Oakland Homes for Sale

Oakland Homes for Sale

Welcome to Oakland, Maryland—a charming town nestled in the heart of Garrett County, where the beauty of nature meets the warmth of community. Known for its picturesque landscapes and vibrant local culture, Oakland serves as a gateway to adventure, making it a perfect place to call home.

Surrounded by the stunning peaks of the Appalachian Mountains and the serene waters of Deep Creek Lake, Oakland offers an abundance of outdoor activities year-round. Whether you enjoy hiking the scenic trails, boating on the lake, or skiing in the winter, there’s something for everyone to enjoy. The town itself boasts a rich history, with quaint shops, delightful eateries, and a friendly atmosphere that welcomes newcomers and long-time residents alike.

For those looking to find their dream home in this idyllic setting, Oakland has an array of homes for sale that cater to various lifestyles and budgets. From charming historic houses that reflect the town's heritage to modern family homes nestled in tranquil neighborhoods, there’s a perfect spot for everyone. Many properties offer breathtaking views, spacious yards, and easy access to local amenities and outdoor recreational areas.

Investing in a home in Oakland means not just finding a place to live, but embracing a lifestyle filled with adventure, community, and natural beauty. Explore our listings today and discover the perfect home that aligns with your dreams and aspirations in this enchanting Maryland town!

Newest Oakland Homes for Sale

$235,000
2 Beds ⋅ 2 Baths
Comfy, cozy, and full of mountain charm! This inviting 2-bedroom, 1.5-bath cabin is nestled on 1.26 private acres within Yough Mountain Resort, offering the perfect setting for a weekend getaway, recreational retreat, or peaceful escape. The open floor plan creates a comfortable gathering space, highlighted by a beautiful stone fireplace with a wood-burning insert that adds warmth and character, while stainless steel appliances and recent updates make the home easy to enjoy. Recent improvements include laminate flooring, added washer and dryer hookups, a water filtration system, a vapor barrier installed in the crawlspace, a new gravel circular driveway, and a new shed for additional storage. Outside, enjoy the covered front porch, rear deck, and balcony off the bedroom, all surrounded by the privacy and beauty of the mountains. Yough Mountain Resort offers 50+ miles of ATV, snowmobile, and hiking trails, as well as fishing, hunting areas, and numerous community amenities. If you're looking for a cabin with privacy, updates, and plenty of outdoor recreation right at your doorstep, this one is ready to enjoy! Call today!

1959 Birchwood Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$499,000
5 Beds ⋅ 4 Baths
Immaculate from top to bottom, this exceptional five-bedroom home offers three levels of beautifully maintained living space, making it an ideal choice for a primary residence. Thoughtfully designed for comfortable everyday living, the home provides plenty of room to gather, relax, and spread out. A stunning fireplace creates a warm and inviting focal point, while the attached two-car garage adds convenience and storage. Above the garage, an unfinished room offers exciting potential for additional storage, an office, guest quarters, or additional living space. The downstairs family room offers expansive square footage for cozy gatherings. Numerous recent upgrades, including a new roof, high-efficiency mini-split units, and an upgraded energy-efficient boiler and hot water system, provide added peace of mind. The beautiful screened-in back porch is perfect for enjoying morning coffee, relaxing in the evening, or entertaining guests. Tucked away in a wonderful, private Oakland neighborhood, this home offers peaceful residential living while remaining conveniently close to Deep Creek Lake, Wisp Resort, and area amenities. A truly special property that checks all the boxes!

607 Pin Oak Cir, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$639,000
3 Beds ⋅ 3 Baths
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 home features a well-appointed kitchen equipped with nice appliances, and an eat-in bar. Retreat to the spacious primary suite, complemented by two additional bedrooms, providing ample space for relaxation. The fully finished basement, with a convenient walkout entrance just steps from the driveway, offers endless possibilities while offering plenty of space to host friends and family. Step outside to discover a beautifully landscaped 0.63-acre fenced yard that backs to lush trees, and includes a playhouse/shed. Enjoy the expansive wrap-around deck with a covered roomy front and rear porch, perfect for morning coffee or entertaining family and friends while watching the valley full of wildlife. The location is just minutes to Deep Creek Lake, Wisp Ski Resort, restaurants, entertainment and food markets.

1529 Paradise Point Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$645,000
2 Beds ⋅ 2 Baths
Rare opportunity to own a thoughtfully designed container home in the Deep Creek Lake area! This distinctive 2BR/2BA retreat combines modern comfort with a private wooded setting. The open-concept interior features abundant natural light, a full kitchen, comfortable living space, and large sliders connecting the indoors to the outdoors. Enjoy a private backyard with hot tub, fire pit, and grill, plus additional storage for outdoor gear. Conveniently located near Deep Creek Lake, Wisp Resort, hiking, biking, golf, boating, fishing, state park trails, and local dining. Built with quality, this home features Superior foundation walls, high end finishes and a mountaintop setting that is sure to impress. A truly one-of-a-kind property with excellent appeal as a personal getaway, investment property, or short-term rental.

100 San Francisco St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$229,000
3 Beds ⋅ 2 Baths
Location, location, location! Enjoy easy living in this one-level raised rancher featuring 3 bedrooms and 1.5 baths, with all bedrooms conveniently located on the main level. Beautiful hardwood floors add warmth, while the covered front porch and side covered deck offer inviting spaces to relax and enjoy the peaceful surroundings. The fenced-in backyard provides plenty of outdoor space for pets, play, or entertaining. The full basement is ready for your finishing touches and offers additional potential, while the attached one-car lower-level garage provides convenient parking or extra storage. Recent updates include a new roof and a full WaterGuard system installed along the interior basement foundation. Located in a peaceful neighborhood close to schools, the hospital, and shopping, this home offers comfort, convenience, and plenty of opportunity to make it your own. Call today to schedule your showing!

139 S Oakhall Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$74,990
3 Beds ⋅ 1 Baths
INVESTOR SPECIAL!! GREAT FOR FIX AND FLIP OR HOLD! Property is sold completely as-is with all contents. Buyer to pay all closing,100% TT&Rs. CASH or Hard money only.

102 Roanoke Ave, Oakland

Listing courtesy of Samson Properties. Contact: 7033788810
$449,000
3 Beds ⋅ 2 Baths
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 naturally opens into the kitchen and dining area, creating an easy gathering space that flows into the inviting living room. A bedroom and full bath complete the main level, while two additional bedrooms upstairs provide a private retreat for family or guests. The lower level expands the living space with a spacious family room, bar, half bath, foosball, and shuffleboard, giving everyone a place to relax and have fun after a day at the lake. Outside, enjoy the full length covered front porch, wooded surroundings, patio with hot tub and grill, and firepit made for evenings under the stars. An oversized two car garage with storage above and a detached garage provide plenty of space for vehicles, lake gear, and storage. Whether you are looking for a year round home, a private mountain escape, or an investment opportunity, this property offers the flexibility to make it your own. Currently operating as a vacation rental, it provides the added opportunity for rental income while you enjoy all that Deep Creek Lake has to offer. Call today!

482 Pergin Farm Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$920,000
3 Beds ⋅ 2 Baths
Welcome to this charming 3Br, 2BA home in the quiet and serene Penn Point area of Deep Creek Lake. A Type A dock slip is included and is just an easy walk or golf-cart ride from the property, making lake days more convenient and enjoyable. Inside you'll find an inviting open concept kitchen, dining, and living area that flows seamlessly onto a spacious outdoor deck. Enjoy morning coffee, outdoor dining, grilling and entertaining while taking in the peaceful surroundings. The home sits on just under 1/2 acre, offering plenty of space to enjoy and potential for future expanding. The large, detached garage provides exceptional storage for your boat, jet skis, lake toys, and all your recreational gear. Whether you're looking for a year-round home or a Deep Creek getaway, this property offers the perfect combination of comfort, outdoor enjoyment, and access to the lake. Deep Creek Lake is a four-season destination with boating, golfing, hiking, skiing, dining, and activities for all ages. Conveniently located on Upper Penn Point Road, you'll be close to everything Deep Creek has to offer while still enjoying the peaceful setting. Come see all this property has to offer!

184 Upper Penn Point Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$399,900
3 Beds ⋅ 2 Baths
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 countertops, a double sink, stainless steel appliances, a large center island with ample seating, and a generous sized walk-in pantry offering exceptional storage. The main level includes 3 bedrooms and 2 full bathrooms, highlighted by a private primary suite with a walk-in closet and en-suite bathroom with a tiled walk-in shower, along with two additional bedrooms, a full hall bathroom, and a convenient laundry room. Step outside onto the exterior deck overlooking the yard, perfect for relaxing or entertaining, while the attached one-car garage provides added convenience. The full unfinished basement offers endless possibilities for future living space, a recreation room, home gym, office, or whatever best suits your needs. Located just minutes from newly built Broadford Elementary School, Broadford Park, Downtown Oakland, and Garrett Regional Hospital, and a short drive to Deep Creek Lake, this home offers the perfect blend of modern comfort, convenience, and accessibility. This stunning new build is a must see!

1407 Broadford Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$899,900
5 Beds ⋅ 6 Baths
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 kitchen, dining, and living area with stainless steel appliances, a large center island, fireplace, abundant natural light, and beautiful lake views. A main-level primary suite and additional full bath add convenience. Upstairs, a second luxurious primary suite offers a walk-in closet and spa-like bath with a jetted tub and separate shower. The lower level is designed for fun and relaxation, with three bedrooms and three full baths, a second living area, fireplace, wet bar, and access to the deck and hot tub. The entertainment continues with a plenty of space to gather. Outside, enjoy two decks, a hot tub, fire pit, grill, room for games and entertainment, expansive yard space, ample parking, and a storage building for your outdoor gear. Whether you’re soaking in the hot tub under the stars, gathering around the fire, or enjoying a quiet morning, Happy Hoursss...Hideaway delivers an unforgettable Deep Creek Lake experience in every season.

395 Woodlands Hill Ln, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$444,700
4 Beds ⋅ 4 Baths
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 that Deep Creek has to offer. Enjoy the outdoors from the spacious covered front and back porches—perfect for morning coffee, evening gatherings, and taking in the peaceful surroundings. With comfortable living spaces, ample bedrooms and baths, and a desirable location near area attractions, Hidden Treasures is ready to continue as a sought-after vacation rental or become your own private mountain-lake retreat. A wonderful opportunity to own a piece of the Deep Creek Lake lifestyle! Call today to set up a viewing of this lake area property!

333 Sloan Tract Rd, Oakland

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,199,000
4 Beds ⋅ 3 Baths
Beautiful lakefront home offering 89' of lakefront and a private dock. This home has been remodeled and is very warm and inviting from the moment you enter. Boasting a great island featuring granite countertops, and plenty of seating for family and friends. The lakefront views are unobstructed year round, and can be enjoyed from most any room. The outside space is just as pleasing with a wrap-around Trex deck, stone patio with a hot tub, and a firepit. If all of this isn't enough, take a few steps down to the lakefront and enjoy the type A dock. The central location is also hard to beat, just minutes to coffee, ice cream, Wisp Ski Resort, grocery stores and restaurants. Established rental "Moments & Memories". Call today to preview!

20698 Garrett Hwy, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
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