12,218

Homes in ZIP Code 21550

Section Image Section Image
  • /72

    $1,075,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,232 Sq Ft

    267 Woodlands Hill Ln, Oakland, MD 21550

    267 Woodlands Hill Lane offers mountain living at its finest! This custom, 2021 built chalet is designed for ultimate comfort and enjoyment. The mountain setting offers breathtaking views with a location close to all of the areas most desirable amenities. Offering 4 bedrooms, 3.5 bathrooms and 3 levels of living, this home offers plenty of room for entertaining guests. You'll be greeted with oak

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 434-0226

    267 Woodlands Hill Ln, Oakland, MD 21550
  • /6

    $1,550 per month

    • 3 Beds
    • 1 Bath
    • 2,312 Sq Ft
    • Condo for Rent

    400 E Alder St Unit 3, Oakland, MD 21550

    Newly renovated second floor apartment with 3 bedrooms freshly painted, with new floors and a fully renovated bathroom. The apartment boasts high ceilings and charming original fixtures. Located in the heart of downtown its within walking distance of shops and restaurants!

    Sharon Mokhtari Fairfax Realty of Tysons

    400 E Alder St Unit 3, Oakland, MD 21550
  • /78

    $760,000 Sold Sep 15, 2025

    • 2,218 Sq Ft
    • $343/SF
    • 5 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2021

    61 Par Way, Mc Henry, MD 21541

    With beautiful views of the Lodestone Golf Course, this stunning log chalet—tucked along a peaceful drive in the prestigious Biltmore at Lodestone community—is a must-see! Past the entryway, step into open-concept living with oversized windows for plenty of natural lighting, accentuating the drywall/wood siding interior combination that makes the home feel both natural and modern. The exterior

    Elizabeth Ware Railey Realty, Inc.

    61 Par Way, Mc Henry, MD 21541
    • /30

      Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 382 Sq Ft

      565 Glendale Rd Unit 123-A, Oakland, MD 21550

      565 Glendale Rd Unit 123-A, Oakland, MD 21550
  • /47

    $925,000

    • 4 Beds
    • 3 Baths
    • 2,512 Sq Ft

    130 Lodestone Way, Mc Henry, MD 21541

    Welcome to "Golden Overlook" — a beautifully furnished, brand-new mountain retreat built in 2024 tucked alongside Lodestone Golf Course and just minutes from Deep Creek Lake and Wisp Ski Resort. With 4 bedrooms, 3 full baths, and over 2,500 square feet of finished space, this home offers the perfect blend of modern comfort and mountain charm.From the moment you step inside, you’ll be

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (240) 358-3652

    130 Lodestone Way, Mc Henry, MD 21541
  • /11

    $1,650 per month

    • 2 Beds
    • 1.5 Baths
    • 3,350 Sq Ft
    • House for Rent

    604 E Oak St, Oakland, MD 21550

    CCharming 2-Bedroom Apartment Recently Renovated, Prime Location!Welcome to this beautifully renovated 2-bedroom apartment, where modern design meets comfort. Located in a quiet neighborhood, this home is just a short walk from downtown Oakland, offering the perfect blend of convenience and peaceful living.Key Features:Complete Renovation: Enjoy a fresh and stylish space with all-new

    Sharon Mokhtari Fairfax Realty of Tysons

    604 E Oak St, Oakland, MD 21550
  • /74

    $915,000 Sold Sep 15, 2025

    • 2,347 Sq Ft
    • $390/SF
    • 48 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1992

    186 Thornberry Rd, Oakland, MD 21550

    186 Thornberry is a lovely lake access contemporary in the much sought after Blakeslee community on the shores of Deep Creek Lake. This home feels warm and inviting from the moment you pull in the driveway. The detail to the landscaping and beautiful shrubbery makes a very nice first impression. Upon entering, the layout flows very nicely with two stone wood burning fireplaces, a great enclosed

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    186 Thornberry Rd, Oakland, MD 21550
    • /60

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,735 Sq Ft

      314 Morning Glory Dr, Oakland, MD 21550

      314 Morning Glory Dr, Oakland, MD 21550
  • /47

    $300,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H708, Oakland, MD 21550

    Welcome to Will O' the Wisp Condominiums, where premium upgrades meet penthouse-level lakefront living at Deep Creek Lake! This fully furnished, beautifully updated, rarely available, top-floor two-level condo features one bedroom and one bath, offering 550 square feet of comfort, charm, and versatility — perfect as a vacation home, year-round retreat, or income-producing rental.Start

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (301) 479-6357

    20160 Garrett Hwy Unit H708, Oakland, MD 21550
  • /18

    $200,000 Sold Sep 15, 2025

    • 1,678 Sq Ft
    • $119/SF
    • 62 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1985

    2571 Shady Dell Rd, Oakland, MD 21550

    They call it Pleasant Valley for a reason! The property features a 2+ acre wooded area, a serene stream, several berry plants, 2 sheds, chicken coop, and a rear deck. Front porch and a fenced-in front yard. Inside, there is a large, bright living room, an updated kitchen with plenty of cabinet space, appliances, and sliding glass doors leading to the deck. The bathrooms have been updated. Full

    Paul Macy Garrett Land Sales, PC

    2571 Shady Dell Rd, Oakland, MD 21550
    • /20

      Est $247,719 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 484 Sq Ft

      565 Glendale Rd Unit 208, Oakland, MD 21550

      565 Glendale Rd Unit 208, Oakland, MD 21550
  • /71

    $1,985,000

    • 4 Beds
    • 4 Baths
    • 4,150 Sq Ft

    62 Duck Cove Rd, Oakland, MD 21550

    Panoramic lakefront living greets you on the point of this remarkable 4 bedroom, 4 bathroom lakefront home with 231' of premium lakefront facing east, offering amazing sunrises looking down a long stretch of the lake toward Turkeyneck! 1 oversize attached garage spaces offer plenty of space for your vehicles on the street side and 2 attached garage spaces provide room for your lake toys on the

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 376-4139

    62 Duck Cove Rd, Oakland, MD 21550
  • /86

    $770,000 Sold Sep 15, 2025

    • 2,962 Sq Ft
    • $260/SF
    • 380 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2017

    722 Winding Estates Dr, Mc Henry, MD 21541

    722 Windings Estates offers one of the most elegant mountain homes Deep Creek Lake has to offer. This 4BR/2.5BA home spans over 2 levels with over 3000 square feet of living space and a premium, 1 acre lot. Enjoy the evening sunsets looking over the lake from the expansive porch with western exposure or a warm cup of coffee on the covered back porch. Entertain guests in the premium main level

    Nick Fratz-Orr Railey Realty, Inc.

    722 Winding Estates Dr, Mc Henry, MD 21541
    • /14

      Not Listed For Sale

      0 Maryland Hwy Unit 1000110045, Mountain Lake Park, MD 21550

      0 Maryland Hwy Unit 1000110045, Mountain Lake Park, MD 21550
  • /52

    $650,000

    • 3 Beds
    • 3 Baths
    • 1,740 Sq Ft

    65 Village Dr Unit 6, Oakland, MD 21550

    Looking for that cozy cabin getaway at the lake? 65 Village Drive offers cabin living at its finest with 3 full bedrooms and 3 full bathrooms minutes from all of Deep Creek Lake's most popular amenities. Two wood burning fireplaces give ultimate ambiance in the main level living room and four seasons room where the hot tub is also located. Many recent improvements including appliances, HVAC ,

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 759-2822

    65 Village Dr Unit 6, Oakland, MD 21550
  • /22

    $180,000 Sold Sep 12, 2025

    • 864 Sq Ft
    • $208/SF
    • 4 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1979

    4643 Oakland Sang Run Rd, Oakland, MD 21550

    Set between Oakland and Deep Creek, this main-level ranch runs new granite, black stainless, six-burner gas, and dual-ice fridge. Baths are tiled with updated vanities and floors. Plank flooring throughout. Basement is unfinished with storage, laundry, walkout, and room to expand. Heat pump with electric backup and central air. Vinyl siding, newer roof, wraparound deck. Extra wooded lot next door

    Jon Bell Railey Realty, Inc.

    4643 Oakland Sang Run Rd, Oakland, MD 21550
    • /3

      Not Listed For Sale

      7 Cherrywood Dr, Oakland, MD 21550

      7 Cherrywood Dr, Oakland, MD 21550
  • /37

    $440,000

    • 2 Beds
    • 1 Bath

    15 Village Dr Unit 1, Oakland, MD 21550

    Escape to a simpler time with all the modern conveniences you desire at this 2-bedroom log cabin in the Yellowstone Village. The main level envelops you with the uniqueness and charm from the great room with an old-fashioned stone fireplace to warm up the chilling evenings and furniture that begs you to sit a while, to the quaint, yet full-sized kitchen with the cutest dining table. Venture up

    Agent Photo

    Dale Carpenter

    Railey Realty, Inc.

    (240) 255-9771

    15 Village Dr Unit 1, Oakland, MD 21550
  • /41

    $239,900 Sold Sep 12, 2025

    • 1,680 Sq Ft
    • $143/SF
    • 17 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1956

    502 E Oak St, Oakland, MD 21550

    Welcome to this meticulously maintained one-level home in the heart of Oakland, MD! Boasting a spacious and thoughtfully designed interior, this 3-bedroom, 2-bathroom residence offers comfortable, easy living with room to relax and entertain. The open layout includes a bright living area, a well-appointed kitchen, and generous bedrooms that provide the perfect balance of privacy and convenience.

    Nina Beitzel Railey Realty, Inc.

    502 E Oak St, Oakland, MD 21550
    • /3

      Not Listed For Sale

      65 Kendall Camp Cir, McHenry, MD 21541

      65 Kendall Camp Cir, McHenry, MD 21541
  • /97

    $695,000

    • 4 Beds
    • 3 Baths
    • 3,242 Sq Ft

    621 Paradise Heights, Oakland, MD 21550

    Opportunity to own one of Deep Creek Lake's most unique homes! 621 Paradise Heights is a geodesic dome house offering 4 bedrooms, 3 full bathrooms and over 4300 square feet of interior space. Become the ultimate host of guests with the many entertainment spaces in the house including main level living room, parlor with wet bar, expansive deck, stacked stone fireplace, fit pit in back yard and

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 998-1539

    621 Paradise Heights, Oakland, MD 21550
  • /65

    $280,500 Sold Sep 12, 2025

    • 2,208 Sq Ft
    • $127/SF
    • 96 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1982

    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
    • /16

      Not Listed For Sale

      128 Tarn Dr, Oakland, MD 21550

      128 Tarn Dr, Oakland, MD 21550
  • /35

    $250,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 660 Sq Ft

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550

    Welcome to "Lakeview Loft" – your perfect Deep Creek getaway! This 2-bedroom, 1-bathroom unit offers expansive lake views and a central location that puts you in the heart of Deep Creek Lake. Enjoy your morning coffee with panoramic water views, or take a short walk to one of Deep Creek’s most popular plazas for your shopping and dining needs. Whether you're looking for a weekend retreat, a

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 623-5426

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
  • /44

    $589,000 Sold Sep 08, 2025

    • 1,027 Sq Ft
    • $574/SF
    • 62 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1995

    939 Glendale Rd, Oakland, MD 21550

    This is the perfect one level condo right on the lake!! Just a few steps from your dock slip, and crazy amazing views!!! This place offers luxury vinyl flooring that is easy to maintain as well as so many other upgrades. The primary bedroom has a large walk-in closet and attached bath with a separate soaking jacuzzi tub. It is being sold furnished and with a whole house dehumidifier. Just bring

    Sheila Howell Lake Homes Realty, LLC

    939 Glendale Rd, Oakland, MD 21550
    • /22

      Not Listed For Sale

      • 4 Beds

      1 Overlook Ridge Dr SE, Oakland, MD 21550

      1 Overlook Ridge Dr SE, Oakland, MD 21550
  • /48

    $289,000 Under Contract

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

    215 N 10th St, Oakland, MD 21550

    Welcome home to this recently renovated ranch featuring 3 bedrooms, 1 bathroom, and approximately 1,500 sq ft of bright, single-level living. Timeless hardwood floors flow through an open, easy layout that's ideal for everyday life and effortless entertaining. New windows invite generous natural light throughout, and the refreshed kitchen with modern finishes anchors the heart of the home,

    Agent Photo

    ADAM MURRAY

    BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    (240) 262-4001

    215 N 10th St, Oakland, MD 21550
  • /62

    $1,399,000 Sold Sep 05, 2025

    • 1,872 Sq Ft
    • $747/SF
    • 3 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2020

    1589 Lake Shore Dr, Oakland, MD 21550

    Exquisite one of a kind contemporary tucked away on sought after Lake Shore Drive. 128 feet of lake frontage on quiet Bee Tree Hollow Cove, with 20-foot-deep water depths off spacious Type A dock and total privacy. Perched high above the cove “The Birdhouse” offers expansive four-season views from every window. The property was thoughtfully designed and planned by current owners and local

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    1589 Lake Shore Dr, Oakland, MD 21550
    • /48

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft

      20160 Garrett Hwy Unit 502/702, Oakland, MD 21550

      20160 Garrett Hwy Unit 502/702, Oakland, MD 21550
  • /33

    $175,000

    • 1 Bed
    • 1 Bath
    • 382 Sq Ft

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

    Studio unit at Silver Tree Suites, one of Deep Creek Lake's most premier condo/hotel communities! Silver Tree Suites offers over 350' of pristine lakefront with western exposure. Located directly adjacent to Dutch's at Silver Tree, this location offers convenience to one of the areas most desirable restaurants, and is only 5-10 minutes to all of the local amenities and attractions you come to

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 623-5408

    565 Glendale Rd Unit 210-A, Oakland, MD 21550
  • /61

    $275,000 Sold Sep 05, 2025

    • 1,488 Sq Ft
    • $185/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1940

    648 S 3rd St, Oakland, MD 21550

    An extremely charming 3 bed 2 full bath home located on one of the most desired and convenient streets in Oakland and the gateway to the valley. This home has had recent tasteful upgrades and TLC making it move-in ready and with a sturdy oversized garage and partially fenced in side yard, the comforts of home are everywhere.

    Andrew Eiswert Railey Realty, Inc.

    648 S 3rd St, Oakland, MD 21550
    • /64

      Est $643,025 Not Listed For Sale

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

      305 Winding Trail Ln Unit 12A, Oakland, MD 21550

      305 Winding Trail Ln Unit 12A, Oakland, MD 21550
  • /60

    $295,000

    • 4 Beds
    • 2.5 Baths
    • 1,528 Sq Ft

    1056 Sunrise Dr, Oakland, MD 21550

    Welcome to 1056 Sunrise Drive! This 4-bedroom, 2-bath home offers the perfect blend of comfort and style in the heart of Oakland MD. Inside, enjoy recent renovations that add a cozy appeal throughout, including a bright and open main living area, and a refreshed kitchen and bathrooms. The fully finished basement adds valuable living space, perfect for a rec room, home office, or guest suite. Set

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 219-8052

    1056 Sunrise Dr, Oakland, MD 21550
  • /75

    $1,525,000 Sold Sep 04, 2025

    • 3,696 Sq Ft
    • $413/SF
    • 125 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1999

    1419 Sandy Shores Rd, Mc Henry, MD 21541

    Set in a peaceful, wooded landscape, this stunning lakefront home offers a perfect mix of comfort and natural beauty right in the heart of Deep Creek Lake. With 5 spacious bedrooms and 5 well-appointed baths, this three-level retreat provides breathtaking views from multiple vantage points. The main level features an inviting open-concept design, a gourmet kitchen, and a bright, airy living space

    Nina Beitzel Railey Realty, Inc.

    1419 Sandy Shores Rd, Mc Henry, MD 21541
    • /22

      Est $269,041 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,208 Sq Ft

      18113 Garrett Hwy, Oakland, MD 21550

      18113 Garrett Hwy, Oakland, MD 21550
  • /50

    $335,000

    • 3 Beds
    • 2.5 Baths
    • 1,416 Sq Ft

    163 Crestview Dr, Oakland, MD 21550

    Welcome to 163 Crestview Drive — a beautifully maintained 3-bedroom, 2.5-bath home nestled in the Mitchell Manor neighborhood. This inviting Cape Cod offers timeless charm, modern updates, and a peaceful setting just minutes from downtown Oakland. Many recent improvements including HVAC, water treatment/filtration system, flooring and landscaping! Step inside to an open, light-filled floor plan

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 502-1143

    163 Crestview Dr, Oakland, MD 21550
  • /31

    $745,000 Sold Sep 02, 2025

    • 2,559 Sq Ft
    • $291/SF
    • 16 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2025

    200 Lake Shore Dr, Oakland, MD 21550

    Don’t miss your chance to own a new Gosnell home on the highly sought-after Lake Shore Dr! This spacious 4 bedroom, 4 bathroom home sits on a beautiful wooded one-acre lot, offering privacy, natural surroundings, and easy access to everything the lake has to offer. Every room boasts expansive windows with breathtaking views of the custom landscape design, truly bringing the outdoors in. Designed

    Jonathan Minerick Homecoin.com

    200 Lake Shore Dr, Oakland, MD 21550
    • /24

      Est $191,939 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft

      77 Racoon Dr, Oakland, MD 21550

      77 Racoon Dr, Oakland, MD 21550
  • /9

    $30,000

    • Land
    • 2.71 Acres
    • $11,070 per Acre

    Lot 15 Little Mountain Rd, Oakland, MD 21550

    Welcome to Backbone Ridge, where privacy, natural beauty, and mountain living converge. This 2.71-acre parcel is perfectly situated near the highest point in Maryland, offering breathtaking mountain views and a tranquil, secluded setting.Located in one of the region’s most desirable areas, this property is ready for your dream home. The homesite is already cleared, a gravel driveway in place,

    Agent Photo

    ADAM MURRAY

    BHHS Touchdown Home Pros Realty

    (240) 797-1759

    Lot 15 Little Mountain Rd, Oakland, MD 21550
  • /61

    $820,000 Sold Sep 02, 2025

    • 18 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1990

    939 Glendale Rd, Oakland, MD 21550

    This is the one you've been waiting for—low-maintenance lakefront living at its finest! Boasting one of the most breathtaking views on Deep Creek Lake, this beautifully updated 3-level, 3-bedroom, 3-bath townhome offers “Majestic Views” from every floor. Enjoy a mostly level lakefront with just a few easy steps from your walk-out lower level to the water and dock. Inside, all bathrooms have been

    Sean Sober Taylor Made Deep Creek Vacations & Sales

    939 Glendale Rd, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 18

How to Buy a Home How to Finance a Home How to Sell a Home