12,296

Homes in ZIP Code 21550

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  • /33

    $130,000

    Sold May 22, 2026

    565 Glendale Rd Unit 210-A, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 382 Sq Ft
    • Built 2006

    Last Sold Summary

    • 26% Below List Price
    • $340/SF
    • 225 Days On Market

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

    565 Glendale Rd Unit 210-A, Oakland, MD 21550
    • /48

      Est $459,850

      Not Listed For Sale

      482 Pergin Farm Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 2,160 Sq Ft
      • Built 1980
      482 Pergin Farm Rd, Oakland, MD 21550

      Last Sold Summary

      • 128 Days On Market

  • /64

    $1,225,000

    $50K PRICE DROP
    • 6 Beds
    • 6.5 Baths
    • 3,384 Sq Ft

    36 Irwin Way, McHenry, MD 21541

    Welcome to All The Time, a beautifully crafted mountain retreat in the heart of Deep Creek Lake and right along Lodestone Golf Course. Blending modern comfort with rustic charm, this inviting getaway is designed for unforgettable moments with family and friends. Inside, the bright open-concept living area features a cozy fireplace and plenty of space to gather after a day of adventure. The fully

    Nina Beitzel Railey Realty, Inc.

    36 Irwin Way, McHenry, MD 21541
  • /53

    $682,567

    Sold Oct 31, 2025

    183 Kendall Camp Cir, McHenry, MD 21541

    • 4 Beds
    • 3 Baths
    • 2,135 Sq Ft
    • Built 2008

    Last Sold Summary

    • $320/SF
    • 173 Days On Market

    Current Estimated Value $704,167

    Last Listing Agent Jon Bell Railey Realty, Inc.

    183 Kendall Camp Cir, McHenry, MD 21541
    • /46

      Est $1,442,381

      Not Listed For Sale

      2127 Lake Shore Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,546 Sq Ft
      • Built 1960
      2127 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 20 Days On Market

  • /12

    $45,000

    • Land
    • 14,810 Sq Ft
    • $132,353 per Acre

    LOT 181 Santa fe Trail, Oakland, MD 21550

    Don't miss the opportunity to own a lake area lot near the one and only Deep Creek Lake. 0.34 acre wooded lot, close to multiple local attractions. Call today! Verify utilities with Garrett County Environmental Department. Being sold subject to successful perc.

    Amy Skipper Railey Realty, Inc.

    LOT 181 Santa fe Trail, Oakland, MD 21550
  • /38

    $100,000

    Sold Jul 11, 2025

    5914 Maryland Hwy, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,775 Sq Ft
    • Built 1973

    Last Sold Summary

    • $56/SF
    • 4 Days On Market

    Current Estimated Value $177,437

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

    5914 Maryland Hwy, Oakland, MD 21550
    • /97

      Est $2,339,389

      Not Listed For Sale

      1738 Paradise Point Rd, Oakland, MD 21550

      • 7 Beds
      • 5.5 Baths
      • 4,260 Sq Ft
      • Built 2002
      1738 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 127 Days On Market

  • /55

    $359,000

    $20K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,388 Sq Ft

    215 H St, Oakland, MD 21550

    Welcome to the Maggie Watson Cottage, where historic charm meets modern convenience in the heart of Mountain Lake Park. This beautifully renovated home offers 3 bedrooms and 3 full bathrooms, thoughtfully updated to provide today’s comforts while preserving its timeless character. The interior features updated paint, both refinished and brand new hardwood flooring, and a modern gourmet kitchen

    Rachel Bruch Railey Realty, Inc.

    215 H St, Oakland, MD 21550
  • /46

    $1,120,000

    Sold Jul 08, 2025

    636 Paradise Heights, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,028 Sq Ft
    • Built 1986

    Last Sold Summary

    • $552/SF
    • 11 Days On Market

    Current Estimated Value $1,102,947

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    636 Paradise Heights, Oakland, MD 21550
    • /78

      Est $219,813

      Not Listed For Sale

      1400 Oakland Ave, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 1972
      1400 Oakland Ave, Oakland, MD 21550

      Last Sold Summary

      • 8 Days On Market

  • /26

    $129,000

    Pending
    • Land
    • 24,829 Sq Ft
    • $226,316 per Acre

    Lot 47 Mountaintop Rd, McHenry, MD 21550

    Build your dream mountain retreat in the prestigious Deep Creek Highlands! This prime building lot is ideally situated next to a serene association common area, offering added privacy and natural beauty. Distinctive rock outcroppings on the property create the perfect canvas for a truly unique architectural design that blends seamlessly with the landscape. Enjoy all the community amenities

    Larry Smith Railey Realty, Inc.

    Lot 47 Mountaintop Rd, McHenry, MD 21550
  • /22

    $180,000

    Sold Sep 12, 2025

    4643 Oakland Sang Run Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 1979

    Last Sold Summary

    • $208/SF
    • 4 Days On Market

    Current Estimated Value $192,898

    Last Listing Agent Jon Bell Railey Realty, Inc.

    4643 Oakland Sang Run Rd, Oakland, MD 21550
    • /69

      Est $459,365

      Not Listed For Sale

      1014 Madison St, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 3,016 Sq Ft
      • Built 1988
      1014 Madison St, Oakland, MD 21550

      Last Sold Summary

      • 21 Days On Market

  • /4

    $29,900

    • Land
    • 1.09 Acres
    • $27,431 per Acre

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550

    1+ acre building lot. Fairly leveled cleared lot with some distant mountain views. Paved County road frontage with private road/drive access to lot. Approved for private septic and well. Electric on-site. Located approx. 10+ mins from Deep Creek Lake and approx. less than 5 minutes from Oakland. Located within small 8 lot development, "The Homestead".

    Chip Smith 1 Real Estate Source LLC

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
  • /45

    $750,000

    Sold Jan 16, 2026

    198 Grandview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,744 Sq Ft
    • Built 2003

    Last Sold Summary

    • $273/SF
    • 150 Days On Market

    Current Estimated Value $778,838

    Last Listing Agent Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, MD 21550
    • /24

      Est $705,538

      Not Listed For Sale

      8 Arrowhead Ln, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • Built 1988
      8 Arrowhead Ln, Oakland, MD 21550

      Last Sold Summary

      • 80 Days On Market

  • /80

    $950,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,219 Sq Ft

    208 Cliff Dr, Oakland, MD 21550

    Picture perfect, private and wooded mountain retreat featuring lake access in a prime location close to all area amenities! Seasonal lake views! This highly desirable property offers the opportunity to walk to your dock featuring TWO slips for your use. A two-minute walk at the end of the quiet road leads you to the property's deeded lake-front land and two dock slips. Nestled among the

    Kellyann Green Railey Realty, Inc.

    208 Cliff Dr, Oakland, MD 21550
  • /12

    $75,000

    Sold Jul 10, 2025

    Lot 42 Winding Estates Dr, Mc Henry, MD 21550

    • Land
    • 1.1 Acres
    • $68,182 per Acre

    Last Sold Summary

    • 7 Days On Market

    Last Listing Agent Lucas Muenchow Railey Realty, Inc.

    Lot 42 Winding Estates Dr, Mc Henry, MD 21550
    • /88

      Est $450,573

      Not Listed For Sale

      189 Whistle Pig Way, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,777 Sq Ft
      • Built 1998
      189 Whistle Pig Way, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • /53

    $339,999

    $19K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 990 Sq Ft

    931 Black Oak Dr, Oakland, MD 21550

    Very motivated sellers!!!Escape to Your Profitable Mountain Sanctuary: The Yough Mountain CabinUnveiling the Ultimate Turnkey Retreat & High-Performing InvestmentNestled in the breathtaking heart of the exclusive Yough Mountain Resort, this stunning 3-bedroom cabin offers the perfect harmony of rustic soul and modern investment savvy. Whether you are looking for a private family getaway

    ANGELA BOSLEY Taylor-Made Deep Creek Real Estate, LLC

    931 Black Oak Dr, Oakland, MD 21550
  • /48

    $250,000

    Sold Jun 11, 2026

    18 Ollie North Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,956 Sq Ft
    • Built 1975

    Last Sold Summary

    • 13% Below List Price
    • $128/SF
    • 31 Days On Market

    Current Estimated Value $270,053

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    18 Ollie North Rd, Oakland, MD 21550
    • /80

      Est $1,463,854

      Not Listed For Sale

      2236 Paradise Point Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,004 Sq Ft
      • Built 1956
      2236 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • /8

    $17,000

    Pending
    • Land
    • 33,541 Sq Ft
    • $22,078 per Acre

    Lot 40 W Big Piney Dr, Oakland, MD 21550

    Located in the Youghiogheny Mountain Resort community, this .77ac lot offers the ultimate gateway to peaceful surroundings, beautiful views, and abundant wildlife. Approved for a sand mound sewage system, this lot provides the perfect opportunity to build your future outdoor enthusiast retreat! Enjoy exclusive access to over 50 miles of private roads and trails perfect for ATV and side-by-side

    Elizabeth Broadwater Taylor-Made Deep Creek Real Estate, LLC

    Lot 40 W Big Piney Dr, Oakland, MD 21550
  • /65

    $558,000

    Sold Nov 10, 2025

    72 Cliff Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft
    • Built 1988

    Last Sold Summary

    • $256/SF
    • 32 Days On Market

    Current Estimated Value $558,613

    Last Listing Agent Larry Smith Railey Realty, Inc.

    72 Cliff Dr, Oakland, MD 21550
    • /27

      Not Listed For Sale

      128 Shaffer Ln, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,040 Sq Ft
      • Built 2001
      128 Shaffer Ln, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • /64

    $769,900

    $30K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,780 Sq Ft

    467 Paradise Ridge Rd, Oakland, MD 21550

    Panoramic mountain and lake views set the tone at this lake access home in Paradise Ridge, one of Deep Creek’s most sought-after communities! Perched at the top of the hill on 1.29 acres, this 4-bedroom, 3 full and 1 half bath retreat offers 3,780 finished square feet across three levels. Abundant glass frames the surrounding ridgelines with views of Deep Creek Lake from every room in the house!

    Jon Bell Railey Realty, Inc.

    467 Paradise Ridge Rd, Oakland, MD 21550
  • /65

    $379,000

    Sold Oct 08, 2025

    113 G St, Oakland, MD 21550

    • 9 Beds
    • 3.5 Baths
    • 3,840 Sq Ft
    • Built 1903

    Last Sold Summary

    • $99/SF
    • 40 Days On Market

    Current Estimated Value $384,572

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

    113 G St, Oakland, MD 21550
    • /49

      Est $1,190,331

      Not Listed For Sale

      215 Lower Penn Point Dr, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 2,580 Sq Ft
      • Built 2001
      215 Lower Penn Point Dr, Oakland, MD 21550

      Last Sold Summary

      • 51 Days On Market

  • /11

    $122,500

    • Land
    • 13.57 Acres
    • $9,027 per Acre

    Lot 3 Deer Run Rd, 14, West Oakland, MD 21550

    Rare Opportunity in Youghiogheny Mountain Resort – 13.57 Acres on Deer Run Road This is a unique chance to own a substantial 13.57-acre parcel in Youghiogheny Mountain Resort (YMR), a private, gated community where most lots have already been subdivided into much smaller parcels. Whether you're seeking privacy, recreation, or a place to build your dream home or cabin, Lot 3 on Deer Run Road

    Thomas Long Railey Realty, Inc.

    Lot 3 Deer Run Rd, 14, West Oakland, MD 21550
  • /31

    $189,000

    Sold Jul 24, 2025

    1681 Shady Dell Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1985

    Last Sold Summary

    • $197/SF
    • 2 Days On Market

    Current Estimated Value $181,188

    Last Listing Agent Tim Macauley Taylor-Made Deep Creek Real Estate, LLC

    1681 Shady Dell Rd, Oakland, MD 21550
    • /74

      Est $170,135

      Not Listed For Sale

      400 E St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,880 Sq Ft
      • Built 1900
      400 E St, Oakland, MD 21550

      Last Sold Summary

      • 98 Days On Market

  • /113

    $715,000

    Pending
    • 4 Beds
    • 5 Baths
    • 3,240 Sq Ft

    250 Lehman Ln Unit 39, Oakland, MD 21550

    Immaculate 4-bedroom log home in the highly sought after Gallatin Woods community. Custom built with custom finishes throughout. Granite counters, hardwood floors, 2 fireplaces, extensive hardscaped patio and outdoor fireplace, and the list of upgrades literally goes on and is available on request for the discerning buyer. Minutes from Deep Creek Lake and all of the area amenities yet tucked away

    Richard Candy Synergy Realty

    250 Lehman Ln Unit 39, Oakland, MD 21550
  • /6

    $30,000

    Sold Oct 23, 2025

    28 Wild Turkey Ln, Oakland, MD 21550

    • Land
    • 1 Acre
    • $30,000 per Acre

    Last Sold Summary

    • 14 Days On Market

    Last Listing Agent Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    28 Wild Turkey Ln, Oakland, MD 21550
    • /32

      Est $312,755

      Not Listed For Sale

      67 Fireside Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1998
      67 Fireside Rd, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • /30

    $249,000

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,390 Sq Ft

    62 Wild Turkey Ct, Oakland, MD 21550

    Current new home construction project underway, but Builder not going to complete at this time due too busy. So, ready for who may wish to complete project themselves or have completed by others, or current Builder may consider completing for Buyer. Current structure is a custom engineered modular home. This is not a completed or intended by Builder to be completed house project at this time .

    Chip Smith 1 Real Estate Source LLC

    62 Wild Turkey Ct, Oakland, MD 21550
  • /62

    $349,900

    Sold May 08, 2026

    16 Lemley Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 1,104 Sq Ft
    • Built 1974

    Last Sold Summary

    • $317/SF
    • 128 Days On Market

    Current Estimated Value $373,339

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    16 Lemley Dr, Oakland, MD 21550
    • /26

      Est $1,281,514

      Not Listed For Sale

      464 Lake Forest Dr, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 2,496 Sq Ft
      • Built 1997
      464 Lake Forest Dr, Oakland, MD 21550

      Last Sold Summary

      • 277 Days On Market

  • /35

    $130,000

    • Land
    • 22,215 Sq Ft
    • $254,902 per Acre

    0 Highline Dr Unit MDGA2006792, Mc Henry, MD 21541

    Happy New Year with a price adjustment on this mountaintop lot in the Highline community! If you love the mountains, the lake, snow and golf-take a look at this location and bring your home plans that will take advantage of all these beautiful aspects of Garrett County! Natural wooded landscapes surround you. It is an easy walk along the community's slope access trail to the Main Street slopes.

    Kathy Gibson Railey Realty, Inc.

    0 Highline Dr Unit MDGA2006792, Mc Henry, MD 21541
  • /34

    $275,000

    Sold Jan 02, 2026

    34 Laurel Brook Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1992

    Last Sold Summary

    • 13 Days On Market

    Current Estimated Value $309,765

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

    34 Laurel Brook Dr, Oakland, MD 21550

Showing Results 521 - 560, Page 14 of 18

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