12,257

Homes in ZIP Code 21550

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  • /65

    $150,000 Sold Mar 26, 2026

    506 Roanoke Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1940

    Last Sold Summary

    • 16% Below List Price
    • $111/SF
    • 4 Days On Market

    Current Estimated Value $175,553

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    506 Roanoke Ave, Oakland, MD 21550
    • /87

      Est $453,771 Not Listed For Sale

      2702 Mayhew Inn Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1982
      2702 Mayhew Inn Rd, Oakland, MD 21550

      Last Sold Summary

      • 27% Above List Price
      • $233/SF
      • 9 Days On Market

      Last Sold Price $357,500

      Last Listing Agent Debbie Rogers Charis Realty Group

  • /26

    $475,000

    • Land
    • 1.34 Acres
    • $354,478 per Acre

    LOT 25 Holy Cross Dr, Oakland, MD 21550

    Discover the perfect blend of privacy, prestige, and natural beauty with Lot 25 in The Reserve at Holy Cross—a premier wooded lakefront homesite tucked into a serene private cove on Deep Creek Lake. Boasting 1.34 acres and an impressive 251 feet of lake frontage, this exceptional lot offers the ideal setting to build your dream retreat. Enjoy direct access to the water with up to two boat slips

    Nina Beitzel Railey Realty, Inc.

    LOT 25 Holy Cross Dr, Oakland, MD 21550
  • /20

    $240,000 Sold Jul 11, 2025

    0 Boston Post Rd Unit MDGA2009736, 14, West Oakland, MD 21550

    • Land
    • 0.36 Acre
    • $666,667 per Acre

    Last Sold Summary

    • 6 Days On Market

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    0 Boston Post Rd Unit MDGA2009736, 14, West Oakland, MD 21550
    • /42

      Est $180,400 Not Listed For Sale

      112 B St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1972
      112 B St, Oakland, MD 21550

      Last Sold Summary

      • 3% Above List Price
      • $182/SF
      • 23 Days On Market

      Last Sold Price $175,000

      Last Listing Agent Thomas Long Railey Realty, Inc.

  • /17

    $349,000

    • Land
    • 0.34 Acre
    • $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
  • /39

    $262,500 Sold Feb 05, 2026

    14 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • Built 1989

    Last Sold Summary

    • 3% Below List Price
    • $199/SF
    • 2 Days On Market

    Current Estimated Value $256,363

    Last Listing Agent Larry Smith Railey Realty, Inc.

    14 Laurel Brook Dr, Oakland, MD 21550
    • /64

      Est $178,693 Not Listed For Sale

      608 I St, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,674 Sq Ft
      • Built 1900
      608 I St, Oakland, MD 21550

      Last Sold Summary

      • 10% Above List Price
      • $97/SF
      • 83 Days On Market

      Last Sold Price $163,000

      Last Listing Agent Melissa Long Railey Realty, Inc.

  • /32

    $275,000 Under Contract

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

    6485 Oakland Sang Run Rd, Oakland, MD 21550

    If you are looking for an updated one-level living home with a newer roof, new hot water heater, some new windows, and new flooring, this is a great option. Offering three bedrooms and an unfinished basement with endless possibilities for additional living space, plus a 1-car integrated garage. There are washer/dryer hookups on both the main and lower levels for added convenience. The exterior

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    6485 Oakland Sang Run Rd, Oakland, MD 21550
  • /31

    $70,000 Sold Apr 07, 2025

    99 Black Diamond Ct, Mc Henry, MD 21541

    • Land
    • 0.57 Acre
    • $122,807 per Acre

    Last Sold Summary

    • 29% Below List Price
    • 835 Days On Market

    Last Listing Agent Kathy Gibson Railey Realty, Inc.

    99 Black Diamond Ct, Mc Henry, MD 21541
    • /42

      Est $236,290 Not Listed For Sale

      19 A St, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,920 Sq Ft
      • Built 1973
      19 A St, Oakland, MD 21550

      Last Sold Summary

      • 5% Below List Price
      • $130/SF
      • 152 Days On Market

      Last Sold Price $249,900

      Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

  • /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
  • /41

    $485,000 Sold Sep 22, 2025

    20160 Garrett Hwy Unit D310, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,379 Sq Ft
    • Built 1975

    Last Sold Summary

    • $352/SF
    • 41 Days On Market

    Last Listing Agent Stephanie Smith Select Premium Properties, Inc

    20160 Garrett Hwy Unit D310, Oakland, MD 21550
    • /74

      Est $680,830 Not Listed For Sale

      14 Wanderer Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,355 Sq Ft
      • Built 1973
      14 Wanderer Ln, Oakland, MD 21550

      Last Sold Summary

      • 3% Above List Price
      • $486/SF
      • 1 Day On Market

      Last Sold Price $659,000

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • /20

    $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
  • /37

    $290,000 Sold Jun 05, 2025

    0 Hubbard Rd, Oakland, MD 21550

    • Land
    • 110.17 Acres
    • $2,632 per Acre

    Last Sold Summary

    • 43 Days On Market

    Last Listing Agent Justin Liller Railey Realty, Inc.

    0 Hubbard Rd, Oakland, MD 21550
    • /62

      Est $349,059 Not Listed For Sale

      103 Overlook Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,640 Sq Ft
      • Built 1985
      103 Overlook Dr, Oakland, MD 21550

      Last Sold Summary

      • 8% Above List Price
      • $197/SF
      • 63 Days On Market

      Last Sold Price $322,500

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /10

    $250,000 Pending

    • Land
    • 2.07 Acres
    • $120,773 per Acre

    Lot G Randall Way, Oakland, MD 21550

    Pergin Farm lake access lot with 2 acres and one boat slip. A private wooded setting in one of Deep Creeks most desirable, warm, and inviting locations.

    Russell Bounds Railey Realty, Inc.

    Lot G Randall Way, Oakland, MD 21550
  • /28

    $135,000 Sold Sep 22, 2025

    320 Coolidge Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1900

    Last Sold Summary

    • $188/SF
    • 47 Days On Market

    Current Estimated Value $140,479

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    320 Coolidge Ave, Oakland, MD 21550
    • /73

      Est $991,001 Not Listed For Sale

      375 Ridge View Ct, Oakland, MD 21550

      • 5 Beds
      • 5 Baths
      • 4,160 Sq Ft
      • Built 2006
      375 Ridge View Ct, Oakland, MD 21550

      Last Sold Summary

      • 25% Above List Price
      • $191/SF
      • 17 Days On Market

      Last Sold Price $795,000

      Last Listing Agent Jennifer Stein Homelister, Inc

  • /17

    $37,250

    • 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
  • /16

    $25,000 Sold May 27, 2025

    36 Lehman Ln, Oakland, MD 21550

    • Land
    • 0 Acre

    Last Sold Summary

    • 10 Days On Market

    Last Listing Agent Kellyann Green Railey Realty, Inc.

    36 Lehman Ln, Oakland, MD 21550
    • /38

      Est $290,599 Not Listed For Sale

      644 Silver Knob Rd, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,728 Sq Ft
      • Built 1967
      644 Silver Knob Rd, Oakland, MD 21550

      Last Sold Summary

      • 12% Below List Price
      • $190/SF
      • 9 Days On Market

      Last Sold Price $329,000

      Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

  • /24

    $225,000

    • 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
  • /74

    $915,000 Sold Sep 15, 2025

    186 Thornberry Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,347 Sq Ft
    • Built 1992

    Last Sold Summary

    • $390/SF
    • 48 Days On Market

    Current Estimated Value $1,026,544

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    186 Thornberry Rd, Oakland, MD 21550
    • /57

      Est $370,550 Not Listed For Sale

      840 Smouse Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,863 Sq Ft
      • Built 1980
      840 Smouse Rd, Oakland, MD 21550

      Last Sold Summary

      • 14% Above List Price
      • $174/SF
      • 17 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Daniel Toth EXP Realty, LLC

  • /58

    $234,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,520 Sq Ft

    1021 E High St, Oakland, MD 21550

    Nestled in the convenient High Street neighborhood of Oakland, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this well-maintained 3 Bedroom 2 Bath residence boasts 1,520 sq. ft. above grade finished sq. ft. and a partially finished full basement awaiting your finishing touches. The exterior showcases a welcoming façade with a well-kept yard,

    Andrew Eiswert Railey Realty, Inc.

    1021 E High St, Oakland, MD 21550
  • /22

    $145,800 Sold Apr 11, 2025

    Lot 31 Snowshoe Ct, Mc Henry, MD 21541

    • Land
    • 0.35 Acre
    • $416,571 per Acre

    Last Sold Summary

    • 2 Days On Market

    Last Listing Agent Lana Roby The KW Collective

    Lot 31 Snowshoe Ct, Mc Henry, MD 21541
    • /30

      Est $377,772 Not Listed For Sale

      968 Paradise Heights, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,080 Sq Ft
      • Built 1993
      968 Paradise Heights, Oakland, MD 21550

      Last Sold Summary

      • 28% Above List Price
      • $142/SF
      • 5 Days On Market

      Last Sold Price $295,000

      Last Listing Agent Brian Homberg Taylor Made Deep Creek Real Estate

  • /47

    $299,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,743 Sq Ft

    43 Sloan Tract Rd, Oakland, MD 21550

    Step back to the early days of Deep Creek Lake with this 4-bedroom, 2-bath home full of character and potential. Renovations are underway but unfinished, making this a true handyman or contractor special. Connected to public sewer, the home offers a head start for completing the kitchen and bathrooms and adding custom finishes to create a one-of-a-kind retreat. Enjoy views of Deep Creek Lake and

    Justin Liller Railey Realty, Inc.

    43 Sloan Tract Rd, Oakland, MD 21550
  • /30

    $200,000 Sold Oct 09, 2025

    929 Dogwood Dr, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1973

    Last Sold Summary

    • $174/SF
    • 15 Days On Market

    Current Estimated Value $216,560

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Real Estate

    929 Dogwood Dr, Oakland, MD 21550
    • /105

      Est $422,526 Not Listed For Sale

      1265 Bray School Rd, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 1983
      1265 Bray School Rd, Oakland, MD 21550

      Last Sold Summary

      • 13% Above List Price
      • $195/SF
      • 66 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Susan Bell Railey Realty, Inc.

  • /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
  • /15

    $82,500 Sold Jun 20, 2025

    Lot 112 Biltmore View, Mc Henry, MD 21541

    • Land
    • 0.64 Acre
    • $128,906 per Acre

    Last Sold Summary

    • 33% Below List Price
    • 751 Days On Market

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

    Lot 112 Biltmore View, Mc Henry, MD 21541
    • /56

      Est $521,242 Not Listed For Sale

      11 Trailside Ct, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 2,442 Sq Ft
      • Built 2006
      11 Trailside Ct, Oakland, MD 21550

      Last Sold Summary

      • 10% Above List Price
      • $195/SF
      • 6 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Kathy Gibson Railey Realty, Inc.

  • /11

    $22,500 Pending

    • Land
    • 0.59 Acre
    • $38,136 per Acre

    0 C St, Mountain Lake Park, MD 21550

    .59 acre building lot in Mt Lake Park on C St. Public sewer and water available, electric on site. Partially cleared but mostly wooded setting and backs to small stream.

    Jay Ferguson Taylor Made Deep Creek Real Estate

    0 C St, Mountain Lake Park, MD 21550
  • /70

    $465,000 Sold Aug 12, 2025

    612 Harvey Winters Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,473 Sq Ft
    • Built 2010

    Last Sold Summary

    • $188/SF
    • 6 Days On Market

    Current Estimated Value $485,572

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    612 Harvey Winters Dr, Oakland, MD 21550
    • /95

      Est $1,566,288 Not Listed For Sale

      478 Lake Forest Dr, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 2,688 Sq Ft
      • Built 1996
      478 Lake Forest Dr, Oakland, MD 21550

      Last Sold Summary

      • 5% Above List Price
      • $557/SF
      • 48 Days On Market

      Last Sold Price $1,497,500

      Last Listing Agent Susan Bell Railey Realty, Inc.

  • /26

    $699,000 Under Contract

    • Land
    • 33.93 Acres
    • $20,601 per Acre

    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550

    Incredible Development Opportunity! Almost 34 acres of beautiful grounds zoned Residential/Industrial/Professional (RIP). This parcel would make a beautiful site for a single family or condo/townhome subdivision, business park, or industrial complex. Or, build your dream home with over 33 acres of privacy, yet close to schools, hospital, and downtown Oakland shopping. Public Water on site and

    Justin Liller Railey Realty, Inc.

    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
  • /31

    $745,000 Sold Sep 02, 2025

    200 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,559 Sq Ft
    • Built 2025

    Last Sold Summary

    • $291/SF
    • 16 Days On Market

    Current Estimated Value $775,505

    Last Listing Agent Jonathan Minerick Homecoin.com

    200 Lake Shore Dr, Oakland, MD 21550

Showing Results 281 - 320, Page 8 of 18

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