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$1,200,000
4 Beds ⋅ 6 Baths ⋅ MDGA2010508 MLS
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
$229,900
2 Beds ⋅ 2 Baths ⋅ MDGA2012698 MLS
Nestled in the charming Oakland subdivision, this delightful traditional-style home, built in 2022, offers a perfect blend of modern comfort and timeless appeal. With 1,008 square feet of thoughtfully designed living space, this residence is ideal for those seeking a cozy yet functional environment. Step inside to discover a warm and inviting atmosphere, accentuated by luxury vinyl tile flooring that flows seamlessly throughout the home. The floor plan features two bedrooms and two bathrooms, providing convenience and accessibility for all. The heart of the home is the well-appointed open kitchen/dining/living area, equipped with essential appliances including a built-in microwave, electric oven/range, dishwasher, refrigerator, and access to the covered porch. Natural light pours in through the many windows, creating a bright and airy ambiance that enhances the home's inviting feel. The living areas are perfect for relaxation or entertaining, while the main floor laundry/mudroom adds an extra layer of convenience to your daily routine. Step outside to the covered porch where you can unwind with a morning coffee or host evening gatherings under the stars. Parking is a breeze with an attached garage and paved driveway, ensuring you have easy access to your vehicle year-round. The home's excellent condition means you can move in with peace of mind, knowing that everything is ready for you to make it your own. Don't miss the opportunity to make this inviting space your own!

808 N St, Mt Lake Park
$165,000
3 Beds ⋅ 2 Baths ⋅ MDGA2011048 MLS
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 Street, Oakland
$365,000
5 Beds ⋅ 3 Baths ⋅ MDGA2012446 MLS
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
$305,000
4 Beds ⋅ 3 Baths ⋅ MDGA2011702 MLS
Immaculate 4-bedroom/3-bath countryside home less than 10 minutes from Oakland. This property has been exceptionally well-maintained — truly move-in ready and prepared for you to make your own memories. A private in-ground pool awaits you out back - perfect for summer entertaining. Enjoy the western exposure and stunning sunsets from your elevated deck. A .86 acre lot provides a great yard and space to enjoy the outdoors. Recently added roof, A/C unit, furnace, hot water tank and pressure tank provide added value and efficiency to an already beautiful home. A truly quiet countryside setting with easy access to town. Don't miss this one! Call now for more details or to schedule your private showing!

29 Woodmont Lane, Oakland
$325,000
5 Beds ⋅ 3 Baths ⋅ MDGA2012308 MLS
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
$335,000
3 Beds ⋅ 3 Baths ⋅ MDGA2011680 MLS
Come see this beautifully maintained 3-bedroom, 3-bath Colonial-style residence nestled on a private 1-acre lot along Old Crellin Road in Oakland. Offering 2,300 square feet of living space, this home combines classic charm with modern comfort in an ideal location just outside town limits. Step inside to find a spacious and inviting layout, perfect for both everyday living and entertaining. The home is in excellent condition and has been thoughtfully cared for throughout. Enjoy outdoor living on the large wraparound deck, perfect for relaxing, hosting gatherings, or taking in the peaceful surroundings of this private setting. Additional features include: * Attached 2-car garage plus a detached 1-car garage for extra storage or workshop space * Whole-house generator that conveys for added peace of mind * Generous 1-acre lot offering space, privacy, and flexibility This property offers the perfect balance of tranquility and convenience—close to town amenities while still enjoying a quiet, country feel.

1740 Old Crellin Road, Oakland
$899,000
6 Beds ⋅ 5 Baths ⋅ MDGA2012252 MLS
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
$259,900
3 Beds ⋅ 2 Baths ⋅ MDGA2012246 MLS
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
$20,000
MDGA2011996 MLS
Lot within the town limits of Oakland with water and sewer hookups. This lot had a mobile home that was taken off. According to the owner, both Garrett County Planning and Zoning and the Town of Oakland have indicated that another mobile home can be placed on the lot but it has to be a NEW mobile home. According to P & Z, it must be a new mobile home and will have to be elevated 2' (three blocks) to be out of the 100 year floodplain. Buyer should verify with Garrett County Planning and Zoning and also the Town of Oakland. From a local surveyor: "You can see from the screenshot below that there is no building envelope outside of the floodplain. Any construction would need to be elevated above the 100’ floodplain + 2’ with special construction. For example, if you do an elevated house with a crawlspace, you can’t have mechanicals in the crawlspace and the crawlspace has to have flood vents installed to let water flow in and through the crawlspace. A floodplain elevation certificate would need to be done for any house for insurance and permitting. They would also need to do an MDE permit for impacts in the 100-yr floodplain, I believe." There is a two car detached garage on the lot. Property borders Town of Oakland Glades Park and Trail and directly across the street from the walking path at The Glades. Convenient location close to all town activities. 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.

460 W Liberty Street, Oakland
$150,000
MDGA2009886 MLS
A rare opportunity to acquire a high-potential 9.64 acre parcel located in the heart of Oakland. The location is very close to schools, grocery stores, restaurants, hospital and shopping. This site offers an ideal setting for residential, mixed-use, multifamily, or commercial development (subject to zoning approval). Easy access to infrastructure, with public utilities nearby at the street. This is an excellent opportunity for developers and investors seeking to build in a thriving town.

8th & Dennett Road Street, Oakland
$250,000
MDGA2011988 MLS
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
$185,000
3 Beds ⋅ 1 Baths ⋅ MDGA2012034 MLS
This charming 3-bedroom, 1-bathroom ranch-style home in the desirable Oakland Sang Run Rd area near the Youghiogheny River offers a blend of modern upgrades and classic appeal. Recently renovated in 2022, the interior features an open floor plan with luxury vinyl tile flooring, built-ins, and a gourmet kitchen equipped with stainless steel appliances and upgraded countertops. Enjoy the convenience of main floor laundry and double-pane windows for energy efficiency. Set on a generous 4.88-acre lot, the exterior includes an outbuilding and a wood/metal shed, perfect for storage or hobbies. The property provides ample driveway parking and a serene outdoor space for relaxation. Located in a vibrant community, residents benefit from nearby parks, excellent schools, and convenient public services. This home is ideal for those seeking a peaceful retreat with easy access to local amenities. Don't miss the opportunity to make this property your own!

2918 Oakland Sang Run Rd, Oakland
$365,000
5 Beds ⋅ 2 Baths ⋅ MDGA2011780 MLS
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
$375,000
3 Beds ⋅ 2 Baths ⋅ MDGA2011098 MLS
Experience the beauty of country living in this new construction log home nestled in a peaceful rural setting. Crafted with quality materials, this home offers the perfect blend of modern comfort. Enjoy open-concept living spaces, vaulted ceilings, and windows that allow you to enjoy the pastoral and mountain views. The large front covered porch offers a great space to enjoy family and friends while enjoying your scenic surroundings. Whether you're looking for a full-time residence or a private retreat, this is it.

2173 King Wildesen Road, Oakland
$224,900
1 Beds ⋅ 1 Baths ⋅ MDGA2011720 MLS
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
$249,000
3 Beds ⋅ 2 Baths ⋅ MDGA2011022 MLS
Welcome to easy living at this beautifully maintained 3-bedroom ranch-style home w/ attached heated garage. Updated Modern, spacious Kitchen area, Master BR Suite w/ private bath & walk in closet. Efficient gas forced-air heating w/ central air conditioning, ensuring year-round comfort in every season. Backing to trees, the home provides a peaceful, private setting while still being centrally located just minutes from shopping & schools. Outdoor recreation is right around the corner at Broadford Lake only minutes away, featuring kayaking and canoeing, a beach and swim area, scenic walking trails, and a pavilion - perfect for enjoying Garrett County's natural beauty. Call today for your private showing.

711 Heritage Drive, Oakland
$69,999
MDAA2138082 MLS
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
$20,000
MDGA2011044 MLS
A practical, in‑town lot close to everything that quaint downtown Oakland has to offer. You are just minutes to local shops, schools, and restaurants. Public utilities are available and easy access to main roads, making the possibilities endless.

Hammond Street, Oakland
$89,900
MDGA2011216 MLS
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
$225,000
3 Beds ⋅ 1 Baths ⋅ MDGA2010010 MLS
Located between Oakland and Deep Creek Lake, this log ranch is situated on 14.82 acres, including a stream, pond, barn and outbuildings with many possibilities to include potential subdivision configurations. The log home needs some TLC and updates; it is being sold as part of an estate. Some items of personal property remain in the house and on grounds. Those items are being removed. More photos will follow once the interior is emptied. The property will be sold AS-IS.

1570 Garrett Road, Oakland
$185,000
3 Beds ⋅ 3 Baths ⋅ MDGA2010742 MLS
Bring your vision and put your own personal touch on this great starter home! This property has great bones and endless potential. Featuring three bedrooms, two and a half bathrooms, and a large/open family room; it’s ready for your creative touch. Offering a nice level yard on a dead-end lane, which feels very private. The attached 1-car garage and rear shed provide the perfect extra storage space. Located close to schools, shopping, and DCL, this home could be a perfect flip, rental, or forever home.

141 Truesdale Road, Oakland
$20,000
MDGA2008330 MLS
If you are looking for an affordable building lot located in the beautiful town of Oakland, this is it! This .54-acre lot is just steps to downtown Oakland, and minutes to restaurants, shopping, and grocery stores. Offering public water and sewer, the possibilities are endless.

Hammond Street, Oakland
$342,000
3 Beds ⋅ 4 Baths ⋅ MDPG2164610 MLS
The seller may consider concessions made by the buyer with an offer. **NEWLY RENOVATED** 3-bedroom, 3.5-bath townhome in the heart of District Heights! Filled with natural light, this impressive home features a modern kitchen with a stylish peninsula, quartz countertops, a designer tile backsplash, and brand-new stainless steel appliances The bathrooms have been fully updated with striking tile work and upscale finishes, creating a spa-like retreat. Throughout the home, you’ll find brand-new hard surface flooring, fresh designer paint, modern fixtures, and elegant details that elevate the space. The fully finished basement includes a full bath and a versatile bonus room—perfect for a guest suite, home office, or media room. Ideally located just minutes from shopping, dining, parks, and major commuter routes, this home offers the perfect blend of style, comfort, and convenience. Don’t miss the chance to make this move-in ready gem your own—schedule your private tour today!

2241 Seton Way, District Heights
$180,000
3 Beds ⋅ 1 Baths ⋅ MDGA2010602 MLS
Inviting Country 3-Bedroom Traditional Farmhouse. This updated farmhouse offers a perfect mix of character and modern upgrades. Featuring 3 bedrooms, a bright sun porch, and a detached 2-car garage, the home is designed for both comfort and convenience. Enjoy outdoor living with a fenced-in yard, back deck, and peaceful valley views. The location is ideal—just minutes from town and shopping. Recent improvements include: LVT flooring & carpet, updated stove/range, metal roof and gutters, replacement windows. Full of farmhouse charm and move-in ready. Call now for your private tour!

627 Hamill Street, Oakland
$201,000
3 Beds ⋅ 2 Baths ⋅ CVR-2530353 MLS
Welcome to 2408 Oakland Ave — a classic 2-story home offering 3 bedrooms, 2 bathrooms, and outstanding potential. Step inside from the covered front porch into a welcoming foyer highlighted by soaring 9 ft ceilings and original hardwood floors. On the main level, the spacious living room features large windows that fill the space with natural light and a central fireplace that anchors the room. The kitchen provides a true blank canvas with white cabinetry, existing countertops, and a charming brick accent wall—ready for a full renovation. A generous dining room offers plenty of space for gatherings of any size. A full bathroom and laundry room complete this level. Upstairs, you’ll find a versatile flex space that offers an excellent opportunity for conversion into a spacious second-floor primary suite. The current layout also includes an open and airy bedroom with floor-to-ceiling closet storage, an equally large secondary bedroom, a third smaller bedroom, and a full hallway bathroom. A bonus room provides even more possibilities—ideal for a sitting area, home office, or reading nook. Outside, the oversized partially fenced backyard features mature trees that lend to added privacy. Situated in a quiet neighborhood near Bellemeade Park and just minutes from local shopping and dining, this property presents an exceptional opportunity to renovate, restore, and create value in a prime location. Don't let this opportunity pass you by - schedule your showing today!

2408 Oakland Avenue, Richmond
$320,000
5 Beds ⋅ 3 Baths ⋅ MDGA2009682 MLS
BACK TO ACTIVE!!! Buyers were unable to fulfill their home sale contingency. Welcome to this beautifully crafted 5-bedroom, 3-bath Stucco home, perfectly situated on a one-acre lot in charming Oakland, MD. With its timeless exterior, durable metal roof, and two car detached garage, this property offers both classic style and long-lasting function. Step inside to discover a light-filled, well-designed layout that blends comfort and space. The fully finished basement expands the home's livable space with laundry, a half bath and large family room. Located just minutes from Deep Creek Lake, shops, dining and four-season recreation, this exceptional property combines privacy, convenience and high end living in one of Western Maryland's most desirable destinations. Whether you are looking for a primary residence in or a spacious second home, this Oakland gem delivers it all!! If an active duty solider or veteran is interested in the house, the loan (through Planet Home Lending) is assumable at 2.75%.

531 S 3rd Street, Oakland
$289,000
MDGA2010666 MLS

216 E Alder St, Oakland
$370,000
4 Beds ⋅ 3 Baths ⋅ MDGA2010396 MLS
This charming traditional home in the desirable West Oakland area offers a perfect blend of comfort and style, while being close to schools and the hospital. With 4 spacious bedrooms and 2.5 bathrooms including a large primary suite, the layout is designed for both relaxation and entertaining. The inviting living area features a cozy brick fireplace, creating a warm ambiance for gatherings. The fully finished basement provides additional living space with convenient garage access. Step outside to enjoy your own personal oasis, complete with a fenced in-ground pool, kitchenette pool house, and a lovely roof deck that boasts stunning mountain views. The expansive lot of nearly an acre offers plenty of room for outdoor activities and gardening. Additional highlights include hardwood and carpeted flooring throughout, a traditional floor plan, and multiple patios and porches for enjoying the serene surroundings. With ample parking, including a driveway and attached garage, this home is ready to welcome you. Experience the perfect blend of indoor comfort and outdoor beauty in this exceptional property!

220 N 11th Street, Oakland
$285,000
3 Beds ⋅ 2 Baths ⋅ MDGA2010158 MLS
Charming 3 Bedroom Ranch Home on 20 Private Acres & Stream. Experience peace and privacy with this well-maintained 3-bedroom, 2-bath ranch-style home, perfectly situated on 20 scenic acres featuring a mix of woods, open fields & stream. This one-level home offers a spacious layout with a primary suite that includes a double vanity and soaking tub for ultimate relaxation. Additional features include a dedicated office, a cozy den, and plenty of natural light throughout. Outside, you'll find an oversized detached 2-bay garage with attached carport, plus a shed for extra storage. Whether you're looking for a private retreat, hobby farm potential, or just room to explore, this property offers endless possibilities. Schedule your private tour today!

122 Earl Hauser Road, Oakland