10,771

Oakland, MD Homes

Section Image
    • /81

      Est $651,704

      Not Listed For Sale

      43 Robinwood Dr, Oakland, MD 21550

      • 3 Beds
      • 3.5 Baths
      • 2,921 Sq Ft
      • Built 2005
      43 Robinwood Dr, Oakland, MD 21550

      Last Sold Summary

      • 148 Days On Market

  • /62

    $735,000

    Under Contract
    • 5 Beds
    • 5 Baths
    • 3,664 Sq Ft

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    Check out this beautifully built and maintained 5 bedroom 5 bathroom lake area chalet style home. Located on the Southern side of the lake, near the headwaters of Deep Creek. The namesake stream that feeds into the nearby lake. This property offers it's new owners a tremendous amount of room for storage and entertaining and three levels of finished living space. The top floor is designed as an

    Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    1875 Pysell Crosscut Rd, 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 $902,561

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

    78 Mountainside Ct, Oakland, MD 21550
    • /16

      Est $71,504

      Not Listed For Sale

      36 Preston Ln, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 964 Sq Ft
      • Built 1918
      36 Preston Ln, Oakland, MD 21550

      Last Sold Summary

      • 1 Day On Market

  • /39

    $1,089,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,411 Sq Ft

    588 Lake Forest Dr, Oakland, MD 21550

    Welcome to Cabin Dreams — a charming rustic lakefront retreat with 134’ of beautiful, gently sloped lake frontage on Deep Creek Lake. Facing the sunrise with an inviting sandy shoreline, stunning lake views, and private Type A dock, this 3-bedroom + loft, 2-bath getaway offers the perfect blend of relaxation and adventure. Inside, warm wood accents, hardwood floors, mini-split AC/heating units,

    Nina Beitzel Railey Realty, Inc.

    588 Lake Forest 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 $829,112

    Last Listing Agent Jon Bell Railey Realty, Inc.

    53 Meadow Ct, Oakland, MD 21550
    • /44

      Est $709,732

      Not Listed For Sale

      870 Hunters Ridge Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,896 Sq Ft
      • Built 2007
      870 Hunters Ridge Dr, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /48

    $375,000

    $25K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 3,660 Sq Ft

    321 N 3rd St, Oakland, MD 21550

    Reduced and Ready to go!! Perfect one level retirement retreat or 2nd vacation home! Spacious and beautifully maintained all-brick rancher offering approximately 3,660 square feet of living space with room for everyone! This impressive home features 5 bedrooms, 2 full bathrooms, and a fully finished basement with its own private entrance—perfect for in-law potential, extended family living, or

    Christina Ford CENTURY 21 New Millennium

    321 N 3rd St, 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 $883,394

    Last Listing Agent Jon Bell Railey Realty, Inc.

    340 Grandview Dr, Oakland, MD 21550
    • /81

      Est $813,292

      Not Listed For Sale

      335 Mountainview Dr, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 3,142 Sq Ft
      • Built 2001
      335 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 29 Days On Market

  • /20

    $150,000

    New Construction $49K PRICE DROP Under Contract
    • 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, LLC

    3395 Fingerboard 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 $388,756

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    15 Village Dr Unit 1, Oakland, MD 21550
    • /56

      Est $533,887

      Not Listed For Sale

      741 Hoyes Run Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,160 Sq Ft
      • Built 1984
      741 Hoyes Run Rd, Oakland, MD 21550

      Last Sold Summary

      • 10 Days On Market

  • /50

    $1,200,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,156 Sq Ft

    209 Black Angus Dr, Oakland, MD 21550

    Beautiful and peaceful describes this 2 bedroom 2 bath retreat. Situated on 200' of prime lakefront this property is tucked away at the end of a gently sloping lane. The inviting setting includes a tennis/sport court with potential for pickle ball and just about any other outdoor activity you can think of. The property qualifies for a private type A dock and is located in a non-vacation rental

    Bill Weissgerber Railey Realty, Inc.

    209 Black Angus Dr, 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 $486,711

    Last Listing Agent Larry Smith Railey Realty, Inc.

    783 Mountainview Dr, Oakland, MD 21550
    • /125

      Est $2,406,903

      Not Listed For Sale

      427 Lake Shore Dr, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 4,584 Sq Ft
      • Built 1987
      427 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

  • /18

    $4,000

    Under Contract
    • Land
    • 20,473 Sq Ft
    • $8,511 per Acre

    Lot 36 Fox Tail Rd, Oakland, MD 21550

    Discover your mountain escape in Yough Mountain Resort, a gated recreational community in the scenic mountains of Western Maryland, just a short drive to Deep Creek Lake. This amenity-rich community is designed for outdoor enthusiasts, offering ATV and snowmobile trails, Yough River access, nearby state parks, hunting opportunities, plus a playground and pavilion area for gathering.This

    Shannon McWilliams Taylor-Made Deep Creek Real Estate, LLC

    Lot 36 Fox Tail Rd, Oakland, MD 21550
  • /35

    $380,000

    Sold Sep 26, 2025

    20160 Garrett Hwy Unit G509, Oakland, MD 21550

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

    Last Sold Summary

    • $594/SF
    • 24 Days On Market

    Current Estimated Value $374,646

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

    20160 Garrett Hwy Unit G509, Oakland, MD 21550
    • /65

      Est $3,786,843

      Not Listed For Sale

      2276 Paradise Point Rd, Oakland, MD 21550

      • 8 Beds
      • 5.5 Baths
      • 8,453 Sq Ft
      • Built 2006
      2276 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

  • /44

    $145,000

    Under Contract
    • 1 Bed
    • 1 Bath
    • 1,728 Sq Ft

    1099 Table Rock Rd, Oakland, MD 21550

    Nestled in the scenic countryside of Southern Garrett County, on 5+ acre property along North Fork Sand Run, this two-level home provides a solid foundation for renovation or customization, making it ideal for a full-time residence or mountain getaway. In addition to the home, the property features a large detached garage perfect for vehicles, equipment, hobbies, or workshop space, along with a

    Rich Orr Railey Realty, Inc.

    1099 Table Rock Rd, 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 $237,708

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    5202 Hutton Rd, Oakland, MD 21550
    • /56

      Est $370,348

      Not Listed For Sale

      5289 Oakland Sang Run Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,638 Sq Ft
      • Built 2006
      5289 Oakland Sang Run Rd, Oakland, MD 21550

      Last Sold Summary

      • 24 Days On Market

  • /115

    $2,350,000

    • 5 Beds
    • 6.5 Baths
    • 5,376 Sq Ft

    2725 Stockslager Rd, Oakland, MD 21550

    Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This custom-built log home is set against a picturesque landscape in Western Maryland, offering breathtaking nature views and embodying mountain charm and adventure. This home showcases impeccable craftsmanship, seamlessly blending with its natural surroundings while providing unrivaled comfort. Nestled on 1.03

    Shelia McCracken Taylor-Made Deep Creek Real Estate, LLC

    2725 Stockslager Rd, 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
    • /65

      Est $147,535

      Not Listed For Sale

      620 E Green St, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,668 Sq Ft
      • Built 1922
      620 E Green St, Oakland, MD 21550

      Last Sold Summary

      • 81 Days On Market

  • /5

    $27,500

    • Land
    • 0 Sq Ft

    Lot 54 Gallatin Spur Rd, Oakland, MD 21550

    Building lot located in the premier subdivision - Gallatin Woods! This beautifully wooded community is located in the heart of the Deep Creek Lake. This is a condominium ownership type in regards to the land itself, but is buildable for a single family home! There are 8 pre-approved building plans designed and engineered by Mountaineer Log Homes that range anywhere from 1571 to 3908 square feet.

    Nina Beitzel Railey Realty, Inc.

    Lot 54 Gallatin Spur Rd, 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
    • /76

      Est $202,077

      Not Listed For Sale

      501 G St, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,520 Sq Ft
      • Built 1979
      501 G St, Oakland, MD 21550

      Last Sold Summary

  • /25

    $259,900

    • 2 Beds
    • 1 Bath
    • 670 Sq Ft

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550

    Discover comfort and convenience in this charming 2-bedroom, 1-bath unit ideally located in the desirable Roman Ridge at Traders Landing community. Enjoy peaceful lake views from your covered front deck—the perfect spot to relax with your morning coffee or unwind in the evening. Inside, you’ll find a warm and inviting living space featuring a wood-burning fireplace to take the chill off during

    Larry Smith Railey Realty, Inc.

    181 Jeffrey Ln Unit 23-A, 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
    • /42

      Est $176,126

      Not Listed For Sale

      603 Oak St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,200 Sq Ft
      • Built 1965
      603 Oak St, Oakland, MD 21550

      Last Sold Summary

      • 49 Days On Market

  • /38

    $799,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,929 Sq Ft

    62 Middleton Rd, Oakland, MD 21550

    Lake Access with a Dock Slip located in the highly desirable Blakeslee community. This 3-bedroom, 2.5-bath mountain retreat offers the perfect mix of comfort, style, and Deep Creek Lake living. An open, inviting layout give the home a refreshed, updated feel, while the sun-filled four-season room quickly becomes the standout space of the home. A stunning pass-through stone fireplace anchors the

    Jon Bell Railey Realty, Inc.

    62 Middleton Rd, 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
    • /6

      Est $646,205

      Not Listed For Sale

      20488 Garrett Hwy, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 840 Sq Ft
      • Built 1946
      20488 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 125 Days On Market

  • /71

    $999,000

    $50K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 2,730 Sq Ft

    137 Paradise Gardens Rd, Oakland, MD 21550

    Remodeled 4BR/2BA lakefront A-frame with two deep water dock slips! Impressive renovation from top to bottom, this home has everything you are seeking in a vacation home AND a huge, fenced in yard surrounded by massive trees, fire pit and storage building. Features include a massive stone fireplace (wood burning), hot tub with lake views, large kitchen with island, custom tile showers & bathrooms

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    137 Paradise Gardens Rd, 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 $122,290

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    204 E St, Oakland, MD 21550
    • /80

      Est $716,531

      Not Listed For Sale

      1489 Mountainview Dr, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 3,066 Sq Ft
      • Built 2001
      1489 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 170 Days On Market

  • /24

    $419,000

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    560 Glendale Rd, Oakland, MD 21550

    Charming vintage Deep Creek Lake log cabin ideally located in the heart of Deep Creek Lake just minutes from area amenities. Full of character and thoughtfully restored, this established rental property is being sold completely furnished and turnkey. Enjoy filtered lake views from the inviting covered front porch, then unwind in the hot tub or gather around the fire pit after a day on the lake.

    Lauren McCann Railey Realty, Inc.

    560 Glendale Rd, Oakland, MD 21550
  • /11

    $375,000

    Sold Apr 30, 2026

    2173 King Wildesen Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • Built 2025

    Last Sold Summary

    • 0 Days On Market

    Current Estimated Value $374,428

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

    2173 King Wildesen Rd, Oakland, MD 21550
    • /85

      Est $1,734,425

      Not Listed For Sale

      739 Glendale Rd, Oakland, MD 21550

      • 6 Beds
      • 6.5 Baths
      • 4,160 Sq Ft
      • Built 2003
      739 Glendale Rd, Oakland, MD 21550

      Last Sold Summary

      • 90 Days On Market

Showing Results 321 - 360, Page 9 of 18

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