10,731

Oakland, MD Homes

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    • 139 Hunters Dr, Oakland, MD 21550
      139 Hunters Dr, Oakland, MD 21550
      139 Hunters Dr, Oakland, MD 21550
      /41

      Est $363,472 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,240 Sq Ft

      139 Hunters Dr, Oakland, MD 21550

      139 Hunters Dr, Oakland, MD 21550
  • 62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    /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
  • 123 Mountainview Ct, Oakland, MD 21550
    123 Mountainview Ct, Oakland, MD 21550
    123 Mountainview Ct, Oakland, MD 21550
    /20

    $200,000 Sold Feb 06, 2026

    123 Mountainview Ct, Oakland, MD 21550

    • Land
    • 1.69 Acres
    • $118,343 per Acre

    Last Sold Summary

    • 72 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    123 Mountainview Ct, Oakland, MD 21550
    • 320 Lake Forest Dr, Oakland, MD 21550
      320 Lake Forest Dr, Oakland, MD 21550
      320 Lake Forest Dr, Oakland, MD 21550
      /83

      Est $2,288,549 Not Listed For Sale

      • 6 Beds
      • 4.5 Baths
      • 2,363 Sq Ft

      320 Lake Forest Dr, Oakland, MD 21550

      320 Lake Forest Dr, Oakland, MD 21550
  • 315 Coolidge Ave, Oakland, MD 21550
    315 Coolidge Ave, Oakland, MD 21550
    315 Coolidge Ave, Oakland, MD 21550
    /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 Vacations & Sales

    315 Coolidge Ave, Oakland, MD 21550
  • 155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    /51

    $660,000 Sold Jan 30, 2026

    155 Basswood Way, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,792 Sq Ft
    • Built 2003

    Last Sold Summary

    • $236/SF
    • 268 Days On Market

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    155 Basswood Way, Oakland, MD 21550
    • 204 Farm View Ln, Oakland, MD 21550
      204 Farm View Ln, Oakland, MD 21550
      204 Farm View Ln, Oakland, MD 21550
      /95

      Est $555,635 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,268 Sq Ft

      204 Farm View Ln, Oakland, MD 21550

      204 Farm View Ln, Oakland, MD 21550
  • 20160 Garrett Hwy Unit G507, Oakland, MD 21550
    20160 Garrett Hwy Unit G507, Oakland, MD 21550
    20160 Garrett Hwy Unit G507, Oakland, MD 21550
    /34

    $399,000

    • 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
  • 341 Doe Dr, Oakland, MD 21550
    341 Doe Dr, Oakland, MD 21550
    341 Doe Dr, Oakland, MD 21550
    /40

    $410,000 Sold Feb 28, 2025

    341 Doe Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 2024

    Last Sold Summary

    • $237/SF
    • 189 Days On Market

    Current Estimated Value $415,668

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Vacations & Sales

    341 Doe Dr, Oakland, MD 21550
    • 144 Middleton Rd, Oakland, MD 21550
      144 Middleton Rd, Oakland, MD 21550
      144 Middleton Rd, Oakland, MD 21550
      /73

      Est $1,042,503 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,440 Sq Ft

      144 Middleton Rd, Oakland, MD 21550

      144 Middleton Rd, Oakland, MD 21550
  • 3.35 acres </> 4th St, Oakland, MD 21550
    3.35 acres </> 4th St, Oakland, MD 21550
    3.35 acres </> 4th St, Oakland, MD 21550
    /3

    $150,000

    • Land
    • 3.4 Acres
    • $44,118 per Acre

    3.35 acres </> 4th St, Oakland, MD 21550

    Just over three acres in a prime location in Oakland, Maryland. Property borders the south side of Wal-Mart property and has deeded access from the south entrance of Wal-Mart. Property is wooded but has several flat spots perfect for building. Owner has hired a civil engineer to draw plans for a restaurant, and an office building. Plans are available for review.

    Andrew Orr The KW Collective

    3.35 acres </> 4th St, Oakland, MD 21550
  • 511 E Green St, Oakland, MD 21550
    511 E Green St, Oakland, MD 21550
    511 E Green St, 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

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Vacations & Sales

    511 E Green St, Oakland, MD 21550
    • 2411 Lake Shore Dr, Oakland, MD 21550
      2411 Lake Shore Dr, Oakland, MD 21550
      2411 Lake Shore Dr, Oakland, MD 21550
      /58

      Est $1,537,110 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,200 Sq Ft

      2411 Lake Shore Dr, Oakland, MD 21550

      2411 Lake Shore Dr, Oakland, MD 21550
  • 170 San Francisco St, Oakland, MD 21550
    170 San Francisco St, Oakland, MD 21550
    170 San Francisco St, Oakland, MD 21550
    /12

    $129,900

    • Land
    • 1.38 Acres
    • $94,130 per Acre

    170 San Francisco St, Oakland, MD 21550

    NEW in the Deep Creek Lake and WISP Resort area: three lots at .46 acres each (total is 1.38 acres)! Whether you envision a cozy cabin or a luxury lodge, this parcel offers the ideal blend of seclusion and accessibility. Property Highlights: Private well water source already in place, 200 AMP electric service connection, Approved perc test suitable for a 4-5 bedroom home, Privacy with

    Hunter Shank Coldwell Banker Realty

    170 San Francisco St, Oakland, MD 21550
  • Lot 24 Laurel Dr, Oakland, MD 21550
    Lot 24 Laurel Dr, 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
    • 2524 Stockslager Rd, Oakland, MD 21550
      2524 Stockslager Rd, Oakland, MD 21550
      2524 Stockslager Rd, Oakland, MD 21550
      /132

      Est $3,857,053 Not Listed For Sale

      • 5 Beds
      • 7 Baths
      • 9,134 Sq Ft

      2524 Stockslager Rd, Oakland, MD 21550

      2524 Stockslager Rd, Oakland, MD 21550
  • 0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
    /24

    $248,500

    • Land
    • 3.32 Acres
    • $74,849 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
  • 2719 Broadford Rd, Oakland, MD 21550
    2719 Broadford Rd, Oakland, MD 21550
    2719 Broadford Rd, 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 $583,607

    Last Listing Agent Rich Orr Railey Realty, Inc.

    2719 Broadford Rd, Oakland, MD 21550
    • 1519 Mayhew Inn Rd, Oakland, MD 21550
      1519 Mayhew Inn Rd, Oakland, MD 21550
      1519 Mayhew Inn Rd, Oakland, MD 21550
      /32

      Est $586,179 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft

      1519 Mayhew Inn Rd, Oakland, MD 21550

      1519 Mayhew Inn Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit B206, Oakland, MD 21550
    565 Glendale Rd Unit B206, Oakland, MD 21550
    565 Glendale Rd Unit B206, Oakland, MD 21550
    /32

    $319,000

    • 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
  • 343 Maple Del Ln, Oakland, MD 21550
    343 Maple Del Ln, Oakland, MD 21550
    343 Maple Del Ln, 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 $407,331

    Last Listing Agent Julie Mead The KW Collective

    343 Maple Del Ln, Oakland, MD 21550
    • 471 Clifton Dr, Oakland, MD 21550
      471 Clifton Dr, Oakland, MD 21550
      471 Clifton Dr, Oakland, MD 21550
      /21

      Est $552,051 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 3,612 Sq Ft

      471 Clifton Dr, Oakland, MD 21550

      471 Clifton Dr, Oakland, MD 21550
  • 130 Mystic Creek Trail Unit 1B, Oakland, MD 21550
    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550
    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550
    /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
  • 141 Truesdale Rd, Oakland, MD 21550
    141 Truesdale Rd, Oakland, MD 21550
    141 Truesdale Rd, 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

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    141 Truesdale Rd, Oakland, MD 21550
    • 43 Robinwood Dr, Oakland, MD 21550
      43 Robinwood Dr, Oakland, MD 21550
      43 Robinwood Dr, Oakland, MD 21550
      /81

      Est $780,443 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,921 Sq Ft

      43 Robinwood Dr, Oakland, MD 21550

      43 Robinwood Dr, Oakland, MD 21550
  • 139 Overlook Ridge Dr, Oakland, MD 21550
    139 Overlook Ridge Dr, Oakland, MD 21550
    139 Overlook Ridge Dr, Oakland, MD 21550
    /72

    $875,000

    • 5 Beds
    • 4.5 Baths
    • 2,846 Sq Ft

    139 Overlook Ridge Dr, Oakland, MD 21550

    Perched atop Holiday Hill on a 1.5-acre site, you will find this contemporary home with beautiful views of Deep Creek Lake! Offering over 3,200 SF with an open floorplan and an abundance of windows, making this home feel warm and inviting while offering plenty of room to enjoy family and friends. Boasting four bedrooms, 3.5 baths, three levels of living space, hardwood flooring, two stone propane

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    139 Overlook Ridge Dr, Oakland, MD 21550
  • 324 Penn Cove Rd, Oakland, MD 21550
    324 Penn Cove Rd, Oakland, MD 21550
    324 Penn Cove 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 $1,164,967

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    324 Penn Cove Rd, Oakland, MD 21550
    • 36 Preston Ln, Oakland, MD 21550
      36 Preston Ln, Oakland, MD 21550
      36 Preston Ln, Oakland, MD 21550
      /16

      Est $66,479 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 964 Sq Ft

      36 Preston Ln, Oakland, MD 21550

      36 Preston Ln, Oakland, MD 21550
  • 711 Heritage Dr, Oakland, MD 21550
    711 Heritage Dr, Oakland, MD 21550
    711 Heritage Dr, Oakland, MD 21550
    /58

    $249,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    711 Heritage Dr, Oakland, MD 21550

    Welcome to easy living at this beautifully maintained 3-bedroom ranch-style home w/ attached heated garage. Updated Modern, spacious Kitchen area, Master BR Suite w/ private bath & walk in closet. Efficient gas forced-air heating w/ central air conditioning, ensuring year-round comfort in every season. Backing to trees, the home provides a peaceful, private setting while still being centrally

    Rich Orr Railey Realty, Inc.

    711 Heritage Dr, Oakland, MD 21550
  • 78 Mountainside Ct, Oakland, MD 21550
    78 Mountainside Ct, Oakland, MD 21550
    78 Mountainside 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

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    78 Mountainside Ct, Oakland, MD 21550
    • 870 Hunters Ridge Dr, Oakland, MD 21550
      870 Hunters Ridge Dr, Oakland, MD 21550
      870 Hunters Ridge Dr, Oakland, MD 21550
      /44

      Est $740,452 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,896 Sq Ft

      870 Hunters Ridge Dr, Oakland, MD 21550

      870 Hunters Ridge Dr, Oakland, MD 21550
  • 0 Bethlehem Rd, Oakland, MD 21550
    0 Bethlehem Rd, Oakland, MD 21550
    0 Bethlehem Rd, Oakland, MD 21550
    /4

    $51,000

    • Land
    • 7.02 Acres
    • $7,265 per Acre

    0 Bethlehem Rd, Oakland, MD 21550

    LOT B= 7.02 acre parcel, located off Bethlehem Rd, in Western Maryland! Adjoins lot A (8.73 acres) also for sale. Near Potomac State Forest, this country setting, offers level land, perfect for building a home or if you are looking for a recreational outdoor property, this is a perfect spot for your adventures. Located outside the town of Oakland, just 8 mins away from schools, shopping and

    Thomas Long Railey Realty, Inc.

    0 Bethlehem Rd, Oakland, MD 21550
  • 783 Mountainview Dr, Oakland, MD 21550
    783 Mountainview Dr, Oakland, MD 21550
    783 Mountainview Dr, 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 $458,184

    Last Listing Agent Larry Smith Railey Realty, Inc.

    783 Mountainview Dr, Oakland, MD 21550
    • 335 Mountainview Dr, Oakland, MD 21550
      335 Mountainview Dr, Oakland, MD 21550
      335 Mountainview Dr, Oakland, MD 21550
      /81

      Est $795,822 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,142 Sq Ft

      335 Mountainview Dr, Oakland, MD 21550

      335 Mountainview Dr, Oakland, MD 21550
  • 1909 Pysell Crosscut Rd, Oakland, MD 21550
    1909 Pysell Crosscut Rd, Oakland, MD 21550
    1909 Pysell Crosscut Rd, Oakland, MD 21550
    /82

    $865,000

    • 4 Beds
    • 4.5 Baths
    • 2,970 Sq Ft

    1909 Pysell Crosscut Rd, Oakland, MD 21550

    Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just minutes from Deep Creek Lake and Oakland. This 4-bedroom, 4.5-bath home has been carefully updated to balance comfort, practicality, and modern style.The main level features hardwood floors, radiant heat for added comfort, and open gathering spaces with quiet nooks for reading or hobbies. Upstairs,

    Melissa Long Railey Realty, Inc.

    1909 Pysell Crosscut Rd, Oakland, MD 21550
  • 20160 Garrett Hwy Unit G509, Oakland, MD 21550
    20160 Garrett Hwy Unit G509, Oakland, MD 21550
    20160 Garrett Hwy Unit G509, 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 $387,854

    Last Listing Agent Tim Macauley Taylor Made Deep Creek Vacations & Sales

    20160 Garrett Hwy Unit G509, Oakland, MD 21550
    • 741 Hoyes Run Rd, Oakland, MD 21550
      741 Hoyes Run Rd, Oakland, MD 21550
      741 Hoyes Run Rd, Oakland, MD 21550
      /56

      Est $541,483 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,160 Sq Ft

      741 Hoyes Run Rd, Oakland, MD 21550

      741 Hoyes Run Rd, Oakland, MD 21550
  • 63 Wallman Rd, Oakland, MD 21550
    63 Wallman Rd, Oakland, MD 21550
    63 Wallman Rd, Oakland, MD 21550
    /60

    $179,900

    • 3 Beds
    • 1 Bath
    • 816 Sq Ft

    63 Wallman Rd, Oakland, MD 21550

    Remodeled Rancher Near the North Branch Potomac RiverThis charming 3-bedroom, 1-bath rancher has been completely remodeled, with all new appliances. Located within walking distance of the scenic North Branch of the Potomac River, the home offers both convenience and natural beauty at your doorstep.A recently enclosed front porch with a wood stove provides extra warmth and a welcoming spot

    Rich Orr Railey Realty, Inc.

    63 Wallman Rd, Oakland, MD 21550
  • 0 Weber Ct, Oakland, MD 21550
    0 Weber Ct, Oakland, MD 21550
    0 Weber Ct, 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
    • 427 Lake Shore Dr, Oakland, MD 21550
      427 Lake Shore Dr, Oakland, MD 21550
      427 Lake Shore Dr, Oakland, MD 21550
      /125

      Est $2,416,418 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,584 Sq Ft

      427 Lake Shore Dr, Oakland, MD 21550

      427 Lake Shore Dr, Oakland, MD 21550

Showing Results 321 - 360, Page 9 of 18

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