Oakland, MD Real Estate Search

Oakland, MD Homes for Sale

Overview of Oakland, MD Real Estate

Oakland, Maryland, is a charming town located in Garrett County, nestled amidst the scenic beauty of the Appalachian Mountains. Known for its historical significance and outdoor recreational activities, Oakland offers a unique real estate market that caters to various buyers. The area presents a mix of single-family homes, vacation properties, and cozy cabins, appealing to anyone from first-time homebuyers to retirees seeking a peaceful retreat. As a gateway to Deep Creek Lake and several state parks, the real estate opportunities reflect a blend of nature-based living and community charm.

Market Trends and Property Types

The real estate market in Oakland has witnessed a steady evolution over recent years. As more people seek properties in quieter, picturesque landscapes, the demand for homes in Oakland has grown. Buyers can find everything from quaint Victorian-style houses to modern lakeside homes. Seasonal cabins and investment properties for those interested in rental opportunities near Deep Creek Lake are also prevalent. With its diverse property types, Oakland appeals to a wide range of potential residents and investors.

Community and Lifestyle

One of the most appealing aspects of owning real estate in Oakland is the sense of community and lifestyle that accompanies it. The town is characterized by friendly residents and numerous community events throughout the year. From local farmers' markets to seasonal festivals, there's always something happening. The proximity to outdoor activities, such as hiking, boating, and skiing, enhances the appeal for those looking to embrace an active lifestyle. This strong community emphasis plays a vital role in providing a desirable living environment for families and retirees alike.

Investment Potential

For investors, Oakland's real estate market offers attractive opportunities with promising returns. The area's appeal as a vacation destination means there is steady interest in short-term rental properties, particularly during the summer and winter months. As tourism continues to grow, investors are finding value in purchasing properties to rent out, catering to the influx of visitors to the Deep Creek area. Additionally, with the ongoing developments and infrastructure improvements in Garrett County, now could be an opportune time for investment in the region.

Future Outlook

The future outlook for the real estate market in Oakland, MD, appears optimistic. With ongoing development and an increase in remote working trends, more families and individuals are considering relocating to areas like Oakland for their serene settings and quality of life. The continued expansion of recreational facilities and community services will likely boost real estate values and attract new residents. As the charm of this town continues to spread, Oakland's real estate market is poised for steady growth, making it an exciting place to buy a home or invest.

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Oakland, MD Homes for Sale

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Newest Oakland, MD Homes for Sale

321 Deer Park Hotel Rd, Oakland
$384,500
3 Beds ⋅ 2 Baths
Double lots! Lot 4 & 5 of Hunting Ridge Estates will be sold together to bring up a total of .96 acre on your 2476 sqft. of finished living space home awaits you including your finished basement. Metal Roof is only 4 years old. Windows and doors are only 6 years old. Location, location...Welcome to 321 Deer Park Hotel Rd. where your mountain retreat will be just outside the city limits with only being only 10-15 minutes to nearly all the amenities the surrounding area has to offer. As you walk on to the nearly an acre of beautifully mature trees and landscaped double lot property where the only thing you'll hear is birds chirping and feel a sense of peace. Featuring a true mid-century modern. Fully updated 3 spacious bedrooms with extra long closets with 2 full bath, laundry/mud room and walkout 10 x 30 covered deck on the main floor. High end appliances and granite countertops along with a southern style porcelain sink compliments the kitchen. A major bonus is the washer and dryer are on the main floor. There are refinished hardwood floors and waterproof LV flooring throughout the entire house. With the fully finished walkout basement you will find many multi-use spaces. Custom bar, gym, reading room with a wood burning stove, double shop sink, extra full size refrigerator and other extras. As you walkout the basement, you will have a covered 7 person hot-tub with mounted 32 inch TV. There are 4 raised bed gardens, firepit, and a horseshoe pit to compliment the outside property along with 1 large shed w/electric and another large shed with covered deck with water and electric. and an additional garage/shop with a wood stove. There is also a 50-Amp/whole house manual transfer switch in the main garage to hook up your generator to should the power go out as well as a walkup attic for more storage. Parking for 9 plus vehicles on a double sealed driveway. Come find some peace and quiet and make this "stay-cation" style home yours. There are so many extra major renovations not listed that you just have to see to believe.

321 Deer Park Hotel Rd, Oakland

Listing courtesy of Houwzer, LLC. Contact:

415 Nazelrod Rd, Oakland
$3,249,000
4 Beds ⋅ 5 Baths
One of Garrett County's most unique and breathtaking mountain estates, this completely custom masterpiece was designed and built with exceptional craftsmanship and attention to detail. The 6000 +/- sq ft custom newly built home is located in the beautiful mountains of Garrett County, Maryland and offers the new owner one-of-a-kind unobstructed panoramic views, serenity, privacy and endless possibilities. Bordering the Potomac State Forest, up to 64 +/- acres ( 2 parcels, 1 of 50 acres and the other 13.74 acres)of pristine land, offering unmatched privacy, mature woodlands, spacious fields with a stocked pond and natural streams on the property, where the new owner can relax and recharge from everyday life. The property has also been perc tested for 1 additional residence. Outdoor amenities include three outbuildings. There are two finished outbuildings including a quaint accessory dwelling unit featuring a small kitchenette, living space, full bathroom and private deck. The second finished outbuilding is set up as a bunk house with a covered porch, barn doors and a custom stamped concrete patio with fire pit. You can use the unfinished outbuilding to store your ATV or UTV. The hot tub area offers stunning canyon views high above Laurel Run. This beautiful home has antique oversized brick, Everlast horizontal lap siding, architectural shingles, standing seam metal accents, black Anderson doors and Anderson windows, black half round gutters and downspouts, large exterior decks with custom railing and stamped concrete patios. This well constructed home features 2x10 exterior walls with spray foam insulation for low heating and cooling costs, radiant in floor heat along with forced air heat and central air conditioning. The interior walls are covered in native field stone from the property, shiplap siding, drywall, and barnboard. Added features include handcrafted wormy oak doors and wormy oak flooring and tile flooring. The interior of this 4 bedroom/5 bath features a luxurious main-level primary suite with walk-in shower, freestanding bathtub and walk-in closet, 1 spare bedroom/office on the main level, 1 main level full bathroom with walk-in shower, main level laundry room with utility sink, 2 upper level en-suites with walk-in shower and freestanding bathtubs, the lower level features a full bathroom with walk-in shower, there are 2 stone fireplaces, gourmet kitchen with extra-large island, walk-in pantry with custom cabinetry and prep sink, dining room, 3 family rooms and three finished utility rooms. The expansive lower-level family room opens to not one, but two attached finished garages with radiant floor heating for ultimate convenience. In the interior, you will also find large timbers, metal ceilings and exposed spiral ductwork. This mountain ranch estate is an outdoor enthusiast’s year-round dream property that offers unforgettable summer gatherings, spectacular fall vista views, a winter wonderland and breathtaking springtime hikes along cascading snowmelt waterfalls. In addition to opportunities for agriculture and farming, the property includes various trails suitable for nature walks, horseback riding, hiking, biking, ATV/UTV use, cross-country skiing, and snowmobiling. This large tract of land offers a natural habitat for wildlife that you can admire up close. The property also offers excellent birdwatching, hunting, fishing and nearby ORV trails. Located minutes from Deep Creek Lake, MD and Blackwater Falls, WV there are plenty of recreational activities, shopping, restaurants and medical facilities nearby. A rare blend of rustic elegance, seclusion, and natural beauty—this is truly a once-in-a-lifetime legacy property that you can call home. Potential for owner financing available.

415 Nazelrod Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

428 Sam Snead Cir, Oakland
$549,000
5 Beds ⋅ 4 Baths
Welcome to this beautifully appointed 5-bedroom, 3.5-bath home located in one of Oakland’s most desirable neighborhoods—Country Club Acres, bordering The Golf Club at Oakland. Offering the perfect blend of modern style, comfort, and convenience, this spacious home is designed to accommodate both everyday living and entertaining. Step inside to discover an inviting open-concept floor plan featuring upscale finishes throughout. The heart of the home is the stunning kitchen, complete with sleek cabinetry, solid surface countertops, stainless steel appliances, a large center island, and contemporary lighting that creates a bright and welcoming atmosphere. The adjoining dining and living spaces flow seamlessly together, making gatherings effortless. The home offers five generously sized bedrooms, including a spacious primary suite, along with 3.5 well-appointed bathrooms. The finished basement provides valuable additional living space perfect for a family room, recreation area, home gym, office, or guest accommodations. Outside, enjoy the charm of the covered front porch and the peaceful setting of this established community. The oversized attached one-car garage offers ample room for parking, storage, and outdoor equipment. Located just minutes from downtown Oakland, schools, shopping, dining, and Deep Creek Lake attractions, this exceptional property combines modern living with a highly desirable location.

428 Sam Snead Cir, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

1499 Foster Rd, Oakland
$375,000
4 Beds ⋅ 2 Baths
Welcome to Ricky's Retreat, a beautifully renovated mountain retreat nestled on 1.17 private wooded acres in the heart of Garrett County. Ideally located just minutes from Deep Creek Lake, Wisp Resort, Swallow Falls State Park, and downtown Oakland, this turnkey property offers the perfect balance of privacy, recreation, and modern comfort. Originally built as a raised ranch, the home has undergone extensive improvements in recent years, transforming it into a spacious and inviting 4-bedroom, 2-bath getaway. The main level features an open-concept design with warm wood accents, updated flooring, and a renovated kitchen complete with stainless steel appliances, modern countertops, and ample space for gathering. Three bedrooms and a beautifully updated full bath with a custom tiled walk-in shower complete the upper level. The fully finished lower level significantly expands the living space, offering a large recreation room, game area, additional sleeping accommodations, laundry area, and a second fully renovated bath. A traditional staircase replaced the original spiral staircase, creating improved functionality and flow between levels. Outdoor living is where this property truly shines. Multiple gathering areas have been thoughtfully created throughout the acreage, connected by gentle walking paths that lead to unique viewpoints and hangout spaces overlooking the surrounding mountain ridge. Enjoy evenings around the fire pit area, unwind in the hot tub, or relax on the expansive rebuilt deck surrounded by nature. Mature trees, abundant privacy, and a peaceful setting make it easy to enjoy every season. Whether you're searching for a primary residence, second home, or investment opportunity, this well-maintained and extensively updated property offers the ideal Deep Creek lifestyle with room to gather, entertain, and make lasting memories.

1499 Foster Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

20160 Garrett Hwy Unit C307, Oakland
$379,500
1 Beds ⋅ 1 Baths
Experience the best of Deep Creek Lake from this beautifully situated 2-story, 1-bedroom, 1-bath condominium at Will O' The Wisp. Offering 636 square feet of comfortable living space and spectacular lake views, this waterfront retreat is the perfect personal getaway, year-round residence, or vacation rental investment. Enjoy your morning coffee while taking in panoramic views of the water, then spend the day enjoying the incredible amenities that make Will O' The Wisp one of Deep Creek Lake's most sought-after destinations. Residents and guests have access to an indoor swimming pool and hot tub, racquetball court, fitness center, and arcade, providing year-round entertainment for all ages. 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. Boating enthusiasts will appreciate the community's 22 dock slips available for reservation and 4 dedicated jet ski docks, making it easy to get out and enjoy the lake. When it's time to relax, take advantage of two exceptional waterfront restaurant and bar venues located on-site, both featuring stunning lake views and convenient commercial docking. With professional on-site management, resort-style amenities, and a premier lakefront location just minutes from Wisp Resort, state parks, golf courses, and countless outdoor activities, this property offers an incredible opportunity to own a piece of Deep Creek Lake's waterfront lifestyle. Whether you're looking for a weekend escape or a property with strong rental appeal, this lakeview condo checks all the boxes.

20160 Garrett Hwy Unit C307, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

122 Woodlands Hill Ln, Oakland
$1,089,000
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:

163 Mitchell Dr, Oakland
$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. 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:

439 Paradise Hts, Oakland
$1,329,000
6 Beds ⋅ 5 Baths
Stunning 6-Bedroom Kathadin Log Home with Breathtaking 180° views of Deep Creek Lake with Lake Access and a Boat Slip! This exceptional vacation home offers the perfect blend of rustic charm and modern luxury. Boasting 180-degree panoramic views of the sparkling lake, this property is a true mountain retreat. Every room is designed to capture the beauty of the surrounding landscape, with expansive windows allowing natural light to flood the interior and provide endless vistas of the tranquil water. With over 4,000 sq ft of living space, this spacious home features soaring ceilings, rich wood finishes, and an open-concept floor plan that’s perfect for entertaining. The main level living room, with its impressive stone fireplace, is the heart of the home, leading seamlessly into the kitchen and dining area. Whether you’re hosting gatherings or relaxing by the fire, this space offers comfort and style in equal measure. The home includes six generously-sized bedrooms, each offering a serene escape and 5 of them with picturesque lake views. Step outside to the expansive deck that spans the length of the home, perfect for enjoying morning sunrises . A boat slip provides direct access to Deep Creek Lake, offering the ultimate convenience for boating, fishing, and water sports enthusiasts. Additional highlights include a fully finished lower level with a family room, second fireplace, and walk-out access to the outdoor living spaces. The property is complemented by a detached garage and additional parking areas off the drive that can accommodate up to 4 additional cars. Whether you’re looking for a year-round residence, a vacation home, or rental home, this stunning log home offers unparalleled views, a prime location, and a serene lake lifestyle. High rental potential and projection. Don’t miss the opportunity to make this magnificent property your own!

439 Paradise Hts, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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