10,549

Oakland, MD Homes

Section Image
    • /30

      Est $362,895

      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

      • 5 Days On Market

      Last Listing Agent Brian Homberg Taylor-Made Deep Creek Real Estate, LLC

  • /7

    $39,500

    $3K PRICE DROP
    • Land
    • 1.05 Acres
    • $37,619 per Acre

    0 Maple Del Ln, Oakland, MD 21550

    Lot 6 Maple Del is a mostly wooded , 1.05 acre lot near the western parts of Deep Creek Lake, Red Run cove and centrally located off Mayhew Inn Rd. There is a small stream running through the property and huge boulders strewn throughout, making it a fantastic setting for a wooded retreat. Incredible location near state parks and Deep Creek Lake area amenities. Public sewer available with sewer

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    0 Maple Del Ln, Oakland, MD 21550
  • /71

    $912,500

    Sold Dec 05, 2025

    78 Mountainside Ct, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,492 Sq Ft
    • Built 2002

    Last Sold Summary

    • $261/SF
    • 61 Days On Market

    Current Estimated Value $955,513

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

    78 Mountainside Ct, Oakland, MD 21550
    • /105

      Est $398,806

      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

      • 66 Days On Market

      Last Listing Agent Susan Bell Railey Realty, Inc.

  • /46

    $349,000

    $10K PRICE DROP
    • 3 Beds
    • 1.5 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
  • /82

    $785,000

    Sold Jun 03, 2026

    53 Meadow Ct, Oakland, MD 21550

    • 4 Beds
    • 6 Baths
    • 3,630 Sq Ft
    • Built 2005

    Last Sold Summary

    • 5% Below List Price
    • $216/SF
    • 6 Days On Market

    Current Estimated Value $793,238

    Last Listing Agent Jon Bell Railey Realty, Inc.

    53 Meadow Ct, Oakland, MD 21550
    • /35

      Est $288,725

      Not Listed For Sale

      506 Cedar Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1979
      506 Cedar Ln, Oakland, MD 21550

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

  • /29

    $339,900

    $29K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    531 Glendale Rd Unit B302, Oakland, MD 21550

    Experience effortless lakeside living at its finest in this spacious 2-bedroom, 1-bath unit in Silver Tree Suites—one of the largest units in the complex! This beautifully designed unit features an open floorplan centered around a cozy fireplace, perfect for relaxing after a day on the lake. A generous loft area creates a distinct separation between living and sleeping spaces, offering

    Larry Smith Railey Realty, Inc.

    531 Glendale Rd Unit B302, Oakland, MD 21550
  • /87

    $867,500

    Sold Feb 20, 2026

    340 Grandview Dr, Oakland, MD 21550

    • 6 Beds
    • 4 Baths
    • 2,536 Sq Ft
    • Built 2003

    Last Sold Summary

    • $342/SF
    • 88 Days On Market

    Current Estimated Value $930,076

    Last Listing Agent Jon Bell Railey Realty, Inc.

    340 Grandview Dr, Oakland, MD 21550
    • /95

      Est $1,517,102

      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

      • 48 Days On Market

      Last Listing Agent Susan Bell 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
  • /37

    $382,500

    Sold Feb 27, 2026

    15 Village Dr Unit 1, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • Built 2004

    Last Sold Summary

    • 408 Days On Market

    Current Estimated Value $397,583

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    15 Village Dr Unit 1, Oakland, MD 21550
    • /54

      Est $661,967

      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

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /51

    $399,900

    $35K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,406 Sq Ft

    511 Hilltop Rd, Oakland, MD 21550

    Tucked away on a quiet cul-de-sac in the desirable Royal Charlotte community, this stunning 4-bedroom, 3-bathroom home is the kind of property you'll fall in love with the moment you arrive. Surrounded by the beauty and tranquility of the mountains and accessed by county-maintained roads, this impeccably maintained home showcases pride of ownership throughout. From the expansive Trex decking that

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    511 Hilltop Rd, Oakland, MD 21550
  • /76

    $420,000

    Sold Oct 15, 2025

    783 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,971 Sq Ft
    • Built 2002

    Last Sold Summary

    • $213/SF
    • 122 Days On Market

    Current Estimated Value $476,076

    Last Listing Agent Larry Smith Railey Realty, Inc.

    783 Mountainview Dr, Oakland, MD 21550
    • /17

      Est $136,232

      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

      Last Listing Agent Tim Macauley Taylor-Made Deep Creek Real Estate, LLC

  • /5

    $18,000

    • Land
    • 27,007 Sq Ft
    • $29,032 per Acre

    13 Birchwood Dr, Oakland, MD 21550

    Discover your own mountain escape in the gated community of Youghiogheny Mountain Resort! This 0.62-acre lot is perfect for building a dream home or weekend retreat, surrounded by miles of ATV trails, hunting, and fishing. Ideally located near Wisp Resort, Deep Creek Lake, Herrington Manor State Park, and Swallow Falls State Park, you’ll enjoy year-round outdoor adventure. Approved for a sand

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    13 Birchwood Dr, Oakland, MD 21550
  • /35

    $380,000

    Sold Sep 26, 2025

    20160 Garrett Hwy Unit G 509, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1974

    Last Sold Summary

    • $594/SF
    • 24 Days On Market

    Current Estimated Value $383,168

    Last Listing Agent Tim Macauley Taylor-Made Deep Creek Real Estate, LLC

    20160 Garrett Hwy Unit G 509, Oakland, MD 21550
    • /38

      Est $406,990

      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

      Last Listing Agent Larry Roth Railey Realty, Inc.

  • /72

    $569,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,654 Sq Ft

    355 Markwood Dr, Oakland, MD 21550

    Fall in love with the perfect blend of comfort, privacy, and outdoor adventure in this beautifully maintained home nestled on 3.67 wooded acres overlooking scenic Meadow Lake. Thoughtfully designed for easy living, this 3-bedroom, 2.5-bath home features an open floor plan where the spacious great room flows seamlessly into a beautifully updated kitchen complete with granite countertops, making it

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    355 Markwood Dr, Oakland, MD 21550
  • /50

    $239,000

    Sold Feb 11, 2026

    5202 Hutton Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,199 Sq Ft
    • Built 1950

    Last Sold Summary

    • $199/SF
    • 149 Days On Market

    Current Estimated Value $246,742

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    5202 Hutton Rd, Oakland, MD 21550
    • /56

      Est $692,440

      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

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

  • /24

    $18,000

    • Land
    • 20,473 Sq Ft
    • $38,298 per Acre

    27 Gobbler Run Rd, Oakland, MD 21550

    Build your ideal mountain retreat in the gated community of Youghiogheny Mountain Resort! This level 0.47-acre lot offers an easy build site and is Health Department approved for a shallow trench gravity septic system. Enjoy access to ATV trails, hunting, and fishing, all just minutes from Wisp Resort, Deep Creek Lake, and Swallow Falls State Park. Whether you're planning a full-time home or

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    27 Gobbler Run Rd, Oakland, MD 21550
  • /89

    $2,000,000

    Sold Jun 18, 2026

    209 Glendale Rd, Oakland, MD 21550

    • 6 Beds
    • 4.5 Baths
    • 3,882 Sq Ft
    • Built 2001

    Last Sold Summary

    • 5% Below List Price
    • $515/SF
    • 122 Days On Market

    Current Estimated Value $1,979,570

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    209 Glendale Rd, Oakland, MD 21550
    • /82

      Est $1,624,675

      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

      Last Listing Agent Kathy Gibson Railey Realty, Inc.

  • /29

    $269,900

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    5 Laurel Brook Dr, Oakland, MD 21550

    Major renovations on this 2BR, 2BA Laurel brook two level townhome! Updates include new flooring, paint, fixtures, countertops, bathrooms and furnishings. One of the best dollar for dollar values still available at Deep Creek Lake and located within one mile of shopping, dining, entertainment, marinas and more! Enjoy a park-like setting with mature trees, common areas for relaxing or picnics and

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    5 Laurel Brook Dr, Oakland, MD 21550
  • /13

    $20,000

    Sold Nov 05, 2025

    0 Weber Ct, Oakland, MD 21550

    • Land
    • 10,454 Sq Ft
    • $83,333 per Acre

    Last Sold Summary

    • 10 Days On Market

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    0 Weber Ct, Oakland, MD 21550
    • /29

      Est $171,613

      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

      Last Listing Agent Sheila Howell Lake Homes 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, LLC

    233 Rhododendron Dr, Oakland, MD 21550
  • /20

    $17,000

    Sold Oct 29, 2025

    9 & 10 Grouse Run Rd, Oakland, MD 21550

    • Land
    • 41,817 Sq Ft
    • $17,708 per Acre

    Last Sold Summary

    • 50 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    9 & 10 Grouse Run Rd, Oakland, MD 21550
    • /33

      Est $421,571

      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

      Last Listing Agent Autumn McDaniel The KW Collective

  • /5

    $89,900

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

    0 15 75 Acres Bethlehem Rd Unit MDGA2011216, Oakland, MD 21550

    If you've been looking for a place to build while enjoying some peace and quiet, this 15.75± acre wooded property is worth a look. Tucked away off Bethlehem Road just minutes from town and close to the Potomac State Forest, it offers the privacy of a country setting without being far from everyday conveniences. One of the biggest advantages is the 7.02-acre buildable lot (Lot 8 on the recorded

    Thomas Long Railey Realty, Inc.

    0 15 75 Acres Bethlehem Rd Unit MDGA2011216, Oakland, MD 21550
  • /2

    $8,000

    Sold Aug 29, 2025

    0 E Water St, Oakland, MD 21550

    • Land
    • 14,374 Sq Ft
    • $24,242 per Acre

    Last Sold Summary

    • 2 Days On Market

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

    0 E Water St, Oakland, MD 21550
    • /47

      Est $1,807,657

      Not Listed For Sale

      1484 Paradise Point Rd, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 3,360 Sq Ft
      • Built 2022
      1484 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Kelsey Meyers Railey Realty, Inc.

  • /62

    $499,000

    Under Contract
    • 9 Beds
    • 3.5 Baths
    • 3,840 Sq Ft

    113 G St, Oakland, MD 21550

    "The Colonial" is located on a corner lot in the heart of Mt. Lake Park's Historical District. The Victorian charm features 2 staircases, original wide oak moldings, trim, yellow pine floors and ornate woodworking throughout. Originally built as a boarding house (9 bedrooms!), the versatility of this property is incredible. Enjoy modern features like a gourmet kitchen with granite countertops,

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    113 G St, Oakland, MD 21550
  • /22

    $60,000

    Sold Apr 24, 2026

    3501 George Washington Hwy, Oakland, MD 21550

    • Land
    • 2.86 Acres
    • $20,979 per Acre

    Last Sold Summary

    • 61% Below List Price
    • 707 Days On Market

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    3501 George Washington Hwy, Oakland, MD 21550
    • /7

      Est $341,765

      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

      Last Listing Agent Russell Bounds Railey Realty, Inc.

  • /16

    $190,000

    • 1,056 Sq Ft

    513 M St, Oakland, MD 21550

    Experience 513 M St, a residence recently updated with fresh interior and exterior paint, providing a renewed aesthetic throughout every area. The kitchen features all stainless steel appliances, enhancing the functionality and visual appeal of the culinary space. An external storage shed provides practical additional utility space for organized keeping of various items. Updated style and

    Jacqueline Moore Open Door Brokerage, LLC

    513 M St, Oakland, MD 21550
  • /37

    $120,000

    Sold Dec 04, 2025

    204 E St, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 2,084 Sq Ft
    • Built 1975

    Last Sold Summary

    • $58/SF
    • 1 Day On Market

    Current Estimated Value $125,461

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    204 E St, Oakland, MD 21550
    • /52

      Est $229,110

      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

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

Showing Results 321 - 360, Page 9 of 18

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