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Newest Homes for Sale in Oakland, MD

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  • /57

    $219,000

    • 1 Bed
    • 1.5 Baths
    • 912 Sq Ft

    141 Montana Ln, Oakland, MD 21550

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

    Larry Smith Railey Realty, Inc.

    141 Montana Ln, Oakland, MD 21550
  • /50

    $950,000

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

    164 Grandview Dr, Oakland, MD 21550

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

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    164 Grandview Dr, Oakland, MD 21550
  • /2

    $69,900

    • 3 Beds
    • 1 Bath
    • 792 Sq Ft

    74 Parks Rd, Oakland, MD 21550

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

    Emillie Albrecht Real Broker, LLC

    74 Parks Rd, Oakland, MD 21550
  • /28

    $299,000

    • 2 Beds
    • 1 Bath
    • 550 Sq Ft

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550

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

    Agent Photo

    James Matthews

    Taylor Made Deep Creek Real Estate

    (240) 883-5848

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

    $35,000

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

    233 Rhododendron Dr, Oakland, MD 21550

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

    Laura Newhall Taylor Made Deep Creek Real Estate

    233 Rhododendron Dr, Oakland, MD 21550
  • /38

    $292,500

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

    505 Southern Pines Dr, Oakland, MD 21550

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

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

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

    $60,000

    • 2 Beds
    • 1 Bath
    • 782 Sq Ft

    820 N 4th St, Oakland, MD 21550

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

    Duane Stein II The KW Collective

    820 N 4th St, Oakland, MD 21550
  • /5

    $89,900

    • Land
    • 15.75 Acres
    • $5,708 per Acre

    TBD 15 75 Acres Bethlehem Rd, Oakland, MD 21550

    Tucked away just minutes from town, this 15.75± acre wooded parcel offers a quiet country setting with the privacy many buyers are searching for. Located off Bethlehem Road near the Potomac State Forest, the property features largely level terrain, mature trees, and abundant wildlife—an ideal backdrop for a private residence, weekend retreat, or recreational use. The surrounding area provides

    Thomas Long Railey Realty, Inc.

    TBD 15 75 Acres Bethlehem Rd, 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
  • /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
  • /29

    $284,900

    • 2 Beds
    • 2 Baths
    • 1,340 Sq Ft

    8 Laurel Brook Dr, Oakland, MD 21550

    Re-positioned price to sell. Beautiful Renovated 2-bedroom, 2-bath condo is Turnkey Ready Now for Part-time, Full-time Living or Rental, located in this quiet desirable Laurel Brook community, close to the lake, local activities, and everyday amenities. Warm, welcoming, and filled with natural light, the home features mountain views and a skylight in the living room that enhances the open airy

    Karen Hart Cummings & Co. Realtors

    8 Laurel Brook Dr, Oakland, MD 21550
  • /18

    $4,000

    • Land
    • 0.47 Acre
    • $8,511 per Acre

    Lot 36 Fox Tail Rd, Oakland, MD 21550

    Discover your mountain escape in Yough Mountain Resort, a gated recreational community in the scenic mountains of Western Maryland, just a short drive to Deep Creek Lake. This amenity-rich community is designed for outdoor enthusiasts, offering ATV and snowmobile trails, Yough River access, nearby state parks, hunting opportunities, plus a playground and pavilion area for gathering.This

    Shannon McWilliams Taylor Made Deep Creek Real Estate

    Lot 36 Fox Tail 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
  • /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
  • /37

    $629,000

    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft

    231 Santa fe Trail, Oakland, MD 21550

    3/4BR 3BA chalet with LAKE VIEWS! 2300sf vacation home fronting on a mountain stream, overlooking Deep Creek Lake! Enjoy an eat-in kitchen, exposed beams and a loft area that the current owners use as a 4th BR with bathroom. NO HOA! Conveys fully furnished. Features include central AC, exposed beams, updated flooring, gas fireplace on main level, lower level rec room with pool table and

    Jay Ferguson Taylor Made Deep Creek Real Estate

    231 Santa fe Trail, 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
  • /39

    $425,000

    • 2 Beds
    • 2.5 Baths
    • 2,960 Sq Ft

    232 Jeffrey Ln Unit 33, Oakland, MD 21550

    Turn-key and fully furnished, this beautifully maintained duplex offers the perfect blend of comfort, views, and location in the heart of Deep Creek Lake. Featuring an open, inviting floor plan, the home is designed for both everyday enjoyment and effortless entertaining. The main level features a spacious living area with a stone-surround fireplace, abundant natural light, and a seamless flow to

    Sean Brink Samson Properties

    232 Jeffrey Ln Unit 33, 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
  • /53

    $509,000

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

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550

    Welcome to this 4-bedroom, 4.5-bath stand-alone, multi-level unit in Traders Landing! Offering filtered lake views, ample square footage, oversized bedrooms, and multiple living spaces, this property is ideal for entertaining, large groups, or relaxed mountain-lake living. Enjoy a central Deep Creek location just minutes from Deep Creek Lake, local restaurants, shopping, and Wisp Resort.

    Nina Beitzel Railey Realty, Inc.

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
  • /19

    $295,000

    • Land
    • 8.48 Acres
    • $34,788 per Acre

    26 Green Brier Rd, Oakland, MD 21550

    8.48± acres offering excellent commercial or residential potential. Property features an existing well and septic system, with easy access and outstanding visibility. Conveniently located just minutes from the Oakland city limits outside of Zoning Districts. Ideal opportunity for development or investment.

    Rich Orr Railey Realty, Inc.

    26 Green Brier Rd, 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
  • /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
  • /10

    $995,000

    • Land
    • 0.58 Acre
    • $1,715,517 per Acre

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550

    RARE OPPURTUNITY! Discover one of the final opportunities to own true lakefront on the iconic Glendale Road! This premier homesite offers approximately 75 feet of pristine Deep Creek Lake frontage in a serene no wake zone, perfect for swimming, kayaking, and peaceful lakeside enjoyment. Zoning in this area is Town Center. This allows for a larger building area within the lot with relaxed

    Lucas Muenchow Railey Realty, Inc.

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
  • /20

    $189,000 New Construction

    • 4 Beds
    • 2 Baths

    3395 Fingerboard Rd, Oakland, MD 21550

    6+ acre homestead with a 4BR, 2BA home currently under construction. Sellers plans have changed and they will not be finishing the house. The structure is under roof, mostly framed-in with building materials on site that will convey with the sale. A new well has been drilled and septic permit is approved for 4BRs. Located just outside of town limits, this parcel has impressive mountain views and

    Jay Ferguson Taylor Made Deep Creek Real Estate

    3395 Fingerboard Rd, 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
  • /10

    $5,000

    • Land
    • 0.65 Acre
    • $7,692 per Acre

    Lot 17 Birchwood Dr, Oakland, MD 21550

    Lot 17 Birchwood Drive is a .65-acre wooded, NON-BUILDABLE membership lot located in the Youghiogheny Mountain Resort community in Oakland, MD. While you cannot build on this lot, this lot's ownership offers full membership access to the community’s amenities, including over 50 miles of private roads and trails perfect for ATV riding, UTVs, dirt bikes, hiking, and outdoor recreation. Ideal for

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 512-9707

    Lot 17 Birchwood Dr, 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
  • /37

    $85,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    1358 Crellin Underwood Rd, Oakland, MD 21550

    Charming 2-bedroom, 1-bath home offering a fantastic opportunity for buyers looking to add their own personal touch. Recent updates include a metal roof, 2 propane wall unit heaters, and a hot water heater. Enjoy the back covered deck overlooking the woods and the youghiogheny river below. This property needs a bit of TLC but is full of potential and character. Located in a highly desirable

    Lucas Muenchow Railey Realty, Inc.

    1358 Crellin Underwood Rd, Oakland, MD 21550
  • /31

    $130,000

    • Land
    • 2.1 Acres
    • $61,905 per Acre

    Lot 20 Paradise Ridge Rd, Oakland, MD 21550

    Discover the perfect setting for your mountain retreat in the Paradise Ridge community at Deep Creek Lake. This beautiful 2.10 acre wooded lot is tucked away on a quiet cul-de-sac, offering privacy, natural surroundings, and a peaceful atmosphere. The property has already been approved for a conventional septic system, making it an ideal choice for building your dream home or vacation getaway.

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 526-7577

    Lot 20 Paradise Ridge Rd, Oakland, MD 21550
  • /89

    $2,100,000

    • 6 Beds
    • 4.5 Baths
    • 3,882 Sq Ft

    209 Glendale Rd, Oakland, MD 21550

    If you're in the market for location, convenience, and rental income, this inviting 6 Bedroom 4.5 bath Lakefront home is calling for you! Located in the heart of the action on Deep Creek Lake, the 3 level chateau has been updated and upgraded both inside and out. Restaurants, the movie theatre, shopping and Deep Creek Lake State Park are all within walking distance. Offering an open layout with

    Bill Weissgerber Railey Realty, Inc.

    209 Glendale Rd, 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
  • /30

    $249,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,390 Sq Ft

    62 Wild Turkey Ct, Oakland, MD 21550

    Current new home construction project underway, but Builder not going to complete at this time due too busy. So, ready for who may wish to complete project themselves or have completed by others, or current Builder may consider completing for Buyer. Current structure is a custom engineered modular home. This is not a completed or intended by Builder to be completed house project at this time .

    Chip Smith 1 Real Estate Source LLC

    62 Wild Turkey Ct, Oakland, MD 21550
  • /32

    $309,000

    • 2 Beds
    • 1 Bath
    • 780 Sq Ft

    565 Glendale Rd Unit B206, Oakland, MD 21550

    Charming true 1-bedroom + loft (can be used as 2nd bedroom) condo at Silver Tree Suites, LAKEFRONT living at its finest! This spacious second-floor unit features a private balcony, fully equipped kitchenette, cozy gas fireplace and abundant natural light. Enjoy resort-style amenities including a fitness center, sauna, on-site laundry and game room, plus steps-away fine dining at Dutch’s at Silver

    Carlos Espinoza Jason Mitchell Group

    565 Glendale Rd Unit B206, Oakland, MD 21550
  • /9

    $3,500

    • Land
    • 0.48 Acre
    • $7,292 per Acre

    LOT 2 Beaver Run Rd, Oakland, MD 21550

    Tucked away in the stunning mountains of Western Maryland, this unbuildable lot provides a serene escape into nature, offering breathtaking views and abundant wildlife. Located in the Youghiogheny Mountain Resort, this membership-only lot grants exclusive access to over 50 miles of private roads and trails, ideal for ATV and side-by-side adventures. Resort amenities include a community clubhouse,

    Elizabeth Broadwater Taylor Made Deep Creek Real Estate

    LOT 2 Beaver Run Rd, Oakland, MD 21550
  • /17

    $765,000

    • 4 Beds
    • 3 Baths
    • 2,112 Sq Ft

    519 Paradise Heights, Oakland, MD 21550

    Secluded 4 bedroom 3 bath log home with lake access and single dock slip located in the heart of Deep Creek Lake Resort Area Full unfinished basement, front covered porch and rear deck. Call Office for particulares.

    Linda Deremer Appalachian Realty

    519 Paradise Heights, 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
  • /2

    $369,000

    • Land
    • 0.47 Acre
    • $785,106 per Acre

    8946 Oakland Sang Run Rd, Oakland, MD 21550

    There are 3 adjacent parcels included with this sale :Tax ID - 1206034144, 1206020860, 1206007082 All parcels together are 8 acres WARNING: The house on this property is condemned and ready for tear down. Enter at your own risk.

    Joe Zorzit Eagle Commercial Realty

    8946 Oakland Sang Run Rd, 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
  • /4

    $29,900

    • Land
    • 1.09 Acres
    • $27,431 per Acre

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550

    1+ acre building lot. Fairly leveled cleared lot with some distant mountain views. Paved County road frontage with private road/drive access to lot. Approved for private septic and well. Electric on-site. Located approx. 10+ mins from Deep Creek Lake and approx. less than 5 minutes from Oakland. Located within small 8 lot development, "The Homestead".

    Chip Smith 1 Real Estate Source LLC

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
  • /6

    $4,000

    • Land
    • 0.46 Acre
    • $8,696 per Acre

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550

    Here is an affordable chance to own a lot and have access to all of Youghiogheny Mountain Resort's beautiful and fun amenities!

    Jonathan Price Railey Realty, Inc.

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550

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