12,214

Homes in ZIP Code 21550

Section Image
    • /27

      Est $109,437 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,056 Sq Ft

      32 Rockville Ct, Oakland, MD 21550

      32 Rockville Ct, Oakland, MD 21550
  • /56

    $725,000

    • 5 Beds
    • 3 Baths
    • 3,614 Sq Ft

    969 Hoyes Run Rd, Oakland, MD 21550

    Tucked among towering pines and hardwoods, this fully TURN KEY 5-bedroom log chalet blends natural beauty with cozy, upscale charm. The home sits on a gentle slope overlooking a meandering stream, its melodic sounds carrying through the trees and adding a tranquil soundtrack to life. A wraparound deck offers views of the forest and stream bank. Inside, the open floor plan welcomes you with a

    Roberta McNamara RE/MAX Results

    969 Hoyes Run Rd, Oakland, MD 21550
  • /12

    $380,000 Sold May 30, 2025

    • Land
    • 1.06 Acres
    • $358,491 per Acre
    • 4 Days On Market

    Lot 76 S Blakeslee Rd, Oakland, MD 21550

    If you have been searching for a beautiful homesite in the much sought after Blakeslee community, this is it. This lot is 1.06 acres and has an approved perc, the only hard decision you will have to make it, what style of home. Offering an assigned dock slip, access to an indoor pool, tennis courts, basketball court, soccer field and club house. The location is another plus, while feeling very

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    Lot 76 S Blakeslee Rd, Oakland, MD 21550
    • /48

      Est $321,338 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 1,750 Sq Ft

      314 Allegheny Dr, Oakland, MD 21550

      314 Allegheny Dr, Oakland, MD 21550
  • /51

    $554,900

    • 3 Beds
    • 3.5 Baths
    • 2,202 Sq Ft

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550

    SOLD TURN KEY - FULLY FURNISHED!!! As its vacation rental name describes, "Whispering Waters" provides a glistening open view of Deep Creek Lake from nearly every window! This 3 bedroom, 3 and 1/2 bath townhome is located right in the middle of all of the areas amenities and very close to restaurants, boat rentals, and more! All of the modern conveniences and finishes are included such as central

    Andrew Eiswert Railey Realty, Inc.

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
  • /29

    $220,000 Sold May 30, 2025

    • 1,296 Sq Ft
    • $170/SF
    • 16 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1998

    22 Black Oak Dr, Oakland, MD 21550

    Escape to your own mountain retreat in the beautiful, gated community of Yough Mountain Resort! Situated on a spacious 0.74-acre corner lot, this charming 3-bedroom, 2-bathroom cabin offers the perfect blend of rustic charm and modern comfort. Whether you're looking for a weekend escape or a full-time residence, you'll love the outdoor spaces—enjoy your morning coffee on the covered front patio,

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    22 Black Oak Dr, Oakland, MD 21550
    • /87

      Est $742,957 Not Listed For Sale

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

      34 Hooppole Ct, Oakland, MD 21550

      34 Hooppole Ct, Oakland, MD 21550
  • /39

    $485,000

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

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

    Lakefront Luxury at Will O’ The Wisp – Nicely renovated Unit 308/408 offers a 2 BR, 2 Bath 2- level floor plan perfect for guests or steady rental income. Enjoy breathtaking Deep Creek Lake views from every bedroom and the main living space. Resort-Style Amenities Include:Indoor Pool with Waterfall Hot Tub, Cedar-Lined Sauna, Fitness Room & Game Room, Sandy Lakefront Beach with Community

    Rich Orr Railey Realty, Inc.

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
  • /40

    $171,000 Sold May 30, 2025

    • 2,000 Sq Ft
    • $86/SF
    • 113 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1940

    5459 Hutton Rd, Oakland, MD 21550

    Endless Potential! This diamond in the rough is ready for your vision and creativity. A fantastic opportunity to make this home truly your own. Bring your tools and imagination---this home is waiting for a makeover. Great Investment property! It was used as a Duplex, home needs work but offers a great value for the right buyer. Newer furnace, newer windows installed throughout. Hardwood floors,

    Debra Beitzel Long & Foster Real Estate, Inc.

    5459 Hutton Rd, Oakland, MD 21550
    • /48

      Est $373,777 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 715 Sq Ft

      139 Bray School Rd, Oakland, MD 21550

      139 Bray School Rd, Oakland, MD 21550
  • /22

    $599,000

    • 2 Beds
    • 2 Baths
    • 1,584 Sq Ft

    355 Lonesome Pine Rd, Oakland, MD 21550

    Escape to your own private mountain retreat! This contemporary 2-bed, 2-bath home is perfectly situated on approximately 84 acres of pristine land, offering breathtaking views overlooking a picturesque 7-acre field. Expansive windows, high vaulted ceilings and an open layout maximize the stunning scenery, allowing natural light to flood the space. Whether you're seeking a peaceful getaway, an

    Brody Monahan Lake Homes Realty, LLC

    355 Lonesome Pine Rd, Oakland, MD 21550
  • /42

    $214,900 Sold May 29, 2025

    • 1,176 Sq Ft
    • $183/SF
    • 2 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1978

    501 Spruce St, Oakland, MD 21550

    3BR, 1.5BA rancher with 4 total garage stalls - 2 attached, 2 detached. Situated on .28 acres with a fenced backyard, spacious deck and a relatively private setting in Mt Lake Park. Partially remodeled with upgraded bathroom, master suite with electric fireplace, walk-in closet, updated flooring and appliances. 3rd bedroom currently getting a facelift with new drywall accent wall and new closet.

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    501 Spruce St, Oakland, MD 21550
    • /104

      Est $1,569,317 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,452 Sq Ft

      1000 S Blakeslee Rd, Oakland, MD 21550

      1000 S Blakeslee Rd, Oakland, MD 21550
  • /55

    $349,900

    • 1 Bed
    • 1 Bath
    • 496 Sq Ft

    565 Glendale Rd Unit 125, Oakland, MD 21550

    Wake up to the lake at your doorstep. This ground-level, end-unit condo puts you right where you want to be—direct lakefront with unbeatable access to everything Deep Creek offers. Walk out to the water, hit the gym, unwind in the sauna, or challenge friends in the game room. Dutch’s at Silver Tree, The Harbor Bar, and Silvertree Marina are all within reach, making lakeside dining and boat days

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 125, Oakland, MD 21550
  • /16

    $25,000 Sold May 27, 2025

    • Land
    • 0.00 Acre
    • 10 Days On Market

    36 Lehman Ln, Oakland, MD 21550

    Lot ready for building available in the beautiful Gallatin Woods community, located just minutes to all Deep Creek Lake area amenities! This gorgeous forested development offers the perfect area for a secluded mountain lake-house feel. While the condominium association maintains ownership of the land, Lot 36 is the perfect buildable lot for a single-family home with 8 beautiful pre-approved house

    Kellyann Green Railey Realty, Inc.

    36 Lehman Ln, Oakland, MD 21550
    • /87

      Est $424,780 Not Listed For Sale

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

      2702 Mayhew Inn Rd, Oakland, MD 21550

      2702 Mayhew Inn Rd, Oakland, MD 21550
  • /79

    $749,000

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft

    130 Timberloft Cir Unit 14, Oakland, MD 21550

    Centrally located in the heart of Deep Creek Lake, this beautifully maintained 3 bedroom, 3 bath home offers breathtaking lake and mountain views year round. Designed with an open floor plan, this home is perfect for entertaining. Enjoy the stunning scenery from the spacious main-level deck, or relax in the screened-in lower level porch. A cozy fireplace on both levels adds warmth and charm,

    Bill Weissgerber Railey Realty, Inc.

    130 Timberloft Cir Unit 14, Oakland, MD 21550
  • /51

    $435,000 Sold May 27, 2025

    • 2,750 Sq Ft
    • $158/SF
    • 306 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1995

    234 Maple Del Ln, Oakland, MD 21550

    3/4 BR, 3BA well-built & cared for home, 2700sf+/- in Maple Del, a private community in the Red Run area of Deep Creek Lake. Natural boulders lace the property; tall mature maples, oaks & pines offer plenty of shade but still ample lawn for outdoor activities. Surrounded by ferns, chirping birds and peace & quiet that's rare this close to the lake. You will love the cozy covered porch! Inside,

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    234 Maple Del Ln, Oakland, MD 21550
    • /77

      Est $183,098 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,852 Sq Ft

      214 I St, Oakland, MD 21550

      214 I St, Oakland, MD 21550
  • /33

    $695,000

    • 6 Beds
    • 2.5 Baths
    • 2,672 Sq Ft

    6652 George Washington Hwy, Oakland, MD 21550

    Beautiful home sitting on 35 acres, built by the current owners. Enter the main level into a grand foyer, with a lofty ceiling and beautiful chandelier. To the left is a separate dining room which leads to the large kitchen and living room. Off the living room is the primary bedroom with a huge walk-in closet and a full bathroom, including a newly installed walk-in shower. On the other side of

    Jessie Railey Railey Realty, Inc.

    6652 George Washington Hwy, Oakland, MD 21550
  • /32

    $1,699,900 Sold May 23, 2025

    • 3,096 Sq Ft
    • $549/SF
    • 6 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1940

    2353 Boy Scout Rd, Oakland, MD 21550

    Tucked away at the end of a country road, this fully reimagined lakefront lodge blends fairytale charm with warm modern style, offering over 3,000 square feet of carefully crafted space on a private .58-acre lot with 100’ of deep water frontage on the main body of Deep Creek Lake. Every inch is designed for relaxation, ease, and family—from the gourmet kitchen with custom hardwood cabinetry, live

    Jon Bell Railey Realty, Inc.

    2353 Boy Scout Rd, Oakland, MD 21550
    • /32

      Est $325,197 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths

      39 Laurel Brook Dr, Oakland, MD 21550

      39 Laurel Brook Dr, Oakland, MD 21550
  • /63

    $699,000 Pending

    • 5 Beds
    • 4 Baths
    • 3,105 Sq Ft

    130 Wisp Adventure Rd, McHenry, MD 21541

    Right in the heart of Deep Creek Lake, this modern mountain chalet checks all the boxes - Directly adjoining the ASCI White Water course, riverside to the slopes at Wisp! Five bedrooms, four full baths, and over 3,100 square feet of smart, stylish space. Open layout with a sharp white kitchen, gas fireplace, and plenty of natural light. Game room with pool table downstairs. Loft and lounge space

    Jon Bell Railey Realty, Inc.

    130 Wisp Adventure Rd, McHenry, MD 21541
  • /40

    $335,000 Sold May 23, 2025

    • 768 Sq Ft
    • $436/SF
    • 123 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1988

    465 King Wildesen Rd, Oakland, MD 21550

    Secluded Hunting Cabin with Breathtaking Mountain Views on 50 Acres Escape to your own private retreat with this charming 2-bedroom, 1-bathroom hunting cabin nestled on 50 acres of untouched wilderness. Perfectly designed for outdoor enthusiasts, this property offers the ultimate destination for hunting, hiking, and exploring. The expansive acreage features a diverse mix of wooded terrain, open

    ADAM MURRAY BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    465 King Wildesen Rd, Oakland, MD 21550
    • /42

      Est $224,896 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,920 Sq Ft

      19 A St, Oakland, MD 21550

      19 A St, Oakland, MD 21550
  • /63

    $719,000 Under Contract

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

    58 Glendale Woods Rd, Oakland, MD 21550

    Discover Easy Like Sunday Morning, a stunning 4-bedroom, 3-bath log cabin perfectly placed in the heart of Deep Creek Lake. This inviting retreat combines rustic charm with fresh upgrades, including a newly finished lower level that expands the living space and adds a spacious fourth bedroom. Gather around the open living area with soaring ceilings, or step onto the oversized deck to soak in

    Nina Beitzel Railey Realty, Inc.

    58 Glendale Woods Rd, Oakland, MD 21550
  • /21

    $155,000 Sold May 22, 2025

    • 1,232 Sq Ft
    • $126/SF
    • 10 Days On Market
    • 4 Beds
    • 1 Bath
    • Built 1964

    3821 Underwood Rd, Oakland, MD 21550

    An excellent financial opportunity close to Oakland. This 3 bedroom, 1 bathroom ranch can be a great starter home for a young family or a flip. It has good bones and all utilities are in working order. It has a metal roof, vinyl windows and good vinyl siding. The interior needs remodeling; some sweat equity will go a long way for the next owner.

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    3821 Underwood Rd, Oakland, MD 21550
    • /74

      Est $705,455 Not Listed For Sale

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

      14 Wanderer Ln, Oakland, MD 21550

      14 Wanderer Ln, Oakland, MD 21550
  • /9

    $49,900

    • Land
    • 1.00 Acre
    • $49,900 per Acre

    0 Longview Ln, Oakland, MD 21550

    1.00 Acre wooded lot loacted in George Brunson Subdivision. Close to Deep Creek Lake, Wisp Ski Resort and Oakland. Approved perc

    Linda Deremer Appalachian Realty

    0 Longview Ln, Oakland, MD 21550
  • /114

    $1,400,000 Sold May 19, 2025

    • 5,758 Sq Ft
    • $243/SF
    • 49 Days On Market
    • 6 Beds
    • 8 Baths
    • Built 2025

    186 Sundance Way, McHenry, MD 21541

    Luxury Log Home on Lodestone Golf Course – This brand-new 6 bed, 6 + 2 half bath log masterpiece delivers nearly 6,000 sq ft of pure elegance, finished in 2025 with a seamless blend of modern luxury and rustic charm. Nestled right along Hole #6, it offers a front-row seat to Deep Creek’s most scenic fairways. Open-concept great room that stuns with soaring ceilings, stone fireplace, and towering

    Michael Fenton Railey Realty, Inc.

    186 Sundance Way, McHenry, MD 21541
    • /73

      Est $998,473 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 4,160 Sq Ft

      375 Ridge View Ct, Oakland, MD 21550

      375 Ridge View Ct, Oakland, MD 21550
  • /83

    $1,999,900

    • 7 Beds
    • 7 Baths
    • 4,758 Sq Ft

    16 Grand Estates Dr, McHenry, MD 21541

    Brand New Mountain Chalet adjoining Lodestone Golf Course - Welcome to Sunset on the Greens. This custom Lindal 7-bedroom, 7-bath chalet is built for luxury mountain living at its finest. Already a proven rental performer, “Sunset on the Greens” grossed over $105k its first six months and all 5 star reviews! The great room steals the show with a towering wall of glass that opens to panoramic

    Jon Bell Railey Realty, Inc.

    16 Grand Estates Dr, McHenry, MD 21541
  • /82

    $1,900,000 Sold May 16, 2025

    • 2,249 Sq Ft
    • $845/SF
    • 5 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1989

    228 Paradise Heights, Oakland, MD 21550

    Discover the best of life at Deep Creek Lake in this 4-bedroom (2 en suites), 4.5-bath home. Perfectly situated with a nearly level lawn leading to 91' of lakefront, this property features a private Type A dock and a screened, lakeside gazebo. The spacious interior boasts lake views from nearly every room. The home's thoughtful layout includes multiple gathering areas, ideal for entertaining. A

    Jay Quinn Taylor Made Deep Creek Vacations & Sales

    228 Paradise Heights, Oakland, MD 21550
    • /57

      Est $331,893 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,863 Sq Ft

      840 Smouse Rd, Oakland, MD 21550

      840 Smouse Rd, Oakland, MD 21550
  • /6

    $120,000

    • Land
    • 0.57 Acre
    • $210,526 per Acre

    27 Biltmore Ridge Trail, Mc Henry, MD 21541

    Welcome to Lot 27, an exceptional homesite in one of the area's most prestigious mountaintop golf course communities. Here, the golf course is literally in your backyard, offering unbeatable views and direct access to one of Deep Creek’s premier destinations—Lodestone Golf Course.Set against a backdrop of panoramic mountain scenery, this lot is the perfect place to bring your dream home

    Anet Harris Taylor Made Deep Creek Vacations & Sales

    27 Biltmore Ridge Trail, Mc Henry, MD 21541
  • /67

    $259,000 Sold May 14, 2025

    • 960 Sq Ft
    • $270/SF
    • 4 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1984

    655 Bray School Rd, Oakland, MD 21550

    This cozy 2-bedroom, 1-bath home is full of charm and nestled in a peaceful, wooded setting among the pines. A front deck welcomes you inside to a warm living room with a gas fireplace, perfect for those cool mountain evenings. Just off the living room is a flexible space—ideal for a home office, reading nook, or cozy sitting area. An open spacious kitchen with new stove completes the living area

    Susan Bell Railey Realty, Inc.

    655 Bray School Rd, Oakland, MD 21550
    • /30

      Est $356,147 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,080 Sq Ft

      968 Paradise Heights, Oakland, MD 21550

      968 Paradise Heights, Oakland, MD 21550
  • /4

    $14,000

    • Land
    • 0.25 Acre
    • $56,000 per Acre

    0 E Reese St, Oakland, MD 21550

    Lot in town. Easy access to main roads and the Town of Oakland. Quiet St. Paved.

    Thomas Long Railey Realty, Inc.

    0 E Reese St, Oakland, MD 21550
  • /24

    $27,500 Sold May 14, 2025

    • 2,256 Sq Ft
    • $12/SF
    • 18 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1914

    107 E Mason St, Oakland, MD 21550

    Just outside of town this home is easy access to most amenities and just minutes from freshwater lake and snow skiing. Offers a nostalgic feel of days gone by in this simple kitchen . Check it out today and make it your own home sweet home.

    Kathleen Miller Better Homes & Gardens Real Estate Old Line Group

    107 E Mason St, Oakland, MD 21550
    • /105

      Est $389,805 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,920 Sq Ft

      1265 Bray School Rd, Oakland, MD 21550

      1265 Bray School Rd, Oakland, MD 21550

Showing Results 241 - 280, Page 7 of 18

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