36

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

    $285,000

    • 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
  • 1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    /150

    $4,250,000

    • 7 Beds
    • 7 Baths
    • 5,695 Sq Ft

    1240 Boy Scout Rd, Oakland, MD 21550

    Welcome to Double Eagle Ranch — quite possibly the most beautiful property in Garrett County. This iconic 50-acre estate is set in the heart of Deep Creek Lake and includes its own deeded waterfront parcel with a brand-new dock, giving you private lake access just minutes from the property. Rarely does an offering combine such incredible privacy, natural beauty, and income-producing potential in

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (240) 851-4712

    1240 Boy Scout Rd, 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
  • 433 San Francisco St, Oakland, MD 21550
    433 San Francisco St, Oakland, MD 21550
    433 San Francisco St, Oakland, MD 21550
    /66

    $599,900

    • 6 Beds
    • 2.5 Baths
    • 2,560 Sq Ft

    433 San Francisco St, Oakland, MD 21550

    Fully renovated, fully loaded, and fully ready to be your Deep Creek Lake getaway! This 6-bedroom mountain retreat is packed with upgrades—New flooring, new septic, new hot tub, and a sleek modern kitchen with concrete counters, soft-close cabinets, and stainless steel appliances. One wood-burning fireplace for the cozy nights, one propane for the lazy mornings. Two and a half bathrooms, all

    Jon Bell Railey Realty, Inc.

    433 San Francisco St, Oakland, MD 21550
  • 1001 Sutter Ln, Oakland, MD 21550
    1001 Sutter Ln, Oakland, MD 21550
    1001 Sutter Ln, Oakland, MD 21550
    /93

    $799,000

    • 5 Beds
    • 6 Baths
    • 6,550 Sq Ft

    1001 Sutter Ln, Oakland, MD 21550

    Discover the ultimate mountain–lake getaway in this stunning 5BR Southern-style home on a private 2.4-acre wooded lot bordering Broadford Lake recreational area! Located just minutes from Deep Creek Lake and Wisp Resort, this magnificent property offers over 6,500 sq ft. and delivers unforgettable space, luxury, and privacy. Step inside to soaring cathedral ceilings, skylights, oak floors, and a

    Nina Beitzel Railey Realty, Inc.

    1001 Sutter Ln, 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
    /71

    $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
  • 41 Boyd Paugh Ln, Oakland, MD 21550
    41 Boyd Paugh Ln, Oakland, MD 21550
    41 Boyd Paugh Ln, Oakland, MD 21550
    /103

    $2,399,000

    • 7 Beds
    • 5 Baths
    • 4,691 Sq Ft

    41 Boyd Paugh Ln, Oakland, MD 21550

    Gorgeous 7 bedroom home with dock slip! This newer construction home sits on a quiet corner of Deep Creek Lake with 200 feet of lake frontage. Located in the beautiful and quiet Heron Cove community and comes with two community lake access points, one with a sandy beach area, tennis courts, and walking trails. The level lot is surrounded by trees and designed for privacy and outdoor enjoyment,

    Rachel Bruch Railey Realty, Inc.

    41 Boyd Paugh Ln, Oakland, MD 21550
  • 697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    /56

    $339,000

    • 5 Beds
    • 3.5 Baths
    • 3,682 Sq Ft

    697 Monte Vista Rd, Oakland, MD 21550

    Tucked away just minutes from downtown Oakland, MD, lies a home that truly surprises with over 3,500 sq. ft. of living space on 1.88 acres with breathtaking farm and mountain views. Step inside the main level, where the master suite awaits along with two additional large bedrooms and a full bath, plus a mudroom area with a convenient half bath—perfect for entertaining. Cozy evenings are made even

    Laura Newhall Taylor Made Deep Creek Real Estate

    697 Monte Vista 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
  • 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
  • 163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, 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
  • 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
  • 1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    /67

    $749,000

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

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    With a new price you don't want to miss this chance! Beautifully maintained 5 bedroom 5 bathroom lake area chalet. Beautifully landscaped and situated on 4 +/- acres with partial views of the south side of Deep Creek Lake. Recently Professionally appraised for $868,000! This home offers it's new owners a tremendous amount of room for storage and entertaining. As well as 3 levels of finished

    Dan Shockey Taylor Made Deep Creek Real Estate

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • 815 Chadderton School Rd, Oakland, MD 21550
    815 Chadderton School Rd, Oakland, MD 21550
    815 Chadderton School Rd, Oakland, MD 21550
    /110

    $1,900,000

    • 5 Beds
    • 3.5 Baths
    • 4,619 Sq Ft

    815 Chadderton School Rd, Oakland, MD 21550

    Experience lakefront living at its finest in this exceptional 5-bedroom, 3.5-bath home offering over 4,600 square feet of living space on a private lot of more than one acre. Featuring an incredibly spacious primary suite on the main level, as well as an additional master suite on the second level, this home is ideal for both full-time living and hosting guests. Enjoy breathtaking lake views from

    Kevin Liller Railey Realty, Inc.

    815 Chadderton School Rd, Oakland, MD 21550
  • 723 Kings Ct, Oakland, MD 21550
    723 Kings Ct, Oakland, MD 21550
    723 Kings Ct, Oakland, MD 21550
    /67

    $359,700

    • 4 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    723 Kings Ct, Oakland, MD 21550

    "Charming two-story home situated on a beautiful .292-acre level lot in a prime location (Kings Hills Estates) Enjoy the perfect blend of comfort and convenience with spacious living areas, a serene yard ideal for outdoor entertaining. Ideally located near a top-rate Hospital, popular shopping destinations, and just minutes to Broadford Lake. Whether you're enjoying a day on the water or running

    Debra Beitzel Long & Foster Real Estate, Inc.

    723 Kings Ct, 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

    2725 Stockslager Rd, Oakland, MD 21550
  • 609 Southern Pines Dr, Oakland, MD 21550
    609 Southern Pines Dr, Oakland, MD 21550
    609 Southern Pines Dr, Oakland, MD 21550
    /50

    $425,000

    • 4 Beds
    • 2.5 Baths
    • 2,250 Sq Ft

    609 Southern Pines Dr, Oakland, MD 21550

    Welcome to your next dream home! Nestled on a 4-acre wooded lot, this custom built residence combines comfort, and convenience. Just minutes from Broadford Lake Park, healthcare, shopping, Deep Creek Lake, and Wisp Ski Resort, this peaceful property offers easy access to all the local amenities. Two story stone & cedar, 4BR, 2.5 Bath w/ 2 - car attached garage, & 2 - car detached garage. Property

    Brian Covell BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    609 Southern Pines Dr, 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
  • 961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    /50

    $359,000

    • 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

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

    $349,999

    • 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

    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
  • 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
    /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
  • 3749 Maryland Hwy, Oakland, MD 21550
    3749 Maryland Hwy, Oakland, MD 21550
    3749 Maryland Hwy, 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
  • 313 W Liberty St, Oakland, MD 21550
    313 W Liberty St, Oakland, MD 21550
    313 W Liberty St, Oakland, MD 21550
    /59

    $220,000

    • 2 Beds
    • 1 Bath
    • 1,064 Sq Ft

    313 W Liberty St, Oakland, MD 21550

    Charming and meticulously maintained 1947 brick ranch located at the edge of Oakland town limits on a beautiful 1⁄4-acre lot. This 2-bedroom, 1-bath home features spacious rooms, natural gas heat, public utilities, and a full unfinished basement offering great storage or future potential. Ownership includes a 1⁄2 interest in a shared 2-car garage. Conveniently situated near schools, the hospital,

    Justin Liller Railey Realty, Inc.

    313 W Liberty St, 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

    $865,000

    • 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,

    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

    $930,000

    • 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
  • 355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    /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
  • 3257 George Washington Hwy, Oakland, MD 21550
    3257 George Washington Hwy, Oakland, MD 21550
    3257 George Washington Hwy, Oakland, MD 21550
    /8

    $280,000

    • Land
    • 36.72 Acres
    • $7,625 per Acre

    3257 George Washington Hwy, Oakland, MD 21550

    Discover approximately 36.72 acres of beautiful wooded land offering privacy, mountain views, and exceptional convenience. This expansive property provides easy access to both George Washington Highway and Garrett Highway, making travel simple while still feeling tucked away in nature. Located within a 30-minute drive of Deep Creek Lake and Wisp Resort, as well as sought-after West Virginia

    Justin Liller Railey Realty, Inc.

    3257 George Washington Hwy, Oakland, MD 21550
  • 610 Harvey Winters Dr, Other, FL 21550
    610 Harvey Winters Dr, Other, FL 21550
    /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
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 89 days on the market compared to the national average of 55 days. The median sale price for homes in Oakland, MD over the last 12 months is $425,000, up 7% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$425,000
Median Single Family Sale Price
$405,000
Median Townhouse Sale Price
$485,000
Median 2 Bedroom Sale Price
$314,000
Median 1 Bedroom Sale Price
$229,900
Average Price Per Sq Ft
$258
Number of Homes for Sale
48
Last 12 months Home Sales
136
Months of Supply
4.20
Median List Price
$425,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
How to Buy a Home How to Finance a Home How to Sell a Home

In Oakland, there are currently 36 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.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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