Oakland Real Estate, Homes, Condos for Sale in Richmond City, VA

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

$500,000

5 Beds ⋅ 3 Baths ⋅ MDPG2159302 MLS

Beautifully updated 5Bedroom home offers a perfect blend of modern & charm. The kitchen is a completely updated, featuring top-of-the-line stainless steel appliances, quartz countertops, updated cabinetry, a stylish tile backsplash, ceramic flooring, and is connected with Dining and large Living room. The refinished hardwood floors flow throughout the main level, complement all new fixtures Throughout the home . The House features 3 large bedrooms &2 updated baths w/ new vanities, toilets and modern tile upstairs. The lower level offers an additional kitchen/bar area with 2 large bedrooms and updated Bath, living room as well. A true in law suite. All Major things have been updated. Additional features include a concrete driveway, patio for outdoor enjoyment on a corner lot and fenced in yard. This home offerS Tranquility while still being conveniently near National Harbor, shopping, dining, transportation, and military bases.—this one will go quickly!!!!

8200 Bernard Drive, Fort Washington

$110,000

2 Beds ⋅ 1 Baths ⋅ MDGA2010202 MLS

Affordable starter home on an alley in the town of Oakland with many possibilities. This rancher offers hardwood floors, newer roof , newer siding, covered porch and a full basement that can provide more living space. The natural gas heat is another plus. You are also within walking distance to many things in downtown Oakland.

110 W Pennington Street, Oakland

$279,000

3 Beds ⋅ 1 Baths ⋅ MDGA2010268 MLS

Welcome home to this recently renovated single-family ranch featuring 3 bedrooms, 1 bathroom, and approximately 1,500 sq ft of bright, single-level living. Timeless hardwood floors flow through an open, easy layout that's ideal for everyday life and effortless entertaining. New windows invite generous natural light throughout, and the refreshed kitchen with modern finishes anchors the heart of the home, offering plenty of room for meal prep and casual gathering. Set on a generous corner lot, the property provides space to garden, play, or unwind. A privacy fence along the back adds seclusion, perfect for pets, kids, and weekend get-togethers on the lawn. Tucked in a quiet, desirable neighborhood just minutes from schools and downtown Oakland, this move-in-ready home blends comfort with convenience. With thoughtful updates and one-level living, it's a rare find! Schedule your tour today!

215 N 10th Street, Oakland

$135,000

2 Beds ⋅ 1 Baths ⋅ MDGA2009796 MLS

This charming 2 bedroom, 1 bath rancher in the heart of Oakland, MD is the perfect blend of comfort, convenience, and affordability. Move-in ready, this home features one-level living with a functional layout and low-maintenance design—ideal for first-time buyers, downsizers, or anyone looking for a simple, cozy retreat. Enjoy peace of mind with a brand-new boiler system being installed, ensuring efficient heating for years to come. The large, flat yard offers plenty of space for outdoor enjoyment, gardening, or future improvements. Situated in a prime location just minutes from local shops, restaurants, and schools, and only a short drive to Deep Creek Lake, Wisp Resort, and endless outdoor adventures. Whether you're looking for your first home, a rental investment, or a getaway close to it all, this property checks all the boxes. Don't miss this incredible opportunity to own a well-maintained home at an unbeatable price in a highly desirable area!

320 Coolidge Avenue, Oakland

$275,000

3 Beds ⋅ 2 Baths ⋅ MDGA2010108 MLS

An extremely charming 3 bed 2 full bath home located on one of the most desired and convenient streets in Oakland and the gateway to the valley. This home has had recent tasteful upgrades and TLC making it move-in ready and with a sturdy oversized garage and partially fenced in side yard, the comforts of home are everywhere.

648 S 3rd Street, Oakland

$132,000

3 Beds ⋅ 1 Baths ⋅ MDGA2010022 MLS

Nice starter or ender upper home located in Oakland on a level lot. Home features 3BR-1BA, hardwood flooring, hot water baseboard heating with natural gas. Home needs a little TLC but very affordable at this price. Paved driveway off of Poplar Street for easy access although the home has an Oak Street address. Roof being pressure washed 07/12/2025 and gutters cleaned out same day. Full basement allows for future living area expansion.

723 E Oak Street, Oakland

$320,000

4 Beds ⋅ 2 Baths ⋅ MDGA2009550 MLS

One level living in this duplex that has never been rented as two separate units but could be. Or, with minor modifications it could be one home with two separate living areas. Very well maintained home featuring brick fireplace on one side. Two kitchens, 2 bedrooms on each side with third area that could be another BR on each side. Two separate entrances, two garages. Full basement under 206 and 3-4' crawl with block walls and cement floor under 208. Nicely landscaped with great views of the farmland and pond. Public water and sewer but well could be used for 208. Natural gas generator. Most furniture could stay with the home and items not staying will be conspicuously marked. Very level lot and driveway leading to garage on each side. Recent improvements include metal roof and larger gutters, faux stone replaced with real stone, all but front shutters replaced and verticle siding and trim painted, natural gas generator. Have all the conveniences of in town living without paying the town taxes. 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.

206-208 N 10th Street, Oakland

$529,000

MDGA2003588 MLS

Here is an incredible opportunity to own a “bullseye” historic building, land and iconic outdoor fireplace that once housed the popular Sipside Lounge on 2nd Street in downtown Oakland! The possibilities of the property are endless, offering two great commercial spaces which are currently connected inside via a glass doorway. The other side currently houses an operating business - Flipside Sounds (vinyl record store since 2018). Flipside is amenable to tenant: landlord lease arrangement or vacating the premises depending on the wishes of the new owner. The former Sipside space is currently furnished with indoor and outdoor furniture such as tables, chairs, barstools, and lounge couches. Bar/restaurant hardware such as two refrigerators, icemaker, stainless steel sinks, requisite glassware and other barkeep items are also available in good working order. The property is just oozing with history; the foundation was built in 1877 and the building itself is circa 1909. The property was gutted and remodeled in 2018/ ‘19 to create an “upscale- hipster” interior. Unique details were incorporated into the rehab project, including two antique stained-glass windows, stage lighting, acoustic ceiling tile, two point-out storefront displays, custom wormy oak hand-built bar, climate-controlled wine storage loft, an indoor-outdoor performing arts sound system and a Bowers & Wilson Zeppelin sound system. Additionally, new flooring, bathrooms, ADA ramps, paint, electric, panel/breaker box, piping and four air conditioning units were also added. The upper level of the building offers 1900 square feet of potential (currently being used as storage) that could be converted to office space or a great studio apartment. If all this isn't enough, take a walk outside to the newly finished outdoor area; it will take your breath away! With approximately 2,600 square feet of covered and uncovered seating options, the hardest choice you need to make is where to sit. Perhaps you will prefer the handmade metal tables & chairs from India, or the cushioned lounge seating arrangement by the train tracks. And one of the neatest features and biggest draws to Sipside's open-air space is the massive stone woodburning fireplace from 1938 featuring the Oakland B&O Railroad as the backdrop. So many options here! Seating capacity is 42 inside and over 100 outside.

119 & 121 S 2nd Street, Oakland

$148,000

2 Beds ⋅ 1 Baths ⋅ MDGA2009400 MLS

This charming 2-bedroom, 1-bath house offers the perfect blend of comfort and potential. Step inside to find a cozy living space adorned with upgraded carpet and flooring, creating a warm and inviting atmosphere perfect for relaxing or entertaining. One of the standout features of this property is the massive garage, providing ample space for vehicles, storage, or even a workshop. With both the garage and living space separately metered, you can enjoy the flexibility of using the garage as a rental opportunity or keeping it as your personal sanctuary. You'll appreciate the practical upgrades throughout, including a new metal roof and new electrical systems, ensuring peace of mind for years to come. The spray foam insulation enhances energy efficiency, making this house a comfortable retreat in any season. With rental potential of $1200/month if tenant-occupied, this property presents an excellent opportunity for investors or those looking to supplement their income. Don't miss out on the chance to own this versatile gem that combines modern upgrades with significant income potential. Schedule a viewing today!

116 N 8th Street Unit #2, Oakland

$270,000

4 Beds ⋅ 4 Baths ⋅ MDGA2007582 MLS

NEWLY RENOVATED! So excited to be on the market with new carpet, paint , appliances, and roof!!! One-level living with great open views in town! 4 BR, (2 PRIMARY)) and 3 1/2 Baths, NEW outside decks on front & back of home with a large fenced-in yard (back/side). Located on a nice corner lot with lots of privacy. All bedrooms are spacious! Laundry room with plenty of storage. Large kitchen area overlooks dining room with archway and entrance to outside front deck. 2 Bedrooms on one side of home and 2 BR on other side, makes for lots of privacy! Many closets throughout! This is a must-see, great one-level living. Close to schools and huge open front yard views!

403 O Street, Oakland

$237,000

1 Beds ⋅ 3 Baths ⋅ MDGA2009146 MLS

Prime Commercial Opportunity with Rental Apartment & Multiple Uses! Seize this incredible commercial business opportunity in a high-demand location, just minutes from a thriving commercial district. Currently operating as a successful hair salon, this versatile property is perfect for a variety of businesses, including retail, office space, or other service-based ventures. Plus, the included rental apartment can provide an excellent income stream or on-site living convenience. Whether you're an investor or a business owner looking to expand, this property offers endless potential. 12' x 20 storage building included. Don’t miss out—schedule a viewing today!

13903 Garrett Highway, Oakland

$290,000

3 Beds ⋅ 2 Baths ⋅ CVR-2516605 MLS

Come see this beautiful 3 BR, 2 BA townhome located in the city's Church Hill/Oakwood neighborhood! Enjoy mostly-maintenance free living with the front yard lawn care and landscaping included in the low monthly HOA ($88/mo), as well as roof maintenance. This home features beautiful laminate flooring throughout the living space and bedrooms, kitchen with cherry cabinets, all appliances that convey, recessed and pendant lighting, and more. Off from the kitchen is a dining nook, a dedicated laundry/utility room, and a first floor full bathroom with stand up shower. Upstairs, you'll find the primary bedroom with a spacious walk-in closet, and an attached jack-and-jill bathroom that connects to both the primary bedroom and hallway. Outside, you'll love the full front porch and newly stained back deck and landscaped yard.

1404 N 33rd Street, Richmond

$171,000

4 Beds ⋅ 2 Baths ⋅ MDGA2008794 MLS

Endless Potential! This diamond in the rough is ready for your vision and creativity. A fantastic opportunity to make this home truly your own. Bring your tools and imagination---this home is waiting for a makeover. Great Investment property! It was used as a Duplex, home needs work but offers a great value for the right buyer. Newer furnace, newer windows installed throughout. Hardwood floors, covered front porch, beautiful backyard area. This property has .96 of an acre, several sheds for storage included. Around 2000 +/- sq. feet of living space. Full basement with tons of storage, finish off for added sq. footage. Call today to set up a viewing of this property.

5459 Hutton Road, Oakland

$264,500

3 Beds ⋅ 2 Baths ⋅ MDGA2009614 MLS

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

$73,900

3 Beds ⋅ 1 Baths ⋅ MDGA2009294 MLS

3 bedroom 2 story dwelling on quiet city street. enclosed porch front & rear. 2 car Detached garage. Estate property

112 E Pennington Street, Oakland

$240,000

MDGA2007686 MLS

1.41 acres off Rt. 219 (Garrett Highway) located close to many established national commercial businesses. High traffic visibility, corner lot. Adjacent 1.15 acre (lot A), also for sale. Call listing agent to find out more about this desirable building lot.

N 4th Street Lot B, Oakland

$115,000

4 Beds ⋅ 3 Baths ⋅ MDGA2007922 MLS

Potential Potential Potenital! Home is being sold 'As-Is' and is in need of some work. This 4 bedroom 1 full bath and 2 half bath home is situated on a beautiful 3-acre lot with a stream running through it. There is a bridge across the stream to get to the other side of the property. The large yard with mature trees throughout is perfect for outdoor activities! Detached 2 car garage. The property is centrally located between Oakland and Deep Creek Lake!

399 Kings Run Road, Oakland

$329,000

3 Beds ⋅ 1 Baths ⋅ MDGA2008126 MLS

This home has been renovated from top to bottom! Offering new siding, windows, doors, plumbing and electric. Boasting three bedrooms, a great kitchen with a farmhouse sink and a butcher block island, finished lower level and a stone electric fireplace for your enjoyment. The home feels warm and inviting from the moment you walk in, shiplap walls are just one more great feature. The wrap around deck and large yard provides plenty of room to enjoy family and friends. Located just a few minutes from downtown Oakland, this home checks off all the boxes.

644 Silver Knob Road, Oakland

$340,000

5 Beds ⋅ 3 Baths ⋅ MDGA2007874 MLS

Beautiful stone home located in the historic town of Oakland. This home offers an expansive, updated kitchen with a large island, granite countertops, and an abundance of soft close cabinets. The bathrooms were recently remodeled, and a new roof was installed in 2021. Sitting on two town lots, you have a spacious .80 acres to call your own. The five bedrooms, two levels of living space and a two-car attached garage, provide plenty of space for everyone. The exterior offers a shed, level yard, rear patio, stone walkway, and a paved driveway. Shopping, restaurants, schools, and grocery stores are just minutes away, call today to preview this wonderful property!

413 N 2nd Street, Oakland

$515,000

3 Beds ⋅ 3 Baths ⋅ MDGA2007572 MLS

Experience luxury living in this fully remodeled home with nearly 3,000 sq ft of space. Every room has been thoughtfully updated, from new luxury vinyl flooring to stunning quartz countertops. The elegant and spacious primary bedroom features an en suite and vaulted ceilings, providing a serene retreat. A new central air conditioning system has been installed for the main level, ensuring comfort throughout the home. The stunning new kitchen is complete with a large island offering seating space, perfect for casual dining and entertaining. The full, finished basement is designed for gatherings, featuring a built-in bar finished in barn wood. This picturesque 2.76-acre lot comprises two separate 1.38-acre parcels, with the second lot being buildable, offering potential for future development or expansion opportunities. Some additional features are an attached garage with inside access, large back deck, and fire pit in the backyard. Just 10 minutes from Wisp Resort, Deep Creek Lake, and Oakland. Truly the center point for everything Garrett County has to offer. Don’t miss out!

2880 Sand Flat Road, Oakland

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