10,549

Oakland, MD Homes

Section Image
    • /6

      Not Listed For Sale

      223 Old Crellin Rd, Oakland, MD 21550

      • 1 Bed
      • 1 Bath
      • 980 Sq Ft
      • Built 1986
      223 Old Crellin Rd, Oakland, MD 21550

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Garrett Shingler Real Broker, LLC

  • /62

    $669,999

    $69K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,420 Sq Ft

    620 Crosby Dr, Oakland, MD 21550

    Price improvement! This stunning, recently built 4+ bedroom, 3.5 bath home in Country Club Acres offers modern design, thoughtful upgrades, and unmatched privacy on 3.43 wooded acres perched at the top of the mountain overlooking Oakland Golf Course and multiple ponds. The bright, open-concept layout is filled with natural light and features commercial-grade LVP flooring throughout, complemented

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    620 Crosby Dr, Oakland, MD 21550
  • /47

    $202,039

    Sold Jun 08, 2026

    43 Sloan Tract Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,743 Sq Ft
    • Built 1930

    Last Sold Summary

    • 38% Below List Price
    • $116/SF
    • 34 Days On Market

    Current Estimated Value $292,000

    Last Listing Agent Justin Liller Railey Realty, Inc.

    43 Sloan Tract Rd, Oakland, MD 21550
    • /21

      Est $272,218

      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

      • 159 Days On Market

      Last Listing Agent Linda Deremer Appalachian Realty

  • /53

    $1,199,000

    • 4 Beds
    • 3 Baths
    • 1,844 Sq Ft

    20698 Garrett Hwy, Oakland, MD 21550

    Beautiful lakefront home offering 89' of lakefront and a private dock. This home has been remodeled and is very warm and inviting from the moment you enter. Boasting a great island featuring granite countertops, and plenty of seating for family and friends. The lakefront views are unobstructed year round, and can be enjoyed from most any room. The outside space is just as pleasing with a

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

    20698 Garrett Hwy, Oakland, MD 21550
  • /74

    $664,500

    Sold Oct 17, 2025

    94 Meadow Ct, Oakland, MD 21550

    • 3 Beds
    • 4 Baths
    • 2,460 Sq Ft
    • Built 1999

    Last Sold Summary

    • $270/SF
    • 54 Days On Market

    Current Estimated Value $701,720

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

    94 Meadow Ct, Oakland, MD 21550
    • /4

      Est $3,098,576

      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

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /3

    $115,000

    Pending
    • Land
    • 1 Acre
    • $115,000 per Acre

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550

    Centrally located 1-acre lake access homesite with a dock slip! This property has endless possibilities to build, and depending on where you decide to position your new home, there could be potential for lake views. Offering public sewer and no HOA fees. The only decision left to be made is what style home you will build. Just minutes to the DCL State Park, several restaurants, convenience store,

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

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550
  • /56

    $295,500

    Sold Aug 04, 2026

    17921 Garrett Hwy, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 1,563 Sq Ft
    • Built 1952

    Last Sold Summary

    • 18% Below List Price
    • $189/SF
    • 66 Days On Market

    Current Estimated Value $319,697

    Last Listing Agent Michelle Clark Taylor-Made Deep Creek Real Estate, LLC

    17921 Garrett Hwy, Oakland, MD 21550
    • /72

      Est $606,819

      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

      • 1 Day On Market

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /46

    $150,000

    • Land
    • 21.46 Acres
    • $6,990 per Acre

    0 Sanders Ln Unit MDGA2011678, Oakland, MD 21550

    Endless Possibilities on 21.46 Acres! A rare private setting featuring gently rolling, pastoral land along scenic Sanders Lane-just 4 miles from Oakland. Enjoy open fields, and woods on a private and a peaceful setting in a desirable area. Enjoy wide-open skies, room to roam, and the serenity of nature—all within minutes of town conveniences, and all the activities Garrett County has to offer!

    Susan Bell Railey Realty, Inc.

    0 Sanders Ln Unit MDGA2011678, Oakland, MD 21550
  • /21

    $115,000

    Sold Nov 03, 2025

    607 K St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • Built 1920

    Last Sold Summary

    • $86/SF
    • 213 Days On Market

    Current Estimated Value $117,927

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    607 K St, Oakland, MD 21550
    • /61

      Est $230,528

      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

      • 8 Days On Market

      Last Listing Agent Sandy Bello Taylor-Made Deep Creek Real Estate, LLC

  • /41

    $379,999

    New Construction $70K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    654 N Bradley Ln, Oakland, MD 21550

    NEW CONSTRUCTION from Lyv Homes! 3BR/2BA, 1464sf contemporary style home fronting on the 13th hole of the Oakland golf course. This property combines scenic views with modern design and outdoor living. Key features include multiple wood-burning fireplaces, Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets and drawers, quartz countertops,

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    654 N Bradley Ln, Oakland, MD 21550
  • /37

    $255,000

    Sold Apr 23, 2026

    127 Jeffrey Ln Unit 18C, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 875 Sq Ft
    • Built 1997

    Last Sold Summary

    • 7% Below List Price
    • $291/SF
    • 34 Days On Market

    Current Estimated Value $271,638

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

    127 Jeffrey Ln Unit 18C, Oakland, MD 21550
    • /83

      Est $1,567,206

      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

      • 20 Days On Market

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • /49

    $575,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,383 Sq Ft

    135 Rock Ridge Ln Unit 13, Oakland, MD 21550

    Experience a rare blend of comfort, style, and location in this beautiful 4-bedroom, 3-bath Craftsman-style home in Silver Ridge. An established vacation rental, Wine Down features an open floorplan with hardwood floors, two fireplaces, and warm, inviting décor throughout. The main level is designed for easy living and entertaining, offering a spacious great room with a fireplace, a kitchen ideal

    Mike Kennedy Railey Realty, Inc.

    135 Rock Ridge Ln Unit 13, Oakland, MD 21550
  • /65

    $150,000

    Sold Mar 26, 2026

    506 Roanoke Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1940

    Last Sold Summary

    • 16% Below List Price
    • $111/SF
    • 4 Days On Market

    Current Estimated Value $162,485

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    506 Roanoke Ave, Oakland, MD 21550
    • /51

      Est $344,602

      Not Listed For Sale

      18361 Garrett Hwy, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,112 Sq Ft
      • Built 1977
      18361 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 131 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /57

    $219,000

    Pending
    • 1 Bed
    • 1.5 Baths
    • 912 Sq Ft

    141 Montana Ln, Oakland, MD 21550

    Nestled on nearly 3 acres across two parcels, this chalet-style home offers a rare opportunity to create your retreat just minutes from the lake. Renovate the existing structure, or start fresh and build the lake-area retreat or cabin you’ve always imagined. The level, wooded setting provides privacy, peace, and plenty of room to expand, garden, or simply enjoy nature. With well and septic

    Larry Smith Railey Realty, Inc.

    141 Montana Ln, Oakland, MD 21550
  • /39

    $262,500

    Sold Feb 05, 2026

    14 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • Built 1989

    Last Sold Summary

    • 3% Below List Price
    • $199/SF
    • 2 Days On Market

    Current Estimated Value $270,550

    Last Listing Agent Larry Smith Railey Realty, Inc.

    14 Laurel Brook Dr, Oakland, MD 21550
    • /58

      Est $447,399

      Not Listed For Sale

      2734 Mayhew Inn Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1974
      2734 Mayhew Inn Rd, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

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

  • /41

    $375,000

    • 2 Beds
    • 2 Baths
    • 1,404 Sq Ft

    18948 Garrett Hwy, Oakland, MD 21550

    Enjoy all the seasons in this beautiful Cape Cod home nestled on a 1-acre private wooded lot close to Oakland and all the attractions Deep Creek Lake has to offer. Whether you are seeking a year-round permanent residence or a private seasonal getaway for summer and winter fun, this property delivers a wonderful setting with an ideal balance of privacy and convenience. The open floor plan allows

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    18948 Garrett Hwy, Oakland, MD 21550
  • /41

    $485,000

    Sold Sep 22, 2025

    20160 Garrett Hwy Unit D310, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,379 Sq Ft
    • Built 1975

    Last Sold Summary

    • $352/SF
    • 41 Days On Market

    Last Listing Agent Stephanie Smith Select Premium Properties, Inc

    20160 Garrett Hwy Unit D310, Oakland, MD 21550
    • /67

      Est $239,038

      Not Listed For Sale

      655 Bray School Rd, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1984
      655 Bray School Rd, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Susan Bell Railey Realty, Inc.

  • /64

    $400,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 1,800 Sq Ft

    2967 Pysell Crosscut Rd, Oakland, MD 21550

    Discover the charm and comfort of this beautifully maintained manufactured home, nestled on a generous 2.07-acre lot. With a unique blend of rustic appeal and modern convenience, this property is perfect for those seeking a serene retreat without sacrificing accessibility. Step inside to find a warm and inviting interior with carpeting and laminate flooring that flows seamlessly throughout. The

    Larry Smith Railey Realty, Inc.

    2967 Pysell Crosscut Rd, Oakland, MD 21550
  • /11

    $5,000

    Sold Apr 03, 2026

    Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550

    • Land
    • 41,817 Sq Ft
    • $5,208 per Acre

    Last Sold Summary

    • 40 Days On Market

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550
    • /38

      Est $243,198

      Not Listed For Sale

      87 Mitchell Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,858 Sq Ft
      • Built 1971
      87 Mitchell Dr, Oakland, MD 21550

      Last Sold Summary

      • 28 Days On Market

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

  • /2

    $134,000

    • Land
    • 1 Acre
    • $134,000 per Acre

    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550

    Wooded lot with spectacular views of Paradise Point area of lake. Great privacy. Sewer tap available

    John Zorzit Eagle Commercial Realty

    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
  • /107

    $975,000

    Sold Jul 14, 2026

    1250 Pergin Farm Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,520 Sq Ft
    • Built 1980

    Last Sold Summary

    • $387/SF
    • 3 Days On Market

    Current Estimated Value $975,802

    Last Listing Agent Susan Bell Railey Realty, Inc.

    1250 Pergin Farm Rd, Oakland, MD 21550
    • /5

      Est $172,083

      Not Listed For Sale

      133 Fox Den Rd, Oakland, MD 21550

      • Built 1945
      133 Fox Den Rd, Oakland, MD 21550

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Michael Cumerlato Jason Mitchell Group

  • /47

    $384,500

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,476 Sq Ft

    321 Deer Park Hotel Rd, Oakland, MD 21550

    Double lots! Lot 4 & 5 of Hunting Ridge Estates will be sold together to bring up a total of .96 acre on your 2476 sqft. of finished living space home awaits you including your finished basement. Metal Roof is only 4 years old. Windows and doors are only 6 years old. Location, location...Welcome to 321 Deer Park Hotel Rd. where your mountain retreat will be just outside the city limits with only

    Pamela Debnam Houwzer, LLC

    321 Deer Park Hotel Rd, Oakland, MD 21550
  • /69

    $2,217,500

    Sold May 28, 2026

    2411 Lake Shore Dr, Oakland, MD 21550

    • 5 Beds
    • 4 Baths
    • 3,463 Sq Ft
    • Built 1979

    Last Sold Summary

    • 7% Below List Price
    • $640/SF
    • 7 Days On Market

    Current Estimated Value $2,266,458

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    2411 Lake Shore Dr, Oakland, MD 21550
    • /53

      Est $1,307,229

      Not Listed For Sale

      483 Skippers Point Rd, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,286 Sq Ft
      • Built 1983
      483 Skippers Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 127 Days On Market

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

  • /10

    $350,000

    • 5 Beds
    • 1.5 Baths
    • 1,536 Sq Ft

    511 Main St, Oakland, MD 21550

    The property offered for sale is 32.20 acres located on the southwest & northwest corners of Maryland Highway, State Route 135 at Main Street & Sand Flat Road, Deer Park. The Single Family Residence built in 1920 has 5 bedrooms, 1 full bathroom and 1 half bathroom. The residence is being sold "As Is". The residence is prime for renovation; the parcel may have commercial potential. The current

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    511 Main St, Oakland, MD 21550
  • /28

    $135,000

    Sold Sep 22, 2025

    320 Coolidge Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1900

    Last Sold Summary

    • $188/SF
    • 47 Days On Market

    Current Estimated Value $141,581

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    320 Coolidge Ave, Oakland, MD 21550
    • /35

      Est $96,000

      Not Listed For Sale

      830 N 4th St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,656 Sq Ft
      • Built 1930
      830 N 4th St, Oakland, MD 21550

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Andrew Orr The KW Collective

  • /6

    $4,000

    • Land
    • 20,037 Sq Ft
    • $8,696 per Acre

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550

    Here is an affordable chance to own a lot and have access to all of Youghiogheny Mountain Resort's beautiful and fun amenities!

    Jonathan Price Railey Realty, Inc.

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550
  • /74

    $915,000

    Sold Sep 15, 2025

    186 Thornberry Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,347 Sq Ft
    • Built 1992

    Last Sold Summary

    • $390/SF
    • 48 Days On Market

    Current Estimated Value $1,034,155

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

    186 Thornberry Rd, Oakland, MD 21550
    • /31

      Est $381,698

      Not Listed For Sale

      1793 Kempton Rd, Oakland, MD 21550

      • 5 Beds
      • 1 Bath
      • 2,280 Sq Ft
      • Built 1880
      1793 Kempton Rd, Oakland, MD 21550

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Linda Deremer Appalachian Realty

Showing Results 201 - 240, Page 6 of 18

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