10,731

Oakland, MD Homes

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  • 26 Green Brier Rd, Oakland, MD 21550
    26 Green Brier Rd, Oakland, MD 21550
    26 Green Brier Rd, Oakland, MD 21550
    /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
  • 94 Meadow Ct, Oakland, MD 21550
    94 Meadow Ct, Oakland, MD 21550
    94 Meadow Ct, Oakland, MD 21550
    /74

    $664,500 Sold Oct 17, 2025

    94 Meadow Ct, Oakland, MD 21550

    • 3 Beds
    • 4 Baths
    • 2,460 Sq Ft
    • Built 1999

    Last Sold Summary

    • $270/SF
    • 54 Days On Market

    Current Estimated Value $665,958

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

    94 Meadow Ct, Oakland, MD 21550
    • 314 Allegheny Dr, Oakland, MD 21550
      314 Allegheny Dr, Oakland, MD 21550
      314 Allegheny Dr, Oakland, MD 21550
      /48

      Est $340,075 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 1,750 Sq Ft

      314 Allegheny Dr, Oakland, MD 21550

      314 Allegheny Dr, Oakland, MD 21550
  • 506 Roanoke Ave, Oakland, MD 21550
    506 Roanoke Ave, Oakland, MD 21550
    506 Roanoke Ave, Oakland, MD 21550
    /65

    $179,000

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

    506 Roanoke Ave, Oakland, MD 21550

    Charming and well-maintained 3-bedroom, 1-bath home situated on an oversized lot in a convenient Loch Lynn location. This property features a detached two-car garage offering plenty of storage or workspace, along with recent upgrades that add to the home’s comfort and appeal. The spacious yard and covered porches provide room to relax, garden, or expand outdoor living. With a solid layout,

    Zach Wesolowski Railey Realty, Inc.

    506 Roanoke Ave, Oakland, MD 21550
  • 603 Oak St, Oakland, MD 21550
    603 Oak St, Oakland, MD 21550
    603 Oak St, Oakland, MD 21550
    /42

    $175,000 Sold May 09, 2025

    603 Oak St, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 1965

    Last Sold Summary

    • $146/SF
    • 49 Days On Market

    Current Estimated Value $178,948

    Last Listing Agent Andrew Orr The KW Collective

    603 Oak St, Oakland, MD 21550
    • 34 Hooppole Ct, Oakland, MD 21550
      34 Hooppole Ct, Oakland, MD 21550
      34 Hooppole Ct, Oakland, MD 21550
      /87

      Est $769,907 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,355 Sq Ft

      34 Hooppole Ct, Oakland, MD 21550

      34 Hooppole Ct, Oakland, MD 21550
  • 0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    /26

    $699,000

    • 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
  • 607 K St, Oakland, MD 21550
    607 K St, Oakland, MD 21550
    607 K St, Oakland, MD 21550
    /21

    $115,000 Sold Nov 03, 2025

    607 K St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • Built 1920

    Last Sold Summary

    • $86/SF
    • 213 Days On Market

    Current Estimated Value $114,583

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

    607 K St, Oakland, MD 21550
    • 2702 Mayhew Inn Rd, Oakland, MD 21550
      2702 Mayhew Inn Rd, Oakland, MD 21550
      2702 Mayhew Inn Rd, Oakland, MD 21550
      /87

      Est $464,324 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft

      2702 Mayhew Inn Rd, Oakland, MD 21550

      2702 Mayhew Inn Rd, Oakland, MD 21550
  • Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550
    Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550
    Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550
    /11

    $5,000

    • Land
    • 0.96 Acre
    • $5,208 per Acre

    Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550

    Discover the perfect mountain getaway in Yough Mountain Resort, a gated community nestled in the scenic mountains of western Maryland, just minutes from Deep Creek Lake. This amenity-rich community offers an outdoor enthusiast’s dream with ATV and snowmobile trails, Yough River access, nearby state parks, hunting opportunities, plus a playground and pavilion area for gathering and relaxing.

    Mike Kennedy Railey Realty, Inc.

    Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550
  • 10 Laurel Brook Dr, Oakland, MD 21550
    10 Laurel Brook Dr, Oakland, MD 21550
    10 Laurel Brook Dr, Oakland, MD 21550
    /39

    $210,000 Sold Aug 01, 2025

    10 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • Built 1989

    Last Sold Summary

    • 421 Days On Market

    Current Estimated Value $228,451

    Last Listing Agent Michael Cumerlato Jason Mitchell Group

    10 Laurel Brook Dr, Oakland, MD 21550
    • 214 I St, Oakland, MD 21550
      214 I St, Oakland, MD 21550
      214 I St, Oakland, MD 21550
      /77

      Est $181,260 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,852 Sq Ft

      214 I St, Oakland, MD 21550

      214 I St, Oakland, MD 21550
  • lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
    /15

    $39,000

    • Land
    • 2.57 Acres
    • $15,175 per Acre

    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550

    2 lots (7 & 8) totaling 2.57 acres, on gently sloping wooded area. Nestled between Cannan Valley & Deep Creek Lake, this promises to be a perfect blend of convenience and tranquility. Nature surrounds you - the perfect spot for a cozy cabin! Call agent for more information!

    Julie Mead The KW Collective

    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
  • 14 Laurel Brook Dr, Oakland, MD 21550
    14 Laurel Brook Dr, Oakland, MD 21550
    14 Laurel Brook Dr, Oakland, MD 21550
    /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

    Last Listing Agent Larry Smith Railey Realty, Inc.

    14 Laurel Brook Dr, Oakland, MD 21550
    • 39 Laurel Brook Dr, Oakland, MD 21550
      39 Laurel Brook Dr, Oakland, MD 21550
      39 Laurel Brook Dr, Oakland, MD 21550
      /32

      Est $314,973 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths

      39 Laurel Brook Dr, Oakland, MD 21550

      39 Laurel Brook Dr, Oakland, MD 21550
  • 232 Jeffrey Ln Unit 33, Oakland, MD 21550
    232 Jeffrey Ln Unit 33, Oakland, MD 21550
    232 Jeffrey Ln Unit 33, Oakland, MD 21550
    /39

    $425,000

    • 2 Beds
    • 2.5 Baths
    • 1,301 Sq Ft

    232 Jeffrey Ln Unit 33, Oakland, MD 21550

    Turn-key and fully furnished, this beautifully maintained duplex offers the perfect blend of comfort, views, and location in the heart of Deep Creek Lake. Featuring an open, inviting floor plan, the home is designed for both everyday enjoyment and effortless entertaining. The main level features a spacious living area with a stone-surround fireplace, abundant natural light, and a seamless flow to

    Sean Brink Samson Properties

    232 Jeffrey Ln Unit 33, Oakland, MD 21550
  • 20160 Garrett Hwy Unit D310, Oakland, MD 21550
    20160 Garrett Hwy Unit D310, Oakland, MD 21550
    20160 Garrett Hwy Unit D310, 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
    • 608 I St, Oakland, MD 21550
      608 I St, Oakland, MD 21550
      608 I St, Oakland, MD 21550
      /64

      Est $178,304 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,674 Sq Ft

      608 I St, Oakland, MD 21550

      608 I St, Oakland, MD 21550
  • 60 Gorman St, Oakland, MD 21550
    60 Gorman St, Oakland, MD 21550
    60 Gorman St, Oakland, MD 21550
    /15

    $75,000

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

    60 Gorman St, Oakland, MD 21550

    Bring you vision to this 3-bedroom, 1 bath home right outside of Oakland, Maryland. Features a spacious living room, updated kitchen and a cozy front deck. With a little love and final touches, the property could shine again - ideal for a renovation project or investment opportunity. There is a nice yard and off street parking. Great opportunity for buyers looking to invest or customize a home to

    Jennifer Jackson Charis Realty Group

    60 Gorman St, Oakland, MD 21550
  • 0 Hubbard Rd, Oakland, MD 21550
    0 Hubbard Rd, Oakland, MD 21550
    0 Hubbard Rd, 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
    • 19 A St, Oakland, MD 21550
      19 A St, Oakland, MD 21550
      19 A St, Oakland, MD 21550
      /42

      Est $251,465 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,920 Sq Ft

      19 A St, Oakland, MD 21550

      19 A St, Oakland, MD 21550
  • 0 Bethlehem Rd, Oakland, MD 21550
    0 Bethlehem Rd, Oakland, MD 21550
    0 Bethlehem Rd, Oakland, MD 21550
    /5

    $79,000

    • Land
    • 8.73 Acres
    • $9,049 per Acre

    0 Bethlehem Rd, Oakland, MD 21550

    LOT A= 8.73 acre parcel, located off Bethlehem Rd, in Western Maryland! Separate lot B (7.02 acres) behind this lot, also for sale. Near Potomac State Forest, this country setting, offers level land, perfect for building a home or if you are looking for a recreational outdoor property, this is a perfect spot for your adventures. Located outside the town of Oakland, just 8 mins away from schools,

    Thomas Long Railey Realty, Inc.

    0 Bethlehem Rd, Oakland, MD 21550
  • 320 Coolidge Ave, Oakland, MD 21550
    320 Coolidge Ave, Oakland, MD 21550
    320 Coolidge Ave, 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 $135,978

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    320 Coolidge Ave, Oakland, MD 21550
    • 14 Wanderer Ln, Oakland, MD 21550
      14 Wanderer Ln, Oakland, MD 21550
      14 Wanderer Ln, Oakland, MD 21550
      /74

      Est $747,188 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,355 Sq Ft

      14 Wanderer Ln, Oakland, MD 21550

      14 Wanderer Ln, Oakland, MD 21550
  • 5202 Hutton Rd, Oakland, MD 21550
    5202 Hutton Rd, Oakland, MD 21550
    5202 Hutton Rd, Oakland, MD 21550
    /50

    $239,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,199 Sq Ft

    5202 Hutton Rd, Oakland, MD 21550

    First time homebuyer alert!! Charming ranch-style home offering 3 bedrooms, 1 full bath (jetted tub!), and loads of potential! This one-level home sits on over 12 beautiful acres with mature fruit trees, providing plenty of space for outdoor activities, gardening, or even future expansion. The attached garage adds convenience, and the layout makes for easy, comfortable living. Located just

    Nina Beitzel Railey Realty, Inc.

    5202 Hutton Rd, Oakland, MD 21550
  • 36 Lehman Ln, Oakland, MD 21550
    36 Lehman Ln, Oakland, MD 21550
    36 Lehman Ln, 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
    • 103 Overlook Dr, Oakland, MD 21550
      103 Overlook Dr, Oakland, MD 21550
      103 Overlook Dr, Oakland, MD 21550
      /62

      Est $347,958 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,640 Sq Ft

      103 Overlook Dr, Oakland, MD 21550

      103 Overlook Dr, Oakland, MD 21550
  • 209 Glendale Rd, Oakland, MD 21550
    209 Glendale Rd, Oakland, MD 21550
    209 Glendale Rd, Oakland, MD 21550
    /89

    $2,100,000

    • 6 Beds
    • 4.5 Baths
    • 3,882 Sq Ft

    209 Glendale Rd, Oakland, MD 21550

    If you're in the market for location, convenience, and rental income, this inviting 6 Bedroom 4.5 bath Lakefront home is calling for you! Located in the heart of the action on Deep Creek Lake, the 3 level chateau has been updated and upgraded both inside and out. Restaurants, the movie theatre, shopping and Deep Creek Lake State Park are all within walking distance. Offering an open layout with

    Bill Weissgerber Railey Realty, Inc.

    209 Glendale Rd, Oakland, MD 21550
  • 186 Thornberry Rd, Oakland, MD 21550
    186 Thornberry Rd, Oakland, MD 21550
    186 Thornberry Rd, Oakland, MD 21550
    /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 $954,295

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

    186 Thornberry Rd, Oakland, MD 21550
    • 375 Ridge View Ct, Oakland, MD 21550
      375 Ridge View Ct, Oakland, MD 21550
      375 Ridge View Ct, Oakland, MD 21550
      /73

      Est $966,161 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 4,160 Sq Ft

      375 Ridge View Ct, Oakland, MD 21550

      375 Ridge View Ct, Oakland, MD 21550
  • 723 Kings Ct, Oakland, MD 21550
    723 Kings Ct, Oakland, MD 21550
    723 Kings Ct, Oakland, MD 21550
    /67

    $380,000

    • 4 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    723 Kings Ct, Oakland, MD 21550

    "Charming two-story home situated on a beautiful .292-acre level lot in a prime location (Kings Hills Estates) Enjoy the perfect blend of comfort and convenience with spacious living areas, a serene yard ideal for outdoor entertaining. Ideally located near a top-rate Hospital, popular shopping destinations, and just minutes to Broadford Lake. Whether you're enjoying a day on the water or running

    Debra Beitzel Long & Foster Real Estate, Inc.

    723 Kings Ct, Oakland, MD 21550
  • 929 Dogwood Dr, Oakland, MD 21550
    929 Dogwood Dr, Oakland, MD 21550
    929 Dogwood Dr, 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 $212,871

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Vacations & Sales

    929 Dogwood Dr, Oakland, MD 21550
    • 644 Silver Knob Rd, Oakland, MD 21550
      644 Silver Knob Rd, Oakland, MD 21550
      644 Silver Knob Rd, Oakland, MD 21550
      /38

      Est $325,591 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,728 Sq Ft

      644 Silver Knob Rd, Oakland, MD 21550

      644 Silver Knob Rd, Oakland, MD 21550
  • 3501 George Washington Hwy, Oakland, MD 21550
    3501 George Washington Hwy, Oakland, MD 21550
    3501 George Washington Hwy, Oakland, MD 21550
    /22

    $95,000 Under Contract

    • Land
    • 2.86 Acres
    • $33,217 per Acre

    3501 George Washington Hwy, Oakland, MD 21550

    Welcome to 3501 George Washington Highway, a premier property containing 2.86 acres of prime land perfect for personal, or commercial storage purposes. The property features a recently renovated garage with four spacious bays, providing versatility for automotive, storage, or workshop purposes. The large gravel storage lot and concrete pad are ideal for all outdoor storage needs. Two metal

    Zach Wesolowski Railey Realty, Inc.

    3501 George Washington Hwy, Oakland, MD 21550
  • 612 Harvey Winters Dr, Oakland, MD 21550
    612 Harvey Winters Dr, Oakland, MD 21550
    612 Harvey Winters Dr, Oakland, 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 $473,226

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    612 Harvey Winters Dr, Oakland, MD 21550
    • 840 Smouse Rd, Oakland, MD 21550
      840 Smouse Rd, Oakland, MD 21550
      840 Smouse Rd, Oakland, MD 21550
      /57

      Est $335,060 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,863 Sq Ft

      840 Smouse Rd, Oakland, MD 21550

      840 Smouse Rd, Oakland, MD 21550
  • 1 Lowes Dr, Oakland, MD 21550
    1 Lowes Dr, Oakland, MD 21550
    1 Lowes Dr, Oakland, MD 21550
    /15

    $175,000

    • Land
    • 1.6 Acres
    • $109,375 per Acre

    1 Lowes Dr, Oakland, MD 21550

    Lot #1. is 1.6 Acre Cleared Commercial Site in Lowe's Subdivision. Public Utilities and Natural gas to the site. Paved street access and High Traffic Zone. Plat available.

    Rich Orr Railey Realty, Inc.

    1 Lowes Dr, Oakland, MD 21550
  • 200 Lake Shore Dr, Oakland, MD 21550
    200 Lake Shore Dr, Oakland, MD 21550
    200 Lake Shore Dr, 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 $759,504

    Last Listing Agent Jonathan Minerick Homecoin.com

    200 Lake Shore Dr, Oakland, MD 21550
    • 968 Paradise Heights, Oakland, MD 21550
      968 Paradise Heights, Oakland, MD 21550
      968 Paradise Heights, Oakland, MD 21550
      /30

      Est $389,040 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,080 Sq Ft

      968 Paradise Heights, Oakland, MD 21550

      968 Paradise Heights, Oakland, MD 21550
  • 3395 Fingerboard Rd, Oakland, MD 21550
    3395 Fingerboard Rd, Oakland, MD 21550
    3395 Fingerboard Rd, Oakland, MD 21550
    /20

    $199,000 New Construction

    • 4 Beds
    • 2 Baths

    3395 Fingerboard Rd, Oakland, MD 21550

    6+ acre homestead with a 4BR, 2BA home currently under construction. Sellers plans have changed and they will not be finishing the house. The structure is under roof, mostly framed-in with building materials on site that will convey with the sale. A new well has been drilled and septic permit is approved for 4BRs. Located just outside of town limits, this parcel has impressive mountain views and

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    3395 Fingerboard Rd, Oakland, MD 21550

Showing Results 241 - 280, Page 7 of 18

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