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

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:

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

3 Beds ⋅ 2 Baths

Vintage 3BR Lakefront Dome Home with Private Type "A" Dock! & no HOA . Own a piece of Deep Creek charm with this unique 3-bedroom, 2-bath vintage lakefront home w/ 2,034 finished square ft of living area, featuring 100 feet of lake frontage, beautiful sandy shoreline, and a private dock. The eye-catching dome-style architecture sets this property apart, offering a cozy and distinctive retreat. Located just minutes from Wisp Ski & Golf Resort and the ASCI Whitewater Course, it’s perfectly positioned for year-round adventure. Currently an established rental, this home offers both personal enjoyment and income potential. Don’t miss your chance to own a truly special lakefront getaway! Schedule your showing today

2849 Shingle Camp Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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

2 Beds ⋅ 1 Baths

A rare opportunity to own a completely renovated farmhouse-style home in Oakland! Offering 6.25 premium acres of gradually sloped land with several apple trees, open field areas and incredible views facing southeast from the top of the property. Inside, you'll be greeted with an oversized mudroom/office space, renovated kitchen, hardwood floors, tile shower and comfort from the recently added HVAC system. The lower level is a full basement with laundry space, plenty of storage, lighting, pellet stove and an attached 1-car garage. Other recent improvements include new roof in 2021, new deck in 2021, new garage roof in 2023, new basement windows in 2023, new HVAC 2021. An additional 2-car garage is insulated with lighting and a wood stove. An oversize shed offers plenty of storage for the toys. At the top of the property, you'll be greeted with incredible views accompanied by a 5 bedroom perc site for a future homesite. Homes in this condition with acreage are difficult to find and do not last long on the market. If you would like to schedule a private tour, please reach out while the opportunity is still available!

1158 Kings Run Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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

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:

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

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:

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:

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

4 Beds ⋅ 3 Baths

Experience the best of Deep Creek Lake living at this beautifully renovated mountain retreat in the peaceful and desirable Paradise Ridge lake access community. Thoughtfully updated from top to bottom, this home blends modern comfort with the serenity of nature, creating the perfect full-time residence, vacation getaway, or potential vacation rental investment property. One of the property's standout features is its close proximity to one of the most desirable lake access areas on Deep Creek Lake. Enjoy convenient access to the water, offering a more private and relaxing lake experience without the crowds. Featuring a level shoreline, picnic pavilion, ample parking, and easy entry for paddle boards, kayaks, canoes, swimming, and fishing in the quiet no wake zone cove. Nestled in a quiet, wooded setting, you'll appreciate the peaceful surroundings while remaining just minutes from local restaurants, shopping, Wisp Resort, state parks, golf, and all the year-round recreation Deep Creek Lake has to offer. Whether you're spending the day on the lake, enjoying nearby dining, or relaxing in the tranquil setting, 180 Paradise Ridge Road offers the perfect combination of spacious living space, convenience, comfort, and mountain charm. Chill out on the large back deck and patio area or around the campfire. Don't miss this opportunity to own your own slice of Deep Creek paradise. Get your tour scheduled now!

180 Paradise Ridge Rd, Oakland

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

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