190

Homes for Sale in 21550

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  • /46

    $359,000 Coming Soon

    • 3 Beds
    • 3 Baths
    • 1,152 Sq Ft

    552 Black Oak Dr, Oakland, MD 21550

    Looking for a vacation spot or main living, Check out this nicely remolded home in a gated community. 3 bedrooms, 1 1/2 bathrooms, main level laundry room. Great rustic touches . Detached Garage with pellet stove. Yough Mountain Resort is the ultimate mountain escape! Nestled in a quiet, secluded area, this beautifully updated retreat offers modern comfort in a rustic Access to over 50 miles of

    Connie Leprevost Long & Foster Real Estate, Inc.

    552 Black Oak Dr, Oakland, MD 21550
  • /81

    $399,900

    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft

    3930 Mayhew Inn Rd, Oakland, MD 21550

    2 for 1 on 2 .3 +/- acres! Remodeled 2BR 2BA cottage with auxiliary building that has an oversized garage, multiple workshop areas and 1BR 1BA apartment on the second level. New Maryland legislation, Accessory Dwelling Units Act of 2025, will allow expanded access to use the apartment above the garage in a more meaningful manner. Cabin boasts high end finishes and open living space with a cozy

    Jay Ferguson Taylor Made Deep Creek Real Estate

    3930 Mayhew Inn Rd, Oakland, MD 21550
  • /62

    $1,750,000

    • 5 Beds
    • 4 Baths
    • 3,456 Sq Ft

    1544 Stockslager Rd, Oakland, MD 21550

    Enjoy lakefront living at its finest in this beautifully remodeled home with a private dock. Thoughtfully updated with modern finishes including a kitchen remodel, new windows and doors, new upper balcony, new flooring throughout, and recently added mini splits on the lower level. This property offers stunning water views, an open-concept layout, five bedrooms (three of which are en suites), and

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    1544 Stockslager Rd, Oakland, MD 21550
  • /42

    $245,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft

    13 Laurel Brook Dr, Oakland, MD 21550

    Affordable well maintained 2 Bedroom 2 Bath townhouse style condominium less than 1 mile from Deep Creek Lake. Offering low maintenance and a pleasant setting, the property works well for full and part time ownership. The unit offers recent upgrades and Includes 2 parking spaces along with public water, sewer and weekly trash pickup. Shown by appointment only.

    Bill Weissgerber Railey Realty, Inc.

    13 Laurel Brook Dr, Oakland, MD 21550
  • /14

    $165,000

    • Land
    • 0.42 Acre
    • $392,857 per Acre

    Lot 5 Lodestone Way, Sang Run, MD 21541

    Premium lot on the Lodestone Golf Course tucked away in a private nook with just a handful of homes, just minutes from everything there is to love at Deep Creek Lake, sitting on a cul-de-sac! Bring your own builder and floorplan, or use ours! This lot has public water and sewer hookups! High-speed cable/internet! Propane is available for cooking or heat if you'd like! This lot is adjacent to the

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (240) 872-0656

    Lot 5 Lodestone Way, Sang Run, MD 21541
  • /55

    $329,900

    • 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 offers true lakefront living with unbeatable access to everything Deep Creek Lake has to offer. Enjoy effortless days on the water, then relax with on-site amenities including a fitness room, sauna, game room, and expansive lakeside decking. Walk to Dutch’s at Silver Tree, The Harbor Bar, and the marina for dining, drinks,

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 125, Oakland, MD 21550
  • /37

    $125,000

    • Land
    • 0.49 Acre
    • $255,102 per Acre

    Lot 21 Green Jacket Ct, Mc Henry, MD 21541

    Beautiful 1/2 acre LEVEL lot in the Lodestone Village subdivision, minutes from everything there is to love at Deep Creek Lake sitting on a quiet cul-de-sac! Bring your own builder and floorplan, or use ours! This lot has public water and sewer hookups! High-speed cable/internet! Propane is available for cooking or heat if you'd like! This lot is adjacent to the award-winning championship

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (240) 875-4952

    Lot 21 Green Jacket Ct, Mc Henry, MD 21541
  • /50

    $125,000

    • Land
    • 0.54 Acre
    • $231,481 per Acre

    Lot 20 Green Jacket Ct, Mc Henry, MD 21541

    Beautiful 1/2 acre LEVEL lot in the Lodestone Village subdivision, minutes from everything there is to love at Deep Creek Lake sitting on a cul-de-sac! Bring your own builder and floorplan, or use ours! This lot has public water and sewer hookups! High-speed cable/internet! Propane is available for cooking or heat if you'd like! This lot is adjacent to the award-winning championship Lodestone

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (240) 875-5080

    Lot 20 Green Jacket Ct, Mc Henry, MD 21541
  • /48

    $199,900

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

    207 Shenandoah Ave, Oakland, MD 21550

    Fall in love with this charming 2-bedroom, 1-bath home in Loch Lynn, tucked on a 0.25-acre lot with a private wood-fenced side yard and a covered sundeck perfect for morning coffee or evening gatherings. Thoughtfully updated with refinished floors, quartz countertops, new appliances, and cozy touches throughout, it’s move-in ready and effortlessly welcoming. Enjoy modern convenience with a smart

    Laura Newhall Taylor Made Deep Creek Real Estate

    207 Shenandoah Ave, Oakland, MD 21550
  • /78

    $689,000

    • 3 Beds
    • 3.5 Baths
    • 2,670 Sq Ft

    276 Sundance Way, Mc Henry, MD 21541

    276 Sundance Way – a 3BR, 3.5BA Mountaineer Log Home built in 2018, set along Hole 6 of Lodestone Golf Course with a private, wooded backyard. The main level features an open kitchen, dining, and living area centered around a large island, along with a primary bedroom, laundry room, and half bath off the entry. Upstairs offers a large loft, two spacious bedrooms, and a full bathroom, giving

    Kelsey Meyers Railey Realty, Inc.

    276 Sundance Way, Mc Henry, MD 21541
  • /37

    $219,000

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    407 Seneca Ave, Oakland, MD 21550

    Move right into this charming ranch style home offering comfortable one-level living! Recent improvements include a brand-new roof and fresh carpet throughout, giving the home a clean, updated feel. Offering three bedrooms and a wood burning fireplace which just adds to the warmth and coziness. The level yard provides great space for relaxing and entertaining family and friends. The location is

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    407 Seneca Ave, Oakland, MD 21550
  • /69

    $2,100,000

    • 5 Beds
    • 5 Baths
    • 4,074 Sq Ft

    1038 S Blakeslee Rd, Oakland, MD 21550

    Welcome to 1038 S Blakeslee Road! A spacious lakefront retreat on Deep Creek Lake offering effortless lakeside living. A Rare opportunity to own in one of Deep Creek’s most sought-after lakeside communities. This five-bedroom, five-bath home sits on a large 1.11-acre level lot with easy access to the water and generous outdoor space for recreation and entertaining. Inside, the home is warm and

    Eric Crawford Taylor Made Deep Creek Real Estate

    1038 S Blakeslee Rd, Oakland, MD 21550
  • /30

    $159,000

    • 1 Bed
    • 1 Bath
    • 382 Sq Ft

    565 Glendale Rd Unit 124, Oakland, MD 21550

    Public: If you are looking for an affordable way to own at Deep Creek Lake, this is it! This Silver Tree Suites unit is is main floor and beautiful. .Offering a king size bed, and a propane fireplace. The hotel offers a sitting area, sauna and workout area for your enjoyment. The Dutch's restaurant & Harbor Bar are just steps away, offering wonderful dining options while never having to leave the

    ANGELA BOSLEY Taylor Made Deep Creek Real Estate

    565 Glendale Rd Unit 124, Oakland, MD 21550
  • /23

    $69,000

    • Land
    • 0.57 Acre
    • $121,053 per Acre

    Lot 79 Sundance Way, McHenry, MD 21541

    0.57 acre mountaintop homesite at Deep Creek Lake! Competitively priced and ready to build. This property offers location just minutes from Wisp, ASCI and all of Deep Creek Lake's amenities with a private feel towards the end of the cup-de-sac. Public water and sewer taps are paid, providing several thousand dollars in savings for a purchaser. Electricity is to site. The only thing missing is

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 650-9125

    Lot 79 Sundance Way, McHenry, MD 21541
  • /13

    $29,999

    • Land
    • 1.93 Acres
    • $15,544 per Acre

    0 Cub Dr, Oakland, MD 21550

    Make an offer, buy it now. +/- 1.93 Acre lot of land in Garrett County. Close to the West Virginia Border. Easy access to major traffic artery Cranesville Rd. Parcel is vacant.

    Adam Shpritz

    0 Cub Dr, Oakland, MD 21550
  • /19

    $89,900

    • Land
    • 1 Acre
    • $89,900 per Acre

    36 Fern Loop, Sang Run, MD 21541

    1.00 acre building lot in Sandy Shores Heights at Wisp Mountain Resort. Centrally located just minutes from Local Restaurants, State Parks, Wisp Resort and Deep Creek Lake! Public utilities to site. Strong location & ready for your plans!

    Jon Bell Railey Realty, Inc.

    36 Fern Loop, Sang Run, MD 21541
  • /2

    $5,000

    • 3 Beds
    • 2 Baths
    • 1,539 Sq Ft

    610 Harvey Winters Dr, Other, FL 21550

    Foreclosure Auction Ends April 01, 2026 at 01:00 PM EST. Discover this inviting 3-bedroom, 2-bathroom single-family home, offering a great opportunity in a desirable Oakland community. The list price is the opening bid for the online auction. Sold As-is. Explore more details and submit your bid through Federa.

    Jamie Boone Jamie L Boone LLC

    610 Harvey Winters Dr, Other, FL 21550
  • /75

    $885,000

    • 4 Beds
    • 4 Baths
    • 3,007 Sq Ft

    93 Kendall Camp Cir, Mc Henry, MD 21541

    Experience the ultimate mountain getaway at 93 Kendall Camp Circle in McHenry! This sought-after ski-in/ski-out duplex offers direct access to Chair Lift #4 at Wisp Resort—making it a dream location for winter enthusiasts. Step inside to find a warm and inviting interior featuring a wood-burning fireplace—perfect for unwinding after a day on the slopes. Offering over 3000 square feet with 4

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 594-9432

    93 Kendall Camp Cir, Mc Henry, MD 21541
  • /67

    $525,000

    • 2 Beds
    • 2 Baths
    • 4,720 Sq Ft

    355 Lonesome Pine Rd, Oakland, MD 21550

    Welcome to your own slice of paradise—this stunning home sits on 84 breathtaking acres with incredible water frontage, offering unmatched privacy and a true connection to nature. Step inside and be captivated by walls of windows that flood the home with natural light, creating a warm and inviting atmosphere throughout the expansive living spaces. Whether you're entertaining or simply relaxing,

    Sheila Howell Lake Homes Realty, LLC

    355 Lonesome Pine Rd, Oakland, MD 21550
  • /61

    $379,000

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

    1167 Tall Oaks Dr, Oakland, MD 21550

    Picture perfect log cabin on 11 private, wooded acres in the gated Timbers on the Yough community featuring Youghiogheny River access. This inviting home features a metal roof, spacious covered deck, newly installed walkway, exterior fire pit, breakfast bar, and pellet stove. The primary bath offers dual sinks, an oversized soaking tub, dual shower heads and radiant floor heat!Recent updates

    Kellyann Green Railey Realty, Inc.

    1167 Tall Oaks Dr, Oakland, MD 21550
  • /3

    $875,000 Coming Soon

    • 3 Beds
    • 4 Baths
    • 3,990 Sq Ft

    891 Mountainview Dr, Oakland, MD 21550

    Discover the perfect blend of rustic charm and modern comfort in this inviting turnkey 3‐bedroom mountaintop chalet, set on 1.17 private acres with expansive outdoor entertainment space. Whether you're hosting friends or enjoying quiet mountain evenings, this fully-furnished home delivers an unforgettable retreat. Inside, the great room impresses with a soaring stacked‐stone fireplace. The

    Brent Housley Railey Realty, Inc.

    891 Mountainview Dr, Oakland, MD 21550
  • /8

    $25,000

    • Land
    • 3 Acres
    • $8,333 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
  • /66

    $950,000

    • 4 Beds
    • 3.5 Baths
    • 3,566 Sq Ft

    110 Highline Dr, Mc Henry, MD 21541

    Take a look at this awesome chalet style home with stunning lake and mountain views. Featuring 4 bedrooms and 3.5 baths, this home is perfect for entertaining. This ski-in and ski-out property is located in the highly coveted Highline community that sits very close to the Wisp Ski Area and ASCI. Two fireplaces, one in the main level living room and one in the lower level recreation room. Main

    Kevin Liller Railey Realty, Inc.

    110 Highline Dr, Mc Henry, MD 21541
  • /10

    $99,900

    • Land
    • 1.7 Acres
    • $58,765 per Acre

    0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550

    Ready to bring your Deep Creek Lake dream home to life? This beautiful 1.7-acre lot in the sought after community of Paradise Ridge offers the perfect blend of peace, privacy, and lake access. Spend your summer days down by the water, where owners enjoy access to one of the area’s best lakefront spots, complete with a sandy beach, picnic pavilions, and kayak or swimming areas. When the day winds

    Eric Crawford Taylor Made Deep Creek Real Estate

    0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550
  • /19

    $289,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    226 N Hammond St, Oakland, MD 21550

    NEW CONSTRUCTION from Lyv Homes! This 2BR/2BA, 1000sf cottage is located in the historic 2nd Street area of Oakland and features modern design with elite finishes. Key features include Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets and drawers, quartz counters and range backsplash, shiplap backsplash accents, stainless steel Frigidaire

    Jay Ferguson Taylor Made Deep Creek Real Estate

    226 N Hammond St, Oakland, MD 21550
  • /62

    $314,000

    • 3 Beds
    • 2.5 Baths
    • 2,242 Sq Ft

    163 Mitchell Dr, Oakland, MD 21550

    Nestled in the charming Mitchell Manor community, this delightful split-level home offers a perfect blend of comfort and style. With 2,242 square feet of thoughtfully designed living space, this residence features three spacious bedrooms and two and a half bathrooms, ideal for both relaxation and entertaining. There is also a walk-in closet/dressing room to die for! Step inside to discover an

    Andrew Eiswert Railey Realty, Inc.

    163 Mitchell Dr, Oakland, MD 21550
  • /43

    $555,000

    • 4 Beds
    • 3.5 Baths
    • 2,430 Sq Ft

    24 Trailside Way, Oakland, MD 21550

    Tucked in the Silver Ridge community at Deep Creek Lake, this inviting home blends rustic charm with comfortable modern living. Community trails and shared green space offer opportunities for outdoor recreation, while the wooded setting behind the home provides a sense of privacy and a peaceful natural backdrop. Step inside to an interior that reflects its surroundings, where warm wood accents,

    Jackie Ball Daley Northrop Realty

    24 Trailside Way, Oakland, MD 21550
  • /20

    $160,000

    • Land
    • 10.1 Acres
    • $15,842 per Acre

    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550

    Over 10 acres ready for developing off Dennett Rd. and Oakland Ave. Can be subdivided or could be large parcel to build your dream home, privacy off main streets with 3 separate entrances connecting to town roads. Engineered drawings for subdivision with grading permit in place at time of survey, is available and will be transferred with sale. (Potential up to 20 lots) Public sewar & water can be

    Julie Mead The KW Collective

    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550
  • /22

    $207,500

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft

    1307 Broadford Rd, Oakland, MD 21550

    Nestled in the scenic countryside of Oakland, this charming ready to move in 2 bed 1 Bath home offers the perfect blend of privacy, space, and small-town convenience. Situated on a beautiful property along Broadford Road, the home provides peaceful surroundings while remaining just minutes from downtown Oakland, schools, shopping, and plenty of outdoor recreation areas.. Properties in this area

    Bill Kenny Keller Williams Realty Centre

    1307 Broadford Rd, Oakland, MD 21550
  • /64

    $275,900

    • 4 Beds
    • 2 Baths
    • 1,928 Sq Ft

    449 S 3rd St, Oakland, MD 21550

    Welcome to this beautifully updated 1901 home in the heart of downtown Oakland, where historic character meets modern convenience. Situated on a charming lot with mature landscaping and blooming trees, this home offers timeless curb appeal with a welcoming covered front porch perfect for relaxing and enjoying the neighborhood. Inside, you’ll find modern updates throughout while preserving classic

    Justin Liller Railey Realty, Inc.

    449 S 3rd St, Oakland, MD 21550
  • /43

    $325,000

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

    3749 Maryland Hwy, Oakland, MD 21550

    Set on a beautiful lot in Deep Creek, Maryland, this stunning property offers the perfect blend of privacy, relaxation, and investment potential. Currently enjoyed as a second home, the residence has also been successfully utilized as a partial Airbnb, generating approximately $28,000 in rental income last year. The home has been thoughtfully updated, creating a warm and inviting atmosphere with

    Jovan Vidulovic Keller Williams Realty

    3749 Maryland Hwy, Oakland, MD 21550
  • /34

    $239,700

    • 3 Beds
    • 3 Baths
    • 1,104 Sq Ft

    53 Bird Ave, Oakland, MD 21550

    Opportunity and a peaceful country setting on 1.55 acres in Deer Park. This 3BR, 2BA ranch offers 1,872 sq ft with solid bones and room to make it your own. The spacious kitchen with hickory cabinets, gas stove, and propane fireplace creates a warm gathering space at the heart of the home. Outside, several outbuildings—including a large shop and secondary wood shop with heat and electric, a

    Rachel Bruch Railey Realty, Inc.

    53 Bird Ave, Oakland, MD 21550
  • /57

    $219,000

    • 1 Bed
    • 1.5 Baths
    • 912 Sq Ft

    141 Montana Ln, Oakland, MD 21550

    Nestled on nearly 3 acres across two parcels, this chalet-style home offers a rare opportunity to create your retreat just minutes from the lake. Renovate the existing structure, or start fresh and build the lake-area retreat or cabin you’ve always imagined. The level, wooded setting provides privacy, peace, and plenty of room to expand, garden, or simply enjoy nature. With well and septic

    Larry Smith Railey Realty, Inc.

    141 Montana Ln, Oakland, MD 21550
  • /50

    $950,000

    • 3 Beds
    • 2.5 Baths
    • 2,368 Sq Ft

    164 Grandview Dr, Oakland, MD 21550

    Experience mountain living at its finest in this breathtaking mountaintop home overlooking Deep Creek Lake. With sweeping views from almost every room, your hardest decision may be where to sit to enjoy them. Offering three levels of living space, hardwood floors ( which were recently refinished), and some new appliances. The multiple decks are ideal to enjoy family and friends while taking in

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    164 Grandview Dr, Oakland, MD 21550
  • /2

    $69,900

    • 3 Beds
    • 1 Bath
    • 792 Sq Ft

    74 Parks Rd, Oakland, MD 21550

    **Investor Special with Mountain & Water Views**Opportunity is knocking at 74 Parks Road in Oakland, Maryland! This 3-bedroom, 1-bath one story is perfectly positioned just steps from the West Virginia line and surrounded by some of the most sought-after recreation in the region.Enjoy peaceful views of Snowy Creek right from the front yard and take advantage of being just minutes from

    Emillie Albrecht Real Broker, LLC

    74 Parks Rd, Oakland, MD 21550
  • /28

    $299,000

    • 2 Beds
    • 1 Bath
    • 550 Sq Ft

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550

    Nestled in the charming Traders Landing community, this delightful end-of-row townhouse offers a perfect blend of comfort and convenience with one of the best unobstructed views of the lake in Traders Landing. This villa-style home features two cozy bedrooms and a full bathroom, ideal for relaxation and unwinding after a long day. The inviting living space is enhanced by a warm wood-burning

    Agent Photo

    James Matthews

    Taylor Made Deep Creek Real Estate

    (240) 883-5848

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
  • /17

    $35,000

    • Land
    • 1.92 Acres
    • $18,229 per Acre

    233 Rhododendron Dr, Oakland, MD 21550

    Fantastic opportunity in the gated community of Youghiogheny Mountain Resort. This 1.92-acre lot is perfect for outdoor enthusiasts, offering ATV riding, hunting, fishing, and more. Build your dream home or a recreational retreat. Approved for a 2-bedroom conventional system, with the option to expand using a sand mound system. Located just minutes from Wisp Resort, Deep Creek Lake, Herrington

    Laura Newhall Taylor Made Deep Creek Real Estate

    233 Rhododendron Dr, Oakland, MD 21550
  • /17

    $449,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    654 N Bradley Ln, Oakland, MD 21550

    NEW CONSTRUCTION from Lyv Homes! 3BR/2BA, 1464sf contemporary style home fronting on the 13th hole of the Oakland golf course. This property combines MAJESTIC scenic views with modern design, elite finishes and outdoor living. Key features include multiple wood-burning fireplaces (inside + out), Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets

    Jay Ferguson Taylor Made Deep Creek Real Estate

    654 N Bradley Ln, Oakland, MD 21550
  • /38

    $297,500

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    505 Southern Pines Dr, Oakland, MD 21550

    Charming ranch-style home located in the desirable Southern Pines neighborhood. From the moment you enter, you’ll appreciate the warm and inviting feel of the open layout. The main level features three comfortable bedrooms, two full bathrooms, beautiful hardwood flooring, and a seamless kitchen, living, and dining area that creates an ideal space for everyday living and entertaining. The recently

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    505 Southern Pines Dr, Oakland, MD 21550
  • /19

    $60,000

    • 2 Beds
    • 1 Bath
    • 782 Sq Ft

    820 N 4th St, Oakland, MD 21550

    Step into potential with this 2 bed, 1 bath home being sold AS IS. Located in a convenient community with town water & sewer, this property offers a blank canvas for the savvy buyer or investor ready to bring a vision to life. The house has been gutted and is ready for the new owner to start the renovation, providing a clear interior and a fresh slate to customize the layout, finishes, and

    Duane Stein II The KW Collective

    820 N 4th St, Oakland, MD 21550

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