10,714

Oakland, MD Homes

Section Image
    • 153 Mallard Loop, Oakland, MD 21550
      153 Mallard Loop, Oakland, MD 21550
      153 Mallard Loop, Oakland, MD 21550
      /91

      Est $1,357,077 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,506 Sq Ft

      153 Mallard Loop, Oakland, MD 21550

      153 Mallard Loop, 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
  • 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

    Last Listing Agent Rich Orr Railey Realty, Inc.

    2719 Broadford Rd, Oakland, MD 21550
    • 22 Duck Cove Rd, Oakland, MD 21550
      22 Duck Cove Rd, Oakland, MD 21550
      22 Duck Cove Rd, Oakland, MD 21550
      /70

      Est $1,769,694 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 1,964 Sq Ft

      22 Duck Cove Rd, Oakland, MD 21550

      22 Duck Cove Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit 103B, Oakland, MD 21550
    565 Glendale Rd Unit 103B, Oakland, MD 21550
    565 Glendale Rd Unit 103B, Oakland, MD 21550
    /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
  • 96 Bobcat Hill Ln, Oakland, MD 21550
    96 Bobcat Hill Ln, Oakland, MD 21550
    96 Bobcat Hill Ln, Oakland, MD 21550
    /74

    $862,500 Sold Jan 07, 2025

    96 Bobcat Hill Ln, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 3,263 Sq Ft
    • Built 2018

    Last Sold Summary

    • $264/SF
    • 101 Days On Market

    Current Estimated Value $915,552

    Last Listing Agent Kim Palmer Marquee Properties, Inc.

    96 Bobcat Hill Ln, Oakland, MD 21550
    • 10 Ortiz Ct, Oakland, MD 21550
      10 Ortiz Ct, Oakland, MD 21550
      10 Ortiz Ct, Oakland, MD 21550
      /71

      Est $697,426 Not Listed For Sale

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

      10 Ortiz Ct, Oakland, MD 21550

      10 Ortiz Ct, 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
  • 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 $399,329

    Last Listing Agent Julie Mead The KW Collective

    343 Maple Del Ln, Oakland, MD 21550
    • 139 Hunters Dr, Oakland, MD 21550
      139 Hunters Dr, Oakland, MD 21550
      139 Hunters Dr, Oakland, MD 21550
      /41

      Est $369,972 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
  • 104 Pine Top Trail, Oakland, MD 21550
    104 Pine Top Trail, Oakland, MD 21550
    104 Pine Top Trail, Oakland, MD 21550
    /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
  • 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 $1,156,066

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

    324 Penn Cove Rd, 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 $2,316,559 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
  • 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
  • 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
    • 204 Farm View Ln, Oakland, MD 21550
      204 Farm View Ln, Oakland, MD 21550
      204 Farm View Ln, Oakland, MD 21550
      /95

      Est $548,009 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
  • 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
  • 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

    Last Listing Agent Larry Smith Railey Realty, Inc.

    783 Mountainview Dr, Oakland, MD 21550
    • 144 Middleton Rd, Oakland, MD 21550
      144 Middleton Rd, Oakland, MD 21550
      144 Middleton Rd, Oakland, MD 21550
      /73

      Est $1,004,119 Not Listed For Sale

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

      144 Middleton Rd, Oakland, MD 21550

      144 Middleton Rd, Oakland, MD 21550
  • 611 E Oak St, Oakland, MD 21550
    611 E Oak St, Oakland, MD 21550
    611 E Oak St, Oakland, MD 21550
    /14

    $295,000

    • 5 Beds
    • 3 Baths
    • 1,800 Sq Ft

    611 E Oak St, Oakland, MD 21550

    Investors, this is an income producing, three unit building with three separate apartments, just a few minutes walk to downtown Oakland. Main level and upper level are two bedroom units and basement unit is a one bedroom. All units have current leases in place. One renter has been renting for 12 years, one for 10 years, and the third for eight years. The entire building is in excellent condition.

    Justin Liller Railey Realty, Inc.

    611 E Oak St, 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

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

    20160 Garrett Hwy Unit G509, 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 $1,533,652 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
  • 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
  • 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
    • 2524 Stockslager Rd, Oakland, MD 21550
      2524 Stockslager Rd, Oakland, MD 21550
      2524 Stockslager Rd, Oakland, MD 21550
      /132

      Est $3,656,455 Not Listed For Sale

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

      2524 Stockslager Rd, Oakland, MD 21550

      2524 Stockslager 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
    /25

    $329,000

    • 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
  • Lot 5 Bobcat Hill Ln, Oakland, MD 21550
    Lot 5 Bobcat Hill Ln, Oakland, MD 21550
    Lot 5 Bobcat Hill Ln, Oakland, MD 21550
    /7

    $90,000 Sold Feb 07, 2025

    Lot 5 Bobcat Hill Ln, Oakland, MD 21550

    • Land
    • 2.36 Acres
    • $38,136 per Acre

    Last Sold Summary

    • 43 Days On Market

    Last Listing Agent Kim Palmer Marquee Properties, Inc.

    Lot 5 Bobcat Hill Ln, 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 $581,650 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
  • 333 Sloan Tract Rd, Oakland, MD 21550
    333 Sloan Tract Rd, Oakland, MD 21550
    333 Sloan Tract Rd, Oakland, MD 21550
    /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 Vacations & Sales

    333 Sloan Tract Rd, Oakland, MD 21550
  • 465 King Wildesen Rd, Oakland, MD 21550
    465 King Wildesen Rd, Oakland, MD 21550
    465 King Wildesen Rd, Oakland, MD 21550
    /40

    $335,000 Sold May 23, 2025

    465 King Wildesen Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1988

    Last Sold Summary

    • 22% Below List Price
    • $436/SF
    • 123 Days On Market

    Current Estimated Value $332,490

    Last Listing Agent ADAM MURRAY BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    465 King Wildesen Rd, Oakland, MD 21550
    • 471 Clifton Dr, Oakland, MD 21550
      471 Clifton Dr, Oakland, MD 21550
      471 Clifton Dr, Oakland, MD 21550
      /21

      Est $550,188 Not Listed For Sale

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

      471 Clifton Dr, Oakland, MD 21550

      471 Clifton Dr, Oakland, MD 21550
  • 0 Mayhew Inn Rd Unit MDGA2009662, Oakland, MD 21550
    0 Mayhew Inn Rd Unit MDGA2009662, Oakland, MD 21550
    0 Mayhew Inn Rd Unit MDGA2009662, Oakland, MD 21550
    /31

    $120,000

    • Land
    • 12.95 Acres
    • $9,266 per Acre

    0 Mayhew Inn Rd Unit MDGA2009662, Oakland, MD 21550

    Almost 13 acres of beautiful land in the Deep Creek Lake area. 2 lots featuring beautiful mature trees, a clearing to build on, and just minutes to all of Deep Creek Lake's recreation, shopping, restaurants, and amenities.

    Justin Liller Railey Realty, Inc.

    0 Mayhew Inn Rd Unit MDGA2009662, Oakland, MD 21550
  • 9 & 10 Grouse Run Rd, Oakland, MD 21550
    9 & 10 Grouse Run Rd, Oakland, MD 21550
    9 & 10 Grouse Run Rd, Oakland, MD 21550
    /20

    $17,000 Sold Oct 29, 2025

    9 & 10 Grouse Run Rd, Oakland, MD 21550

    • Land
    • 0.96 Acre
    • $17,708 per Acre

    Last Sold Summary

    • 50 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    9 & 10 Grouse Run Rd, Oakland, MD 21550
    • 43 Robinwood Dr, Oakland, MD 21550
      43 Robinwood Dr, Oakland, MD 21550
      43 Robinwood Dr, Oakland, MD 21550
      /81

      Est $797,229 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
  • 0 E Water St, Oakland, MD 21550
    0 E Water St, Oakland, MD 21550
    /2

    $8,000 Sold Aug 29, 2025

    0 E Water St, Oakland, MD 21550

    • Land
    • 0.33 Acre
    • $24,242 per Acre

    Last Sold Summary

    • 2 Days On Market

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

    0 E Water St, Oakland, MD 21550
    • 36 Preston Ln, Oakland, MD 21550
      36 Preston Ln, Oakland, MD 21550
      36 Preston Ln, Oakland, MD 21550
      /16

      Est $66,345 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 964 Sq Ft

      36 Preston Ln, Oakland, MD 21550

      36 Preston Ln, 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
  • 204 E St, Oakland, MD 21550
    204 E St, Oakland, MD 21550
    204 E St, Oakland, MD 21550
    /37

    $120,000 Sold Dec 04, 2025

    204 E St, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 2,084 Sq Ft
    • Built 1975

    Last Sold Summary

    • $58/SF
    • 1 Day On Market

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    204 E St, 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 $746,238 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

Showing Results 321 - 360, Page 9 of 18

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