10,714

Oakland, MD Homes

Section Image
    • 218 Weber Rd, Oakland, MD 21550
      218 Weber Rd, Oakland, MD 21550
      218 Weber Rd, Oakland, MD 21550
      /67

      Est $274,317 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,605 Sq Ft

      218 Weber Rd, Oakland, MD 21550

      218 Weber Rd, Oakland, MD 21550
  • 18 Hoye Crest Rd, Oakland, MD 21550
    18 Hoye Crest Rd, Oakland, MD 21550
    18 Hoye Crest Rd, Oakland, MD 21550
    /9

    $29,900 Pending

    • Land
    • 7.51 Acres
    • $3,981 per Acre

    18 Hoye Crest Rd, Oakland, MD 21550

    Discover this beautifully wooded 7.51-acre lot located in a scenic mountain development featuring the highest point in Maryland. With an approved 5-bedroom perc, this property is ready for your dream home or mountain getaway. Enjoy the peace and privacy of nature while still being part of an established community. Exceptionally priced at just $29,900!

    Kellyann Green Railey Realty, Inc.

    18 Hoye Crest Rd, 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 $172,338

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

    5459 Hutton Rd, Oakland, MD 21550
    • 589 Mountainview Dr, Oakland, MD 21550
      589 Mountainview Dr, Oakland, MD 21550
      589 Mountainview Dr, Oakland, MD 21550
      /71

      Est $878,724 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,665 Sq Ft

      589 Mountainview Dr, Oakland, MD 21550

      589 Mountainview Dr, Oakland, MD 21550
  • 444 Woodlands Hill Ln, Oakland, MD 21550
    444 Woodlands Hill Ln, Oakland, MD 21550
    444 Woodlands Hill Ln, Oakland, MD 21550
    /68

    $1,199,990

    • 4 Beds
    • 6 Baths
    • 4,744 Sq Ft

    444 Woodlands Hill Ln, Oakland, MD 21550

    Welcome to 444 Woodlands Hill Ln, in Oakland, MD. Nestled in the private community of The View, this custom home offers stunning lake views in a serene, private setting. Centrally located less than 4 miles from Wisp while backing up to hundreds of acres of untouched forest, this property truly offers the best that Deep Creek Lake has to offer. This luxury home has been impeccably maintained as a

    Corbin Griffith Compass

    444 Woodlands Hill Ln, 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
    • 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 $535,213 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
  • lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
    /15

    $39,000

    • Land
    • 2.57 Acres
    • $15,175 per Acre

    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550

    2 lots (7 & 8) totaling 2.57 acres, on gently sloping wooded area. Nestled between Cannan Valley & Deep Creek Lake, this promises to be a perfect blend of convenience and tranquility. Nature surrounds you - the perfect spot for a cozy cabin! Call agent for more information!

    Julie Mead The KW Collective

    lots 7 & 8 (2.57 ac) Valley Rd, 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
    • 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 $556,026 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
  • 125 N 2nd St, Oakland, MD 21550
    125 N 2nd St, Oakland, MD 21550
    125 N 2nd St, Oakland, MD 21550
    /7

    $115,000

    • Land
    • 0.22 Acre
    • $522,727 per Acre

    125 N 2nd St, Oakland, MD 21550

    Picture perfect level town lot on the highly sought after North 2nd Street in Oakland. Build your dream home in on the last remaining homesite on this historic and charming street located close to everything this great town has to offer! As an amazing "Feel Good" bonus, the seller is donating all proceeds from the sale to the incredible HART for Animals, Inc!!!Their mission is to help save

    Andrew Eiswert Railey Realty, Inc.

    125 N 2nd St, 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 $904,965

    Last Listing Agent Emillie Albrecht Real Broker, LLC

    145 Lower Penn Point Dr, 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 $963,795 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
  • 1720 Pysell Crosscut Rd, Oakland, MD 21550
    1720 Pysell Crosscut Rd, Oakland, MD 21550
    1720 Pysell Crosscut Rd, Oakland, MD 21550
    /114

    $999,999 Under Contract

    • 5 Beds
    • 5.5 Baths
    • 8,000 Sq Ft

    1720 Pysell Crosscut Rd, Oakland, MD 21550

    'Four Winds' is a Frank Lloyd Wright inspired masterpiece at Deep Creek Lake. Restored & renovated as recently as 2021, this 4/5BR home boasts 8000sf on nearly 5 acres of land. A small part of the home was converted to accommodate a successful medical practice - 2 patient rooms, bathroom & private office - which adds amazing potential to creatively 'work from home' in many professional fields

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    1720 Pysell Crosscut Rd, 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

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    20676 Garrett Hwy, 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 $430,894 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
  • 503 E Alder St, Oakland, MD 21550
    503 E Alder St, Oakland, MD 21550
    503 E Alder St, Oakland, MD 21550
    /8

    $246,691

    • 4 Beds
    • 2 Baths
    • 2,496 Sq Ft

    503 E Alder St, Oakland, MD 21550

    Investor’s Dream or Value-Seeker’s Opportunity | Queen Anne Victorian with Timeless Charm & Huge Potential This is the opportunity you’ve been waiting for—a true investor’s dream or the perfect chance for someone looking to buy a home at a low price and create exceptional value. This spacious and elegant Queen Anne Victorian combines historic beauty with incredible potential. The current owner

    Jameel Scott Coldwell Banker Realty

    503 E Alder 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 $282,535

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

    506 Cedar Ln, Oakland, MD 21550
    • 48 Spring Ln, Oakland, MD 21550
      48 Spring Ln, Oakland, MD 21550
      48 Spring Ln, Oakland, MD 21550
      /61

      Est $280,996 Not Listed For Sale

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

      48 Spring Ln, Oakland, MD 21550

      48 Spring Ln, Oakland, MD 21550
  • 60 Gorman St, Oakland, MD 21550
    60 Gorman St, Oakland, MD 21550
    60 Gorman St, Oakland, MD 21550
    /15

    $75,000

    • 3 Beds
    • 1 Bath
    • 1,488 Sq Ft

    60 Gorman St, Oakland, MD 21550

    Bring you vision to this 3-bedroom, 1 bath home right outside of Oakland, Maryland. Features a spacious living room, updated kitchen and a cozy front deck. With a little love and final touches, the property could shine again - ideal for a renovation project or investment opportunity. There is a nice yard and off street parking. Great opportunity for buyers looking to invest or customize a home to

    Jennifer Jackson Charis Realty Group

    60 Gorman St, 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
    • 72 Crabtree Hill, Oakland, MD 21550
      72 Crabtree Hill, Oakland, MD 21550
      72 Crabtree Hill, Oakland, MD 21550
      /48

      Est $476,855 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
  • 0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550
    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550
    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550
    /13

    $199,900 Pending

    • Land
    • 0.72 Acre
    • $277,639 per Acre

    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550

    Unique opportunity to purchase an accessory building in the heart Deep Creek Lake! Property was granted special exception to use for boat storage on Penn Point Rd. Less than a mile from Pawn Run Bar + Kitchen, this level wooded lot offers .72 acres and comes fully equipped with a brand new massive 32 x 38 garage. Fully insulated with oversized 10-foot doors, wrapped with metal roof and siding to

    Jon Bell Railey Realty, Inc.

    0 Penn Point Rd Unit MDGA2010762, 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
    • 20917 Garrett Hwy, Oakland, MD 21550
      20917 Garrett Hwy, Oakland, MD 21550
      20917 Garrett Hwy, Oakland, MD 21550
      /22

      Est $503,862 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 576 Sq Ft

      20917 Garrett Hwy, Oakland, MD 21550

      20917 Garrett Hwy, Oakland, MD 21550
  • 123 Mountainview Ct, Oakland, MD 21550
    123 Mountainview Ct, Oakland, MD 21550
    123 Mountainview Ct, Oakland, MD 21550
    /20

    $221,000

    • Land
    • 1.69 Acres
    • $130,769 per Acre

    123 Mountainview Ct, Oakland, MD 21550

    One of the best lake view lots at Deep Creek Lake! Big mountain and water views from this 1.67 acre homesite in the private community of Mountainside. Lake access with public sewer available. This lot sits at the top of the ridge with quiet surroundings, yet still close to Wisp Resort, marinas, restaurants, and local establishments. Mountainside offers a private marina club, tennis and basketball

    Jon Bell Railey Realty, Inc.

    123 Mountainview Ct, Oakland, MD 21550
  • 120 Gallatin Dr Unit 4, Oakland, MD 21550
    120 Gallatin Dr Unit 4, Oakland, MD 21550
    120 Gallatin Dr Unit 4, Oakland, MD 21550
    /64

    $590,000 Sold Jan 21, 2025

    120 Gallatin Dr Unit 4, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft
    • Built 2003

    Last Sold Summary

    • $372/SF
    • 68 Days On Market

    Current Estimated Value $585,895

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

    120 Gallatin Dr Unit 4, 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 $295,196 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
  • 511 E Green St, Oakland, MD 21550
    511 E Green St, Oakland, MD 21550
    511 E Green St, Oakland, MD 21550
    /37

    $289,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft

    511 E Green St, Oakland, MD 21550

    Completely renovated and move in ready, this charming Oakland home combines modern comfort with classic character. Every detail has been thoughtfully updated, including new wiring, insulation, roof, windows, flooring, and a beautiful kitchen, giving you peace of mind and a fresh, contemporary feel throughout. The main level features an open layout with a spacious living room that flows into the

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    511 E Green St, 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
    • 2607 Maryland Hwy, Oakland, MD 21550
      2607 Maryland Hwy, Oakland, MD 21550
      2607 Maryland Hwy, Oakland, MD 21550
      /36

      Est $234,491 Not Listed For Sale

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

      2607 Maryland Hwy, Oakland, MD 21550

      2607 Maryland Hwy, Oakland, MD 21550
  • 1019 Lake Shore Dr, Oakland, MD 21550
    1019 Lake Shore Dr, Oakland, MD 21550
    1019 Lake Shore Dr, Oakland, MD 21550
    /75

    $1,749,000

    • 4 Beds
    • 4.5 Baths
    • 2,605 Sq Ft

    1019 Lake Shore Dr, Oakland, MD 21550

    Tucked among the trees, Blue Spruce offers a perfect blend of modern comfort and serene natural beauty. This recently remodeled 4-bedroom, 4 and a half bathroom home invites you to relax, recharge, and reconnect with nature. With each bedroom offering an ensuite bathroom plus a half bath near the kitchen, this home was designed for comfort. Step inside to discover thoughtful updates throughout,

    Rachel Bruch Railey Realty, Inc.

    1019 Lake Shore Dr, 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
    • 37 Laurel Brook Dr, Oakland, MD 21550
      37 Laurel Brook Dr, Oakland, MD 21550
      37 Laurel Brook Dr, Oakland, MD 21550
      /43

      Est $329,253 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
  • 1260 Gnegy Church Rd, Oakland, MD 21550
    1260 Gnegy Church Rd, Oakland, MD 21550
    1260 Gnegy Church Rd, Oakland, MD 21550
    /58

    $449,000

    • 3 Beds
    • 3 Baths
    • 4,420 Sq Ft

    1260 Gnegy Church Rd, Oakland, MD 21550

    Discover space, privacy, and mountain charm on this stunning property nestled on over 76.03 +/- wooded acres. The home offers 3 bedrooms, 3 bathrooms, a spacious main level with open-concept living, and a partially finished upstairs ready for your personal touch. An attached garage, oversized detached garage, and expansive outdoor space provide endless possibilities—whether you’re seeking a

    Nina Beitzel Railey Realty, Inc.

    1260 Gnegy Church 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 $95,698

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    500 Seneca Ave, 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 $245,396 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
  • 141 Truesdale Rd, Oakland, MD 21550
    141 Truesdale Rd, Oakland, MD 21550
    141 Truesdale Rd, Oakland, MD 21550
    /29

    $185,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,834 Sq Ft

    141 Truesdale Rd, Oakland, MD 21550

    Bring your vision and put your own personal touch on this great starter home! This property has great bones and endless potential. Featuring three bedrooms, two and a half bathrooms, and a large/open family room; it’s ready for your creative touch. Offering a nice level yard on a dead-end lane, which feels very private. The attached 1-car garage and rear shed provide the perfect extra storage

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    141 Truesdale Rd, Oakland, MD 21550
  • 94 Meadow Ct, Oakland, MD 21550
    94 Meadow Ct, Oakland, MD 21550
    94 Meadow Ct, 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

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

    94 Meadow Ct, Oakland, MD 21550
    • 47 Mount Pleasant Ln, Oakland, MD 21550
      47 Mount Pleasant Ln, Oakland, MD 21550
      47 Mount Pleasant Ln, Oakland, MD 21550
      /56

      Est $318,665 Not Listed For Sale

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

      47 Mount Pleasant Ln, Oakland, MD 21550

      47 Mount Pleasant Ln, Oakland, MD 21550

Showing Results 201 - 240, Page 6 of 18

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