10,739

Oakland, MD Homes

Section Image
    • /100

      Est $415,682 Not Listed For Sale

      3241 Pleasant Valley Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,496 Sq Ft
      • Built 1972
      3241 Pleasant Valley Rd, Oakland, MD 21550

      Last Sold Summary

      • 11% Above List Price
      • $150/SF
      • 69 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /7

    $24,900

    • Land
    • 4 Acres
    • $6,225 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
  • /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 $935,867

    Last Listing Agent Emillie Albrecht Real Broker, LLC

    145 Lower Penn Point Dr, Oakland, MD 21550
    • /61

      Est $283,066 Not Listed For Sale

      48 Spring Ln, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1977
      48 Spring Ln, Oakland, MD 21550

      Last Sold Summary

      • 13% Above List Price
      • $248/SF
      • 67 Days On Market

      Last Sold Price $249,999

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

  • /26

    $475,000

    • Land
    • 1.34 Acres
    • $354,478 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 up to two boat slips

    Nina Beitzel Railey Realty, Inc.

    LOT 25 Holy Cross Dr, 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 $1,432,702

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    20676 Garrett Hwy, Oakland, MD 21550
    • /22

      Est $494,832 Not Listed For Sale

      20917 Garrett Hwy, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 576 Sq Ft
      • Built 1940
      20917 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 10% Above List Price
      • $781/SF
      • 262 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Eric Crawford Taylor Made Deep Creek Real Estate

  • /32

    $275,000 Under Contract

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

    6485 Oakland Sang Run Rd, Oakland, MD 21550

    If you are looking for an updated one-level living home with a newer roof, new hot water heater, some new windows, and new flooring, this is a great option. Offering three bedrooms and an unfinished basement with endless possibilities for additional living space, plus a 1-car integrated garage. There are washer/dryer hookups on both the main and lower levels for added convenience. The exterior

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    6485 Oakland Sang Run Rd, 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 $290,311

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Real Estate

    506 Cedar Ln, Oakland, MD 21550
    • /35

      Est $280,419 Not Listed For Sale

      763 Pysell Crosscut Rd, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,854 Sq Ft
      • Built 1994
      763 Pysell Crosscut Rd, Oakland, MD 21550

      Last Sold Summary

      • $151/SF
      • 114 Days On Market

      Last Sold Price $280,000

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /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
  • /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
    • /36

      Est $235,505 Not Listed For Sale

      2607 Maryland Hwy, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,357 Sq Ft
      • Built 1970
      2607 Maryland Hwy, Oakland, MD 21550

      Last Sold Summary

      • 1% Above List Price
      • $172/SF
      • 4 Days On Market

      Last Sold Price $233,000

      Last Listing Agent Jarrod Harper Real Broker, LLC

  • /20

    $160,000

    • Land
    • 10.1 Acres
    • $15,842 per Acre

    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550

    Over 10 acres ready for developing off Dennett Rd. and Oakland Ave. Can be subdivided or could be large parcel to build your dream home, privacy off main streets with 3 separate entrances connecting to town roads. Engineered drawings for subdivision with grading permit in place at time of survey, is available and will be transferred with sale. (Potential up to 20 lots) Public sewar & water can be

    Julie Mead The KW Collective

    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, 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 Real Estate

    Lot 27 Stool Rock Rd, Oakland, MD 21550
    • /43

      Est $312,051 Not Listed For Sale

      37 Laurel Brook Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,120 Sq Ft
      • Built 1992
      37 Laurel Brook Dr, Oakland, MD 21550

      Last Sold Summary

      • 5% Above List Price
      • $140/SF
      • 47 Days On Market

      Last Sold Price $297,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /10

    $250,000 Pending

    • 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
  • /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

    Current Estimated Value $978,594

    Last Listing Agent Kathy Gibson Railey Realty, Inc.

    102 Mountainview Ct, Oakland, MD 21550
    • /37

      Est $235,915 Not Listed For Sale

      139 S Oakhall Dr, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 2,112 Sq Ft
      • Built 1962
      139 S Oakhall Dr, Oakland, MD 21550

      Last Sold Summary

      • 31% Above List Price
      • $85/SF
      • 171 Days On Market

      Last Sold Price $180,000

      Last Listing Agent Michaela Green 1 Real Estate Source LLC

  • /17

    $37,250

    • Land
    • 3.03 Acres
    • $12,294 per Acre

    Lot 1 Cherrywood Dr, Oakland, MD 21550

    ****NOW ONLY $37,250!! 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
  • /51

    $180,000 Sold Mar 20, 2026

    565 Glendale Rd Unit 204B, Oakland, MD 21550

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

    Last Sold Summary

    • $391/SF
    • 83 Days On Market

    Last Listing Agent Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 204B, Oakland, MD 21550
    • /64

      Est $1,528,718 Not Listed For Sale

      441 Paradise Heights, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 3,548 Sq Ft
      • Built 2002
      441 Paradise Heights, Oakland, MD 21550

      Last Sold Summary

      • 13% Above List Price
      • $380/SF
      • 148 Days On Market

      Last Sold Price $1,350,000

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

  • /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
  • /98

    $399,000 Sold Feb 13, 2026

    180 Paradise Ridge Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1979

    Last Sold Summary

    • $346/SF
    • 334 Days On Market

    Current Estimated Value $423,930

    Last Listing Agent Justin Liller Railey Realty, Inc.

    180 Paradise Ridge Rd, Oakland, MD 21550
    • /27

      Est $199,778 Not Listed For Sale

      32 Rockville Ct, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,056 Sq Ft
      • Built 2008
      32 Rockville Ct, Oakland, MD 21550

      Last Sold Summary

      • 198% Above List Price
      • $63/SF
      • 34 Days On Market

      Last Sold Price $67,000

      Last Listing Agent Michelle Haran Corner House Realty

  • /47

    $299,000 Under Contract

    • 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
  • /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 $572,276

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    793 Mountainview Dr, Oakland, MD 21550
    • /48

      Est $316,862 Not Listed For Sale

      314 Allegheny Dr, Oakland, MD 21550

      • 3 Beds
      • 3.5 Baths
      • 1,750 Sq Ft
      • Built 2007
      314 Allegheny Dr, Oakland, MD 21550

      Last Sold Summary

      • 9% Above List Price
      • $166/SF
      • 9 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Eric Crawford Taylor Made Deep Creek Real Estate

  • /19

    $295,000

    • Land
    • 8.48 Acres
    • $34,788 per Acre

    26 Green Brier Rd, Oakland, MD 21550

    8.48± acres offering excellent commercial or residential potential. Property features an existing well and septic system, with easy access and outstanding visibility. Conveniently located just minutes from the Oakland city limits outside of Zoning Districts. Ideal opportunity for development or investment.

    Rich Orr Railey Realty, Inc.

    26 Green Brier Rd, 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 $115,412

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    500 Seneca Ave, Oakland, MD 21550
    • /87

      Est $704,725 Not Listed For Sale

      34 Hooppole Ct, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,355 Sq Ft
      • Built 1975
      34 Hooppole Ct, Oakland, MD 21550

      Last Sold Summary

      • 3% Below List Price
      • $535/SF
      • 29 Days On Market

      Last Sold Price $725,000

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • /26

    $699,000 Under Contract

    • 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
  • /48

    $250,000 Sold Mar 27, 2026

    702 Sunshine Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 2009

    Last Sold Summary

    • 9% Below List Price
    • $135/SF
    • 16 Days On Market

    Current Estimated Value $267,122

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

    702 Sunshine Dr, Oakland, MD 21550
    • /87

      Est $453,771 Not Listed For Sale

      2702 Mayhew Inn Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1982
      2702 Mayhew Inn Rd, Oakland, MD 21550

      Last Sold Summary

      • 27% Above List Price
      • $233/SF
      • 9 Days On Market

      Last Sold Price $357,500

      Last Listing Agent Debbie Rogers Charis Realty Group

  • /2

    $69,900

    • 3 Beds
    • 1 Bath
    • 792 Sq Ft

    74 Parks Rd, Oakland, MD 21550

    **Investor Special with Mountain & Water Views**Opportunity is knocking at 74 Parks Road in Oakland, Maryland! This 3-bedroom, 1-bath one story is perfectly positioned just steps from the West Virginia line and surrounded by some of the most sought-after recreation in the region.Enjoy peaceful views of Snowy Creek right from the front yard and take advantage of being just minutes from

    Emillie Albrecht Real Broker, LLC

    74 Parks Rd, 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 $682,797

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

    94 Meadow Ct, Oakland, MD 21550
    • /42

      Est $180,400 Not Listed For Sale

      112 B St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1972
      112 B St, Oakland, MD 21550

      Last Sold Summary

      • 3% Above List Price
      • $182/SF
      • 23 Days On Market

      Last Sold Price $175,000

      Last Listing Agent Thomas Long Railey Realty, Inc.

  • /11

    $5,000 Pending

    • Land
    • 0.96 Acre
    • $5,208 per Acre

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

    Discover the perfect mountain getaway in Yough Mountain Resort, a gated community nestled in the scenic mountains of western Maryland, just minutes from Deep Creek Lake. This amenity-rich community offers an outdoor enthusiast’s dream with ATV and snowmobile trails, Yough River access, nearby state parks, hunting opportunities, plus a playground and pavilion area for gathering and relaxing.

    Mike Kennedy Railey Realty, Inc.

    Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550
  • /42

    $175,000 Sold May 09, 2025

    603 Oak St, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 1965

    Last Sold Summary

    • $146/SF
    • 49 Days On Market

    Current Estimated Value $184,756

    Last Listing Agent Andrew Orr The KW Collective

    603 Oak St, Oakland, MD 21550
    • /64

      Est $178,693 Not Listed For Sale

      608 I St, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,674 Sq Ft
      • Built 1900
      608 I St, Oakland, MD 21550

      Last Sold Summary

      • 10% Above List Price
      • $97/SF
      • 83 Days On Market

      Last Sold Price $163,000

      Last Listing Agent Melissa Long Railey Realty, Inc.

Showing Results 201 - 240, Page 6 of 18

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