119

Oakland, MD Homes for Sale

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  • /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
  • /50

    $359,000

    • 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

    961 Cedar Ln, 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
    • 0.34 Acre
    • $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
  • /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
  • /53

    $355,000

    • 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
  • /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
  • /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
  • /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
  • /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
  • /10

    $199,900 Coming Soon

    • 2 Beds
    • 1 Bath
    • 1,492 Sq Ft

    207 Shenandoah Ave, Oakland, MD 21550

    Coming soon in Loch Lynn, this charming 2-bedroom, 1-bath home sits on a 0.25-acre lot and offers a private wood-fenced side yard and a covered sundeck patio perfect for relaxing or entertaining. The owners have thoughtfully updated the home over the years, featuring oak flooring throughout and a cozy pellet stove. Perfect for anyone looking for a move-in-ready home that’s both comfortable and

    Laura Newhall Taylor Made Deep Creek Real Estate

    207 Shenandoah Ave, Oakland, MD 21550
  • /3

    $875,000 Coming Soon

    • 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 3‐bedroom mountaintop chalet, set on 1.17 private acres with expansive outdoor entertainment space. Whether you're hosting friends or enjoying quiet mountain evenings, this home delivers an unforgettable retreat. Inside, the great room impresses with a soaring stacked‐stone fireplace. The primary bedroom features

    Brent Housley Railey Realty, Inc.

    891 Mountainview Dr, Oakland, MD 21550
  • /68

    $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
  • /43

    $325,000

    • 2 Beds
    • 2 Baths
    • 2,015 Sq Ft

    3749 Maryland Hwy, Oakland, MD 21550

    Set on a beautiful lot in Deep Creek, Maryland, this stunning property offers the perfect blend of privacy, relaxation, and investment potential. Currently enjoyed as a second home, the residence has also been successfully utilized as a partial Airbnb, generating approximately $28,000 in rental income last year. The home has been thoughtfully updated, creating a warm and inviting atmosphere with

    Jovan Vidulovic Keller Williams Realty

    3749 Maryland Hwy, 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
  • /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

    $314,000

    • 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
  • /59

    $220,000

    • 2 Beds
    • 1 Bath
    • 1,064 Sq Ft

    313 W Liberty St, Oakland, MD 21550

    Charming and meticulously maintained 1947 brick ranch located at the edge of Oakland town limits on a beautiful 1⁄4-acre lot. This 2-bedroom, 1-bath home features spacious rooms, natural gas heat, public utilities, and a full unfinished basement offering great storage or future potential. Ownership includes a 1⁄2 interest in a shared 2-car garage. Conveniently situated near schools, the hospital,

    Justin Liller Railey Realty, Inc.

    313 W Liberty St, Oakland, MD 21550
  • /19

    $289,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    226 N Hammond St, Oakland, MD 21550

    NEW CONSTRUCTION from Lyv Homes! This 2BR/2BA, 1000sf cottage is located in the historic 2nd Street area of Oakland and features modern design with elite finishes. Key features include Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets and drawers, quartz counters and range backsplash, shiplap backsplash accents, stainless steel Frigidaire

    Jay Ferguson Taylor Made Deep Creek Real Estate

    226 N Hammond St, Oakland, MD 21550
  • /82

    $865,000

    • 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,

    Melissa Long Railey Realty, Inc.

    1909 Pysell Crosscut Rd, Oakland, MD 21550
  • /60

    $174,900

    • 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
    • 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
  • /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
  • /19

    $239,700

    • 3 Beds
    • 3 Baths
    • 1,104 Sq Ft

    53 Bird Ave, Oakland, MD 21550

    Opportunity and a peaceful country setting on 1.55 acres in Deer Park. This 3BR, 2BA ranch offers 1,872 sq ft with solid bones and room to make it your own. The spacious kitchen with hickory cabinets, gas stove, and propane fireplace creates a warm gathering space at the heart of the home. Outside, several outbuildings—including a large shop and secondary wood shop with heat and electric, a

    Rachel Bruch Railey Realty, Inc.

    53 Bird Ave, Oakland, MD 21550
  • /9

    $49,900

    • Land
    • 1 Acre
    • $49,900 per Acre

    0 Longview Ln, Oakland, MD 21550

    1.00 Acre wooded lot loacted in George Brunson Subdivision. Close to Deep Creek Lake, Wisp Ski Resort and Oakland. Approved perc

    Linda Deremer Appalachian Realty

    0 Longview Ln, Oakland, MD 21550
  • /46

    $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
  • /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
  • /16

    $299,000

    • Land
    • 0 Acre

    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550

    Rare offering! LAKE VIEW building site with TWO BOAT SLIPS! Located off popular Lake Shore Drive in the Edgewater community, this lot features a building envelope surrounded by community green space. Deep water, somewhat flat area by the lake, feels like small little park area. Dock access is directly across the street and a short walk away away - 100 yards +/-. Paved parking area for easy

    Jay Ferguson Taylor Made Deep Creek Real Estate

    0 Edgewater Dr Unit 4 MDGA2009106, 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
  • /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
  • /47

    $1,199,000

    • 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

    $300,000

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

    8 Laurel Brook Dr, Oakland, MD 21550

    Fully renovated 2-bedroom, 2-bath condo is 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 feel.The thoughtfully redesigned interior offers an open-concept main floor with shiplap

    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
  • /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
  • /15

    $199,900

    • Land
    • 9.64 Acres
    • $20,737 per Acre

    0 8th & Dennett Road St Unit MDGA2009886, Oakland, MD 21550

    A rare opportunity to acquire a high-potential 9.64 acre parcel located in the heart of Oakland. The location is very close to schools, grocery stores, restaurants, hospital and shopping. This site offers an ideal setting for residential, mixed-use, multifamily, or commercial development (subject to zoning approval). Easy access to infrastructure, with public utilities nearby at the street. This

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    0 8th & Dennett Road St Unit MDGA2009886, 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

Showing Results 81 - 119, Page 3 of 3

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