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Oakland, MD Homes for Sale with Garage

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  • 127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    /60

    $275,000

    • 4 Beds
    • 2 Baths
    • 1,913 Sq Ft

    127 S Oakhall Dr, Oakland, MD 21550

    Welcome to this well maintained 4-bed, 2-bath ranch home on a generous corner lot in Oakland, MD. Inviting curb appeal with stone exterior and mature landscaping sets the tone. Step inside to a bright and spacious main level featuring gleaming hardwood floors, a large eat-in kitchen with ample cabinetry, and an open living area perfect for gatherings. Enjoy three main-level bedrooms and a full

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 792-8710

    127 S Oakhall Dr, Oakland, MD 21550
  • 47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    /109

    $6,499,900

    • 8 Beds
    • 8.5 Baths
    • 11,417 Sq Ft

    47 Holy Cross Cir, Oakland, MD 21550

    Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with

    Jon Bell Railey Realty, Inc.

    47 Holy Cross Cir, Oakland, MD 21550
  • 163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    /62

    $289,000

    • 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
  • 439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    /45

    $1,329,000

    • 6 Beds
    • 4.5 Baths
    • 4,113 Sq Ft

    439 Paradise Heights, Oakland, MD 21550

    Stunning 6-Bedroom Kathadin Log Home with Breathtaking 180 views of Deep Creek Lake with Lake Access and a Boat Slip! This exceptional vacation home offers the perfect blend of rustic charm and modern luxury. Boasting 180-degree panoramic views of the sparkling lake, this property is a true mountain retreat. Every room is designed to capture the beauty of the surrounding landscape, with expansive

    Mike Kennedy Railey Realty, Inc.

    439 Paradise Heights, Oakland, MD 21550
  • 130 Mystic Creek Trail Unit 1B, Oakland, MD 21550
    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550
    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550
    /69

    $639,000

    • 5 Beds
    • 4.5 Baths
    • 2,200 Sq Ft

    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550

    Discover refined mountain and lake living in this quality built townhome at Mystic Creek on Deep Creek Lake, nestled in a quiet, serene setting with a truly custom feel. This spacious 5-bedroom, 4.5 bath residence offers an open concept main level ideal for entertaining, featuring hardwood floors throughout the main living area, abundant natural light, and seamless flow between the living,

    Melissa Long Railey Realty, Inc.

    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550
  • 20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    /68

    $575,000

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

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550

    Lakefront living at it's best can be found in this completely renovated spacious condo. This three-level unit is the perfect place to get away together! With space to come together and space to escape, this unit promises both privacy and togetherness for a memorable Deep Creek Lake experience! The first level has a full kitchen with wine fridge and attached living room with an electric fireplace,

    Kevin Liller Railey Realty, Inc.

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
  • 5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    /67

    $399,000

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    5024 Cranesville Rd, Oakland, MD 21550

    Just Reduced!! Charming 3-Bedroom Home with Scenic Mountain & Valley Views. Nestled on a 1.68-acre hillside in a beautiful conservation area, this 3-bedroom, 2.5-bath home combines natural charm with modern comfort. The native stone exterior and peaceful setting set the tone for this inviting residence.Inside, the main level features a spacious primary suite with a jetted tub, double vanity,

    Rich Orr Railey Realty, Inc.

    5024 Cranesville Rd, Oakland, MD 21550
  • 328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    /123

    $545,000

    • 4 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    328 Stool Rock Rd, Oakland, MD 21550

    Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of craftsmanship featuring handmade woodwork crafted from trees sourced directly from the property. Many specialty items will remain, including bathroom vanities, multiple dressers, a primary suite custom TV console, a built-in bunk bed, and more. The spacious primary suite was added in 2016 and offers a separate

    Kathy Gibson Railey Realty, Inc.

    328 Stool Rock Rd, Oakland, MD 21550
  • 1010 Holy Cross Dr, Oakland, MD 21550
    1010 Holy Cross Dr, Oakland, MD 21550
    1010 Holy Cross Dr, Oakland, MD 21550
    /147

    $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 Reserve at

    Rachel Bruch Railey Realty, Inc.

    1010 Holy Cross Dr, Oakland, MD 21550
  • 222 Skippers Point Rd, Oakland, MD 21550
    222 Skippers Point Rd, Oakland, MD 21550
    222 Skippers Point Rd, Oakland, MD 21550
    /56

    $779,000

    • 5 Beds
    • 1.5 Baths
    • 1,278 Sq Ft

    222 Skippers Point Rd, Oakland, MD 21550

    Lake cottage on large level lot with path to your own private class A dock & 25' of Lakefront, directly across the street. This comfy (one level living) cottage sits on 1.8 level acres with 2 storage garages and mature landscaping. 5BRs, open living, dinning & kitchen area, with lots of sunlight. 1 full & 1-1/2 bath, with 5 Bedrooms! Laundry room located off back of the home. Cute and cozy, well

    Julie Mead The KW Collective

    222 Skippers Point Rd, Oakland, MD 21550
  • 126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    /50

    $529,900

    • 4 Beds
    • 3 Baths
    • 2,235 Sq Ft

    126 Leo Friend Rd, Oakland, MD 21550

    Perched above the treetops with panoramic lake views, this three-level retreat blends comfort with clean, considered upgrades. Vaulted ceilings and a spacious loft crown 2,235 square feet of living space, wrapped in new flooring with fresh paint inside and out. The kitchen, smartly updated with new countertops, connects to open dining and living anchored by a wood stove. A detached garage sits

    Jon Bell Railey Realty, Inc.

    126 Leo Friend Rd, Oakland, MD 21550
  • 312 Moss Creek Cir, Oakland, MD 21550
    312 Moss Creek Cir, Oakland, MD 21550
    312 Moss Creek Cir, Oakland, MD 21550
    /10

    $795,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 4,230 Sq Ft

    312 Moss Creek Cir, Oakland, MD 21550

    Tucked away on a picturesque 1.83-acre parcel, this charming log home offers the perfect blend of rustic character and modern comfort. Amongst the 4,200+ SF, you will find five spacious bedrooms, two family rooms, a playroom, an office/den, a large loft, spacious pantry, granite counter tops, hardwood flooring and two fireplaces. The warm wood interior and classic log construction create a cozy,

    Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    312 Moss Creek Cir, Oakland, MD 21550
  • 620 Crosby Dr, Oakland, MD 21550
    620 Crosby Dr, Oakland, MD 21550
    620 Crosby Dr, Oakland, MD 21550
    /62

    $699,900

    • 4 Beds
    • 3.5 Baths
    • 3,420 Sq Ft

    620 Crosby Dr, Oakland, MD 21550

    This stunning, recently built 4+ bedroom, 3.5 bath home in Country Club Acres offers modern design, thoughtful upgrades, and unmatched privacy on 3.43 wooded acres perched at the top of the mountain overlooking Oakland Golf Course and multiple ponds. The bright, open-concept layout is filled with natural light and features commercial-grade LVP flooring throughout, complemented by mid-range,

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    620 Crosby Dr, Oakland, MD 21550
  • 1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    /62

    $735,000

    • 5 Beds
    • 5 Baths
    • 3,664 Sq Ft

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    Check out this beautifully built and maintained 5 bedroom 5 bathroom lake area chalet style home. Located on the Southern side of the lake, near the headwaters of Deep Creek. The namesake stream that feeds into the nearby lake. This property offers it's new owners a tremendous amount of room for storage and entertaining and three levels of finished living space. The top floor is designed as an

    Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • 267 San Francisco St, Oakland, MD 21550
    267 San Francisco St, Oakland, MD 21550
    267 San Francisco St, Oakland, MD 21550
    /30

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 3,278 Sq Ft

    267 San Francisco St, Oakland, MD 21550

    Welcome to your secluded Deep Creek retreat! This stunning property offers expansive lake views! So clear you’ll catch the slopes of Wisp in the distance. Includes 3 lots and the privacy is unmatched. This house was torn down to the foundation and a new house was built in 2009. Inside, you’ll find four spacious bedrooms, two and a half baths, and soaring vaulted ceilings and a grand fireplace.

    Bradley West HomeSmart

    267 San Francisco St, Oakland, MD 21550
  • 3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    /31

    $1,650,000

    • 4 Beds
    • 6 Baths
    • 5,117 Sq Ft

    3898 Underwood Rd, Oakland, MD 21550

    Unique luxury home on 23 acres with 360 degree views of Pleasant Valley. 5,100 + SQ. FT. 4 ensuite bedrooms, 2 additional powder rooms, formal living room/ballroom, informal living room, sunroom, den, pantry and large dine in kitchen. 4 fireplaces. full basement, 3 car attached garage. Whole home generator. Everything in this home is first rate. A must see for the discerning buyer

    Robert Custer Custer Realty & Auction

    3898 Underwood Rd, Oakland, MD 21550
  • 4A Mystic Creek Trail, Oakland, MD 21550
    4A Mystic Creek Trail, Oakland, MD 21550
    4A Mystic Creek Trail, Oakland, MD 21550
    /50

    $679,900 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    4A Mystic Creek Trail, Oakland, MD 21550

    Discover refined mountain-lake living in this new construction townhome at Mystic Creek on Deep Creek Lake. Designed with today’s lifestyle in mind, the home features a modern open-concept main level ideal for entertaining, with clean lines, abundant natural light, and seamless flow between living, dining, and kitchen spaces. This spacious residence offers three primary suites, each with upscale

    Justin Liller Railey Realty, Inc.

    4A Mystic Creek Trail, Oakland, MD 21550
  • 3930 Mayhew Inn Rd, Oakland, MD 21550
    3930 Mayhew Inn Rd, Oakland, MD 21550
    3930 Mayhew Inn Rd, 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, LLC

    3930 Mayhew Inn Rd, Oakland, MD 21550
  • 206 Mayhew Inn Rd, Oakland, MD 21550
    206 Mayhew Inn Rd, Oakland, MD 21550
    206 Mayhew Inn Rd, Oakland, MD 21550
    /31

    $224,900

    • 1 Bed
    • 1 Bath
    • 1,080 Sq Ft

    206 Mayhew Inn Rd, Oakland, MD 21550

    Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath house blends cozy living with endless potential. The upper level offers a cozy living area, a full kitchen, laundry room, bedroom, and full bath. But the real bonus? A spacious 2-car garage with its own entrance. It is perfect for a workshop, extra storage, or even a rental opportunity. With separate

    Jay Quinn Taylor-Made Deep Creek Real Estate, LLC

    206 Mayhew Inn Rd, Oakland, MD 21550
  • 729 E Oak St, Oakland, MD 21550
    729 E Oak St, Oakland, MD 21550
    729 E Oak St, Oakland, MD 21550
    /61

    $185,000

    • 3 Beds
    • 1.5 Baths
    • 1,170 Sq Ft

    729 E Oak St, Oakland, MD 21550

    Great, affordable starter home located in Oakland with public water and sewer, one car detached garage, hot water natural gas heat. Two bedroom and full bath on second level and possible third bedroom on main level with 1/2 bath. Cellar basement with mechanicals. Washer and Dryer hookups, washer/dryer convey, are located on the back enclosed porch which has electric baseboard heat. Enclosed front

    Kevin Liller Railey Realty, Inc.

    729 E Oak St, Oakland, MD 21550
  • 17921 Garrett Hwy, Oakland, MD 21550
    17921 Garrett Hwy, Oakland, MD 21550
    17921 Garrett Hwy, Oakland, MD 21550
    /14

    $359,000

    • 4 Beds
    • 1.5 Baths
    • 1,563 Sq Ft

    17921 Garrett Hwy, Oakland, MD 21550

    Charming and well-maintained, this 4-bedroom, 1.5-bath traditional home offers the perfect combination of comfort, character, and convenience. Built in 1952 and thoughtfully cared for, the home features beautifully refinished hardwood floors, inviting built-ins, and a cozy living room with a functional wood burner. With over 1,500 square feet of living space, the spacious layout includes an

    Michelle Clark Taylor-Made Deep Creek Real Estate, LLC

    17921 Garrett Hwy, Oakland, MD 21550
  • 552 Black Oak Dr, Oakland, MD 21550
    552 Black Oak Dr, Oakland, MD 21550
    552 Black Oak Dr, Oakland, MD 21550
    /46

    $359,000

    • 3 Beds
    • 1.5 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
  • 321 N 3rd St, Oakland, MD 21550
    321 N 3rd St, Oakland, MD 21550
    321 N 3rd St, Oakland, MD 21550
    /5

    $400,000 Open Sat 10AM - 12PM

    • 5 Beds
    • 2 Baths
    • 3,660 Sq Ft

    321 N 3rd St, Oakland, MD 21550

    Professional photos coming soon. Spacious and beautifully maintained all-brick rancher offering approximately 3,660 square feet of living space with room for everyone! This impressive home features 5 bedrooms, 2 full bathrooms, and a fully finished basement with its own private entrance—perfect for in-law potential, extended family living, or flexible multi-generational use. Inside, you’ll find a

    Christina Ford CENTURY 21 New Millennium

    321 N 3rd St, Oakland, MD 21550
  • 2725 Stockslager Rd, Oakland, MD 21550
    2725 Stockslager Rd, Oakland, MD 21550
    2725 Stockslager Rd, Oakland, MD 21550
    /115

    $2,350,000

    • 5 Beds
    • 6.5 Baths
    • 5,376 Sq Ft

    2725 Stockslager Rd, Oakland, MD 21550

    Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This custom-built log home is set against a picturesque landscape in Western Maryland, offering breathtaking nature views and embodying mountain charm and adventure. This home showcases impeccable craftsmanship, seamlessly blending with its natural surroundings while providing unrivaled comfort. Nestled on 1.03

    Shelia McCracken Taylor-Made Deep Creek Real Estate, LLC

    2725 Stockslager Rd, Oakland, MD 21550
  • 961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    /50

    $339,000

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

    961 Cedar Ln, Oakland, MD 21550

    Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat offers privacy, comfort, and plenty of space to unwind. Step inside to find a warm and inviting main level highlighted by a stone fireplace, cozy dining area, and galley-style kitchen. Relax on the screened-in porch complete with a hot tub under roof, perfect for year-round enjoyment. The finished basement

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    961 Cedar Ln, Oakland, MD 21550
  • 178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    /47

    $589,000

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

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550

    Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lake has to offer, Whispering Pines is the ultimate turnkey mountain retreat. This impeccably maintained 5-bedroom townhome spans three levels of inviting living space and features an attached garage—perfect for hosting family, friends, or guests year-round. Enjoy the best of both worlds: a private, serene

    Nina Beitzel Railey Realty, Inc.

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
  • 215 H St, Oakland, MD 21550
    215 H St, Oakland, MD 21550
    215 H St, Oakland, MD 21550
    /55

    $379,000

    • 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
  • 931 Black Oak Dr, Oakland, MD 21550
    931 Black Oak Dr, Oakland, MD 21550
    931 Black Oak Dr, Oakland, MD 21550
    /53

    $349,999 Open Sat 10AM - 12PM

    • 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
  • 467 Paradise Ridge Rd, Oakland, MD 21550
    467 Paradise Ridge Rd, Oakland, MD 21550
    467 Paradise Ridge Rd, Oakland, MD 21550
    /60

    $799,900

    • 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
  • 1740 Old Crellin Rd, Oakland, MD 21550
    1740 Old Crellin Rd, Oakland, MD 21550
    1740 Old Crellin Rd, Oakland, MD 21550
    /28

    $335,000

    • 3 Beds
    • 3 Baths
    • 2,288 Sq Ft

    1740 Old Crellin Rd, Oakland, MD 21550

    Come see this beautifully maintained 3-bedroom, 3-bath Colonial-style residence nestled on a private 1-acre lot along Old Crellin Road in Oakland. Offering 2,300 square feet of living space, this home combines classic charm with modern comfort in an ideal location just outside town limits. Step inside to find a spacious and inviting layout, perfect for both everyday living and entertaining. The

    Andrew Orr The KW Collective

    1740 Old Crellin Rd, Oakland, MD 21550
  • 104 Pine Top Trail, Oakland, MD 21550
    104 Pine Top Trail, Oakland, MD 21550
    104 Pine Top Trail, Oakland, MD 21550
    /13

    $425,000

    • 3 Beds
    • 3.5 Baths
    • 1,596 Sq Ft

    104 Pine Top Trail, Oakland, MD 21550

    Here's your chance to purchase a cute Chalet with just about 7 acres. .This home and acreage is right next to the Common Grounds and gives you immediate river access.

    laura Flynn 1 Real Estate Source LLC

    104 Pine Top Trail, Oakland, MD 21550
  • 891 Mountainview Dr, Oakland, MD 21550
    891 Mountainview Dr, Oakland, MD 21550
    891 Mountainview Dr, Oakland, MD 21550
    /82

    $875,000

    • 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 with lake access, 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

    Brent Housley Railey Realty, Inc.

    891 Mountainview Dr, Oakland, MD 21550
  • 3749 Maryland Hwy, Oakland, MD 21550
    3749 Maryland Hwy, Oakland, MD 21550
    3749 Maryland Hwy, Oakland, MD 21550
    /43

    $299,900

    • 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
  • 170 Cherrywood Dr, Oakland, MD 21550
    170 Cherrywood Dr, Oakland, MD 21550
    170 Cherrywood Dr, Oakland, MD 21550
    /67

    $699,000

    • 5 Beds
    • 3 Baths
    • 2,560 Sq Ft

    170 Cherrywood Dr, Oakland, MD 21550

    4/5BR 3BA custom home (3900+ total sf!) on 8+ acres of peaceful tranquility! Conveys with 2 lots (6 & 7) totaling 8.05 acres of wooded land in a laid back HOA that allows chickens & embraces the outdoor amenities Garrett County offers. Private and secluded rural location that is just minutes from town, schools, shopping and dining. This home was custom designed for work from home professionals -

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    170 Cherrywood Dr, Oakland, MD 21550
  • 127 Paradise Heights, Oakland, MD 21550
    127 Paradise Heights, Oakland, MD 21550
    127 Paradise Heights, Oakland, MD 21550
    /24

    $1,075,000

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    127 Paradise Heights, Oakland, MD 21550

    Beautifully renovated lake access log cabin with a deeded dock slip in a quiet cove with private 29 acres of trails (ATVs/snowmobiles permitted). Recent renovations (approx. $200K) include new wrap around deck, new roof, re-stained siding, new kitchen with granite counters, new appliances, new bathrooms, new LVFs throughout the house, new 2 car garage doors, new mini-split heat and A/C units, and

    Norman Domingo XRealty.NET LLC

    127 Paradise Heights, Oakland, MD 21550
  • 827 Penn Point Rd, Oakland, MD 21550
    827 Penn Point Rd, Oakland, MD 21550
    827 Penn Point Rd, Oakland, MD 21550
    /64

    $1,400,000

    • 5 Beds
    • 3.5 Baths
    • 2,832 Sq Ft

    827 Penn Point Rd, Oakland, MD 21550

    Custom built by the original owners and thoughtfully expanded with a recent addition, this exceptional five-bedroom, 3.5-bath home is set on 100 feet of split lakefront in desirable Penn Cove. Featuring a coveted Type A dock permit, lakeside fire pit and pavilion, and easy shoreline access, the property is designed to embrace lake living in every season. Set on a generously sized lot with

    Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    827 Penn Point Rd, Oakland, MD 21550
  • 1909 Pysell Crosscut Rd, Oakland, MD 21550
    1909 Pysell Crosscut Rd, Oakland, MD 21550
    1909 Pysell Crosscut Rd, Oakland, MD 21550
    /82

    $825,000

    • 4 Beds
    • 4.5 Baths
    • 2,970 Sq Ft

    1909 Pysell Crosscut Rd, Oakland, MD 21550

    Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just minutes from Deep Creek Lake and Oakland. This 4-bedroom, 4.5-bath home has been carefully updated to balance comfort, practicality, and modern style. The main level features hardwood floors, radiant heat for added comfort, and open gathering spaces with quiet nooks for reading or hobbies. Upstairs, two

    Melissa Long Railey Realty, Inc.

    1909 Pysell Crosscut Rd, Oakland, MD 21550
  • 63 Wallman Rd, Oakland, MD 21550
    63 Wallman Rd, Oakland, MD 21550
    63 Wallman Rd, Oakland, MD 21550
    /60

    $174,900

    • 3 Beds
    • 1 Bath
    • 816 Sq Ft

    63 Wallman Rd, Oakland, MD 21550

    Remodeled Rancher Near the North Branch Potomac RiverThis charming 3-bedroom, 1-bath rancher has been completely remodeled, with all new appliances. Located within walking distance of the scenic North Branch of the Potomac River, the home offers both convenience and natural beauty at your doorstep.A recently enclosed front porch with a wood stove provides extra warmth and a welcoming spot

    Rich Orr Railey Realty, Inc.

    63 Wallman Rd, Oakland, MD 21550
  • 62 Whispering Pines Ln, Oakland, MD 21550
    62 Whispering Pines Ln, Oakland, MD 21550
    62 Whispering Pines Ln, Oakland, MD 21550
    /77

    $899,000

    • 4 Beds
    • 3.5 Baths
    • 2,464 Sq Ft

    62 Whispering Pines Ln, Oakland, MD 21550

    Tucked away on just over 7 acres of serene, wooded privacy, this stunning custom Yellowstone log home offers the perfect blend of rustic charm and modern comfort—just minutes from Swallow Falls State Park and only 10 minutes to Deep Creek Lake and Wisp Resort. The inviting open main level is designed for effortless entertaining, highlighted by a warm gas fireplace in the family room, a spacious

    Justin Liller Railey Realty, Inc.

    62 Whispering Pines Ln, Oakland, MD 21550
  • 407 Seneca Ave, Oakland, MD 21550
    407 Seneca Ave, Oakland, MD 21550
    407 Seneca Ave, Oakland, MD 21550
    /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, LLC

    407 Seneca Ave, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 2

Maryland Garrett County Oakland

Homes for Sale with Garage in Oakland, MD

Home Trends in Oakland, MD

On average, homes in Oakland, MD sell after 94 days on the market compared to the national average of 58 days. The median sale price for homes in Oakland, MD over the last 12 months is $412,500, up 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$412,500
Median Single Family Sale Price
$399,950
Median Townhouse Sale Price
$472,500
Median 2 Bedroom Sale Price
$311,500
Median 1 Bedroom Sale Price
$217,450
Average Price Per Sq Ft
$261
Number of Homes for Sale
60
Last 12 months Home Sales
142
Months of Supply
5.10
Median List Price
$402,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
How to Buy a Home How to Finance a Home How to Sell a Home

In Oakland, there are currently 41 homes for sale with a garage. Meeting the needs of buyers seeking secure parking and extra storage, these homes offer various garage options. Whether it's a property featuring a practical two-car garage or a larger residence with a sought-after three-car garage, these homes provide the convenience and flexibility desired by many homeowners. Additionally, some properties come with detached garages, offering ample space while ensuring privacy. Explore the selection of homes for sale with a garage in Oakland, MD and find the perfect place to call home.

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