10,771

Oakland, MD Homes

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  • /82

    $760,000

    $105K PRICE DROP
    • 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, two

    Melissa Long Railey Realty, Inc.

    1909 Pysell Crosscut Rd, Oakland, MD 21550
  • /6

    $30,000

    Sold Oct 23, 2025

    28 Wild Turkey Ln, Oakland, MD 21550

    • Land
    • 1 Acre
    • $30,000 per Acre

    Last Sold Summary

    • 14 Days On Market

    Last Listing Agent Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    28 Wild Turkey Ln, Oakland, MD 21550
    • /88

      Est $450,573

      Not Listed For Sale

      189 Whistle Pig Way, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,777 Sq Ft
      • Built 1998
      189 Whistle Pig Way, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • /60

    $174,900

    • 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
  • /62

    $349,900

    Sold May 08, 2026

    16 Lemley Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 1,104 Sq Ft
    • Built 1974

    Last Sold Summary

    • $317/SF
    • 128 Days On Market

    Current Estimated Value $373,339

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    16 Lemley Dr, Oakland, MD 21550
    • /80

      Est $1,463,854

      Not Listed For Sale

      2236 Paradise Point Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,004 Sq Ft
      • Built 1956
      2236 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • /9

    $3,500

    • Land
    • 20,908 Sq Ft
    • $7,292 per Acre

    LOT 2 Beaver Run Rd, Oakland, MD 21550

    Tucked away in the stunning mountains of Western Maryland, this unbuildable lot provides a serene escape into nature, offering breathtaking views throughout the community, as well as an abundance wildlife. Located in the Youghiogheny Mountain Resort, this membership-only lot grants exclusive access to over 50 miles of private roads and trails, ideal for ATV and side-by-side adventures. Resort

    Elizabeth Broadwater Taylor-Made Deep Creek Real Estate, LLC

    LOT 2 Beaver Run Rd, Oakland, MD 21550
  • /34

    $275,000

    Sold Jan 02, 2026

    34 Laurel Brook Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1992

    Last Sold Summary

    • 13 Days On Market

    Current Estimated Value $309,765

    Last Listing Agent Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    34 Laurel Brook Dr, Oakland, MD 21550
    • /27

      Not Listed For Sale

      128 Shaffer Ln, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,040 Sq Ft
      • Built 2001
      128 Shaffer Ln, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • /77

    $899,000

    $31K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 2,464 Sq Ft

    62 Whispering Pines Ln, Oakland, MD 21550

    Tucked away on just over 7 acres of serene, wooded privacy, this stunning custom Yellowstone log home offers the perfect blend of rustic charm and modern comfort—just minutes from Swallow Falls State Park and only 10 minutes to Deep Creek Lake and Wisp Resort. The inviting open main level is designed for effortless entertaining, highlighted by a warm gas fireplace in the family room, a spacious

    Justin Liller Railey Realty, Inc.

    62 Whispering Pines Ln, Oakland, MD 21550
  • /48

    $205,000

    Sold Mar 20, 2026

    565 Glendale Rd Unit 312, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft
    • Built 2006

    Last Sold Summary

    • 10% Below List Price
    • $261/SF
    • 6 Days On Market

    Current Estimated Value $253,284

    Last Listing Agent Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 312, Oakland, MD 21550
    • /49

      Est $1,190,331

      Not Listed For Sale

      215 Lower Penn Point Dr, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 2,580 Sq Ft
      • Built 2001
      215 Lower Penn Point Dr, Oakland, MD 21550

      Last Sold Summary

      • 51 Days On Market

  • /52

    $749,900

    • 5 Beds
    • 4 Baths
    • 2,364 Sq Ft

    25 Silver Tree Ln, Oakland, MD 21550

    Beautiful lake access retreat located in the Silver Tree Landings community with an available home warranty. This recently updated contemporary home feels warm and inviting from the moment you walk in (upgrade list available). Offering hardwood flooring, granite countertops, two stone propane fireplaces and cathedral ceilings. The abundance of windows allows the natural light to brighten any

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

    25 Silver Tree Ln, Oakland, MD 21550
  • /47

    $285,000

    Sold Oct 31, 2025

    1764 Underwood Rd, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,304 Sq Ft
    • Built 1968

    Last Sold Summary

    • $124/SF
    • 175 Days On Market

    Current Estimated Value $275,248

    Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    1764 Underwood Rd, Oakland, MD 21550
    • /74

      Est $170,135

      Not Listed For Sale

      400 E St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,880 Sq Ft
      • Built 1900
      400 E St, Oakland, MD 21550

      Last Sold Summary

      • 98 Days On Market

  • /28

    $82,500

    • Land
    • 2.53 Acres
    • $32,609 per Acre

    8760 Oakland Sang Run Rd, Oakland, MD 21550

    Attention outdoor enthusiasts! This 2.53 acre lot just across the road from state-owned land down to the world-famous Youghiogheny River is a whitewater lover or fisherman's dream. Complete with a gravel driveway up to a flat gravel pad and electric meter ready to go, perfect for a camper or a forever home. Perc-approved for 3 bedrooms and less than half a mile from easy public Yough access.

    Elizabeth Ware Railey Realty, Inc.

    8760 Oakland Sang Run Rd, Oakland, MD 21550
  • /52

    $920,000

    Sold Jun 15, 2026

    1295 Mountainview Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 3,550 Sq Ft
    • Built 2003

    Last Sold Summary

    • $259/SF
    • 3 Days On Market

    Current Estimated Value $935,537

    Last Listing Agent Debbie Roberts Long & Foster Real Estate, Inc.

    1295 Mountainview Dr, Oakland, MD 21550
    • /32

      Est $312,755

      Not Listed For Sale

      67 Fireside Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1998
      67 Fireside Rd, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • /37

    $219,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    407 Seneca Ave, Oakland, MD 21550

    Move right into this charming ranch style home offering comfortable one-level living! Recent improvements include a brand-new roof and fresh carpet throughout, giving the home a clean, updated feel. Offering three bedrooms and a wood burning fireplace which just adds to the warmth and coziness. The level yard provides great space for relaxing and entertaining family and friends. The location is

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

    407 Seneca Ave, Oakland, MD 21550
  • /56

    $697,000

    Sold Dec 19, 2025

    969 Hoyes Run Rd, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,614 Sq Ft
    • Built 1998

    Last Sold Summary

    • $193/SF
    • 180 Days On Market

    Current Estimated Value $709,977

    Last Listing Agent Roberta McNamara RE/MAX Results

    969 Hoyes Run Rd, Oakland, MD 21550
    • /42

      Est $684,913

      Not Listed For Sale

      26 Arrowhead Ln, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,000 Sq Ft
      • Built 1988
      26 Arrowhead Ln, Oakland, MD 21550

      Last Sold Summary

      • 389 Days On Market

  • /22

    $294,999

    • 2 Beds
    • 1 Bath
    • 2,344 Sq Ft

    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550

    Experience the best of lakeview living in this great condo at Deep Creek Lake. Offering two bedrooms, a fireplace and a lower-level family room for your enjoyment. Wake up to peaceful water views and enjoy ample space for everyday comfort and entertaining. The location is another plus, within walking distance to coffee shop, dining, and shopping. A perfect blend of size, scenery, and value!

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

    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550
  • /29

    $225,000

    Sold Nov 17, 2025

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 520 Sq Ft
    • Built 1990

    Last Sold Summary

    • $433/SF
    • 26 Days On Market

    Current Estimated Value $225,025

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    • /26

      Est $159,683

      Not Listed For Sale

      419 Seneca Ave, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,184 Sq Ft
      • Built 1920
      419 Seneca Ave, Oakland, MD 21550

      Last Sold Summary

      • 46 Days On Market

  • /46

    $285,500

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft

    1737 King Wildesen Rd, Oakland, MD 21550

    Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-sided home offers the perfect blend of rustic charm and modern comfort—all just 10 minutes from downtown Oakland. This well-maintained home features 3 spacious bedrooms and 2 full bathrooms, including a main floor master suite for added convenience. Inside, you’ll find brand-new luxury vinyl plank (LVP)

    Justin Liller Railey Realty, Inc.

    1737 King Wildesen Rd, Oakland, MD 21550
  • /39

    $195,000

    Sold Nov 12, 2025

    501 Christophers Way, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • Built 1994

    Last Sold Summary

    • $121/SF
    • 138 Days On Market

    Last Listing Agent Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    501 Christophers Way, Oakland, MD 21550
    • /62

      Est $1,307,043

      Not Listed For Sale

      581 Skippers Point Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,100 Sq Ft
      • Built 1977
      581 Skippers Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

  • /19

    $40,000

    $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 782 Sq Ft

    820 N 4th St, Oakland, MD 21550

    Step into potential with this 2 bed, 1 bath home being sold AS IS. Located in a convenient community with town water & sewer, this property offers a blank canvas for the savvy buyer or investor ready to bring a vision to life. The house has been gutted and is ready for the new owner to start the renovation, providing a clear interior and a fresh slate to customize the layout, finishes, and

    Duane Stein II The KW Collective

    820 N 4th St, Oakland, MD 21550
  • /41

    $218,000

    Sold Dec 01, 2025

    1136 Black Oak Dr, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1971

    Last Sold Summary

    • $206/SF
    • 7 Days On Market

    Current Estimated Value $221,447

    Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    1136 Black Oak Dr, Oakland, MD 21550
    • /87

      Est $310,188

      Not Listed For Sale

      233 N 2nd St, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 2,218 Sq Ft
      • Built 1914
      233 N 2nd St, Oakland, MD 21550

      Last Sold Summary

      • 432 Days On Market

  • /49

    $379,500

    • 1 Bed
    • 1 Bath
    • 636 Sq Ft

    20160 Garrett Hwy Unit C307, Oakland, MD 21550

    Experience the best of Deep Creek Lake from this beautifully situated 2-story, 1-bedroom, 1-bath condominium at Will O' The Wisp. Offering 636 square feet of comfortable living space and spectacular lake views, this waterfront retreat is the perfect personal getaway, year-round residence, or vacation rental investment. Enjoy your morning coffee while taking in panoramic views of the water, then

    Justin Liller Railey Realty, Inc.

    20160 Garrett Hwy Unit C307, Oakland, MD 21550
  • /18

    $200,000

    Sold Sep 15, 2025

    2571 Shady Dell Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • Built 1985

    Last Sold Summary

    • $119/SF
    • 62 Days On Market

    Current Estimated Value $265,030

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    2571 Shady Dell Rd, Oakland, MD 21550
    • /76

      Est $593,694

      Not Listed For Sale

      1094 Eagle Rock Rd, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 3,780 Sq Ft
      • Built 2008
      1094 Eagle Rock Rd, Oakland, MD 21550

      Last Sold Summary

      • 109 Days On Market

  • /56

    $745,000

    • 5 Beds
    • 3 Baths
    • 2,640 Sq Ft

    638 Glendale Rd, Oakland, MD 21550

    Spacious five-bedroom lakeview home offering the perfect blend of relaxation and warmth from the moment you enter. This established rental property “Terp’s Hideaway” features an open and inviting floorplan, five bedrooms, two family rooms, and three levels of living space, making it an ideal layout for hosting family and friends. Step outside onto the large deck to take in beautiful views or

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

    638 Glendale Rd, Oakland, MD 21550
  • /93

    $1,445,000

    Sold Nov 14, 2025

    128 Big Bass Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,305 Sq Ft
    • Built 2023

    Last Sold Summary

    • $336/SF
    • 13 Days On Market

    Current Estimated Value $1,400,033

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    128 Big Bass Dr, Oakland, MD 21550
    • /34

      Est $202,713

      Not Listed For Sale

      700 N St, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,724 Sq Ft
      • Built 1973
      700 N St, Oakland, MD 21550

      Last Sold Summary

      • 57 Days On Market

  • /61

    $335,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 2,052 Sq Ft

    105 Jasper Riley Rd, Oakland, MD 21550

    Park like, setting on 1.7 acres in Pleasant Valley, 4 Br, 2BA ranch home with full basement. Close to town yet, peaceful and secluded. Home features 4 Bedrooms, primary has 2 walk-in closets & large primary bath with walk-in shower. Front living & dining areas, with main entrance from the covered front porch. Open Kitchen, breakfast nook and den area with wood burning fireplace. Opens to covered

    Julie Mead The KW Collective

    105 Jasper Riley Rd, Oakland, MD 21550
  • /56

    $320,000

    Sold Nov 05, 2025

    531 S 3rd St, Oakland, MD 21550

    • 5 Beds
    • 2.5 Baths
    • 2,477 Sq Ft
    • Built 1920

    Last Sold Summary

    • $129/SF
    • 118 Days On Market

    Current Estimated Value $316,080

    Last Listing Agent Jennifer Jackson Charis Realty Group

    531 S 3rd St, Oakland, MD 21550
    • /46

      Est $318,882

      Not Listed For Sale

      134 Skippers Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,497 Sq Ft
      • Built 1990
      134 Skippers Ln, Oakland, MD 21550

      Last Sold Summary

      • 59 Days On Market

  • /37

    $279,000

    • 3 Beds
    • 1.5 Baths
    • 1,148 Sq Ft

    277 Cheeks Ln, Oakland, MD 21550

    Tucked away on a private lane and surrounded by the beauty of the woods, this charming 3-bedroom, 1 full bath and 1 half bath log home offers the perfect mountain retreat on 2 peaceful acres in Garrett County. Ideally located just minutes from Swallow Falls State Park, Muddy Creek Falls, and the Youghiogheny River, this cozy cabin is a dream destination for outdoor enthusiasts seeking hiking,

    Mike Kennedy Railey Realty, Inc.

    277 Cheeks Ln, Oakland, MD 21550

Showing Results 481 - 520, Page 13 of 18

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