Oakland Real Estate

Oakland Real Estate

Welcome to Oakland, Maryland – a hidden gem nestled in the heart of the picturesque Appalachian Mountains. This charming subdivision offers a unique blend of natural beauty, rich history, and a tight-knit community atmosphere, making it an ideal place for families, retirees, and outdoor enthusiasts alike.

Oakland is renowned for its stunning landscapes, with lush forests, serene lakes, and rolling hills that provide a breathtaking backdrop for year-round outdoor activities. Whether you enjoy hiking, fishing, or simply taking in the fresh mountain air, the area offers an abundance of recreational opportunities. Nearby Deep Creek Lake, Maryland's largest lake, is a hotspot for boating, swimming, and winter sports, ensuring that adventure is always just around the corner.

The community itself is characterized by its warm, welcoming spirit. Residents take pride in their hometown, fostering a sense of belonging and camaraderie. Local events, farmers' markets, and seasonal festivals bring neighbors together, creating lasting friendships and cherished memories.

Oakland also boasts a rich historical tapestry, with beautifully preserved architecture and sites that tell the story of its past. The town's quaint downtown area features unique shops, delightful eateries, and cultural attractions, making it a perfect spot for leisurely strolls or a cozy afternoon coffee.

With its ideal blend of natural beauty, community charm, and rich history, Oakland, Maryland, is more than just a place to live; it's a lifestyle waiting to be embraced. Come discover the magic of Oakland and find your dream home in this idyllic subdivision today!

Newest Listings in Oakland

$365,000
5 Beds ⋅ 3 Baths
PRIME INVESTMENT OPPURTUNITY! Recently renovated (including plumbing and electric) in 2025, this triplex is a rare opportunity in the heart of downtown Oakland, MD. With three separate units, you'll have the potential for three streams of rental income from one property. Buyer could live in one unit and rent the other units out to help offset mortgage costs! Whether you're a seasoned investor or just getting started, this turnkey property offers updated finishes, strong income potential, and a prime location just steps from shops, restaurants, and everything downtown has to offer. Top floor is 1-bedroom and 1-bathroom. Middle floor is 2-bedroom and 1-bathroom. Bottom floor is 2-bedroom, 1-bathroom and has a laundry hookup. Contact me today with any questions or to schedule a time to tour the property!

615 E Oak St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$350,000
5 Beds ⋅ 3 Baths
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: 8665253466
$998,000
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.

17240 Garrett Hwy, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$259,900
3 Beds ⋅ 2 Baths
Very well maintained 3Br-2BA traditional style home in Oakland with huge 24X24 deck, paved driveway and one car detached garage. Home features almost 2000 square feet of living area, stainless steel appliances, and updated bathrooms. Great place to watch the Autumn Glory parade from you covered front porch. Hot water radiant heat with natural gas being the heat source. Newer replacement windows, roof replaced recently and as an added bonus this home features a whole house generator back-up. Convenient to all town activities, schools, and the hospital. 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.

102 N 3rd St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$250,000
Commercially zoned 0.57 acre level building lot in downtown Oakland, MD. Conveniently located off E Oak St and Town Park Lane with easy access to local shops, restaurants, and businesses along S Second St and E Alder St. Public utilities available on-site. Great opportunity for commercial development in a central location! Call today for more information!

116 E Oak St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$365,000
5 Beds ⋅ 2 Baths
Reduced and Ready to go!! Perfect one level retirement retreat or 2nd vacation home! Spacious and beautifully maintained all-brick rancher offering approximately 3,660 square feet of living space with room for everyone! This impressive home features 5 bedrooms, 2 full bathrooms, and a fully finished basement with its own private entrance—perfect for in-law potential, extended family living, or flexible multi-generational use. Inside, you’ll find a welcoming living room with custom built-in cabinetry, a separate formal dining room, hardwood floors, and two cozy fireplaces that add warmth and character throughout the home. The bright and inviting sunroom provides the perfect place to relax year-round with abundant natural light and additional living space for entertaining or quiet mornings at home. Outdoor living is just as impressive with a large, fully fenced rear yard, rear deck ideal for entertaining, plenty of parking, a one-car garage, and an oversized 28x12 shed offering exceptional storage or workshop space. Additional updates include replacement windows and an HVAC system approximately 6 years old for added peace of mind. Conveniently located within walking distance to town, hospital and medical offices, pharmacy, dining, and banking, this home combines space, comfort, and accessibility in one exceptional property.

321 N 3rd St, Oakland

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102669005
$224,900
1 Beds ⋅ 1 Baths
Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath house blends cozy living with endless potential. The upper level offers a cozy living area, a full kitchen, laundry room, bedroom, and full bath. But the real bonus? A spacious 2-car garage with its own entrance. It is perfect for a workshop, extra storage, or even a rental opportunity. With separate entrances for the garage and living space, this property offers built-in flexibility for income potential or multi-purpose use. Plus, the location is minutes to lake activities and downtown Oakland. Don't miss out on the chance to own this versatile gem. Schedule a showing today!

206 Mayhew Inn Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$69,999
Beautiful 1.04-acre wooded lot offering privacy and a peaceful natural setting. The property provides a wonderful opportunity to build your dream home surrounded by trees while still being conveniently located near local amenities, restaurants, shopping, and commuter routes.

5280 Cedar St, West River

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$89,900
If you've been looking for a place to build while enjoying some peace and quiet, this 15.75± acre wooded property is worth a look. Tucked away off Bethlehem Road just minutes from town and close to the Potomac State Forest, it offers the privacy of a country setting without being far from everyday conveniences. One of the biggest advantages is the 7.02-acre buildable lot (Lot 8 on the recorded plat), giving you a great spot to build a home or cabin surrounded by mature trees and wildlife. The remaining acreage provides plenty of room to explore, hunt, hike, or simply enjoy the outdoors. You'll also be close to the Potomac River for fishing, kayaking, and other outdoor activities, with thousands of acres of nearby state forest ready to explore. Finding a property that offers buildable land, privacy, and this much acreage at an affordable price is getting harder to do. Come walk the property and see if it's the right fit for your plans. Give us a call today for more information or to schedule a showing.

15.75 Acres Bethlehem Road, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$185,000
3 Beds ⋅ 2 Baths
Great, affordable starter home located in Oakland with public water and sewer, one car detached garage, hot water natural gas heat. Two bedroom and full bath on second level and possible third bedroom on main level with 1/2 bath. Cellar basement with mechanicals. Washer and Dryer hookups, washer/dryer convey, are located on the back enclosed porch which has electric baseboard heat. Enclosed front porch also for relaxing on those warm summer evenings. Very convenient location, close to stores, hospital, shopping, etc. 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.

729 E Oak St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$399,000

216 E Alder St, Oakland

Listing courtesy of Eagle Commercial Realty. Contact: (443) 226-7129
$1,650,000
4 Beds ⋅ 6 Baths
Unique luxury home on 23 acres with 360 degree views of Pleasant Valley. 5,100 + SQ. FT. 4 ensuite bedrooms, 2 additional powder rooms, formal living room/ballroom, informal living room, sunroom, den, pantry and large dine in kitchen. 4 fireplaces. full basement, 3 car attached garage. Whole home generator. Everything in this home is first rate. A must see for the discerning buyer

3898 3898 Underwood Rd, Oakland

Listing courtesy of Custer Realty & Auction. Contact: 3013344876
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