157

Oakland, MD Homes for Sale

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  • /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

    $3,000

    • Land
    • 24,393 Sq Ft
    • $5,357 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, LLC

    Lot 40 Fawn Dr, Oakland, MD 21550
  • /5

    $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
  • /62

    $775,000

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

    251 Robinwood Dr, Oakland, MD 21550

    One-of-a-kind Youghiogheny riverfront estate offering 224 feet of water frontage . 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 ceiling fireplace, log accent

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    251 Robinwood Dr, Oakland, MD 21550
  • /13

    $34,900

    • 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
  • /28

    $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
  • /69

    $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
  • /32

    $304,000

    $25K PRICE DROP
    • 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
  • /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
  • /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
  • /21

    $99,000

    • Land
    • 1.84 Acres
    • $53,804 per Acre

    0 Robinwood Dr Unit 13, Oakland, MD 21550

    RARE opportunity to own a Youghiogheny river access lot! Lot 13 is a 1.84 AC building lot with seasonal & filtered views of the water. River Run is an exclusive and highly sought-after waterfront community with a common access area that feels like a private park setting. Benches & picnic tables adorn a grassy, mostly level shoreline area along the river. Lot is perc approved for a three bedroom

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    0 Robinwood Dr Unit 13, Oakland, MD 21550
  • /2

    $799,900

    New Construction Coming Soon
    • 4 Beds
    • 4 Baths

    15 Byran Dr, Oakland, MD 21550

    Experience modern mountain living in this brand-new 2026 construction. This beautifully designed 4-bedroom, 4-bath home offers two spacious levels, quality finishes, and plenty of room for family and guests. Open layout with modern kitchen, island bar, and stone fireplace. Stamped concrete patio with covered fireplace and outdoor kitchen. Over half an acre of private wooded mountain-top space

    Jon Bell Railey Realty, Inc.

    15 Byran Dr, Oakland, MD 21550
  • /6

    $175,000

    • Land
    • 3.46 Acres
    • $50,578 per Acre

    0 Robinwood Dr Unit 9, Oakland, MD 21550

    Rare riverfront building lot on the Youghiogheny river offering 175+ feet of water frontage on 3.46 acres. Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. Enjoy a picturesque setting in a riverfront setting with NO HOA restraints. Perc approved. While parts of this lot may be in the flood plain, the

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    0 Robinwood Dr Unit 9, Oakland, MD 21550
  • /64

    $1,400,000

    • 5 Beds
    • 3.5 Baths
    • 2,832 Sq Ft

    827 Penn Point Rd, Oakland, MD 21550

    Custom built by the original owners and thoughtfully expanded with a recent addition, this exceptional five-bedroom, 3.5-bath home is set on 100 feet of split lakefront in desirable Penn Cove. Featuring a coveted Type A dock permit, lakeside fire pit and pavilion, and easy shoreline access, the property is designed to embrace lake living in every season. Set on a generously sized lot with

    Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    827 Penn Point Rd, Oakland, MD 21550
  • /57

    $595,000

    Open House 8/09
    • 2 Beds
    • 2 Baths
    • 1,340 Sq Ft

    193 Red Run Rd Unit 1B3, Oakland, MD 21550

    Ultimate lakefront living awaits at Red Run! This stunning 2-3BR, 2BA condo features a second-floor loft and a versatile den easily used as a 3rd bedroom. Enjoy breathtaking lake views from your gorgeous primary suite and private lakeside balcony. Extensively upgraded with a extensively upgraded kitchen boasting granite countertops and soft-close cabinetry, a newly remodeled laundry room with a

    John McNamara RE/MAX Results

    193 Red Run Rd Unit 1B3, Oakland, MD 21550
  • /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
  • /60

    $164,000

    • 3 Beds
    • 1 Bath
    • 816 Sq Ft

    63 Wallman Rd, Oakland, MD 21550

    Remodeled Rancher Near the North Branch Potomac RiverThis charming 3-bedroom, 1-bath rancher has been completely remodeled, with all new appliances. Located within walking distance of the scenic North Branch of the Potomac River, the home offers both convenience and natural beauty at your doorstep.A recently enclosed front porch with a wood stove provides extra warmth and a welcoming spot

    Rich Orr Railey Realty, Inc.

    63 Wallman Rd, Oakland, MD 21550
  • /9

    $3,500

    • Land
    • 20,908 Sq Ft
    • $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 throughout the community, as well as an abundance 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

    Elizabeth Broadwater Taylor-Made Deep Creek Real Estate, LLC

    LOT 2 Beaver Run Rd, 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, LLC

    25 Silver Tree Ln, Oakland, MD 21550
  • /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
  • /27

    $259,000

    • Land
    • 42 Acres
    • $6,167 per Acre

    Lot B Loch Deer Rd, Oakland, MD 21550

    42 Acres of un-zoned mostly wooded property located near Oakland and Deep Creek Lake MD. The property offers great opportunities for a variety of uses and also provides great views. Access to the property is off of Garrett Road via Loch Deer Road. The property has been surveyed.

    Bill Weissgerber Railey Realty, Inc.

    Lot B Loch Deer Rd, Oakland, MD 21550
  • /5

    $19,900

    • Land
    • 1.05 Acres
    • $18,952 per Acre

    0 Bear Dr E Unit MDGA2012426, Oakland, MD 21550

    Build your dream home, or vacation home. This development has 50 miles of private roads and trails perfect for ATV riding, UTVs, dirt bikes, hiking, hunting and outdoor recreation.

    Connie Leprevost Long & Foster Real Estate, Inc.

    0 Bear Dr E Unit MDGA2012426, 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, LLC

    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550
  • /45

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 2,548 Sq Ft

    995 Betts Ln, Oakland, MD 21550

    4BR 2.5BA cabin in the woods! Over 12 wooded acres of privacy and seclusion, laced with trails and surrounded by low maintenance land. Centrally located - only a few miles to Deep Creek Lake, town of Oakland or Swallow Falls State Park. Open floor plan with vaulted ceilings, a wood burning stove and high end finishes throughout. Basement is partially finished. Spacious decking and a must-have

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    995 Betts Ln, Oakland, MD 21550
  • /15

    $149,000

    • Land
    • 3.29 Acres
    • $45,289 per Acre

    16 Woodlands Hill Ct, Oakland, MD 21550

    3.29-acre wooded building lot in The View community at Deep Creek Lake. This spacious parcel offers a private setting with plenty of room for your future mountain or lake area retreat. Conveniently located off Lakeshore Drive and just minutes from Deep Creek Lake, Wisp Resort, restaurants, shopping, and other area amenities. Enjoy the perfect combination of privacy and convenience in one of the

    Jon Bell Railey Realty, Inc.

    16 Woodlands Hill Ct, Oakland, MD 21550
  • /49

    $379,500

    • 1 Bed
    • 1 Bath
    • 636 Sq Ft

    20160 Garrett Hwy Unit C307, Oakland, MD 21550

    Experience the best of Deep Creek Lake from this beautifully situated 2-story, 1-bedroom, 1-bath condominium at Will O' The Wisp. Offering 636 square feet of comfortable living space and spectacular lake views, this waterfront retreat is the perfect personal getaway, year-round residence, or vacation rental investment. Enjoy your morning coffee while taking in panoramic views of the water, then

    Justin Liller Railey Realty, Inc.

    20160 Garrett Hwy Unit C307, Oakland, MD 21550
  • /56

    $745,000

    • 5 Beds
    • 3 Baths
    • 2,640 Sq Ft

    638 Glendale Rd, Oakland, MD 21550

    Spacious five-bedroom lakeview home offering the perfect blend of relaxation and warmth from the moment you enter. This established rental property “Terp’s Hideaway” features an open and inviting floorplan, five bedrooms, two family rooms, and three levels of living space, making it an ideal layout for hosting family and friends. Step outside onto the large deck to take in beautiful views or

    Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    638 Glendale Rd, Oakland, MD 21550
  • /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
  • /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
  • /21

    $599,900

    • Land
    • 18.87 Acres
    • $31,791 per Acre

    0 Boy Scout Rd Unit MDGA2012474, Oakland, MD 21550

    An exceptional opportunity to own 18.87 acres in one of Deep Creek Lake's most desirable locations. Featuring 8 approved perc sites, this lake access property offers outstanding potential for a private estate, luxury mountain retreat, or future subdivision with the possibility of up to 8 homesites. Ideally situated on Boy Scout Road, the property provides the perfect balance of privacy and

    Jon Bell Railey Realty, Inc.

    0 Boy Scout Rd Unit MDGA2012474, 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
  • /42

    $269,000

    $31K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 560 Sq Ft

    400 Bear Dr E, Oakland, MD 21550

    Tucked away in the scenic beauty of Yough Mountain Resort, this exceptional 2-bedroom, 2-bath log cabin offers the perfect blend of rustic charm and modern comfort. Spanning two stories, this immaculately maintained home has seen thoughtful renovations in recent years, creating a warm and inviting retreat that’s move-in ready. Step inside to discover cozy living spaces ideal for relaxing after a

    Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

    400 Bear Dr E, Oakland, MD 21550
  • /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
  • /33

    $1,200,000

    • 2 Beds
    • 2.5 Baths
    • 2,914 Sq Ft

    826 G Swauger Rd, Oakland, MD 21550

    A Rare Fine Indeed! The private, end of the road farm is located in the much-desired Pleasant Valley area of southern Garrett County, MD.Built in 1933 and remodeled in 2020, this farmhouse is a must see. The inviting living area is complemented by a wood burning stove, while a LP gas furnace provides hot water radiant heat throughout the home. The kitchen features concrete countertops and is

    Larry Roth Railey Realty, Inc.

    826 G Swauger Rd, Oakland, MD 21550
  • /26

    $460,000

    Coming Soon
    • 5 Beds
    • 2 Baths
    • 2,860 Sq Ft

    5154 Maryland Hwy, Oakland, MD 21550

    Escape to the tranquility of country living in this spacious 5-bedroom, 2-bath home nestled on over 2 acres and conveniently located just minutes from the recreational opportunities of Deep Creek Lake and the charming town of Oakland, The property offers the perfect combination of peaceful country living and easy access to shopping, dining, and year-round activities. The kitchen has been

    Charlene Deremer Aburn Coldwell Banker Home Town Realty

    5154 Maryland Hwy, Oakland, MD 21550
  • /2

    $309,000

    $60K PRICE DROP
    • Land
    • 20,473 Sq Ft
    • $657,447 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
  • /65

    $799,000

    • 4 Beds
    • 3.5 Baths
    • 3,376 Sq Ft

    325 Markwood Dr, Oakland, MD 21550

    LAKEFRONT 4BR, 3.5BA log home with over 3300sf and 4.35 acres of privacy! Lovingly maintained property with gorgeous views of the 10 acre lake from almost every room in the house! Peaceful surroundings with towering mature trees and just enough yard space in a very laid back, rural setting near Herrington Manor and Swallow Falls state parks. If that weren't impressive enough, Meadow Lake Estates

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    325 Markwood Dr, Oakland, MD 21550

Showing Results 121 - 157, Page 4 of 4

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