10,771

Oakland, MD Homes

Section Image
  • /50

    $567,500

    Sold Mar 13, 2026

    189 Red Run Rd Unit 1C2, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Below List Price
    • $473/SF
    • 227 Days On Market

    Current Estimated Value $545,073

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

    189 Red Run Rd Unit 1C2, Oakland, MD 21550
    • /47

      Est $547,788

      Not Listed For Sale

      38 Traders Ln, Oakland, MD 21550

      • 4 Beds
      • 4.5 Baths
      • 2,582 Sq Ft
      • Built 2003
      38 Traders Ln, Oakland, MD 21550

      Last Sold Summary

      • 22 Days On Market

  • /30

    $249,000

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,390 Sq Ft

    62 Wild Turkey Ct, Oakland, MD 21550

    Current new home construction project underway, but Builder not going to complete at this time due too busy. So, ready for who may wish to complete project themselves or have completed by others, or current Builder may consider completing for Buyer. Current structure is a custom engineered modular home. This is not a completed or intended by Builder to be completed house project at this time .

    Chip Smith 1 Real Estate Source LLC

    62 Wild Turkey Ct, Oakland, MD 21550
  • /67

    $1,542,000

    Sold Nov 13, 2025

    1567 Pergin Farm Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,200 Sq Ft
    • Built 2002

    Last Sold Summary

    • $482/SF
    • 15 Days On Market

    Current Estimated Value $1,485,782

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1567 Pergin Farm Rd, Oakland, MD 21550
    • /82

      Est $2,388,223

      Not Listed For Sale

      1983 Lake Shore Dr, Oakland, MD 21550

      • 5 Beds
      • 6.5 Baths
      • 4,074 Sq Ft
      • Built 2000
      1983 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 236 Days On Market

  • /53

    $269,500

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    315 Coolidge Ave, Oakland, MD 21550

    Well maintained brick rancher located in the heart of Oakland. This home offers a large kitchen open to the living room with a built-in fireplace, separate dining room, and new carpet through out. The basement is very clean, offering a clean slate for whatever you would like to do. The rear covered porch, deck and fenced in yard makes a great space to enjoy family and friends. The location is

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

    315 Coolidge Ave, Oakland, MD 21550
  • /10

    $59,000

    Sold Jun 26, 2025

    Lot 9 Pheasant Run, Oakland, MD 21550

    • Land
    • 6.22 Acres
    • $9,486 per Acre

    Last Sold Summary

    • 15 Days On Market

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    Lot 9 Pheasant Run, Oakland, MD 21550
    • /76

      Est $983,217

      Not Listed For Sale

      1865 Paradise Point Rd, Oakland, MD 21550

      • 6 Beds
      • 3.5 Baths
      • 2,158 Sq Ft
      • Built 2005
      1865 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

  • /28

    $335,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,288 Sq Ft

    1740 Old Crellin Rd, Oakland, MD 21550

    Come see this beautifully maintained 3-bedroom, 3-bath Colonial-style residence nestled on a private 1-acre lot along Old Crellin Road in Oakland. Offering 2,300 square feet of living space, this home combines classic charm with modern comfort in an ideal location just outside town limits. Step inside to find a spacious and inviting layout, perfect for both everyday living and entertaining. The

    Andrew Orr The KW Collective

    1740 Old Crellin Rd, Oakland, MD 21550
  • /50

    $295,000

    Sold May 20, 2026

    163 Crestview Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,416 Sq Ft
    • Built 1997

    Last Sold Summary

    • $208/SF
    • 275 Days On Market

    Current Estimated Value $307,945

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

    163 Crestview Dr, Oakland, MD 21550
    • /39

      Est $202,940

      Not Listed For Sale

      227 W Liberty St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,232 Sq Ft
      • Built 1910
      227 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 44 Days On Market

  • /37

    $629,000

    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft

    231 Santa fe Trail, Oakland, MD 21550

    3/4BR 3BA chalet with LAKE VIEWS! 2300sf vacation home fronting on a mountain stream, overlooking Deep Creek Lake! Enjoy an eat-in kitchen, exposed beams and a loft area that the current owners use as a 4th BR with bathroom. NO HOA! Conveys fully furnished. Features include central AC, exposed beams, updated flooring, gas fireplace on main level, lower level rec room with pool table and

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    231 Santa fe Trail, Oakland, MD 21550
  • /65

    $537,000

    Sold Feb 27, 2026

    77 Meadow Ct, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,436 Sq Ft
    • Built 2006

    Last Sold Summary

    • $220/SF
    • 100 Days On Market

    Current Estimated Value $567,490

    Last Listing Agent Jon Bell Railey Realty, Inc.

    77 Meadow Ct, Oakland, MD 21550
    • /61

      Est $808,480

      Not Listed For Sale

      889 Paradise Ridge Rd, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 3,004 Sq Ft
      • Built 2004
      889 Paradise Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 30 Days On Market

  • /53

    $260,000

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 103B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites! This inviting one-bedroom layout features a gas fireplace, full bath with tub/shower, and a tidy kitchenette equipped with a microwave, dishwasher, and full-size refrigerator. Balcony doors open to fresh Deep Creek air and filtered lake views, with a private deck that is perfect for relaxing after a day on the water. Enjoy a variety of

    Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 103B, Oakland, MD 21550
  • /60

    $505,000

    Sold Nov 14, 2025

    36 Ridgewood Dr, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 1,713 Sq Ft
    • Built 2000

    Last Sold Summary

    • $295/SF
    • 228 Days On Market

    Current Estimated Value $509,270

    Last Listing Agent Larry Smith Railey Realty, Inc.

    36 Ridgewood Dr, Oakland, MD 21550
    • /84

      Est $307,654

      Not Listed For Sale

      255 Foster Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,272 Sq Ft
      • Built 1962
      255 Foster Rd, Oakland, MD 21550

      Last Sold Summary

      • 11 Days On Market

  • /38

    $389,000

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    20160 Garrett Hwy Unit G507, Oakland, MD 21550

    Experience lakefront living with this charming two-level condo at Will O the Wisp at Deep Creek Lake! Offering 2 bedrooms and 1 full bathroom, it captures breathtaking lake views from both levels. The main floor features a functional kitchen and a cozy living area with a wood-burning fireplace—perfect for relaxing after a day on the water. Upstairs, you’ll find two comfortable bedrooms and a full

    Nina Beitzel Railey Realty, Inc.

    20160 Garrett Hwy Unit G507, Oakland, MD 21550
  • /24

    $85,000

    Sold Oct 03, 2025

    1101 Wheeling Ave, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,718 Sq Ft
    • Built 1950

    Last Sold Summary

    • $49/SF
    • 25 Days On Market

    Current Estimated Value $161,407

    Last Listing Agent Tanavia Greer Long & Foster Real Estate, Inc.

    1101 Wheeling Ave, Oakland, MD 21550
    • /64

      Est $223,558

      Not Listed For Sale

      324 W Liberty St, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,725 Sq Ft
      • Built 1900
      324 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /13

    $425,000

    • 3 Beds
    • 3.5 Baths
    • 1,596 Sq Ft

    104 Pine Top Trail, Oakland, MD 21550

    Here's your chance to purchase a cute Chalet with just about 7 acres. .This home and acreage is right next to the Common Grounds and gives you immediate river access.

    laura Flynn 1 Real Estate Source LLC

    104 Pine Top Trail, Oakland, MD 21550
  • /24

    $110,000

    Sold Sep 26, 2025

    110 W Pennington St, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1946

    Last Sold Summary

    • $143/SF
    • 12 Days On Market

    Current Estimated Value $115,976

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

    110 W Pennington St, Oakland, MD 21550
    • /83

      Est $1,196,805

      Not Listed For Sale

      2675 Stockslager Rd, Oakland, MD 21550

      • 4 Beds
      • 4.5 Baths
      • 3,024 Sq Ft
      • Built 2003
      2675 Stockslager Rd, Oakland, MD 21550

      Last Sold Summary

  • /7

    $15,000

    $15K PRICE DROP
    • Land
    • 40,075 Sq Ft
    • $16,304 per Acre

    0 Maryland Hwy Unit MDGA2011452, Oakland, MD 21550

    This is an estate listing. The parcel is 0.92 Acre that is wooded and vacant.The lot failed to Perc.

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    0 Maryland Hwy Unit MDGA2011452, Oakland, MD 21550
  • /50

    $425,000

    Sold Jun 03, 2026

    609 Southern Pines Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,250 Sq Ft
    • Built 1989

    Last Sold Summary

    • 8% Below List Price
    • $189/SF
    • 295 Days On Market

    Current Estimated Value $427,509

    Last Listing Agent Brian Covell BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    609 Southern Pines Dr, Oakland, MD 21550
    • /75

      Est $715,210

      Not Listed For Sale

      630 Paradise Ridge Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,044 Sq Ft
      • Built 1997
      630 Paradise Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /82

    $875,000

    Under Contract
    • 3 Beds
    • 4 Baths
    • 3,990 Sq Ft

    891 Mountainview Dr, Oakland, MD 21550

    Discover the perfect blend of rustic charm and modern comfort in this inviting turnkey 3‐bedroom mountaintop chalet with lake access, set on 1.17 private acres with expansive outdoor entertainment space. Whether you're hosting friends or enjoying quiet mountain evenings, this fully-furnished home delivers an unforgettable retreat. Inside, the great room impresses with a soaring stacked‐stone

    Brent Housley Railey Realty, Inc.

    891 Mountainview Dr, Oakland, MD 21550
  • /45

    $150,000

    Sold Aug 14, 2025

    414 D St, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft
    • Built 1950

    Last Sold Summary

    • $160/SF
    • 4 Days On Market

    Current Estimated Value $147,993

    Last Listing Agent Michelle Clark Taylor-Made Deep Creek Real Estate, LLC

    414 D St, Oakland, MD 21550
    • /4

      Est $106,113

      Not Listed For Sale

      111 W Liberty St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,528 Sq Ft
      • Built 1914
      111 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 10 Days On Market

  • /64

    $275,900

    • 4 Beds
    • 2 Baths
    • 1,928 Sq Ft

    449 S 3rd St, Oakland, MD 21550

    Welcome to this beautifully updated 1901 home in the heart of downtown Oakland, where historic character meets modern convenience. Situated on a charming lot with mature landscaping and blooming trees, this home offers timeless curb appeal with a welcoming covered front porch perfect for relaxing and enjoying the neighborhood. Inside, you’ll find modern updates throughout while preserving classic

    Justin Liller Railey Realty, Inc.

    449 S 3rd St, Oakland, MD 21550
  • /48

    $525,000

    Sold Jul 11, 2025

    3554 Lake Shore Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1993

    Last Sold Summary

    • $405/SF
    • 232 Days On Market

    Current Estimated Value $522,143

    Last Listing Agent Robert Krop Keller Williams Realty Centre

    3554 Lake Shore Dr, Oakland, MD 21550
    • /25

      Est $1,097,118

      Not Listed For Sale

      378 Lower Penn Point Dr, Oakland, MD 21550

      • 4 Beds
      • 1 Bath
      • 1,114 Sq Ft
      • Built 1950
      378 Lower Penn Point Dr, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • /18

    $3,000

    • Land
    • 24,393 Sq Ft
    • $5,357 per Acre

    Lot 40 Fawn Dr, Oakland, MD 21550

    Lot 40 Fawn Drive is a 0.56-acre wooded, NON-BUILDABLE membership lot located in Youghiogheny Mountain Resort community in Oakland, MD. This lot's ownership offers full membership access to the community’s amenities, including over 50 miles of private roads and trails perfect for ATV riding, UTVs, dirt bikes, hiking, and outdoor recreation. Ideal for outdoor enthusiasts seeking a private escape

    Shannon McWilliams Taylor-Made Deep Creek Real Estate, LLC

    Lot 40 Fawn Dr, Oakland, MD 21550
  • /22

    $185,000

    Sold May 22, 2026

    1307 Broadford Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • Built 2005

    Last Sold Summary

    • 11% Below List Price
    • $195/SF
    • 46 Days On Market

    Current Estimated Value $204,024

    Last Listing Agent Bill Kenny Keller Williams Realty Centre

    1307 Broadford Rd, Oakland, MD 21550
    • /89

      Est $1,657,590

      Not Listed For Sale

      1019 Lake Shore Dr, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 2,605 Sq Ft
      • Built 1962
      1019 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 1 Day On Market

  • /8

    $100,000

    $100K PRICE DROP
    • Land
    • 5 Acres
    • $20,000 per Acre

    3500 Area Maryland Hwy, Oakland, MD 21550

    The parcel is being sold by an estate. Wooded vacant land located at the 3400 area of Maryland Highway, Route 135. There is no record of Perc test on file at the Garrett County Health Department.

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    3500 Area Maryland Hwy, Oakland, MD 21550
  • /5

    $44,000

    Sold Aug 11, 2025

    142 Matthew Rd, Oakland, MD 21550

    • Land
    • 1.83 Acres
    • $24,044 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    142 Matthew Rd, Oakland, MD 21550
    • /65

      Est $152,722

      Not Listed For Sale

      94 Tannery Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,108 Sq Ft
      • Built 1900
      94 Tannery Rd, Oakland, MD 21550

      Last Sold Summary

      • 63 Days On Market

  • /52

    $499,900

    Pending
    • 4 Beds
    • 2 Baths
    • 1,296 Sq Ft

    247 Sloan Tract Rd, Oakland, MD 21550

    Welcome to 247 Sloan Tract Rd, a beautifully crafted 4-bedroom, 2-bath timber frame home at Deep Creek Lake! Built in 2004 and offering 1,296 finished living space, this 2-story residence showcases the exceptional craftsmanship by renowned builder Rex Anderson. Inside, you’ll find rich hardwood flooring, exposed beam ceilings, and stunning woodwork that create a warm and inviting mountain

    Mike Fenton Railey Realty, Inc.

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

    $229,000

    Sold Dec 15, 2025

    104 G St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft
    • Built 1900

    Last Sold Summary

    • $142/SF
    • 26 Days On Market

    Current Estimated Value $221,485

    Last Listing Agent Julie Mead The KW Collective

    104 G St, Oakland, MD 21550

Showing Results 401 - 440, Page 11 of 18

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