Oakland, MD 2 Bathroom Homes for Sale

Cozy cottage with split lakefront and Type A dock located in the serene quiet Penn Point Cove. This quaint home has plenty of room for family, guests and entertaining. The covered & heated outdoor deck facing the lake is a great place for morning coffee and evening dinner. The large, bright kitchen & dining area is another great entertaining space with quartz countertops, stainless steel appliances and plenty of room for large family gatherings. The home has 2 bedrooms on the main floor, a roomy living area with fireplace, full bathroom and a bonus sunroom with a wood burning fireplace. Upstairs has a great bunk room bedroom that can easily sleep 4 people, plus another living room and bathroom with a claw foot tub and shower. Beautifully landscaped outdoor area has a firepit space, a detached garage with plenty of storage area and an easy walk to your dock area. Great places to watch some of the best sunsets! This home will convey turnkey furnished with a few seller exceptions. Schedule your tour today, this home has so much to offer.

187 Lower Penn Point Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$269,900

Major renovations on this 2BR, 2BA Laurel brook two level townhome! Updates include new flooring, paint, fixtures, countertops, bathrooms and furnishings. One of the best dollar for dollar values still available at Deep Creek Lake and located within one mile of shopping, dining, entertainment, marinas and more! Enjoy a park-like setting with mature trees, common areas for relaxing or picnics and a quiet stream bordering the community. Conveys virtually turn-key based on final price.

5 Laurel Brook Dr Unit #5, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700

$290,000

Welcome to 635 Dennett Road! This beautifully maintained 2023 home offers the perfect opportunity to enjoy convenient living on 5 acres with a large yard. The expansive, level yard provides endless possibilities for outdoor entertaining, gardening, or simply relaxing. Inside, you'll find an open floor plan with bright finishes, a spacious kitchen, and comfortable living spaces designed for both everyday living and gathering with family and friends. Lovingly cared for, this home is truly move-in ready. Located just behind Southern High School and only minutes from town, you'll enjoy the tranquility with the convenience of nearby shopping, dining, and everyday amenities.

635 Dennett Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$325,000

Distinguished English Tudor Home in a Private Setting. Nestled on a quiet street with Town of Oakland services, this distinguished English Tudor home offers the perfect blend of privacy, charm, and convenience. Designed with family living in mind, the home features three (3) bedrooms, two (2) full bathrooms, and multiple bonus rooms that provide endless possibilities for a home office, playroom, hobby space, or guest accommodations. Step outside to enjoy the inviting backyard deck—an ideal setting for entertaining, relaxing, or enjoying peaceful evenings. Located in one of Oakland’s most desirable neighborhoods Country Club Acres, this property offers a welcoming atmosphere and timeless curb appeal. Completing the home is a convenient one-car integral garage. Roof w/ warranty installed 2026 Call today for your private tour!

520 Palmer Ln, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$325,000

3BR, 2BA home near Broadford Lake & Southern Middle school. Setup perfectly for one-level living with room to expand in the full, unfinished basement. Comfy living room, eat-in kitchen, separate laundry room and recent bathroom remodel. Central location to hospital, shopping and town businesses. Spacious, level back yard offers plenty of sunshine. 2 car attached garage with only a few small steps into the main house.

610 Harvey Winters Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700

$499,900

Wake up to breathtaking views of Deep Creek Lake every single day from this beautifully updated 3-bedroom home, complete with private lake access in a quiet, peaceful cove. Huge windows throughout invite in an abundance of natural light while framing the surrounding scenery, blurring the line between indoors and out. The open-concept kitchen features beautiful new quartz countertops and flows seamlessly into the living space, creating the perfect spot to entertain or simply relax while soaking in the views. Step outside onto the oversized wrap-around deck — an entertainer's dream and the ideal place to sip your morning coffee or wind down during sunset. A private barrel sauna and hot tub provide the ultimate way to unwind after a day on the water or the slopes, all while a detached two-car garage offers plenty of storage for your lake-life gear. Efficiency is highlighted with multiple heating and cooling zones throughout the home. A new homeowner will enjoy the luxury of high-end appliances and laundry rooms on each floor. This is truly the ideal four-season home: warm up by the cozy pellet stove on chilly winter nights, then soak up the sun and dive into all the lake activities summer has to offer, including kayaking, canoeing, swimming, and fishing right from your private community lake access. With its unbeatable combination of views, natural light, and resort-style relaxation, this home is perfect as a full-time residence or vacation retreat. Don't miss your chance to own a piece of Deep Creek Lake paradise. Call today for more details or to schedule your private tour!

101 Sobriety Way, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$259,900

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:

$595,000

Ultimate lakefront living awaits at Red Run! This stunning 2-3BR, 2BA condo features a second-floor loft and a versatile den easily used as a 3rd bedroom. Enjoy breathtaking lake views from your gorgeous primary suite and private lakeside balcony. Extensively upgraded with a extensively upgraded kitchen boasting granite countertops and soft-close cabinetry, a newly remodeled laundry room with a new water heater and sink, an upgraded electrical panel, and premium cement-backed luxury vinyl plank flooring for ultimate durability. Stunning new shiplap ceilings with recessed lighting illuminate the freshly painted main living spaces, complete with a cozy wood-burning fireplace. Includes an assigned deep-water boat slip, outdoor storage, and access to 11 acres of incredible amenities: a heated pool, tennis courts, playground, kayak racks, and a stone fire pit. Major community updates include a new metal roof and resurfaced courts. Just minutes from downtown Oakland, Garret Cinemas, and shopping! Seller will sell his 2011 Sea Ray 195 with 4.2 L EFI engine for $4500.00 OBO "As=Is " see photos and dock slip

193 Red Run Rd Unit #1-B-3, Oakland

Listing courtesy of RE/MAX Results. Contact: (301) 698-5005

$299,000

Escape to the beauty of the mountains with this 4-bedroom, 2-bath log home situated on 15 scenic acres just south of Deep Creek Lake. Offering two full levels of comfortable living space, this well-maintained home is ideal as a full-time residence or vacation getaway along with the modern convenience of high speed FIOS internet service that is coming soon. The inviting interior features hardwood flooring in the kitchen and living room, luxury vinyl flooring throughout all bedrooms, and a spacious kitchen equipped with stainless steel appliances. The completely renovated primary suite offers a private retreat with luxury vinyl tile flooring and an updated en-suite bath featuring a beautifully tiled tub/shower, new vanity, and modern lighting. Designed for year-round comfort, the home includes a newer propane furnace along with a functional wood burning and coal furnace for supplemental heating, convenient nearby wood storage area, and wifi enabled thermostat. Outside, enjoy the low-maintenance metal roof, expansive deck, large storage shed/outbuilding with electricity, and a generous yard that leads up to additional acreage. The 15-acre property offers the perfect blend of open fields and partially wooded land, with breathtaking mountain views stretching across Western Maryland toward nearby West Virginia. Whether you're riding ATVs or side-by-sides, hunting, hiking, or simply enjoying the outdoors, this property provides endless recreational opportunities right outside your door. This listing is two adjoining parcels - a 1.7 acre parcel with the home that leads up to an additional 13.3 acre parcel. Both parcels have public water access hookups along with the public water hookup for the 13.3 acre parcel already in place. Conveniently located south of Deep Creek Lake and Wisp ski resort - and within an easy drive to the charming mountain towns of Davis and Thomas, West Virginia, as well as Timberline ski resort, you'll have year-round access to boating, skiing, hiking, dining, and outdoor adventure. If you've been searching for a peaceful mountain retreat with acreage, views, and endless recreational possibilities, this exceptional log home is one you won't want to miss!

2189 Table Rock Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$399,900

Double lots! Lot 4 & 5 of Hunting Ridge Estates will be sold together to bring up a total of .96 acre on your 2476 sqft. of finished living space home awaits you including your finished basement. Metal Roof is only 4 years old. Windows and doors are only 6 years old. Location, location...Welcome to 321 Deer Park Hotel Rd. where your mountain retreat will be just outside the city limits with only being only 10-15 minutes to nearly all the amenities the surrounding area has to offer. As you walk on to the nearly an acre of beautifully mature trees and landscaped double lot property where the only thing you'll hear is birds chirping and feel a sense of peace. Featuring a true mid-century modern. Fully updated 3 spacious bedrooms with extra long closets with 2 full bath, laundry/mud room and walkout 10 x 30 covered deck on the main floor. High end appliances and granite countertops along with a southern style porcelain sink compliments the kitchen. A major bonus is the washer and dryer are on the main floor. There are refinished hardwood floors and waterproof LV flooring throughout the entire house. With the fully finished walkout basement you will find many multi-use spaces. Custom bar, gym, reading room with a wood burning stove, double shop sink, extra full size refrigerator and other extras. As you walkout the basement, you will have a covered 7 person hot-tub with mounted 32 inch TV. There are 4 raised bed gardens, firepit, and a horseshoe pit to compliment the outside property along with 1 large shed w/electric and another large shed with covered deck with water and electric. and an additional garage/shop with a wood stove. There is also a 50-Amp/whole house manual transfer switch in the main garage to hook up your generator to should the power go out as well as a walkup attic for more storage. Parking for 9 plus vehicles on a double sealed driveway. Come find some peace and quiet and make this "stay-cation" style home yours. There are so many extra major renovations not listed that you just have to see to believe.

321 Deer Park Hotel Rd, Oakland

Listing courtesy of Houwzer, LLC. Contact: 2028668787

$340,000

Escape to the mountains at 254 Little Mountain Road, where privacy, comfort, and outdoor adventure come together on nearly 5 acres in the sought-after Backbone Ridge community. Surrounded by mature trees and mountain scenery. Inside, you'll find warm wood accents and a cozy wood-burning fireplace that anchors the inviting living space. Multiple gathering areas provide flexibility for entertaining, relaxing, or creating a home office, hobby room, or additional recreation space. Recent improvements include a new roof (2021), well pump (2023), pellet stove (2023), and kitchen appliances (2024), offering peace of mind for years to come. Step outside and enjoy covered porches, a fire pit area, and plenty of room to roam, all surrounded by the natural beauty of Western Maryland's mountains. Located near Deep Creek Lake, Wisp Resort, and Canaan Valley, this property provides easy access to year-round recreation including skiing, hiking, fishing, boating, and more. With vacation rentals prohibited, Backbone Ridge maintains a quiet residential atmosphere that's ideal for a primary residence, seasonal retreat, or weekend mountain getaway. Experience mountain living at its best—schedule your private showing today.

254 Little Mountain Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$375,000

Welcome to Ricky's Retreat, a beautifully renovated mountain retreat nestled on 1.17 private wooded acres in the heart of Garrett County. Ideally located just minutes from Deep Creek Lake, Wisp Resort, Swallow Falls State Park, and downtown Oakland, this turnkey property offers the perfect balance of privacy, recreation, and modern comfort. Originally built as a raised ranch, the home has undergone extensive improvements in recent years, transforming it into a spacious and inviting 4-bedroom, 2-bath getaway. The main level features an open-concept design with warm wood accents, updated flooring, and a renovated kitchen complete with stainless steel appliances, modern countertops, and ample space for gathering. Three bedrooms and a beautifully updated full bath with a custom tiled walk-in shower complete the upper level. The fully finished lower level significantly expands the living space, offering a large recreation room, game area, additional sleeping accommodations, laundry area, and a second fully renovated bath. A traditional staircase replaced the original spiral staircase, creating improved functionality and flow between levels. Outdoor living is where this property truly shines. Multiple gathering areas have been thoughtfully created throughout the acreage, connected by gentle walking paths that lead to unique viewpoints and hangout spaces overlooking the surrounding mountain ridge. Enjoy evenings around the fire pit area, unwind in the hot tub, or relax on the expansive rebuilt deck surrounded by nature. Mature trees, abundant privacy, and a peaceful setting make it easy to enjoy every season. Whether you're searching for a primary residence, second home, or investment opportunity, this well-maintained and extensively updated property offers the ideal Deep Creek lifestyle with room to gather, entertain, and make lasting memories.

1499 Foster Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$279,000

Tucked away on a private lane and surrounded by the beauty of the woods, this charming 3-bedroom, 1 full bath and 1 half bath log home offers the perfect mountain retreat on 2 peaceful acres in Garrett County. Ideally located just minutes from Swallow Falls State Park, Muddy Creek Falls, and the Youghiogheny River, this cozy cabin is a dream destination for outdoor enthusiasts seeking hiking, fishing, kayaking, and year-round adventure. Inside, you’ll find warm rustic charm with comfortable living spaces, a gas fireplace stove for cozy mountain evenings, and a bunk room perfect for hosting family and friends. One of the three bedrooms features its own private half bath and private deck, creating a relaxing escape after a day outdoors. Enjoy quiet mornings and unforgettable evenings from the covered front porch, surrounded by nature and mountain serenity. Conveniently located only 10–15 minutes from Deep Creek Lake and Wisp Resort, this property offers easy access to boating, skiing, dining, and entertainment while still feeling wonderfully secluded. Priced to be an affordable vacation home in today’s market, this is an incredible opportunity to own the ultimate log cabin getaway in one of Western Maryland’s most sought-after outdoor destinations.

277 Cheeks Ln, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$325,000

Tucked within the sought-after Yough Mountain Resort community, this beautifully remodeled 4-bedroom, 2-bath mountain retreat blends rustic charm with thoughtful modern updates. Warm wood finishes, high ceilings, and inviting gathering spaces create a cozy lodge-style atmosphere, while upgrades throughout add comfort and convenience. The home features two full kitchens with granite countertops, stainless appliances, a pot filler, and more - perfect for hosting family and friends. A spacious second living area offers added flexibility for entertaining or guest space. Enjoy the outdoors from the screened porch, wraparound deck, fire pit, and front and back patios, all surrounded by peaceful wooded scenery. Additional highlights include a propane furnace, tankless hot water system, UV light water filtration, water softener, whole-house generator, newer roof, carport, and wood shed. Located in a gated recreational community with access to over 50 miles of private roads and trails for ATVs, snowmobiling, hiking, hunting, fishing, and river access, this property is an ideal year-round getaway, vacation rental opportunity, or full-time mountain home. Call today for details!

2448 Birchwood Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$2,499,900

Rare opportunity to own 327+/- acres of scenic countryside featuring a mix of open pasture, mature woods, and flowing stream frontage along Block Run. This 4-bedroom, 1.5-bath farmhouse is privately tucked among rolling fields and mountain views, offering endless potential for farming, recreation, hunting, ATV trails, or a private estate. Multiple barns and outbuildings provide ample storage and agricultural use, while the diverse landscape creates a truly picturesque setting. Abundant wildlife, wooded acreage, and open meadows make this a one-of-a-kind property with incredible privacy and versatility—all within a peaceful Garrett County setting, just minutes from Downtown Oakland!

83 Bethlehem Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$299,000

Charming and well-maintained, this 4-bedroom, 1.5-bath traditional home offers the perfect combination of comfort, character, and convenience. Built in 1952 and thoughtfully cared for, the home features beautifully refinished hardwood floors, inviting built-ins, and a cozy living room with a functional wood burner. With over 1,500 square feet of living space, the spacious layout includes an eat-in kitchen connected to the family room, creating an ideal setting for everyday living and entertaining. One of the home's standout features is a unique second-floor room with two separate entrances, offering the flexibility to serve as a fifth bedroom, home office, playroom, guest suite, or hobby space. Designed with practicality in mind, the home also offers abundant storage throughout, including built-in cubbies and a large walk-in closet with dual access. The full walkout basement with garage access provides additional storage and endless potential. Situated on a private 1.32-acre lot backing to trees along Route 219, this property combines peaceful surroundings with easy access to local markets, restaurants, parks, and everyday amenities. Outside, enjoy the detached garage, carport, outbuildings, ample parking, and two wraparound driveways that add both convenience and curb appeal. Move-in ready and full of warmth and charm, this property is a wonderful place to call home.

17921 Garrett Hwy, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700

$335,000

Park like, setting on 1.7 acres in Pleasant Valley, 4 Br, 2BA ranch home with full basement. Close to town yet, peaceful and secluded. Home features 4 Bedrooms, primary has 2 walk-in closets & large primary bath with walk-in shower. Front living & dining areas, with main entrance from the covered front porch. Open Kitchen, breakfast nook and den area with wood burning fireplace. Opens to covered back porch overlooking enclosed large back yard. 3 Bedrooms and full bath. Full basement, used for storage, however has plumbing for additional bath that could be installed, also has walk out to back yard. 2 Car garage leads to back entrance with washer dryer and pantry off kitchen. Lots of room and all situated on a level lot, with paved driveway. Call for you private showing today! This one will not last long.

105 Jasper Riley Rd, Oakland

Listing courtesy of The KW Collective. 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

$191,409

Welcome to The Wise Quack - our cozy cabin in the center of Deep Creek Lake activities…all 4 seasons! If you’re looking for a weekend or holiday retreat, this is it! The Wise Quack is a successful short-term rental with rave reviews. The home has three bedrooms, two full bathrooms, a fully equipped kitchen, laundry room and lots of outdoor living space. There is parking for 6+ cars on the property. The home is private, set in beautiful, wooded surroundings on almost one acre. The fenced-in front yard is great for the little ones or to let your fur babies run free. The “fun factor” comes in a tiny-house game room which houses a ping pong table, darts, board games, etc. as well as outdoor games such as corn hole, spike ball, and horseshoes. The detached garage is perfect for storing your kayaks, canoes, paddle boards and bikes. A custom-built fire pit is in the back with lots of wood for your use and solar-powered lights for fire-side chats. The front deck overlooks trees above the Youghiogheny River. The back deck has a grill for your use. The kitchen is fully stocked with gas stove, dishwasher, refrigerator, microwave, and two peninsulas with seating for 8. If you want to buy more than a house, come see this wonderful property. It can be yours to enjoy year-round or rent out when you’re away. Updates include the following, all done in 2021: windows & sliding glass door, flooring, electric fireplace, lighting and ceiling fans, washer, dryer, dishwasher, ceramic tile, accent walls, tiny house game room. Additional updates include: new insulated crawl space (2023), and a new tin roof - tin lasts 50 years! (2024). Year-round activities include skiing, kayaking, stocked trout fishing, white water rafting, hiking, biking, golfing, horseback riding, boating and swimming. You are close to Wisp Resort, Deep Creek Lake and the Youghiogheny River (across the road). Surrounded by 8 state parks, the Wise Quack is turnkey, has all the comforts of home and is centrally located to shopping and restaurants. More than beautifully designed and professionally maintained, this property is also profitable. This is a manufactured home, not a trailer, built in 1999. Please contact the listing agent before scheduling through ShowingTime as the short-term rental operates year-round and may have guests. All offers considered.

8956 Oakland Sang Run Rd, Oakland

Listing courtesy of Taylor Properties. Contact:

$269,000

Tucked away in the scenic beauty of Yough Mountain Resort, this exceptional 2-bedroom, 2-bath log cabin offers the perfect blend of rustic charm and modern comfort. Spanning two stories, this immaculately maintained home has seen thoughtful renovations in recent years, creating a warm and inviting retreat that’s move-in ready. Step inside to discover cozy living spaces ideal for relaxing after a day in nature, with classic log cabin character throughout. Whether you're looking for a peaceful weekend escape or a year-round getaway, this home delivers comfort, privacy, and timeless appeal. Surrounded by the natural beauty of Garrett County, Yough Mountain Resort is known for its expansive scenic views and outdoor lifestyle. Enjoy direct access to miles of trails perfect for hiking, biking, and ATV adventures—right from your doorstep. If you’ve been dreaming of a private mountain retreat where you can unwind, explore, and recharge, this beautifully updated cabin is your opportunity to own a piece of Western Maryland paradise.

400 Bear Dr E, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700

$729,000

5 Beds ⋅ 2 Baths

Lake cottage (5 Bedrooms) on large level lot with path to your own private class A dock & 25' of Lakefront, directly across the street. This comfy (one level living) cottage sits on 1.8 level acres with 2 storage garages and mature landscaping. 5BRs, open living, dinning & kitchen area, with lots of sunlight. 1 full & 1-1/2 bath, with 5 Bedrooms! Laundry room located off back of the home. Cute and cozy, well maintained and move in ready, with sleeping for 12 heads on beds (several bunks)! 2 garages with plenty of storge for your lake & yard toys. The lot has mature landscaping & circular paved driveway, for easy in and out during all seasons. Private path to your lakefront dock is an easy walk across the street. Nice level lake front, no steps to go onto your dock! Buydown Included on Lakefront. Great opportunity to get onto the lake at an affordable price, call agent to set up an appointment or with any questions.

222 Skippers Point Rd, Oakland

Listing courtesy of The KW Collective. Contact:

$999,000

Remodeled 4BR/2BA lakefront A-frame with two deep water dock slips! Impressive renovation from top to bottom, this home has everything you are seeking in a vacation home AND a huge, fenced in yard surrounded by massive trees, fire pit and storage building. Features include a massive stone fireplace (wood burning), hot tub with lake views, large kitchen with island, custom tile showers & bathrooms with cedar accents, stylish bedrooms & decor, wet bar in rec room, recently replaced deck with covered concrete patio, spacious bedrooms, whole house dehumidifier, mini-splits and some handicap accessible features. Enjoy filtered water views though its a commanding view of your surroundings from a mountaintop perch. Located at the end of a peaceful cul-de-sac with minimal traffic but also centrally located to all lake activities. Sold furnished! Established vacation rental - 'Fox Den'

137 Paradise Gardens Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700

$349,000

Looking for a vacation spot or main living, Check out this nicely remolded home in a gated community. 3 bedrooms, 1 1/2 bathrooms, main level laundry room. Great rustic touches . Detached Garage with pellet stove. Yough Mountain Resort is the ultimate mountain escape! Nestled in a quiet, secluded area, this beautifully updated retreat offers modern comfort in a rustic Access to over 50 miles of private roads and trails—perfect for ATVs, snowmobiles, hiking, river access, fishing, and hunting. . Whether you're looking for a peaceful weekend getaway or a year-round hideaway, this home offers the perfect blend of tranquility and outdoor fun.

552 Black Oak Dr, Oakland

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

$259,500

Affordable well maintained 2 Bedroom 2 Bath townhouse style condominium less than 1 mile from Deep Creek Lake. Offering low maintenance and a pleasant setting, the property works well for full and part time ownership. The unit offers recent upgrades and Includes 2 parking spaces along with public water, sewer and weekly trash pickup. Shown by appointment only.

13 Laurel Brook Dr Unit #13, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$275,900

Welcome to this beautifully updated 1901 home in the heart of downtown Oakland, where historic character meets modern convenience. Situated on a charming lot with mature landscaping and blooming trees, this home offers timeless curb appeal with a welcoming covered front porch perfect for relaxing and enjoying the neighborhood. Inside, you’ll find modern updates throughout while preserving classic architectural details. The main level features spacious living areas filled with natural light, a thoughtfully updated kitchen with stylish cabinetry, stainless steel appliances, and sleek countertops, as well as the convenience of a main-floor bedroom and full bath—ideal for guests, a home office, or single-level living. Upstairs, the home offers three additional bedrooms and another full bathroom, providing plenty of space for family, guests, or flexible living arrangements. Large windows throughout the home bring in abundant natural light while highlighting the home’s historic charm. Outside, enjoy a private driveway with carport, offering convenient off-street parking. The property is surrounded by established greenery and colorful seasonal landscaping, creating a peaceful setting just moments from everything downtown Oakland has to offer.

449 S 3rd St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$219,000

1 Beds ⋅ 2 Baths

Nestled on nearly 3 acres across two parcels, this chalet-style home offers a rare opportunity to create your retreat just minutes from the lake. Renovate the existing structure, or start fresh and build the lake-area retreat or cabin you’ve always imagined. The level, wooded setting provides privacy, peace, and plenty of room to expand, garden, or simply enjoy nature. With well and septic already in place, the groundwork is set for your vision. Located just 5 minutes from all lake amenities and activities, you’ll enjoy easy access to boating, fishing, swimming, and year-round recreation while still savoring the tranquility of your own private acreage. Parcels of this size and proximity to the lake are a rare find—don’t miss the chance to make this blank canvas your masterpiece.

141 Montana Ln, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$379,999

NEW CONSTRUCTION from Lyv Homes! 3BR/2BA, 1464sf contemporary style home fronting on the 13th hole of the Oakland golf course. This property combines scenic views with modern design and outdoor living. Key features include multiple wood-burning fireplaces, Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets and drawers, quartz countertops, stainless steel appliances, a custom island with quartz countertops, custom aged barrel interior trim that complements the versatile color palette, and high energy efficiency. Enjoy convenient one-level living with a sensible floor plan. The home is located minutes from downtown, restaurants, and shopping, with easy access to town parks, sport courts, trails, the Yough River, and both Herrington Manor and Swallow Falls state parks. NO HOA! Specific finishes subject to change.

654 N Bradley Ln, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700

$287,500

Charming ranch-style home located in the desirable Southern Pines neighborhood. From the moment you enter, you’ll appreciate the warm and inviting feel of the open layout. The main level features three comfortable bedrooms, two full bathrooms, beautiful hardwood flooring, and a seamless kitchen, living, and dining area that creates an ideal space for everyday living and entertaining. The recently finished lower level expands the living space with a spacious family room and plenty of storage. Step outside to enjoy the level, fenced backyard, and rear deck — perfect for gatherings, pets, or simply relaxing with family and friends. New furnace in 2026. Conveniently located just minutes from schools, shopping, and restaurants in the Oakland area, this home offers both comfort and convenience in a wonderful neighborhood setting.

505 Southern Pines Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700

$265,000

Welcome to this well maintained 4-bed, 2-bath ranch home on a generous corner lot in Oakland, MD. Inviting curb appeal with stone exterior and mature landscaping sets the tone. Step inside to a bright and spacious main level featuring gleaming hardwood floors, a large eat-in kitchen with ample cabinetry, and an open living area perfect for gatherings. Enjoy three main-level bedrooms and a full bath, while the mostly finished lower level adds valuable living space including a family room, additional bedroom, laundry room, and second full bath. Relax and entertain outdoors in the private, fenced backyard with patio space and a hot tub, or take advantage of the attached garage with workshop space and ample driveway parking. Great storage throughout, abundant natural light, and a versatile floor plan to enhance everyday living. Conveniently located within walking distance to Southern Garrett High School and close to local shopping and dining. Don’t miss this exceptional move-in ready home with character and functional spaces.

127 S Oakhall Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$185,000

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:

$234,000

***BACK ON THE MARKET, don't miss this one a second time! Welcome home to this solid, ranch style home on one of Oakland's most convenient streets. Built in 1954, this 3-bedroom, 2-bath home delivers 1,520 sq ft of comfortable living, plus a partially finished full basement ready for your vision, whether that's a rec room, home office, or extra storage. The metal roof means peace of mind for years to come, and the outbuilding out back is a serious bonus, ideal as a workshop, hobby space, or additional storage. A paved driveway offers easy access and plenty of room for guests. Inside, the layout flows naturally with carpet and ceramic tile underfoot. The kitchen is fully equipped with refrigerator, electric oven/range, and dishwasher, and the main-floor laundry means one less trip up and down the stairs. It's a home that just works. Step outside your door and find shopping, parks, medical services, and local businesses all within easy reach and the outdoor recreation and natural beauty of the Deep Creek Lake area just a short drive away. This is the kind of neighborhood where people put down roots. Whether you're buying your first home, rightsizing, or anything in between, this one deserves a look. Schedule your showing today. (Note: Due to sudden change of Seller's circumstances, this will be a short sale.)

1021 E High St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$550,000

Make it your own! This 2-acre parcel comes with two additional parcels of 17.96 and 24.23 acres for a total of 42.19 acres. The 2-acre parcel is improved by a fully furnished (26’X42’), 3-bedroom, 2-bathroom Ranch style dwelling and a large parking area. The interior offers a spacious living room, and an eat-in kitchen with all appliances, furniture and window AC units. The land is un-zoned forest that borders over 2000 acres of state forest. The 42.19 acres is fully wooded with mature mixed hardwoods ready for harvest and market; the timber alone has an estimated value of $110K to $125K alone. The property overlooks the Youghiogheny River Valley and is 5.3 miles from town center McHenry and Deep Creek Lake.

98 Bear Run Rd, Oakland

Listing courtesy of 1 Real Estate Source LLC. Contact: 3013878300

$575,000

With some minor modifications to the unit, it is possible for this condo to be rented as two separate condos (501 two BR and 701 one BR). Lakefront living at it's best can be found in this completely renovated spacious condo. This three-level unit is the perfect place to get away together! With space to come together and space to escape, this unit promises both privacy and togetherness for a memorable Deep Creek Lake experience! The first level has a full kitchen with wine fridge and attached living room with an electric fireplace, queen sleeper sofa, high top table with stools and a breathtaking balcony. Just up the stairs, enjoy the king bed in a loft bedroom that overlooks the living room and towering two-story window facing Deep Creek Lake! Also on this level is another bedroom with a Queen bed that shares a hallway bathroom with luxury finishes and a walk-in shower. On the top level you will enjoy even more space and accommodations. The 7th floor level has an additional hallway entrance for more privacy. Relax in the King bed and look out to your private balcony with gorgeous lake views. This space also features a well appointed luxury bathroom with walk-in shower and double bowl sinks. An additional mini-fridge and Keurig coffee maker provide easy access if you don't want to go downstairs. Up above in the vaulted loft curl up in the Queen size bed and take in panoramic sunrise views from every angle. Head down to the sandy beach to watch the water gently roll along the sandy shore of the resort’s private beachfront. No matter the season, there is plenty to keep you entertained with an on-site indoor pool, game room, fitness center, and more! 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.

20160 Garrett Hwy Unit #F501-701, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$269,500

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: 3013874700

$285,500