10,739

Oakland, MD Homes

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  • /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
  • /32

    $1,699,900 Sold May 23, 2025

    2353 Boy Scout Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 3,096 Sq Ft
    • Built 1940

    Last Sold Summary

    • $549/SF
    • 6 Days On Market

    Current Estimated Value $1,791,590

    Last Listing Agent Jon Bell Railey Realty, Inc.

    2353 Boy Scout Rd, Oakland, MD 21550
    • /7

      Not Listed For Sale

      Lot 5 Bobcat Hill Ln, Oakland, MD 21550

      Lot 5 Bobcat Hill Ln, Oakland, MD 21550

      Last Sold Summary

      • 43 Days On Market

      Last Sold Price $90,000

      Last Listing Agent Kim Palmer Marquee Properties, Inc.

  • /53

    $509,000

    • 4 Beds
    • 4.5 Baths
    • 3,192 Sq Ft

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550

    Welcome to this 4-bedroom, 4.5-bath stand-alone, multi-level unit in Traders Landing! Offering filtered lake views, ample square footage, oversized bedrooms, and multiple living spaces, this property is ideal for entertaining, large groups, or relaxed mountain-lake living. Enjoy a central Deep Creek location just minutes from Deep Creek Lake, local restaurants, shopping, and Wisp Resort.

    Nina Beitzel Railey Realty, Inc.

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
  • /25

    $42,000 Sold Aug 06, 2025

    Lot 18 Moss Creek Cir, Oakland, MD 21550

    • Land
    • 3.61 Acres
    • $11,634 per Acre

    Last Sold Summary

    • 58 Days On Market

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    Lot 18 Moss Creek Cir, Oakland, MD 21550
    • /7

      Not Listed For Sale

      25 Acres Lot D Bailiff Ln, Oakland, MD 21550

      25 Acres Lot D Bailiff Ln, Oakland, MD 21550

      Last Sold Summary

      • 20 Days On Market

      Last Sold Price $115,000

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • /32

    $309,000

    • 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
  • /65

    $280,500 Sold Sep 12, 2025

    290 Crellin Underwood Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,208 Sq Ft
    • Built 1982

    Last Sold Summary

    • $127/SF
    • 96 Days On Market

    Current Estimated Value $288,775

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    290 Crellin Underwood Rd, Oakland, MD 21550
    • /82

      Est $1,224,660 Not Listed For Sale

      20476 Garrett Hwy, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 2,635 Sq Ft
      • Built 1998
      20476 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 6% Above List Price
      • $436/SF
      • 53 Days On Market

      Last Sold Price $1,150,000

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /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

    333 Sloan Tract Rd, Oakland, MD 21550
  • /41

    $239,900 Sold Sep 12, 2025

    502 E Oak St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1956

    Last Sold Summary

    • $143/SF
    • 17 Days On Market

    Current Estimated Value $246,217

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    502 E Oak St, Oakland, MD 21550
    • /10

      Not Listed For Sale

      0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550

      0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550

      Last Sold Summary

      Last Sold Price $965,000

      Last Listing Agent Afrouz Homayouni Keller Williams Capital Properties

  • /67

    $525,000

    • 2 Beds
    • 2 Baths
    • 4,720 Sq Ft

    355 Lonesome Pine Rd, Oakland, MD 21550

    Welcome to your own slice of paradise—this stunning home sits on 84 breathtaking acres with incredible water frontage, offering unmatched privacy and a true connection to nature. Step inside and be captivated by walls of windows that flood the home with natural light, creating a warm and inviting atmosphere throughout the expansive living spaces. Whether you're entertaining or simply relaxing,

    Sheila Howell Lake Homes Realty, LLC

    355 Lonesome Pine Rd, Oakland, MD 21550
  • /97

    $732,500 Sold Jun 09, 2025

    116 Wanderer Ln Unit F5, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1975

    Last Sold Summary

    • $509/SF
    • 6 Days On Market

    Current Estimated Value $718,486

    Last Listing Agent Charlene Deremer Coldwell Banker Home Town Realty

    116 Wanderer Ln Unit F5, Oakland, MD 21550
    • /10

      Not Listed For Sale

      TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550

      TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550

      Last Sold Summary

      • 42 Days On Market

      Last Sold Price $414,100

      Last Listing Agent Kaleb Hurley Hurley Real Estate & Auctions

  • /43

    $555,000

    • 4 Beds
    • 3.5 Baths
    • 2,430 Sq Ft

    24 Trailside Way, Oakland, MD 21550

    Tucked in the Silver Ridge community at Deep Creek Lake, this inviting home blends rustic charm with comfortable modern living. Community trails and shared green space offer opportunities for outdoor recreation, while the wooded setting behind the home provides a sense of privacy and a peaceful natural backdrop. Step inside to an interior that reflects its surroundings, where warm wood accents,

    Jackie Ball Daley Northrop Realty

    24 Trailside Way, Oakland, MD 21550
  • /53

    $495,000 Sold Oct 08, 2025

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,422 Sq Ft
    • Built 2004

    Last Sold Summary

    • $204/SF
    • 106 Days On Market

    Current Estimated Value $496,003

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

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    • /37

      Not Listed For Sale

      278 Basswood Way Unit 19, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 3,084 Sq Ft
      • Built 2005
      278 Basswood Way Unit 19, Oakland, MD 21550

      Last Sold Summary

      • $232/SF
      • 87 Days On Market

      Last Sold Price $715,000

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

  • /11

    $199,900

    • Land
    • 0.11 Acre
    • $1,817,273 per Acre

    2 Overlook Ridge Dr S, Oakland, MD 21550

    Enjoy the best the lake has to offer from 'Overlook Ridge'! Boasting year-round lake views, yet tucked away in a peaceful and serene community setting. Short drive to the community lake access area for swimming and fishing! Dock Slips may be leased through HOA. Utilities to site and ready to build your perfect four-season Deep Creek getaway. Located just off of Rt. 219, with easy access to all

    Jon Bell Railey Realty, Inc.

    2 Overlook Ridge Dr S, Oakland, MD 21550
  • /65

    $375,000 Sold Jul 29, 2025

    5154 Maryland Hwy, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 2,860 Sq Ft
    • Built 1980

    Last Sold Summary

    • $131/SF
    • 23 Days On Market

    Current Estimated Value $399,881

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

    5154 Maryland Hwy, Oakland, MD 21550
    • /47

      Est $319,373 Not Listed For Sale

      33 Laurel Brook Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,120 Sq Ft
      • Built 1989
      33 Laurel Brook Dr, Oakland, MD 21550

      Last Sold Summary

      • 10% Above List Price
      • $137/SF
      • 48 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Rebekah Durst Taylor Made Deep Creek Real Estate

  • /38

    $297,500

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    505 Southern Pines Dr, Oakland, MD 21550

    Charming ranch-style home located in the desirable Southern Pines neighborhood. From the moment you enter, you’ll appreciate the warm and inviting feel of the open layout. The main level features three comfortable bedrooms, two full bathrooms, beautiful hardwood flooring, and a seamless kitchen, living, and dining area that creates an ideal space for everyday living and entertaining. The recently

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    505 Southern Pines Dr, Oakland, MD 21550
  • /67

    $760,000 Sold Nov 14, 2025

    62 Middleton Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,397 Sq Ft
    • Built 1993

    Last Sold Summary

    • $317/SF
    • 113 Days On Market

    Current Estimated Value $793,175

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Middleton Rd, Oakland, MD 21550
    • /64

      Est $1,720,730 Not Listed For Sale

      1200 Mountainview Dr, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 5,926 Sq Ft
      • Built 1998
      1200 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 8% Above List Price
      • $269/SF
      • 78 Days On Market

      Last Sold Price $1,594,000

      Last Listing Agent Adam Foote Keller Williams Realty Centre

  • /103

    $2,399,000

    • 7 Beds
    • 5 Baths
    • 4,691 Sq Ft

    41 Boyd Paugh Ln, Oakland, MD 21550

    Gorgeous 7 bedroom home with dock slip! This newer construction home sits on a quiet corner of Deep Creek Lake with 200 feet of lake frontage. Located in the beautiful and quiet Heron Cove community and comes with two community lake access points, one with a sandy beach area, tennis courts, and walking trails. The level lot is surrounded by trees and designed for privacy and outdoor enjoyment,

    Rachel Bruch Railey Realty, Inc.

    41 Boyd Paugh Ln, Oakland, MD 21550
  • /63

    $920,000 Sold Aug 22, 2025

    254 Middleton Rd, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 2,400 Sq Ft
    • Built 1994

    Last Sold Summary

    • $383/SF
    • 19 Days On Market

    Current Estimated Value $956,606

    Last Listing Agent Jon Bell Railey Realty, Inc.

    254 Middleton Rd, Oakland, MD 21550
    • /21

      Est $272,510 Not Listed For Sale

      35 Weber Ct, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 2009
      35 Weber Ct, Oakland, MD 21550

      Last Sold Summary

      • 9% Above List Price
      • $149/SF
      • 159 Days On Market

      Last Sold Price $250,000

      Last Listing Agent Linda Deremer Appalachian Realty

  • /31

    $1,650,000

    • 4 Beds
    • 6 Baths
    • 5,117 Sq Ft

    3898 Underwood Rd, Oakland, MD 21550

    Unique luxury home on 23 acres with 360 degree views of Pleasant Valley. 5,100 + SQ. FT. 4 ensuite bedrooms, 2 additional powder rooms, formal living room/ballroom, informal living room, sunroom, den, pantry and large dine in kitchen. 4 fireplaces. full basement, 3 car attached garage. Whole home generator. Everything in this home is first rate. A must see for the discerning buyer

    Robert Custer Custer Realty & Auction

    3898 Underwood Rd, Oakland, MD 21550
  • /33

    $150,000 Sold Dec 17, 2025

    111 Knoll Crest Heights Dr, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 3,504 Sq Ft
    • Built 1971

    Last Sold Summary

    • $43/SF
    • 48 Days On Market

    Current Estimated Value $162,727

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

    111 Knoll Crest Heights Dr, Oakland, MD 21550
    • /4

      Est $3,218,673 Not Listed For Sale

      214 McComas Beach Terrace, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 6,890 Sq Ft
      • Built 2010
      214 McComas Beach Terrace, Oakland, MD 21550

      Last Sold Summary

      • 4% Above List Price
      • $450/SF

      Last Sold Price $3,100,000

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /56

    $339,000

    • 5 Beds
    • 3.5 Baths
    • 3,682 Sq Ft

    697 Monte Vista Rd, Oakland, MD 21550

    Tucked away just minutes from downtown Oakland, MD, lies a home that truly surprises with over 3,500 sq. ft. of living space on 1.88 acres with breathtaking farm and mountain views. Step inside the main level, where the master suite awaits along with two additional large bedrooms and a full bath, plus a mudroom area with a convenient half bath—perfect for entertaining. Cozy evenings are made even

    Laura Newhall Taylor Made Deep Creek Real Estate

    697 Monte Vista Rd, Oakland, MD 21550
  • /43

    $460,000 Sold Oct 24, 2025

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,200 Sq Ft
    • Built 2009

    Last Sold Summary

    • $209/SF
    • 16 Days On Market

    Current Estimated Value $464,485

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    • /72

      Est $636,986 Not Listed For Sale

      145 Ridgewood Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 3,838 Sq Ft
      • Built 1999
      145 Ridgewood Dr, Oakland, MD 21550

      Last Sold Summary

      • 10% Above List Price
      • $151/SF
      • 1 Day On Market

      Last Sold Price $580,000

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /10

    $995,000

    • Land
    • 0.58 Acre
    • $1,715,517 per Acre

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550

    RARE OPPURTUNITY! Discover one of the final opportunities to own true lakefront on the iconic Glendale Road! This premier homesite offers approximately 75 feet of pristine Deep Creek Lake frontage in a serene no wake zone, perfect for swimming, kayaking, and peaceful lakeside enjoyment. Zoning in this area is Town Center. This allows for a larger building area within the lot with relaxed

    Lucas Muenchow Railey Realty, Inc.

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
  • /32

    $139,000 Sold Aug 15, 2025

    4960 Hutton Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • Built 1971

    Last Sold Summary

    • $129/SF
    • 205 Days On Market

    Current Estimated Value $142,768

    Last Listing Agent Justin Liller Railey Realty, Inc.

    4960 Hutton Rd, Oakland, MD 21550
    • /61

      Est $248,487 Not Listed For Sale

      4368 Underwood Rd, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 1,760 Sq Ft
      • Built 1952
      4368 Underwood Rd, Oakland, MD 21550

      Last Sold Summary

      • 15% Above List Price
      • $122/SF
      • 8 Days On Market

      Last Sold Price $215,500

      Last Listing Agent Sandy Bello Taylor Made Deep Creek Real Estate

  • /27

    $229,900

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 106B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs in a gas fireplace, full bath with tub/shower, and a tidy kitchenette with microwave, dishwasher, and full fridge. Balcony doors open to Deep Creek air and filtered lake scenes. Community perks include sauna, gym, game room and more. Sold turn-key, fully furnished. Ductless units for heat and A/C. Monthly

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 106B, Oakland, MD 21550
  • /72

    $310,000 Sold Jun 18, 2025

    202 Deerfield Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,720 Sq Ft
    • Built 1987

    Last Sold Summary

    • $114/SF
    • 128 Days On Market

    Current Estimated Value $340,555

    Last Listing Agent Sharon Murray Coldwell Banker Home Town Realty

    202 Deerfield Dr, Oakland, MD 21550
    • /83

      Est $1,561,652 Not Listed For Sale

      2203 Lake Shore Dr, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,403 Sq Ft
      • Built 1984
      2203 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 1% Above List Price
      • $645/SF
      • 20 Days On Market

      Last Sold Price $1,550,000

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • /42

    $245,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft

    13 Laurel Brook Dr, Oakland, MD 21550

    Affordable well maintained 2 Bedroom 2 Bath townhouse style condominium less than 1 mile from Deep Creek Lake. Offering low maintenance and a pleasant setting, the property works well for full and part time ownership. The unit offers recent upgrades and Includes 2 parking spaces along with public water, sewer and weekly trash pickup. Shown by appointment only.

    Bill Weissgerber Railey Realty, Inc.

    13 Laurel Brook Dr, Oakland, MD 21550

Showing Results 121 - 160, Page 4 of 18

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