10,714

Oakland, MD Homes

Section Image
  • 254 Middleton Rd, Oakland, MD 21550
    254 Middleton Rd, Oakland, MD 21550
    254 Middleton Rd, Oakland, MD 21550
    /63

    $920,000 Sold Aug 22, 2025

    254 Middleton Rd, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 2,400 Sq Ft
    • Built 1994

    Last Sold Summary

    • $383/SF
    • 19 Days On Market

    Current Estimated Value $919,538

    Last Listing Agent Jon Bell Railey Realty, Inc.

    254 Middleton Rd, Oakland, MD 21550
    • 145 Ridgewood Dr, Oakland, MD 21550
      145 Ridgewood Dr, Oakland, MD 21550
      145 Ridgewood Dr, Oakland, MD 21550
      /72

      Est $650,766 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 3,838 Sq Ft

      145 Ridgewood Dr, Oakland, MD 21550

      145 Ridgewood Dr, Oakland, MD 21550
  • 511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    /33

    $180,000

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

    511 Main St, Oakland, MD 21550

    The property offered for sale is located on the southwest corner of Maryland Highway, State Route 135 and Main Street, Deer Park. It is 2.5 acres, more or less, which is part of Parcel 0069 Map 0073, containing 32.20 acres, more or less. The remaining 30.00 acres on the northwest side of Route 135 is not included. The 2.5 acres is an estimate of area and is subject to a survey for verification.

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    511 Main St, Oakland, MD 21550
  • 111 Knoll Crest Heights Dr, Oakland, MD 21550
    111 Knoll Crest Heights Dr, Oakland, MD 21550
    111 Knoll Crest Heights Dr, Oakland, MD 21550
    /33

    $150,000 Sold Dec 17, 2025

    111 Knoll Crest Heights Dr, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 3,504 Sq Ft
    • Built 1971

    Last Sold Summary

    • $43/SF
    • 48 Days On Market

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    111 Knoll Crest Heights Dr, Oakland, MD 21550
    • 4368 Underwood Rd, Oakland, MD 21550
      4368 Underwood Rd, Oakland, MD 21550
      4368 Underwood Rd, Oakland, MD 21550
      /61

      Est $249,296 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,760 Sq Ft

      4368 Underwood Rd, Oakland, MD 21550

      4368 Underwood Rd, Oakland, MD 21550
  • 0 Lot 28 Briarwood Ln Unit MDGA2008896, Oakland, MD 21550
    0 Lot 28 Briarwood Ln Unit MDGA2008896, Oakland, MD 21550
    0 Lot 28 Briarwood Ln Unit MDGA2008896, Oakland, MD 21550
    /6

    $119,000

    • Land
    • 3.05 Acres
    • $39,016 per Acre

    0 Lot 28 Briarwood Ln Unit MDGA2008896, Oakland, MD 21550

    This is the building site you've been waiting for! Lot 28 located in a subdivision called the view, it lives up to the name and offers 3.05 Acres. Prime location for a vacation rental, second home, or primary residence with filtered lake and mountain views. Northwestern orientation offers a chance for beautiful sunset views. Call today for more information!

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    0 Lot 28 Briarwood Ln Unit MDGA2008896, Oakland, MD 21550
  • 180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    /43

    $460,000 Sold Oct 24, 2025

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,200 Sq Ft
    • Built 2009

    Last Sold Summary

    • $209/SF
    • 16 Days On Market

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    • 2203 Lake Shore Dr, Oakland, MD 21550
      2203 Lake Shore Dr, Oakland, MD 21550
      2203 Lake Shore Dr, Oakland, MD 21550
      /83

      Est $1,640,974 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,403 Sq Ft

      2203 Lake Shore Dr, Oakland, MD 21550

      2203 Lake Shore Dr, Oakland, MD 21550
  • 0 Rhododendron Unit MDGA2010748, Oakland, MD 21550
    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550
    /2

    $4,000

    • Land
    • 0.46 Acre
    • $8,696 per Acre

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550

    Jonathan Price Railey Realty, Inc.

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550
  • 4960 Hutton Rd, Oakland, MD 21550
    4960 Hutton Rd, Oakland, MD 21550
    4960 Hutton Rd, Oakland, MD 21550
    /32

    $139,000 Sold Aug 15, 2025

    4960 Hutton Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • Built 1971

    Last Sold Summary

    • $129/SF
    • 205 Days On Market

    Current Estimated Value $140,934

    Last Listing Agent Justin Liller Railey Realty, Inc.

    4960 Hutton Rd, Oakland, MD 21550
    • 259 N Bradley Ln, Oakland, MD 21550
      259 N Bradley Ln, Oakland, MD 21550
      259 N Bradley Ln, Oakland, MD 21550
      /46

      Est $190,188 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 911 Sq Ft

      259 N Bradley Ln, Oakland, MD 21550

      259 N Bradley Ln, Oakland, MD 21550
  • Lot 7 Backbone Ridge Rd, Oakland, MD 21550
    Lot 7 Backbone Ridge Rd, Oakland, MD 21550
    Lot 7 Backbone Ridge Rd, Oakland, MD 21550
    /7

    $29,950

    • Land
    • 4 Acres
    • $7,488 per Acre

    Lot 7 Backbone Ridge Rd, Oakland, MD 21550

    This 4-acre building lot in the Backbone Ridge community offers breathtaking mountain views and a 3-bedroom perc approval — ready for your dream home. Perfectly positioned near Deep Creek Lake, WISP Ski Resort, Canaan Valley, Timberline Ski Resort, and Blackwater Falls State Park, outdoor adventure is just minutes away. Whether you're building a year-round residence or a weekend escape, enjoy the

    Brent Housley Railey Realty, Inc.

    Lot 7 Backbone Ridge Rd, Oakland, MD 21550
  • 297 Woodlands Hill Ln, Oakland, MD 21550
    297 Woodlands Hill Ln, Oakland, MD 21550
    297 Woodlands Hill Ln, Oakland, MD 21550
    /51

    $838,000 Sold Feb 19, 2025

    297 Woodlands Hill Ln, Oakland, MD 21550

    • 5 Beds
    • 5 Baths
    • 3,088 Sq Ft
    • Built 2008

    Last Sold Summary

    • $271/SF
    • 12 Days On Market

    Current Estimated Value $865,503

    Last Listing Agent Roberta McNamara RE/MAX Results

    297 Woodlands Hill Ln, Oakland, MD 21550
    • 2734 Mayhew Inn Rd, Oakland, MD 21550
      2734 Mayhew Inn Rd, Oakland, MD 21550
      2734 Mayhew Inn Rd, Oakland, MD 21550
      /58

      Est $479,321 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft

      2734 Mayhew Inn Rd, Oakland, MD 21550

      2734 Mayhew Inn Rd, Oakland, MD 21550
  • LOT 25 Holy Cross Dr, Oakland, MD 21550
    LOT 25 Holy Cross Dr, Oakland, MD 21550
    LOT 25 Holy Cross Dr, Oakland, MD 21550
    /25

    $499,999

    • Land
    • 1.34 Acres
    • $373,134 per Acre

    LOT 25 Holy Cross Dr, Oakland, MD 21550

    Discover the perfect blend of privacy, prestige, and natural beauty with Lot 25 in The Reserve at Holy Cross—a premier wooded lakefront homesite tucked into a serene private cove on Deep Creek Lake. Boasting 1.34 acres and an impressive 251 feet of lake frontage, this exceptional lot offers the ideal setting to build your dream retreat. Enjoy direct access to the water with two dedicated boat

    Steven Ritchie Railey Realty, Inc.

    LOT 25 Holy Cross Dr, Oakland, MD 21550
  • 202 Deerfield Dr, Oakland, MD 21550
    202 Deerfield Dr, Oakland, MD 21550
    202 Deerfield Dr, Oakland, MD 21550
    /72

    $310,000 Sold Jun 18, 2025

    202 Deerfield Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,720 Sq Ft
    • Built 1987

    Last Sold Summary

    • $114/SF
    • 128 Days On Market

    Current Estimated Value $334,479

    Last Listing Agent Sharon Murray Coldwell Banker Home Town Realty

    202 Deerfield Dr, Oakland, MD 21550
    • 1842 Stockslager Rd, Oakland, MD 21550
      1842 Stockslager Rd, Oakland, MD 21550
      1842 Stockslager Rd, Oakland, MD 21550
      /32

      Est $1,429,792 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,956 Sq Ft

      1842 Stockslager Rd, Oakland, MD 21550

      1842 Stockslager Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit 204B, Oakland, MD 21550
    565 Glendale Rd Unit 204B, Oakland, MD 21550
    565 Glendale Rd Unit 204B, Oakland, MD 21550
    /51

    $195,000

    • 1 Bed
    • 1 Bath
    • 460 Sq Ft

    565 Glendale Rd Unit 204B, Oakland, MD 21550

    Don’t miss this opportunity to own a beautifully updated 1-bedroom unit at Silver Tree Suites on Deep Creek Lake! This turn-key condo features recent flooring upgrades and is truly turn key, making it an ideal vacation retreat or income-producing rental. This particular unit offers a unique L-shaped layout, providing extra square footage and a more spacious feel compared to other efficiency

    Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 204B, Oakland, MD 21550
  • 220 N 11th St, Oakland, MD 21550
    220 N 11th St, Oakland, MD 21550
    220 N 11th St, Oakland, MD 21550
    /108

    $370,000 Sold Oct 10, 2025

    220 N 11th St, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 3,159 Sq Ft
    • Built 1972

    Last Sold Summary

    • $117/SF
    • 12 Days On Market

    Last Listing Agent Justin Liller Railey Realty, Inc.

    220 N 11th St, Oakland, MD 21550
    • 87 Mitchell Dr, Oakland, MD 21550
      87 Mitchell Dr, Oakland, MD 21550
      87 Mitchell Dr, Oakland, MD 21550
      /38

      Est $249,856 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,858 Sq Ft

      87 Mitchell Dr, Oakland, MD 21550

      87 Mitchell Dr, Oakland, MD 21550
  • Lot G Randall Way, Oakland, MD 21550
    Lot G Randall Way, Oakland, MD 21550
    Lot G Randall Way, Oakland, MD 21550
    /10

    $325,000

    • Land
    • 2.07 Acres
    • $157,005 per Acre

    Lot G Randall Way, Oakland, MD 21550

    Pergin Farm lake access lot with 2 acres and one boat slip. A private wooded setting in one of Deep Creeks most desirable, warm, and inviting locations.

    Russell Bounds Railey Realty, Inc.

    Lot G Randall Way, Oakland, MD 21550
  • 256 Jeffrey Ln Unit 28, Oakland, MD 21550
    256 Jeffrey Ln Unit 28, Oakland, MD 21550
    256 Jeffrey Ln Unit 28, Oakland, MD 21550
    /45

    $435,000 Sold Jul 02, 2025

    256 Jeffrey Ln Unit 28, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 1,838 Sq Ft
    • Built 2004

    Last Sold Summary

    • $237/SF
    • 626 Days On Market

    Current Estimated Value $434,341

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

    256 Jeffrey Ln Unit 28, Oakland, MD 21550
    • 133 Fox Den Rd, Oakland, MD 21550
      133 Fox Den Rd, Oakland, MD 21550
      133 Fox Den Rd, Oakland, MD 21550
      /5

      Est $155,663 Not Listed For Sale

      133 Fox Den Rd, Oakland, MD 21550

      133 Fox Den Rd, Oakland, MD 21550
  • Lot 1 Cherrywood Dr, Oakland, MD 21550
    Lot 1 Cherrywood Dr, Oakland, MD 21550
    Lot 1 Cherrywood Dr, Oakland, MD 21550
    /17

    $38,500

    • Land
    • 3.03 Acres
    • $12,706 per Acre

    Lot 1 Cherrywood Dr, Oakland, MD 21550

    NOW ONLY $38,500!! Discover the perfect blend of space, privacy, and convenience with this 3.03 acre lot, a short drive from downtown Oakland, Deep Creek Lake, Potomac State Forest and Garrett State Forest! With a 5-bedroom perc on file, this property is ready for your dream home. This beautiful property is located in Cherrywood Ridge Subdivision, with only 7 lots in the community. Underground

    Amy Skipper Railey Realty, Inc.

    Lot 1 Cherrywood Dr, Oakland, MD 21550
  • 181 Jeffrey Ln Unit 23D, Oakland, MD 21550
    181 Jeffrey Ln Unit 23D, Oakland, MD 21550
    181 Jeffrey Ln Unit 23D, Oakland, MD 21550
    /40

    $311,500 Sold Aug 22, 2025

    181 Jeffrey Ln Unit 23D, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 800 Sq Ft
    • Built 1997

    Last Sold Summary

    • $389/SF
    • 167 Days On Market

    Current Estimated Value $306,767

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

    181 Jeffrey Ln Unit 23D, Oakland, MD 21550
    • 830 N 4th St, Oakland, MD 21550
      830 N 4th St, Oakland, MD 21550
      830 N 4th St, Oakland, MD 21550
      /35

      Est $122,584 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,656 Sq Ft

      830 N 4th St, Oakland, MD 21550

      830 N 4th St, Oakland, MD 21550
  • 1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    /67

    $769,000

    • 5 Beds
    • 5 Baths
    • 3,664 Sq Ft

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    With a new price you don't want to miss this chance! Beautifully maintained 5 bedroom 5 bathroom lake area chalet. Beautifully landscaped and situated on 4 +/- acres with partial views of the south side of Deep Creek Lake. Recently Professionally appraised for $868,000! This home offers it's new owners a tremendous amount of room for storage and entertaining. As well as 3 levels of finished

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • 1473 Pergin Farm Rd, Oakland, MD 21550
    1473 Pergin Farm Rd, Oakland, MD 21550
    1473 Pergin Farm Rd, Oakland, MD 21550
    /79

    $925,000 Sold Oct 07, 2025

    1473 Pergin Farm Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,230 Sq Ft
    • Built 1945

    Last Sold Summary

    • $415/SF
    • 93 Days On Market

    Last Listing Agent Tony Migliaccio Long & Foster Real Estate, Inc.

    1473 Pergin Farm Rd, Oakland, MD 21550
    • 402 Leighton Dr, Oakland, MD 21550
      402 Leighton Dr, Oakland, MD 21550
      402 Leighton Dr, Oakland, MD 21550
      /70

      Est $259,135 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,332 Sq Ft

      402 Leighton Dr, Oakland, MD 21550

      402 Leighton Dr, Oakland, MD 21550
  • 12 Stool Rock Rd, Oakland, MD 21550
    12 Stool Rock Rd, Oakland, MD 21550
    12 Stool Rock Rd, Oakland, MD 21550
    /32

    $6,000

    • Land
    • 0.74 Acre
    • $8,108 per Acre

    12 Stool Rock Rd, Oakland, MD 21550

    Unbuildable membership lot in Yough Mtn Resort! Community amenities include common playground area, pavilion & community building, hunting and fishing areas as well as over 50 miles of private roads & trails for ATV riding. Call today for details!

    Michael Fenton Railey Realty, Inc.

    12 Stool Rock Rd, Oakland, MD 21550
  • 122 Earl Hauser Rd, Oakland, MD 21550
    122 Earl Hauser Rd, Oakland, MD 21550
    122 Earl Hauser Rd, Oakland, MD 21550
    /73

    $285,000 Sold Oct 06, 2025

    122 Earl Hauser Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft
    • Built 2012

    Last Sold Summary

    • $171/SF
    • 3 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    122 Earl Hauser Rd, Oakland, MD 21550
    • 404 Fairway Dr, Oakland, MD 21550
      404 Fairway Dr, Oakland, MD 21550
      404 Fairway Dr, Oakland, MD 21550
      /17

      Est $243,662 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,345 Sq Ft

      404 Fairway Dr, Oakland, MD 21550

      404 Fairway Dr, Oakland, MD 21550
  • 0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    /26

    $699,000

    • Land
    • 33.93 Acres
    • $20,601 per Acre

    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550

    Incredible Development Opportunity! Almost 34 acres of beautiful grounds zoned Residential/Industrial/Professional (RIP). This parcel would make a beautiful site for a single family or condo/townhome subdivision, business park, or industrial complex. Or, build your dream home with over 33 acres of privacy, yet close to schools, hospital, and downtown Oakland shopping. Public Water on site and

    Justin Liller Railey Realty, Inc.

    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
  • 464 Lake Forest Dr, Oakland, MD 21550
    464 Lake Forest Dr, Oakland, MD 21550
    464 Lake Forest Dr, Oakland, MD 21550
    /26

    $1,275,000 Sold Jun 02, 2025

    464 Lake Forest Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,496 Sq Ft
    • Built 1997

    Last Sold Summary

    • $511/SF
    • 277 Days On Market

    Current Estimated Value $1,293,843

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

    464 Lake Forest Dr, Oakland, MD 21550
    • 352 Fawn Dr, Oakland, MD 21550
      352 Fawn Dr, Oakland, MD 21550
      352 Fawn Dr, Oakland, MD 21550
      /49

      Est $272,699 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,408 Sq Ft

      352 Fawn Dr, Oakland, MD 21550

      352 Fawn Dr, Oakland, MD 21550
  • 565 Glendale Rd Unit 312, Oakland, MD 21550
    565 Glendale Rd Unit 312, Oakland, MD 21550
    565 Glendale Rd Unit 312, Oakland, MD 21550
    /31

    $229,000

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft

    565 Glendale Rd Unit 312, Oakland, MD 21550

    Seller will cover all 2026 HOA Dues at closing with an acceptable offer. Own your very own slice of peace and relaxation at Deep Creek Lake. The Suites at Silver Tree sits along 350 feet of private shoreline. The resort is a destination for many, and this unit (one of the top rental units in the building) produces an annual revenue of $25k+. One of only four loft units that has a private bedroom

    Sara Wells O'Malley EXP Realty, LLC

    565 Glendale Rd Unit 312, Oakland, MD 21550
  • 5 Arrowhead Ln, Oakland, MD 21550
    5 Arrowhead Ln, Oakland, MD 21550
    5 Arrowhead Ln, Oakland, MD 21550
    /92

    $635,000 Sold Sep 26, 2025

    5 Arrowhead Ln, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft
    • Built 1988

    Last Sold Summary

    • $385/SF
    • 116 Days On Market

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    5 Arrowhead Ln, Oakland, MD 21550
    • 1793 Kempton Rd, Oakland, MD 21550
      1793 Kempton Rd, Oakland, MD 21550
      1793 Kempton Rd, Oakland, MD 21550
      /31

      Est $347,026 Not Listed For Sale

      • 5 Beds
      • 1 Bath
      • 2,280 Sq Ft

      1793 Kempton Rd, Oakland, MD 21550

      1793 Kempton Rd, Oakland, MD 21550
  • 531 Glendale Rd Unit B302, Oakland, MD 21550
    531 Glendale Rd Unit B302, Oakland, MD 21550
    531 Glendale Rd Unit B302, Oakland, MD 21550
    /29

    $369,000

    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    531 Glendale Rd Unit B302, Oakland, MD 21550

    Experience effortless lakeside living at its finest in this spacious 2-bedroom, 1-bath unit in Silver Tree Suites—one of the largest units in the complex! This beautifully designed unit features an open floorplan centered around a cozy fireplace, perfect for relaxing after a day on the lake. A generous loft area creates a distinct separation between living and sleeping spaces, offering

    Larry Smith Railey Realty, Inc.

    531 Glendale Rd Unit B302, Oakland, MD 21550
  • 223 Old Crellin Rd, Oakland, MD 21550
    223 Old Crellin Rd, Oakland, MD 21550
    223 Old Crellin Rd, Oakland, MD 21550
    /6

    $180,000 Sold Apr 11, 2025

    223 Old Crellin Rd, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 980 Sq Ft
    • Built 1986

    Last Sold Summary

    • $184/SF
    • 67 Days On Market

    Last Listing Agent Garrett Shingler Realty One Group Generations

    223 Old Crellin Rd, Oakland, MD 21550

Showing Results 161 - 200, Page 5 of 18

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