Oakland Real Estate

Oakland Real Estate

Welcome to Oakland, Maryland—a hidden gem nestled in the heart of the picturesque Appalachian Mountains. Known for its breathtaking natural beauty and a tight-knit community atmosphere, Oakland offers a serene escape from the hustle and bustle of city life. With its charming small-town vibe, this subdivision is perfect for families, retirees, and anyone seeking a tranquil lifestyle.

One of the standout features of Oakland is its stunning surroundings. The area is surrounded by lush forests, pristine lakes, and rolling hills, making it an outdoor enthusiast's paradise. Residents can enjoy a variety of recreational activities, including hiking, fishing, and boating at nearby Deep Creek Lake, which is just a short drive away. In winter, the nearby Wisp Resort offers skiing and snowboarding, ensuring year-round enjoyment for all.

The community of Oakland is rich in history, with well-preserved architecture and a welcoming atmosphere. The downtown area features quaint shops, delightful cafes, and local eateries where you can savor Maryland's culinary delights. The annual events, such as the Oakland Heritage Festival, foster a sense of community and provide opportunities for residents to connect and celebrate their shared love for this beautiful area.

Families will appreciate the excellent schools and safe neighborhoods that Oakland offers, making it an ideal place to raise children. With its unique blend of nature, community spirit, and small-town charm, Oakland, MD is not just a place to live; it’s a place to call home. Come explore the beauty and warmth of Oakland—where your dream lifestyle awaits!

Newest Listings in Oakland

5423 Gorman Rd, Oakland
$225,000
1 Baths
Currently configured and listed as a small commercial store, this versatile property offers exciting potential for conversion to a residential use, subject to applicable approvals and the addition of a required sprinkler system. Enjoy beautiful mountain views and a convenient location just minutes from downtown Oakland, offering easy access to shopping, dining, entertainment, and local amenities. A unique opportunity for an owner-user, investor, or buyer looking to create a residence in a desirable and convenient location. Bring your vision and explore the possibilities!

5423 Gorman Rd, Oakland

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

216 N 12th St, Oakland
$265,000
3 Beds ⋅ 2 Baths
"RANCHER WITH IN GROUND POOL" REDUCED!! Well maintained Cedar Siding Rancher on large level lot with 3 bedrooms, 1 1/2 baths, beautiful hardwood floors on main level, Living room with wood burning brick fireplace, Large eat-in-kitchen/ dining area, with door that leads to deck overlooking in ground pool! Fenced yard and huge shed/pool storage, lower level finished great room for family entertaining with cozy wood stove which will be great for chilly days. New roof, hot water heater, cedar just stained/sealed! AND NEW DRIVEWAY 10/2026 COST WAS $8K - Come take a look!

216 N 12th St, Oakland

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

615 E Oak St, 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:

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:

102 N 3rd St, Oakland
$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:

116 E Oak St, Oakland
$230,000
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:

321 N 3rd St, Oakland
$350,000
5 Beds ⋅ 2 Baths
Aww shucks - the sellers have reduced the price!! 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:

206 Mayhew Inn Rd, Oakland
$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:

5280 Cedar St, West River
$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:

15.75 Acres Bethlehem Rd, Oakland
$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 Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

no property photo
$204,000

216 E Alder St, Oakland

Listing courtesy of Eagle Commercial Realty. Contact:

315 Coolidge Ave, Oakland
$264,500
3 Beds ⋅ 2 Baths
Well maintained brick rancher located in the heart of Oakland. This home offers a large kitchen open to the living room with a built-in fireplace, separate dining room, and new carpet through out. The basement is very clean, offering a clean slate for whatever you would like to do. The rear covered porch, deck and fenced in yard makes a great space to enjoy family and friends. The location is just minutes to grocery stores, schools, shopping and restaurants. This home won't last long, call today to preview!

315 Coolidge Ave, Oakland

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

Start Your Search

How much is your home worth?

Get instant property value now!