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Oakland Homes for Sale

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  • /23

    $44,900

    • Land
    • 25,700 Sq Ft
    • $76,102 per Acre

    LOT 13 Bray Run Rd, 14, West Oakland, MD 21550

    Build your dream home or vacation retreat on this beautiful 0.59 acre lot in Bray Run! Just a short drive to the Deep Creek Lake area, you’ll have easy access to boating, paddling, fishing, and state park facilities. This ready to build site is part of a peaceful mountain community offering excellent amenities. Enjoy a playground, basketball court, scenic hiking trails, and the beauty of Bray Run

    Nicole Jackson Railey Realty, Inc.

    LOT 13 Bray Run Rd, 14, West 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
  • /28

    $120,000

    • 2 Beds
    • 1 Bath
    • 1,029 Sq Ft

    5151 Hutton Rd, Oakland, MD 21550

    Nearly an acre convenient to town - Some upgrades; newer metal roof, electrical panel box, furnace and other areas - Rear carport/patio area has easy at level access to main level - Large front porch with low maintenance entry area with wash/dryer hook-up - Good one level living layout - Sold as-is - No utilities currently active - No repairs before purchase or a lending requirement

    Mark Van Tyne Julian Agency Real Estate

    5151 Hutton Rd, Oakland, MD 21550
  • /5

    $34,000

    • Land
    • 2.92 Acres
    • $11,644 per Acre

    0 Yough View Dr Unit 12 MDGA2009840, 14, West Oakland, MD 21550

    Youghiogheny River access! LOT 12 is a 2.9 acre lot with private STREAM in the gated community of Timbers on the Yough. Mature pines, evergreens, and hardwoods. Riverfront community common area. Conveniently located only minutes from downtown Oakland and the Deep Creek Lake area. Perc tested and approved for a 3BR dwelling.

    Jay Ferguson Taylor Made Deep Creek Real Estate

    0 Yough View Dr Unit 12 MDGA2009840, 14, West Oakland, MD 21550
  • /32

    $249,900

    • 2 Beds
    • 1 Bath
    • 772 Sq Ft

    565 Glendale Rd Unit 306, Oakland, MD 21550

    Experience the best of Deep Creek Lake living from this beautifully appointed studio loft at Silver Tree Suites—one of the lake’s most sought-after locations! Offering two separate sleeping areas, a kitchenette, gas fireplace, and private balcony, this unit is designed for comfort and easy getaway living. Tastefully updated with new carpet and flooring, as well as kitchen and bathroom

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 306, 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
  • /5

    $27,500

    • Land
    • 0 Sq Ft

    Lot 54 Gallatin Spur Rd, Oakland, MD 21550

    Building lot located in the premier subdivision - Gallatin Woods! This beautifully wooded community is located in the heart of the Deep Creek Lake. This is a condominium ownership type in regards to the land itself, but is buildable for a single family home! There are 8 pre-approved building plans designed and engineered by Mountaineer Log Homes that range anywhere from 1571 to 3908 square feet.

    Nina Beitzel Railey Realty, Inc.

    Lot 54 Gallatin Spur Rd, Oakland, MD 21550
  • /25

    $259,900

    • 2 Beds
    • 1 Bath
    • 670 Sq Ft

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550

    Discover comfort and convenience in this charming 2-bedroom, 1-bath unit ideally located in the desirable Roman Ridge at Traders Landing community. Enjoy peaceful lake views from your covered front deck—the perfect spot to relax with your morning coffee or unwind in the evening. Inside, you’ll find a warm and inviting living space featuring a wood-burning fireplace to take the chill off during

    Larry Smith Railey Realty, Inc.

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
  • /71

    $1,049,000

    • 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

    137 Paradise Gardens Rd, Oakland, MD 21550
  • /5

    $25,000

    • Land
    • 14,810 Sq Ft
    • $73,529 per Acre

    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550

    Love Deep Creek Lake living. This 0.34 acre wooded lot sits near the heart of everything that makes the lake special. Launch the boat at nearby marinas, hike and swim at Deep Creek Lake State Park, and enjoy four season adventure at Wisp Resort with skiing, tubing, and mountain rides. Restaurants, shops, and local events are just down the road, while your homesite feels peaceful and private. Do

    Debra Hayne Cummings & Co. Realtors

    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
  • /3

    $45,900

    • Land
    • 1.02 Acres
    • $45,000 per Acre

    Lot 14 Warnick Way, Oakland, MD 21550

    Enjoy mountain views from this 1.02-acre, mostly wooded lot! No mobile homes permitted. No HOA. Easy access off Spring Glade Rd. Ideally situated between Oakland and Deep Creek Lake. Contact me today for more info!

    Nicole Jackson Railey Realty, Inc.

    Lot 14 Warnick Way, 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
  • /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
  • /12

    $45,000

    • Land
    • 14,810 Sq Ft
    • $132,353 per Acre

    LOT 181 Santa fe Trail, Oakland, MD 21550

    Don't miss the opportunity to own a lake area lot near the one and only Deep Creek Lake. 0.34 acre wooded lot, close to multiple local attractions. Call today! Verify utilities with Garrett County Environmental Department. Being sold subject to successful perc.

    Amy Skipper Railey Realty, Inc.

    LOT 181 Santa fe Trail, 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
  • /11

    $122,500

    • Land
    • 13.57 Acres
    • $9,027 per Acre

    Lot 3 Deer Run Rd, 14, West Oakland, MD 21550

    Rare Opportunity in Youghiogheny Mountain Resort – 13.57 Acres on Deer Run RoadThis is a unique chance to own a substantial 13.57-acre parcel in Youghiogheny Mountain Resort (YMR), a private, gated community where most lots have already been subdivided into much smaller parcels. Whether you're seeking privacy, recreation, or a place to build your dream home or cabin, Lot 3 on Deer Run

    Thomas Long Railey Realty, Inc.

    Lot 3 Deer Run Rd, 14, West 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
  • /53

    $269,500

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    315 Coolidge Ave, Oakland, MD 21550

    Well maintained brick rancher located in the heart of Oakland. This home offers a large kitchen open to the living room with a built-in fireplace, separate dining room, and new carpet through out. The basement is very clean, offering a clean slate for whatever you would like to do. The rear covered porch, deck and fenced in yard makes a great space to enjoy family and friends. The location is

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    315 Coolidge Ave, Oakland, MD 21550
  • /28

    $335,000

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

    1740 Old Crellin Rd, Oakland, MD 21550

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

    Andrew Orr The KW Collective

    1740 Old Crellin Rd, Oakland, MD 21550
  • /53

    $260,000

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 103B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites! This inviting one-bedroom layout features a gas fireplace, full bath with tub/shower, and a tidy kitchenette equipped with a microwave, dishwasher, and full-size refrigerator. Balcony doors open to fresh Deep Creek air and filtered lake views, with a private deck that is perfect for relaxing after a day on the water. Enjoy a variety of

    Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 103B, Oakland, MD 21550
  • /38

    $389,000

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    20160 Garrett Hwy Unit G507, Oakland, MD 21550

    Experience lakefront living with this charming two-level condo at Will O the Wisp at Deep Creek Lake! Offering 2 bedrooms and 1 full bathroom, it captures breathtaking lake views from both levels. The main floor features a functional kitchen and a cozy living area with a wood-burning fireplace—perfect for relaxing after a day on the water. Upstairs, you’ll find two comfortable bedrooms and a full

    Nina Beitzel Railey Realty, Inc.

    20160 Garrett Hwy Unit G507, 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
  • /82

    $875,000

    • 3 Beds
    • 4 Baths
    • 3,990 Sq Ft

    891 Mountainview Dr, Oakland, MD 21550

    Discover the perfect blend of rustic charm and modern comfort in this inviting turnkey 3‐bedroom mountaintop chalet with lake access, set on 1.17 private acres with expansive outdoor entertainment space. Whether you're hosting friends or enjoying quiet mountain evenings, this fully-furnished home delivers an unforgettable retreat. Inside, the great room impresses with a soaring stacked‐stone

    Brent Housley Railey Realty, Inc.

    891 Mountainview Dr, Oakland, MD 21550
  • /64

    $275,900

    • 4 Beds
    • 2 Baths
    • 1,928 Sq Ft

    449 S 3rd St, Oakland, MD 21550

    Welcome to this beautifully updated 1901 home in the heart of downtown Oakland, where historic character meets modern convenience. Situated on a charming lot with mature landscaping and blooming trees, this home offers timeless curb appeal with a welcoming covered front porch perfect for relaxing and enjoying the neighborhood. Inside, you’ll find modern updates throughout while preserving classic

    Justin Liller Railey Realty, Inc.

    449 S 3rd St, Oakland, MD 21550
  • /18

    $3,500

    • Land
    • 24,393 Sq Ft
    • $6,250 per Acre

    Lot 40 Fawn Dr, Oakland, MD 21550

    Lot 40 Fawn Drive is a 0.56-acre wooded, NON-BUILDABLE membership lot located in Youghiogheny Mountain Resort community in Oakland, MD. 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 outdoor enthusiasts seeking a private escape

    Shannon McWilliams Taylor Made Deep Creek Real Estate

    Lot 40 Fawn Dr, Oakland, MD 21550
  • /8

    $200,000

    • Land
    • 5 Acres
    • $40,000 per Acre

    3500 Area Maryland Hwy, Oakland, MD 21550

    The parcel is being sold by an estate. Wooded vacant land located at the 3400 area of Maryland Highway, Route 135. There is no record of Perc test on file at the Garrett County Health Department.

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    3500 Area Maryland Hwy, Oakland, MD 21550
  • /59

    $875,000 Coming Soon

    • 3 Beds
    • 3.5 Baths
    • 3,897 Sq Ft

    39 Leo Friend Rd, Oakland, MD 21550

    Stunning split lakefront retreat with sweeping views and Type-A dock. Experience exceptional lake life in this beautifully maintained one owner home offering breathtaking lake views and timeless craftsmanship in a serene landscaped setting. This impressive 3 bedroom 3.5 bathroom residence welcomes you through an elegant foyer with soaring cathedral ceilings and a striking oak staircase that sets

    Laura Newhall Taylor Made Deep Creek Real Estate

    39 Leo Friend Rd, Oakland, MD 21550
  • /3

    $150,000

    • Land
    • 3.4 Acres
    • $44,118 per Acre

    3.35 acres </> 4th St, Oakland, MD 21550

    Just over three acres in a prime location in Oakland, Maryland. Property borders the south side of Wal-Mart property and has deeded access from the south entrance of Wal-Mart. Property is wooded but has several flat spots perfect for building. Owner has hired a civil engineer to draw plans for a restaurant, and an office building. Plans are available for review.

    Andrew Orr The KW Collective

    3.35 acres </> 4th St, Oakland, MD 21550
  • /2

    $34,900 Coming Soon

    • 3 Beds
    • 1 Bath
    • 1,920 Sq Ft

    3482 Oakland Sang Run Rd, Oakland, MD 21550

    Situated in a prime location just minutes from Wisp Resort and Deep Creek Lake. The value here is in the land and location. With nearly one acre, the property offers strong potential to build a custom home or vacation retreat in a highly desirable area. This home is in very poor condition. Do not enter the home or step onto the front porch, as both are unsafe. This property is ready for a buyer

    Casey Oleynikov Pearson Smith Realty, LLC

    3482 Oakland Sang Run Rd, Oakland, MD 21550
  • /24

    $248,500

    • Land
    • 3.32 Acres
    • $74,849 per Acre

    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550

    OAKLAND, MD – 3.318 UNRESTRICTED ACRES “READY TO BUILD” THAT VACATION HOME OR FULL TIME RESIDENCE. THE SUBJECT PROPERTY IS IN THE DEEP CREEK LAKE RESORT AREA. ALL AMENITIES ASSOCIATED WITH A MAJOR RESORT AREA ARE WITHIN A SHORT DRIVE OF THE SUBJECT PROPERTY. FULLY WOODED. MATURE HARDWOOD THRU-OUT. LEVEL TOPOGRAPHY. CLOSE PROXIMITY TO BOAT LAUNCH.

    Mike Haywood The Mike Haywood Group

    0 Lake Shore Dr Unit MDGA2010464, 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
  • /28

    $160,000

    • Land
    • 3.04 Acres
    • $52,632 per Acre

    132 &132A Tarn Dr, Oakland, MD 21550

    Lake Access Lots 132 & 132A in the Mountainside Community offer 3.04 acres of privacy at the end of a quiet cul-de-sac on Tarn Drive. Combined and recorded in the land records as one building site, this property is already serviced by public water and sewer—making it ready for your future build. The gently wooded setting provides a peaceful, natural backdrop with plenty of space to design your

    Rich Orr Railey Realty, Inc.

    132 &132A Tarn Dr, Oakland, MD 21550
  • /20

    $60,000

    • Land
    • 22,215 Sq Ft
    • $117,647 per Acre

    0 Whispering Pines Ln Unit MDGA2010384, 14, West Oakland, MD 21550

    Enjoy the privacy of this location, and build your dream "cabin in the woods" on this .51 acre lot, with the Youghiogheny River and Swallow Falls State Park so close by! This lot is approved for a sand mound system and has a 3-bedroom perc. DISCLOSURE: RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. PROSPECTIVE PURCHASERS AND THEIR AGENTS ASSUME ALL LIABILITY ON ENTERING THE

    Kathy Gibson Railey Realty, Inc.

    0 Whispering Pines Ln Unit MDGA2010384, 14, West 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
  • /52

    $749,900

    • 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 with an available home warranty. 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

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    25 Silver Tree Ln, Oakland, MD 21550
  • /22

    $294,999

    • 2 Beds
    • 1 Bath
    • 2,344 Sq Ft

    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550

    Experience the best of lakeview living in this great condo at Deep Creek Lake. Offering two bedrooms, a fireplace and a lower-level family room for your enjoyment. Wake up to peaceful water views and enjoy ample space for everyday comfort and entertaining. The location is another plus, within walking distance to coffee shop, dining, and shopping. A perfect blend of size, scenery, and value!

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    135 Jeffrey Ln Unit 19-A, 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
  • /47

    $1,149,800

    • 5 Beds
    • 4.5 Baths
    • 2,593 Sq Ft

    285 Lake Shore Dr, Oakland, MD 21550

    Nestled on 1.52 private acres with 500 feet of frontage on Deep Creek Lake, this 5-bedroom, 4.5-bath home combines comfort with exceptional waterfront living. The open floor plan features soaring two-story ceilings with exposed beams, wood flooring, upgraded countertops, and a striking brick fireplace. Outdoor spaces include multiple decks, balconies, porches, and a hot tub—perfect for

    Terring Wang Keller Williams Capital Properties

    285 Lake Shore Dr, 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
  • /5

    $124,900

    • Land
    • 1.02 Acres
    • $122,451 per Acre

    Lot 53 Mountainview Dr, Oakland, MD 21550

    Ready to build lot in Deep Creek Lake's Mountainside Subdivision. This wooded lot is relatively level can be connected to public water and has an approved percolation test for an onsite septic system. Build you dream home in this mountaintop community with homes values ranging up to $2,000,000.

    Richard Saunders Samson Properties

    Lot 53 Mountainview Dr, Oakland, MD 21550

Showing Results 41 - 80, Page 2 of 3

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