12,214

Homes in ZIP Code 21550

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  • /93

    $3,489,000

    • 5 Beds
    • 5.5 Baths
    • 5,100 Sq Ft

    1931 Lake Shore Dr, Oakland, MD 21550

    Deep Creek Lakes, Sunset Hills, luxury retreat offering majestic mountain & lake views. A unique lakefront property that plays a perfect host to relaxing vacations with family and friends is a low-key lifestyle centered around the outdoors. Vast stretches of glass ensure a sparkling water view is always on hand. Though sleek materials and high-end finishes abound, their low-profile design puts

    Russell Bounds Railey Realty, Inc.

    1931 Lake Shore Dr, Oakland, MD 21550
  • /44

    $140,000 Sold Jul 08, 2025

    • 1,680 Sq Ft
    • $83/SF
    • 86 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1953

    15 D St, Oakland, MD 21550

    Solid bones with room to grow. This two-bedroom, one-and-a-half-bath home sits in a quiet spot in Mountain Lake Park, offering a fenced front and back yard for privacy, pets, or play. A detached garage adds extra storage or a workshop. Conveniently located near Downtown Oakland and just 20 minutes from McHenry, it’s a prime spot with potential. Whether you're looking for a starter home or a

    Jon Bell Railey Realty, Inc.

    15 D St, Oakland, MD 21550
    • /46

      Est $179,216 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 911 Sq Ft

      259 N Bradley Ln, Oakland, MD 21550

      259 N Bradley Ln, Oakland, MD 21550
  • /53

    $1,599,900

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

    1674 Paradise Point Rd, Oakland, MD 21550

    Beautifully remodeled lakefront home offering private dock and stunning views of Deep Creek Lake! Located on Paradise Point Rd, this home faces south for abundant natural light. 4 Bedrooms, 2.5 Bathrooms and sold fully furnished providing a gorgeous contemporary aesthetic throughout. Brand-new roof caps the Bright and Open Space with lots of glass to bring in the scenic lake views! Cozy fireplace

    Jon Bell Railey Realty, Inc.

    1674 Paradise Point Rd, Oakland, MD 21550
  • /40

    $615,000 Sold Jul 07, 2025

    • 2,280 Sq Ft
    • $270/SF
    • 51 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2003

    245 Santa fe Trail, Oakland, MD 21550

    3/4BR 3BA chalet with LAKE VIEWS! 2300sf vacation home fronting on a mountain stream, backing to woods & boulders and overlooking Deep Creek Lake! Enjoy an eat-in kitchen, exposed beams and a loft area that the current owners use as a 4th BR with bathroom. Conveys fully furnished. Features include updated flooring, gas fireplace on main level, lower level rec room with pool table and

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    245 Santa fe Trail, Oakland, MD 21550
    • /58

      Est $425,740 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft

      2734 Mayhew Inn Rd, Oakland, MD 21550

      2734 Mayhew Inn Rd, Oakland, MD 21550
  • /84

    $829,000

    • 3 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    105 Mountain Overlook Ct, McHenry, MD 21550

    Discover mountain luxury in this beautifully maintained 3-bedroom, 3.5-bath Mountaintop Chalet near Wisp Resort with scenic Deep Creek Lake access. Exceptional craftsmanship and upscale finishes shine throughout its bright, open layout designed for entertaining. Gather in the cozy living room with stone fireplace, enjoy the comfort of a wonderful family room and versatile loft, and take advantage

    Steven Ritchie Railey Realty, Inc.

    105 Mountain Overlook Ct, McHenry, MD 21550
  • /23

    $18,000 Sold Jul 03, 2025

    • Land
    • 0.80 Acre
    • $22,500 per Acre
    • 5 Days On Market

    Lot 9 Birchwood Dr, Oakland, MD 21550

    Lot 9 Birchwood Drive is a .80 acre wooded lot in the desirable gated community of Youghiogheny Mountain Resort. Approved for an at-grade septic system for up to 4 bedrooms, this is great opportunity to build your future home or vacation retreat. Enjoy access to community amenities including over 50 miles of ATV/snowmobile trails, river access, community center, outdoor pavilion, and much more.

    Nick Fratz-Orr Railey Realty, Inc.

    Lot 9 Birchwood Dr, Oakland, MD 21550
    • /76

      Est $1,159,104 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,216 Sq Ft

      1882 Marsh Hill Rd, Mc Henry, MD 21541

      1882 Marsh Hill Rd, Mc Henry, MD 21541
  • /123

    $1,600,000

    • 7 Beds
    • 5.5 Baths
    • 5,200 Sq Ft

    188 Highline Dr, Mc Henry, MD 21541

    Welcome to your dream mountain retreat at Wisp Resort! Rare opportunity to own a ski-in/ski-out access home with dramatic 12-mile lake views from all three floors. New appliance and investment upgrades throughout the home as of July 2025. Your near-zero maintenance DREAM: cedar shakes boasting upwards of 50-years longevity, ultra durable hardy board siding, a freshly painted deck, and a naturally

    Elizabeth Ware Railey Realty, Inc.

    188 Highline Dr, Mc Henry, MD 21541
  • /35

    $285,000 Sold Jul 03, 2025

    • 1,344 Sq Ft
    • $212/SF
    • 16 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1979

    506 Cedar Ln, Oakland, MD 21550

    Tucked away on 1.42 acres across three wooded lots, this recently remodeled 3-bedroom, 2-bath home offers the perfect blend of comfort, character, and privacy. Step onto the expansive front deck, where mornings are made for sipping coffee and soaking in the peaceful surroundings. Inside, you'll find beautiful bamboo floors flowing through the open living, kitchen, and dining spaces—ideal for cozy

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    506 Cedar Ln, Oakland, MD 21550
    • /32

      Est $1,399,237 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,956 Sq Ft

      1842 Stockslager Rd, Oakland, MD 21550

      1842 Stockslager Rd, Oakland, MD 21550
  • /93

    $3,249,000 New Construction

    • 4 Beds
    • 5 Baths
    • 6,036 Sq Ft

    415 Nazelrod Rd, Oakland, MD 21550

    One of Garrett County's most unique and breathtaking estates—this completely custom masterpiece is set on over 63 acres of pristine land, offering unmatched privacy, panoramic valley views, and endless possibilities. Designed with meticulous attention to detail, built with 2x10 framing, this extraordinary home of over 6,000 total square feet features radiant in-floor heating, a gourmet kitchen

    Larry Smith Railey Realty, Inc.

    415 Nazelrod Rd, Oakland, MD 21550
  • /9

    $145,000 Sold Jul 03, 2025

    • Land
    • 0.36 Acre
    • $402,778 per Acre
    • 53 Days On Market

    30 Snowshoe Ct, McHenry, MD 21541

    Can’t find the mountain home you’ve been searching for? Build it your way on this level, wooded .36-acre lot in Highline! Private ski trail access to Wisp Resort. Located near the end of a quiet cul-de-sac, this property offers public water and sewer- ready to build! Perfect for a future vacation rental or your own Deep Creek escape. Surrounded by adventure with skiing, snow tubing, the mountain

    Michael Fenton Railey Realty, Inc.

    30 Snowshoe Ct, McHenry, MD 21541
    • /5

      Est $169,687 Not Listed For Sale

      133 Fox Den Rd, Oakland, MD 21550

      133 Fox Den Rd, Oakland, MD 21550
  • /45

    $875,000 New Construction

    • 3 Beds
    • 4 Baths
    • 1,858 Sq Ft

    17 Green Jacket Ct, McHenry, MD 21541

    Luxury one-level living: Atop the mountain in the Lodestone golf community, "Mountain Whisper" has the modern comfort you will want for your vacation retreat or full-time residence. To convey turn-key, you will enjoy the open concept living area, w/easy access to a gourmet kitchen & dining, 3BDR/2BA & 2 half baths. Enjoy your outdoor recreation space with an upgraded fire pit, covered outdoor

    Kathy Gibson Railey Realty, Inc.

    17 Green Jacket Ct, McHenry, MD 21541
  • /92

    $420,000 Sold Jul 03, 2025

    • 2,380 Sq Ft
    • $176/SF
    • 45 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1989

    26 Bright Passage Rd Unit 3C, McHenry, MD 21541

    Tired of choosing between lake days and ski runs? Villages of Wisp offers the best of both worlds! Ski access in the winter. Lake access all summer. Updated top to bottom with newer appliances, fresh carpet, sleek flooring, and modern vanities in all three bathrooms. Ductless AC. A private loft on the third floor adds bonus space without stealing a bedroom. Soak in the mountain lake views from

    Jon Bell Railey Realty, Inc.

    26 Bright Passage Rd Unit 3C, McHenry, MD 21541
    • /70

      Est $250,881 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,332 Sq Ft

      402 Leighton Dr, Oakland, MD 21550

      402 Leighton Dr, Oakland, MD 21550
  • /79

    $999,500 Pending

    • 4 Beds
    • 2 Baths
    • 2,230 Sq Ft

    1473 Pergin Farm Rd, Oakland, MD 21550

    TIME TO UNWIND at this absolutely stunning Deep Creek Lake retreat boasting million-dollar panoramic views and private lake access! This fully furnished, meticulously renovated 4-bedroom, 2-bath raised rancher is the ultimate escape—perfect for weekend getaways, full-time living, or a savvy investment—sited on 2 pristine acres in the highly sought-after Pergin Farm community, a peaceful peninsula

    Tony Migliaccio Long & Foster Real Estate, Inc.

    1473 Pergin Farm Rd, Oakland, MD 21550
  • /41

    $148,000 Sold Jul 02, 2025

    • 1,494 Sq Ft
    • $99/SF
    • 4 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1940

    116 N 8th St Unit 2, Oakland, MD 21550

    This charming 2-bedroom, 1-bath house offers the perfect blend of comfort and potential. Step inside to find a cozy living space adorned with upgraded carpet and flooring, creating a warm and inviting atmosphere perfect for relaxing or entertaining.One of the standout features of this property is the massive garage, providing ample space for vehicles, storage, or even a workshop. With

    Duane Stein II Keller Williams Realty Centre

    116 N 8th St Unit 2, Oakland, MD 21550
    • /17

      Est $231,636 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,345 Sq Ft

      404 Fairway Dr, Oakland, MD 21550

      404 Fairway Dr, Oakland, MD 21550
  • /73

    $529,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    346 Skippers Point Rd, Oakland, MD 21550

    Escape to your ideal mountain-lake retreat at Deep Creek Lake with this charming chalet-style home, nestled in a peaceful, wooded setting. This warm and inviting 3-bedroom, 2-bath getaway blends rustic charm with modern comfort—perfect as a vacation home or full-time residence. Take in filtered lake views from your home and expansive deck or relax by the lake with exclusive access to a sandy

    Steven Ritchie Railey Realty, Inc.

    346 Skippers Point Rd, Oakland, MD 21550
  • /45

    $435,000 Sold Jul 02, 2025

    • 1,838 Sq Ft
    • $237/SF
    • 626 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2004

    256 Jeffrey Ln Unit 28, Oakland, MD 21550

    Looking for an updated condo at Deep Creek Lake? Look no further! 256 Jeffrey Lane #28 is a 3BR/3.5BA condo at Traders Landing offering lake views just across the street from the lake. Centrally located, you can be at most area amenities within minutes from your front door. Northern exposure makes for great all day sun. Recent improvements include renovated kitchen, bathrooms and furnishings.

    Nick Fratz-Orr Railey Realty, Inc.

    256 Jeffrey Ln Unit 28, Oakland, MD 21550
    • /49

      Est $248,207 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,408 Sq Ft

      352 Fawn Dr, Oakland, MD 21550

      352 Fawn Dr, Oakland, MD 21550
  • /61

    $689,000 Under Contract

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

    1006 Lake Shore Dr, Oakland, MD 21550

    Located in the scenic Deep Creek Lake area, this well-kept 4-bedroom home offers comfort, space, and convenience with filtered lake views and a functional layout that allows for one-level living if desired. Sold turn key and situated on a generous lot, the property features an oversized front and back yard, ideal for outdoor enjoyment, along with a large wrap-around paved driveway and an attached

    Nina Beitzel Railey Realty, Inc.

    1006 Lake Shore Dr, Oakland, MD 21550
  • /20

    $80,000 Sold Jun 30, 2025

    • 1,860 Sq Ft
    • $43/SF
    • 5 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1965

    81 Timber Ln, Oakland, MD 21550

    If you’re in the market for an affordable home, this could be the perfect option for you! Located in Crellin, just a few minutes from Oakland, this property features an oversized three-bay garage and an upstairs studio, offering plenty of possibilities. Whether you want to work on cars or create a fantastic woodworking shop, the space is versatile. The four-bedroom home boasts its original oak

    Sheila Howell Lake Homes Realty, LLC

    81 Timber Ln, Oakland, MD 21550
    • /31

      Est $389,972 Not Listed For Sale

      • 5 Beds
      • 1 Bath
      • 2,280 Sq Ft

      1793 Kempton Rd, Oakland, MD 21550

      1793 Kempton Rd, Oakland, MD 21550
  • /42

    $565,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,564 Sq Ft

    793 Mountainview Dr, Oakland, MD 21550

    It’s here! And priced to sell! An updated rustic-modern home with lots of privacy on a large wooded lot in the coveted Mountainside Resort of Deep Creek Lake.Discover rustic elegance and modern comfort in this beautifully updated 3-bedroom, 2.5-bath lake access home nestled on a private, wooded 1.18-acre lot in the coveted Mountainside community at Deep Creek Lake. Offering one-level

    Mike Kennedy Railey Realty, Inc.

    793 Mountainview Dr, Oakland, MD 21550
  • /53

    $1,055,000 Sold Jun 30, 2025

    • 5,712 Sq Ft
    • $185/SF
    • 7 Days On Market
    • 6 Beds
    • 5.5 Baths
    • Built 2019

    193 Greenbrier Dr, McHenry, MD 21541

    Discover high-elevation luxury at this 2019-built masterpiece perched atop Wisp Ski Resort in the sought-after Lodestone Golf Course community of Greenbrier at Deep Creek Lake! Boasting over 5,000 sq ft of finished living space, this impressive 6-bedroom, 5.5-bath home built in 2019 blends upscale comfort with mountain adventure, making it the ultimate four-season retreat or income-generating

    Mike Kennedy Railey Realty, Inc.

    193 Greenbrier Dr, McHenry, MD 21541
    • /67

      Est $268,734 Not Listed For Sale

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

      218 Weber Rd, Oakland, MD 21550

      218 Weber Rd, Oakland, MD 21550
  • /65

    $299,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 2,208 Sq Ft

    290 Crellin Underwood Rd, Oakland, MD 21550

    Awesome 3BR/2BA Log home sitting on 2 acre lot. Third bedroom in on lower level and does not have an egress window. Full bath with soaking tub on main level with 24 X 12 bedroom and additional BR. Full bath on lower level as well. Huge Family Room with Native Stone wall with wood burning stove to supplement heating system. Heat is propane forced air. Large deck, partially covered on main level.

    Kevin Liller Railey Realty, Inc.

    290 Crellin Underwood Rd, Oakland, MD 21550
  • /22

    $25,000 Sold Jun 27, 2025

    • Land
    • 1.05 Acres
    • $23,810 per Acre
    • 84 Days On Market

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550

    5 bedroom perc! Experience a quiet & secluded area of Deep Creek Lake. The Overlook is a lake view and water access community in the southernmost expanse of the lake. Lot 22 is close to the water & shares 21+/- acres of beautiful common area, including a lakeside walking/hiking trail and lakeside gazebo. Teeming with birds and other wildlife, the namesake stream 'Deep Creek' doesn't disappoint!

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    • /57

      Est $1,010,124 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,485 Sq Ft

      296 Highline Dr, Mc Henry, MD 21541

      296 Highline Dr, Mc Henry, MD 21541
  • /82

    $569,900 Under Contract

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

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550

    Overlooking Deep Creek Lake, this modern townhome delivers luxury, comfort, and unbeatable convenience. Located in Timberlake Village, the 5-bedroom, 4.5-bath retreat is minutes from top restaurants, marinas, state parks, and Wisp Resort. The main level was recently reimagined with contemporary lighting and timber accents, a modern kitchen featuring granite counters, stainless appliances, and a

    Jon Bell Railey Realty, Inc.

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
  • /10

    $59,000 Sold Jun 26, 2025

    • Land
    • 6 Acres
    • $9,486 per Acre
    • 15 Days On Market

    Lot 9 Pheasant Run, Oakland, MD 21550

    Lot 9 Pheasant Run Road is 6.22-acre building lot in the desirable Moss Creek subdivision at Deep Creek Lake. Gently wooded with small, easily clearable brush, this parcel offers stunning mountain views and western exposure—ideal for enjoying breathtaking sunsets. Conveniently located just minutes from Deep Creeks recreational amenities and the shops, dining, and services of Oakland, MD. This

    Zach Wesolowski Railey Realty, Inc.

    Lot 9 Pheasant Run, Oakland, MD 21550
    • /71

      Est $817,828 Not Listed For Sale

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

      589 Mountainview Dr, Oakland, MD 21550

      589 Mountainview Dr, Oakland, MD 21550
  • /74

    $699,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 1,716 Sq Ft

    41 Sandstone Cir, Mc Henry, MD 21541

    Experience mountain tranquility in this stunning 4 bedroom, 3 bathroom chalet bordering Lodestone Golf Course. The main floor of this masterpiece features a primary suite and second main level bedroom along with 2 full bathrooms, and a beautifully updated open kitchen/dining/living room space thats perfect for entertaining. Enjoy walkout sliding doors from the main level onto the covered porch

    Justin Liller Railey Realty, Inc.

    41 Sandstone Cir, Mc Henry, MD 21541
  • /71

    $899,900 Sold Jun 26, 2025

    • 2,106 Sq Ft
    • $427/SF
    • 135 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2007

    145 Lower Penn Point Dr, Oakland, MD 21550

    **SPLIT LAKE FRONT** WITH TYPE A DOCK**Discover this stunning chalet-style home located in the coveted Penn Point subdivision at Deep Creek Lake. Luxury vinyl plank flooring through out, fresh paint, all new decking and railings, new pine tongue and groove through-out giving a warm lodge feel. The main floor is open concept, living, dining, kitchen and half bath, the upper level presents 2

    Emillie Albrecht Real Broker, LLC

    145 Lower Penn Point Dr, Oakland, MD 21550
    • /90

      Est $1,516,558 Not Listed For Sale

      • 4 Beds
      • 6 Baths
      • 3,008 Sq Ft

      3037 Shingle Camp Rd, Mc Henry, MD 21541

      3037 Shingle Camp Rd, Mc Henry, MD 21541
  • /142

    $5,150,000

    • 8 Beds
    • 8.5 Baths
    • 10,300 Sq Ft

    1010 Holy Cross Dr, Oakland, MD 21550

    ICONIC. A design masterpiece of stone and timber — a true Rex Anderson build that reflects the seamless merging of inspiration and architecture. Warm, and undeniably welcoming, this home stands as a statement of craftsmanship and vision. Discover a breathtaking blend of contemporary luxury and timeless timber frame construction, perfectly positioned for privacy within the prestigious

    Rachel Bruch Railey Realty, Inc.

    1010 Holy Cross Dr, Oakland, MD 21550

Showing Results 161 - 200, Page 5 of 18

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