10,714

Oakland, MD Homes

Section Image
    • 208 Upper Penn Point Dr, Oakland, MD 21550
      208 Upper Penn Point Dr, Oakland, MD 21550
      208 Upper Penn Point Dr, Oakland, MD 21550
      /50

      Est $635,024 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
  • 16 Lemley Dr, Oakland, MD 21550
    16 Lemley Dr, Oakland, MD 21550
    16 Lemley Dr, Oakland, MD 21550
    /62

    $399,000

    • 4 Beds
    • 2.5 Baths
    • 1,104 Sq Ft

    16 Lemley Dr, Oakland, MD 21550

    Nestled in the serene community of Roman Nose Spa at Deep Creek Lake, this charming contemporary home offers a perfect blend of comfort and style and makes a great basecamp. With 4 beds and 2 1/2 baths and a thoughtfully designed living space, ideal for both relaxation and entertaining. Enjoy breathtaking views of Deep Creek Lake and the surrounding mountains from your backyard, where outdoor

    Andrew Eiswert Railey Realty, Inc.

    16 Lemley Dr, Oakland, MD 21550
  • 9.3 +/- Acres Upperman Rd, Oakland, MD 21550
    9.3 +/- Acres Upperman Rd, Oakland, MD 21550
    9.3 +/- Acres Upperman Rd, Oakland, MD 21550
    /4

    $140,000 Sold Mar 17, 2025

    9.3 +/- Acres Upperman Rd, Oakland, MD 21550

    • Land
    • 9.2 Acres
    • $15,217 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    9.3 +/- Acres Upperman Rd, Oakland, MD 21550
    • 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 $388,757 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
  • 439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, 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
  • 158 Silver Tree Ln, Oakland, MD 21550
    158 Silver Tree Ln, Oakland, MD 21550
    158 Silver Tree Ln, Oakland, MD 21550
    /49

    $790,000 Sold May 09, 2025

    158 Silver Tree Ln, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,250 Sq Ft
    • Built 2003

    Last Sold Summary

    • $351/SF
    • 79 Days On Market

    Current Estimated Value $839,144

    Last Listing Agent Jon Bell Railey Realty, Inc.

    158 Silver Tree Ln, Oakland, MD 21550
    • 175 Whitetail Ct Unit 36, Oakland, MD 21550
      175 Whitetail Ct Unit 36, Oakland, MD 21550
      175 Whitetail Ct Unit 36, Oakland, MD 21550
      /32

      Est $427,500 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
  • 3084 Lake Shore Dr, Oakland, MD 21550
    3084 Lake Shore Dr, Oakland, MD 21550
    3084 Lake Shore Dr, Oakland, MD 21550
    /71

    $599,900 Pending

    • 4 Beds
    • 3 Baths
    • 2,464 Sq Ft

    3084 Lake Shore Dr, Oakland, MD 21550

    Cozy Retreat on Lake Shore Drive! This 4-bed, 3-bath cottage was built for relaxation, entertainment, and making memories. The open-concept living area keeps everyone connected, while the expansive deck and hot tub allow you to take the fun outside. Upstairs, the primary suite steals the show! A personal fireplace with a wall of glass to let in the light and soak in the views. Three more bedrooms

    Jon Bell Railey Realty, Inc.

    3084 Lake Shore Dr, Oakland, MD 21550
  • 20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    /39

    $450,000 Sold Nov 10, 2025

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Built 1972

    Last Sold Summary

    • $340/SF
    • 179 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    • 6 Cedar Ln, Oakland, MD 21550
      6 Cedar Ln, Oakland, MD 21550
      6 Cedar Ln, Oakland, MD 21550
      /12

      Est $94,780 Not Listed For Sale

      6 Cedar Ln, Oakland, MD 21550

      6 Cedar Ln, Oakland, MD 21550
  • 336 Paradise Heights, Oakland, MD 21550
    336 Paradise Heights, Oakland, MD 21550
    336 Paradise Heights, Oakland, MD 21550
    /94

    $1,499,000

    • 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
  • 0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550
    0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550
    0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550
    /16

    $100,000 Sold May 02, 2025

    0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550

    • Land
    • 2.4 Acres
    • $41,667 per Acre

    Last Sold Summary

    • 433 Days On Market

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

    0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550
    • 0 Overlook Dr, Oakland, MD 21550
      0 Overlook Dr, Oakland, MD 21550
      0 Overlook Dr, Oakland, MD 21550
      /13

      Not Listed For Sale

      0 Overlook Dr, Oakland, MD 21550

      0 Overlook Dr, Oakland, MD 21550
  • 25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    /52

    $749,900

    • 5 Beds
    • 4 Baths
    • 2,364 Sq Ft

    25 Silver Tree Ln, Oakland, MD 21550

    Beautiful lake access retreat located in the Silver Tree Landings community with an available home warranty. This recently updated contemporary home feels warm and inviting from the moment you walk in (upgrade list available). Offering hardwood flooring, granite countertops, two stone propane fireplaces and cathedral ceilings. The abundance of windows allows the natural light to brighten any

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    25 Silver Tree Ln, Oakland, MD 21550
  • 15 D St, Oakland, MD 21550
    15 D St, Oakland, MD 21550
    15 D St, Oakland, MD 21550
    /44

    $140,000 Sold Jul 08, 2025

    15 D St, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 1,680 Sq Ft
    • Built 1953

    Last Sold Summary

    • $83/SF
    • 86 Days On Market

    Current Estimated Value $155,222

    Last Listing Agent Jon Bell Railey Realty, Inc.

    15 D St, Oakland, MD 21550
    • 1506 Broadford Rd, Oakland, MD 21550
      1506 Broadford Rd, Oakland, MD 21550
      1506 Broadford Rd, Oakland, MD 21550
      /98

      Est $488,293 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,048 Sq Ft

      1506 Broadford Rd, Oakland, MD 21550

      1506 Broadford Rd, Oakland, MD 21550
  • 19956 Garrett Hwy Unit 6, Oakland, MD 21550
    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    /81

    $1,289,000 Under Contract

    • 4 Beds
    • 4 Baths
    • 3,000 Sq Ft

    19956 Garrett Hwy Unit 6, Oakland, MD 21550

    Experience the best in maintenance free lakefront living on Deep Creek Lake! This 4 BR 4 Bath lakefront townhome with assigned dock slip is located within walking distance of many of the lake's best restaurants and attractions. The open floor plan offers a main level great room and lower level family/game room. The large kitchen offers a lake facing island with breakfast bar. Three private suites

    Bill Weissgerber Railey Realty, Inc.

    19956 Garrett Hwy Unit 6, Oakland, MD 21550
  • 58 Glendale Woods Rd, Oakland, MD 21550
    58 Glendale Woods Rd, Oakland, MD 21550
    58 Glendale Woods Rd, Oakland, MD 21550
    /63

    $711,000 Sold Oct 15, 2025

    58 Glendale Woods Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,556 Sq Ft
    • Built 2006

    Last Sold Summary

    • $278/SF
    • 5 Days On Market

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    58 Glendale Woods Rd, Oakland, MD 21550
    • 812 Winter Place, Oakland, MD 21550
      812 Winter Place, Oakland, MD 21550
      812 Winter Place, Oakland, MD 21550
      /4

      Est $40,262 Not Listed For Sale

      812 Winter Place, Oakland, MD 21550

      812 Winter Place, Oakland, MD 21550
  • 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

    • 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
  • 0 Coolidge Ave, Oakland, MD 21550
    0 Coolidge Ave, Oakland, MD 21550
    0 Coolidge Ave, Oakland, MD 21550
    /14

    $80,000 Sold Sep 26, 2025

    0 Coolidge Ave, Oakland, MD 21550

    • Land
    • 0.46 Acre
    • $173,913 per Acre

    Last Sold Summary

    • 76 Days On Market

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

    0 Coolidge Ave, Oakland, MD 21550
    • 2 Cedar Ln, Oakland, MD 21550
      2 Cedar Ln, Oakland, MD 21550
      2 Cedar Ln, Oakland, MD 21550
      /12

      Not Listed For Sale

      2 Cedar Ln, Oakland, MD 21550

      2 Cedar Ln, Oakland, MD 21550
  • 5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    /67

    $475,000

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

    5024 Cranesville Rd, Oakland, MD 21550

    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, and shower, a

    Rich Orr Railey Realty, Inc.

    5024 Cranesville Rd, Oakland, MD 21550
  • 45 Village Dr Unit 4, Oakland, MD 21550
    45 Village Dr Unit 4, Oakland, MD 21550
    45 Village Dr Unit 4, Oakland, MD 21550
    /35

    $405,000 Sold Dec 22, 2025

    45 Village Dr Unit 4, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,096 Sq Ft
    • Built 2004

    Last Sold Summary

    • $370/SF
    • 173 Days On Market

    Last Listing Agent Ana Dubin RE/MAX Realty Group

    45 Village Dr Unit 4, 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
  • 282 McComas Beach Terrace, Oakland, MD 21550
    282 McComas Beach Terrace, Oakland, MD 21550
    282 McComas Beach Terrace, Oakland, MD 21550
    /150

    $4,200,000 New Construction

    • 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
  • 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

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Vacations & Sales

    135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    • 94 Lehman Ln Unit 31, Oakland, MD 21550
      94 Lehman Ln Unit 31, Oakland, MD 21550
      94 Lehman Ln Unit 31, Oakland, MD 21550
      /39

      Est $696,068 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,340 Sq Ft

      94 Lehman Ln Unit 31, Oakland, MD 21550

      94 Lehman Ln Unit 31, Oakland, MD 21550
  • 2 Overlook Ridge Dr S, Oakland, MD 21550
    2 Overlook Ridge Dr S, Oakland, MD 21550
    2 Overlook Ridge Dr S, Oakland, MD 21550
    /11

    $199,900

    • Land
    • 0.11 Acre
    • $1,817,273 per Acre

    2 Overlook Ridge Dr S, Oakland, MD 21550

    Enjoy the best the lake has to offer from 'Overlook Ridge'! Boasting year-round lake views, yet tucked away in a peaceful and serene community setting. Short drive to the community lake access area for swimming and fishing! Dock Slips may be leased through HOA. Utilities to site and ready to build your perfect four-season Deep Creek getaway. Located just off of Rt. 219, with easy access to all

    Jon Bell Railey Realty, Inc.

    2 Overlook Ridge Dr S, Oakland, MD 21550
  • Lots 22 & 23 Black Oak Ln, Oakland, MD 21550
    Lots 22 & 23 Black Oak Ln, Oakland, MD 21550
    /2

    $20,000 Sold Jun 26, 2025

    Lots 22 & 23 Black Oak Ln, Oakland, MD 21550

    • Land
    • 0.47 Acre
    • $42,553 per Acre

    Last Sold Summary

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

    Lots 22 & 23 Black Oak Ln, 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 $537,880 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,260 Sq Ft

      189 Maple Del Ln, Oakland, MD 21550

      189 Maple Del Ln, Oakland, MD 21550
  • 41 Boyd Paugh Ln, Oakland, MD 21550
    41 Boyd Paugh Ln, Oakland, MD 21550
    41 Boyd Paugh Ln, Oakland, MD 21550
    /103

    $2,399,000 Pre-Foreclosure

    • 7 Beds
    • 5 Baths
    • 4,691 Sq Ft

    41 Boyd Paugh Ln, Oakland, MD 21550

    Gorgeous 7 bedroom home with dock slip! This newer construction home sits on a quiet corner of Deep Creek Lake with 200 feet of lake frontage. Located in the beautiful and quiet Heron Cove community and comes with two community lake access points, one with a sandy beach area, tennis courts, and walking trails. The level lot is surrounded by trees and designed for privacy and outdoor enjoyment,

    Rachel Bruch Railey Realty, Inc.

    41 Boyd Paugh Ln, Oakland, MD 21550
  • 81 Timber Ln, Oakland, MD 21550
    81 Timber Ln, Oakland, MD 21550
    81 Timber Ln, Oakland, MD 21550
    /20

    $80,000 Sold Jun 30, 2025

    81 Timber Ln, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 1,860 Sq Ft
    • Built 1965

    Last Sold Summary

    • $43/SF
    • 5 Days On Market

    Current Estimated Value $90,598

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    81 Timber Ln, 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

      • 4 Beds
      • 3 Baths
      • 2,784 Sq Ft

      319 Basswood Way Unit LOT 21, Oakland, MD 21550

      319 Basswood Way Unit LOT 21, Oakland, MD 21550
  • 3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    /31

    $1,800,000

    • 4 Beds
    • 6 Baths
    • 5,117 Sq Ft

    3898 Underwood Rd, Oakland, MD 21550

    One of a kind 4 BR 4 BA brick Home. 5,100 sq. ft. + 3 car garage. Situated on 23.47 elevated acres with unbelievable panoramic views of Pleasant Valley and surrounding farming community. Living area on one level with full unfinished basement. Views from every room. Massive amount of closet space The opportunities are abundant with this property.

    Robert Custer Custer Realty & Auction

    3898 Underwood Rd, Oakland, MD 21550
  • 3821 Underwood Rd, Oakland, MD 21550
    3821 Underwood Rd, Oakland, MD 21550
    3821 Underwood Rd, Oakland, MD 21550
    /21

    $155,000 Sold May 22, 2025

    3821 Underwood Rd, Oakland, MD 21550

    • 4 Beds
    • 1 Bath
    • 1,232 Sq Ft
    • Built 1964

    Last Sold Summary

    • $126/SF
    • 10 Days On Market

    Current Estimated Value $158,903

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    3821 Underwood Rd, 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 $608,404 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,454 Sq Ft

      48 Skippers Estates Dr, Oakland, MD 21550

      48 Skippers Estates Dr, Oakland, MD 21550
  • 697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    /56

    $339,000

    • 5 Beds
    • 3.5 Baths
    • 3,682 Sq Ft

    697 Monte Vista Rd, Oakland, MD 21550

    Tucked away just minutes from downtown Oakland, MD, lies a home that truly surprises with over 3,500 sq. ft. of living space on 1.88 acres with breathtaking farm and mountain views. Step inside the main level, where the master suite awaits along with two additional large bedrooms and a full bath, plus a mudroom area with a convenient half bath—perfect for entertaining. Cozy evenings are made even

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    697 Monte Vista 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

    $855,000 Sold Mar 13, 2025

    33 Black Bear Ct, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,976 Sq Ft
    • Built 1989

    Last Sold Summary

    • $287/SF
    • 88 Days On Market

    Current Estimated Value $888,304

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    33 Black Bear Ct, Oakland, MD 21550
    • 36 Cherokee Ln, Oakland, MD 21550
      36 Cherokee Ln, Oakland, MD 21550
      36 Cherokee Ln, Oakland, MD 21550
      /62

      Est $208,309 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 864 Sq Ft

      36 Cherokee Ln, Oakland, MD 21550

      36 Cherokee Ln, Oakland, MD 21550

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