10,731

Oakland, MD Homes

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    • 193 Red Run Rd Unit 1B1, Oakland, MD 21550
      193 Red Run Rd Unit 1B1, Oakland, MD 21550
      193 Red Run Rd Unit 1B1, Oakland, MD 21550
      /39

      Est $536,474 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      193 Red Run Rd Unit 1B1, Oakland, MD 21550

      193 Red Run Rd Unit 1B1, Oakland, MD 21550
  • 0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
    /2

    $149,000

    • Land
    • 1 Acre
    • $149,000 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
  • 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

    Current Estimated Value $654,681

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    5 Arrowhead Ln, Oakland, MD 21550
    • 193 Red Run Rd Unit 1A2, Oakland, MD 21550
      193 Red Run Rd Unit 1A2, Oakland, MD 21550
      193 Red Run Rd Unit 1A2, Oakland, MD 21550
      /38

      Est $528,309 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,300 Sq Ft

      193 Red Run Rd Unit 1A2, Oakland, MD 21550

      193 Red Run Rd Unit 1A2, 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
  • 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 Better Homes & Gardens Real Estate Old Line Group

    223 Old Crellin Rd, Oakland, MD 21550
    • 181 Skippers Point Rd, Oakland, MD 21550
      181 Skippers Point Rd, Oakland, MD 21550
      181 Skippers Point Rd, Oakland, MD 21550
      /84

      Est $907,663 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,209 Sq Ft

      181 Skippers Point Rd, Oakland, MD 21550

      181 Skippers Point Rd, Oakland, MD 21550
  • 1359 Cedar Ln, Oakland, MD 21550
    1359 Cedar Ln, Oakland, MD 21550
    1359 Cedar Ln, Oakland, MD 21550
    /37

    $275,000 Under Contract

    • 2 Beds
    • 1.5 Baths
    • 1,440 Sq Ft

    1359 Cedar Ln, Oakland, MD 21550

    Thoughtfully remodeled and full of charm, this beautiful cabin offers 2 cozy bedrooms and 1.5 baths with an open-concept layout, laminated hardwood flooring throughout, an updated kitchen, and a spacious family room that instantly feels warm and welcoming. Whether you’re gathering inside or stepping out to enjoy the inviting hot tub, fire pit, and both a front and side deck, this home is made for

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    1359 Cedar Ln, Oakland, MD 21550
  • 5459 Hutton Rd, Oakland, MD 21550
    5459 Hutton Rd, Oakland, MD 21550
    5459 Hutton Rd, Oakland, MD 21550
    /40

    $171,000 Sold May 30, 2025

    5459 Hutton Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1940

    Last Sold Summary

    • $86/SF
    • 113 Days On Market

    Current Estimated Value $175,146

    Last Listing Agent Debra Beitzel Long & Foster Real Estate, Inc.

    5459 Hutton Rd, Oakland, MD 21550
    • 3241 Pleasant Valley Rd, Oakland, MD 21550
      3241 Pleasant Valley Rd, Oakland, MD 21550
      3241 Pleasant Valley Rd, Oakland, MD 21550
      /100

      Est $430,180 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,496 Sq Ft

      3241 Pleasant Valley Rd, Oakland, MD 21550

      3241 Pleasant Valley 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
  • 13903 Garrett Hwy, Oakland, MD 21550
    13903 Garrett Hwy, Oakland, MD 21550
    13903 Garrett Hwy, Oakland, MD 21550
    /62

    $237,000 Sold Jun 13, 2025

    13903 Garrett Hwy, Oakland, MD 21550

    • 1 Bed
    • 3 Baths
    • 1,536 Sq Ft
    • Built 1977

    Last Sold Summary

    • $154/SF
    • 15 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    13903 Garrett Hwy, Oakland, MD 21550
    • 48 Spring Ln, Oakland, MD 21550
      48 Spring Ln, Oakland, MD 21550
      48 Spring Ln, Oakland, MD 21550
      /61

      Est $282,066 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,008 Sq Ft

      48 Spring Ln, Oakland, MD 21550

      48 Spring Ln, Oakland, MD 21550
  • 0 Rhododendron Unit MDGA2010748, Oakland, MD 21550
    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550
    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550
    /6

    $4,000

    • Land
    • 0.46 Acre
    • $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
  • Lots 54 & 53 Sloan Tract Rd, Oakland, MD 21550
    Lots 54 & 53 Sloan Tract Rd, Oakland, MD 21550
    Lots 54 & 53 Sloan Tract Rd, Oakland, MD 21550
    /12

    $154,900 Sold Aug 25, 2025

    Lots 54 & 53 Sloan Tract Rd, Oakland, MD 21550

    • Land
    • 0.6 Acre
    • $258,167 per Acre

    Last Sold Summary

    • 17 Days On Market

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    Lots 54 & 53 Sloan Tract Rd, Oakland, MD 21550
    • 72 Crabtree Hill, Oakland, MD 21550
      72 Crabtree Hill, Oakland, MD 21550
      72 Crabtree Hill, Oakland, MD 21550
      /48

      Est $484,528 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,006 Sq Ft

      72 Crabtree Hill, Oakland, MD 21550

      72 Crabtree Hill, 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
  • 145 Lower Penn Point Dr, Oakland, MD 21550
    145 Lower Penn Point Dr, Oakland, MD 21550
    145 Lower Penn Point Dr, Oakland, MD 21550
    /71

    $899,900 Sold Jun 26, 2025

    145 Lower Penn Point Dr, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,106 Sq Ft
    • Built 2007

    Last Sold Summary

    • $427/SF
    • 135 Days On Market

    Current Estimated Value $903,738

    Last Listing Agent Emillie Albrecht Real Broker, LLC

    145 Lower Penn Point Dr, Oakland, MD 21550
    • 20917 Garrett Hwy, Oakland, MD 21550
      20917 Garrett Hwy, Oakland, MD 21550
      20917 Garrett Hwy, Oakland, MD 21550
      /22

      Est $495,291 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 576 Sq Ft

      20917 Garrett Hwy, Oakland, MD 21550

      20917 Garrett Hwy, 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
  • 20676 Garrett Hwy, Oakland, MD 21550
    20676 Garrett Hwy, Oakland, MD 21550
    20676 Garrett Hwy, Oakland, MD 21550
    /58

    $1,425,000 Sold Oct 28, 2025

    20676 Garrett Hwy, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,280 Sq Ft
    • Built 2015

    Last Sold Summary

    • $625/SF
    • 17 Days On Market

    Current Estimated Value $1,414,882

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    20676 Garrett Hwy, Oakland, MD 21550
    • 763 Pysell Crosscut Rd, Oakland, MD 21550
      763 Pysell Crosscut Rd, Oakland, MD 21550
      763 Pysell Crosscut Rd, Oakland, MD 21550
      /35

      Est $294,510 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,854 Sq Ft

      763 Pysell Crosscut Rd, Oakland, MD 21550

      763 Pysell Crosscut Rd, Oakland, MD 21550
  • 729 E Oak St, Oakland, MD 21550
    729 E Oak St, Oakland, MD 21550
    729 E Oak St, Oakland, MD 21550
    /61

    $185,000

    • 3 Beds
    • 1.5 Baths
    • 1,170 Sq Ft

    729 E Oak St, Oakland, MD 21550

    Great, affordable starter home located in Oakland with public water and sewer, one car detached garage, hot water natural gas heat. Two bedroom and full bath on second level and possible third bedroom on main level with 1/2 bath. Cellar basement with mechanicals. Washer and Dryer hookups, washer/dryer convey, are located on the back enclosed porch which has electric baseboard heat. Enclosed front

    Kevin Liller Railey Realty, Inc.

    729 E Oak St, Oakland, MD 21550
  • 506 Cedar Ln, Oakland, MD 21550
    506 Cedar Ln, Oakland, MD 21550
    506 Cedar Ln, Oakland, MD 21550
    /35

    $285,000 Sold Jul 03, 2025

    506 Cedar Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1979

    Last Sold Summary

    • $212/SF
    • 16 Days On Market

    Current Estimated Value $285,401

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Vacations & Sales

    506 Cedar Ln, Oakland, MD 21550
    • 2607 Maryland Hwy, Oakland, MD 21550
      2607 Maryland Hwy, Oakland, MD 21550
      2607 Maryland Hwy, Oakland, MD 21550
      /36

      Est $235,803 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,357 Sq Ft

      2607 Maryland Hwy, Oakland, MD 21550

      2607 Maryland Hwy, 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 Under Contract

    • 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
  • 20160 Garrett Hwy Unit H712, Oakland, MD 21550
    20160 Garrett Hwy Unit H712, Oakland, MD 21550
    20160 Garrett Hwy Unit H712, Oakland, MD 21550
    /28

    $339,000 Sold Aug 01, 2025

    20160 Garrett Hwy Unit H712, Oakland, MD 21550

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

    Last Sold Summary

    • $753/SF
    • 124 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    20160 Garrett Hwy Unit H712, Oakland, MD 21550
    • 37 Laurel Brook Dr, Oakland, MD 21550
      37 Laurel Brook Dr, Oakland, MD 21550
      37 Laurel Brook Dr, Oakland, MD 21550
      /43

      Est $318,731 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,120 Sq Ft

      37 Laurel Brook Dr, Oakland, MD 21550

      37 Laurel Brook 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

    $250,000

    • Land
    • 2.07 Acres
    • $120,773 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
  • Lot 27 Stool Rock Rd, Oakland, MD 21550
    Lot 27 Stool Rock Rd, Oakland, MD 21550
    Lot 27 Stool Rock Rd, Oakland, MD 21550
    /4

    $3,000 Sold Oct 24, 2025

    Lot 27 Stool Rock Rd, Oakland, MD 21550

    • Land
    • 0.51 Acre
    • $5,882 per Acre

    Last Sold Summary

    • 67 Days On Market

    Last Listing Agent Elizabeth Broadwater Taylor Made Deep Creek Vacations & Sales

    Lot 27 Stool Rock Rd, Oakland, MD 21550
    • 139 S Oakhall Dr, Oakland, MD 21550
      139 S Oakhall Dr, Oakland, MD 21550
      139 S Oakhall Dr, Oakland, MD 21550
      /37

      Est $248,454 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,112 Sq Ft

      139 S Oakhall Dr, Oakland, MD 21550

      139 S Oakhall Dr, 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

    $38,000

    • Land
    • 3.03 Acres
    • $12,541 per Acre

    Lot 1 Cherrywood Dr, Oakland, MD 21550

    ****NOW ONLY $38,000!! 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.

    Amy Skipper Railey Realty, Inc.

    Lot 1 Cherrywood Dr, Oakland, MD 21550
  • 102 Mountainview Ct, Oakland, MD 21550
    102 Mountainview Ct, Oakland, MD 21550
    102 Mountainview Ct, Oakland, MD 21550
    /113

    $900,000 Sold Nov 14, 2025

    102 Mountainview Ct, Oakland, MD 21550

    • 7 Beds
    • 4.5 Baths
    • 5,376 Sq Ft
    • Built 2010

    Last Sold Summary

    • $167/SF
    • 139 Days On Market

    Last Listing Agent Kathy Gibson Railey Realty, Inc.

    102 Mountainview Ct, Oakland, MD 21550
    • 407 Bear Dr E, Oakland, MD 21550
      407 Bear Dr E, Oakland, MD 21550
      407 Bear Dr E, Oakland, MD 21550
      /56

      Est $369,565 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,440 Sq Ft

      407 Bear Dr E, Oakland, MD 21550

      407 Bear Dr E, Oakland, MD 21550
  • 1021 E High St, Oakland, MD 21550
    1021 E High St, Oakland, MD 21550
    1021 E High St, Oakland, MD 21550
    /58

    $234,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,520 Sq Ft

    1021 E High St, Oakland, MD 21550

    Nestled in the convenient High Street neighborhood of Oakland, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this well-maintained 3 Bedroom 2 Bath residence boasts 1,520 sq. ft. above grade finished sq. ft. and a partially finished full basement awaiting your finishing touches. The exterior showcases a welcoming façade with a well-kept yard,

    Andrew Eiswert Railey Realty, Inc.

    1021 E High St, Oakland, MD 21550
  • 793 Mountainview Dr, Oakland, MD 21550
    793 Mountainview Dr, Oakland, MD 21550
    793 Mountainview Dr, Oakland, MD 21550
    /42

    $545,000 Sold Sep 22, 2025

    793 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,564 Sq Ft
    • Built 1995

    Last Sold Summary

    • $348/SF
    • 23 Days On Market

    Current Estimated Value $557,787

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    793 Mountainview Dr, Oakland, MD 21550
    • 441 Paradise Heights, Oakland, MD 21550
      441 Paradise Heights, Oakland, MD 21550
      441 Paradise Heights, Oakland, MD 21550
      /64

      Est $1,444,325 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,548 Sq Ft

      441 Paradise Heights, Oakland, MD 21550

      441 Paradise Heights, Oakland, MD 21550
  • 43 Sloan Tract Rd, Oakland, MD 21550
    43 Sloan Tract Rd, Oakland, MD 21550
    43 Sloan Tract Rd, Oakland, MD 21550
    /47

    $324,900

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

    43 Sloan Tract Rd, Oakland, MD 21550

    Step back to the early days of Deep Creek Lake with this 4-bedroom, 2-bath home full of character and potential. Renovations are underway but unfinished, making this a true handyman or contractor special. Connected to public sewer, the home offers a head start for completing the kitchen and bathrooms and adding custom finishes to create a one-of-a-kind retreat. Enjoy views of Deep Creek Lake and

    Justin Liller Railey Realty, Inc.

    43 Sloan Tract Rd, Oakland, MD 21550
  • 500 Seneca Ave, Oakland, MD 21550
    500 Seneca Ave, Oakland, MD 21550
    500 Seneca Ave, Oakland, MD 21550
    /13

    $62,000 Sold Aug 01, 2025

    500 Seneca Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,284 Sq Ft
    • Built 1940

    Last Sold Summary

    • $48/SF
    • 577 Days On Market

    Current Estimated Value $81,956

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    500 Seneca Ave, Oakland, MD 21550
    • 32 Rockville Ct, Oakland, MD 21550
      32 Rockville Ct, Oakland, MD 21550
      32 Rockville Ct, Oakland, MD 21550
      /27

      Est $205,096 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,056 Sq Ft

      32 Rockville Ct, Oakland, MD 21550

      32 Rockville Ct, Oakland, MD 21550

Showing Results 201 - 240, Page 6 of 18

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