12,296

Homes in ZIP Code 21550

Section Image
    • /54

      Est $640,846

      Not Listed For Sale

      1385 Mountainview Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,660 Sq Ft
      • Built 2000
      1385 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 26 Days On Market

  • /17

    $349,000

    • Land
    • 14,810 Sq Ft
    • $1,026,471 per Acre

    LOT 12 Boulder Ridge Dr, McHenry, MD 21541

    BOULDER RIDGE #12: A premier lot in this gated community sits atop Wisp Resort. This location provides incredible lake and mountain views and is just minutes away from Deep Creek Lake, acres of state parks, world-class whitewater rafting, and a variety of golf venues for all levels of the sport! With easy access to the Eyeopener and Main Street slopes, you can hop on the trails to enjoy the first

    Kathy Gibson Railey Realty, Inc.

    LOT 12 Boulder Ridge Dr, McHenry, MD 21541
  • /15

    $75,000

    Sold Apr 10, 2026

    60 Gorman St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,488 Sq Ft
    • Built 1920

    Last Sold Summary

    • $50/SF
    • 126 Days On Market

    Current Estimated Value $75,525

    Last Listing Agent Jennifer Jackson Charis Realty Group

    60 Gorman St, Oakland, MD 21550
    • /17

      Est $128,102

      Not Listed For Sale

      2 E Center St, Oakland, MD 21550

      • 2 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1910
      2 E Center St, Oakland, MD 21550

      Last Sold Summary

      • 63 Days On Market

  • /58

    $215,000

    • 2 Beds
    • 1 Bath
    • 1,440 Sq Ft

    2967 Pysell Crosscut Rd, Oakland, MD 21550

    This charming manufactured home offers a delightful blend of comfort and functionality, perfect for those seeking a cozy retreat. With 1,440 square feet of thoughtfully designed living space, this residence features two bedrooms and full bathroom. Step inside to discover a warm and welcoming interior. The combination dining and living area is perfect for entertaining or enjoying quiet evenings at

    Larry Smith Railey Realty, Inc.

    2967 Pysell Crosscut Rd, Oakland, MD 21550
  • /35

    $235,000

    Sold Oct 08, 2025

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550

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

    Last Sold Summary

    • $356/SF
    • 11 Days On Market

    Current Estimated Value $240,781

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

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    • /38

      Est $392,506

      Not Listed For Sale

      29 Crescent Ln, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,536 Sq Ft
      • Built 2007
      29 Crescent Ln, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • /31

    $224,900

    • 1 Bed
    • 1 Bath
    • 1,080 Sq Ft

    206 Mayhew Inn Rd, Oakland, MD 21550

    Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath house blends cozy living with endless potential. The upper level offers a cozy living area, a full kitchen, laundry room, bedroom, and full bath. But the real bonus? A spacious 2-car garage with its own entrance. It is perfect for a workshop, extra storage, or even a rental opportunity. With separate

    Jay Quinn Taylor-Made Deep Creek Real Estate, LLC

    206 Mayhew Inn Rd, Oakland, MD 21550
  • /93

    $785,000

    Sold Jun 01, 2026

    1001 Sutter Ln, Oakland, MD 21550

    • 5 Beds
    • 6 Baths
    • 6,550 Sq Ft
    • Built 2000

    Last Sold Summary

    • $120/SF
    • 172 Days On Market

    Current Estimated Value $787,171

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1001 Sutter Ln, Oakland, MD 21550
    • /56

      Est $672,180

      Not Listed For Sale

      148 Wanderer Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,355 Sq Ft
      • Built 1970
      148 Wanderer Ln, Oakland, MD 21550

      Last Sold Summary

      • 111 Days On Market

  • /45

    $149,900

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    115 Woodmont Ln, Oakland, MD 21550

    Set on 1 acre just minutes from town, this 3-bedroom, 1 bath home is full of potential and ready for its next chapter. Whether you're searching for an affordable starter home or your next renovation project, this property offers a solid opportunity to create something special. Features include a spacious screened porch, functional floor plan, and a full basement with ample storage and workspace.

    Mike Fenton Railey Realty, Inc.

    115 Woodmont Ln, Oakland, MD 21550
  • /17

    $18,000

    Sold Nov 14, 2025

    Lots 59 & 60 Cedar Ln, Oakland, MD 21550

    • Land
    • 42,688 Sq Ft
    • $18,367 per Acre

    Last Sold Summary

    • 17 Days On Market

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

    Lots 59 & 60 Cedar Ln, Oakland, MD 21550
    • /82

      Est $1,698,190

      Not Listed For Sale

      1597 Lake Shore Dr, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 1,904 Sq Ft
      • Built 2006
      1597 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • /61

    $185,000

    • 3 Beds
    • 1.5 Baths
    • 1,170 Sq Ft

    729 E Oak St, Oakland, MD 21550

    Great, affordable starter home located in Oakland with public water and sewer, one car detached garage, hot water natural gas heat. Two bedroom and full bath on second level and possible third bedroom on main level with 1/2 bath. Cellar basement with mechanicals. Washer and Dryer hookups, washer/dryer convey, are located on the back enclosed porch which has electric baseboard heat. Enclosed front

    Kevin Liller Railey Realty, Inc.

    729 E Oak St, Oakland, MD 21550
  • /34

    $459,000

    Sold Nov 25, 2025

    50 Village Dr Unit 7, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 2006

    Last Sold Summary

    • $455/SF
    • 17 Days On Market

    Current Estimated Value $430,829

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    50 Village Dr Unit 7, Oakland, MD 21550
    • /29

      Est $173,584

      Not Listed For Sale

      216 E Center St, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,472 Sq Ft
      • Built 1932
      216 E Center St, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • /55

    $329,900

    • 1 Bed
    • 1 Bath
    • 496 Sq Ft

    565 Glendale Rd Unit 125, Oakland, MD 21550

    Wake up to the lake at your doorstep. This ground-level, end-unit condo offers true lakefront living with unbeatable access to everything Deep Creek Lake has to offer. Enjoy effortless days on the water, then relax with on-site amenities including a fitness room, sauna, game room, and expansive lakeside decking. Walk to Dutch’s at Silver Tree, The Harbor Bar, and the marina for dining, drinks,

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 125, Oakland, MD 21550
  • /50

    $559,250

    Sold Sep 02, 2025

    285 Winding Trail Ln Unit 10A, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2008

    Last Sold Summary

    • $169/SF
    • 62 Days On Market

    Current Estimated Value $561,066

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    • /33

      Est $416,570

      Not Listed For Sale

      1012 Hemlock Cir, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,590 Sq Ft
      • Built 2002
      1012 Hemlock Cir, Oakland, MD 21550

      Last Sold Summary

      • 35 Days On Market

  • /21

    $160,000

    • Land
    • 10.1 Acres
    • $15,842 per Acre

    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550

    Over 10 acres ready for developing off Dennett Rd. and Oakland Ave. Can be subdivided or could be large parcel to build your dream home, privacy off main streets with 3 separate entrances connecting to town roads. Engineered drawings for subdivision with grading permit in place at time of survey, is available and will be transferred with sale. (Potential up to 20 lots) Public sewar & water can be

    Julie Mead The KW Collective

    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550
  • /13

    $155,000

    Sold Jan 08, 2026

    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550

    • Land
    • 31,363 Sq Ft
    • $215,278 per Acre

    Last Sold Summary

    • 16 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550
    • /7

      Est $300,927

      Not Listed For Sale

      1517 Upperman Rd, Oakland, MD 21550

      • 1 Bed
      • 1 Bath
      • 530 Sq Ft
      • Built 2024
      1517 Upperman Rd, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

  • /24

    $225,000

    $21K PRICE DROP
    • Land
    • 1.33 Acres
    • $169,173 per Acre

    Lot 94 Wisp Adventure Rd, McHenry, MD 21541

    Oversized mountain-view lot in North Camp Ridge, ideally located just minutes from Wisp Resort amenities. This centrally located parcel offers the perfect setting to build your custom vacation home or mountain retreat. Enjoy expansive, unobstructed mountain views and the privacy that comes with a generously sized lot, while still being close to skiing, golf, hiking, lake activities, dining, and

    Larry Smith Railey Realty, Inc.

    Lot 94 Wisp Adventure Rd, McHenry, MD 21541
  • /54

    $550,000

    Sold Aug 29, 2025

    710 Hunters Ridge Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft
    • Built 2007

    Last Sold Summary

    • $317/SF
    • 70 Days On Market

    Current Estimated Value $540,866

    Last Listing Agent Andrew Orr The KW Collective

    710 Hunters Ridge Dr, Oakland, MD 21550
    • /52

      Est $230,555

      Not Listed For Sale

      1865 Garrett Rd, Oakland, MD 21550

      • 4 Beds
      • 1 Bath
      • 1,144 Sq Ft
      • Built 1994
      1865 Garrett Rd, Oakland, MD 21550

      Last Sold Summary

      • 19 Days On Market

  • /17

    $37,250

    $5K PRICE DROP Pending
    • Land
    • 3.03 Acres
    • $12,294 per Acre

    Lot 1 Cherrywood Dr, Oakland, MD 21550

    ****NOW ONLY $37,250!! Discover the perfect blend of space, privacy, and convenience with this 3.03 acre lot, a short drive from downtown Oakland, Deep Creek Lake, Potomac State Forest and Garrett State Forest! With a 5-bedroom perc on file, this property is ready for your dream home. This beautiful property is located in Cherrywood Ridge Subdivision, with only 7 lots in the community.

    Amy Skipper Railey Realty, Inc.

    Lot 1 Cherrywood Dr, Oakland, MD 21550
  • /78

    $760,000

    Sold Sep 15, 2025

    61 Par Way, Mc Henry, MD 21541

    • 4 Beds
    • 3.5 Baths
    • 2,218 Sq Ft
    • Built 2021

    Last Sold Summary

    • $343/SF
    • 5 Days On Market

    Current Estimated Value $791,498

    Last Listing Agent Elizabeth Ware Railey Realty, Inc.

    61 Par Way, Mc Henry, MD 21541
    • /21

      Est $273,565

      Not Listed For Sale

      17 Laurel Brook Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,840 Sq Ft
      • Built 1991
      17 Laurel Brook Dr, Oakland, MD 21550

      Last Sold Summary

      • 171 Days On Market

  • /58

    $234,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,520 Sq Ft

    1021 E High St, Oakland, MD 21550

    ***BACK ON THE MARKET, don't miss this one a second time! Welcome home to this solid, ranch style home on one of Oakland's most convenient streets. Built in 1954, this 3-bedroom, 2-bath home delivers 1,520 sq ft of comfortable living, plus a partially finished full basement ready for your vision, whether that's a rec room, home office, or extra storage. The metal roof means peace of mind for

    Jeremy Cunningham Railey Realty, Inc.

    1021 E High St, Oakland, MD 21550
  • /20

    $200,000

    Sold Feb 06, 2026

    123 Mountainview Ct, Oakland, MD 21550

    • Land
    • 1.69 Acres
    • $118,343 per Acre

    Last Sold Summary

    • 72 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    123 Mountainview Ct, Oakland, MD 21550
    • /70

      Est $1,661,983

      Not Listed For Sale

      22 Duck Cove Rd, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 1,964 Sq Ft
      • Built 1960
      22 Duck Cove Rd, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /19

    $295,000

    • Land
    • 8.48 Acres
    • $34,788 per Acre

    26 Green Brier Rd, Oakland, MD 21550

    8.48± acres offering excellent commercial or residential potential. Property features an existing well and septic system, with easy access and outstanding visibility. Conveniently located just minutes from the Oakland city limits outside of Zoning Districts. Ideal opportunity for development or investment.

    Rich Orr Railey Realty, Inc.

    26 Green Brier Rd, Oakland, MD 21550
  • /51

    $660,000

    Sold Jan 30, 2026

    155 Basswood Way, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,792 Sq Ft
    • Built 2003

    Last Sold Summary

    • $236/SF
    • 268 Days On Market

    Current Estimated Value $640,242

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    155 Basswood Way, Oakland, MD 21550
    • /41

      Est $337,865

      Not Listed For Sale

      139 Hunters Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,240 Sq Ft
      • Built 1991
      139 Hunters Dr, Oakland, MD 21550

      Last Sold Summary

      • 45 Days On Market

  • /56

    $325,000

    $34K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,563 Sq Ft

    17921 Garrett Hwy, Oakland, MD 21550

    Charming and well-maintained, this 4-bedroom, 1.5-bath traditional home offers the perfect combination of comfort, character, and convenience. Built in 1952 and thoughtfully cared for, the home features beautifully refinished hardwood floors, inviting built-ins, and a cozy living room with a functional wood burner. With over 1,500 square feet of living space, the spacious layout includes an

    Michelle Clark Taylor-Made Deep Creek Real Estate, LLC

    17921 Garrett Hwy, Oakland, MD 21550
  • /37

    $250,000

    Sold Dec 31, 2025

    511 E Green St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft
    • Built 1924

    Last Sold Summary

    • $133/SF
    • 176 Days On Market

    Current Estimated Value $247,685

    Last Listing Agent Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    511 E Green St, Oakland, MD 21550
    • /49

      Est $908,258

      Not Listed For Sale

      158 Silver Tree Ln, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 2,250 Sq Ft
      • Built 2003
      158 Silver Tree Ln, Oakland, MD 21550

      Last Sold Summary

      • 79 Days On Market

  • /64

    $945,000

    $50K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,734 Sq Ft

    94 Sandy View Ct, Mc Henry, MD 21541

    Perched atop Wisp Mountain in the Lago Vista community you’ll find this wonderful 5-bedroom retreat “Big & Boulder”. This exceptional five-bedroom home blends rugged natural beauty with refined comfort. The 3-levels offer an open floorplan and two gathering areas, with a gas fireplace on the main level and gaming tables on the lower level. Massive native boulders frame the property, creating a

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

    94 Sandy View Ct, Mc Henry, MD 21541
  • /98

    $590,000

    Sold Oct 10, 2025

    2719 Broadford Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 4,253 Sq Ft
    • Built 1984

    Last Sold Summary

    • $139/SF
    • 168 Days On Market

    Current Estimated Value $575,993

    Last Listing Agent Rich Orr Railey Realty, Inc.

    2719 Broadford Rd, Oakland, MD 21550
    • /83

      Est $2,284,410

      Not Listed For Sale

      320 Lake Forest Dr, Oakland, MD 21550

      • 6 Beds
      • 4.5 Baths
      • 2,363 Sq Ft
      • Built 1997
      320 Lake Forest Dr, Oakland, MD 21550

      Last Sold Summary

      • 111 Days On Market

Showing Results 321 - 360, Page 9 of 18

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