10,771

Oakland, MD Homes

Section Image
    • /66

      Est $192,358

      Not Listed For Sale

      1606 Wheeling Ave, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,502 Sq Ft
      • Built 1976
      1606 Wheeling Ave, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • /59

    $875,000

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 3,897 Sq Ft

    39 Leo Friend Rd, Oakland, MD 21550

    Stunning split lakefront retreat with sweeping views and Type-A dock. Experience exceptional lake life in this beautifully maintained one owner home offering breathtaking lake views and timeless craftsmanship in a serene landscaped setting. This impressive 3 bedroom 3.5 bathroom residence welcomes you through an elegant foyer with soaring cathedral ceilings and a striking oak staircase that sets

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    39 Leo Friend Rd, Oakland, MD 21550
  • /22

    $60,000

    Pending
    • 2 Beds
    • 1 Bath
    • 1,600 Sq Ft

    422 Maple Ave, Oakland, MD 21550

    Investor opportunity in a highly desirable location! This property has been gutted and is ready for your vision. A rare chance to renovate and customize to your exact specifications. Ideal for resale, rental investment, or personal use. Ideally located near Loch Lynn Heights Wetland Trails, soccer complex, and community park. Great potential for the right buyer. RAILEY REALTY IS NOT THE CARETAKER

    Nicole Jackson Railey Realty, Inc.

    422 Maple Ave, Oakland, MD 21550
    • /24

      Est $224,560

      Not Listed For Sale

      123 Spruce St, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,392 Sq Ft
      • Built 1990
      123 Spruce St, Oakland, MD 21550

      Last Sold Summary

      • 7 Days On Market

  • /13

    $34,900

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,920 Sq Ft

    3482 Oakland Sang Run Rd, Oakland, MD 21550

    Situated in a prime location just minutes from Wisp Resort and Deep Creek Lake. The value here is in the land and location. With nearly one acre, the property offers strong potential to build a custom home or vacation retreat in a highly desirable area. This home is in very poor condition. Do not enter the home or step onto the front porch, as both are unsafe. This property is ready for a buyer

    Casey Oleynikov Pearson Smith Realty, LLC

    3482 Oakland Sang Run Rd, Oakland, MD 21550
  • /20

    $195,000

    Sold Nov 12, 2025

    210 Seneca Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,204 Sq Ft
    • Built 1996

    Last Sold Summary

    • $162/SF
    • 2 Days On Market

    Current Estimated Value $191,817

    Last Listing Agent Andrew Orr The KW Collective

    210 Seneca Ave, Oakland, MD 21550
    • /69

      Est $842,449

      Not Listed For Sale

      79 Hummingbird Ct, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,800 Sq Ft
      • Built 1999
      79 Hummingbird Ct, Oakland, MD 21550

      Last Sold Summary

      • 59 Days On Market

  • /24

    $44,900

    Pending
    • Land
    • 23,086 Sq Ft
    • $84,717 per Acre

    LOT 2 Oak Breeze Ln, Oakland, MD 21550

    Beautiful 0.53-acre corner lot in the desirable Oak Breeze Estates community! Located at the corner of Oak Breeze Lane and John Drive, this level homesite offers a wonderful setting for your dream home in one of Oakland’s established residential neighborhoods. Public water and sewer taps available per Oakland Town Administrator. Convenient location near schools, shopping, dining, and WVU Regional

    Nina Beitzel Railey Realty, Inc.

    LOT 2 Oak Breeze Ln, Oakland, MD 21550
  • /40

    $560,000

    Sold Jun 20, 2025

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2009

    Last Sold Summary

    • $170/SF
    • 52 Days On Market

    Current Estimated Value $550,493

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

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    • /86

      Est $803,510

      Not Listed For Sale

      105 Meadow Ct, Oakland, MD 21550

      • 4 Beds
      • 6 Baths
      • 3,192 Sq Ft
      • Built 2004
      105 Meadow Ct, Oakland, MD 21550

      Last Sold Summary

      • 47 Days On Market

  • /28

    $199,900

    • Land
    • 3.32 Acres
    • $60,211 per Acre

    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550

    OAKLAND, MD – 3.318 UNRESTRICTED ACRES “READY TO BUILD” THAT VACATION HOME OR FULL TIME RESIDENCE. THE SUBJECT PROPERTY IS IN THE DEEP CREEK LAKE RESORT AREA. ALL AMENITIES ASSOCIATED WITH A MAJOR RESORT AREA ARE WITHIN A SHORT DRIVE OF THE SUBJECT PROPERTY. FULLY WOODED. MATURE HARDWOOD THRU-OUT. LEVEL TOPOGRAPHY. CLOSE PROXIMITY TO BOAT LAUNCH.

    Mike Haywood The Mike Haywood Group

    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
  • /32

    $232,500

    Sold Jul 10, 2025

    114 Waterwheel Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1965

    Last Sold Summary

    • $242/SF
    • 138 Days On Market

    Current Estimated Value $229,328

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

    114 Waterwheel Rd, Oakland, MD 21550
    • /59

      Est $413,317

      Not Listed For Sale

      57 Allegro Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,524 Sq Ft
      • Built 2004
      57 Allegro Ln, Oakland, MD 21550

      Last Sold Summary

      • 67 Days On Market

  • /67

    $699,000

    • 5 Beds
    • 3 Baths
    • 2,560 Sq Ft

    170 Cherrywood Dr, Oakland, MD 21550

    4/5BR 3BA custom home (3900+ total sf!) on 8+ acres of peaceful tranquility! Conveys with 2 lots (6 & 7) totaling 8.05 acres of wooded land in a laid back HOA that allows chickens & embraces the outdoor amenities Garrett County offers. Private and secluded rural location that is just minutes from town, schools, shopping and dining. This home was custom designed for work from home professionals -

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    170 Cherrywood Dr, Oakland, MD 21550
  • /33

    $130,000

    Sold May 22, 2026

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

    • 1 Bed
    • 1 Bath
    • 382 Sq Ft
    • Built 2006

    Last Sold Summary

    • 26% Below List Price
    • $340/SF
    • 225 Days On Market

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

    565 Glendale Rd Unit 210-A, Oakland, MD 21550
    • /73

      Est $613,209

      Not Listed For Sale

      491 Edens Ridge Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 3,318 Sq Ft
      • Built 2003
      491 Edens Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 9 Days On Market

  • /32

    $304,000

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 780 Sq Ft

    565 Glendale Rd Unit B206, Oakland, MD 21550

    Charming true 1-bedroom + loft (can be used as 2nd bedroom) condo at Silver Tree Suites, LAKEFRONT living at its finest! This spacious second-floor unit features a private balcony, fully equipped kitchenette, cozy gas fireplace and abundant natural light. Enjoy resort-style amenities including a fitness center, sauna, on-site laundry and game room, plus steps-away fine dining at Dutch’s at Silver

    Carlos Espinoza Jason Mitchell Group

    565 Glendale Rd Unit B206, Oakland, MD 21550
  • /38

    $100,000

    Sold Jul 11, 2025

    5914 Maryland Hwy, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,775 Sq Ft
    • Built 1973

    Last Sold Summary

    • $56/SF
    • 4 Days On Market

    Current Estimated Value $177,437

    Last Listing Agent Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    5914 Maryland Hwy, Oakland, MD 21550
    • /49

      Est $360,476

      Not Listed For Sale

      19398 Garrett Hwy, Oakland, MD 21550

      • 5 Beds
      • 2 Baths
      • 2,414 Sq Ft
      • Built 1940
      19398 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 168 Days On Market

  • /24

    $1,025,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    127 Paradise Heights, Oakland, MD 21550

    Beautifully renovated lake access log cabin with a deeded dock slip in a quiet cove with private 29 acres of trails (ATVs/snowmobiles permitted). Recent renovations (approx. $200K) include new wrap around deck, new roof, re-stained siding, new kitchen with granite counters, new appliances, new bathrooms, new LVFs throughout the house, new 2 car garage doors, new mini-split heat and A/C units, and

    Norman Domingo XRealty.NET LLC

    127 Paradise Heights, Oakland, MD 21550
  • /46

    $1,120,000

    Sold Jul 08, 2025

    636 Paradise Heights, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,028 Sq Ft
    • Built 1986

    Last Sold Summary

    • $552/SF
    • 11 Days On Market

    Current Estimated Value $1,102,947

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    636 Paradise Heights, Oakland, MD 21550
    • /33

      Est $243,232

      Not Listed For Sale

      1070 Sunrise Dr, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,144 Sq Ft
      • Built 1988
      1070 Sunrise Dr, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

  • /19

    $185,000

    • Land
    • 1.35 Acres
    • $137,037 per Acre

    0 Pysell Crosscut Rd Unit MDGA2012040, Oakland, MD 21550

    Discover the perfect canvas for your dream home on this expansive 1.35-acre parcel of land, where possibilities abound and nature's beauty surrounds you. Nestled in a serene setting, this property offers a unique opportunity to create a personalized retreat tailored to your lifestyle. Imagine waking up each morning to the gentle rustle of leaves and the soft sounds of nature, all while being just

    Larry Smith Railey Realty, Inc.

    0 Pysell Crosscut Rd Unit MDGA2012040, Oakland, MD 21550
  • /22

    $180,000

    Sold Sep 12, 2025

    4643 Oakland Sang Run Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 1979

    Last Sold Summary

    • $208/SF
    • 4 Days On Market

    Current Estimated Value $192,898

    Last Listing Agent Jon Bell Railey Realty, Inc.

    4643 Oakland Sang Run Rd, Oakland, MD 21550
    • /48

      Est $459,850

      Not Listed For Sale

      482 Pergin Farm Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 2,160 Sq Ft
      • Built 1980
      482 Pergin Farm Rd, Oakland, MD 21550

      Last Sold Summary

      • 128 Days On Market

  • /43

    $475,000

    • 4 Beds
    • 3.5 Baths
    • 1,492 Sq Ft

    333 Sloan Tract Rd, Oakland, MD 21550

    Charming cabin off the coveted Lake Shore Drive offering seasonal lake views. This home has three levels of living space, hardwood flooring and a nice fireplace. The lower level is totally finished with walk-out access. There are multiple covered porches plus a hot tub that are great outdoor spaces to enjoy year round. This home feels very secluded but is just minutes to Deep Creek Lake and Wisp

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

    333 Sloan Tract Rd, Oakland, MD 21550
  • /45

    $750,000

    Sold Jan 16, 2026

    198 Grandview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,744 Sq Ft
    • Built 2003

    Last Sold Summary

    • $273/SF
    • 150 Days On Market

    Current Estimated Value $778,838

    Last Listing Agent Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, MD 21550
    • /46

      Est $1,442,381

      Not Listed For Sale

      2127 Lake Shore Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,546 Sq Ft
      • Built 1960
      2127 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 20 Days On Market

  • /28

    $160,000

    • Land
    • 3.04 Acres
    • $52,632 per Acre

    132 &132A Tarn Dr, Oakland, MD 21550

    Lake Access Lots 132 & 132A in the Mountainside Community offer 3.04 acres of privacy at the end of a quiet cul-de-sac on Tarn Drive. Combined and recorded in the land records as one building site, this property is already serviced by public water and sewer—making it ready for your future build. The gently wooded setting provides a peaceful, natural backdrop with plenty of space to design your

    Rich Orr Railey Realty, Inc.

    132 &132A Tarn Dr, Oakland, MD 21550
  • /48

    $250,000

    Sold Jun 11, 2026

    18 Ollie North Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,956 Sq Ft
    • Built 1975

    Last Sold Summary

    • 13% Below List Price
    • $128/SF
    • 31 Days On Market

    Current Estimated Value $270,053

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    18 Ollie North Rd, Oakland, MD 21550
    • /97

      Est $2,339,389

      Not Listed For Sale

      1738 Paradise Point Rd, Oakland, MD 21550

      • 7 Beds
      • 5.5 Baths
      • 4,260 Sq Ft
      • Built 2002
      1738 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 127 Days On Market

  • /86

    $599,000

    • 5 Beds
    • 3.5 Baths
    • 3,542 Sq Ft

    428 Sam Snead Cir, Oakland, MD 21550

    Welcome to this beautifully appointed 5-bedroom, 3.5-bath home located in one of Oakland’s most desirable neighborhoods—Country Club Acres, bordering The Golf Club at Oakland. Offering the perfect blend of modern style, comfort, and convenience, this spacious home is designed to accommodate both everyday living and entertaining. Step inside to discover an inviting open-concept floor plan

    Justin Liller Railey Realty, Inc.

    428 Sam Snead Cir, Oakland, MD 21550
  • /65

    $558,000

    Sold Nov 10, 2025

    72 Cliff Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft
    • Built 1988

    Last Sold Summary

    • $256/SF
    • 32 Days On Market

    Current Estimated Value $558,613

    Last Listing Agent Larry Smith Railey Realty, Inc.

    72 Cliff Dr, Oakland, MD 21550
    • /78

      Est $219,813

      Not Listed For Sale

      1400 Oakland Ave, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 1972
      1400 Oakland Ave, Oakland, MD 21550

      Last Sold Summary

      • 8 Days On Market

  • /8

    $18,000

    $7K PRICE DROP
    • Land
    • 3 Acres
    • $6,000 per Acre

    0 Hoye St, Oakland, MD 21550

    Make an offer, buy it now +/- 2.96 Acre lot of land in Garrett County. Close to the West Virginias Border. Easy access to major traffic artery Seneca Trail Highway. Parcel is vacant. Deposit is $5,000

    Adam Shpritz

    0 Hoye St, Oakland, MD 21550
  • /65

    $379,000

    Sold Oct 08, 2025

    113 G St, Oakland, MD 21550

    • 9 Beds
    • 3.5 Baths
    • 3,840 Sq Ft
    • Built 1903

    Last Sold Summary

    • $99/SF
    • 40 Days On Market

    Current Estimated Value $384,572

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

    113 G St, Oakland, MD 21550
    • /69

      Est $459,365

      Not Listed For Sale

      1014 Madison St, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 3,016 Sq Ft
      • Built 1988
      1014 Madison St, Oakland, MD 21550

      Last Sold Summary

      • 21 Days On Market

  • /64

    $1,400,000

    • 5 Beds
    • 3.5 Baths
    • 2,832 Sq Ft

    827 Penn Point Rd, Oakland, MD 21550

    Custom built by the original owners and thoughtfully expanded with a recent addition, this exceptional five-bedroom, 3.5-bath home is set on 100 feet of split lakefront in desirable Penn Cove. Featuring a coveted Type A dock permit, lakeside fire pit and pavilion, and easy shoreline access, the property is designed to embrace lake living in every season. Set on a generously sized lot with

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

    827 Penn Point Rd, Oakland, MD 21550
  • /31

    $189,000

    Sold Jul 24, 2025

    1681 Shady Dell Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1985

    Last Sold Summary

    • $197/SF
    • 2 Days On Market

    Current Estimated Value $181,188

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

    1681 Shady Dell Rd, Oakland, MD 21550
    • /24

      Est $705,538

      Not Listed For Sale

      8 Arrowhead Ln, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • Built 1988
      8 Arrowhead Ln, Oakland, MD 21550

      Last Sold Summary

      • 80 Days On Market

Showing Results 441 - 480, Page 12 of 18

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