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14 Laurel Brook Dr Unit 14, Oakland
$262,500
2 Beds ⋅ 2 Baths
Welcome to this beautifully maintained 2-bedroom, 2-bath end-unit located in the desirable Laurel Brook community, perfectly situated near all lake activities and amenities. This larger end unit offers additional deck space off the primary bedroom, ideal for relaxing or entertaining after a day on the water. The home has been well cared for and thoughtfully upgraded, including the addition of a mini-split system for efficient supplemental heating and air conditioning. Inside, you’ll find a comfortable and functional layout suited for both everyday living and hosting guests. A standout feature is the large unfinished storage area beneath the unit, providing ample space for lake gear, seasonal items, or future customization. Whether you’re searching for a full-time residence or a low-maintenance second home, this property presents a fantastic opportunity to enjoy the lake lifestyle with convenience and comfort.

14 Laurel Brook Dr Unit 14, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Railey Realty, Inc..

20160 Garrett Hwy Unit H708, Oakland
$260,000
1 Beds ⋅ 1 Baths
Welcome to Will O' the Wisp Condominiums, where premium upgrades meet penthouse-level lakefront living at Deep Creek Lake! This fully furnished, beautifully updated, rarely available, top-floor two-level condo features one bedroom and one bath, offering 550 square feet of comfort, charm, and versatility — perfect as a vacation home, year-round retreat, or income-producing rental. Start your mornings with exceptional sunrises from your private lakefront balcony — one of the best views in the building! Inside, you’ll find brand-new luxury vinyl plank flooring, updated lighting, and a show-stopping custom staircase, which replaced the outdated spiral design and was so substantial it had to be hoisted into the condo via the roof — a true architectural centerpiece. This penthouse-style unit requires no steps as there's an elevator from the main level to the condo, offering rare convenience and accessibility and offers LVP wood floors, new lighting and soaring ceilings. Currently operating as a successful short-term rental with Railey Vacations under the name "Anchors Away," this property has a proven rental history — offering an immediate opportunity for investment income with an Average Daily Rental of $199.65 and Annual Gross Income Potential of $27k to $35k. Recent mechanical upgrades include a new HVAC system (2025), hot water heater (2024)— all the major updates are already done. The unit also includes covered garage parking, making life easier year-round. Enjoy resort-style amenities including an indoor pool, hot tubs, fitness center, sauna, game room, private sandy beach, dock slip access through the HOA, and a fully serviced front desk for guest support and added security. All of this is just minutes from Wisp Resort, State Parks, and adjoining two fine dining restaurants — the perfect base for four-season fun at the lake.

20160 Garrett Hwy Unit H708, Oakland

Listing courtesy of The KW Collective. Contact:

Selling Office: Railey Realty, Inc..

277 Cheeks Ln, Oakland
$255,000
3 Beds ⋅ 2 Baths
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, fishing, kayaking, and year-round adventure. Inside, you’ll find warm rustic charm with comfortable living spaces, a gas fireplace stove for cozy mountain evenings, and a bunk room perfect for hosting family and friends. One of the three bedrooms features its own private half bath and private deck, creating a relaxing escape after a day outdoors. Enjoy quiet mornings and unforgettable evenings from the covered front porch, surrounded by nature and mountain serenity. Conveniently located only 10–15 minutes from Deep Creek Lake and Wisp Resort, this property offers easy access to boating, skiing, dining, and entertainment while still feeling wonderfully secluded. Priced to be an affordable vacation home in today’s market, this is an incredible opportunity to own the ultimate log cabin getaway in one of Western Maryland’s most sought-after outdoor destinations.

277 Cheeks Ln, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Railey Realty, Inc..

127 Jeffrey Ln Unit 18C, Oakland
$255,000
3 Beds ⋅ 2 Baths
Welcome to 127 Jeffrey Lane 18C! Centrally located at Deep Creek Lake, this unit offers convenience year round to restaurants, skiing, golf courses, Deep Creek Lake and even one of the areas most desired coffee shops just a few hundred feet away. Enjoy northeastern exposure for great sunrises overlooking the lake. The main level offers a kitchen, living room with wood burning fireplace, 2 bedrooms, 1 full bath and laundry room. The lower level offers 1 full bedroom and 1 full bathroom. Enjoy a relaxing evening in the hot tub on the lower level patio area! Condo ownership allows for ease of ownership. Established vacation rental. Sold fully furnished and turnkey! Looking for an enjoyable place here at the lake? Call today to schedule a private tour!

127 Jeffrey Ln Unit 18C, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Unrepresented.

18 Ollie North Rd, Oakland
$250,000
4 Beds ⋅ 2 Baths
Welcome to 18 Ollie North in Oakland, MD—an exceptionally well-maintained home offering comfort, functionality, and space both inside and out. This inviting 4-bedroom, 2-full bath residence spans two levels and showcases meticulous care throughout. Inside, you’ll find a bright and welcoming layout with a well-appointed kitchen featuring stainless steel appliances, perfect for everyday living or entertaining. The home offers flexible living space with multiple bedrooms and comfortable gathering areas designed to accommodate family and guests with ease. Step outside to enjoy the expansive yard—ideal for outdoor activities, gardening, or simply relaxing in the fresh mountain air. A charming gazebo provides the perfect spot for morning coffee or evening gatherings. The property also includes a detached outbuilding that can serve as additional storage, a workshop, or hobby space. A spacious driveway allows for ample parking, and the home features ramp access for added convenience and accessibility. Combining thoughtful features, a generous lot, and pride of ownership throughout, this Oakland property is a wonderful place to call home!

18 Ollie North Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Railey Realty, Inc..

511 E Green St, Oakland
$250,000
4 Beds ⋅ 2 Baths
Completely renovated and move in ready, this charming Oakland home combines modern comfort with classic character. Every detail has been thoughtfully updated, including new wiring, insulation, roof, windows, flooring, and a beautiful kitchen, giving you peace of mind and a fresh, contemporary feel throughout. The main level features an open layout with a spacious living room that flows into the kitchen, perfect for entertaining or everyday living. You’ll also find a main level bedroom, full bath, and laundry for added convenience. Upstairs are three more bedrooms and another full bath, providing plenty of space for family or guests. Outside, the quarter acre lot offers room to relax or garden, plus a detached garage for parking or storage. Located in the heart of Oakland, you’re close to shops, restaurants, and everything this friendly mountain town has to offer. All the work has been done, all that’s left is to move in and make it yours. Schedule your private showing today.

511 E Green St, Oakland

Listing courtesy of Taylor Made Deep Creek Vacations & Sales. Contact:

Selling Office: Taylor Made Deep Creek Vacations & Sales.

711 Heritage Dr, Oakland
$249,000
3 Beds ⋅ 2 Baths
Welcome to easy living at this beautifully maintained 3-bedroom ranch-style home w/ attached heated garage. Updated Modern, spacious Kitchen area, Master BR Suite w/ private bath & walk in closet. Efficient gas forced-air heating w/ central air conditioning, ensuring year-round comfort in every season. Backing to trees, the home provides a peaceful, private setting while still being centrally located just minutes from shopping & schools. Outdoor recreation is right around the corner at Broadford Lake only minutes away, featuring kayaking and canoeing, a beach and swim area, scenic walking trails, and a pavilion - perfect for enjoying Garrett County's natural beauty. Call today for your private showing.

711 Heritage Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Railey Realty, Inc..

565 Glendale Rd Unit 103B, Oakland
$245,000
1 Beds ⋅ 1 Baths
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 community amenities, including a sauna, fitness center, game room, and more. This condo is sold turn-key and fully furnished, featuring efficient ductless heating and A/C units for year-round comfort. The monthly condo fee conveniently covers exterior maintenance, common grounds, and lakefront access. Don’t miss your chance to own a premium lakefront property—without the premium price tag!

565 Glendale Rd Unit 103B, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Railey Realty, Inc..

252 Racoon Dr, Oakland
$239,000
2 Beds ⋅ 2 Baths
Embrace the mini farmhouse feel in this immaculately kept 2 bedroom, 1.5 bathroom home in the Youghiogheny Mountain Resort. Situated on two level lots totaling 1.21 acres, this property offers a quiet setting with grounds that are setup for entertaining. As soon as you walk in, you'll be greeted with vaulted ceilings with an open main living area into the kitchen and dining. The bedrooms are strategically placed toward the back of the home to separate the living space from quiet space. A stackable laundry system is located in the hallway. Enjoy a morning cup of coffee on the front covered porch or a campfire on those cooler, fall evenings in the back yard. Home is being sold fully furnished and turn key. Whether you are looking for a vacation getaway or a full time residence, this home captivates the best of both worlds. Call today to schedule a private showing!

252 Racoon Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Taylor-Made Deep Creek Sales.

5202 Hutton Rd, Oakland
$239,000
3 Beds ⋅ 1 Baths
First time homebuyer alert!! Charming ranch-style home offering 3 bedrooms, 1 full bath (jetted tub!), and loads of potential! This one-level home sits on over 12 beautiful acres with mature fruit trees, providing plenty of space for outdoor activities, gardening, or even future expansion. The attached garage adds convenience, and the layout makes for easy, comfortable living. Located just minutes from the town of Oakland, MD, you’ll enjoy small-town charm with nearby shopping, dining, and local events. Plus, Deep Creek Lake is only a 15–20 minute drive away—ideal for weekend getaways, water sports, or winter skiing. With a little vision and effort, this property could shine again. Whether you're seeking a full-time residence, vacation home, or investment opportunity, this affordable acreage and location are hard to beat. Don’t miss your chance to own a slice of Garrett County countryside!

5202 Hutton Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Railey Realty, Inc..

1136 Black Oak Dr, Oakland
$218,000
3 Beds ⋅ 1 Baths
Tucked away on nearly an acre of wooded privacy in Yough Mountain Resort, this charming 3-bedroom, 1-bath A-frame cabin offers the perfect mountain retreat. Surrounded by towering trees, it features a welcoming front deck, an upper balcony with peaceful forest views, and a cozy fire pit area for evenings under the stars. Inside, you’ll find warm wood accents, soaring ceilings, and an open-concept living space filled with natural light. A detached two-car garage provides plenty of room for vehicles, ATVs, and outdoor gear. Enjoy the serenity of nature while still being just a short drive to Deep Creek Lake, Swallow Falls, and endless outdoor adventure. Perfect as a vacation getaway or full-time residence, the community boasts 50+ miles of ATV, snowmobile, and hiking trails, along with fishing, hunting areas, and many other amenities. Call today!

1136 Black Oak Dr, Oakland

Listing courtesy of Taylor Made Deep Creek Vacations & Sales. Contact:

Selling Office: The KW Collective.

41 Fox Den Rd, Oakland
$215,000
2 Beds ⋅ 1 Baths
Nestled in the heart of Deep Creek Lake, this charming and fully furnished cottage offers the perfect blend of relaxation and investment potential. Recently remodeled, it features a brand-new modern kitchen that seamlessly opens to the living area, refinished wood floors, and upgraded electric,. The light and airy upstairs space enhances the home's inviting atmosphere, complemented by large windows, an energy-efficient gas stove, and an open floor plan. Just steps from boat and jet ski rentals and the beloved Lakeside Creamery, this two-bedroom retreat is a sought-after rental property. Outside, enjoy a spacious patio with an outdoor fireplace, perfect for cozy evenings, while the storage shed provides ample space for all your lake toys. Whether you're soaking up the summer sun on the water or hitting the slopes at Wisp Resort in the winter, this home offers year-round recreation.

41 Fox Den Rd, Oakland

Listing courtesy of Taylor Made Deep Creek Real Estate. Contact:

Selling Office: Railey Realty, Inc..

4 Laurel Brook Dr Unit 4, Oakland
$212,000
2 Beds ⋅ 2 Baths
Welcome to your peaceful mountain escape in Laurel Brook, where convenience meets cozy comfort! This beautifully maintained 2 bed, 2 bath condo offers an easy, affordable way to enjoy life near Deep Creek Lake without the hassle of yard work or upkeep. Whether you’re dreaming of a low-maintenance full-time home, a weekend getaway, or an investment property, this one checks all the boxes. Step inside to find a warm, inviting layout designed for everyday comfort, with bright windows, natural finishes, and plenty of space to relax after a day exploring Garrett County’s great outdoors. Located just minutes from Deep Creek Lake and downtown Oakland, you’ll have quick access to boating, hiking, skiing, dining, and shopping. Everything you love about Mountain Maryland is right at your doorstep. With lawn care, snow removal, and exterior maintenance included in the HOA, you can spend your weekends enjoying the mountains instead of maintaining them. If you’ve been looking for a place that feels like home from the moment you walk in, this is it. Come see why Laurel Brook is one of the area’s best kept secrets. Schedule your tour today!

4 Laurel Brook Dr Unit 4, Oakland

Listing courtesy of Taylor Made Deep Creek Vacations & Sales. Contact:

Selling Office: Railey Realty, Inc..

22 Shady Hill Dr, Oakland
$210,000
2 Beds ⋅ 1 Baths
Tucked away in a peaceful, nature-filled setting, this charming 2-bedroom, 1-bath ranch offers comfortable one-level living with a truly unique atmosphere. Surrounded by colorful wildflowers and mature landscaping, the property provides a quiet retreat that's perfect for enjoying the outdoors. Inside, the home has seen several recent upgrades, making it move-in ready while maintaining its inviting character. A detached one-car garage provides additional storage, and the greenhouse is a standout feature for gardening enthusiasts, hobbyists, or anyone looking to grow their own plants and produce. Conveniently located just outside downtown Oakland, you'll enjoy easy access to local shops, restaurants, schools, parks, and all the year-round recreation Garrett County has to offer.

22 Shady Hill Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Railey Realty, Inc..

565 Glendale Rd Unit A312, Oakland
$205,000
1 Beds ⋅ 1 Baths
Waterfront condo at Silver Tree Suites on Deep Creek Lake! This furnished 1 bedroom, 1 full bath loft unit offers 785 square feet across two levels and is one of only four layouts in the building with a private bedroom. Featuring granite countertops, a granite hearth, gas fireplace, fresh paint, updated furniture, carpet, and luxury vinyl plank flooring. The kitchenette includes a dishwasher, microwave, and refrigerator. Wall unit heat and A/C, public water and sewer, and shared laundry keep ownership simple. Elevator building with exercise room, sauna, extra storage, common grounds, and lake privileges with fishing and canoe/kayak access. A clean, low-maintenance lakefront opportunity in a well-known waterfront community. Call today for details!

565 Glendale Rd Unit A312, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Railey Realty, Inc..

43 Sloan Tract Rd, Oakland
$202,039
4 Beds ⋅ 2 Baths
Step back to the early days of Deep Creek Lake with this 4-bedroom, 2-bath home full of character and potential. Renovations are underway but unfinished, making this a true handyman or contractor special. Connected to public sewer, the home offers a head start for completing the kitchen and bathrooms and adding custom finishes to create a one-of-a-kind retreat. Enjoy views of Deep Creek Lake and a prime location in the heart of the lake area, just minutes from Wisp Resort and all local attractions. A rare opportunity to restore and personalize a classic Deep Creek home. This location is great, whether looking to make this a private residence, vacation home, or lake area rental investment.

43 Sloan Tract Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Railey Realty, Inc..

1108 Hutton Rd, Oakland
$199,000
2 Beds ⋅ 1 Baths
Welcome to 1108 Hutton Rd—a charming and well-maintained home set on a level lot near the highly sought-after Crellin Elementary School. This 2-bedroom, 1-bath property offers easy one-level living with a bright, functional layout and plenty of room to grow. The clean, unfinished basement provides excellent storage or future expansion potential. Outside, enjoy a spacious yard ideal for gardening, pets, or outdoor entertaining, along with a detached two-car garage offering ample space for vehicles, tools, and hobbies. Perfect property for first time homebuyers!! Located in a peaceful rural setting while still convenient to Oakland and Deep Creek Lake amenities, this property is perfect as a primary residence, starter home, or investment opportunity. Clean, simple, and full of potential—this is a great opportunity in a desirable area.

1108 Hutton Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Taylor Made Deep Creek Vacations & Sales.

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