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Oakland, MD Houses for Sale

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  • 55 Village Dr Unit 5, Oakland, MD 21550
    55 Village Dr Unit 5, Oakland, MD 21550
    55 Village Dr Unit 5, Oakland, MD 21550
    /45

    $585,000

    $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,280 Sq Ft

    55 Village Dr Unit 5, Oakland, MD 21550

    Tucked in the Yellowstone Village community at Deep Creek Lake, “Dan’s Mountain” is a charming log cabin retreat offering the perfect blend of mountain serenity and convenient access to the area’s top attractions. This 3-bedroom, 3-bathroom home comfortably accommodates guests spanning over 3 levels with a bonus enlcosed porch area. Warm wood interiors and a classic cabin feel welcome you inside,

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 358-4206

    55 Village Dr Unit 5, Oakland, MD 21550
  • 127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    /57

    $275,000

    $24K PRICE DROP
    • 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
  • 660 Glendale Rd, Oakland, MD 21550
    660 Glendale Rd, Oakland, MD 21550
    660 Glendale Rd, Oakland, MD 21550
    /62

    $1,100,000

    $200K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,592 Sq Ft

    660 Glendale Rd, Oakland, MD 21550

    Welcome to 660 Glendale Road — a luxury, mountain-chalet log home in the heart of Deep Creek Lake. This well appointed 5-bedroom, 3-bath home offers nearly 2,600 square feet of thoughtfully upgraded living space designed for lake life at its best. Enjoy lake views with western exposure on the expansive wraparound decks on main and lower levels. Many recent upgrades including roof, decks, covered

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 647-5278

    660 Glendale Rd, Oakland, MD 21550
  • 211 High Point Ridge Rd, Oakland, MD 21550
    211 High Point Ridge Rd, Oakland, MD 21550
    211 High Point Ridge Rd, Oakland, MD 21550
    /99

    $1,495,000

    • 4 Beds
    • 3.5 Baths
    • 3,472 Sq Ft

    211 High Point Ridge Rd, Oakland, MD 21550

    One in a lifetime opportunity to own one of Maryland’s most distinctive homes. Built in 2019, this fully custom modern home is located on the highest elevation building lot in the state of Maryland, making it the highest elevation home in the state at our 3300 feet above sea level. Designed to take full advantage of the setting, the property offers incredible panoramic views stretching across the

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 443-3345

    211 High Point Ridge Rd, Oakland, MD 21550
  • 122 Woodlands Hill Ln, Oakland, MD 21550
    122 Woodlands Hill Ln, Oakland, MD 21550
    122 Woodlands Hill Ln, Oakland, MD 21550
    /54

    $1,200,000

    • 4 Beds
    • 4.5 Baths
    • 2,656 Sq Ft

    122 Woodlands Hill Ln, Oakland, MD 21550

    Welcome to mountain living at its finest. Nestled on 6.89 private acres, 122 Woodlands Hill Lane offers the perfect blend of seclusion, space, and comfort in one of Garrett County’s most desirable settings. This impressive 4-bedroom, 4.5-bath home features approximately 4,000 square feet of living space designed for gathering, relaxing, and enjoying the beauty of Western Maryland. The home sits

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 290-8978

    122 Woodlands Hill Ln, 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
    /60

    $289,000

    $25K PRICE DROP
    • 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
  • 113 Jubb Meadows Ln, Oakland, MD 21550
    113 Jubb Meadows Ln, Oakland, MD 21550
    113 Jubb Meadows Ln, Oakland, MD 21550
    /69

    $899,900

    • 4 Beds
    • 3.5 Baths
    • 3,185 Sq Ft

    113 Jubb Meadows Ln, Oakland, MD 21550

    Luxury Estate just outside the town of Oakland. This 4-bed, 3.5 bath is situated on 9.72 acres. Offering 4,555 sq ft with vaulted ceilings, open concept living, and a rustic stacked stone fireplace. Modern gourmet kitchen with a large island and granite tops. Hardwood floors and timber frame accents throughout. Attached three-car garage. Full unfinished basement ready to add up to an additional

    Jon Bell Railey Realty, Inc.

    113 Jubb Meadows Ln, Oakland, MD 21550
  • 328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    /134

    $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
  • 130 Timberloft Cir Unit 14, Oakland, MD 21550
    130 Timberloft Cir Unit 14, Oakland, MD 21550
    130 Timberloft Cir Unit 14, Oakland, MD 21550
    /79

    $749,000

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft

    130 Timberloft Cir Unit 14, Oakland, MD 21550

    Centrally located in the heart of Deep Creek Lake, this beautifully maintained 3 bedroom, 3 bath home offers breathtaking lake and mountain views year round. Designed with an open floor plan, this home is perfect for entertaining. Enjoy the stunning scenery from the spacious main-level deck, or relax in the screened-in lower level porch. A cozy fireplace on both levels adds warmth and charm,

    Nicole Jackson Railey Realty, Inc.

    130 Timberloft Cir Unit 14, Oakland, MD 21550
  • 670 Woodlands Hill Ln, Oakland, MD 21550
    670 Woodlands Hill Ln, Oakland, MD 21550
    670 Woodlands Hill Ln, Oakland, MD 21550
    /72

    $1,689,000

    • 5 Beds
    • 4.5 Baths
    • 3,714 Sq Ft

    670 Woodlands Hill Ln, Oakland, MD 21550

    Experience what may be the most spectacular view in all of Deep Creek Lake! Perched in an extraordinary setting, this exceptional Yellowstone Log Home showcases breathtaking panoramic water views that create a true “top of the world” feel. Designed to capture the scenery from every angle, the main level features an open-concept layout with soaring natural light, a stunning stone fireplace, luxury

    Nina Beitzel Railey Realty, Inc.

    670 Woodlands Hill Ln, Oakland, MD 21550
  • 505 Southern Pines Dr, Oakland, MD 21550
    505 Southern Pines Dr, Oakland, MD 21550
    505 Southern Pines Dr, Oakland, MD 21550
    /38

    $287,500

    $10K PRICE DROP
    • 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, LLC

    505 Southern Pines Dr, 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
  • 2448 Birchwood Dr, Oakland, MD 21550
    2448 Birchwood Dr, Oakland, MD 21550
    2448 Birchwood Dr, Oakland, MD 21550
    /75

    $349,900

    • 4 Beds
    • 2 Baths
    • 3,352 Sq Ft

    2448 Birchwood Dr, Oakland, MD 21550

    Tucked within the sought-after Yough Mountain Resort community, this beautifully remodeled 4-bedroom, 2-bath mountain retreat blends rustic charm with thoughtful modern updates. Warm wood finishes, high ceilings, and inviting gathering spaces create a cozy lodge-style atmosphere, while upgrades throughout add comfort and convenience. The home features two full kitchens with granite countertops,

    Jon Bell Railey Realty, Inc.

    2448 Birchwood 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
    /57

    $749,900

    $29K PRICE DROP
    • 5 Beds
    • 1.5 Baths
    • 1,278 Sq Ft

    222 Skippers Point Rd, Oakland, MD 21550

    Lake cottage (5 Bedrooms) 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

    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

    $499,900

    $30K PRICE DROP
    • 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
  • 415 Nazelrod Rd, Oakland, MD 21550
    415 Nazelrod Rd, Oakland, MD 21550
    415 Nazelrod Rd, Oakland, MD 21550
    /52

    $3,249,000

    New Construction
    • 4 Beds
    • 5 Baths
    • 6,036 Sq Ft

    415 Nazelrod Rd, Oakland, MD 21550

    One of Garrett County's most unique and breathtaking mountain estates, this completely custom masterpiece was designed and built with exceptional craftsmanship and attention to detail. The 6000 +/- sq ft custom newly built home is located in the beautiful mountains of Garrett County, Maryland and offers the new owner one-of-a-kind unobstructed panoramic views, serenity, privacy and endless

    Larry Smith Railey Realty, Inc.

    415 Nazelrod Rd, Oakland, MD 21550
  • 809 N St, Oakland, MD 21550
    809 N St, Oakland, MD 21550
    809 N St, Oakland, MD 21550
    /13

    $63,000

    • 792 Sq Ft

    809 N St, Oakland, MD 21550

    Bring your vision and TLC to explore the possibilities here for rehab. Mt. Lake Park home being sold "As Is" Buyer to confirm with the county and the town of Mt. Lake Park for permits and building stipulations. Take a look & enjoy the ambiance of this historic area. RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. PROSPECTIVE PURCHASERS AND THEIR AGENTS ASSUME ALL LIABILITY

    Kathy Gibson Railey Realty, Inc.

    809 N St, Oakland, MD 21550
  • 251 Robinwood Dr, Oakland, MD 21550
    251 Robinwood Dr, Oakland, MD 21550
    251 Robinwood Dr, Oakland, MD 21550
    /61

    $969,000

    • 5 Beds
    • 4.5 Baths
    • 4,284 Sq Ft

    251 Robinwood Dr, Oakland, MD 21550

    One-of-a-kind Youghiogheny riverfront estate offering 400 feet of water frontage on 5+ acres and 2 separate lots. Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    251 Robinwood Dr, Oakland, MD 21550
  • 312 Moss Creek Cir, Oakland, MD 21550
    312 Moss Creek Cir, Oakland, MD 21550
    312 Moss Creek Cir, Oakland, MD 21550
    /55

    $795,000

    • 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
  • 654 N Bradley Ln, Oakland, MD 21550
    654 N Bradley Ln, Oakland, MD 21550
    654 N Bradley Ln, Oakland, MD 21550
    /41

    $424,900

    New Construction $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    654 N Bradley Ln, Oakland, MD 21550

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

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    654 N Bradley Ln, Oakland, MD 21550
  • 141 Montana Ln, Oakland, MD 21550
    141 Montana Ln, Oakland, MD 21550
    141 Montana Ln, 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
  • 511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    /10

    $375,000

    • 5 Beds
    • 1.5 Baths
    • 1,536 Sq Ft

    511 Main St, Oakland, MD 21550

    The property offered for sale is 32.20 acres located on the southwest & northwest corners of Maryland Highway, State Route 135 at Main Street & Sand Flat Road, Deer Park. The Single Family Residence built in 1920 has 5 bedrooms, 1 full bathroom and 1 half bathroom. The residence is being sold "As Is". The residence is prime for renovation; the parcel may have commercial potential. The current

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    511 Main St, Oakland, MD 21550
  • 2311 Boy Scout Rd, Oakland, MD 21550
    2311 Boy Scout Rd, Oakland, MD 21550
    2311 Boy Scout Rd, Oakland, MD 21550
    /78

    $1,579,900

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

    2311 Boy Scout Rd, Oakland, MD 21550

    Experience the best of Deep Creek Lake living from this private waterfront retreat tucked among mature trees on nearly an acre of land. With over 100 feet of lake frontage, a private Type-A dock, and a gentle distance to deep water, this property offers the kind of shoreline that's increasingly hard to find. Thoughtfully positioned to capture expansive lake views while preserving a sense of

    Jon Bell Railey Realty, Inc.

    2311 Boy Scout 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
  • 1021 E High St, Oakland, MD 21550
    1021 E High St, Oakland, MD 21550
    1021 E High St, Oakland, MD 21550
    /58

    $234,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,520 Sq Ft

    1021 E High St, Oakland, MD 21550

    ***BACK ON THE MARKET, don't miss this one a second time! Welcome home to this solid, ranch style home on one of Oakland's most convenient streets. Built in 1954, this 3-bedroom, 2-bath home delivers 1,520 sq ft of comfortable living, plus a partially finished full basement ready for your vision, whether that's a rec room, home office, or extra storage. The metal roof means peace of mind for

    Jeremy Cunningham Railey Realty, Inc.

    1021 E High St, Oakland, MD 21550
  • 17921 Garrett Hwy, Oakland, MD 21550
    17921 Garrett Hwy, Oakland, MD 21550
    17921 Garrett Hwy, Oakland, MD 21550
    /56

    $325,000

    Open Sun 10AM - 12:30PM $34K PRICE DROP
    • 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
  • 164 Grandview Dr, Oakland, MD 21550
    164 Grandview Dr, Oakland, MD 21550
    164 Grandview Dr, 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, LLC

    164 Grandview Dr, Oakland, MD 21550
  • 74 Parks Rd, Oakland, MD 21550
    74 Parks Rd, Oakland, MD 21550
    /2

    $64,900

    $5K PRICE DROP
    • 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
  • 83 Bethlehem Rd, Oakland, MD 21550
    83 Bethlehem Rd, Oakland, MD 21550
    83 Bethlehem Rd, Oakland, MD 21550
    /43

    $2,499,900

    • 4 Beds
    • 1.5 Baths
    • 2,190 Sq Ft

    83 Bethlehem Rd, Oakland, MD 21550

    Rare opportunity to own 327+/- acres of scenic countryside featuring a mix of open pasture, mature woods, and flowing stream frontage along Block Run. This 4-bedroom, 1.5-bath farmhouse is privately tucked among rolling fields and mountain views, offering endless potential for farming, recreation, hunting, ATV trails, or a private estate. Multiple barns and outbuildings provide ample storage and

    Jon Bell Railey Realty, Inc.

    83 Bethlehem Rd, 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
  • 511 Hilltop Rd, Oakland, MD 21550
    511 Hilltop Rd, Oakland, MD 21550
    511 Hilltop Rd, Oakland, MD 21550
    /51

    $434,900

    • 4 Beds
    • 3 Baths
    • 2,406 Sq Ft

    511 Hilltop Rd, Oakland, MD 21550

    Tucked away on a quiet cul-de-sac in the desirable Royal Charlotte community, this stunning 4-bedroom, 3-bathroom home is the kind of property you'll fall in love with the moment you arrive. Surrounded by the beauty and tranquility of the mountains and accessed by county-maintained roads, this impeccably maintained home showcases pride of ownership throughout. From the expansive Trex decking that

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    511 Hilltop Rd, Oakland, MD 21550
  • 1038 S Blakeslee Rd, Oakland, MD 21550
    1038 S Blakeslee Rd, Oakland, MD 21550
    1038 S Blakeslee Rd, 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, LLC

    1038 S Blakeslee Rd, Oakland, MD 21550
  • 1499 Foster Rd, Oakland, MD 21550
    1499 Foster Rd, Oakland, MD 21550
    1499 Foster Rd, Oakland, MD 21550
    /64

    $415,000

    • 4 Beds
    • 2 Baths
    • 2,234 Sq Ft

    1499 Foster Rd, Oakland, MD 21550

    Welcome to Ricky's Retreat, a beautifully renovated mountain retreat nestled on 1.17 private wooded acres in the heart of Garrett County. Ideally located just minutes from Deep Creek Lake, Wisp Resort, Swallow Falls State Park, and downtown Oakland, this turnkey property offers the perfect balance of privacy, recreation, and modern comfort. Originally built as a raised ranch, the home has

    Kelsey Meyers Railey Realty, Inc.

    1499 Foster Rd, Oakland, MD 21550
  • 321 N 3rd St, Oakland, MD 21550
    321 N 3rd St, Oakland, MD 21550
    321 N 3rd St, Oakland, MD 21550
    /48

    $385,000

    $15K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 3,660 Sq Ft

    321 N 3rd St, Oakland, MD 21550

    Reduced and Ready to go!! Perfect one level retirement retreat or 2nd vacation home! 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

    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
  • 137 Paradise Gardens Rd, Oakland, MD 21550
    137 Paradise Gardens Rd, Oakland, MD 21550
    137 Paradise Gardens Rd, Oakland, MD 21550
    /71

    $999,000

    $50K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,730 Sq Ft

    137 Paradise Gardens Rd, Oakland, MD 21550

    Remodeled 4BR/2BA lakefront A-frame with two deep water dock slips! Impressive renovation from top to bottom, this home has everything you are seeking in a vacation home AND a huge, fenced in yard surrounded by massive trees, fire pit and storage building. Features include a massive stone fireplace (wood burning), hot tub with lake views, large kitchen with island, custom tile showers & bathrooms

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    137 Paradise Gardens Rd, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 2

Maryland Garrett County Oakland

Houses for Sale in Oakland, MD

Why Live in Oakland

Oakland, MD, located in the western part of the state, is known for its natural beauty and outdoor activities. The city is home to Deep Creek Lake, Maryland's largest freshwater lake, which offers nearly 70 miles of shoreline for boating, fishing, and swimming. Deep Creek Lake State Park provides public access with beaches, a boat launch, and extensive hiking and biking trails. Wisp Resort, the state's only ski resort, features 33 ski runs and year-round activities including hiking, disc golf, and golf courses. Oakland's downtown area showcases a variety of home styles, from vintage Victorians and Craftsmans to midcentury ranch-style houses. Lakefront properties often include A-frame cabins and Craftsman houses with private docks. Dining options in Oakland range from the casual Englanders diner, known for its buckwheat pancakes, to the upscale Stonecroft Manor steakhouse. Community events such as the Mountain Fresh Farmers Market and the Autumn Glory Festival foster a sense of local camaraderie. Students in Oakland attend Southern Garrett High School, which offers career and technical education programs. U.S. Route 219 runs through Oakland, connecting it to Interstate 68 and nearby cities like Cumberland, 50 miles away, and Morgantown, West Virginia, 55 miles away.

Learn more about living in Oakland

Single Family Home Prices in Oakland, MD

The median price for single family homes in Oakland is $405,000, and there are 66 single family home listings available for sale.

Single Family Home Price Trends

Median Home Price
$405,000
Median 3-Bedroom Home Price
$280,500
Median 4-Bedroom Home Price
$552,500
Median 5-Bedroom Home Price
$807,500
How to Buy a Home How to Finance a Home How to Sell a Home

In Oakland, there are currently 66 houses for sale, offering an array of options for potential buyers. With houses priced between $40,000 to $6,499,900, there's a range to accomodate every budget. As of June, 2026 the median home price in Oakland is $410,000, while the average sale price is $577,269, offering insights into the local housing market. On average, houses spend 97 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.

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