10,739

Oakland, MD Homes

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  • /46

    $359,000 Coming Soon

    • 3 Beds
    • 3 Baths
    • 1,152 Sq Ft

    552 Black Oak Dr, Oakland, MD 21550

    Looking for a vacation spot or main living, Check out this nicely remolded home in a gated community. 3 bedrooms, 1 1/2 bathrooms, main level laundry room. Great rustic touches . Detached Garage with pellet stove. Yough Mountain Resort is the ultimate mountain escape! Nestled in a quiet, secluded area, this beautifully updated retreat offers modern comfort in a rustic Access to over 50 miles of

    Connie Leprevost Long & Foster Real Estate, Inc.

    552 Black Oak Dr, 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 $116,832

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

    607 K St, Oakland, MD 21550
    • /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

  • /110

    $1,900,000

    • 5 Beds
    • 3.5 Baths
    • 4,619 Sq Ft

    815 Chadderton School Rd, Oakland, MD 21550

    Experience lakefront living at its finest in this exceptional 5-bedroom, 3.5-bath home offering over 4,600 square feet of living space on a private lot of more than one acre. Featuring an incredibly spacious primary suite on the main level, as well as an additional master suite on the second level, this home is ideal for both full-time living and hosting guests. Enjoy breathtaking lake views from

    Kevin Liller Railey Realty, Inc.

    815 Chadderton School Rd, 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 $226,197

    Last Listing Agent Michael Cumerlato Jason Mitchell Group

    10 Laurel Brook Dr, 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.

  • /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
  • /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
    • /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.

  • /39

    $425,000

    • 2 Beds
    • 2.5 Baths
    • 2,960 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
  • /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
    • /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

  • /15

    $75,000 Pending

    • 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
  • /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
    • /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

  • /69

    $2,100,000 Open Sat 10AM - 2PM

    • 5 Beds
    • 5 Baths
    • 4,074 Sq Ft

    1038 S Blakeslee Rd, Oakland, MD 21550

    Welcome to 1038 S Blakeslee Road! A spacious lakefront retreat on Deep Creek Lake offering effortless lakeside living. A Rare opportunity to own in one of Deep Creek’s most sought-after lakeside communities. This five-bedroom, five-bath home sits on a large 1.11-acre level lot with easy access to the water and generous outdoor space for recreation and entertaining. Inside, the home is warm and

    Eric Crawford Taylor Made Deep Creek Real Estate

    1038 S Blakeslee 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
    • /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

  • /17

    $35,000

    • Land
    • 1.92 Acres
    • $18,229 per Acre

    233 Rhododendron Dr, Oakland, MD 21550

    Fantastic opportunity in the gated community of Youghiogheny Mountain Resort. This 1.92-acre lot is perfect for outdoor enthusiasts, offering ATV riding, hunting, fishing, and more. Build your dream home or a recreational retreat. Approved for a 2-bedroom conventional system, with the option to expand using a sand mound system. Located just minutes from Wisp Resort, Deep Creek Lake, Herrington

    Laura Newhall Taylor Made Deep Creek Real Estate

    233 Rhododendron Dr, 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
    • /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

  • /5

    $89,900

    • Land
    • 15.75 Acres
    • $5,708 per Acre

    TBD 15 75 Acres Bethlehem Rd, Oakland, MD 21550

    Tucked away just minutes from town, this 15.75± acre wooded parcel offers a quiet country setting with the privacy many buyers are searching for. Located off Bethlehem Road near the Potomac State Forest, the property features largely level terrain, mature trees, and abundant wildlife—an ideal backdrop for a private residence, weekend retreat, or recreational use. The surrounding area provides

    Thomas Long Railey Realty, Inc.

    TBD 15 75 Acres Bethlehem Rd, 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
    • /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.

  • /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
  • /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
    • /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.

  • /67

    $359,700

    • 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
  • /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
    • /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.

  • /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
  • /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
    • /17

      Est $134,091 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

      • 18% Above List Price
      • $74/SF
      • 63 Days On Market

      Last Sold Price $114,000

      Last Listing Agent Tim Macauley Taylor Made Deep Creek Real Estate

  • /11

    $375,000 Under Contract

    • 3 Beds
    • 2 Baths

    2173 King Wildesen Rd, Oakland, MD 21550

    Experience the beauty of country living in this new construction log home nestled in a peaceful rural setting. Crafted with quality materials, this home offers the perfect blend of modern comfort. Enjoy open-concept living spaces, vaulted ceilings, and windows that allow you to enjoy the pastoral and mountain views. The large front covered porch offers a great space to enjoy family and friends

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    2173 King Wildesen Rd, 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
    • /38

      Est $416,182 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

      • 7% Above List Price
      • $154/SF
      • 2 Days On Market

      Last Sold Price $389,900

      Last Listing Agent Larry Roth Railey Realty, Inc.

  • /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
  • /9

    $25,000 Sold Jan 14, 2026

    18 Hoye Crest Rd, Oakland, MD 21550

    • Land
    • 7.51 Acres
    • $3,329 per Acre

    Last Sold Summary

    • 63 Days On Market

    Last Listing Agent Kellyann Green Railey Realty, Inc.

    18 Hoye Crest Rd, Oakland, MD 21550
    • /56

      Est $664,023 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

      • 1% Below List Price
      • $493/SF
      • 111 Days On Market

      Last Sold Price $667,500

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

  • /20

    $189,000 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 Real Estate

    3395 Fingerboard Rd, Oakland, MD 21550

Showing Results 241 - 280, Page 7 of 18

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