Oakland, MD Homes for Sale with Acreage

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  /15

  $39,000

  • Land
  • 2.57 Acres
  • $15,175 per Acre

  lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550

  2 lots (7 & 8) totaling 2.57 acres, on gently sloping wooded area. Nestled between Cannan Valley & Deep Creek Lake, this promises to be a perfect blend of convenience and tranquility. Nature surrounds you - the perfect spot for a cozy cabin! Call agent for more information!

  Julie Mead The KW Collective

  lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
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  /51

  $434,900

  Open Fri 1PM - 4PM

  • 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
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  /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, LLC

  233 Rhododendron Dr, Oakland, MD 21550
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  /5

  $89,900

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

  0 15 75 Acres Bethlehem Rd Unit MDGA2011216, 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.

  0 15 75 Acres Bethlehem Rd Unit MDGA2011216, Oakland, MD 21550
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  /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
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  $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
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  /12

  $39,000

  • Land
  • 1.02 Acres
  • $38,235 per Acre

  Lot 14 Warnick Way, Oakland, MD 21550

  Enjoy scenic mountain views from this 1.02 acre mostly wooded homesite. This property offers a peaceful setting with convenient access off Spring Glade Road and is ideally located between Oakland and Deep Creek Lake. No HOA and mobile homes are not permitted, helping maintain the character of the area. Do not miss this great opportunity to build your getaway or full time residence. Contact me

  Nicole Jackson Railey Realty, Inc.

  Lot 14 Warnick Way, Oakland, MD 21550
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  /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
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  /50

  $339,000

  • 4 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  961 Cedar Ln, Oakland, MD 21550

  Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat offers privacy, comfort, and plenty of space to unwind. Step inside to find a warm and inviting main level highlighted by a stone fireplace, cozy dining area, and galley-style kitchen. Relax on the screened-in porch complete with a hot tub under roof, perfect for year-round enjoyment. The finished basement

  Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

  961 Cedar Ln, Oakland, MD 21550
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  /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
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  $769,900

  $30K PRICE DROP

  • 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
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  /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
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  /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
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  /8

  $100,000

  $100K PRICE DROP

  • Land
  • 5 Acres
  • $20,000 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
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  /2

  $84,369

  • Land
  • 1.72 Acres
  • $49,052 per Acre

  0 Quentin Ln, Oakland, MD 21550

  Nicely wooded 1.72 acre lot in the lake area. Level to gently sloping lot is ready for your house plans. Close to all lake activities and Wisp Resort. Lot is on a no outlet road.

  Kevin Liller Railey Realty, Inc.

  0 Quentin Ln, Oakland, MD 21550
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  $199,900

  • Land
  • 3.32 Acres
  • $60,211 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
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  $699,000

  • 5 Beds
  • 3 Baths
  • 2,560 Sq Ft

  170 Cherrywood Dr, Oakland, MD 21550

  Private Mountain Retreat on 8+ Acres Near Oakland Discover the peace and beauty of Garrett County living on over 8 private wooded acres filled with mountain views, abundant wildlife, and endless opportunities to enjoy the outdoors. Deer, turkey, songbirds, and other native wildlife are frequent visitors, creating a true nature lover's paradise. Conveniently located just minutes from Oakland's

  Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

  170 Cherrywood Dr, Oakland, MD 21550
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  /24

  $1,025,000

  $50K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  127 Paradise Heights, Oakland, MD 21550

  Beautifully renovated lake access log cabin with a deeded dock slip in a quiet cove with private 29 acres of trails (ATVs/snowmobiles permitted). Recent renovations (approx. $200K) include new wrap around deck, new roof, re-stained siding, new kitchen with granite counters, new appliances, new bathrooms, new LVFs throughout the house, new 2 car garage doors, new mini-split heat and A/C units, and

  Norman Domingo XRealty.NET LLC

  127 Paradise Heights, Oakland, MD 21550
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  /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
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  /82

  $760,000

  $105K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 2,970 Sq Ft

  1909 Pysell Crosscut Rd, Oakland, MD 21550

  Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just minutes from Deep Creek Lake and Oakland. This 4-bedroom, 4.5-bath home has been carefully updated to balance comfort, practicality, and modern style. The main level features hardwood floors, radiant heat for added comfort, and open gathering spaces with quiet nooks for reading or hobbies. Upstairs, two

  Melissa Long Railey Realty, Inc.

  1909 Pysell Crosscut Rd, Oakland, MD 21550
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  /28

  $79,500

  $3K PRICE DROP

  • Land
  • 2.53 Acres
  • $31,423 per Acre

  8760 Oakland Sang Run Rd, Oakland, MD 21550

  Attention outdoor enthusiasts! This 2.53 acre lot just across the road from state-owned land down to the world-famous Youghiogheny River is a whitewater lover or fisherman's dream. Complete with a gravel driveway up to a flat gravel pad and electric meter ready to go, perfect for a camper or a forever home. Perc-approved for 3 bedrooms and less than half a mile from easy public Yough access.

  Elizabeth Ware Railey Realty, Inc.

  8760 Oakland Sang Run Rd, Oakland, MD 21550
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  $285,500

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft

  1737 King Wildesen Rd, Oakland, MD 21550

  Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-sided home offers the perfect blend of rustic charm and modern comfort—all just 10 minutes from downtown Oakland. This well-maintained home features 3 spacious bedrooms and 2 full bathrooms, including a main floor master suite for added convenience. Inside, you’ll find brand-new luxury vinyl plank (LVP)

  Justin Liller Railey Realty, Inc.

  1737 King Wildesen Rd, Oakland, MD 21550
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  /37

  $279,000

  • 3 Beds
  • 1.5 Baths
  • 1,148 Sq Ft

  277 Cheeks Ln, Oakland, MD 21550

  Tucked away on a private lane and surrounded by the beauty of the woods, this charming 3-bedroom, 1 full bath and 1 half bath log home offers the perfect mountain retreat on 2 peaceful acres in Garrett County. Ideally located just minutes from Swallow Falls State Park, Muddy Creek Falls, and the Youghiogheny River, this cozy cabin is a dream destination for outdoor enthusiasts seeking hiking,

  Mike Kennedy Railey Realty, Inc.

  277 Cheeks Ln, Oakland, MD 21550
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  /30

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft

  98 Bear Run Rd, Oakland, MD 21550

  Make it your own! This 2-acre parcel comes with two additional parcels of 17.96 and 24.23 acres for a total of 42.19 acres. The 2-acre parcel is improved by a fully furnished (26’X42’), 3-bedroom, 2-bathroom Ranch style dwelling and a large parking area. The interior offers a spacious living room, and an eat-in kitchen with all appliances, furniture and window AC units. The land is un-zoned

  Dan (Sussan) Duggan 1 Real Estate Source LLC

  98 Bear Run Rd, Oakland, MD 21550
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  /55

  $400,000

  $120K PRICE INCREASE

  • Land
  • 43.72 Acres
  • $9,149 per Acre

  3257 George Washington Hwy, Oakland, MD 21550

  Discover approximately 43.72 acres of beautiful mostly 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. Set up with a well and septic system, this property is perfect to build your dream home with an already

  Justin Liller Railey Realty, Inc.

  3257 George Washington Hwy, Oakland, MD 21550
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  /70

  $1,189,000

  New Construction Open Sat 10AM - 12PM

  • 6 Beds
  • 5.5 Baths
  • 3,482 Sq Ft

  248 Tarn Dr, Oakland, MD 21550

  Brand new construction in the desirable Mountainside community! This thoughtfully designed 6-bedroom mountain retreat offers 4 spacious primary suites, blending modern mountain style with functionality and comfort throughout. The open floorplan features vaulted ceilings, luxury finishes, quartz countertops, and multiple gathering spaces designed for entertaining and relaxation alike. Enjoy cozy

  Lauren McCann Railey Realty, Inc.

  248 Tarn Dr, Oakland, MD 21550
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  /53

  $340,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  254 Little Mountain Rd, Oakland, MD 21550

  Escape to the mountains at 254 Little Mountain Road, where privacy, comfort, and outdoor adventure come together on nearly 5 acres in the sought-after Backbone Ridge community. Surrounded by mature trees and mountain scenery. Inside, you'll find warm wood accents and a cozy wood-burning fireplace that anchors the inviting living space. Multiple gathering areas provide flexibility for

  Amy Skipper Railey Realty, Inc.

  254 Little Mountain Rd, Oakland, MD 21550
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  /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
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  /6

  $19,900

  • Land
  • 1.35 Acres
  • $14,741 per Acre

  Lot 18 Buck Dr, Oakland, MD 21550

  This 1.352 acre lot borders Buck Drive and also Antelope Drive. It is best to access the lot using the directions provided via Antelope Drive as it is a much better road. Buck Drive is very difficult to traverse and access through Antelope Drive is recommended. Pictures of the lot are taken from Antelope Drive. Perc approved for a three bedroom home with a sand mound system. Wooded lot just

  Kevin Liller Railey Realty, Inc.

  Lot 18 Buck Dr, Oakland, MD 21550

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