10,731

Oakland, MD Homes

Section Image Section Image
  • /47

    $180,000 Sold Nov 24, 2025

    627 Hamill St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,322 Sq Ft
    • Built 1886

    Last Sold Summary

    • $136/SF
    • 2 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    627 Hamill St, Oakland, MD 21550
    • /21

      Est $122,318 Not Listed For Sale

      409 San Francisco St, Oakland, MD 21550

      409 San Francisco St, Oakland, MD 21550
  • /21

    $22,500

    • Land
    • 0.58 Acre
    • $38,793 per Acre

    Lot 13 Dogwood Dr, Oakland, MD 21550

    Discover the perfect blend of privacy and potential with these two adjoining lots located in the Youghiogheny Mountain Resort community. Lot 13 Dogwood Drive offers 0.58 wooded acres of mountain serenity. Lot 13 is approved for a sand mound septic system, making it an ideal site for your future mountain cabin or getaway retreat. The community offers gated access, over 50 miles of community roads

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 875-5545

    Lot 13 Dogwood Dr, Oakland, MD 21550
  • /14

    $17,000 Sold Dec 18, 2025

    Lot 5A Valley Rd, Oakland, MD 21550

    • Land
    • 2.45 Acres
    • $6,939 per Acre

    Last Sold Summary

    • 1,047 Days On Market

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

    Lot 5A Valley Rd, Oakland, MD 21550
    • /22

      Not Listed For Sale

      • 4 Beds

      1 Overlook Ridge Dr SE, Oakland, MD 21550

      1 Overlook Ridge Dr SE, Oakland, MD 21550
  • /31

    $130,000

    • Land
    • 2.1 Acres
    • $61,905 per Acre

    Lot 20 Paradise Ridge Rd, Oakland, MD 21550

    Discover the perfect setting for your mountain retreat in the Paradise Ridge community at Deep Creek Lake. This beautiful 2.10 acre wooded lot is tucked away on a quiet cul-de-sac, offering privacy, natural surroundings, and a peaceful atmosphere. The property has already been approved for a conventional septic system, making it an ideal choice for building your dream home or vacation getaway.

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 526-7577

    Lot 20 Paradise Ridge Rd, Oakland, MD 21550
  • /24

    $27,500 Sold May 14, 2025

    107 E Mason St, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,256 Sq Ft
    • Built 1914

    Last Sold Summary

    • $12/SF
    • 18 Days On Market

    Current Estimated Value $180,059

    Last Listing Agent Kathleen Miller Better Homes & Gardens Real Estate Old Line Group

    107 E Mason St, Oakland, MD 21550
    • /48

      Not Listed For Sale

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

      20160 Garrett Hwy Unit 502/702, Oakland, MD 21550

      20160 Garrett Hwy Unit 502/702, Oakland, MD 21550
  • /60

    $299,000

    • 4 Beds
    • 2 Baths
    • 1,913 Sq Ft

    127 S Oakhall Dr, Oakland, MD 21550

    Welcome to this well maintained 4-bed, 2-bath ranch home on a generous corner lot in Oakland, MD. Inviting curb appeal with stone exterior and mature landscaping sets the tone. Step inside to a bright and spacious main level featuring gleaming hardwood floors, a large eat-in kitchen with ample cabinetry, and an open living area perfect for gatherings. Enjoy three main-level bedrooms and a full

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 792-8710

    127 S Oakhall Dr, Oakland, MD 21550
  • /32

    $260,000 Sold Jul 21, 2025

    29 Sloan Tract Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1983

    Last Sold Summary

    • $271/SF
    • 98 Days On Market

    Current Estimated Value $281,355

    Last Listing Agent Thomas Long Railey Realty, Inc.

    29 Sloan Tract Rd, Oakland, MD 21550
    • /64

      Est $640,121 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 3,300 Sq Ft

      305 Winding Trail Ln Unit 12A, Oakland, MD 21550

      305 Winding Trail Ln Unit 12A, Oakland, MD 21550
  • /55

    $275,000

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

    702 Sunshine Dr, Oakland, MD 21550

    Welcome to easy, one-level living at 702 Sunshine Dr! This well-maintained 3-bedroom, 2-bath home offers a functional layout with everything you need on one floor. Enjoy the convenience of an attached garage, a fenced backyard, and a covered back porch—perfect for morning coffee, outdoor dining, or relaxing in any weather. Located just minutes from downtown Oakland, this home puts you close to

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 905-4746

    702 Sunshine Dr, Oakland, MD 21550
  • /82

    $1,900,000 Sold May 16, 2025

    228 Paradise Heights, Oakland, MD 21550

    • 4 Beds
    • 4.5 Baths
    • 2,249 Sq Ft
    • Built 1989

    Last Sold Summary

    • $845/SF
    • 5 Days On Market

    Current Estimated Value $1,876,016

    Last Listing Agent Jay Quinn Taylor Made Deep Creek Vacations & Sales

    228 Paradise Heights, Oakland, MD 21550
    • /24

      Est $183,990 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft

      77 Racoon Dr, Oakland, MD 21550

      77 Racoon Dr, Oakland, MD 21550
  • /9

    $275,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 875 Sq Ft

    127 Jeffrey Ln Unit 18C, Oakland, MD 21550

    Welcome to 127 Jeffrey Lane 18C! Centrally located at Deep Creek Lake, this unit offers convenience year round to restaurants, skiing, golf courses, Deep Creek Lake and even one of the areas most desired coffee shops just a few hundred feet away. Enjoy northeastern exposure for great sunrises overlooking the lake. The main level offers a kitchen, living room with wood burning fireplace, 2

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (301) 591-6157

    127 Jeffrey Ln Unit 18C, Oakland, MD 21550
  • /29

    $369,900 Sold Oct 17, 2025

    366 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Built 1997

    Last Sold Summary

    • $266/SF
    • 152 Days On Market

    Current Estimated Value $371,210

    Last Listing Agent Adam Belasco Keller Williams Capital Properties

    366 Glendale Rd, Oakland, MD 21550
    • /46

      Est $308,905 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 550 Sq Ft

      157 Jeffrey Ln Unit 21B, Oakland, MD 21550

      157 Jeffrey Ln Unit 21B, Oakland, MD 21550
  • /18

    $44,900

    • Land
    • 6.12 Acres
    • $7,337 per Acre

    Lot 6 Hoye Crest Rd, Oakland, MD 21550

    Opportunity to own over 6 acres on Backbone Mountain adjoining the Highest Point in Maryland! This lot will offer some of the best views from Maryland's highest point with western exposure. Approved perc and electric to site, ready for you to build your dream home! Residential community. No camping, no hunting. Call today to schedule a time too see this remarkable property!

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 652-2465

    Lot 6 Hoye Crest Rd, Oakland, MD 21550
  • /69

    $450,000 Sold Feb 26, 2025

    1014 Madison St, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,016 Sq Ft
    • Built 1988

    Last Sold Summary

    • $149/SF
    • 21 Days On Market

    Current Estimated Value $464,970

    Last Listing Agent Justin Liller Railey Realty, Inc.

    1014 Madison St, Oakland, MD 21550
    • /45

      Est $1,267,851 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,470 Sq Ft

      20230 Garrett Hwy, Oakland, MD 21550

      20230 Garrett Hwy, Oakland, MD 21550
  • /50

    $315,000

    • 3 Beds
    • 2.5 Baths
    • 1,416 Sq Ft

    163 Crestview Dr, Oakland, MD 21550

    Welcome to 163 Crestview Drive — a beautifully maintained 3-bedroom, 2.5-bath home nestled in the Mitchell Manor neighborhood. This inviting Cape Cod offers timeless charm, modern updates, and a peaceful setting just minutes from downtown Oakland. Many recent improvements including HVAC, water treatment/filtration system, flooring and landscaping! Step inside to an open, light-filled floor plan

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 502-1143

    163 Crestview Dr, Oakland, MD 21550
  • /4

    $250,000 Sold Feb 05, 2026

    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550

    • Land
    • 45.7 Acres
    • $5,470 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 0 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550
    • /76

      Est $841,087 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,830 Sq Ft

      1368 Mountainview Dr, Oakland, MD 21550

      1368 Mountainview Dr, Oakland, MD 21550
  • /65

    $599,900 Pending

    • 4 Beds
    • 3 Baths
    • 2,436 Sq Ft

    77 Meadow Ct, Oakland, MD 21550

    Lake Access Chalet at Deep Creek Lake – Featured on HGTV’s Lakefront Bargain Hunt, this property is quietly tucked away on over half an acre on rolling mountain pasture in the sought after Paradise Ridge community, and pairs rustic comfort with clean, modern lines. Warm wood tones, vaulted ceilings, and a two-story stone fireplace anchor the main level. Open kitchen and dining area flow into a

    Jon Bell Railey Realty, Inc.

    77 Meadow Ct, Oakland, MD 21550
  • /20

    $237,000 Sold Oct 30, 2025

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 660 Sq Ft
    • Built 1990

    Last Sold Summary

    • $359/SF
    • 19 Days On Market

    Current Estimated Value $244,266

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

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550
    • /63

      Est $651,952 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,200 Sq Ft

      265 Winding Trail Ln Unit 9A, Oakland, MD 21550

      265 Winding Trail Ln Unit 9A, Oakland, MD 21550
  • /45

    $1,329,000

    • 6 Beds
    • 4.5 Baths
    • 4,113 Sq Ft

    439 Paradise Heights, Oakland, MD 21550

    Stunning 6-Bedroom Kathadin Log Home with Breathtaking 180 views of Deep Creek Lake with Lake Access and a Boat Slip! This exceptional vacation home offers the perfect blend of rustic charm and modern luxury. Boasting 180-degree panoramic views of the sparkling lake, this property is a true mountain retreat. Every room is designed to capture the beauty of the surrounding landscape, with expansive

    Mike Kennedy Railey Realty, Inc.

    439 Paradise Heights, Oakland, MD 21550
  • /41

    $315,000 Sold Feb 14, 2025

    297 Paradise Point Rd, Oakland, MD 21550

    • 3 Beds
    • 4 Baths
    • 3,024 Sq Ft
    • Built 2005

    Last Sold Summary

    • $104/SF
    • 210 Days On Market

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    297 Paradise Point Rd, Oakland, MD 21550
    • /47

      Est $417,738 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,216 Sq Ft

      300 Big Rock Cabin Rd, Oakland, MD 21550

      300 Big Rock Cabin Rd, Oakland, MD 21550
  • /94

    $1,449,000

    • 5 Beds
    • 3 Baths
    • 2,826 Sq Ft

    336 Paradise Heights, Oakland, MD 21550

    Architecturally unique, private and spacious lakefront home with a perfect central location! Step into a home that blends striking architectural design with the best of lake living. The living room showcases a dramatic wall of glass and a floor-to-ceiling stone fireplace, while a large glass-walled rec room on the lower level offers another light-filled space to relax or entertain. This

    Susan Bell Railey Realty, Inc.

    336 Paradise Heights, Oakland, MD 21550
  • /23

    $119,000 Sold Jul 18, 2025

    1714 Mayhew Inn Rd, Oakland, MD 21550

    • Land
    • 7.5 Acres
    • $15,867 per Acre

    Last Sold Summary

    • 56 Days On Market

    Current Estimated Value $131,386

    Last Listing Agent Brian Homberg Taylor Made Deep Creek Vacations & Sales

    1714 Mayhew Inn Rd, Oakland, MD 21550
    • /50

      Est $605,263 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,086 Sq Ft

      208 Upper Penn Point Dr, Oakland, MD 21550

      208 Upper Penn Point Dr, Oakland, MD 21550
  • /68

    $575,000

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

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

    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 memorable Deep Creek Lake experience! The first level has a full kitchen with wine fridge and attached living room with an electric fireplace,

    Kevin Liller Railey Realty, Inc.

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
  • /44

    $589,000 Sold Sep 08, 2025

    939 Glendale Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,027 Sq Ft
    • Built 1995

    Last Sold Summary

    • $574/SF
    • 62 Days On Market

    Current Estimated Value $598,191

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    939 Glendale Rd, Oakland, MD 21550
    • /30

      Est $387,997 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,867 Sq Ft

      8081 Oakland Sang Run Rd, Oakland, MD 21550

      8081 Oakland Sang Run Rd, Oakland, MD 21550
  • /67

    $399,000

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

    5024 Cranesville Rd, Oakland, MD 21550

    Just Reduced!! Charming 3-Bedroom Home with Scenic Mountain & Valley Views. Nestled on a 1.68-acre hillside in a beautiful conservation area, 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.Inside, the main level features a spacious primary suite with a jetted tub, double vanity,

    Rich Orr Railey Realty, Inc.

    5024 Cranesville Rd, Oakland, MD 21550
  • /27

    $165,000 Sold Oct 30, 2025

    306 Shady Acre Ln, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,288 Sq Ft
    • Built 1972

    Last Sold Summary

    • $72/SF
    • 2 Days On Market

    Current Estimated Value $173,641

    Last Listing Agent Brody Monahan Lake Homes Realty, LLC

    306 Shady Acre Ln, Oakland, MD 21550
    • /32

      Est $433,326 Not Listed For Sale

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

      175 Whitetail Ct Unit 36, Oakland, MD 21550

      175 Whitetail Ct Unit 36, Oakland, MD 21550
  • /150

    $3,950,000

    • 6 Beds
    • 5.5 Baths
    • 4,354 Sq Ft

    282 McComas Beach Terrace, Oakland, MD 21550

    Discover The Birch Bower, a rare architect-designed lakefront sanctuary offering 600 feet of private shoreline on Deep Creek Lake. Completed in 2021, this 6-bedroom, 5.5-bath residence exemplifies modern luxury, combining meticulous design, serene natural surroundings, and proven short-term rental performance. Offered turn-key and fully furnished, this extraordinary lakefront estate presents a

    Morgan Boyer Hunt Country Sotheby's International Realty

    282 McComas Beach Terrace, Oakland, MD 21550
  • /5

    $34,500 Sold Jan 15, 2026

    62 Crosby Dr, Oakland, MD 21550

    • Land
    • 0.63 Acre
    • $54,762 per Acre

    Last Sold Summary

    • 73% Above List Price
    • 2,385 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Crosby Dr, Oakland, MD 21550

Showing Results 41 - 80, Page 2 of 18

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