12,296

Homes in ZIP Code 21550

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  • /53

    $1,500,000

    Sold Dec 01, 2025

    1674 Paradise Point Rd, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft
    • Built 1955

    Last Sold Summary

    • $641/SF
    • 465 Days On Market

    Current Estimated Value $1,471,256

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1674 Paradise Point Rd, Oakland, MD 21550
    • /33

      Est $579,242

      Not Listed For Sale

      939 Glendale Rd Unit 16, Oakland, MD 21550

      • 2 Beds
      • 2 Baths
      • Built 1993
      939 Glendale Rd Unit 16, Oakland, MD 21550

      Last Sold Summary

      • 12 Days On Market

  • /74

    $1,199,000

    • 5 Beds
    • 4.5 Baths
    • 4,191 Sq Ft

    454 Biltmore Ridge Trail, McHenry, MD 21541

    Welcome to 454 Biltmore Ridge - a stunning, recently built mountain retreat nestled in the heart of Deep Creek Lake. Perfectly positioned along hole 6 of Lodestone Golf Course, this exceptional 5-bedroom, 4.5 bath home offers the ideal combination of modern luxury, comfort and mountain charm. Designed with both relaxation and entertaining in mind, the open-concept main living area features a

    Sean Sober Taylor-Made Deep Creek Real Estate, LLC

    454 Biltmore Ridge Trail, McHenry, MD 21541
  • /64

    $695,000

    Sold Oct 09, 2025

    353 Basswood Way Unit 24, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,664 Sq Ft
    • Built 2005

    Last Sold Summary

    • $261/SF
    • 14 Days On Market

    Current Estimated Value $673,415

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    353 Basswood Way Unit 24, Oakland, MD 21550
    • /106

      Est $989,459

      Not Listed For Sale

      262 Penn Cove Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 2,700 Sq Ft
      • Built 1989
      262 Penn Cove Rd, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

  • /86

    $599,000

    • 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
  • /61

    $650,000

    Sold Aug 21, 2025

    1006 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 1,935 Sq Ft
    • Built 1993

    Last Sold Summary

    • $336/SF
    • 27 Days On Market

    Current Estimated Value $683,088

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1006 Lake Shore Dr, Oakland, MD 21550
    • /88

      Est $1,145,886

      Not Listed For Sale

      324 Penn Cove Rd, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 3,820 Sq Ft
      • Built 2004
      324 Penn Cove Rd, Oakland, MD 21550

      Last Sold Summary

      • 7 Days On Market

  • /16

    $675,000

    $259K PRICE DROP
    • Land
    • 212.15 Acres
    • $3,182 per Acre

    0 George Washington Hwy Unit MDGA2010274, Mount Lake Park, MD 21550

    Discover the perfect blend of nature and adventure with this remarkable 212-acre property, conveniently located with road frontage and an access point off Route 50. This unique offering consists of three different parcels: Tax ID 1208010161 (10.38 acres), Tax ID 1208007497 (39.05 acres), and Tax ID 1208007535 (162.72 acres). Whether you’re looking for a serene retreat, an outdoor enthusiast's

    Duane Stein II The KW Collective

    0 George Washington Hwy Unit MDGA2010274, Mount Lake Park, MD 21550
  • /48

    $279,000

    Sold Sep 25, 2025

    215 N 10th St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,518 Sq Ft
    • Built 1973

    Last Sold Summary

    • 3% Below List Price
    • $184/SF
    • 6 Days On Market

    Current Estimated Value $282,147

    Last Listing Agent ADAM MURRAY BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    215 N 10th St, Oakland, MD 21550
    • /100

      Est $503,478

      Not Listed For Sale

      545 Cumberland Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft
      • Built 2005
      545 Cumberland Rd, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /8

    $18,000

    $7K PRICE DROP
    • Land
    • 3 Acres
    • $6,000 per Acre

    0 Hoye St, Oakland, MD 21550

    Make an offer, buy it now +/- 2.96 Acre lot of land in Garrett County. Close to the West Virginias Border. Easy access to major traffic artery Seneca Trail Highway. Parcel is vacant. Deposit is $5,000

    Adam Shpritz

    0 Hoye St, Oakland, MD 21550
  • /22

    $25,000

    Sold Jun 27, 2025

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550

    • Land
    • 1.05 Acres
    • $23,810 per Acre

    Last Sold Summary

    • 84 Days On Market

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

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    • /48

      Est $382,288

      Not Listed For Sale

      3598 Lake Shore Dr, Oakland, MD 21550

      • 1 Bed
      • 1.5 Baths
      • 665 Sq Ft
      • Built 1948
      3598 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 64 Days On Market

  • /16

    $67,000

    • Land
    • 24,829 Sq Ft
    • $117,544 per Acre

    60 Sundance Way, McHenry, MD 21541

    Escape to the beauty and tranquility of Deep Creek Maryland! This beautiful lot offers the perfect opportunity to build your dream getaway or year-round home in one of Maryland's sought after destinations. Enjoy the peaceful surroundings while being just minutes from Deep Creek Lake, Wisp Ski resort, championship golf courses, state park with hiking and waterfalls, local restaurants, breweries

    Julie Hess Keller Williams of Central PA

    60 Sundance Way, McHenry, MD 21541
  • /2

    $205,000

    Sold May 20, 2026

    207 Shenandoah Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,492 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Above List Price
    • $137/SF
    • 6 Days On Market

    Current Estimated Value $193,540

    Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    207 Shenandoah Ave, Oakland, MD 21550
    • /87

      Est $1,168,111

      Not Listed For Sale

      3003 Lake Shore Dr, Oakland, MD 21550

      • 3 Beds
      • 4.5 Baths
      • 1,968 Sq Ft
      • Built 1940
      3003 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 104 Days On Market

  • /32

    $1,970,000

    Under Contract
    • 5 Beds
    • 4 Baths
    • 2,864 Sq Ft

    2119 Marsh Hill Rd, Mc Henry, MD 21541

    Welcome to “All Decked Out”—a stunning lakefront retreat offering the perfect blend of privacy, modern updates, and year-round adventure in the heart of Deep Creek Lake. Nestled on a beautifully wooded 1.3-acre lot along Marsh Hill Road, this 5-bedroom, 4-bath home boasts approximately 150 feet of private lake frontage and delivers the ultimate waterfront lifestyle.Thoughtfully updated

    Chad Ward Long & Foster Real Estate, Inc.

    2119 Marsh Hill Rd, Mc Henry, MD 21541
  • /40

    $615,000

    Sold Jul 07, 2025

    245 Santa fe Trail, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft
    • Built 2003

    Last Sold Summary

    • $270/SF
    • 51 Days On Market

    Current Estimated Value $598,839

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

    245 Santa fe Trail, Oakland, MD 21550
    • /92

      Est $2,614,635

      Not Listed For Sale

      2303 Lake Shore Dr, Oakland, MD 21550

      • 6 Beds
      • 4.5 Baths
      • 5,859 Sq Ft
      • Built 2001
      2303 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 84 Days On Market

  • /20

    $60,000

    • Land
    • 22,215 Sq Ft
    • $117,647 per Acre

    0 Whispering Pines Ln Unit MDGA2010384, 14, West Oakland, MD 21550

    Enjoy the privacy of this location, and build your dream "cabin in the woods" on this .51 acre lot, with the Youghiogheny River and Swallow Falls State Park so close by! This lot is approved for a sand mound system and has a 3-bedroom perc. DISCLOSURE: RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. PROSPECTIVE PURCHASERS AND THEIR AGENTS ASSUME ALL LIABILITY ON ENTERING THE

    Kathy Gibson Railey Realty, Inc.

    0 Whispering Pines Ln Unit MDGA2010384, 14, West Oakland, MD 21550
  • /79

    $910,000

    Sold Sep 25, 2025

    2045 Swallow Falls Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 5,416 Sq Ft
    • Built 2023

    Last Sold Summary

    • $168/SF
    • 82 Days On Market

    Current Estimated Value $909,300

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

    2045 Swallow Falls Rd, Oakland, MD 21550
    • /60

      Est $532,692

      Not Listed For Sale

      568 Skippers Point Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1981
      568 Skippers Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 9 Days On Market

  • /64

    $1,400,000

    • 5 Beds
    • 3.5 Baths
    • 2,832 Sq Ft

    827 Penn Point Rd, Oakland, MD 21550

    Custom built by the original owners and thoughtfully expanded with a recent addition, this exceptional five-bedroom, 3.5-bath home is set on 100 feet of split lakefront in desirable Penn Cove. Featuring a coveted Type A dock permit, lakeside fire pit and pavilion, and easy shoreline access, the property is designed to embrace lake living in every season. Set on a generously sized lot with

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

    827 Penn Point Rd, Oakland, MD 21550
  • /43

    $587,500

    Sold Aug 22, 2025

    307 Winding Trail Ln Unit 12B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2019

    Last Sold Summary

    • $178/SF
    • 9 Days On Market

    Current Estimated Value $568,890

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    307 Winding Trail Ln Unit 12B, Oakland, MD 21550
    • /82

      Est $1,830,637

      Not Listed For Sale

      228 Paradise Heights, Oakland, MD 21550

      • 4 Beds
      • 4.5 Baths
      • 2,249 Sq Ft
      • Built 1989
      228 Paradise Heights, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /82

    $760,000

    $105K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 2,970 Sq Ft

    1909 Pysell Crosscut Rd, Oakland, MD 21550

    Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just minutes from Deep Creek Lake and Oakland. This 4-bedroom, 4.5-bath home has been carefully updated to balance comfort, practicality, and modern style. The main level features hardwood floors, radiant heat for added comfort, and open gathering spaces with quiet nooks for reading or hobbies. Upstairs, two

    Melissa Long Railey Realty, Inc.

    1909 Pysell Crosscut Rd, Oakland, MD 21550
  • /94

    $1,340,000

    Sold Apr 08, 2026

    336 Paradise Heights, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,826 Sq Ft
    • Built 1997

    Last Sold Summary

    • $474/SF
    • 159 Days On Market

    Current Estimated Value $1,370,882

    Last Listing Agent Susan Bell Railey Realty, Inc.

    336 Paradise Heights, Oakland, MD 21550
    • /63

      Est $524,929

      Not Listed For Sale

      26 Paradise Ridge Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,104 Sq Ft
      • Built 1975
      26 Paradise Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 178 Days On Market

  • /60

    $174,900

    • 3 Beds
    • 1 Bath
    • 816 Sq Ft

    63 Wallman Rd, Oakland, MD 21550

    Remodeled Rancher Near the North Branch Potomac RiverThis charming 3-bedroom, 1-bath rancher has been completely remodeled, with all new appliances. Located within walking distance of the scenic North Branch of the Potomac River, the home offers both convenience and natural beauty at your doorstep.A recently enclosed front porch with a wood stove provides extra warmth and a welcoming spot

    Rich Orr Railey Realty, Inc.

    63 Wallman Rd, Oakland, MD 21550
  • /15

    $87,000

    Sold Feb 06, 2026

    Lot 69 Sundance Way, Mc Henry, MD 21541

    • Land
    • 30,056 Sq Ft
    • $126,087 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 588 Days On Market

    Last Listing Agent Kellyann Green Railey Realty, Inc.

    Lot 69 Sundance Way, Mc Henry, MD 21541
    • /30

      Est $1,127,938

      Not Listed For Sale

      187 Lower Penn Point Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • Built 1950
      187 Lower Penn Point Dr, Oakland, MD 21550

      Last Sold Summary

      • 80 Days On Market

  • /9

    $3,500

    • Land
    • 20,908 Sq Ft
    • $7,292 per Acre

    LOT 2 Beaver Run Rd, Oakland, MD 21550

    Tucked away in the stunning mountains of Western Maryland, this unbuildable lot provides a serene escape into nature, offering breathtaking views throughout the community, as well as an abundance wildlife. Located in the Youghiogheny Mountain Resort, this membership-only lot grants exclusive access to over 50 miles of private roads and trails, ideal for ATV and side-by-side adventures. Resort

    Elizabeth Broadwater Taylor-Made Deep Creek Real Estate, LLC

    LOT 2 Beaver Run Rd, Oakland, MD 21550
  • /10

    $300,000

    Sold May 06, 2026

    4000 Area Broadford Rd, Oakland, MD 21550

    • Land
    • 56.5 Acres
    • $5,310 per Acre

    Last Sold Summary

    • 0 Days On Market

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

    4000 Area Broadford Rd, Oakland, MD 21550
    • /35

      Est $1,470,198

      Not Listed For Sale

      156 Sunrise Point Ln, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft
      • Built 1950
      156 Sunrise Point Ln, Oakland, MD 21550

      Last Sold Summary

      • 38 Days On Market

  • /77

    $899,000

    $31K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 2,464 Sq Ft

    62 Whispering Pines Ln, Oakland, MD 21550

    Tucked away on just over 7 acres of serene, wooded privacy, this stunning custom Yellowstone log home offers the perfect blend of rustic charm and modern comfort—just minutes from Swallow Falls State Park and only 10 minutes to Deep Creek Lake and Wisp Resort. The inviting open main level is designed for effortless entertaining, highlighted by a warm gas fireplace in the family room, a spacious

    Justin Liller Railey Realty, Inc.

    62 Whispering Pines Ln, Oakland, MD 21550
  • /43

    $290,000

    Sold Jun 01, 2026

    3749 Maryland Hwy, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 2,015 Sq Ft
    • Built 1982

    Last Sold Summary

    • 11% Below List Price
    • $144/SF
    • 63 Days On Market

    Current Estimated Value $296,959

    Last Listing Agent Jovan Vidulovic Keller Williams Realty

    3749 Maryland Hwy, Oakland, MD 21550
    • /48

      Est $739,025

      Not Listed For Sale

      91 Mallard Loop, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 4,508 Sq Ft
      • Built 1997
      91 Mallard Loop, Oakland, MD 21550

      Last Sold Summary

      • 45 Days On Market

  • /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 Real Estate, LLC

    25 Silver Tree Ln, Oakland, MD 21550
  • /36

    $829,000

    Sold May 22, 2026

    34 Hooppole Ct, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,355 Sq Ft
    • Built 1975

    Last Sold Summary

    • $612/SF
    • 0 Days On Market

    Current Estimated Value $817,945

    Last Listing Agent Rich Orr Railey Realty, Inc.

    34 Hooppole Ct, Oakland, MD 21550

Showing Results 641 - 680, Page 17 of 18

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