10,549

Oakland, MD Homes

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    • 8081 Oakland Sang Run Rd, Oakland, MD 21550
      8081 Oakland Sang Run Rd, Oakland, MD 21550
      8081 Oakland Sang Run Rd, Oakland, MD 21550
      /30

      Est $354,117

      Not Listed For Sale

      8081 Oakland Sang Run Rd, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 1,867 Sq Ft
      • Built 1941
      8081 Oakland Sang Run Rd, Oakland, MD 21550

      Last Sold Summary

      • 122 Days On Market

      Last Listing Agent ANGELA BOSLEY Taylor-Made Deep Creek Real Estate, LLC

  • 565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    /20

    $175,000

    • 1 Bed
    • 1 Bath
    • 527 Sq Ft

    565 Glendale Rd Unit 212 - A, Oakland, MD 21550

    Silver Tree Suites offers 350' of pristine shoreline at Deep Creek Lake with western exposure centrally located to all area amenities. Unit 212A offers a one level floorpan with private bedroom on the second floor of building A which offers easy access to the lobby, elevator, gym, sauna, game room and patio area overlooking the lake. Condominium ownership at Silver Tree Suites offers ease of

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
  • 135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    /36

    $326,000

    Sold Oct 10, 2025

    135 Jeffrey Ln Unit 19D, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1997

    Last Sold Summary

    • $272/SF
    • 42 Days On Market

    Current Estimated Value $334,445

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

    135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    • 180 Roman Ridge Rd Unit 18, Oakland, MD 21550
      180 Roman Ridge Rd Unit 18, Oakland, MD 21550
      180 Roman Ridge Rd Unit 18, Oakland, MD 21550
      /55

      Est $492,786

      Not Listed For Sale

      180 Roman Ridge Rd Unit 18, Oakland, MD 21550

      • 4 Beds
      • 4.5 Baths
      • 2,608 Sq Ft
      • Built 2005
      180 Roman Ridge Rd Unit 18, Oakland, MD 21550

      Last Sold Summary

      • 232 Days On Market

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

  • 24 Woodlands Hill Ln, Oakland, MD 21550
    24 Woodlands Hill Ln, Oakland, MD 21550
    24 Woodlands Hill Ln, Oakland, MD 21550
    /14

    $137,500

    • Land
    • 1.53 Acres
    • $89,869 per Acre

    24 Woodlands Hill Ln, Oakland, MD 21550

    Your Deep Creek dream starts here! Don't miss this beautiful 1.53-acre homesite in The View at Deep Creek Lake, where breathtaking mountain views and seasonal views of the lake create the perfect backdrop for your future home. Whether you're dreaming of a full-time residence, weekend escape, or investment property, you'll love the peaceful wooded setting and convenient location. Just minutes from

    Agent Photo

    Charlotte Savoy

    The KW Collective

    24 Woodlands Hill Ln, Oakland, MD 21550
  • 272 McComas Beach Terrace, Oakland, MD 21550
    272 McComas Beach Terrace, Oakland, MD 21550
    272 McComas Beach Terrace, Oakland, MD 21550
    /69

    $1,535,000

    Sold Jan 07, 2026

    272 McComas Beach Terrace, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,448 Sq Ft
    • Built 2005

    Last Sold Summary

    • $627/SF
    • 49 Days On Market

    Current Estimated Value $1,648,323

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    272 McComas Beach Terrace, Oakland, MD 21550
    • 142 Lemley Dr Unit I, Oakland, MD 21550
      142 Lemley Dr Unit I, Oakland, MD 21550
      142 Lemley Dr Unit I, Oakland, MD 21550
      /26

      Est $366,368

      Not Listed For Sale

      142 Lemley Dr Unit I, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • Built 1987
      142 Lemley Dr Unit I, Oakland, MD 21550

      Last Sold Summary

      • 146 Days On Market

      Last Listing Agent Andrew Eiswert Railey Realty, Inc.

  • 113 Jubb Meadows Ln, Oakland, MD 21550
    113 Jubb Meadows Ln, Oakland, MD 21550
    113 Jubb Meadows Ln, Oakland, MD 21550
    /69

    $869,900

    $30K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,185 Sq Ft

    113 Jubb Meadows Ln, Oakland, MD 21550

    Luxury Estate just outside the town of Oakland. This 4-bed, 3.5 bath is situated on 9.72 acres. Offering 4,555 sq ft with vaulted ceilings, open concept living, and a rustic stacked stone fireplace. Modern gourmet kitchen with a large island and granite tops. Hardwood floors and timber frame accents throughout. Attached three-car garage. Full unfinished basement ready to add up to an additional

    Jon Bell Railey Realty, Inc.

    113 Jubb Meadows Ln, Oakland, MD 21550
  • 0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550
    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550
    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550
    /33

    $425,000

    Sold Dec 19, 2025

    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2025

    Last Sold Summary

    • $283/SF
    • 0 Days On Market

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

    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550
    • 19956 Garrett Hwy Unit 2, Oakland, MD 21550
      19956 Garrett Hwy Unit 2, Oakland, MD 21550
      19956 Garrett Hwy Unit 2, Oakland, MD 21550
      /57

      Est $1,119,160

      Not Listed For Sale

      19956 Garrett Hwy Unit 2, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 3,012 Sq Ft
      • Built 2007
      19956 Garrett Hwy Unit 2, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

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

  • 428 Sam Snead Cir, Oakland, MD 21550
    428 Sam Snead Cir, Oakland, MD 21550
    428 Sam Snead Cir, Oakland, MD 21550
    /86

    $579,000

    $20K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,542 Sq Ft

    428 Sam Snead Cir, Oakland, MD 21550

    Welcome to this beautifully appointed 5-bedroom, 3.5-bath home located in one of Oakland’s most desirable neighborhoods—Country Club Acres, bordering The Golf Club at Oakland. Offering the perfect blend of modern style, comfort, and convenience, this spacious home is designed to accommodate both everyday living and entertaining.Step inside to discover an inviting open-concept floor plan

    Justin Liller Railey Realty, Inc.

    428 Sam Snead Cir, Oakland, MD 21550
  • 329 Lemley Dr, Oakland, MD 21550
    329 Lemley Dr, Oakland, MD 21550
    329 Lemley Dr, Oakland, MD 21550
    /81

    $700,000

    Sold Feb 26, 2026

    329 Lemley Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,632 Sq Ft
    • Built 2004

    Last Sold Summary

    • $266/SF
    • 112 Days On Market

    Current Estimated Value $738,115

    Last Listing Agent Jon Bell Railey Realty, Inc.

    329 Lemley Dr, Oakland, MD 21550
    • 149 Gobbler Run Rd, Oakland, MD 21550
      149 Gobbler Run Rd, Oakland, MD 21550
      149 Gobbler Run Rd, Oakland, MD 21550
      /15

      Est $111,131

      Not Listed For Sale

      149 Gobbler Run Rd, Oakland, MD 21550

      • Built 2006
      149 Gobbler Run Rd, Oakland, MD 21550

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Sherry Nally Berkshire Hathaway HomeServices Homesale Realty

  • 20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    /68

    $575,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550

    With some minor modifications to the unit, it is possible for this condo to be rented as two separate condos (501 two BR and 701 one BR). Lakefront living at it's best can be found in this completely renovated spacious condo. This three-level unit is the perfect place to get away together! With space to come together and space to escape, this unit promises both privacy and togetherness for a

    Kevin Liller Railey Realty, Inc.

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
  • 3930 Mayhew Inn Rd, Oakland, MD 21550
    3930 Mayhew Inn Rd, Oakland, MD 21550
    3930 Mayhew Inn Rd, Oakland, MD 21550
    /18

    $360,000

    Sold Jun 24, 2026

    3930 Mayhew Inn Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft
    • Built 2000

    Last Sold Summary

    • 10% Below List Price
    • $162/SF
    • 44 Days On Market

    Current Estimated Value $392,891

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

    3930 Mayhew Inn Rd, Oakland, MD 21550
    • 1506 Broadford Rd, Oakland, MD 21550
      1506 Broadford Rd, Oakland, MD 21550
      1506 Broadford Rd, Oakland, MD 21550
      /98

      Est $467,818

      Not Listed For Sale

      1506 Broadford Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,048 Sq Ft
      • Built 2023
      1506 Broadford Rd, Oakland, MD 21550

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • 5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    /67

    $385,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    5024 Cranesville Rd, Oakland, MD 21550

    Surrounded by 100+ Acres of Nature Conservancy conservation lands, on a 1.68-acre scenic home site, this 3-bedroom, 2.5-bath home combines natural charm with modern comfort. The native stone exterior and peaceful setting set the tone for this inviting residence. The wrap around deck is perfect for quiet time with beautiful views. Inside, the main level features a spacious primary bedroom suite,

    Rich Orr Railey Realty, Inc.

    5024 Cranesville Rd, Oakland, MD 21550
  • 0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550
    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550
    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550
    /18

    $19,500

    Sold Sep 04, 2025

    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550

    • Land
    • 1.48 Acres
    • $13,176 per Acre

    Last Sold Summary

    • 348 Days On Market

    Last Listing Agent Brady Harden Coldwell Banker Premier

    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550
    • 812 Winter Place, Oakland, MD 21550
      812 Winter Place, Oakland, MD 21550
      812 Winter Place, Oakland, MD 21550
      /4

      Est $37,834

      Not Listed For Sale

      812 Winter Place, Oakland, MD 21550

      812 Winter Place, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

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

  • 1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    /59

    $359,000

    $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    1167 Tall Oaks Dr, Oakland, MD 21550

    Log cabin on 11 private acres. Located in the gated Timbers on the Yough community. The community features shared access to the Youghiogheny River. Home features include spacious covered deck, newly installed walkway, exterior fire pit, breakfast bar, and pellet stove. Heart pine floors on main floor and stairs, reclaimed from RJ Reynolds tobacco factory built around 1900! The primary bath offers

    Kellyann Green Railey Realty, Inc.

    1167 Tall Oaks Dr, Oakland, MD 21550
  • 290 Crellin Underwood Rd, Oakland, MD 21550
    290 Crellin Underwood Rd, Oakland, MD 21550
    290 Crellin Underwood Rd, Oakland, MD 21550
    /65

    $280,500

    Sold Sep 12, 2025

    290 Crellin Underwood Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,208 Sq Ft
    • Built 1982

    Last Sold Summary

    • $127/SF
    • 96 Days On Market

    Current Estimated Value $295,463

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    290 Crellin Underwood Rd, Oakland, MD 21550
    • 51 Stag Run, Oakland, MD 21550
      51 Stag Run, Oakland, MD 21550
      51 Stag Run, Oakland, MD 21550
      /26

      Not Listed For Sale

      51 Stag Run, Oakland, MD 21550

      51 Stag Run, Oakland, MD 21550

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • 328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    /134

    $545,000

    • 4 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    328 Stool Rock Rd, Oakland, MD 21550

    Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of craftsmanship featuring handmade woodwork crafted from trees sourced directly from the property. Many specialty items will remain, including bathroom vanities, multiple dressers, a primary suite custom TV console, a built-in bunk bed, and more. The spacious primary suite was added in 2016 and offers a separate

    Kathy Gibson Railey Realty, Inc.

    328 Stool Rock Rd, Oakland, MD 21550
  • 9 Timber Falls Rd, Oakland, MD 21550
    9 Timber Falls Rd, Oakland, MD 21550
    9 Timber Falls Rd, Oakland, MD 21550
    /25

    $28,000

    Sold Jun 02, 2026

    9 Timber Falls Rd, Oakland, MD 21550

    • Land
    • 6.9 Acres
    • $4,058 per Acre

    Last Sold Summary

    • 220 Days On Market

    Last Listing Agent Jesse Shimrock Railey Realty, Inc.

    9 Timber Falls Rd, Oakland, MD 21550
    • 189 Maple Del Ln, Oakland, MD 21550
      189 Maple Del Ln, Oakland, MD 21550
      189 Maple Del Ln, Oakland, MD 21550
      /62

      Est $510,658

      Not Listed For Sale

      189 Maple Del Ln, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,260 Sq Ft
      • Built 2003
      189 Maple Del Ln, Oakland, MD 21550

      Last Sold Summary

      • 87 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • 130 Timberloft Cir Unit 14, Oakland, MD 21550
    130 Timberloft Cir Unit 14, Oakland, MD 21550
    130 Timberloft Cir Unit 14, Oakland, MD 21550
    /79

    $749,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft

    130 Timberloft Cir Unit 14, Oakland, MD 21550

    Centrally located in the heart of Deep Creek Lake, this beautifully maintained 3 bedroom, 3 bath home offers breathtaking lake and mountain views year round. Designed with an open floor plan, this home is perfect for entertaining. Enjoy the stunning scenery from the spacious main-level deck, or relax in the screened-in lower level porch. A cozy fireplace on both levels adds warmth and charm,

    Nicole Jackson Railey Realty, Inc.

    130 Timberloft Cir Unit 14, Oakland, MD 21550
  • 12 Arrowhead Ln, Oakland, MD 21550
    12 Arrowhead Ln, Oakland, MD 21550
    12 Arrowhead Ln, Oakland, MD 21550
    /59

    $707,500

    Sold Aug 14, 2026

    12 Arrowhead Ln, Oakland, MD 21550

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

    Last Sold Summary

    • 4% Below List Price
    • $429/SF
    • 29 Days On Market

    Current Estimated Value $683,362

    Last Listing Agent Julie Mead The KW Collective

    12 Arrowhead Ln, Oakland, MD 21550
    • 40 Allen Dr, Oakland, MD 21550
      40 Allen Dr, Oakland, MD 21550
      40 Allen Dr, Oakland, MD 21550
      /45

      Est $711,855

      Not Listed For Sale

      40 Allen Dr, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,781 Sq Ft
      • Built 1999
      40 Allen Dr, Oakland, MD 21550

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • 256 Jeffrey Ln Unit 28, Oakland, MD 21550
    256 Jeffrey Ln Unit 28, Oakland, MD 21550
    256 Jeffrey Ln Unit 28, Oakland, MD 21550
    /65

    $464,900

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

    256 Jeffrey Ln Unit 28, Oakland, MD 21550

    Looking for a beautifully updated condo at Deep Creek Lake? Welcome to 256 Jeffrey Lane #28, a spacious 3-bedroom, 3.5-bath condo in the desirable Traders Landing community. Enjoy filtered lake views from this well-appointed home, conveniently located just across the street from the water and only minutes from Wisp Resort, restaurants, shopping, marinas, and other area attractions. With a

    Larry Smith Railey Realty, Inc.

    256 Jeffrey Ln Unit 28, Oakland, MD 21550
  • 502 E Oak St, Oakland, MD 21550
    502 E Oak St, Oakland, MD 21550
    502 E Oak St, Oakland, MD 21550
    /41

    $239,900

    Sold Sep 12, 2025

    502 E Oak St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1956

    Last Sold Summary

    • $143/SF
    • 17 Days On Market

    Current Estimated Value $249,014

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    502 E Oak St, Oakland, MD 21550
    • 319 Basswood Way Unit LOT 21, Oakland, MD 21550
      319 Basswood Way Unit LOT 21, Oakland, MD 21550
      319 Basswood Way Unit LOT 21, Oakland, MD 21550
      /32

      Not Listed For Sale

      319 Basswood Way Unit LOT 21, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,784 Sq Ft
      • Built 2007
      319 Basswood Way Unit LOT 21, Oakland, MD 21550

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • 47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    /109

    $6,499,900

    • 7 Beds
    • 8.5 Baths
    • 11,417 Sq Ft

    47 Holy Cross Cir, Oakland, MD 21550

    Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with

    Jon Bell Railey Realty, Inc.

    47 Holy Cross Cir, Oakland, MD 21550
  • 131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    /53

    $495,000

    Sold Oct 08, 2025

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,422 Sq Ft
    • Built 2004

    Last Sold Summary

    • $204/SF
    • 106 Days On Market

    Current Estimated Value $483,207

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

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    • 48 Skippers Estates Dr, Oakland, MD 21550
      48 Skippers Estates Dr, Oakland, MD 21550
      48 Skippers Estates Dr, Oakland, MD 21550
      /61

      Est $579,721

      Not Listed For Sale

      48 Skippers Estates Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,454 Sq Ft
      • Built 1984
      48 Skippers Estates Dr, Oakland, MD 21550

      Last Sold Summary

      • 160 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • 163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    /60

    $279,000

    $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,242 Sq Ft

    163 Mitchell Dr, Oakland, MD 21550

    Nestled in the charming Mitchell Manor community, this delightful split-level home offers a perfect blend of comfort and style. With 2,242 square feet of thoughtfully designed living space, this residence features three spacious bedrooms and two and a half bathrooms, ideal for both relaxation and entertaining. There is also a walk-in closet/dressing room to die for! Step inside to discover an

    Andrew Eiswert Railey Realty, Inc.

    163 Mitchell Dr, Oakland, MD 21550
  • 62 Middleton Rd, Oakland, MD 21550
    62 Middleton Rd, Oakland, MD 21550
    62 Middleton Rd, Oakland, MD 21550
    /67

    $760,000

    Sold Nov 14, 2025

    62 Middleton Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,397 Sq Ft
    • Built 1993

    Last Sold Summary

    • $317/SF
    • 113 Days On Market

    Current Estimated Value $797,633

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Middleton Rd, Oakland, MD 21550
    • 33 Black Bear Ct, Oakland, MD 21550
      33 Black Bear Ct, Oakland, MD 21550
      33 Black Bear Ct, Oakland, MD 21550
      /80

      Est $886,415

      Not Listed For Sale

      33 Black Bear Ct, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,976 Sq Ft
      • Built 1989
      33 Black Bear Ct, Oakland, MD 21550

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • 101 Sobriety Way, Oakland, MD 21550
    101 Sobriety Way, Oakland, MD 21550
    101 Sobriety Way, Oakland, MD 21550
    /72

    $499,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    101 Sobriety Way, Oakland, MD 21550

    Wake up to breathtaking views of Deep Creek Lake every single day from this beautifully updated 3-bedroom home, complete with private lake access in a quiet, peaceful cove. Huge windows throughout invite in an abundance of natural light while framing the surrounding scenery, blurring the line between indoors and out. The open-concept kitchen features beautiful new quartz countertops and flows

    Brent Housley Railey Realty, Inc.

    101 Sobriety Way, Oakland, MD 21550
  • 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 $976,771

    Last Listing Agent Jon Bell Railey Realty, Inc.

    254 Middleton Rd, Oakland, MD 21550
    • 36 Cherokee Ln, Oakland, MD 21550
      36 Cherokee Ln, Oakland, MD 21550
      36 Cherokee Ln, Oakland, MD 21550
      /62

      Est $184,988

      Not Listed For Sale

      36 Cherokee Ln, Oakland, MD 21550

      • 2 Beds
      • 1.5 Baths
      • 864 Sq Ft
      • Built 1976
      36 Cherokee Ln, Oakland, MD 21550

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Justin Liller Railey Realty, Inc.

Showing Results 81 - 120, Page 3 of 18

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