listing Agent Charlene Deremer Coldwell Banker Home Town Realty

    116 Wanderer Ln Unit F5, Oakland, MD 21550
    • 503 Southern Pines Dr, Oakland, MD 21550
      503 Southern Pines Dr, Oakland, MD 21550
      503 Southern Pines Dr, Oakland, MD 21550
      /10

      Est $123,333 Not Listed For Sale

      503 Southern Pines Dr, Oakland, MD 21550

      503 Southern Pines Dr, Oakland, MD 21550
  • 0 Crosby Dr Unit 64/65, Oakland, MD 21550
    0 Crosby Dr Unit 64/65, Oakland, MD 21550
    0 Crosby Dr Unit 64/65, Oakland, MD 21550
    /55

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,986 Sq Ft

    0 Crosby Dr Unit 64/65, Oakland, MD 21550

    TO BE BUILT on lots 64 & 65 Country Club Acres - 3BR, 2BA new construction with full walkout basement & attached 2 car garage fronting on hole #13 of the Oakland golf course. Impressive views from .61+/- acres of land, rare privacy and modern floor plan. 1,986 sf of finished living space on the first floor and 1,986 sq ft unfinished basement will have a full bath rough-in and can be finished

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    0 Crosby Dr Unit 64/65, Oakland, MD 21550
  • 131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    /53

    $495,000 Sold Oct 08, 2025

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,422 Sq Ft
    • Built 2004

    Last Sold Summary

    • $204/SF
    • 106 Days On Market

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

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    • 74 Chimney Rock Ln, Mc Henry, MD 21541
      74 Chimney Rock Ln, Mc Henry, MD 21541
      74 Chimney Rock Ln, Mc Henry, MD 21541
      /10

      Not Listed For Sale

      74 Chimney Rock Ln, Mc Henry, MD 21541

      74 Chimney Rock Ln, Mc Henry, MD 21541
  • 0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
    /6

    $119,000

    • Land
    • 3.1 Acres
    • $38,387 per Acre

    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550

    This is the building site you've been waiting for! Lot 29 is located in a subdivision called the View, and it lives up to the name! Offering a generous 3.10 Acres with possible lake views this attractive location is close to lake amenities while giving a sense of privacy. Call today for more information!

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
  • 5154 Maryland Hwy, Oakland, MD 21550
    5154 Maryland Hwy, Oakland, MD 21550
    5154 Maryland Hwy, Oakland, MD 21550
    /65

    $375,000 Sold Jul 29, 2025

    5154 Maryland Hwy, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 2,860 Sq Ft
    • Built 1980

    Last Sold Summary

    • $131/SF
    • 23 Days On Market

    Current Estimated Value $377,662

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    5154 Maryland Hwy, Oakland, MD 21550
    • 15 Fawn Dr, Oakland, MD 21550
      15 Fawn Dr, Oakland, MD 21550
      15 Fawn Dr, Oakland, MD 21550
      /32

      Est $156,000 Not Listed For Sale

      15 Fawn Dr, Oakland, MD 21550

      15 Fawn Dr, Oakland, MD 21550
  • 565 Glendale Rd Unit 106B, Oakland, MD 21550
    565 Glendale Rd Unit 106B, Oakland, MD 21550
    565 Glendale Rd Unit 106B, Oakland, MD 21550
    /27

    $239,900

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 106B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs in a gas fireplace, full bath with tub/shower, and a tidy kitchenette with microwave, dishwasher, and full fridge. Balcony doors open to Deep Creek air and filtered lake scenes. Community perks include sauna, gym, game room and more. Sold turn-key, fully furnished. Ductless units for heat and A/C. Monthly

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 106B, Oakland, MD 21550
  • 62 Middleton Rd, Oakland, MD 21550
    62 Middleton Rd, Oakland, MD 21550
    62 Middleton Rd, Oakland, MD 21550
    /67

    $760,000 Sold Nov 14, 2025

    62 Middleton Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,397 Sq Ft
    • Built 1993

    Last Sold Summary

    • $317/SF
    • 113 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Middleton Rd, Oakland, MD 21550
    • 18 Autumn Way, Oakland, MD 21550
      18 Autumn Way, Oakland, MD 21550
      18 Autumn Way, Oakland, MD 21550
      /11

      Not Listed For Sale

      18 Autumn Way, Oakland, MD 21550

      18 Autumn Way, Oakland, MD 21550
  • 1570 Garrett Rd, Oakland, MD 21550
    1570 Garrett Rd, Oakland, MD 21550
    1570 Garrett Rd, Oakland, MD 21550
    /27

    $245,000

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft

    1570 Garrett Rd, Oakland, MD 21550

    Located between Oakland and Deep Creek Lake, this log ranch is situated on 14.82 acres, including a stream, pond, barn and outbuildings with many possibilities to include potential subdivision configurations. The log home needs some TLC and updates; it is being sold as part of an estate. Some items of personal property remain in the house and on grounds. Those items are being removed. More photos

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    1570 Garrett Rd, Oakland, MD 21550
  • 254 Middleton Rd, Oakland, MD 21550
    254 Middleton Rd, Oakland, MD 21550
    254 Middleton Rd, Oakland, MD 21550
    /63

    $920,000 Sold Aug 22, 2025

    254 Middleton Rd, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 2,400 Sq Ft
    • Built 1994

    Last Sold Summary

    • $383/SF
    • 19 Days On Market

    Current Estimated Value $919,538

    Last Listing Agent Jon Bell Railey Realty, Inc.

    254 Middleton Rd, Oakland, MD 21550
    • 20476 Garrett Hwy, Oakland, MD 21550
      20476 Garrett Hwy, Oakland, MD 21550
      20476 Garrett Hwy, Oakland, MD 21550
      /82

      Est $1,302,197 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 2,635 Sq Ft

      20476 Garrett Hwy, Oakland, MD 21550

      20476 Garrett Hwy, Oakland, MD 21550
  • 102 Roanoke Ave, Oakland, MD 21550
    102 Roanoke Ave, Oakland, MD 21550
    102 Roanoke Ave, Oakland, MD 21550
    /7

    $130,000

    • 4 Beds
    • 1.5 Baths
    • 1,932 Sq Ft

    102 Roanoke Ave, Oakland, MD 21550

    4-bedroom, 1.5-bath home located on a spacious corner lot in Loch Lynn. This two-story property features generous living space and several recent updates, including a new furnace, roof, windows, and stove. A newer deck offers additional outdoor enjoyment. The home is conveniently located near the Loch Lynn soccer fields and just a few minutes from downtown Oakland. Solid structure with great

    Heather Homberg Taylor Made Deep Creek Vacations & Sales

    102 Roanoke Ave, Oakland, MD 21550
  • 111 Knoll Crest Heights Dr, Oakland, MD 21550
    111 Knoll Crest Heights Dr, Oakland, MD 21550
    111 Knoll Crest Heights Dr, Oakland, MD 21550
    /33

    $150,000 Sold Dec 17, 2025

    111 Knoll Crest Heights Dr, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 3,504 Sq Ft
    • Built 1971

    Last Sold Summary

    • $43/SF
    • 48 Days On Market

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    111 Knoll Crest Heights Dr, Oakland, MD 21550
    • 0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550
      0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550
      0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550
      /10

      Not Listed For Sale

      0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550

      0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550
  • 62 Crosby Dr, Oakland, MD 21550
    62 Crosby Dr, Oakland, MD 21550
    62 Crosby Dr, Oakland, MD 21550
    /5

    $37,500 Pending

    • Land
    • 0.63 Acre
    • $59,524 per Acre

    62 Crosby Dr, Oakland, MD 21550

    Beautiful building lot in Country Club Acres. Lot 62 and 63 combine for a total 0.629-acre lot and backs up to the Oakland Golf course. Conveniently located close to schools, shopping, restaurants and more. Call today for more info!

    Jon Bell Railey Realty, Inc.

    62 Crosby Dr, Oakland, MD 21550
  • 180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    /43

    $460,000 Sold Oct 24, 2025

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,200 Sq Ft
    • Built 2009

    Last Sold Summary

    • $209/SF
    • 16 Days On Market

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    • 33 Laurel Brook Dr, Oakland, MD 21550
      33 Laurel Brook Dr, Oakland, MD 21550
      33 Laurel Brook Dr, Oakland, MD 21550
      /47

      Est $336,214 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,120 Sq Ft

      33 Laurel Brook Dr, Oakland, MD 21550

      33 Laurel Brook Dr, Oakland, MD 21550
  • 750 Wisp Mountain Rd Unit B, Mc Henry, MD 21541
    750 Wisp Mountain Rd Unit B, Mc Henry, MD 21541
    750 Wisp Mountain Rd Unit B, Mc Henry, MD 21541
    /49

    $675,000 Under Contract

    • 3 Beds
    • 3.5 Baths
    • 3,096 Sq Ft

    750 Wisp Mountain Rd Unit B, Mc Henry, MD 21541

    Nestled at the peak of Wisp Mountain in the Overlook Villas community, you will find this spacious townhome overlooking the beauty of Deep Creek Lake. This exceptional property blends alpine charm with modern luxury, offering a lifestyle as spectacular as the scenery. With three levels of living space, an open floorplan, hardwood flooring, cathedral ceilings, three en-suites, a large loft, and

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    750 Wisp Mountain Rd Unit B, Mc Henry, MD 21541
  • 4960 Hutton Rd, Oakland, MD 21550
    4960 Hutton Rd, Oakland, MD 21550
    4960 Hutton Rd, Oakland, MD 21550
    /32

    $139,000 Sold Aug 15, 2025

    4960 Hutton Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • Built 1971

    Last Sold Summary

    • $129/SF
    • 205 Days On Market

    Current Estimated Value $140,934

    Last Listing Agent Justin Liller Railey Realty, Inc.

    4960 Hutton Rd, Oakland, MD 21550
    • 1200 Mountainview Dr, Oakland, MD 21550
      1200 Mountainview Dr, Oakland, MD 21550
      1200 Mountainview Dr, Oakland, MD 21550
      /64

      Est $1,747,244 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 5,926 Sq Ft

      1200 Mountainview Dr, Oakland, MD 21550

      1200 Mountainview Dr, Oakland, MD 21550
  • 809 N St, Oakland, MD 21550
    809 N St, Oakland, MD 21550
    809 N St, Oakland, MD 21550
    /19

    $65,000

    • 792 Sq Ft

    809 N St, Oakland, MD 21550

    This home needs TLC with the possibility to rebuild on existing foundation if you want to rehab. Buyer to confirm with the county and the town of Mt. Lake Park for rebuilding stipulations. Being sold "As Is". Caution: Entering this property is at your own discretion and responsibility.RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. PROSPECTIVE PURCHASERS AND THEIR

    Kathy Gibson Railey Realty, Inc.

    809 N St, Oakland, MD 21550
  • 297 Woodlands Hill Ln, Oakland, MD 21550
    297 Woodlands Hill Ln, Oakland, MD 21550
    297 Woodlands Hill Ln, Oakland, MD 21550
    /51

    $838,000 Sold Feb 19, 2025

    297 Woodlands Hill Ln, Oakland, MD 21550

    • 5 Beds
    • 5 Baths
    • 3,088 Sq Ft
    • Built 2008

    Last Sold Summary

    • $271/SF
    • 12 Days On Market

    Current Estimated Value $865,503

    Last Listing Agent Roberta McNamara RE/MAX Results

    297 Woodlands Hill Ln, Oakland, MD 21550
    • 19868 Garrett Hwy, Oakland, MD 21550
      19868 Garrett Hwy, Oakland, MD 21550
      19868 Garrett Hwy, Oakland, MD 21550
      /29

      Est $1,825,312 Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 3,860 Sq Ft

      19868 Garrett Hwy, Oakland, MD 21550

      19868 Garrett Hwy, Oakland, MD 21550
  • 40 Fern Loop, Sang Run, MD 21541
    40 Fern Loop, Sang Run, MD 21541
    40 Fern Loop, Sang Run, MD 21541
    /10

    $88,900

    • Land
    • 0.6 Acre
    • $148,167 per Acre

    40 Fern Loop, Sang Run, MD 21541

    Escape to the mountains and relax on your own piece of paradise on "Fern Loop". Build your dream home on this beautiful wooded homesite-"Lot 40" in the peaceful community of Sandy Shores Heights. On the mountaintop with easy access to the Lodestone Golf Course and a convenient hop to Deep Creek Lake, Fork Run, Yough River & Wisp Ski Resort. Ready to build with public water/sewer. Call today to

    Kathy Gibson Railey Realty, Inc.

    40 Fern Loop, Sang Run, MD 21541
  • 202 Deerfield Dr, Oakland, MD 21550
    202 Deerfield Dr, Oakland, MD 21550
    202 Deerfield Dr, Oakland, MD 21550
    /72

    $310,000 Sold Jun 18, 2025

    202 Deerfield Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,720 Sq Ft
    • Built 1987

    Last Sold Summary

    • $114/SF
    • 128 Days On Market

    Current Estimated Value $334,479

    Last Listing Agent Sharon Murray Coldwell Banker Home Town Realty

    202 Deerfield Dr, Oakland, MD 21550

Showing Results 161 - 200, Page 5 of 18

Maryland Garrett County Oakland 21550

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