Oakland, MD Real Estate Search

Oakland, MD Homes for Sale

The Real Estate Market in Oakland, MD

Oakland, MD is a quaint town located in Garrett County, known for its picturesque surroundings and outdoor recreational opportunities. The real estate market in Oakland is diverse, offering a range of options for homebuyers looking to settle down in this charming town. From historic Victorian homes to modern new construction, there is something for everyone in Oakland.

Home Prices and Trends

The median home price in Oakland, MD is currently around $200,000, making it an affordable option for homebuyers on a budget. The real estate market in Oakland has been steadily growing in recent years, with an increase in property values and new developments popping up throughout the town. As more people discover the beauty and charm of Oakland, demand for housing continues to rise.

Popular Neighborhoods in Oakland

One of the most popular neighborhoods in Oakland is the historic downtown area, with its tree-lined streets and Victorian homes. This area is perfect for those who appreciate a small-town atmosphere and enjoy being within walking distance to shops and restaurants. Another sought-after neighborhood is the Deep Creek Lake area, offering waterfront properties and stunning views of the lake.

Investment Opportunities in Oakland

Real estate investment opportunities abound in Oakland, from fixer-upper properties in need of renovation to commercial developments in up-and-coming areas. With the town's growing popularity as a vacation destination and outdoor recreational hub, there is plenty of potential for long-term returns on investment in the Oakland real estate market.

Conclusion

Overall, Oakland, MD offers a diverse and thriving real estate market for homebuyers and investors alike. Whether you're looking for a charming historic home or a modern waterfront property, Oakland has something for everyone. With its affordable home prices, beautiful surroundings, and endless recreational opportunities, Oakland is a great place to call home.

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Oakland, MD Homes for Sale

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Newest Oakland, MD Homes for Sale

$399,900
4 Beds 3 Baths
Tucked away on a quiet cul-de-sac in the desirable Royal Charlotte community, this stunning 4-bedroom, 3-bathroom home is the kind of property you'll fall in love with the moment you arrive. Surrounded by the beauty and tranquility of the mountains and accessed by county-maintained roads, this impeccably maintained home showcases pride of ownership throughout. From the expansive Trex decking that wraps around much of the home and the welcoming covered front porch to the thoughtfully updated interior, every detail has been designed for comfort and enjoyment. The home features luxury vinyl plank flooring, carpet tile flooring, beautifully tiled bathrooms, granite countertops in the kitchen and all three bathrooms, heated tile floors in the master bathroom and lower-level bathroom, and spacious living areas perfect for gathering with family and friends. Major upgrades include new siding, new gutters with covers, a tankless hot water heater, backup water supply, whole-house generator, heat pump with gas backup, 2x6 exterior framed walls with drywall, new sliding glass doors, drywall, and a freshly painted foundation. Outside, you'll find a paved driveway, an impressive 30x40 garage, and a 16X50 pole barn with electric, providing ample space for vehicles, storage, hobbies, and outdoor equipment. Adding to the property's charm are mature plum, pear, apple, and peach trees, providing seasonal blooms, fresh fruit, and a touch of country living right in your own yard. Whether you're unwinding in the hot tub, entertaining on the deck, or simply enjoying the peaceful setting, this home offers the perfect blend of modern convenience, quality craftsmanship, and mountain charm. Properties this well cared for are rare, and one visit is all it takes to see why this exceptional home stands out from the rest. Call today!

511 Hilltop Rd, Oakland

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

$400,000
2 Beds 1 Baths
Discover the charm and comfort of this beautifully maintained manufactured home, nestled on a generous 2.07-acre lot. With a unique blend of rustic appeal and modern convenience, this property is perfect for those seeking a serene retreat without sacrificing accessibility. Step inside to find a warm and inviting interior with carpeting and laminate flooring that flows seamlessly throughout. The galley kitchen is equipped for all your needs and convenience. This home boasts two bedrooms, including an entry-level bedroom that offers easy access and comfort, well-appointed bathroom and a wraparound sunroom that adds even more living space and comfort to this home. Ceiling fans throughout the home provide a refreshing breeze, enhancing your comfort year-round. Step outside to your private oasis, where a charming deck invites you to relax and soak in the tranquility of your surroundings. The property also features a gazebo, perfect for outdoor gatherings or quiet moments of reflection. With a detached garage that accommodates up to four vehicles, additional storage including a workshop area, you'll have plenty of space for all your hobbies and equipment. Also included is a large pole building for extra storage or workshop. An additional oversized shed beside the pole building offer another “get away space” to enjoy more quiet time. And if that’s not enough, there is an additional lot included with the sale. This home is not just a place to live; it's a lifestyle choice that offers peace, privacy, and plenty of room to grow. Whether you're looking for a weekend getaway or a permanent residence, this property provides the perfect backdrop for your next chapter. Embrace the opportunity to create lasting memories in a space that truly feels like home. Don't miss out on this offering-schedule your private tour today and experience the potential that awaits!

2967 Pysell Crosscut Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$215,000
2 Beds 1 Baths
This charming manufactured home offers a delightful blend of comfort and functionality, perfect for those seeking a cozy retreat. With 1,440 square feet of thoughtfully designed living space, this residence features two bedrooms and full bathroom. Step inside to discover a warm and welcoming interior. The combination dining and living area is perfect for entertaining or enjoying quiet evenings at home. The galley kitchen is equipped with essential appliances making meal preparation and laundry a breeze. Natural light pours in through, enhancing the inviting ambiance throughout the home. An entry-level bedroom provides convenience and accessibility, while the additional bedroom offers a peaceful retreat for rest and rejuvenation. Outside, the property boasts a generous 0.72-acre lot, providing plenty of space for outdoor activities and gardening. Enjoy the fresh air on the charming porch or deck, perfect for sipping morning coffee or hosting gatherings with friends. The property also features a gazebo and shed, offering additional storage and a lovely spot to unwind. Parking is a breeze with a detached garage that accommodates up to four vehicles, along with a gravel driveway for extra convenience. The oversized garage includes an additional storage area, ensuring you have room for all your belongings. This home is not just a place to live; it's a lifestyle. The peaceful setting and thoughtful features make it an ideal choice for anyone looking to create lasting memories in a space that feels like home. Don't miss the opportunity to make this delightful property your own, where comfort meets convenience in a serene environment. Schedule a viewing today and envision the possibilities that await!

2967 Pysell Crosscut Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$1,200,000
4 Beds 5 Baths
Outdoor lovers retreat! Wooded trails and wildlife - HUNTING ALLOWED with no HOA restrictions. Welcome to mountain and lake living at its finest. Nestled on 6.89 very private acres, 122 Woodlands Hill Lane offers the perfect blend of seclusion, space, and comfort in one of Garrett County’s most desirable settings in the heart of Deep Creek Lake. This impressive 4-bedroom, 4.5-bath home features approximately 4,000 square feet of living space designed for gathering, relaxing, and enjoying the beauty of Western Maryland. Spacious living areas and multiple levels of comfort. The home sits on a 6.89-acre lot with surrounding parcels also for sale SEPARATELY totalling 21 ACRES for privacy, building or both! Inside, you'll find generous living spaces with warm finishes, hardwood flooring, and a fireplace that creates an inviting atmosphere year-round. The thoughtfully designed layout offers room for family and guests alike, while the expansive setting outside provides privacy and endless opportunities to enjoy nature. Features include a fireplace, wood stove, hardwood flooring, large basement, storage shed and substantial interior space. Other features include Anderson windows and doors, steam room/shower, infrastructure for central A/C and generator. Whether you're looking for a full-time residence, a mountain retreat, or a place to create unforgettable memories near Deep Creek Lake, this property delivers a rare combination of acreage, privacy, and convenience. Enjoy the peaceful surroundings while remaining just minutes from Deep Creek Lake recreation, dining, state parks, Wisp Resort, and all the outdoor adventures Garrett County has to offer. Your mountain escape awaits. Call today! The following surrounding parcels are also available for sale, please inquire. Parcel 657 - 3.15 ACRES Parcel 634 - 5.0 ACRES Adjoining parcel 658 also for sale: 6.89 ACRES - MLS #MDGA2011974 can also be purchased from separate owner

122 Woodlands Hill Ln, Oakland

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

$699,000
5 Beds 3 Baths
Private Mountain Retreat on 8+ Acres Near Oakland Discover the peace and beauty of Garrett County living on over 8 private wooded acres filled with mountain views, abundant wildlife, and endless opportunities to enjoy the outdoors. Deer, turkey, songbirds, and other native wildlife are frequent visitors, creating a true nature lover's paradise. Conveniently located just minutes from Oakland's shops, restaurants, schools, and everyday amenities, this property offers the perfect balance of privacy and accessibility. Outdoor enthusiasts will appreciate the home's proximity to Wolf Den Run State Park, Deep Creek Lake, Potomac State Forest, Jennings Randolph Lake, and thousands of acres of public land. Enjoy hiking, fishing, boating, hunting, swimming, and over 50 miles of ORV trails, with street-legal UTV access directly from the neighborhood. This custom-built 4-5 bedroom, 3-bath home offers over 3,900 square feet of thoughtfully designed living space. Designed with flexibility in mind, the main level features two dedicated office spaces ideal for remote work, homeschooling, hobbies, guest accommodations, or future bedroom needs. The spacious eat-in kitchen showcases granite countertops, custom cabinetry, high-end appliances, a trash compactor, and generous gathering space for family and friends. Throughout the home, you'll find whole-house luxury vinyl plank flooring, oak stairs, a cozy wood-burning fireplace, a finished garage, and a walk-out basement with rough-in plumbing for a future full bathroom and exceptional expansion potential. Owners have invested extensively in quality upgrades and peace of mind, including a Generac backup generator, tankless hot water system, whole-house water filtration system, owned 1,000-gallon propane tank, upgraded fire sprinkler system, exterior security cameras, attic storage, and an additional storage building. Step outside to enjoy a covered front porch, expansive rear deck with automatic SunSetter awning, mature trees, and beautiful mountain views. Located within a laid-back HOA that allows chickens, this property offers a rare combination of acreage, privacy, modern amenities, and epic outdoor adventure. Whether you're seeking a full-time residence, a mountain getaway, or a future retirement retreat, this exceptional property delivers the best of Garrett County living. You may never want to leave after seeing this gem!

170 Cherrywood Dr, Oakland

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

$191,409
3 Beds 2 Baths
Welcome to The Wise Quack - our cozy cabin in the center of Deep Creek Lake activities…all 4 seasons! If you’re looking for a weekend or holiday retreat, this is it! The Wise Quack is a successful short-term rental with rave reviews. The home has three bedrooms, two full bathrooms, a fully equipped kitchen, laundry room and lots of outdoor living space. There is parking for 6+ cars on the property. The home is private, set in beautiful, wooded surroundings on almost one acre. The fenced-in front yard is great for the little ones or to let your fur babies run free. The “fun factor” comes in a tiny-house game room which houses a ping pong table, darts, board games, etc. as well as outdoor games such as corn hole, spike ball, and horseshoes. The detached garage is perfect for storing your kayaks, canoes, paddle boards and bikes. A custom-built fire pit is in the back with lots of wood for your use and solar-powered lights for fire-side chats. The front deck overlooks trees above the Youghiogheny River. The back deck has a grill for your use. The kitchen is fully stocked with gas stove, dishwasher, refrigerator, microwave, and two peninsulas with seating for 8. If you want to buy more than a house, come see this wonderful property. It can be yours to enjoy year-round or rent out when you’re away. Updates include the following, all done in 2021: windows & sliding glass door, flooring, electric fireplace, lighting and ceiling fans, washer, dryer, dishwasher, ceramic tile, accent walls, tiny house game room. Additional updates include: new insulated crawl space (2023), and a new tin roof - tin lasts 50 years! (2024). Year-round activities include skiing, kayaking, stocked trout fishing, white water rafting, hiking, biking, golfing, horseback riding, boating and swimming. You are close to Wisp Resort, Deep Creek Lake and the Youghiogheny River (across the road). Surrounded by 8 state parks, the Wise Quack is turnkey, has all the comforts of home and is centrally located to shopping and restaurants. More than beautifully designed and professionally maintained, this property is also profitable. This is a manufactured home, not a trailer, built in 1999. Please contact the listing agent before scheduling through ShowingTime as the short-term rental operates year-round and may have guests. All offers considered.

8956 Oakland Sang Run Rd, Oakland

Listing courtesy of Taylor Properties. Contact:

$279,000
3 Beds 3 Baths
Nestled in the charming Mitchell Manor community, this delightful split-level home offers a perfect blend of comfort and style. With 2,242 square feet of thoughtfully designed living space, this residence features three spacious bedrooms and two and a half bathrooms, ideal for both relaxation and entertaining. There is also a walk-in closet/dressing room to die for! Step inside to discover an inviting open floor plan, highlighted by luxury vinyl plank flooring and an abundance of natural light. The country-style kitchen boasts upgraded countertops, an island for casual dining, and a cozy breakfast area, making it the heart of the home. Enjoy evenings by the brick fireplace in the family room, creating a warm ambiance for gatherings. The exterior is equally impressive, featuring extensive hardscape and an awning that enhances outdoor living. The expansive 0.46-acre lot offers a serene rear yard with beautiful views of the mountains and surrounding trees, perfect for enjoying nature or hosting summer barbecues. Located in a suburban setting, this home is conveniently close to local parks, schools, and essential public services, fostering a strong sense of community. Residents appreciate the peaceful atmosphere while being just a short drive from shopping and dining options. With an attached garage and ample driveway space, parking is a breeze. This property is not just a house; it's a place to create lasting memories. Experience the warmth and charm of Mitchell Manor, where comfort meets community. 7/29/26 - SELLER OFFERING A $2500 BUYER CLOSING COST CREDIT AND A HOME WARRANTY WITH ACCEPTABLE OFFER.

163 Mitchell Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$294,000
2 Beds 1 Baths
Nestled in the charming Traders Landing community, this delightful end-of-row townhouse offers a perfect blend of comfort and convenience with one of the best unobstructed views of the lake in Traders Landing. This villa-style home features two cozy bedrooms and a full bathroom, ideal for relaxation and unwinding after a long day. The inviting living space is enhanced by a warm wood-burning fireplace, perfect for creating a cozy atmosphere during cooler evenings. The updated kitchen is equipped with essential appliances, including an electric oven/range, microwave, and a new front-loading washer and dryer, making daily tasks a breeze. Ceiling fans throughout the home ensure a comfortable climate year-round. Step outside to enjoy the serene surroundings of Deep Creek Lake, where you can indulge in various water activities or simply take in the beautiful views. The community offers well-maintained common grounds, perfect for leisurely strolls or picnics with friends. Residents benefit from a comprehensive association that includes lawn maintenance, snow removal, and trash services, allowing you to spend more time enjoying your home and less on upkeep. The neighborhood is conveniently located near parks and public services, ensuring easy access to recreational opportunities and essential amenities. Experience the comfort and charm of Traders Landing, where every day feels like a retreat.

157 Jeffrey Ln Unit #21B, Oakland

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

$679,900
5 Beds 5 Baths
Discover refined mountain-lake living in this new construction townhome at Mystic Creek on Deep Creek Lake. Designed with today’s lifestyle in mind, the home features a modern open-concept main level ideal for entertaining, with clean lines, abundant natural light, and seamless flow between living, dining, and kitchen spaces. This spacious residence offers three primary suites, each with upscale attached bathrooms, providing comfort and privacy for owners and guests alike. Step outside to expansive rear decks that overlook a peaceful, wooded setting—perfect for relaxing after a day on the lake or slopes. The finished lower level includes Jack-and-Jill bedrooms, a full bath, and a second living area, creating an ideal space for guests, family, or recreation. Whether hosting large gatherings or enjoying quiet weekends, the layout offers flexibility and room for everyone. Mystic Creek is nestled along the banks of Deep Creek Lake, offering a serene setting while remaining close to area attractions. Enjoy being just 10 minutes from Wisp Ski Resort and Swallow Falls State Park, making this an exceptional four-season retreat. Ideal as a primary residence, vacation getaway, or investment property—this townhome delivers style, comfort, and location in one of Deep Creek Lake’s most desirable communities. *Home is still being finished, providing buyers the opportunity to choose bedroom flooring as well as kitchen countertops, appliances and cabinetry hardware.*

4A Mystic Creek Trl, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$575,000
3 Beds 2 Baths
With some minor modifications to the unit, it is possible for this condo to be rented as two separate condos (501 two BR and 701 one BR). Lakefront living at it's best can be found in this completely renovated spacious condo. This three-level unit is the perfect place to get away together! With space to come together and space to escape, this unit promises both privacy and togetherness for a memorable Deep Creek Lake experience! The first level has a full kitchen with wine fridge and attached living room with an electric fireplace, queen sleeper sofa, high top table with stools and a breathtaking balcony. Just up the stairs, enjoy the king bed in a loft bedroom that overlooks the living room and towering two-story window facing Deep Creek Lake! Also on this level is another bedroom with a Queen bed that shares a hallway bathroom with luxury finishes and a walk-in shower. On the top level you will enjoy even more space and accommodations. The 7th floor level has an additional hallway entrance for more privacy. Relax in the King bed and look out to your private balcony with gorgeous lake views. This space also features a well appointed luxury bathroom with walk-in shower and double bowl sinks. An additional mini-fridge and Keurig coffee maker provide easy access if you don't want to go downstairs. Up above in the vaulted loft curl up in the Queen size bed and take in panoramic sunrise views from every angle. Head down to the sandy beach to watch the water gently roll along the sandy shore of the resort’s private beachfront. No matter the season, there is plenty to keep you entertained with an on-site indoor pool, game room, fitness center, and more! 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.

20160 Garrett Hwy Unit #F501-701, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$6,499,900
7 Beds 9 Baths
Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with a sprawling island, Wolf range, and access to a four-season room that opens fully to the outdoors through custom bi-fold doors. The main-level primary suite spans nearly 900 sq ft with a private balcony, soaking tub, his-and-her vanities, and a massive walk-in closet. Enjoy five fireplaces, an indoor pool with fountains and a full bath, and three levels of outdoor living, including an outdoor kitchen, built-in hot tub with gazebo, outdoor shower, and deck drainage system to keep lower levels dry. Entertain with ease in the rec room with an industrial-style bar, climate-controlled wine cellar, and fully equipped gym. Three attached garages connect to a locker-style mudroom, with a lower-level garage ideal for a side-by-side or lake toys. Radiant heat, a whole-house generator, and three dock slips make this property as functional as it is flawless. A rare opportunity to own a true statement home in one of Deep Creek Lake’s most prestigious communities. Call today for your private tour!

47 Holy Cross, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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