Stilwater, Oakland, MD Single Family Homes for Sale

Situated in a prime location just minutes from Wisp Resort and Deep Creek Lake. The value here is in the land and location. With nearly one acre, the property offers strong potential to build a custom home or vacation retreat in a highly desirable area. This home is in very poor condition. Do not enter the home or step onto the front porch, as both are unsafe. This property is ready for a buyer to take on a full rebuild or tear-down project. This is an opportunity to start fresh. A rare chance to create something new in a sought after Deep Creek Setting.

3482 Oakland Sang Run Rd, Oakland

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com

$735,000

5 Beds ⋅ 5 Baths

Check out this beautifully built and maintained 5 bedroom 5 bathroom lake area chalet style home. Located on the Southern side of the lake, near the headwaters of Deep Creek. The namesake stream that feeds into the nearby lake. This property offers it's new owners a tremendous amount of room for storage and entertaining and three levels of finished living space. The top floor is designed as an expansive master Suite with it's own bathroom, deep walk in closet, private balcony, and loft with a peaking view of Deep Creek lake. The main floor includes two bedrooms and two bathrooms. An open concept living room with soaring cathedral style tongue and groove ceilings, real wood flooring, stacked stone fireplace, and large open windows treated with a slight tint to improve cooling efficiency and privacy. The view looks over onto an expansive yard and almost 4 acres of private land. The bottom level has an additional living area/game room with wet bar and stacked stone fireplace, two additional bedrooms and bathrooms, storage closet, and laundry room. The home also includes a large detached heated garage with multiple car storage and additional partially finished accessory room, that could be used for storage or as a gym space. The outdoor space also features a beautifully built timber framed pavilion with bar area for outdoor entertaining. An almost brand new salt water hot tub, wraparound porch with expansive views, finished concrete walkways, and oversized parking area. Recent interior upgrades also include a new in 2023 central forced air HVAC system with A/C, freshly stained porches and extensive immaculately maintained landscaping. A recent professional appraisal was done far above list price and is available on request. Call today to schedule a showing!

1875 Pysell Crosscut Rd, Oakland

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

$1,400,000

5 Beds ⋅ 4 Baths

Custom built by the original owners and thoughtfully expanded with a recent addition, this exceptional five-bedroom, 3.5-bath home is set on 100 feet of split lakefront in desirable Penn Cove. Featuring a coveted Type A dock permit, lakeside fire pit and pavilion, and easy shoreline access, the property is designed to embrace lake living in every season. Set on a generously sized lot with abundant parking, oversized multi-car garage with interior access, usable backyard, wooded walking paths, and nearby UTV and snowmobile trails, the setting offers a rare balance of privacy and recreation. Inside, natural light fills the home, where hardwood floors, cathedral ceilings, wood-burning fireplaces, and open-concept living spaces create warmth and character. A flexible layout with multiple living areas offers room for gathering, multi-generational living, or separate guest quarters, with potential for vacation rental use. Minutes from Pawn Run, downtown Oakland, and a short drive or boat ride to Wisp Resort, restaurants, and shopping, this is a rare opportunity to own a legacy property designed for making memories for generations.

827 Penn Point Rd, Oakland

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

$875,000

3 Beds ⋅ 4 Baths

Stunning split lakefront retreat with sweeping views and Type-A dock. Experience exceptional lake life in this beautifully maintained one owner home offering breathtaking lake views and timeless craftsmanship in a serene landscaped setting. This impressive 3 bedroom 3.5 bathroom residence welcomes you through an elegant foyer with soaring cathedral ceilings and a striking oak staircase that sets the tone for the home’s warm refined character. Nearly 4,000 sq ft of thoughtfully designed living space is wrapped in a classic stone exterior that blends seamlessly into its natural surroundings. The main living area offers a cozy yet grand atmosphere with a stunning stone fireplace perfect for crisp mountain evenings while the adjoining dining area opens through sliding glass doors to a charming patio ideal for entertaining or simply enjoying the peaceful lake backdrop. The lower level is built for gathering and entertaining, featuring a spacious recreation room with a rustic stone wet bar. A generous 13 x 16 den currently used as a 4th bedroom adds flexible living space for guests or hobbies. Outdoor living shines just as brightly with a welcoming front patio offering another peaceful advantage to take in the lake views while just across the street you’ll find your private dock area complete with storage shed firepit and Type A dock providing effortless access to the water and endless opportunities for lakeside enjoyment. Blending comfort space and true lake living this exceptional property is the perfect retreat for making lasting memories. Schedule your showing today!

39 Leo Friend Rd, Oakland

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

$699,000

5 Beds ⋅ 3 Baths

Private Mountain Retreat on 8+ Acres Near Oakland Discover the peace and beauty of Garrett County living on over 8 private wooded acres filled with mountain views, abundant wildlife, and endless opportunities to enjoy the outdoors. Deer, turkey, songbirds, and other native wildlife are frequent visitors, creating a true nature lover's paradise. Conveniently located just minutes from Oakland's shops, restaurants, schools, and everyday amenities, this property offers the perfect balance of privacy and accessibility. Outdoor enthusiasts will appreciate the home's proximity to Wolf Den Run State Park, Deep Creek Lake, Potomac State Forest, Jennings Randolph Lake, and thousands of acres of public land. Enjoy hiking, fishing, boating, hunting, swimming, and over 50 miles of ORV trails, with street-legal UTV access directly from the neighborhood. This custom-built 4-5 bedroom, 3-bath home offers over 3,900 square feet of thoughtfully designed living space. Designed with flexibility in mind, the main level features two dedicated office spaces ideal for remote work, homeschooling, hobbies, guest accommodations, or future bedroom needs. The spacious eat-in kitchen showcases granite countertops, custom cabinetry, high-end appliances, a trash compactor, and generous gathering space for family and friends. Throughout the home, you'll find whole-house luxury vinyl plank flooring, oak stairs, a cozy wood-burning fireplace, a finished garage, and a walk-out basement with rough-in plumbing for a future full bathroom and exceptional expansion potential. Owners have invested extensively in quality upgrades and peace of mind, including a Generac backup generator, tankless hot water system, whole-house water filtration system, owned 1,000-gallon propane tank, upgraded fire sprinkler system, exterior security cameras, attic storage, and an additional storage building. Step outside to enjoy a covered front porch, expansive rear deck with automatic SunSetter awning, mature trees, and beautiful mountain views. Located within a laid-back HOA that allows chickens, this property offers a rare combination of acreage, privacy, modern amenities, and epic outdoor adventure. Whether you're seeking a full-time residence, a mountain getaway, or a future retirement retreat, this exceptional property delivers the best of Garrett County living. You may never want to leave after seeing this gem!

170 Cherrywood Dr, Oakland

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

$114,000

2 Beds ⋅ 1 Baths

REDUCED - Nearly an acre convenient to town - Some upgrades; newer metal roof, electrical panel box, furnace and other areas - Rear carport/patio area has easy at level access to main level - Large front porch with low maintenance entry area with wash/dryer hook-up - Good one level living layout - Sold as-is - No utilities currently active - No repairs before purchase or a lending requirement

5151 Hutton Rd, Oakland

Listing courtesy of Julian Agency Real Estate. Contact: 3017773292

$1,100,000

5 Beds ⋅ 3 Baths

Welcome to 660 Glendale Road — a luxury, mountain-chalet log home in the heart of Deep Creek Lake. This well appointed 5-bedroom, 3-bath home offers nearly 2,600 square feet of thoughtfully upgraded living space designed for lake life at its best. Enjoy lake views with western exposure on the expansive wraparound decks on main and lower levels. Many recent upgrades including roof, decks, covered porch, hot tub, retaining walls, furnace, countertops, appliances, flooring, paint, bathrooms, and much more. The open-concept main level features a spacious great room with abundant natural light, cozy fireplace, and seamless flow to the kitchen. Enjoy multiple living areas inside and out, providing plenty of room to expand and embrace time at the lake. Highlights include upgraded interior finishes throughout, private primary suite with balcony and creek views, covered deck with wood burning fireplace and a lower-level game room, four total fireplaces and only a short drive to local dining and the lake's most desirable attractions. Enjoy access to the lake at the Deep Creek State Park only a mile away or at one of the nearby marinas. No HOA! If you would like to discuss this home further or schedule a private showing, call today!

660 Glendale Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$269,000

2 Beds ⋅ 2 Baths

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

$899,900

4 Beds ⋅ 4 Baths

Luxury Estate just outside the town of Oakland. This 4-bed, 3.5 bath is situated on 9.72 acres. Offering 4,555 sq ft with vaulted ceilings, open concept living, and a rustic stacked stone fireplace. Modern gourmet kitchen with a large island and granite tops. Hardwood floors and timber frame accents throughout. Attached three-car garage. Full unfinished basement ready to add up to an additional 1300 sq ft of living space. Massive metal barn for storage or workshop. Peaceful location with rolling pasture views. Minutes to downtown Oakland, State Parks, Wisp Resort, and Deep Creek Lake. Don't miss your chance to own acreage, elegance, and function, all wrapped up in a prime location. Call today to schedule your private showing!

113 Jubb Meadows Ln, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$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

4 Beds ⋅ 2 Baths

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

$669,999

4 Beds ⋅ 4 Baths

Price improvement! This stunning, recently built 4+ bedroom, 3.5 bath home in Country Club Acres offers modern design, thoughtful upgrades, and unmatched privacy on 3.43 wooded acres perched at the top of the mountain overlooking Oakland Golf Course and multiple ponds. The bright, open-concept layout is filled with natural light and features commercial-grade LVP flooring throughout, complemented by mid-range, handpicked finishes selected by the designer/builder for a cohesive and stylish look with room for personalization. The gourmet kitchen showcases KraftMaid cabinetry, quartz countertops, and a full backsplash, while multiple ensuite bedrooms provide comfort and flexibility. Additional highlights include a fireplace, Andersen windows and sliding doors, and a fully finished basement with 10-foot ceilings providing exceptional additional living and recreation space. Enjoy outdoor living with a massive covered deck and lower patio, along with a paved driveway, oversized 2-car garage, 30-amp RV connection, tankless hot water system, water treatment system, and professionally installed sod with a fire pit. Located in the desirable Country Club Acres community with no HOA, this home offers easy access to town amenities, parks, trails, the Youghiogheny River, and Herrington Manor and Swallow Falls State Parks, delivering a perfect blend of move-in-ready comfort, scenic beauty, and long-term potential.

620 Crosby Dr, 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:

$369,000

2 Beds ⋅ 3 Baths

Log cabin on 11 private acres. Located in the gated Timbers on the Yough community. The community features shared access to the Youghiogheny River. Home features include spacious covered deck, newly installed walkway, exterior fire pit, breakfast bar, and pellet stove. Heart pine floors on main floor and stairs, reclaimed from RJ Reynolds tobacco factory built around 1900! The primary bath offers dual sinks, dual shower heads and radiant floor heat! Seller will consider owner financing for a qualified buyer.

1167 Tall Oaks Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$289,000

3 Beds ⋅ 3 Baths

Nestled in the charming Mitchell Manor community, this delightful split-level home offers a perfect blend of comfort and style. With 2,242 square feet of thoughtfully designed living space, this residence features three spacious bedrooms and two and a half bathrooms, ideal for both relaxation and entertaining. There is also a walk-in closet/dressing room to die for! Step inside to discover an inviting open floor plan, highlighted by luxury vinyl plank flooring and an abundance of natural light. The country-style kitchen boasts upgraded countertops, an island for casual dining, and a cozy breakfast area, making it the heart of the home. Enjoy evenings by the brick fireplace in the family room, creating a warm ambiance for gatherings. The exterior is equally impressive, featuring extensive hardscape and an awning that enhances outdoor living. The expansive 0.46-acre lot offers a serene rear yard with beautiful views of the mountains and surrounding trees, perfect for enjoying nature or hosting summer barbecues. Located in a suburban setting, this home is conveniently close to local parks, schools, and essential public services, fostering a strong sense of community. Residents appreciate the peaceful atmosphere while being just a short drive from shopping and dining options. With an attached garage and ample driveway space, parking is a breeze. This property is not just a house; it's a place to create lasting memories. Experience the warmth and charm of Mitchell Manor, where comfort meets community.

163 Mitchell Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$275,900

4 Beds ⋅ 2 Baths

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:

$912,000

3 Beds ⋅ 3 Baths

Experience mountain living at its finest in this breathtaking mountaintop home overlooking Deep Creek Lake. With sweeping views from almost every room, your hardest decision may be where to sit to enjoy them. Offering three levels of living space, hardwood floors ( which were recently refinished), and some new appliances. The multiple decks are ideal to enjoy family and friends while taking in the beauty around you. The location is another plus, just minutes to the community club house where you can enjoy the lake, and minutes to Wisp Ski & Golf Resort, restaurants, coffee shops, cinemas, and grocery stores. Class A lake access. Call today to preview!

164 Grandview Dr, Oakland

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

$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

$769,900

4 Beds ⋅ 4 Baths

Panoramic mountain and lake views set the tone at this lake access home in Paradise Ridge, one of Deep Creek’s most sought-after communities! Perched at the top of the hill on 1.29 acres, this 4-bedroom, 3 full and 1 half bath retreat offers 3,780 finished square feet across three levels. Abundant glass frames the surrounding ridgelines with views of Deep Creek Lake from every room in the house! Two wood-burning fireplaces anchor the main living areas, while the open floor plan makes entertaining a breeze. The upper-level game room features a pool table and a balcony, adding extra gathering space. Tons of outdoor living, including an expansive deck, hot tub patio, and outdoor fire pit. Recent facelift on the exterior with a fresh coat of paint. An established vacation rental, “Paradise View,” is being sold turnkey/fully furnished and ready to go. Minutes from one of the nicest community lake accesses at Deep Creek Lake. If you’re looking for a home that sits just off the beaten path, but still provides easy access to all four seasons of Garrett County… this one needs to be on the list. Call today for details!

467 Paradise Ridge Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$64,900

**Investor Special with Mountain & Water Views** Opportunity is knocking at 74 Parks Road in Oakland, Maryland! This 3-bedroom, 1-bath one story is perfectly positioned just steps from the West Virginia line and surrounded by some of the most sought-after recreation in the region. Enjoy peaceful views of Snowy Creek right from the front yard and take advantage of being just minutes from Deep Creek Lake, Alpine Lake Resort, and Herrington Manor State Park — offering year-round activities including boating, fishing, hiking, skiing, and more. Whether you're looking to create a full-time residence, mountain getaway, or short-term rental investment, the location alone makes this property standout. The home is ready for renovation, offering a blank canvas for investors or buyers eager to design a space tailored to their vision. With a desirable ranch-style layout and strong potential, this property presents a chance to create something truly special in a sought-after area. If you've been searching for a project property in a high-demand recreational area with creek views and proximity to multiple lakes and state parks — this is your chance to build equity in one of Western Maryland’s most scenic settings. Bring your builder or contractor and your creativity — the possibilities are endless!

74 Parks Rd, Oakland

Listing courtesy of Real Broker, LLC. Contact: 8504500442

$1,074,900

4 Beds ⋅ 6 Baths

Panoramic Lake views in the Bray Run community, just minutes from Deep Creek Lake, state parks, and more! Built in 2025, this 4-bedroom, 4 full bath, 2 half bath log style chalet sits on 0.59 acres of peaceful, quiet serenity. Cathedral and beamed ceilings rise above an open layout filled with abundant natural light. Two stacked-stone fireplaces anchor the main living area and the lower-level family room. Granite counters, stainless appliances, and a custom island define the kitchen. A loft overlooks the main level, adding flexible living space. Outside, a deck and stamped-concrete patio lead to a covered pavilion with a wood-burning fireplace for year-round use. Central A/C, forced air heat, well water, public sewer, and a metal roof complete the package. If you’re looking for a new home that’s just off the beaten path, yet still offers easy access to everything Deep Creek Lake has to offer—this one needs to be on the list… Call today for details!

52 Dam View Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$629,000

Brand new roof July 2026! 3/4BR 3BA chalet with LAKE VIEWS! 2300sf vacation home fronting on a mountain stream, overlooking Deep Creek Lake! Enjoy an eat-in kitchen, exposed beams and a loft area that the current owners use as a 4th BR with bathroom. NO HOA! Conveys fully furnished. Features include central AC, exposed beams, updated flooring, gas fireplace on main level, lower level rec room with pool table and wrap-around deck with hot tub. Central location near 219 bridge, close to Wisp & local restaurants, entertainment and shopping.

231 Santa Fe Trl, Oakland

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

$265,000

4 Beds ⋅ 2 Baths

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:

$329,999

Very motivated sellers!!!Escape to Your Profitable Mountain Sanctuary: The Yough Mountain Cabin Unveiling the Ultimate Turnkey Retreat & High-Performing Investment Nestled in the breathtaking heart of the exclusive Yough Mountain Resort, this stunning 3-bedroom cabin offers the perfect harmony of rustic soul and modern investment savvy. Whether you are looking for a private family getaway or a powerful addition to your portfolio, this property delivers on every level. A Proven Income Generator This isn't just a home; it’s a verified revenue engine. Currently managed by a Premier Superhost on top short-term rental platforms, this cabin is a guest favorite with an annual revenue projection exceeding $26,000. Experience the pride of ownership while the property pays for itself. Rustic Elegance & Modern Comfort Step inside to a world of warm wood floors and soaring vaulted wood-planked ceilings. The living area is anchored by a magnificent wood-burning fireplace with a custom stone surround, perfect for cozy mountain evenings. The heart of the home features a beautiful kitchen with rich wood cabinetry that blends seamlessly with a chic mix of wood and drywall finishes. Adventure Ready Wired for Sound: Create the perfect atmosphere with an integrated sound system that carries your favorite playlists both inside the cabin and out onto the expansive wrap-around covered porch. On-Site Amenities: You are less than a quarter-mile from the heartbeat of the resort—the community clubhouse, pavilion, and tot lot are just a short stroll away. Trail Access: Yough Mountain Resort is a playground for enthusiasts, offering miles of exhilarating 4-wheeler and hiking trails right at your doorstep. Minutes from World-Class Attractions Beyond the serenity of the resort, you are perfectly positioned to enjoy the best of Western Maryland’s four-season recreation: Wisp Resort: Just a short drive away for premier skiing, snowboarding, championship golf, and the thrilling mountain coaster. Deep Creek Lake: Access endless summer fun with boating, paddleboarding, and lakeside dining. Swallow Falls State Park: Home to Maryland's highest cascading waterfall and miles of pristine hiking trails. Youghiogheny River: Famous for its world-class whitewater rafting and tranquil fishing spots. Your Versatile Haven From its meticulous maintenance to its unbeatable location, this cabin is ideal as a full-time residence or the ultimate vacation "get-a-way." Don't just dream of the mountain life—buy the dream and the revenue that comes with it. Contact us today for a private showing!

931 Black Oak Dr, Oakland

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

$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:

$6,499,900

8 Beds ⋅ 9 Baths

Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with a sprawling island, Wolf range, and access to a four-season room that opens fully to the outdoors through custom bi-fold doors. The main-level primary suite spans nearly 900 sq ft with a private balcony, soaking tub, his-and-her vanities, and a massive walk-in closet. Enjoy five fireplaces, an indoor pool with fountains and a full bath, and three levels of outdoor living, including an outdoor kitchen, built-in hot tub with gazebo, outdoor shower, and deck drainage system to keep lower levels dry. Entertain with ease in the rec room with an industrial-style bar, climate-controlled wine cellar, and fully equipped gym. Three attached garages connect to a locker-style mudroom, with a lower-level garage ideal for a side-by-side or lake toys. Radiant heat, a whole-house generator, and three dock slips make this property as functional as it is flawless. A rare opportunity to own a true statement home in one of Deep Creek Lake’s most prestigious communities. Call today for your private tour!

47 Holy Cross, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$164,000

Remodeled Rancher Near the North Branch Potomac River This charming 3-bedroom, 1-bath rancher has been completely remodeled, with all new appliances. Located within walking distance of the scenic North Branch of the Potomac River, the home offers both convenience and natural beauty at your doorstep. A recently enclosed front porch with a wood stove provides extra warmth and a welcoming spot to relax year-round. The property also includes a spacious 33’ x 18’ detached garage—perfect for vehicles, storage, or a workshop—as well as a wood shed for added utility. Call now for your private tour!

63 Wallman Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$385,000

3 Beds ⋅ 3 Baths

Surrounded by 100+ Acres of Nature Conservancy conservation lands, on a 1.68-acre scenic home site, this 3-bedroom, 2.5-bath home combines natural charm with modern comfort. The native stone exterior and peaceful setting set the tone for this inviting residence. The wrap around deck is perfect for quiet time with beautiful views. Inside, the main level features a spacious primary bedroom suite, heated breezeway/mudroom and attached garage. Large Country kitchen & combined Dining area. The upper level offers 2 good size BR's, full bath and a den or family room. The full unfinished basement is heated and ready for additional living area. Roof system has been recently replaced and the heating is efficient propane Hot Water Baseboard. Separate Native Stone covered Detached garage. Call for your private tour. Estate Sale "Sold As Is"

5024 Cranesville Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$1,650,000

4 Beds ⋅ 6 Baths

Unique luxury home on 23 acres with 360 degree views of Pleasant Valley. 5,100 + SQ. FT. 4 ensuite bedrooms, 2 additional powder rooms, formal living room/ballroom, informal living room, sunroom, den, pantry and large dine in kitchen. 4 fireplaces. full basement, 3 car attached garage. Whole home generator. Everything in this home is first rate. A must see for the discerning buyer

3898 3898 Underwood Rd, Oakland

Listing courtesy of Custer Realty & Auction. Contact: 3013344876

$760,000

4 Beds ⋅ 5 Baths

Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just minutes from Deep Creek Lake and Oakland. This 4-bedroom, 4.5-bath home has been carefully updated to balance comfort, practicality, and modern style. The main level features hardwood floors, radiant heat for added comfort, and open gathering spaces with quiet nooks for reading or hobbies. Upstairs, two primary bedrooms with private baths provide flexibility for family or guests. The full apartment-style basement includes its own kitchen, laundry, and heated floors, offering an inviting space for extended stays or independent living. Outdoors, a stamped concrete driveway leads to an oversized two-car garage, with additional garages and sheds for storage or projects. A fenced in-ground pool, hot tub, and wood decking create a welcoming space for entertaining and relaxation. With thoughtful upgrades throughout, extensive amenities, and close proximity to both town and lake, this property offers the best of convenience and privacy in one setting.

1909 Pysell Crosscut Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$299,000

Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat offers privacy, comfort, and plenty of space to unwind. Step inside to find a warm and inviting main level highlighted by a stone fireplace, cozy dining area, and galley-style kitchen. Relax on the screened-in porch complete with a hot tub under roof, perfect for year-round enjoyment. The finished basement is an entertainer’s dream, featuring a pool table, wood stove, mudroom, half bath, and a bedroom with its own attached full bath—ideal for guests. Additional features include an attached 1-car garage, carport beneath the covered deck, and a layout designed for both everyday living and mountain getaways. Lovingly maintained and in excellent condition, this home combines rustic charm with modern comfort in an incredible setting. Located within the gated recreation community of Yough Mountain Resort, you'll have access to over 50 miles of ATV, snowmobile, and hiking trails, as well as river access, fishing, and hunting. For those seeking even more adventure, Deep Creek Lake, the town of Oakland, Swallow Falls, and Herrington Manor State Park are just minutes away, offering endless possibilities. Call today!

961 Cedar Ln, Oakland

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

$425,000

3 Beds ⋅ 4 Baths

Here's your chance to purchase a cute Chalet with just about 7 acres. .This home and acreage is right next to the Common Grounds and gives you immediate river access.

104 Pine Top Trl, Oakland

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

$499,900

Perched above the treetops with panoramic lake views, this three-level retreat blends comfort with clean, considered upgrades. Vaulted ceilings and a spacious loft crown 2,235 square feet of living space, wrapped in new flooring with fresh paint inside and out. The kitchen, smartly updated with new countertops, connects to open dining and living anchored by a wood stove. A detached garage sits off the drive; while the private deck draws the eye to the water. An established rental, “Views and Brews” is being sold fully furnished and ready to go. Just minutes to marinas, Wisp Resort, and the lake’s best bites. Call today for details!

126 Leo Friend Rd, 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

Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-sided home offers the perfect blend of rustic charm and modern comfort—all just 10 minutes from downtown Oakland. This well-maintained home features 3 spacious bedrooms and 2 full bathrooms, including a main floor master suite for added convenience. Inside, you’ll find brand-new luxury vinyl plank (LVP) flooring that adds style and durability throughout the living spaces. The large, inviting kitchen provides plenty of room for cooking, entertaining, and gathering with loved ones. Recent upgrades include a brand-new metal roof, offering peace of mind and long-lasting durability. Outside, the property showcases a beautiful mix of mature woods and open fields—ideal for nature lovers, outdoor enthusiasts, or those simply seeking privacy and space to roam. Whether you're looking for a peaceful weekend retreat or a full-time residence with easy access to town, this unique property delivers the best of both worlds.

1737 King Wildesen Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$545,000