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

112 E Pennington St, Oakland
$325,000
5 Beds ⋅ 3 Baths
Price drop!! Close to the hospital and schools. Completely rebuilt and beautifully renovated 5 bedroom 3 bathroom home! Welcome to this stunning 5-bedroom, 3-bathroom home that has been completely transformed from top to bottom with exceptional craftsmanship and modern finishes. Offering the charm of a classic home with the peace of mind of virtually all-new construction, this property is truly move-in ready. Major updates include a new high-efficiency central HVAC system, all-new plumbing, new electrical wiring, and a new gas line. The home also features new exterior and interior wood framing, professionally waterproofed basement, and complete whole-house insulation, providing comfort and energy efficiency year-round. The exterior has been beautifully updated with new wood siding and hardie siding, new energy-efficient windows, new exterior doors, new trim, and a new rear porch, creating outstanding curb appeal and outdoor living space. Inside, you'll find a bright, open layout with new drywall, beautiful hardwood flooring, stylish lighting throughout, and a fully renovated interior. The gorgeous kitchen boasts brand-new appliances, modern cabinetry, and updated finishes, while all three bathrooms have been completely remodeled with contemporary fixtures and finishes. This is a rare opportunity to own a home where nearly every major component has been replaced, offering years of worry-free living. Combining timeless style, modern amenities, and quality construction, this exceptional home is ready for its next owner.

112 E Pennington St, Oakland

Listing courtesy of Lake Homes Realty, LLC. Contact:

17240 Garrett Hwy, Oakland
$859,000
6 Beds ⋅ 5 Baths
Luxury Living Meets Timeless Country Charm! Perfectly positioned on 10.33 picturesque acres between Oakland and Deep Creek Lake, this exceptional 6-bedroom, 4.5-bath home offers the ideal blend of refined comfort, modern updates, and peaceful privacy. Step inside to discover an inviting open floor plan highlighted by soaring wood ceilings, a dramatic floor-to-ceiling stone fireplace, and expansive windows that fill the home with natural light while showcasing the serene surroundings. The beautifully updated kitchen is designed for gathering, featuring granite countertops, abundant cabinetry, stainless steel appliances, and a spacious island that flows seamlessly into the dining and living areas. With six generously sized bedrooms and four-and-a-half baths, there's room for everyone to relax in comfort. Thoughtful upgrades throughout the home provide a fresh, modern feel while maintaining the warmth and character of this impressive property. Outside, your own private retreat awaits. Spend summer days enjoying the heated in-ground swimming pool, entertain on the expansive rear deck, or simply unwind while taking in the views of the park-like backyard. The sprawling acreage offers plenty of room for recreation, gardening, or simply enjoying the beauty of nature. Completing the property is a 3-car attached garage, offering ample space for vehicles, outdoor gear, and storage. Conveniently located just minutes from Deep Creek Lake, Wisp Resort, restaurants, shopping, and Oakland's historic downtown, this remarkable home delivers the perfect balance of luxury, convenience, and country living. Whether you're searching for a full-time residence or a private retreat near Maryland's premier four-season destination, this extraordinary property is one you won't want to miss. *$5,000 buyer credit for carpeting with accepted offer*

17240 Garrett Hwy, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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:

4a Mystic Creek Trl, Oakland
$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:

47 Holy Cross, Oakland
$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:

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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