10,739

Oakland, MD Homes

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    • /32

      Est $596,391 Not Listed For Sale

      1519 Mayhew Inn Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft
      • Built 2000
      1519 Mayhew Inn Rd, Oakland, MD 21550

      Last Sold Summary

      • 20% Above List Price
      • $340/SF
      • 9 Days On Market

      Last Sold Price $495,000

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

  • /47

    $589,000

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

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550

    Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lake has to offer, Whispering Pines is the ultimate turnkey mountain retreat. This impeccably maintained 5-bedroom townhome spans three levels of inviting living space and features an attached garage—perfect for hosting family, friends, or guests year-round. Enjoy the best of both worlds: a private, serene

    Nina Beitzel Railey Realty, Inc.

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
  • /37

    $250,000 Sold Dec 31, 2025

    511 E Green St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft
    • Built 1924

    Last Sold Summary

    • $133/SF
    • 176 Days On Market

    Current Estimated Value $250,896

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Real Estate

    511 E Green St, Oakland, MD 21550
    • /21

      Est $497,784 Not Listed For Sale

      471 Clifton Dr, Oakland, MD 21550

      • 5 Beds
      • 2 Baths
      • 3,612 Sq Ft
      • Built 1971
      471 Clifton Dr, Oakland, MD 21550

      Last Sold Summary

      • 31% Above List Price
      • $105/SF
      • 18 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /12

    $45,000

    • Land
    • 0.34 Acre
    • $132,353 per Acre

    LOT 181 Santa fe Trail, Oakland, MD 21550

    Don't miss the opportunity to own a lake area lot near the one and only Deep Creek Lake. 0.34 acre wooded lot, close to multiple local attractions. Call today! Verify utilities with Garrett County Environmental Department. Being sold subject to successful perc.

    Amy Skipper Railey Realty, Inc.

    LOT 181 Santa fe Trail, Oakland, MD 21550
  • /2

    $25,000 Sold Apr 24, 2025

    Lot 24 Laurel Dr, Oakland, MD 21550

    • Land
    • 0.58 Acre
    • $43,103 per Acre

    Last Sold Summary

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

    Lot 24 Laurel Dr, Oakland, MD 21550
    • /42

      Est $450,470 Not Listed For Sale

      426 Pergin Farm Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,596 Sq Ft
      • Built 1985
      426 Pergin Farm Rd, Oakland, MD 21550

      Last Sold Summary

      • 5% Above List Price
      • $269/SF
      • 15 Days On Market

      Last Sold Price $430,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /4

    $29,900

    • Land
    • 1.09 Acres
    • $27,431 per Acre

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550

    1+ acre building lot. Fairly leveled cleared lot with some distant mountain views. Paved County road frontage with private road/drive access to lot. Approved for private septic and well. Electric on-site. Located approx. 10+ mins from Deep Creek Lake and approx. less than 5 minutes from Oakland. Located within small 8 lot development, "The Homestead".

    Chip Smith 1 Real Estate Source LLC

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
  • /98

    $590,000 Sold Oct 10, 2025

    2719 Broadford Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 4,253 Sq Ft
    • Built 1984

    Last Sold Summary

    • $139/SF
    • 168 Days On Market

    Current Estimated Value $591,570

    Last Listing Agent Rich Orr Railey Realty, Inc.

    2719 Broadford Rd, Oakland, MD 21550
    • /81

      Est $684,057 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

      • 2% Below List Price
      • $239/SF
      • 148 Days On Market

      Last Sold Price $699,000

      Last Listing Agent Brian Homberg Taylor Made Deep Creek Real Estate

  • /53

    $349,999

    • 3 Beds
    • 1 Bath
    • 990 Sq Ft

    931 Black Oak Dr, Oakland, MD 21550

    Very motivated sellers!!!Escape to Your Profitable Mountain Sanctuary: The Yough Mountain CabinUnveiling the Ultimate Turnkey Retreat & High-Performing InvestmentNestled in the breathtaking heart of the exclusive Yough Mountain Resort, this stunning 3-bedroom cabin offers the perfect harmony of rustic soul and modern investment savvy. Whether you are looking for a private family getaway

    ANGELA BOSLEY Taylor Made Deep Creek Real Estate

    931 Black Oak Dr, Oakland, MD 21550
  • /47

    $405,000 Sold Aug 08, 2025

    343 Maple Del Ln, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,404 Sq Ft
    • Built 1993

    Last Sold Summary

    • $288/SF
    • 3 Days On Market

    Current Estimated Value $417,253

    Last Listing Agent Julie Mead The KW Collective

    343 Maple Del Ln, Oakland, MD 21550
    • /16

      Est $75,466 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

      • 54% Above List Price
      • $51/SF
      • 1 Day On Market

      Last Sold Price $49,000

      Last Listing Agent Adrianne Thompson Coldwell Banker Premier

  • /8

    $17,000 Pending

    • Land
    • 0.77 Acre
    • $22,078 per Acre

    Lot 40 W Big Piney Dr, Oakland, MD 21550

    Located in the Youghiogheny Mountain Resort community, this .77ac lot offers the ultimate gateway to peaceful surroundings, beautiful views, and abundant wildlife. Approved for a sand mound sewage system, this lot provides the perfect opportunity to build your future outdoor enthusiast retreat! Enjoy exclusive access to over 50 miles of private roads and trails perfect for ATV and side-by-side

    Elizabeth Broadwater Taylor Made Deep Creek Real Estate

    Lot 40 W Big Piney Dr, Oakland, MD 21550
  • /29

    $185,000 Sold Jan 23, 2026

    141 Truesdale Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,834 Sq Ft
    • Built 1988

    Last Sold Summary

    • $101/SF
    • 4 Days On Market

    Current Estimated Value $196,286

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

    141 Truesdale Rd, Oakland, MD 21550
    • /44

      Est $713,224 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

      • 13% Above List Price
      • $218/SF
      • 5 Days On Market

      Last Sold Price $632,501

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • /60

    $799,900

    • 4 Beds
    • 3.5 Baths
    • 3,780 Sq Ft

    467 Paradise Ridge Rd, Oakland, MD 21550

    Panoramic mountain and lake views set the tone at this lake access home in Paradise Ridge, one of Deep Creek’s most sought-after communities! Perched at the top of the hill on 1.29 acres, this 4-bedroom, 3 full and 1 half bath retreat offers 3,780 finished square feet across three levels. Abundant glass frames the surrounding ridgelines with views of Deep Creek Lake from every room in the house!

    Jon Bell Railey Realty, Inc.

    467 Paradise Ridge Rd, Oakland, MD 21550
  • /88

    $1,145,000 Sold Apr 29, 2025

    324 Penn Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 3,820 Sq Ft
    • Built 2004

    Last Sold Summary

    • $300/SF
    • 7 Days On Market

    Current Estimated Value $1,188,226

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

    324 Penn Cove Rd, Oakland, MD 21550
    • /81

      Est $831,338 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

      • 11% Above List Price
      • $238/SF
      • 29 Days On Market

      Last Sold Price $749,000

      Last Listing Agent Larry Smith Railey Realty, Inc.

  • /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
  • /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 $919,034

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

    78 Mountainside Ct, Oakland, MD 21550
    • /56

      Est $547,742 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% Above List Price
      • $231/SF
      • 10 Days On Market

      Last Sold Price $500,000

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

  • /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

    315 Coolidge Ave, 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 $899,138

    Last Listing Agent Jon Bell Railey Realty, Inc.

    340 Grandview Dr, Oakland, MD 21550
    • /125

      Est $2,244,258 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

      • 8% Below List Price
      • $534/SF
      • 3 Days On Market

      Last Sold Price $2,450,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /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

    231 Santa fe Trail, 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 $421,286

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    15 Village Dr Unit 1, Oakland, MD 21550
    • /65

      Est $3,934,340 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

      • 7% Above List Price
      • $434/SF
      • 0 Days On Market

      Last Sold Price $3,670,000

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

  • /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
  • /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 $461,416

    Last Listing Agent Larry Smith Railey Realty, Inc.

    783 Mountainview Dr, Oakland, MD 21550
    • /56

      Est $393,903 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

      • 11% Above List Price
      • $217/SF
      • 24 Days On Market

      Last Sold Price $355,000

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /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
  • /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 $374,506

    Last Listing Agent Tim Macauley Taylor Made Deep Creek Real Estate

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

      Est $155,350 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

      • 55% Above List Price
      • $60/SF
      • 81 Days On Market

      Last Sold Price $100,000

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

  • /48

    $199,900

    • 2 Beds
    • 1 Bath
    • 1,492 Sq Ft

    207 Shenandoah Ave, Oakland, MD 21550

    Fall in love with this charming 2-bedroom, 1-bath home in Loch Lynn, tucked on a 0.25-acre lot with a private wood-fenced side yard and a covered sundeck perfect for morning coffee or evening gatherings. Thoughtfully updated with refinished floors, quartz countertops, new appliances, and cozy touches throughout, it’s move-in ready and effortlessly welcoming. Enjoy modern convenience with a smart

    Laura Newhall Taylor Made Deep Creek Real Estate

    207 Shenandoah Ave, 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 $233,922

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    5202 Hutton Rd, Oakland, MD 21550
    • /76

      Est $213,654 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

      • 7% Above List Price
      • $79/SF

      Last Sold Price $200,000

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /6

    $875,000 Coming Soon

    • 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, 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 fireplace. The

    Brent Housley Railey Realty, Inc.

    891 Mountainview Dr, Oakland, MD 21550
  • /13

    $20,000 Sold Nov 05, 2025

    0 Weber Ct, Oakland, MD 21550

    • Land
    • 0.24 Acre
    • $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
    • /35

      Est $365,315 Not Listed For Sale

      107 Pleasant Hill Cir, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,384 Sq Ft
      • Built 1989
      107 Pleasant Hill Cir, Oakland, MD 21550

      Last Sold Summary

      • 30% Above List Price
      • $117/SF

      Last Sold Price $280,000

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

Showing Results 321 - 360, Page 9 of 18

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