10,739

Oakland, MD Homes

Section Image Section Image
  • /82

    $1,900,000 Sold May 16, 2025

    228 Paradise Heights, Oakland, MD 21550

    • 4 Beds
    • 4.5 Baths
    • 2,249 Sq Ft
    • Built 1989

    Last Sold Summary

    • $845/SF
    • 5 Days On Market

    Current Estimated Value $1,935,297

    Last Listing Agent Jay Quinn Taylor Made Deep Creek Real Estate

    228 Paradise Heights, Oakland, MD 21550
    • /45

      Est $1,251,074 Not Listed For Sale

      20230 Garrett Hwy, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,470 Sq Ft
      • Built 1998
      20230 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 4% Below List Price
      • $526/SF
      • 13 Days On Market

      Last Sold Price $1,300,000

      Last Listing Agent Russell Bounds Railey Realty, Inc.

  • /50

    $315,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,416 Sq Ft

    163 Crestview Dr, Oakland, MD 21550

    Welcome to 163 Crestview Drive — a beautifully maintained 3-bedroom, 2.5-bath home nestled in the Mitchell Manor neighborhood. This inviting Cape Cod offers timeless charm, modern updates, and a peaceful setting just minutes from downtown Oakland. Many recent improvements including HVAC, water treatment/filtration system, flooring and landscaping! Step inside to an open, light-filled floor plan

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 502-1143

    163 Crestview Dr, Oakland, MD 21550
  • /29

    $369,900 Sold Oct 17, 2025

    366 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Built 1997

    Last Sold Summary

    • $266/SF
    • 152 Days On Market

    Current Estimated Value $375,718

    Last Listing Agent Adam Belasco Keller Williams Capital Properties

    366 Glendale Rd, Oakland, MD 21550
    • /76

      Est $839,989 Not Listed For Sale

      1368 Mountainview Dr, Oakland, MD 21550

      • 3 Beds
      • 3.5 Baths
      • 2,830 Sq Ft
      • Built 1992
      1368 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 8% Above List Price
      • $274/SF
      • 59 Days On Market

      Last Sold Price $775,000

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /33

    $160,000

    • 1 Bed
    • 1 Bath
    • 382 Sq Ft

    565 Glendale Rd Unit 210-A, Oakland, MD 21550

    Studio unit at Silver Tree Suites, one of Deep Creek Lake's most premier condo/hotel communities! Silver Tree Suites offers over 350' of pristine lakefront with western exposure. Located directly adjacent to Dutch's at Silver Tree, this location offers convenience to one of the areas most desirable restaurants, and is only 5-10 minutes to all of the local amenities and attractions you come to

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 623-5408

    565 Glendale Rd Unit 210-A, Oakland, MD 21550
  • /4

    $250,000 Sold Feb 05, 2026

    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550

    • Land
    • 45.7 Acres
    • $5,470 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 0 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550
    • /63

      Est $604,311 Not Listed For Sale

      265 Winding Trail Ln Unit 9A, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 4,200 Sq Ft
      • Built 2009
      265 Winding Trail Ln Unit 9A, Oakland, MD 21550

      Last Sold Summary

      • 1% Above List Price
      • $143/SF
      • 12 Days On Market

      Last Sold Price $599,000

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • /71

    $639,000

    • 5 Beds
    • 4.5 Baths
    • 2,200 Sq Ft

    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550

    Discover refined mountain and lake living in this quality built townhome at Mystic Creek on Deep Creek Lake, nestled in a quiet, serene setting with a truly custom feel. This spacious 5-bedroom, 4.5 bath residence offers an open concept main level ideal for entertaining, featuring hardwood floors throughout the main living area, abundant natural light, and seamless flow between the living,

    Melissa Long Railey Realty, Inc.

    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550
  • /2

    $20,000 Sold Mar 03, 2026

    0 N Hammond St, Oakland, MD 21550

    • Land
    • 0.48 Acre
    • $41,667 per Acre

    Last Sold Summary

    • 33% Below List Price
    • 6 Days On Market

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

    0 N Hammond St, Oakland, MD 21550
    • /47

      Est $409,053 Not Listed For Sale

      300 Big Rock Cabin Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,216 Sq Ft
      • Built 1999
      300 Big Rock Cabin Rd, Oakland, MD 21550

      Last Sold Summary

      • 20% Above List Price
      • $280/SF
      • 82 Days On Market

      Last Sold Price $340,000

      Last Listing Agent Lana Roby The KW Collective

  • /68

    $575,000

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550

    Lakefront living at it's best can be found in this completely renovated spacious condo. This three-level unit is the perfect place to get away together! With space to come together and space to escape, this unit promises both privacy and togetherness for a memorable Deep Creek Lake experience! The first level has a full kitchen with wine fridge and attached living room with an electric fireplace,

    Kevin Liller Railey Realty, Inc.

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
  • /20

    $237,000 Sold Oct 30, 2025

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 660 Sq Ft
    • Built 1990

    Last Sold Summary

    • $359/SF
    • 19 Days On Market

    Current Estimated Value $246,555

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

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550
    • /50

      Est $600,632 Not Listed For Sale

      208 Upper Penn Point Dr, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,086 Sq Ft
      • Built 1975
      208 Upper Penn Point Dr, Oakland, MD 21550

      Last Sold Summary

      • 46% Above List Price
      • $197/SF
      • 5 Days On Market

      Last Sold Price $410,000

      Last Listing Agent Andrew Eiswert Railey Realty, Inc.

  • /67

    $399,000

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    5024 Cranesville Rd, Oakland, MD 21550

    Just Reduced!! Charming 3-Bedroom Home with Scenic Mountain & Valley Views. Nestled on a 1.68-acre hillside in a beautiful conservation area, this 3-bedroom, 2.5-bath home combines natural charm with modern comfort. The native stone exterior and peaceful setting set the tone for this inviting residence.Inside, the main level features a spacious primary suite with a jetted tub, double vanity,

    Rich Orr Railey Realty, Inc.

    5024 Cranesville Rd, Oakland, MD 21550
  • /23

    $119,000 Sold Jul 18, 2025

    1714 Mayhew Inn Rd, Oakland, MD 21550

    • Land
    • 7.5 Acres
    • $15,867 per Acre

    Last Sold Summary

    • 56 Days On Market

    Last Listing Agent Brian Homberg Taylor Made Deep Creek Real Estate

    1714 Mayhew Inn Rd, Oakland, MD 21550
    • /69

      Est $540,682 Not Listed For Sale

      180 Winding Trail Ln Unit 5A, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 3,000 Sq Ft
      • Built 2006
      180 Winding Trail Ln Unit 5A, Oakland, MD 21550

      Last Sold Summary

      • 1% Above List Price
      • $178/SF
      • 277 Days On Market

      Last Sold Price $535,000

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

  • /150

    $3,690,000 Under Contract

    • 6 Beds
    • 5.5 Baths
    • 4,354 Sq Ft

    282 McComas Beach Terrace, Oakland, MD 21550

    Discover The Birch Bower, a rare architect-designed lakefront sanctuary offering 600 feet of private shoreline on Deep Creek Lake. Completed in 2021, this 6-bedroom, 5.5-bath residence exemplifies modern luxury, combining meticulous design, serene natural surroundings, and proven short-term rental performance. Turnkey consideration is available with a compelling offer. This extraordinary

    Morgan Boyer Hunt Country Sotheby's International Realty

    282 McComas Beach Terrace, Oakland, MD 21550
  • /27

    $225,000 Sold Feb 19, 2026

    1570 Garrett Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft
    • Built 1984

    Last Sold Summary

    • $160/SF
    • 122 Days On Market

    Current Estimated Value $231,434

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

    1570 Garrett Rd, Oakland, MD 21550
    • /30

      Est $387,657 Not Listed For Sale

      8081 Oakland Sang Run Rd, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 1,867 Sq Ft
      • Built 1941
      8081 Oakland Sang Run Rd, Oakland, MD 21550

      Last Sold Summary

      • 27% Above List Price
      • $163/SF
      • 122 Days On Market

      Last Sold Price $305,000

      Last Listing Agent ANGELA BOSLEY Taylor Made Deep Creek Real Estate

  • /61

    $379,000

    • 2 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    1167 Tall Oaks Dr, Oakland, MD 21550

    Picture perfect log cabin on 11 private, wooded acres in the gated Timbers on the Yough community featuring Youghiogheny River access. This inviting home features a metal roof, spacious covered deck, newly installed walkway, exterior fire pit, breakfast bar, and pellet stove. The primary bath offers dual sinks, an oversized soaking tub, dual shower heads and radiant floor heat!Recent updates

    Kellyann Green Railey Realty, Inc.

    1167 Tall Oaks Dr, Oakland, MD 21550
  • /44

    $589,000 Sold Sep 08, 2025

    939 Glendale Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,027 Sq Ft
    • Built 1995

    Last Sold Summary

    • $574/SF
    • 62 Days On Market

    Current Estimated Value $591,732

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    939 Glendale Rd, Oakland, MD 21550
    • /12

      Est $86,118 Not Listed For Sale

      6 Cedar Ln, Oakland, MD 21550

      6 Cedar Ln, Oakland, MD 21550

      Last Sold Summary

      • 761% Above List Price
      • 171 Days On Market

      Last Sold Price $10,000

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • /123

    $545,000

    • 4 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    328 Stool Rock Rd, Oakland, MD 21550

    Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of craftsmanship featuring handmade woodwork crafted from trees sourced directly from the property. Many specialty items will remain, including bathroom vanities, multiple dressers, a primary suite custom TV console, a built-in bunk bed, and more. The spacious primary suite was added in 2016 and offers a separate

    Kathy Gibson Railey Realty, Inc.

    328 Stool Rock Rd, Oakland, MD 21550
  • /27

    $165,000 Sold Oct 30, 2025

    306 Shady Acre Ln, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,288 Sq Ft
    • Built 1972

    Last Sold Summary

    • $72/SF
    • 2 Days On Market

    Current Estimated Value $176,306

    Last Listing Agent Brody Monahan Lake Homes Realty, LLC

    306 Shady Acre Ln, Oakland, MD 21550
    • /15

      Est $87,790 Not Listed For Sale

      149 Gobbler Run Rd, Oakland, MD 21550

      • Built 2006
      149 Gobbler Run Rd, Oakland, MD 21550

      Last Sold Summary

      • 158% Above List Price
      • $53/SF
      • 18 Days On Market

      Last Sold Price $34,000

      Last Listing Agent Sherry Nally Berkshire Hathaway HomeServices Homesale Realty

  • /147

    $5,150,000 Coming Soon

    • 8 Beds
    • 8.5 Baths
    • 10,300 Sq Ft

    1010 Holy Cross Dr, Oakland, MD 21550

    ICONIC. A design masterpiece of stone and timber — a true Rex Anderson build that reflects the seamless merging of inspiration and architecture. Warm, and undeniably welcoming, this home stands as a statement of craftsmanship and vision. Discover a breathtaking blend of contemporary luxury and timeless timber frame construction, perfectly positioned for privacy within the prestigious Reserve at

    Rachel Bruch Railey Realty, Inc.

    1010 Holy Cross Dr, Oakland, MD 21550
  • /5

    $34,500 Sold Jan 15, 2026

    62 Crosby Dr, Oakland, MD 21550

    • Land
    • 0.63 Acre
    • $54,762 per Acre

    Last Sold Summary

    • 73% Above List Price
    • 2,385 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Crosby Dr, Oakland, MD 21550
    • /98

      Est $483,324 Not Listed For Sale

      1506 Broadford Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,048 Sq Ft
      • Built 2023
      1506 Broadford Rd, Oakland, MD 21550

      Last Sold Summary

      • 2% Above List Price
      • $232/SF
      • 36 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /79

    $749,000

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft

    130 Timberloft Cir Unit 14, Oakland, MD 21550

    Centrally located in the heart of Deep Creek Lake, this beautifully maintained 3 bedroom, 3 bath home offers breathtaking lake and mountain views year round. Designed with an open floor plan, this home is perfect for entertaining. Enjoy the stunning scenery from the spacious main-level deck, or relax in the screened-in lower level porch. A cozy fireplace on both levels adds warmth and charm,

    Nicole Jackson Railey Realty, Inc.

    130 Timberloft Cir Unit 14, Oakland, MD 21550
  • /20

    $17,000 Sold Nov 21, 2025

    Lots 57 & 58 Black Oak Ln, Oakland, MD 21550

    • Land
    • 1.08 Acres
    • $15,741 per Acre

    Last Sold Summary

    • 24 Days On Market

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

    Lots 57 & 58 Black Oak Ln, Oakland, MD 21550
    • /4

      Est $36,593 Not Listed For Sale

      812 Winter Place, Oakland, MD 21550

      812 Winter Place, Oakland, MD 21550

      Last Sold Summary

      • 9% Below List Price
      • 3 Days On Market

      Last Sold Price $40,000

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

  • /109

    $6,499,900

    • 8 Beds
    • 8.5 Baths
    • 11,417 Sq Ft

    47 Holy Cross Cir, Oakland, MD 21550

    Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with

    Jon Bell Railey Realty, Inc.

    47 Holy Cross Cir, Oakland, MD 21550
  • /64

    $1,150,000 Sold Oct 24, 2025

    590 S Blakeslee Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 3,071 Sq Ft
    • Built 2000

    Last Sold Summary

    • $374/SF
    • 102 Days On Market

    Current Estimated Value $1,170,202

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

    590 S Blakeslee Rd, Oakland, MD 21550
    • /26

      Not Listed For Sale

      51 Stag Run, Oakland, MD 21550

      51 Stag Run, Oakland, MD 21550

      Last Sold Summary

      • 30 Days On Market

      Last Sold Price $2,750

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /62

    $314,000

    • 3 Beds
    • 2.5 Baths
    • 2,242 Sq Ft

    163 Mitchell Dr, Oakland, MD 21550

    Nestled in the charming Mitchell Manor community, this delightful split-level home offers a perfect blend of comfort and style. With 2,242 square feet of thoughtfully designed living space, this residence features three spacious bedrooms and two and a half bathrooms, ideal for both relaxation and entertaining. There is also a walk-in closet/dressing room to die for! Step inside to discover an

    Andrew Eiswert Railey Realty, Inc.

    163 Mitchell Dr, Oakland, MD 21550
  • /49

    $790,000 Sold May 09, 2025

    158 Silver Tree Ln, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,250 Sq Ft
    • Built 2003

    Last Sold Summary

    • $351/SF
    • 79 Days On Market

    Current Estimated Value $924,430

    Last Listing Agent Jon Bell Railey Realty, Inc.

    158 Silver Tree Ln, Oakland, MD 21550
    • /39

      Est $700,294 Not Listed For Sale

      94 Lehman Ln Unit 31, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 2,340 Sq Ft
      • Built 2007
      94 Lehman Ln Unit 31, Oakland, MD 21550

      Last Sold Summary

      • 1% Below List Price
      • $303/SF
      • 6 Days On Market

      Last Sold Price $709,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /93

    $799,000

    • 5 Beds
    • 6 Baths
    • 6,550 Sq Ft

    1001 Sutter Ln, Oakland, MD 21550

    Discover the ultimate mountain–lake getaway in this stunning 5BR Southern-style home on a private 2.4-acre wooded lot bordering Broadford Lake recreational area! Located just minutes from Deep Creek Lake and Wisp Resort, this magnificent property offers over 6,500 sq ft. and delivers unforgettable space, luxury, and privacy. Step inside to soaring cathedral ceilings, skylights, oak floors, and a

    Nina Beitzel Railey Realty, Inc.

    1001 Sutter Ln, Oakland, MD 21550
  • /39

    $450,000 Sold Nov 10, 2025

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Built 1972

    Last Sold Summary

    • $340/SF
    • 179 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home