10,549

Oakland, MD Homes

Section Image
    • /26

      Est $1,310,196

      Not Listed For Sale

      464 Lake Forest Dr, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 2,496 Sq Ft
      • Built 1997
      464 Lake Forest Dr, Oakland, MD 21550

      Last Sold Summary

      • 277 Days On Market

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

  • /56

    $745,000

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

    638 Glendale Rd, Oakland, MD 21550

    Spacious five-bedroom lakeview home offering the perfect blend of relaxation and warmth from the moment you enter. This established rental property “Terp’s Hideaway” features an open and inviting floorplan, five bedrooms, two family rooms, and three levels of living space, making it an ideal layout for hosting family and friends. Step outside onto the large deck to take in beautiful views or

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

    638 Glendale Rd, Oakland, MD 21550
  • /82

    $815,000

    Sold Jun 26, 2026

    891 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 4 Baths
    • 3,990 Sq Ft
    • Built 2002

    Last Sold Summary

    • 7% Below List Price
    • $204/SF
    • 46 Days On Market

    Current Estimated Value $858,036

    Last Listing Agent Brent Housley Railey Realty, Inc.

    891 Mountainview Dr, Oakland, MD 21550
    • /42

      Est $651,433

      Not Listed For Sale

      26 Arrowhead Ln, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,000 Sq Ft
      • Built 1988
      26 Arrowhead Ln, Oakland, MD 21550

      Last Sold Summary

      • 389 Days On Market

      Last Listing Agent Kellyann Green Railey Realty, Inc.

  • /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
  • /94

    $1,340,000

    Sold Apr 08, 2026

    336 Paradise Heights, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,826 Sq Ft
    • Built 1997

    Last Sold Summary

    • $474/SF
    • 159 Days On Market

    Current Estimated Value $1,436,140

    Last Listing Agent Susan Bell Railey Realty, Inc.

    336 Paradise Heights, Oakland, MD 21550
    • /26

      Est $158,267

      Not Listed For Sale

      419 Seneca Ave, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,184 Sq Ft
      • Built 1920
      419 Seneca Ave, Oakland, MD 21550

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Andrew Eiswert Railey Realty, Inc.

  • /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
  • /10

    $300,000

    Sold May 06, 2026

    4000 Area Broadford Rd, Oakland, MD 21550

    • Land
    • 56.5 Acres
    • $5,310 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    4000 Area Broadford Rd, Oakland, MD 21550
    • /62

      Est $1,265,383

      Not Listed For Sale

      581 Skippers Point Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,100 Sq Ft
      • Built 1977
      581 Skippers Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • /7

    $169,900

    • Land
    • 42,253 Sq Ft
    • $175,155 per Acre

    0 Mayhew Inn Rd Unit MDGA2012550, Oakland, MD 21550

    Picture this: your own slice of the woods at Deep Creek Lake, with a path straight to the water. This 0.97 acre raw land parcel (Tax ID 1218071878) borders Maryland's lakefront buffer strip and puts you in one of the most desirable settings in the area, part of the Millhouse Manor subdivision, with a community lake access area at the end of Red Run Cove. This no wake cove is made for lazy days of

    Jeremy Cunningham Railey Realty, Inc.

    0 Mayhew Inn Rd Unit MDGA2012550, Oakland, MD 21550
  • /43

    $290,000

    Sold Jun 01, 2026

    3749 Maryland Hwy, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 2,015 Sq Ft
    • Built 1982

    Last Sold Summary

    • 11% Below List Price
    • $144/SF
    • 63 Days On Market

    Current Estimated Value $284,862

    Last Listing Agent Jovan Vidulovic Keller Williams Realty

    3749 Maryland Hwy, Oakland, MD 21550
    • /87

      Est $303,684

      Not Listed For Sale

      233 N 2nd St, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 2,218 Sq Ft
      • Built 1914
      233 N 2nd St, Oakland, MD 21550

      Last Sold Summary

      • 432 Days On Market

      Last Listing Agent Julie Mead The KW Collective

  • /21

    $599,900

    • Land
    • 18.87 Acres
    • $31,791 per Acre

    0 Boy Scout Rd Unit MDGA2012474, Oakland, MD 21550

    An exceptional opportunity to own 18.87 acres in one of Deep Creek Lake's most desirable locations. Featuring 8 approved perc sites, this lake access property offers outstanding potential for a private estate, luxury mountain retreat, or future subdivision with the possibility of up to 8 homesites. Ideally situated on Boy Scout Road, the property provides the perfect balance of privacy and

    Jon Bell Railey Realty, Inc.

    0 Boy Scout Rd Unit MDGA2012474, Oakland, MD 21550
  • /36

    $829,000

    Sold May 22, 2026

    34 Hooppole Ct, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,355 Sq Ft
    • Built 1975

    Last Sold Summary

    • $612/SF
    • 0 Days On Market

    Current Estimated Value $802,749

    Last Listing Agent Rich Orr Railey Realty, Inc.

    34 Hooppole Ct, Oakland, MD 21550
    • /32

      Est $239,448

      Not Listed For Sale

      114 Waterwheel Rd, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1965
      114 Waterwheel Rd, Oakland, MD 21550

      Last Sold Summary

      • 138 Days On Market

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

  • /70

    $1,189,000

    New Construction Under Contract
    • 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
  • /4

    $12,000

    Sold Sep 25, 2025

    0 E Reese St, Oakland, MD 21550

    • Land
    • 10,890 Sq Ft
    • $48,000 per Acre

    Last Sold Summary

    • 4 Days On Market

    Last Listing Agent Thomas Long Railey Realty, Inc.

    0 E Reese St, Oakland, MD 21550
    • /44

      Est $161,367

      Not Listed For Sale

      15 D St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,680 Sq Ft
      • Built 1953
      15 D St, Oakland, MD 21550

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /53

    $340,000

    Under Contract
    • 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
  • /7

    $75,000

    Sold Aug 17, 2026

    0 Quentin Ln, Oakland, MD 21550

    • Land
    • 1.72 Acres
    • $43,605 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 14 Days On Market

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    0 Quentin Ln, Oakland, MD 21550
    • /34

      Est $205,659

      Not Listed For Sale

      700 N St, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,724 Sq Ft
      • Built 1973
      700 N St, Oakland, MD 21550

      Last Sold Summary

      • 57 Days On Market

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

  • /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
  • /52

    $508,000

    Sold Jun 18, 2026

    247 Sloan Tract Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 2004

    Last Sold Summary

    • 2% Above List Price
    • $392/SF
    • 2 Days On Market

    Current Estimated Value $500,501

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    247 Sloan Tract Rd, Oakland, MD 21550
    • /48

      Est $259,686

      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

      Last Listing Agent Michael Nelson Berkshire Hathaway HomeServices Homesale Realty

  • /42

    $249,900

    $50K 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

    Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

    400 Bear Dr E, Oakland, MD 21550
  • /59

    $815,000

    Sold Aug 10, 2026

    39 Leo Friend Rd, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 3,897 Sq Ft
    • Built 2003

    Last Sold Summary

    • 7% Below List Price
    • $209/SF
    • 27 Days On Market

    Current Estimated Value $866,878

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

    39 Leo Friend Rd, Oakland, MD 21550
    • /51

      Est $236,738

      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

      Last Listing Agent Anet Harris Taylor-Made Deep Creek Real Estate, LLC

  • /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
  • /62

    $305,000

    Sold Nov 07, 2025

    445 Dennett Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,410 Sq Ft
    • Built 1955

    Last Sold Summary

    • $216/SF
    • 5 Days On Market

    Current Estimated Value $313,004

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    445 Dennett Rd, Oakland, MD 21550
    • /31

      Est $191,920

      Not Listed For Sale

      1681 Shady Dell Rd, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1985
      1681 Shady Dell Rd, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

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

  • /51

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    181 Glotfelty Dr, Oakland, MD 21550

    Talk about central location! Only minutes to Deep Creek Lake, Wisp Resort and downtown Oakland! This 3 bedroom, 2 bath home sits on a nice-sized 1.29 AC partially wooded lot, at the end of a private, no thru street. Great outdoor living space as well with a covered porch, back deck and large 24x44 detached garage. Many upgrades & improvements by the current owner, to include new HVAC, all new

    Kathy Gibson Railey Realty, Inc.

    181 Glotfelty Dr, Oakland, MD 21550
  • /74

    $1,425,000

    Sold May 20, 2026

    2332 Paradise Point Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 1959

    Last Sold Summary

    • 2% Above List Price
    • $690/SF
    • 2 Days On Market

    Current Estimated Value $1,368,102

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    2332 Paradise Point Rd, Oakland, MD 21550
    • /40

      Est $183,719

      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

      Last Listing Agent Debra Beitzel Long & Foster Real Estate, Inc.

  • /33

    $1,095,000

    $105K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,914 Sq Ft

    826 G Swauger Rd, Oakland, MD 21550

    A Rare Fine Indeed! The private, end of the road farm is located in the much-desired Pleasant Valley area of southern Garrett County, MD.Built in 1933 and remodeled in 2020, this farmhouse is a must see. The inviting living area is complemented by a wood burning stove, while a LP gas furnace provides hot water radiant heat throughout the home. The kitchen features concrete countertops and is

    Larry Roth Railey Realty, Inc.

    826 G Swauger Rd, Oakland, MD 21550
  • /61

    $275,000

    Sold Sep 05, 2025

    648 S 3rd St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1940

    Last Sold Summary

    • $185/SF
    • 3 Days On Market

    Current Estimated Value $257,667

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    648 S 3rd St, Oakland, MD 21550
    • /22

      Est $199,488

      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

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

  • /68

    $460,000

    • 5 Beds
    • 2 Baths
    • 2,860 Sq Ft

    5154 Maryland Hwy, Oakland, MD 21550

    Escape to the tranquility of country living in this spacious 5-bedroom, 2-bath home nestled on over 2 acres and conveniently located just minutes from the recreational opportunities of Deep Creek Lake and the charming town of Oakland, The property offers the perfect combination of peaceful country living and easy access to shopping, dining, and year-round activities. The kitchen has been

    Charlene Deremer Aburn Coldwell Banker Home Town Realty

    5154 Maryland Hwy, Oakland, MD 21550
  • /24

    $38,000

    Sold Jul 02, 2026

    LOT 2 Oak Breeze Ln, Oakland, MD 21550

    • Land
    • 23,086 Sq Ft
    • $71,698 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 21 Days On Market

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    LOT 2 Oak Breeze Ln, Oakland, MD 21550
    • /87

      Est $464,442

      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

      Last Listing Agent Debra Beitzel Long & Foster Real Estate, Inc.

Showing Results 561 - 600, Page 15 of 18

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