Oakland Homes for Sale

Oakland Homes for Sale

Welcome to Oakland, Maryland – a hidden gem nestled in the picturesque Garrett County! Known for its charming small-town atmosphere and breathtaking natural beauty, Oakland is a haven for those seeking a peaceful lifestyle surrounded by stunning landscapes. With its close proximity to Deep Creek Lake and the majestic mountains of Western Maryland, Oakland offers endless opportunities for outdoor adventures, from hiking and biking to fishing and boating.

As you explore the quaint streets of Oakland, you'll be captivated by its rich history and vibrant community spirit. The town boasts a delightful mix of local shops, cozy cafes, and inviting restaurants, making it a perfect destination for both residents and visitors alike. The annual events and festivals held here foster a sense of belonging and celebrate the unique culture of the area.

For those looking to call Oakland home, you'll find a variety of homes for sale that cater to diverse lifestyles and preferences. Whether you're in search of a charming historic home, a modern retreat, or a cozy cabin in the woods, Oakland has something for everyone. The real estate market in this lovely town offers competitive prices, making it an attractive option for first-time buyers, families, and retirees alike.

Imagine waking up to serene views and crisp mountain air, with the comfort of knowing that your dream home awaits in this idyllic community. Discover the beauty and tranquility of Oakland, Maryland, and let its enchanting charm inspire your next move!

Newest Oakland Homes for Sale

1019 Lake Shore Dr, Oakland
$1,699,000
4 Beds ⋅ 5 Baths
Welcome to Your Dream Retreat at Deep Creek Lake! Discover this stunning, recently remodeled home that perfectly blends modern luxury with the tranquility of nature. Nestled among picturesque blue spruce trees, this 4-bedroom, 4.5-bath residence offers an exceptional getaway for both relaxation and adventure. The open-concept living space is designed for comfort and style. Enjoy a cozy fireplace that sets the perfect ambiance for chilly evenings, making gatherings with family and friends even more special. Step outside to a large deck that provides ample space for outdoor dining and relaxation. Unwind in the hot tub while surrounded by the serene sounds of nature. Take advantage of your very own “Type A” private dock slip, perfect for boating, fishing, and enjoying the stunning lake views and sunsets just steps away from your doorstep. Minutes from Wisp Ski Resort, you’ll have year-round access to outdoor activities and adventures. A variety of restaurants and shops are also nearby, ensuring convenience and fun at your fingertips. Whether you’re looking for a serene family retreat or a smart investment opportunity, this home at Deep Creek Lake delivers everything you need to make unforgettable memories.

1019 Lake Shore Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

5979 Cranesville Rd, Oakland
$339,000
5 Beds ⋅ 4 Baths
Stunning 1900 farmhouse situated on 7.82 acres, offering incredible mountain views, a spacious yard, and a beautiful setting adjacent to Nature Conservancy land.. The home features vinyl siding, a shingle roof, and a wraparound deck perfect for enjoying the surrounding scenery. Inside, you'll find five bedrooms, a welcoming entryway and mudroom, main-level laundry, and a spacious layout with three bedrooms on the main level, including a larger primary bedroom and one bedroom with an attached bathroom. The main bathroom features a double-sink vanity, while the upper level offers two additional bedrooms, including one with an attached bathroom featuring both a shower and bathtub. An electric heat pump with central air conditioning provides year-round comfort. The property also includes an impressive 30x50 detached garage with electricity and overhead doors at both the front and rear, offering plenty of space for vehicles, equipment, hobbies, or a workshop. With its acreage, breathtaking mountain views, and generous outdoor space this property offers a unique opportunity to enjoy the charm and possibilities of country living. A separate trailer on the property offers potential for a guest house or additional living space, with work needed to bring it to its full potential. The property is conveniently located just minutes from Deep Creek Lake and the town of Oakland, offering easy access to local shopping, dining, recreation, and year-round outdoor activities. Call today!

5979 Cranesville Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

16 E Pennington St E, Oakland
$189,900
3 Beds ⋅ 3 Baths
Welcome to 16 E. Pennington Street! This charming two-story home in the heart of downtown Oakland offers plenty of space, character, and an opportunity to make it your own, all at an affordable price! Just a short drive to Deep Creek Lake and priced to sell! Spacious colonial offering over 1,550 square feet, this home features three spacious bedrooms, two full bathrooms, and a convenient main-level half bath. The inviting front porch is a great place to relax, while the covered rear porch and deck provide additional space to enjoy the outdoors. Inside, you'll find a comfortable living room, a separate dining room with plenty of room to gather, and a spacious kitchen featuring oak cabinetry, a gas stove, and room for a large table. A generous laundry area, convenient half bath, and additional storage complete the main level. Upstairs, the primary bedroom offers great natural light and a spacious closet. Two additional generously sized bedrooms and two full bathrooms provide flexibility for family, guests, or a home office. The home underwent a full renovation in 2003 and offers additional improvements such as updated trex front porch steps and an insulated crawl space. Natural gas heat, public utilities, and no HOA add to the appeal. Situated on a nearly quarter-acre lot with off-street parking, this property offers the charm of an older home with plenty of room to personalize. Conveniently located in Oakland with access to local shopping, dining, and everyday amenities, it's a wonderful opportunity for a primary residence or investment property. Don't miss your chance to make this Oakland home your own!

16 E Pennington St E, Oakland

Listing courtesy of The KW Collective. Contact:

335 Pergin Farm Rd, Oakland
$475,000
3 Beds ⋅ 3 Baths
Enjoy the convenience of one-level living at 335 Pergin Farm Road. This 3-bedroom, 3-bath lake area home features recent interior upgrades that blend its original character with a refreshed feel, including updated flooring, bathrooms, appliances, cabinetry, and countertops. The primary bedroom offers a walk-in closet and tiled shower. Adding to the functional layout is a finished basement that provides additional living and flex space to suit a variety of needs and a full bathroom with a walkout. An attached 2-car garage adds everyday convenience, and the flat, 2.00-acre lot features an expansive grassy yard with plenty of room to enjoy the outdoors. Superior walls ensure a top of the line foundation from the ground up. Conveniently located near Deep Creek Lake, Wisp Resort, and the shops, restaurants, and amenities of Oakland, this property offers a great combination of updated interior features, usable outdoor space, and prime location for full time living or second home enjoyment.

335 Pergin Farm Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

74 Parks Rd, Oakland
$59,900
3 Beds ⋅ 1 Baths
**Investor Special with Mountain & Water Views** Opportunity is knocking at 74 Parks Road in Oakland, Maryland, positioned just steps from the West Virginia line and surrounded by some of the most sought-after recreation in the region. Enjoy peaceful views of Snowy Creek right from the front yard and take advantage of being just minutes from Deep Creek Lake, Alpine Lake Resort, and Herrington Manor State Park — offering year-round activities including boating, fishing, hiking, skiing, and more. Whether you're looking to create a full-time residence, mountain getaway, or short-term vacation rental. If you've been searching for a project property in a high-demand recreational area with creek views and proximity to multiple lakes and state parks — this is your chance to build equity in one of Western Maryland’s most scenic settings. Bring your builder or contractor and your creativity — the possibilities are endless!

74 Parks Rd, Oakland

Listing courtesy of Real Broker, LLC. Contact:

1050 Christopher Way, Oakland
$269,900
2 Beds ⋅ 2 Baths
Discover your private mountain retreat at 1050 Christophers Way, situated on 13 acres spanning three separate parcels in the Backbone Ridge community. Showcasing breathtaking panoramic mountain views, this inviting home features warm wood accents, vaulted ceilings, a spacious loft, and a modern kitchen with stainless steel appliances. The walkout lower level offers additional living space, while the expansive deck provides the perfect setting to enjoy the spectacular scenery and peaceful surroundings. Additional features include an electric heat pump and water treatment system. Offering exceptional privacy, incredible views, and endless opportunities to enjoy the outdoors, this property is ideal as a full-time residence or personal getaway. Experience mountain living at its finest... Call today for details!

1050 Christopher Way, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

2296 Lake Shore Dr, Oakland
$909,000
4 Beds ⋅ 3 Baths
Very well maintained 4BR-2.5BA home on 1.001 acres with additional lakefront lot containing .0150 acres and 61.64' of lakefront with Type A dock. This home features several living areas and attached 2 car garage. Living room with wood burning fireplace. Lake views from the home and incredible waterfront on the lakefront lot. Architecturally appealing home with a mountain runoff stream running right under the home. Front lakeside deck and wonderful rear deck with plenty of room for a hot tub. Whole house GENERAC generator with two propane tanks that supply the propane that are owned by the seller. Central location close to Wisp, ASCI, and Lodestone Golf Course. RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. DURING INCLEMENT WEATHER CONDITIONS, PROSPECTIVE PURCHASERS AND THEIR AGENTS ASSUME ALL LIABILITY ASSOCIATED WITH OR BY WEATHER AT THE PROPERTY.

2296 Lake Shore Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

228 N 4th St, Oakland
$295,000
3 Beds ⋅ 2 Baths
Exquisite 3/4BR, 2BA Craftsman-style residence has been incredibly well maintained and lovingly cared for. Impressive kitchen remodel, hardwood floors, gas fireplace and multiple heat/cooling options. Home shows well - very clean and well-kept and a sensible floorplan. Full basement with overflow sleeping area and storage options. The kitchen is equipped with updated countertops & appliances. Cozy front porch and large rear deck with a spacious yard area (double lot) plus a storage shed. Fantastic location, close proximity to downtown Oakland, directly across the street from the hospital and close to pharmacies, dining options and shopping. Oakland offers a vibrant community atmosphere, with access to local parks, schools, and recreational areas. Conveys with most furnishings.

228 N 4th St, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

5423 Gorman Rd, Oakland
$225,000
1 Baths
Currently configured and listed as a small commercial store, this versatile property offers exciting potential for conversion to a residential use, subject to applicable approvals and the addition of a required sprinkler system. Enjoy beautiful mountain views and a convenient location just minutes from downtown Oakland, offering easy access to shopping, dining, entertainment, and local amenities. A unique opportunity for an owner-user, investor, or buyer looking to create a residence in a desirable and convenient location. Bring your vision and explore the possibilities!

5423 Gorman Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

503 E Alder St, Oakland
$155,000
4 Beds ⋅ 2 Baths
This is a Homepath property. Large historic home with lots of unique features in the construction design. Quarter acre, corner lot with lots of outdoor space and a one car detached garage. Home has four upper level bedrooms, a main level and upper level bath.

503 E Alder St, Oakland

Listing courtesy of Homes & Land Real Estate. Contact:

1038 S Blakeslee Rd, Oakland
$2,100,000
5 Beds ⋅ 6 Baths
Get ready to relax & enjoy Deep Creek Lake at your 5 BR 5 Bath home offering a wooded level setting with the lake and dock slip right out in front of you. Located in the area's premiere community, Blakeslee, you'll appreciate the inviting open floor plan featuring two living areas, 5 suites with direct bath access, direct access to a large deck, covered porch or relax in the comfy screened porch. The outdoor area also offers a fire pit and room for outdoor games. Beautifully and tastefully decorated, the atmosphere within and without is perfect regardless of season. The home has had over 30 meaningful updates including bathroom remodels and major mechanical improvements allowing you the opportunity to spend more time relaxing and less time making updates and repairs. The Blakeslee offers the best amenity package on the lake including an indoor pool and community center along with multiple tennis, pickleball courts, a multi use play field, tot lot and more, community trash center, storage area and over 100 common area acres with trails to enjoy. The 5 mile private road system is safe and perfect for walking and biking. The property also currently provides revenue potential and is known as Unsalted Memories.

1038 S Blakeslee Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

2092 Gorman Rd, Oakland
$349,000
4 Beds ⋅ 2 Baths
Welcome to this spacious raised ranch offering incredible views, abundant living space, and room to grow! The main level features three bedrooms, including a private primary suite with an attached bath complete with a soaking tub, separate shower, private toilet area, and walk-in closet. The inviting kitchen boasts hardwood floors and a pantry, with two separate living areas just off the kitchen, plus a separate dining room for easy entertaining. A convenient main-level laundry and mudroom add functionality, while the paneling throughout adds a warm, classic feel. Step outside onto the covered front deck that wraps around the side of the home and offers incredible views, making it the perfect spot to enjoy your morning coffee or unwind while taking in the scenery. The lower level adds even more living space with a fourth bedroom, game room, additional finished space, and an additional bathroom that is already in place and ready for the final touches, plus additional unfinished space to make your own. An oversized two-car garage provides plenty of room for vehicles, storage, and hobbies. With beautiful surroundings, multiple living areas, a spacious lower level, and breathtaking views from the covered deck, this is a home you won’t want to miss!

2092 Gorman Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

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