10,739

Oakland, MD Homes

Section Image
  • /64

    $275,900

    • 4 Beds
    • 2 Baths
    • 1,928 Sq Ft

    449 S 3rd St, Oakland, MD 21550

    Welcome to this beautifully updated 1901 home in the heart of downtown Oakland, where historic character meets modern convenience. Situated on a charming lot with mature landscaping and blooming trees, this home offers timeless curb appeal with a welcoming covered front porch perfect for relaxing and enjoying the neighborhood. Inside, you’ll find modern updates throughout while preserving classic

    Justin Liller Railey Realty, Inc.

    449 S 3rd St, 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 $350,904

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

    465 King Wildesen Rd, Oakland, MD 21550
    • /6

      Est $663,791 Not Listed For Sale

      20488 Garrett Hwy, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 840 Sq Ft
      • Built 1946
      20488 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 3% Above List Price
      • $766/SF
      • 125 Days On Market

      Last Sold Price $643,500

      Last Listing Agent Michael Cumerlato Jason Mitchell Group

  • /43

    $325,000

    • 2 Beds
    • 2 Baths
    • 2,015 Sq Ft

    3749 Maryland Hwy, Oakland, MD 21550

    Set on a beautiful lot in Deep Creek, Maryland, this stunning property offers the perfect blend of privacy, relaxation, and investment potential. Currently enjoyed as a second home, the residence has also been successfully utilized as a partial Airbnb, generating approximately $28,000 in rental income last year. The home has been thoughtfully updated, creating a warm and inviting atmosphere with

    Jovan Vidulovic Keller Williams Realty

    3749 Maryland Hwy, 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
    • /85

      Est $1,838,797 Not Listed For Sale

      739 Glendale Rd, Oakland, MD 21550

      • 6 Beds
      • 6.5 Baths
      • 4,160 Sq Ft
      • Built 2003
      739 Glendale Rd, Oakland, MD 21550

      Last Sold Summary

      • 13% Above List Price
      • $393/SF
      • 90 Days On Market

      Last Sold Price $1,634,000

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

  • /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
  • /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
    • /73

      Est $244,035 Not Listed For Sale

      723 E Alder St, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft
      • Built 1950
      723 E Alder St, Oakland, MD 21550

      Last Sold Summary

      • 14% Above List Price
      • $122/SF

      Last Sold Price $215,000

      Last Listing Agent Jesse Shimrock Railey Realty, Inc.

  • /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
  • /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

    Current Estimated Value $124,269

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    204 E St, Oakland, MD 21550
    • /130

      Est $1,139,013 Not Listed For Sale

      943 S Blakeslee Rd, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 3,426 Sq Ft
      • Built 1990
      943 S Blakeslee Rd, Oakland, MD 21550

      Last Sold Summary

      • 14% Above List Price
      • $292/SF
      • 4 Days On Market

      Last Sold Price $999,900

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /59

    $220,000

    • 2 Beds
    • 1 Bath
    • 1,064 Sq Ft

    313 W Liberty St, Oakland, MD 21550

    Charming and meticulously maintained 1947 brick ranch located at the edge of Oakland town limits on a beautiful 1⁄4-acre lot. This 2-bedroom, 1-bath home features spacious rooms, natural gas heat, public utilities, and a full unfinished basement offering great storage or future potential. Ownership includes a 1⁄2 interest in a shared 2-car garage. Conveniently situated near schools, the hospital,

    Justin Liller Railey Realty, Inc.

    313 W Liberty St, Oakland, MD 21550
  • /47

    $270,000 Sold Jun 20, 2025

    403 O St, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,240 Sq Ft
    • Built 1976

    Last Sold Summary

    • $121/SF
    • 329 Days On Market

    Current Estimated Value $275,521

    Last Listing Agent ANGELA BOSLEY Taylor Made Deep Creek Real Estate

    403 O St, Oakland, MD 21550
    • /88

      Est $395,927 Not Listed For Sale

      223 N 2nd St, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 3,120 Sq Ft
      • Built 1920
      223 N 2nd St, Oakland, MD 21550

      Last Sold Summary

      • 2% Above List Price
      • $125/SF
      • 109 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Sean Sober Taylor Made Deep Creek Real Estate

  • /8

    $25,000

    • Land
    • 3 Acres
    • $8,333 per Acre

    0 Hoye St, Oakland, MD 21550

    Make an offer, buy it now +/- 2.96 Acre lot of land in Garrett County. Close to the West Virginias Border. Easy access to major traffic artery Seneca Trail Highway. Parcel is vacant. Deposit is $5,000

    Adam Shpritz

    0 Hoye St, Oakland, MD 21550
  • /80

    $696,000 Sold Apr 02, 2025

    1489 Mountainview Dr, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,066 Sq Ft
    • Built 2001

    Last Sold Summary

    • $227/SF
    • 170 Days On Market

    Current Estimated Value $735,079

    Last Listing Agent Larry Smith Railey Realty, Inc.

    1489 Mountainview Dr, Oakland, MD 21550
    • /54

      Est $2,486,848 Not Listed For Sale

      375 Glendale Rd, Oakland, MD 21550

      • 8 Beds
      • 6.5 Baths
      • 5,638 Sq Ft
      • Built 2001
      375 Glendale Rd, Oakland, MD 21550

      Last Sold Summary

      • 8% Above List Price
      • $408/SF
      • 134 Days On Market

      Last Sold Price $2,300,000

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • /62

    $1,750,000

    • 5 Beds
    • 4 Baths
    • 3,456 Sq Ft

    1544 Stockslager Rd, Oakland, MD 21550

    Enjoy lakefront living at its finest in this beautifully remodeled home with a private dock. Thoughtfully updated with modern finishes including a kitchen remodel, new windows and doors, new upper balcony, new flooring throughout, and recently added mini splits on the lower level. This property offers stunning water views, an open-concept layout, five bedrooms (three of which are en suites), and

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    1544 Stockslager Rd, Oakland, MD 21550
  • /47

    $260,000 Sold Feb 27, 2026

    20160 Garrett Hwy Unit H708, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft
    • Built 1972

    Last Sold Summary

    • $473/SF
    • 234 Days On Market

    Current Estimated Value $280,937

    Last Listing Agent Charlotte Savoy The KW Collective

    20160 Garrett Hwy Unit H708, Oakland, MD 21550
    • /18

      Est $250,266 Not Listed For Sale

      9 Laurel Brook Dr, Oakland, MD 21550

      • 2 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1989
      9 Laurel Brook Dr, Oakland, MD 21550

      Last Sold Summary

      • 12% Above List Price
      • $185/SF
      • 13 Days On Market

      Last Sold Price $222,500

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /19

    $289,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    226 N Hammond St, Oakland, MD 21550

    NEW CONSTRUCTION from Lyv Homes! This 2BR/2BA, 1000sf cottage is located in the historic 2nd Street area of Oakland and features modern design with elite finishes. Key features include Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets and drawers, quartz counters and range backsplash, shiplap backsplash accents, stainless steel Frigidaire

    Jay Ferguson Taylor Made Deep Creek Real Estate

    226 N Hammond St, Oakland, MD 21550
  • /107

    $1,350,000 Sold Sep 19, 2025

    421 Penn Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 4,284 Sq Ft
    • Built 1986

    Last Sold Summary

    • $315/SF
    • 54 Days On Market

    Current Estimated Value $1,467,349

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    421 Penn Cove Rd, Oakland, MD 21550
    • /55

      Est $787,540 Not Listed For Sale

      1557 Mountainview Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,590 Sq Ft
      • Built 1992
      1557 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 6% Above List Price
      • $286/SF
      • 163 Days On Market

      Last Sold Price $740,000

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

  • /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
  • /67

    $855,000 Sold May 12, 2025

    249 Marys Ln, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,874 Sq Ft
    • Built 2017

    Last Sold Summary

    • $297/SF
    • 7 Days On Market

    Current Estimated Value $927,254

    Last Listing Agent Jon Bell Railey Realty, Inc.

    249 Marys Ln, Oakland, MD 21550
    • /91

      Est $313,220 Not Listed For Sale

      106 H St, Oakland, MD 21550

      • 7 Beds
      • 3 Baths
      • 2,934 Sq Ft
      • Built 1900
      106 H St, Oakland, MD 21550

      Last Sold Summary

      • 11% Above List Price
      • $96/SF
      • 1,050 Days On Market

      Last Sold Price $281,800

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

  • /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
  • /61

    $820,000 Sold Sep 02, 2025

    939 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1990

    Last Sold Summary

    • 18 Days On Market

    Current Estimated Value $845,117

    Last Listing Agent Sean Sober Taylor Made Deep Creek Real Estate

    939 Glendale Rd, Oakland, MD 21550
    • /63

      Est $2,721,542 Not Listed For Sale

      25 Old Chestnut Dr, Oakland, MD 21550

      • 9 Beds
      • 9 Baths
      • 5,362 Sq Ft
      • Built 2003
      25 Old Chestnut Dr, Oakland, MD 21550

      Last Sold Summary

      • 14% Above List Price
      • $444/SF
      • 270 Days On Market

      Last Sold Price $2,380,000

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

  • /9

    $3,500

    • Land
    • 0.48 Acre
    • $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 and abundant 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 amenities include a community clubhouse,

    Elizabeth Broadwater Taylor Made Deep Creek Real Estate

    LOT 2 Beaver Run Rd, Oakland, MD 21550
  • /100

    $1,860,000 Sold Oct 06, 2025

    237 Glendale Rd, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 3,735 Sq Ft
    • Built 2002

    Last Sold Summary

    • $498/SF
    • 88 Days On Market

    Current Estimated Value $1,915,411

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    237 Glendale Rd, Oakland, MD 21550
    • /65

      Est $256,285 Not Listed For Sale

      6663 Gorman Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,982 Sq Ft
      • Built 1978
      6663 Gorman Rd, Oakland, MD 21550

      Last Sold Summary

      • 14% Above List Price
      • $114/SF
      • 113 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /77

    $930,000

    • 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
  • /56

    $157,000 Sold Aug 29, 2025

    416 Shenandoah Ave, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • Built 1940

    Last Sold Summary

    • $161/SF
    • 4 Days On Market

    Current Estimated Value $159,542

    Last Listing Agent Rich Orr Railey Realty, Inc.

    416 Shenandoah Ave, Oakland, MD 21550
    • /83

      Est $359,554 Not Listed For Sale

      10 Sunset Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,167 Sq Ft
      • Built 1979
      10 Sunset Dr, Oakland, MD 21550

      Last Sold Summary

      • 19% Above List Price
      • $140/SF
      • 53 Days On Market

      Last Sold Price $302,500

      Last Listing Agent Thomas Long Railey Realty, Inc.

  • /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

    25 Silver Tree Ln, Oakland, MD 21550
  • /51

    $425,000 Sold Oct 22, 2025

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,202 Sq Ft
    • Built 2012

    Last Sold Summary

    • $193/SF
    • 130 Days On Market

    Current Estimated Value $435,126

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    • /32

      Est $231,400 Not Listed For Sale

      601 E Oak St, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 1,744 Sq Ft
      • Built 1922
      601 E Oak St, Oakland, MD 21550

      Last Sold Summary

      • 9% Above List Price
      • $122/SF
      • 3 Days On Market

      Last Sold Price $212,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /34

    $239,700

    • 3 Beds
    • 3 Baths
    • 1,104 Sq Ft

    53 Bird Ave, Oakland, MD 21550

    Opportunity and a peaceful country setting on 1.55 acres in Deer Park. This 3BR, 2BA ranch offers 1,872 sq ft with solid bones and room to make it your own. The spacious kitchen with hickory cabinets, gas stove, and propane fireplace creates a warm gathering space at the heart of the home. Outside, several outbuildings—including a large shop and secondary wood shop with heat and electric, a

    Rachel Bruch Railey Realty, Inc.

    53 Bird Ave, Oakland, MD 21550

Showing Results 361 - 400, Page 10 of 18

How to Buy a Home How to Finance a Home How to Sell a Home