10,771

Oakland, MD Homes

Section Image
  • /71

    $590,000

    Sold Jan 16, 2026

    3084 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,464 Sq Ft
    • Built 1999

    Last Sold Summary

    • $239/SF
    • 305 Days On Market

    Current Estimated Value $619,918

    Last Listing Agent Jon Bell Railey Realty, Inc.

    3084 Lake Shore Dr, Oakland, MD 21550
    • /48

      Est $224,201

      Not Listed For Sale

      1634 Shady Dell Rd, Oakland, MD 21550

      • 4 Beds
      • 1 Bath
      • 1,176 Sq Ft
      • Built 1950
      1634 Shady Dell Rd, Oakland, MD 21550

      Last Sold Summary

      • 21 Days On Market

  • /30

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft

    98 Bear Run Rd, Oakland, MD 21550

    Make it your own! This 2-acre parcel comes with two additional parcels of 17.96 and 24.23 acres for a total of 42.19 acres. The 2-acre parcel is improved by a fully furnished (26’X42’), 3-bedroom, 2-bathroom Ranch style dwelling and a large parking area. The interior offers a spacious living room, and an eat-in kitchen with all appliances, furniture and window AC units. The land is un-zoned

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    98 Bear Run Rd, Oakland, MD 21550
  • /47

    $1,762,500

    Sold Jul 29, 2025

    1484 Paradise Point Rd, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,360 Sq Ft
    • Built 2022

    Last Sold Summary

    • $525/SF
    • 16 Days On Market

    Current Estimated Value $1,728,858

    Last Listing Agent Kelsey Meyers Railey Realty, Inc.

    1484 Paradise Point Rd, Oakland, MD 21550
    • /51

      Est $245,729

      Not Listed For Sale

      685 Oakland Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,378 Sq Ft
      • Built 1975
      685 Oakland Dr, Oakland, MD 21550

      Last Sold Summary

      • 21 Days On Market

  • /55

    $400,000

    $120K PRICE INCREASE
    • Land
    • 43.72 Acres
    • $9,149 per Acre

    3257 George Washington Hwy, Oakland, MD 21550

    Discover approximately 43.72 acres of beautiful mostly wooded land offering privacy, mountain views, and exceptional convenience. This expansive property provides easy access to both George Washington Highway and Garrett Highway, making travel simple while still feeling tucked away in nature. Set up with a well and septic system, this property is perfect to build your dream home with an already

    Justin Liller Railey Realty, Inc.

    3257 George Washington Hwy, Oakland, MD 21550
  • /68

    $310,000

    Sold Jul 31, 2025

    707 Sunshine Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,052 Sq Ft
    • Built 2004

    Last Sold Summary

    • $151/SF
    • 94 Days On Market

    Current Estimated Value $309,007

    Last Listing Agent Tyler Burch Burch Real Estate Group, LLC

    707 Sunshine Dr, Oakland, MD 21550
    • /40

      Est $169,891

      Not Listed For Sale

      5459 Hutton Rd, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 1940
      5459 Hutton Rd, Oakland, MD 21550

      Last Sold Summary

      • 113 Days On Market

  • /70

    $1,189,000

    New Construction
    • 6 Beds
    • 5.5 Baths
    • 3,482 Sq Ft

    248 Tarn Dr, Oakland, MD 21550

    Brand new construction in the desirable Mountainside community! This thoughtfully designed 6-bedroom mountain retreat offers 4 spacious primary suites, blending modern mountain style with functionality and comfort throughout. The open floorplan features vaulted ceilings, luxury finishes, quartz countertops, and multiple gathering spaces designed for entertaining and relaxation alike. Enjoy cozy

    Lauren McCann Railey Realty, Inc.

    248 Tarn Dr, Oakland, MD 21550
  • /30

    $17,000

    Sold May 28, 2026

    Lots 37 & 38 Fir Tree Dr, Oakland, MD 21550

    • Land
    • 1.58 Acres
    • $10,759 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 12 Days On Market

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

    Lots 37 & 38 Fir Tree Dr, Oakland, MD 21550
    • /22

      Est $182,210

      Not Listed For Sale

      615 E High St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,180 Sq Ft
      • Built 1920
      615 E High St, Oakland, MD 21550

      Last Sold Summary

      • 257 Days On Market

  • /53

    $340,000

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft

    254 Little Mountain Rd, Oakland, MD 21550

    Escape to the mountains at 254 Little Mountain Road, where privacy, comfort, and outdoor adventure come together on nearly 5 acres in the sought-after Backbone Ridge community. Surrounded by mature trees and mountain scenery. Inside, you'll find warm wood accents and a cozy wood-burning fireplace that anchors the inviting living space. Multiple gathering areas provide flexibility for

    Amy Skipper Railey Realty, Inc.

    254 Little Mountain Rd, Oakland, MD 21550
  • /66

    $490,000

    Sold Aug 08, 2025

    462 Skippers Point Rd, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 1983

    Last Sold Summary

    • $302/SF
    • 51 Days On Market

    Current Estimated Value $512,097

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    462 Skippers Point Rd, Oakland, MD 21550
    • /87

      Est $463,273

      Not Listed For Sale

      524 Bray School Rd, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,536 Sq Ft
      • Built 2003
      524 Bray School Rd, Oakland, MD 21550

      Last Sold Summary

      • 11 Days On Market

  • /5

    $124,900

    • Land
    • 1.02 Acres
    • $122,451 per Acre

    Lot 53 Mountainview Dr, Oakland, MD 21550

    Ready to build lot in Deep Creek Lake's Mountainside Subdivision. This wooded lot is relatively level can be connected to public water and has an approved percolation test for an onsite septic system. Build you dream home in this mountaintop community with homes values ranging up to $2,000,000.

    Richard Saunders Samson Properties

    Lot 53 Mountainview Dr, Oakland, MD 21550
  • /44

    $225,000

    Sold Jul 18, 2025

    600 Hope Ave, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,480 Sq Ft
    • Built 1981

    Last Sold Summary

    • $91/SF
    • 21 Days On Market

    Current Estimated Value $227,191

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    600 Hope Ave, Oakland, MD 21550
    • /38

      Est $167,267

      Not Listed For Sale

      514 M St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,326 Sq Ft
      • Built 1945
      514 M St, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /42

    $279,900

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 560 Sq Ft

    400 Bear Dr E, Oakland, MD 21550

    Tucked away in the scenic beauty of Yough Mountain Resort, this exceptional 2-bedroom, 2-bath log cabin offers the perfect blend of rustic charm and modern comfort. Spanning two stories, this immaculately maintained home has seen thoughtful renovations in recent years, creating a warm and inviting retreat that’s move-in ready. Step inside to discover cozy living spaces ideal for relaxing after a

    Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

    400 Bear Dr E, Oakland, MD 21550
  • /35

    $285,000

    Sold Nov 13, 2025

    473 Cumberland Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,389 Sq Ft
    • Built 1989

    Last Sold Summary

    • $205/SF
    • 155 Days On Market

    Current Estimated Value $295,549

    Last Listing Agent Jeremy McDonough Mr. Lister Realty

    473 Cumberland Rd, Oakland, MD 21550
    • /50

      Est $330,831

      Not Listed For Sale

      15705 Garrett Hwy, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,046 Sq Ft
      • Built 1965
      15705 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 146 Days On Market

  • /6

    $19,900

    • Land
    • 1.35 Acres
    • $14,741 per Acre

    Lot 18 Buck Dr, Oakland, MD 21550

    This 1.352 acre lot borders Buck Drive and also Antelope Drive. It is best to access the lot using the directions provided via Antelope Drive as it is a much better road. Buck Drive is very difficult to traverse and access through Antelope Drive is recommended. Pictures of the lot are taken from Antelope Drive. Perc approved for a three bedroom home with a sand mound system. Wooded lot just

    Kevin Liller Railey Realty, Inc.

    Lot 18 Buck Dr, Oakland, MD 21550
  • /20

    $55,000

    Sold Nov 17, 2025

    19 Pheasant Run, Oakland, MD 21550

    • Land
    • 2.84 Acres
    • $19,366 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Kathy Gibson Railey Realty, Inc.

    19 Pheasant Run, Oakland, MD 21550
    • /67

      Est $298,471

      Not Listed For Sale

      301 Oak St, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,400 Sq Ft
      • Built 1963
      301 Oak St, Oakland, MD 21550

      Last Sold Summary

      • 265 Days On Market

  • /38

    $79,999

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    1358 Crellin Underwood Rd, Oakland, MD 21550

    Charming 2-bedroom, 1-bath home offering a fantastic opportunity for buyers looking to add their own personal touch. Recent updates include a metal roof, 2 propane wall unit heaters, and a hot water heater. Enjoy the back covered deck overlooking the woods and the youghiogheny river below. This property needs a bit of TLC but is full of potential and character. Located in a highly desirable

    Lucas Muenchow Railey Realty, Inc.

    1358 Crellin Underwood Rd, Oakland, MD 21550
  • /18

    $160,000

    Sold Aug 28, 2025

    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550

    • Land
    • 25 Acres
    • $6,400 per Acre

    Last Sold Summary

    • 44 Days On Market

    Last Listing Agent Ally Litten Mountainside Home Realty

    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550
    • /7

      Est $123,454

      Not Listed For Sale

      106 E 3rd Ave, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 708 Sq Ft
      • Built 1930
      106 E 3rd Ave, Oakland, MD 21550

      Last Sold Summary

      • 93 Days On Market

  • /30

    $144,000

    $15K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 382 Sq Ft

    565 Glendale Rd Unit 124, Oakland, MD 21550

    Updated Lakefront Suite at Silver Tree – Affordable Deep Creek Lake Living with Strong Rental Income Enjoy the best of Deep Creek Lake with this beautifully updated suite at the highly desirable Suites at Silver Tree. Offering the perfect combination of lakefront location, modern upgrades, and proven rental income, Suite A124 is an incredible opportunity for those looking for a personal getaway,

    ANGELA BOSLEY Taylor-Made Deep Creek Real Estate, LLC

    565 Glendale Rd Unit 124, Oakland, MD 21550
  • /2

    $200,000

    Sold Feb 27, 2026

    0 Laurel Run Rd, Oakland, MD 21550

    • Land
    • 70 Acres
    • $2,857 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    0 Laurel Run Rd, Oakland, MD 21550
    • /64

      Est $516,785

      Not Listed For Sale

      702 Pocahontas St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,288 Sq Ft
      • Built 1955
      702 Pocahontas St, Oakland, MD 21550

      Last Sold Summary

      • 25 Days On Market

  • /2

    $339,000

    $30K PRICE DROP
    • Land
    • 20,473 Sq Ft
    • $721,277 per Acre

    8946 Oakland Sang Run Rd, Oakland, MD 21550

    There are 3 adjacent parcels included with this sale :Tax ID - 1206034144, 1206020860, 1206007082 All parcels together are 8 acres WARNING: The house on this property is condemned and ready for tear down. Enter at your own risk.

    Joe Zorzit Eagle Commercial Realty

    8946 Oakland Sang Run Rd, Oakland, MD 21550
  • /73

    $1,800,000

    Sold Jun 12, 2026

    62 Duck Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 4,150 Sq Ft
    • Built 1980

    Last Sold Summary

    • 5% Below List Price
    • $434/SF
    • 13 Days On Market

    Current Estimated Value $1,884,227

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

    62 Duck Cove Rd, Oakland, MD 21550
    • /38

      Est $983,467

      Not Listed For Sale

      3529 Lake Shore Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,150 Sq Ft
      • Built 1945
      3529 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 272 Days On Market

  • /53

    $1,500,000

    Sold Dec 01, 2025

    1674 Paradise Point Rd, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft
    • Built 1955

    Last Sold Summary

    • $641/SF
    • 465 Days On Market

    Current Estimated Value $1,471,256

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1674 Paradise Point Rd, Oakland, MD 21550
    • /40

      Est $305,788

      Not Listed For Sale

      250 N 4th St, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,580 Sq Ft
      • Built 1934
      250 N 4th St, Oakland, MD 21550

      Last Sold Summary

      • 112 Days On Market

  • /64

    $695,000

    Sold Oct 09, 2025

    353 Basswood Way Unit 24, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,664 Sq Ft
    • Built 2005

    Last Sold Summary

    • $261/SF
    • 14 Days On Market

    Current Estimated Value $673,415

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    353 Basswood Way Unit 24, Oakland, MD 21550
    • /24

      Est $162,772

      Not Listed For Sale

      107 E Mason St, Oakland, MD 21550

      • 4 Beds
      • 1.5 Baths
      • 2,256 Sq Ft
      • Built 1914
      107 E Mason St, Oakland, MD 21550

      Last Sold Summary

      • 18 Days On Market

  • /61

    $650,000

    Sold Aug 21, 2025

    1006 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 1,935 Sq Ft
    • Built 1993

    Last Sold Summary

    • $336/SF
    • 27 Days On Market

    Current Estimated Value $683,088

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1006 Lake Shore Dr, Oakland, MD 21550
    • /100

      Est $1,755,703

      Not Listed For Sale

      946 Glendale Rd, Oakland, MD 21550

      • 7 Beds
      • 6.5 Baths
      • 3,546 Sq Ft
      • Built 2001
      946 Glendale Rd, Oakland, MD 21550

      Last Sold Summary

      • 16 Days On Market

  • /48

    $279,000

    Sold Sep 25, 2025

    215 N 10th St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,518 Sq Ft
    • Built 1973

    Last Sold Summary

    • 3% Below List Price
    • $184/SF
    • 6 Days On Market

    Current Estimated Value $282,147

    Last Listing Agent ADAM MURRAY BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    215 N 10th St, Oakland, MD 21550
    • /50

      Est $618,525

      Not Listed For Sale

      697 Mountainview Dr, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,420 Sq Ft
      • Built 1994
      697 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 55 Days On Market

Showing Results 521 - 560, Page 14 of 18

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