151

Oakland, MD Homes for Sale

Section Image
  • 13 Birchwood Dr, Oakland, MD 21550
    13 Birchwood Dr, Oakland, MD 21550
    13 Birchwood Dr, Oakland, MD 21550
    /5

    $18,000

    • Land
    • 27,007 Sq Ft
    • $29,032 per Acre

    13 Birchwood Dr, Oakland, MD 21550

    Discover your own mountain escape in the gated community of Youghiogheny Mountain Resort! This 0.62-acre lot is perfect for building a dream home or weekend retreat, surrounded by miles of ATV trails, hunting, and fishing. Ideally located near Wisp Resort, Deep Creek Lake, Herrington Manor State Park, and Swallow Falls State Park, you’ll enjoy year-round outdoor adventure. Approved for a sand

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    13 Birchwood Dr, Oakland, MD 21550
  • 27 Gobbler Run Rd, Oakland, MD 21550
    27 Gobbler Run Rd, Oakland, MD 21550
    27 Gobbler Run Rd, Oakland, MD 21550
    /24

    $18,000

    • Land
    • 20,473 Sq Ft
    • $38,298 per Acre

    27 Gobbler Run Rd, Oakland, MD 21550

    Build your ideal mountain retreat in the gated community of Youghiogheny Mountain Resort! This level 0.47-acre lot offers an easy build site and is Health Department approved for a shallow trench gravity septic system. Enjoy access to ATV trails, hunting, and fishing, all just minutes from Wisp Resort, Deep Creek Lake, and Swallow Falls State Park. Whether you're planning a full-time home or

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    27 Gobbler Run Rd, Oakland, MD 21550
  • 5 Laurel Brook Dr, Oakland, MD 21550
    5 Laurel Brook Dr, Oakland, MD 21550
    5 Laurel Brook Dr, Oakland, MD 21550
    /29

    $269,900

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    5 Laurel Brook Dr, Oakland, MD 21550

    Major renovations on this 2BR, 2BA Laurel brook two level townhome! Updates include new flooring, paint, fixtures, countertops, bathrooms and furnishings. One of the best dollar for dollar values still available at Deep Creek Lake and located within one mile of shopping, dining, entertainment, marinas and more! Enjoy a park-like setting with mature trees, common areas for relaxing or picnics and

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    5 Laurel Brook Dr, Oakland, MD 21550
  • 233 Rhododendron Dr, Oakland, MD 21550
    233 Rhododendron Dr, Oakland, MD 21550
    233 Rhododendron Dr, 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, LLC

    233 Rhododendron Dr, Oakland, MD 21550
  • 0 15 75 Acres Bethlehem Rd Unit MDGA2011216, Oakland, MD 21550
    0 15 75 Acres Bethlehem Rd Unit MDGA2011216, Oakland, MD 21550
    0 15 75 Acres Bethlehem Rd Unit MDGA2011216, Oakland, MD 21550
    /5

    $89,900

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

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

    If you've been looking for a place to build while enjoying some peace and quiet, this 15.75± acre wooded property is worth a look. Tucked away off Bethlehem Road just minutes from town and close to the Potomac State Forest, it offers the privacy of a country setting without being far from everyday conveniences. One of the biggest advantages is the 7.02-acre buildable lot (Lot 8 on the recorded

    Thomas Long Railey Realty, Inc.

    0 15 75 Acres Bethlehem Rd Unit MDGA2011216, Oakland, MD 21550
  • 565 Glendale Rd Unit 303B, Oakland, MD 21550
    565 Glendale Rd Unit 303B, Oakland, MD 21550
    565 Glendale Rd Unit 303B, Oakland, MD 21550
    /34

    $399,900

    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    565 Glendale Rd Unit 303B, Oakland, MD 21550

    Experience lakefront living at its finest in the premier unit at Silver Tree Suites! This beautifully updated 2-bedroom, 1-bath condo showcases rustic charm with custom woodworking throughout. Featuring two separate living areas, there's plenty of space to relax and entertain. Enjoy year-round lake views from the private balcony, unwind by either of the two fireplaces, and appreciate the added

    Sean Sober Taylor-Made Deep Creek Real Estate, LLC

    565 Glendale Rd Unit 303B, Oakland, MD 21550
  • 482 Pergin Farm Rd, Oakland, MD 21550
    482 Pergin Farm Rd, Oakland, MD 21550
    482 Pergin Farm Rd, Oakland, MD 21550
    /55

    $449,000

    • 3 Beds
    • 1.5 Baths
    • 2,160 Sq Ft

    482 Pergin Farm Rd, Oakland, MD 21550

    Fall in love with the peaceful setting of this inviting log home nestled in the sought after Pergin Farm community at Deep Creek Lake. Surrounded by trees and tucked away in a quiet setting, this 3 bedroom, 1.5 bath home offers the warmth and character of a true mountain retreat with a layout that feels both comfortable and connected. Step inside through the welcoming mudroom, where the home

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    482 Pergin Farm Rd, Oakland, MD 21550
  • 22 Woodlands Hill Ln, Oakland, MD 21550
    22 Woodlands Hill Ln, Oakland, MD 21550
    22 Woodlands Hill Ln, Oakland, MD 21550
    /22

    $159,000

    • Land
    • 2.02 Acres
    • $78,713 per Acre

    22 Woodlands Hill Ln, Oakland, MD 21550

    2.02-acre wooded building lot in The View community at Deep Creek Lake. This beautiful parcel offers a private setting with plenty of room for your future mountain or lake area retreat. Seasonal mountain and lake views. 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

    Jon Bell Railey Realty, Inc.

    22 Woodlands Hill Ln, Oakland, MD 21550
  • 1529 Paradise Point Rd, Oakland, MD 21550
    1529 Paradise Point Rd, Oakland, MD 21550
    1529 Paradise Point Rd, Oakland, MD 21550
    /67

    $639,000

    • 3 Beds
    • 2.5 Baths
    • 1,933 Sq Ft

    1529 Paradise Point Rd, Oakland, MD 21550

    This exquisite Northern White Cedar Construction (naturally rot resistant) log home offers a harmonious blend of rustic charm and modern luxury. The spacious, open floor plan invites you to experience a warm and inviting atmosphere, accentuated by stunning wood floors and walls, cathedral beam ceiling, and a cozy stone fireplace with glass doors, perfect for intimate gatherings. The heart of the

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

    1529 Paradise Point Rd, Oakland, MD 21550
  • 187 Lower Penn Point Dr, Oakland, MD 21550
    187 Lower Penn Point Dr, Oakland, MD 21550
    187 Lower Penn Point Dr, Oakland, MD 21550
    /44

    $1,425,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,695 Sq Ft

    187 Lower Penn Point Dr, Oakland, MD 21550

    Cozy cottage with split lakefront and Type A dock located in the serene quiet Penn Point Cove. This quaint home has plenty of room for family, guests and entertaining. The covered & heated outdoor deck facing the lake is a great place for morning coffee and evening dinner. The large, bright kitchen & dining area is another great entertaining space with quartz countertops, stainless steel

    Amy Mangum Railey Realty, Inc.

    187 Lower Penn Point Dr, Oakland, MD 21550
  • 40 Sunshine Ln, Oakland, MD 21550
    40 Sunshine Ln, Oakland, MD 21550
    40 Sunshine Ln, Oakland, MD 21550
    /43

    $169,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,516 Sq Ft

    40 Sunshine Ln, Oakland, MD 21550

    Enjoy the charm of country living with the convenience of being in downtown Crellin!Situated on nearly an acre, this inviting 3-bedroom, 1-bath home offers a bright, open layout filled with natural light.The main level features a spacious bedroom surrounded by windows, creating a warm and welcoming retreat. Upstairs, you'll find two additional bedrooms that can easily accommodate

    Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

    40 Sunshine Ln, Oakland, MD 21550
  • 565 Glendale Rd Unit 306, Oakland, MD 21550
    565 Glendale Rd Unit 306, Oakland, MD 21550
    565 Glendale Rd Unit 306, 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
  • 1499 Foster Rd, Oakland, MD 21550
    1499 Foster Rd, Oakland, MD 21550
    1499 Foster Rd, Oakland, MD 21550
    /64

    $375,000

    $40K PRICE DROP
    • 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
  • 321 N 3rd St, Oakland, MD 21550
    321 N 3rd St, Oakland, MD 21550
    321 N 3rd St, Oakland, MD 21550
    /48

    $365,000

    $35K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 3,660 Sq Ft

    321 N 3rd St, Oakland, MD 21550

    Reduced and Ready to go!! Perfect one level retirement retreat or 2nd vacation home! Spacious and beautifully maintained all-brick rancher offering approximately 3,660 square feet of living space with room for everyone! This impressive home features 5 bedrooms, 2 full bathrooms, and a fully finished basement with its own private entrance—perfect for in-law potential, extended family living, or

    Christina Ford CENTURY 21 New Millennium

    321 N 3rd St, Oakland, MD 21550
  • 102 N 3rd St, Oakland, MD 21550
    102 N 3rd St, Oakland, MD 21550
    102 N 3rd St, Oakland, MD 21550
    /43

    $259,900

    • 3 Beds
    • 2 Baths
    • 1,998 Sq Ft

    102 N 3rd St, Oakland, MD 21550

    Very well maintained 3Br-2BA traditional style home in Oakland with huge 24X24 deck, paved driveway and one car detached garage. Home features almost 2000 square feet of living area, stainless steel appliances, and updated bathrooms. Great place to watch the Autumn Glory parade from you covered front porch. Hot water radiant heat with natural gas being the heat source. Newer replacement windows,

    Kevin Liller Railey Realty, Inc.

    102 N 3rd St, Oakland, MD 21550
  • 204 Farm View Ln, Oakland, MD 21550
    204 Farm View Ln, Oakland, MD 21550
    204 Farm View Ln, Oakland, MD 21550
    /73

    $540,000

    • 3 Beds
    • 3.5 Baths
    • 3,276 Sq Ft

    204 Farm View Ln, Oakland, MD 21550

    Welcome to your ultimate woodland retreat! Nestled in a private, serene setting, this meticulously maintained 3-bedroom, 3.5-bathroom log home perfectly blends rustic charm with modern luxury. Freshly painted throughout and boasting gleaming, well-maintained wide-plank hardwood floors and new carpeting, this property is completely turn-key. The heart of the home is the grand family room, which

    John McNamara RE/MAX Results

    204 Farm View Ln, Oakland, MD 21550
  • 333 Sloan Tract Rd, Oakland, MD 21550
    333 Sloan Tract Rd, Oakland, MD 21550
    333 Sloan Tract Rd, Oakland, MD 21550
    /61

    $444,700

    • 4 Beds
    • 3.5 Baths
    • 1,585 Sq Ft

    333 Sloan Tract Rd, Oakland, MD 21550

    Welcome to *HIDDEN TREASURES*, a beautifully appointed 4-bedroom, 3½-bath home offering the perfect Deep Creek Lake getaway! This established rental property is ideally located close to the lake’s many amenities, making it an excellent opportunity for both personal enjoyment and investment potential. Relax and unwind in the private hot tub after a day of boating, hiking, skiing, or exploring all

    Debra Beitzel Long & Foster Real Estate, Inc.

    333 Sloan Tract Rd, Oakland, MD 21550
  • Lot 54 Gallatin Spur Rd, Oakland, MD 21550
    Lot 54 Gallatin Spur Rd, Oakland, MD 21550
    Lot 54 Gallatin Spur 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
  • 181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    /25

    $249,900

    • 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
  • 560 Glendale Rd, Oakland, MD 21550
    560 Glendale Rd, Oakland, MD 21550
    560 Glendale Rd, Oakland, MD 21550
    /24

    $374,900

    $44K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    560 Glendale Rd, Oakland, MD 21550

    Charming vintage Deep Creek Lake log cabin ideally located in the heart of Deep Creek Lake just minutes from area amenities. Full of character and thoughtfully restored, this established rental property is being sold completely furnished and turnkey. Enjoy filtered lake views from the inviting covered front porch, then unwind in the hot tub or gather around the fire pit after a day on the lake.

    Lauren McCann Railey Realty, Inc.

    560 Glendale Rd, Oakland, MD 21550
  • 17240 Garrett Hwy, Oakland, MD 21550
    17240 Garrett Hwy, Oakland, MD 21550
    17240 Garrett Hwy, Oakland, MD 21550
    /104

    $899,000

    $99K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 5,547 Sq Ft

    17240 Garrett Hwy, Oakland, MD 21550

    Luxury Living Meets Timeless Country Charm! Perfectly positioned on 10.33 picturesque acres between Oakland and Deep Creek Lake, this exceptional 6-bedroom, 4.5-bath home offers the ideal blend of refined comfort, modern updates, and peaceful privacy.Step inside to discover an inviting open floor plan highlighted by soaring wood ceilings, a dramatic floor-to-ceiling stone fireplace, and

    Justin Liller Railey Realty, Inc.

    17240 Garrett Hwy, Oakland, MD 21550
  • Lot 14 Warnick Way, Oakland, MD 21550
    Lot 14 Warnick Way, Oakland, MD 21550
    Lot 14 Warnick Way, Oakland, MD 21550
    /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
  • 22 Elm Dr, Oakland, MD 21550
    22 Elm Dr, Oakland, MD 21550
    22 Elm Dr, Oakland, MD 21550
    /24

    $18,000

    • Land
    • 26,136 Sq Ft
    • $30,000 per Acre

    22 Elm Dr, Oakland, MD 21550

    Build your dream getaway in the gated community of Youghiogheny Mountain Resort! This flat 0.60-acre lot offers an ideal setting for easy building. Perfect for a full-time home or weekend retreat. Enjoy miles of ATV trails, hunting, and fishing, all while being just minutes from Wisp Resort, Deep Creek Lake, and Swallow Falls State Park. Approved for a sand mound septic system and located within

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    22 Elm Dr, Oakland, MD 21550
  • 0 Grey Squirrel Rd, Oakland, MD 21550
    0 Grey Squirrel Rd, Oakland, MD 21550
    0 Grey Squirrel Rd, Oakland, MD 21550
    /6

    $40,000

    • Land
    • 3.46 Acres
    • $11,561 per Acre

    0 Grey Squirrel Rd, Oakland, MD 21550

    Discover the perfect opportunity to own nearly 3.5 acres in the beautiful Youghiogheny Mountain Resort! This spacious vacant lot offers a peaceful mountain setting with plenty of room to create your ideal getaway, vacation retreat, or future home. Outdoor enthusiasts will love the recreational opportunities nearby, including 50+ miles of ATV riding, hiking, snowmobiling, fishing and hunting.

    Danielle Tasker Taylor-Made Deep Creek Real Estate, LLC

    0 Grey Squirrel Rd, Oakland, MD 21550
  • 961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    /56

    $299,000

    • 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
  • LOT 181 Santa fe Trail, Oakland, MD 21550
    LOT 181 Santa fe Trail, Oakland, MD 21550
    LOT 181 Santa fe Trail, 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
  • 0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
    0 Garrett Trail Unit MDGA2010758, 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
  • 467 Paradise Ridge Rd, Oakland, MD 21550
    467 Paradise Ridge Rd, Oakland, MD 21550
    467 Paradise Ridge Rd, Oakland, MD 21550
    /64

    $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 1.29 private acres, this 4-bedroom, 3.5-bath retreat offers 3,780 finished square feet, sweeping Deep Creek Lake and mountain views, lake access, abundant outdoor living, and an established vacation-rental history.The seller is

    Jon Bell Railey Realty, Inc.

    467 Paradise Ridge Rd, Oakland, MD 21550
  • 62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, 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
  • 315 Coolidge Ave, Oakland, MD 21550
    315 Coolidge Ave, Oakland, MD 21550
    315 Coolidge Ave, Oakland, MD 21550
    /53

    $264,500

    • 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, LLC

    315 Coolidge Ave, Oakland, MD 21550
  • 231 Santa fe Trail, Oakland, MD 21550
    231 Santa fe Trail, Oakland, MD 21550
    231 Santa fe Trail, Oakland, MD 21550
    /38

    $629,000

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

    231 Santa fe Trail, Oakland, MD 21550

    Brand new roof July 2026! 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

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    231 Santa fe Trail, Oakland, MD 21550
  • 449 S 3rd St, Oakland, MD 21550
    449 S 3rd St, Oakland, MD 21550
    449 S 3rd St, 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
  • 3500 Area Maryland Hwy, Oakland, MD 21550
    3500 Area Maryland Hwy, Oakland, MD 21550
    3500 Area Maryland Hwy, Oakland, MD 21550
    /5

    $90,000

    $110K PRICE DROP
    • Land
    • 5 Acres
    • $18,000 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
  • 0 Cedar Ln Unit MDGA2012732, Oakland, MD 21550
    0 Cedar Ln Unit MDGA2012732, Oakland, MD 21550
    0 Cedar Ln Unit MDGA2012732, Oakland, MD 21550
    /12

    $6,500

    • Land
    • 40,946 Sq Ft
    • $6,915 per Acre

    0 Cedar Ln Unit MDGA2012732, Oakland, MD 21550

    Discover this quiet .94 acre lot in the sought-after Yough Mountain Resort community, ideal for a mountain getaway, full-time home, or adventure basecamp. Enjoy access to over 2,000 acres of private wilderness, private hunting and fishing areas, ATV and snowmobile trails, community pavilions, playgrounds, sports courts, and green space, just minutes from Deep Creek Lake and Wisp Resort. A rare

    Shannon McWilliams Taylor-Made Deep Creek Real Estate, LLC

    0 Cedar Ln Unit MDGA2012732, Oakland, MD 21550
  • 395 Woodlands Hill Ln, Oakland, MD 21550
    395 Woodlands Hill Ln, Oakland, MD 21550
    395 Woodlands Hill Ln, Oakland, MD 21550
    /66

    $899,900

    • 5 Beds
    • 6 Baths
    • 3,160 Sq Ft

    395 Woodlands Hill Ln, Oakland, MD 21550

    Welcome to Happy Hoursss... Hideaway, a stunning Deep Creek Lake retreat where breathtaking views, upscale amenities, and spacious indoor-outdoor living create the perfect getaway. With 5 bedrooms and 6 full bathrooms, this beautifully appointed home comfortably accommodates family and friends while offering plenty of room to relax and entertain. The main level features an inviting open-concept

    Jon Bell Railey Realty, Inc.

    395 Woodlands Hill Ln, Oakland, MD 21550
  • 251 Robinwood Dr, Oakland, MD 21550
    251 Robinwood Dr, Oakland, MD 21550
    251 Robinwood Dr, 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
  • 1407 Broadford Rd, Oakland, MD 21550
    1407 Broadford Rd, Oakland, MD 21550
    1407 Broadford Rd, Oakland, MD 21550
    /52

    $399,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    1407 Broadford Rd, Oakland, MD 21550

    Welcome to this beautifully crafted new construction home, where modern comfort meets thoughtful design in an unbeatable location. From the moment you step inside, you'll appreciate the spacious layout, quality finishes, cathedral ceilings, and abundance of natural light throughout. The heart of the home is the spacious kitchen, featuring crisp white cabinetry, warm natural wood butcher-block

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    1407 Broadford Rd, Oakland, MD 21550
  • 0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
    0 Lake Shore Dr Unit MDGA2010464, 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
  • 20160 Garrett Hwy Unit 105A, Oakland, MD 21550
    20160 Garrett Hwy Unit 105A, Oakland, MD 21550
    20160 Garrett Hwy Unit 105A, Oakland, MD 21550
    /25

    $296,500

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft

    20160 Garrett Hwy Unit 105A, Oakland, MD 21550

    Will O the Wisp unit 105A is a charming one-bedroom, one-bath lakefront condominium. Unit 105A offers convenient first-floor living with ground-level access from a private patio directly to the waters edge, beach area and docks. . The unit features a fully equipped kitchen, comfortable living and dining areas, a cozy fireplace, one queen bed, and a sleeper sofa—accommodating up to three

    Rich Orr Railey Realty, Inc.

    20160 Garrett Hwy Unit 105A, Oakland, MD 21550
  • 565 Glendale Rd Unit B206, Oakland, MD 21550
    565 Glendale Rd Unit B206, Oakland, MD 21550
    565 Glendale Rd Unit B206, Oakland, MD 21550
    /32

    $299,900

    $29K 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

Showing Results 81 - 120, Page 3 of 4

Maryland Garrett County

Real Estate & Homes for Sale in Oakland, MD

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group