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Oakland, MD Houses for Sale

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  • 621 Paradise Heights, Oakland, MD 21550
    621 Paradise Heights, Oakland, MD 21550
    621 Paradise Heights, Oakland, MD 21550
    /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
  • 62 Duck Cove Rd, Oakland, MD 21550
    62 Duck Cove Rd, Oakland, MD 21550
    62 Duck Cove Rd, Oakland, MD 21550
    /75

    $2,195,000

    • 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
  • 65 Village Dr Unit 6, Oakland, MD 21550
    65 Village Dr Unit 6, Oakland, MD 21550
    65 Village Dr Unit 6, Oakland, MD 21550
    /52

    $695,000

    • 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. The Yellowstone Village community offers one of Deep

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 759-2822

    65 Village Dr Unit 6, Oakland, MD 21550
  • 15 Village Dr Unit 1, Oakland, MD 21550
    15 Village Dr Unit 1, Oakland, MD 21550
    15 Village Dr Unit 1, 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
  • 1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    /149

    $4,450,000

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

    1240 Boy Scout Rd, Oakland, MD 21550

    An Iconic 50-acre Estate at Deep Creek Lake with a Deeded Boat Slip, Equestrian Amenities and Rental/Event Potential!Introducing "Double Eagle Ranch," a one-of-a-kind property at Deep Creek Lake, offering the perfect blend of luxury, outdoor adventure, and incredible income-producing potential. This 50-acre Aspen style ranch and estate is a true gem for horse lovers, nature enthusiasts, and those

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (240) 851-4712

    1240 Boy Scout Rd, Oakland, MD 21550
  • 1056 Sunrise Dr, Oakland, MD 21550
    1056 Sunrise Dr, Oakland, MD 21550
    1056 Sunrise Dr, 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
  • 163 Crestview Dr, Oakland, MD 21550
    163 Crestview Dr, Oakland, MD 21550
    163 Crestview Dr, 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
  • 16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    /70

    $589,000

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

    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550

    Welcome to this beautifully crafted 4 bedroom, 3 bath home nestled in the sought-after Silver Ridge community, right in the heart of Deep Creek Lake. Just minutes from Wisp Resort, the lake’s public access, and all four of the area’s premier golf courses, this home offers an unbeatable location for year-round adventure and relaxation.From the moment you arrive, the home’s craftsman-style

    Justin Liller Railey Realty, Inc.

    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
  • 113 Paradise Ln, Oakland, MD 21550
    113 Paradise Ln, Oakland, MD 21550
    113 Paradise Ln, Oakland, MD 21550
    /61

    $1,389,000

    • 5 Beds
    • 3 Baths
    • 2,056 Sq Ft

    113 Paradise Ln, Oakland, MD 21550

    Incredible opportunity to own a 5 bedroom, 3 bath lakefront home with over 215 feet of prime frontage on Deep Creek Lake! Situated on a level to gently sloping lot, this property offers expansive views and easy lake access in one of the area's most desirable settings. Inside, you’ll find tasteful upgrades throughout—including a beautifully renovated kitchen with higher-end finishes and updated

    Nina Beitzel Railey Realty, Inc.

    113 Paradise Ln, Oakland, MD 21550
  • 444 Woodlands Hill Ln, Oakland, MD 21550
    444 Woodlands Hill Ln, Oakland, MD 21550
    444 Woodlands Hill Ln, Oakland, MD 21550
    /83

    $1,295,000

    • 4 Beds
    • 6 Baths
    • 4,744 Sq Ft

    444 Woodlands Hill Ln, Oakland, MD 21550

    Experience the serenity of Deep Creek Lake from this updated luxury 4 bedroom home with over 5,000+ square feet! The seller’s improvements over the last few years showcase impeccable craftsmanship and outstanding construction quality, both inside and out. Nestled on 2 acres in a private community, enjoy beautiful water views of the lake from the expansive front deck or from many of the interior

    Mike Kennedy Railey Realty, Inc.

    444 Woodlands Hill Ln, Oakland, MD 21550
  • 783 Mountainview Dr, Oakland, MD 21550
    783 Mountainview Dr, Oakland, MD 21550
    783 Mountainview Dr, Oakland, MD 21550
    /76

    $595,000

    • 3 Beds
    • 3 Baths
    • 1,971 Sq Ft

    783 Mountainview Dr, Oakland, MD 21550

    Beautiful, 3 bedroom, 3 bath home located in the sought after community of Mountainside at Deep Creek Lake. This home offers one level living, 2 bonus rooms which could be used as extra sleeping areas, a sauna, 2 car attached garage, a large & level yard. Enjoy several community amenities including lake access, a marina, picnic areas, tennis & basketball courts, & more! A current vacation rental

    Larry Smith Railey Realty, Inc.

    783 Mountainview Dr, Oakland, MD 21550
  • 102 Mountainview Ct, Oakland, MD 21550
    102 Mountainview Ct, Oakland, MD 21550
    102 Mountainview Ct, Oakland, MD 21550
    /103

    $975,000

    • 7 Beds
    • 4.5 Baths
    • 5,376 Sq Ft

    102 Mountainview Ct, Oakland, MD 21550

    Mountainside Luxury Log Home. "Boulder Escape" is a stunning 7-bedroom, 4.5 bath lake access home on 1.6 acres in this prestigious mountaintop community. This income-producing property, offering over 5600 square feet, has an open concept floor plan with amazing expansive space on all levels. You will find an easy flow throughout the living, dining, and kitchen areas. Comfort and ambiance are

    Kathy Gibson Railey Realty, Inc.

    102 Mountainview Ct, Oakland, MD 21550
  • 56 Bee Tree Ln, Oakland, MD 21550
    56 Bee Tree Ln, Oakland, MD 21550
    56 Bee Tree Ln, Oakland, MD 21550
    /141

    $2,845,000

    • 6 Beds
    • 7.5 Baths
    • 5,100 Sq Ft

    56 Bee Tree Ln, Oakland, MD 21550

    Unmatched EXCEPTIONAL Lakefront Living – 6 Bedrooms | 7.5 Baths | Tucked Among the PinesDiscover a rare opportunity to own a true lakefront, lakeview gem—this 5,400 sq ft, 6-bedroom, 7.5-bath home that is nestled among tall pines on an exceptional lot that sits unusually close to the water’s edge. With peaceful views across a quiet cove and expansive open-water vistas from the oversized

    Susan Bell Railey Realty, Inc.

    56 Bee Tree Ln, 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
  • 328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    /117

    $565,000

    • 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

    Kathy Gibson Railey Realty, Inc.

    328 Stool Rock Rd, Oakland, MD 21550
  • 2719 Broadford Rd, Oakland, MD 21550
    2719 Broadford Rd, Oakland, MD 21550
    2719 Broadford Rd, Oakland, MD 21550
    /98

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 4,253 Sq Ft

    2719 Broadford Rd, Oakland, MD 21550

    Stunning Brick Ranch Near Broadford Lake Park! This magnificent one-level brick ranch sits on a level 1.5-acre lot backing to scenic farmland and walking distance to Broadford Lake Park. The 3,600 sq. ft. floor plan includes a master suite with a private bath, his & her closets, custom tiled shower, and granite vanity tops.The recently remodeled kitchen features granite countertops, an oversized

    Rich Orr Railey Realty, Inc.

    2719 Broadford Rd, Oakland, MD 21550
  • 25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    /52

    $775,000

    • 5 Beds
    • 4 Baths
    • 2,364 Sq Ft

    25 Silver Tree Ln, Oakland, MD 21550

    Beautiful lake access retreat located in the Silver Tree Landings community. This recently updated contemporary home feels warm and inviting from the moment you walk in (upgrade list available). Offering hardwood flooring, granite countertops, two stone propane fireplaces and cathedral ceilings. The abundance of windows allows the natural light to brighten any season, while offering views from

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    25 Silver Tree Ln, Oakland, MD 21550
  • 155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    /51

    $699,900

    • 5 Beds
    • 3 Baths
    • 2,792 Sq Ft

    155 Basswood Way, Oakland, MD 21550

    Tucked just off Lakeshore Drive, this log home nails that luxury treehouse feel. Wrapped in fresh stain (09/24) and packed with updates - "Time Is On My Side" is dialed in for comfort. Five bedrooms, three baths, including a main-level primary. Inside, modern meets rustic with a sleek kitchen, new propane fireplace, and fresh paint throughout. The lower level offers a second living area, pool

    Michael Fenton Railey Realty, Inc.

    155 Basswood Way, Oakland, MD 21550
  • 36 Ridgewood Dr, Oakland, MD 21550
    36 Ridgewood Dr, Oakland, MD 21550
    36 Ridgewood Dr, Oakland, MD 21550
    /60

    $525,000

    • 3 Beds
    • 3.5 Baths
    • 1,713 Sq Ft

    36 Ridgewood Dr, Oakland, MD 21550

    Looking for the secluded cabin in the woods but want to be close to everything the Lake has to offer? Look no further! This 3 bedroom 3 1/2 bath home offers just that! Located in the established and sought after community of Mountainside, this home is an inviting and place where you can get away from it all. Cozy up to the large stone wood burning fireplace in the living room, open concept

    Larry Smith Railey Realty, Inc.

    36 Ridgewood Dr, Oakland, MD 21550
  • 3084 Lake Shore Dr, Oakland, MD 21550
    3084 Lake Shore Dr, Oakland, MD 21550
    3084 Lake Shore Dr, Oakland, MD 21550
    /71

    $625,000

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

    3084 Lake Shore Dr, Oakland, MD 21550

    Cozy Retreat on Lake Shore Drive! This 4-bed, 3-bath cottage was built for relaxation, entertainment, and making memories. The open-concept living area keeps everyone connected, while the expansive deck and hot tub allow you to take the fun outside. Upstairs, the primary suite steals the show! A personal fireplace with a wall of glass to let in the light and soak in the views. Three more bedrooms

    Jon Bell Railey Realty, Inc.

    3084 Lake Shore Dr, Oakland, MD 21550
  • 1118 Lake Shore Dr, Oakland, MD 21550
    1118 Lake Shore Dr, Oakland, MD 21550
    1118 Lake Shore Dr, Oakland, MD 21550
    /101

    $675,000

    • 3 Beds
    • 2 Baths
    • 2,446 Sq Ft

    1118 Lake Shore Dr, Oakland, MD 21550

    Escape to Serenity: Your Dream Log Home Awaits! Nestled in the heart of a picturesque lake and mountain area, this charming log home offers the perfect blend of rustic charm and modern touches. With cathedral wood ceilings and a cozy gas fireplace, the spacious living area invites you to relax and soak in the warmth and beauty of your surroundings. The living area steps out to a large covered

    Susan Bell Railey Realty, Inc.

    1118 Lake Shore Dr, Oakland, MD 21550
  • 439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    /45

    $1,359,000

    • 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
  • 1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    /93

    $3,689,000

    • 5 Beds
    • 5.5 Baths
    • 5,100 Sq Ft

    1931 Lake Shore Dr, Oakland, MD 21550

    Deep Creek Lakes, Sunset Hills, luxury retreat offering majestic mountain & lake views. A unique lakefront property that plays a perfect host to relaxing vacations with family and friends is a low-key lifestyle centered around the outdoors. Vast stretches of glass ensure a sparkling water view is always on hand. Though sleek materials and high-end finishes abound, their low-profile design puts

    Russell Bounds Railey Realty, Inc.

    1931 Lake Shore Dr, Oakland, MD 21550
  • 1674 Paradise Point Rd, Oakland, MD 21550
    1674 Paradise Point Rd, Oakland, MD 21550
    1674 Paradise Point Rd, Oakland, MD 21550
    /53

    $1,599,900

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft

    1674 Paradise Point Rd, Oakland, MD 21550

    Beautifully remodeled lakefront home offering private dock and stunning views of Deep Creek Lake! Located on Paradise Point Rd, this home faces south for abundant natural light. 4 Bedrooms, 2.5 Bathrooms and sold fully furnished providing a gorgeous contemporary aesthetic throughout. Bright and Open with lots of glass to bring in the scenic lake views! Cozy fireplace in the main living area.

    Jon Bell Railey Realty, Inc.

    1674 Paradise Point Rd, Oakland, MD 21550
  • 503 Southern Pines Dr, Oakland, MD 21550
    503 Southern Pines Dr, Oakland, MD 21550
    503 Southern Pines Dr, Oakland, MD 21550
    /62

    $399,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,642 Sq Ft

    503 Southern Pines Dr, Oakland, MD 21550

    Brand new and built to make life easy. Tucked in the quiet, sought-after Southern Pines community, this single-level home keeps everything simple and smooth. Three beds, two and a half baths, and space that actually works. Oversized two-car heated garage. Inside, the kitchen comes complete with stainless appliances, hardwood cabinets, stone tops, walk-in pantry, and a big island bar made for

    Jon Bell Railey Realty, Inc.

    503 Southern Pines Dr, Oakland, MD 21550
  • 1720 Pysell Crosscut Rd, Oakland, MD 21550
    1720 Pysell Crosscut Rd, Oakland, MD 21550
    1720 Pysell Crosscut Rd, Oakland, MD 21550
    /114

    $999,999

    • 5 Beds
    • 5.5 Baths
    • 8,000 Sq Ft

    1720 Pysell Crosscut Rd, Oakland, MD 21550

    'Four Winds' is a Frank Lloyd Wright inspired masterpiece at Deep Creek Lake. Restored & renovated as recently as 2021, this 4/5BR home boasts 8000sf on nearly 5 acres of land. A small part of the home was converted to accommodate a successful medical practice - 2 patient rooms, bathroom & private office - which adds amazing potential to creatively 'work from home' in many professional fields

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    1720 Pysell Crosscut Rd, Oakland, MD 21550
  • 425 Mountainview Dr, Oakland, MD 21550
    425 Mountainview Dr, Oakland, MD 21550
    425 Mountainview Dr, Oakland, MD 21550
    /50

    $829,000

    • 3 Beds
    • 2.5 Baths
    • 1,586 Sq Ft

    425 Mountainview Dr, Oakland, MD 21550

    Stunning mountain retreat is what comes to mind when pulling into this home. The covered front porch feels warm and inviting from the moment you arrive. Offering a beautiful stone wood burning fireplace, an impressive granite kitchen island, three bedrooms and a great loft area. Not to mention a two-car attached garage with the ability to finish off a room above that you could connect to the main

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    425 Mountainview Dr, Oakland, MD 21550
  • 353 Basswood Way Unit 24, Oakland, MD 21550
    353 Basswood Way Unit 24, Oakland, MD 21550
    353 Basswood Way Unit 24, Oakland, MD 21550
    /64

    $710,000

    • 4 Beds
    • 3 Baths
    • 2,664 Sq Ft

    353 Basswood Way Unit 24, Oakland, MD 21550

    Experience year-round mountain charm at “Tucked Inn,” a stunning wooded cabin in the desirable Gallatin Woods community. Perfectly situated just minutes from Deep Creek Lake and Wisp Resort, this retreat keeps you close to every season’s best activities—boating, skiing, hiking, and more. Enjoy peaceful walks along community trails, vibrant fall foliage, or sunny summer days on the spacious

    Nina Beitzel Railey Realty, Inc.

    353 Basswood Way Unit 24, Oakland, MD 21550
  • 1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    /61

    $835,000

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

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    Coming Soon! 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. This home offers it's new owners a tremendous amount of room for storage and entertaining. As well as 3 levels of finished living space. Featuring a large heated garage with multiple car storage and additional

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • 198 Grandview Dr, Oakland, MD 21550
    198 Grandview Dr, Oakland, MD 21550
    198 Grandview Dr, Oakland, MD 21550
    /45

    $825,000

    • 3 Beds
    • 3 Baths
    • 2,744 Sq Ft

    198 Grandview Dr, Oakland, MD 21550

    Lake views for days and room to relax in every direction!Welcome to 198 Grandview Drive, a 3-bedroom, 3-bath log home perfectly perched to capture sweeping views of Deep Creek Lake and the surrounding mountains. With three finished levels of living space, this home blends rustic charm with modern comfort. Hardwood floors span the main and upper levels, while the finished lower level features

    Heather Taylor RE/MAX One

    198 Grandview Dr, 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
  • 131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    /53

    $529,500

    • 4 Beds
    • 3.5 Baths
    • 2,422 Sq Ft

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550

    Craftsman-style home in the much sought after Silver Ridge community. Once you enter, you'll find a lovely great room, an open kitchen/dining/living area, a powder room, and a spacious primary boasting a corner gas fireplace. Most of the main level features hardwood flooring and a large entryway. The upper level has a great loft area, three bedrooms, laundry room, and two additional bathrooms.

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
  • 175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    /55

    $555,000

    • 4 Beds
    • 4.5 Baths
    • 3,192 Sq Ft

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550

    Amazing and rare opportunity in Trader's Landing! These wonderful stand alone homes in this community do not come up for sale very often. Offering 4 bedrooms, 4 and a half baths, and over 3,100 finished square feet on 4 levels of living space, this is one of the largest homes in the development! Enjoy relaxing with some nice views on the spacious deck or go for a soak in the hot tub on the

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
  • 355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    /22

    $599,000 Open House 9/01

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

    355 Lonesome Pine Rd, Oakland, MD 21550

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

    Brody Monahan Lake Homes Realty, LLC

    355 Lonesome Pine Rd, Oakland, MD 21550
  • 20 Maple Del Ln, Oakland, MD 21550
    20 Maple Del Ln, Oakland, MD 21550
    20 Maple Del Ln, Oakland, MD 21550
    /17

    $549,000 New Construction

    • 2 Beds
    • 1 Bath

    20 Maple Del Ln, Oakland, MD 21550

    *To be built A frame* Looking for a newly built home on a wooded lot close to everything Deep Creek Lake offers. This home can be delivered complete in a 4 month time span. Call today for details

    Michael Cumerlato Jason Mitchell Group

    20 Maple Del Ln, Oakland, MD 21550
  • 620 Crosby Dr, Oakland, MD 21550
    620 Crosby Dr, Oakland, MD 21550
    620 Crosby Dr, Oakland, MD 21550
    /21

    $555,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,850 Sq Ft

    620 Crosby Dr, Oakland, MD 21550

    BRAND NEW CONSTRUCTION! 4BR/3.5BA home with attached 2 car garage in Country Club Acres! Perched at the very top of the mountain overlooking Oakland golf course, 2,850 sf and 2.84 acres of land (lots 73-79 combined). Modern design offering plenty of natural light, open living and elite finishes. Features include Andersen windows & sliders, multiple ensuites, custom tile bathrooms, fireplace,

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    620 Crosby Dr, Oakland, MD 21550
  • 1101 Wheeling Ave, Oakland, MD 21550
    1101 Wheeling Ave, Oakland, MD 21550
    1101 Wheeling Ave, Oakland, MD 21550
    /23

    $190,000

    • 3 Beds
    • 2 Baths
    • 1,718 Sq Ft

    1101 Wheeling Ave, Oakland, MD 21550

    Investor Opportunity – 1101 Wheeling Ave, Oakland, MD 21550 – $190,000Attention Investors and Visionaries!Unlock the potential in this unique property located in the heart of Oakland, Maryland. Priced to move at $190,000, this hidden gem offers a perfect canvas for your next flip, rental, or renovated. Features 3 bedrooms 2 baths, 2 car garage, wrap around porch, jacuzzi and a pool!

    Tanavia Greer Long & Foster Real Estate, Inc.

    1101 Wheeling Ave, Oakland, MD 21550
  • 88 Knoll Crest Heights Dr, Oakland, MD 21550
    88 Knoll Crest Heights Dr, Oakland, MD 21550
    88 Knoll Crest Heights Dr, Oakland, MD 21550
    /38

    $219,000

    • 3 Beds
    • 2.5 Baths
    • 1,867 Sq Ft

    88 Knoll Crest Heights Dr, Oakland, MD 21550

    Discover the perfect blend of convenience and country charm in this 3-bedroom, 2.5-bath home (one bath unfinished) set on a spacious lot with incredible mountain and valley views. Enjoy the peaceful atmosphere of a rural setting while being just minutes from downtown Oakland’s shopping, dining, schools, and Garrett Regional Medical Center.Inside, you’ll find a comfortable and functional

    Justin Liller Railey Realty, Inc.

    88 Knoll Crest Heights Dr, Oakland, MD 21550
  • 110 W Pennington St, Oakland, MD 21550
    110 W Pennington St, Oakland, MD 21550
    110 W Pennington St, Oakland, MD 21550
    /24

    $110,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    110 W Pennington St, Oakland, MD 21550

    Affordable starter home on an alley in the town of Oakland with many possibilities. This rancher offers hardwood floors, newer roof , newer siding, covered porch and a full basement that can provide more living space. The natural gas heat is another plus. You are also within walking distance to many things in downtown Oakland.

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    110 W Pennington St, 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

    • 4 Beds
    • 4.5 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

Showing Results 1 - 40, Page 1 of 3

Maryland Garrett County Oakland

Houses for Sale in Oakland, MD

Home Trends in Oakland, MD

On average, homes in Oakland, MD sell after 93 days on the market compared to the national average of 52 days. The median sale price for homes in Oakland, MD over the last 12 months is $402,500, down 15% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$402,500
Median Single Family Sale Price
$455,500
Median Townhouse Sale Price
$557,450
Median 2 Bedroom Sale Price
$384,000
Median 1 Bedroom Sale Price
$276,500
Average Price Per Sq Ft
$269
Number of Homes for Sale
76
Last 12 months Home Sales
114
Months of Supply
8.00
Median List Price
$445,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-15%
How to Buy a Home How to Finance a Home How to Sell a Home

In Oakland, there are currently 103 houses for sale, offering an array of options for potential buyers. With houses priced between $110,000 to $4,450,000, there's a range to accomodate every budget. As of August, 2025 the median home price in Oakland is $445,000, while the average sale price is $530,600, offering insights into the local housing market. On average, houses spend 93 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale 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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