Oakland, MD Single Family Homes for Sale

Location, location, location! Enjoy easy living in this one-level raised rancher featuring 3 bedrooms and 1.5 baths, with all bedrooms conveniently located on the main level. Beautiful hardwood floors add warmth, while the covered front porch and side covered deck offer inviting spaces to relax and enjoy the peaceful surroundings. The fenced-in backyard provides plenty of outdoor space for pets, play, or entertaining. The full basement is ready for your finishing touches and offers additional potential, while the attached one-car lower-level garage provides convenient parking or extra storage. Recent updates include a new roof and a full WaterGuard system installed along the interior basement foundation. Located in a peaceful neighborhood close to schools, the hospital, and shopping, this home offers comfort, convenience, and plenty of opportunity to make it your own. Call today to schedule your showing!

139 S Oakhall Dr, Oakland

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

$1,100,000

Vintage 3BR Lakefront Dome Home with Private Type "A" Dock! & no HOA . Own a piece of Deep Creek charm with this unique 3-bedroom, 2-bath vintage lakefront home w/ 2,034 finished square ft of living area, featuring 100 feet of lake frontage, beautiful sandy shoreline, and a private dock. The eye-catching dome-style architecture sets this property apart, offering a cozy and distinctive retreat. Located just minutes from Wisp Ski & Golf Resort and the ASCI Whitewater Course, it’s perfectly positioned for year-round adventure. Currently an established rental, this home offers both personal enjoyment and income potential. Don’t miss your chance to own a truly special lakefront getaway! Schedule your showing today

2849 Shingle Camp Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$74,990

3 Beds ⋅ 1 Baths

INVESTOR SPECIAL!! GREAT FOR FIX AND FLIP OR HOLD! Property is sold completely as-is with all contents. Buyer to pay all closing,100% TT&Rs. CASH or Hard money only.

102 Roanoke Ave, Oakland

Listing courtesy of Samson Properties. Contact: 7033788810

$449,000

Fall in love with the peaceful setting of this inviting log home nestled in the sought after Pergin Farm community at Deep Creek Lake. Surrounded by trees and tucked away in a quiet setting, this 3 bedroom, 1.5 bath home offers the warmth and character of a true mountain retreat with a layout that feels both comfortable and connected. Step inside through the welcoming mudroom, where the home naturally opens into the kitchen and dining area, creating an easy gathering space that flows into the inviting living room. A bedroom and full bath complete the main level, while two additional bedrooms upstairs provide a private retreat for family or guests. The lower level expands the living space with a spacious family room, bar, half bath, foosball, and shuffleboard, giving everyone a place to relax and have fun after a day at the lake. Outside, enjoy the full length covered front porch, wooded surroundings, patio with hot tub and grill, and firepit made for evenings under the stars. An oversized two car garage with storage above and a detached garage provide plenty of space for vehicles, lake gear, and storage. Whether you are looking for a year round home, a private mountain escape, or an investment opportunity, this property offers the flexibility to make it your own. Currently operating as a vacation rental, it provides the added opportunity for rental income while you enjoy all that Deep Creek Lake has to offer. Call today!

482 Pergin Farm Rd, Oakland

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

$920,000

Welcome to this charming 3Br, 2BA home in the quiet and serene Penn Point area of Deep Creek Lake. A Type A dock slip is included and is just an easy walk or golf-cart ride from the property, making lake days more convenient and enjoyable. Inside you'll find an inviting open concept kitchen, dining, and living area that flows seamlessly onto a spacious outdoor deck. Enjoy morning coffee, outdoor dining, grilling and entertaining while taking in the peaceful surroundings. The home sits on just under 1/2 acre, offering plenty of space to enjoy and potential for future expanding. The large, detached garage provides exceptional storage for your boat, jet skis, lake toys, and all your recreational gear. Whether you're looking for a year-round home or a Deep Creek getaway, this property offers the perfect combination of comfort, outdoor enjoyment, and access to the lake. Deep Creek Lake is a four-season destination with boating, golfing, hiking, skiing, dining, and activities for all ages. Conveniently located on Upper Penn Point Road, you'll be close to everything Deep Creek has to offer while still enjoying the peaceful setting. Come see all this property has to offer!

184 Upper Penn Point Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$399,900

Welcome to this beautifully crafted new construction home, where modern comfort meets thoughtful design in an unbeatable location. From the moment you step inside, you'll appreciate the spacious layout, quality finishes, cathedral ceilings, and abundance of natural light throughout. The heart of the home is the spacious kitchen, featuring crisp white cabinetry, warm natural wood butcher-block countertops, a double sink, stainless steel appliances, a large center island with ample seating, and a generous sized walk-in pantry offering exceptional storage. The main level includes 3 bedrooms and 2 full bathrooms, highlighted by a private primary suite with a walk-in closet and en-suite bathroom with a tiled walk-in shower, along with two additional bedrooms, a full hall bathroom, and a convenient laundry room. Step outside onto the exterior deck overlooking the yard, perfect for relaxing or entertaining, while the attached one-car garage provides added convenience. The full unfinished basement offers endless possibilities for future living space, a recreation room, home gym, office, or whatever best suits your needs. Located just minutes from newly built Broadford Elementary School, Broadford Park, Downtown Oakland, and Garrett Regional Hospital, and a short drive to Deep Creek Lake, this home offers the perfect blend of modern comfort, convenience, and accessibility. This stunning new build is a must see!

1407 Broadford Rd, Oakland

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

$899,900

5 Beds ⋅ 6 Baths

Welcome to Happy Hoursss... Hideaway, a stunning Deep Creek Lake retreat where breathtaking views, upscale amenities, and spacious indoor-outdoor living create the perfect getaway. With 5 bedrooms and 6 full bathrooms, this beautifully appointed home comfortably accommodates family and friends while offering plenty of room to relax and entertain. The main level features an inviting open-concept kitchen, dining, and living area with stainless steel appliances, a large center island, fireplace, abundant natural light, and beautiful lake views. A main-level primary suite and additional full bath add convenience. Upstairs, a second luxurious primary suite offers a walk-in closet and spa-like bath with a jetted tub and separate shower. The lower level is designed for fun and relaxation, with three bedrooms and three full baths, a second living area, fireplace, wet bar, and access to the deck and hot tub. The entertainment continues with a plenty of space to gather. Outside, enjoy two decks, a hot tub, fire pit, grill, room for games and entertainment, expansive yard space, ample parking, and a storage building for your outdoor gear. Whether you’re soaking in the hot tub under the stars, gathering around the fire, or enjoying a quiet morning, Happy Hoursss...Hideaway delivers an unforgettable Deep Creek Lake experience in every season.

395 Woodlands Hill Ln, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$444,700

Welcome to *HIDDEN TREASURES*, a beautifully appointed 4-bedroom, 3½-bath home offering the perfect Deep Creek Lake getaway! This established rental property is ideally located close to the lake’s many amenities, making it an excellent opportunity for both personal enjoyment and investment potential. Relax and unwind in the private hot tub after a day of boating, hiking, skiing, or exploring all that Deep Creek has to offer. Enjoy the outdoors from the spacious covered front and back porches—perfect for morning coffee, evening gatherings, and taking in the peaceful surroundings. With comfortable living spaces, ample bedrooms and baths, and a desirable location near area attractions, Hidden Treasures is ready to continue as a sought-after vacation rental or become your own private mountain-lake retreat. A wonderful opportunity to own a piece of the Deep Creek Lake lifestyle! Call today to set up a viewing of this lake area property!

333 Sloan Tract Rd, Oakland

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

$1,199,000

4 Beds ⋅ 3 Baths

Beautiful lakefront home offering 89' of lakefront and a private dock. This home has been remodeled and is very warm and inviting from the moment you enter. Boasting a great island featuring granite countertops, and plenty of seating for family and friends. The lakefront views are unobstructed year round, and can be enjoyed from most any room. The outside space is just as pleasing with a wrap-around Trex deck, stone patio with a hot tub, and a firepit. If all of this isn't enough, take a few steps down to the lakefront and enjoy the type A dock. The central location is also hard to beat, just minutes to coffee, ice cream, Wisp Ski Resort, grocery stores and restaurants. Established rental "Moments & Memories". Call today to preview!

20698 Garrett Hwy, Oakland

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

$689,000

4 Beds ⋅ 3 Baths

Experience the best of Deep Creek Lake living at this beautifully renovated mountain retreat in the peaceful and desirable Paradise Ridge lake access community. Thoughtfully updated from top to bottom, this home blends modern comfort with the serenity of nature, creating the perfect full-time residence, vacation getaway, or potential vacation rental investment property. One of the property's standout features is its close proximity to one of the most desirable lake access areas on Deep Creek Lake. Enjoy convenient access to the water, offering a more private and relaxing lake experience without the crowds. Featuring a level shoreline, picnic pavilion, ample parking, and easy entry for paddle boards, kayaks, canoes, swimming, and fishing in the quiet no wake zone cove. Nestled in a quiet, wooded setting, you'll appreciate the peaceful surroundings while remaining just minutes from local restaurants, shopping, Wisp Resort, state parks, golf, and all the year-round recreation Deep Creek Lake has to offer. Whether you're spending the day on the lake, enjoying nearby dining, or relaxing in the tranquil setting, 180 Paradise Ridge Road offers the perfect combination of spacious living space, convenience, comfort, and mountain charm. Chill out on the large back deck and patio area or around the campfire. Don't miss this opportunity to own your own slice of Deep Creek paradise. Get your tour scheduled now!

180 Paradise Ridge Rd, Oakland

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

$375,000

2 Beds ⋅ 2 Baths

Enjoy all the seasons in this beautiful Cape Cod home nestled on a 1-acre private wooded lot close to Oakland and all the attractions Deep Creek Lake has to offer. Whether you are seeking a year-round permanent residence or a private seasonal getaway for summer and winter fun, this property delivers a wonderful setting with an ideal balance of privacy and convenience. The open floor plan allows seamless flow throughout the main living areas. The vaulted ceiling in the living room maximize light and space. Enjoy the main floor primary suite with private access to a full bathroom, complete with a huge bath and a spacious walk-in closet. The upper loft features an open area that overlooks the living room, it can be used as a recreation room or easily function as a third bedroom or extra sleeping space. The one car garage with attached carport affords plenty of space to store your vehicle alongside your seasonal outdoor gear and toys.

18948 Garrett Hwy, Oakland

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

$3,950,000

8 Beds ⋅ 10 Baths

Experience exceptional lakefront living in this spectacular eight-bedroom estate designed for unforgettable gatherings and year-round enjoyment. Perfectly positioned on an oversized lakefront lot with 116’ LF, this remarkable home offers easy access to the water via a walking path, and the abundance of windows fill the interior with natural light. At the heart of the home is a magnificent great room with soaring ceilings, creating an impressive space for entertaining family and friends. The gourmet kitchen is a chef's dream, featuring premium finishes, generous prep space, and abundant cabinetry, making it as functional as it is beautiful. Boasting an indoor sparkling pool and sauna right off the lower-level family room, along with a full kitchen and a playroom. Then step outside to your private lakeside retreat, complete with two relaxing hot tubs, a fire pit area, a sports court in the front, and spacious outdoor living areas ideal for dining, entertaining, or simply soaking in the peaceful surroundings. With eight spacious en-suite bedrooms, there is ample room for guests, making this an exceptional primary residence, vacation home, or luxury rental opportunity “The Haven”. Offering the perfect blend of elegance, comfort, and resort-style amenities, this extraordinary waterfront property is a rare opportunity to own the ultimate lakefront lifestyle.

1131 Lake Shore Dr, Oakland

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

$460,000

5 Beds ⋅ 2 Baths

Escape to the tranquility of country living in this spacious 5-bedroom, 2-bath home nestled on over 2 acres and conveniently located just minutes from the recreational opportunities of Deep Creek Lake and the charming town of Oakland, The property offers the perfect combination of peaceful country living and easy access to shopping, dining, and year-round activities. The kitchen has been thoughtfully updated with new stainless-steel appliances, including a microwave, refrigerator, gas range with oven, and gas wall oven. You'll also appreciate the new stainless-steel farmhouse sink with an updated faucet, and a new InSinkErator garbage disposal. The main floor also offers the convenience of a bedroom, full bathroom, and laundry area complete with a new washer and dryer, making one-level living a possibility. Upstairs, you'll find four generously sized bedrooms and an additional full bathroom, offering plenty of space for family and guests. Additional interior improvements include a new 50-gallon hot water heater, a new attic fan with humidifier, a new well water filtration system, and a newly installed ADT security system for added peace of mind. Recent exterior updates include new outdoor lighting and a new roof including all new sheathing, underlayment (roof wrap), and shingles, providing years of worry-free ownership. If you've been searching for privacy, space, and the beauty of rural living, this property is a must-see!

5154 Maryland Hwy, Oakland

Listing courtesy of Coldwell Banker Home Town Realty. Contact: 125014.lead@leads.leadrouter.com

$799,900

Experience modern mountain living in this brand-new 2026 construction. This beautifully designed 4-bedroom, 4-bath home offers two spacious levels, quality finishes, and plenty of room for family and guests. Open layout with modern kitchen, island bar, and stone fireplace. Stamped concrete patio with covered fireplace and outdoor kitchen. Over half an acre of private wooded mountain-top space complete with fire pit and level usable yard. Andersen Windows and LVP flooring throughout. Ideally situated just minutes from Wisp Resort, Deep Creek Lake, state parks, restaurants, shopping, and year-round recreational attractions, this home provides the perfect blend of comfort, convenience, and adventure. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this new construction is ready to make lasting memories.

15 Byran Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$174,900

2 Beds ⋅ 1 Baths

Welcome to this charming 2 bedroom, 1 bath home in the heart of Oakland, offering endless potential and plenty of character. Step inside to an inviting open floor plan that creates a bright, spacious feel and allows for a comfortable flow between the living and kitchen areas. The large covered front porch provides the perfect spot to enjoy your morning coffee, relax after a long day, or take in the peaceful surroundings. Whether you're looking for your first home, an investment property, or a property to personalize and make your own, this home offers incredible potential. Located in a highly desirable school district, you'll enjoy the convenience of being just minutes from shopping, dining, recreation, and all the amenities Oakland has to offer. With its charming details, functional layout, and unbeatable location, this property is ready for your vision and personal touch. Don't let this opportunity pass you by. Schedule your showing today!

206 W Liberty St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$169,000

3 Beds ⋅ 1 Baths

Enjoy the charm of country living with the convenience of being in downtown Crellin! Situated on nearly an acre, this inviting 3-bedroom, 1-bath home offers a bright, open layout filled with natural light. The main level features a spacious bedroom surrounded by windows, creating a warm and welcoming retreat. Upstairs, you'll find two additional bedrooms that can easily accommodate family, guests, or be transformed into a home office, playroom, or hobby space. Storage is abundant with an interior pantry, storage room, and dedicated workspace, plus an outdoor shed and detached garage for all your tools, equipment, and recreational gear. All staged items included! All furniture conveys except the white shelf in the pantry. The yard is fenced in, beautifully manicured and has a fire pit. An added bonus is the additional lot included with the property at 97 Crellin Street. This parcel already has public water and sewer hookups and was formerly the site of the Crellin Community Center, offering exciting possibilities for future use, expansion, or investment (subject to local zoning and approvals). Whether you're looking for your first home, a peaceful retreat, or a property with room to grow, this unique offering combines comfort, space, and potential in a convenient location. This one won't last! Reach out for a showing today!

40 Sunshine, Oakland

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

$365,000

PRIME INVESTMENT OPPURTUNITY! Recently renovated (including plumbing and electric) in 2025, this triplex is a rare opportunity in the heart of downtown Oakland, MD. With three separate units, you'll have the potential for three streams of rental income from one property. Buyer could live in one unit and rent the other units out to help offset mortgage costs! Whether you're a seasoned investor or just getting started, this turnkey property offers updated finishes, strong income potential, and a prime location just steps from shops, restaurants, and everything downtown has to offer. Top floor is 1-bedroom and 1-bathroom. Middle floor is 2-bedroom and 1-bathroom. Bottom floor is 2-bedroom, 1-bathroom and has a laundry hookup. Contact me today with any questions or to schedule a time to tour the property!

615 E Oak St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$799,000

LAKEFRONT 4BR, 3.5BA log home with over 3300sf and 4.35 acres of privacy! Lovingly maintained property with gorgeous views of the 10 acre lake from almost every room in the house! Peaceful surroundings with towering mature trees and just enough yard space in a very laid back, rural setting near Herrington Manor and Swallow Falls state parks. If that weren't impressive enough, Meadow Lake Estates community is adjacent to 598 acres of DNR / state land fronting on the Youghiogheny River. Set up for one level living - bedroom suite and laundry room on first floor. Features include whole-house generator, wood-burning fireplace, a recently finished basement adding a game room and a fourth bedroom, front and rear decks (trex on back deck), covered porches, fire-pit, wrap-around driveway and a spacious loft that serves as a third living room. Must see to appreciate the solitude of this fantastic home! Furnishings negotiable. Short term rentals are not permitted in this community.

325 Markwood Dr, Oakland

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

$1,425,000

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:

$775,000

5 Beds ⋅ 5 Baths

One-of-a-kind Youghiogheny riverfront estate offering 224 feet of water frontage . Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to ceiling fireplace, log accent walls and exposed beams. Features include multiple fireplaces (wood & gas), Andersen doors & windows, trex decking, hardwood floors, metal roof, custom cabinets in kitchen & bedroom suites, eat-in kitchen, and sold furnished! Enjoy a picturesque setting in a riverfront setting with NO HOA restraints for this home. Seller also offering an adjacent unbuilt riverfront lot (#9) for $175,000 MLS #MDGA2012380

251 Robinwood Dr, Oakland

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

$325,000

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

Listing courtesy of Lake Homes Realty, LLC. Contact: 8665253466

$899,000

6 Beds ⋅ 5 Baths

Luxury Living Meets Timeless Country Charm! Perfectly positioned on 10.33 picturesque acres between Oakland and Deep Creek Lake, this exceptional 6-bedroom, 4.5-bath home offers the ideal blend of refined comfort, modern updates, and peaceful privacy. Step inside to discover an inviting open floor plan highlighted by soaring wood ceilings, a dramatic floor-to-ceiling stone fireplace, and expansive windows that fill the home with natural light while showcasing the serene surroundings. The beautifully updated kitchen is designed for gathering, featuring granite countertops, abundant cabinetry, stainless steel appliances, and a spacious island that flows seamlessly into the dining and living areas. With six generously sized bedrooms and four-and-a-half baths, there's room for everyone to relax in comfort. Thoughtful upgrades throughout the home provide a fresh, modern feel while maintaining the warmth and character of this impressive property. Outside, your own private retreat awaits. Spend summer days enjoying the heated in-ground swimming pool, entertain on the expansive rear deck, or simply unwind while taking in the views of the park-like backyard. The sprawling acreage offers plenty of room for recreation, gardening, or simply enjoying the beauty of nature. Completing the property is a 3-car attached garage, offering ample space for vehicles, outdoor gear, and storage. Conveniently located just minutes from Deep Creek Lake, Wisp Resort, restaurants, shopping, and Oakland's historic downtown, this remarkable home delivers the perfect balance of luxury, convenience, and country living. Whether you're searching for a full-time residence or a private retreat near Maryland's premier four-season destination, this extraordinary property is one you won't want to miss. *$5,000 buyer credit for carpeting with accepted offer*

17240 Garrett Hwy, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$745,000

Welcome to this stunning 5-bedroom, 3-bath home, completed in 2023 and designed for modern mountain living. Featuring two private ensuite bedrooms, spacious living areas, and a fresh, contemporary design, this home is ready for you to enjoy from day one. This home features a stylish modern kitchen with an open layout that is perfect for entertainment. In the winter months, cozy up by the wood burning fireplace in the living room. Step outside and enjoy plenty of deck space for entertaining, grilling, or simply relaxing with your morning coffee. Gather around the fire pit under the stars after a day on the lake. Located just minutes from Deep Creek Lake's top attractions including boating, dining, shopping, Deep Creek Lake State Park and Wisp Resort—this home is perfectly positioned for every season of adventure. No HOA! This property is a current Airbnb rental "Paradise Getaway" with proven rental income. Contact me today for a private showing!

943 Paradise Hts, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$719,999

Experience the best of Deep Creek Lake living in this thoughtfully designed 4 bedroom, 3.5 bath home located in the highly desirable Mountainside community. Combining quality craftsmanship with inviting living spaces, the well planned floor plan maximizes both comfort and functionality. The finished basement provides additional living space perfect for entertaining family and friends. Situated on over an acre, the expansive outdoor living area features a wraparound porch and private hot tub, creating the ideal setting for relaxing, gathering, or enjoying the beauty of every season. With a history of strong vacation rental performance, this property offers an outstanding opportunity as an investment, second home, or full time residence. Enjoy community amenities including tennis courts, a basketball court, lake access, a clubhouse, and the opportunity to participate in an annual dock slip lottery. Conveniently located just minutes from Deep Creek Lake, Wisp Resort, restaurants, and shopping, this home provides easy access to year round recreation while offering the peace and privacy of mountain living. Whether you’re seeking a personal retreat, full time residence, or proven investment property, this Mountainside gem is ready to be enjoyed.

941 Mountainview Dr, 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:

$1,095,000

2 Beds ⋅ 3 Baths

A Rare Fine Indeed! The private, end of the road farm is located in the much-desired Pleasant Valley area of southern Garrett County, MD. Built in 1933 and remodeled in 2020, this farmhouse is a must see. The inviting living area is complemented by a wood burning stove, while a LP gas furnace provides hot water radiant heat throughout the home. The kitchen features concrete countertops and is highlighted by an antique two-bowl porcelain sink. The two bedrooms have walk-in closets. This 64 +/- acre property has approximately 40 +/- acres of tillable land and there is an additional 9.44 +/- acres that is subject to a CREP/Conservation Easement where 4100 trees were planted (9 Different species). Whether you're seeking a full-time residence or a vacation getaway, this property captures the best of both worlds. Great area to ride your ATV's and if you're a hunter has whitetails on the property. The property features a 40-foot x 76-foot barn with approximately 5900 Sq. Ft of area inside. Plenty of room for hay, grains or storage for your equipment. Come and enjoy the COUNTRY!

826 G Swauger Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$384,500

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

$3,249,000

4 Beds ⋅ 5 Baths

One of Garrett County's most unique and breathtaking mountain estates, this completely custom masterpiece was designed and built with exceptional craftsmanship and attention to detail. The 6000 +/- sq ft custom newly built home is located in the beautiful mountains of Garrett County, Maryland and offers the new owner one-of-a-kind unobstructed panoramic views, serenity, privacy and endless possibilities. Bordering the Potomac State Forest, up to 64 +/- acres ( 2 parcels, 1 of 50 acres and the other 13.74 acres)of pristine land, offering unmatched privacy, mature woodlands, spacious fields with a stocked pond and natural streams on the property, where the new owner can relax and recharge from everyday life. The property has also been perc tested for 1 additional residence. Outdoor amenities include three outbuildings. There are two finished outbuildings including a quaint accessory dwelling unit featuring a small kitchenette, living space, full bathroom and private deck. The second finished outbuilding is set up as a bunk house with a covered porch, barn doors and a custom stamped concrete patio with fire pit. You can use the unfinished outbuilding to store your ATV or UTV. The hot tub area offers stunning canyon views high above Laurel Run. This beautiful home has antique oversized brick, Everlast horizontal lap siding, architectural shingles, standing seam metal accents, black Anderson doors and Anderson windows, black half round gutters and downspouts, large exterior decks with custom railing and stamped concrete patios. This well constructed home features 2x10 exterior walls with spray foam insulation for low heating and cooling costs, radiant in floor heat along with forced air heat and central air conditioning. The interior walls are covered in native field stone from the property, shiplap siding, drywall, and barnboard. Added features include handcrafted wormy oak doors and wormy oak flooring and tile flooring. The interior of this 4 bedroom/5 bath features a luxurious main-level primary suite with walk-in shower, freestanding bathtub and walk-in closet, 1 spare bedroom/office on the main level, 1 main level full bathroom with walk-in shower, main level laundry room with utility sink, 2 upper level en-suites with walk-in shower and freestanding bathtubs, the lower level features a full bathroom with walk-in shower, there are 2 stone fireplaces, gourmet kitchen with extra-large island, walk-in pantry with custom cabinetry and prep sink, dining room, 3 family rooms and three finished utility rooms. The expansive lower-level family room opens to not one, but two attached finished garages with radiant floor heating for ultimate convenience. In the interior, you will also find large timbers, metal ceilings and exposed spiral ductwork. This mountain ranch estate is an outdoor enthusiast’s year-round dream property that offers unforgettable summer gatherings, spectacular fall vista views, a winter wonderland and breathtaking springtime hikes along cascading snowmelt waterfalls. In addition to opportunities for agriculture and farming, the property includes various trails suitable for nature walks, horseback riding, hiking, biking, ATV/UTV use, cross-country skiing, and snowmobiling. This large tract of land offers a natural habitat for wildlife that you can admire up close. The property also offers excellent birdwatching, hunting, fishing and nearby ORV trails. Located minutes from Deep Creek Lake, MD and Blackwater Falls, WV there are plenty of recreational activities, shopping, restaurants and medical facilities nearby. A rare blend of rustic elegance, seclusion, and natural beauty—this is truly a once-in-a-lifetime legacy property that you can call home. Potential for owner financing available.

415 Nazelrod Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$579,000

5 Beds ⋅ 4 Baths

Welcome to this beautifully appointed 5-bedroom, 3.5-bath home located in one of Oakland’s most desirable neighborhoods—Country Club Acres, bordering The Golf Club at Oakland. Offering the perfect blend of modern style, comfort, and convenience, this spacious home is designed to accommodate both everyday living and entertaining. Step inside to discover an inviting open-concept floor plan featuring upscale finishes throughout. The heart of the home is the stunning kitchen, complete with sleek cabinetry, solid surface countertops, stainless steel appliances, a large center island, and contemporary lighting that creates a bright and welcoming atmosphere. The adjoining dining and living spaces flow seamlessly together, making gatherings effortless. The home offers five generously sized bedrooms, including a spacious primary suite, along with 3.5 well-appointed bathrooms. The finished basement provides valuable additional living space perfect for a family room, recreation area, home gym, office, or guest accommodations. Outside, enjoy the charm of the covered front porch and the peaceful setting of this established community. The oversized attached one-car garage offers ample room for parking, storage, and outdoor equipment. Located just minutes from downtown Oakland, schools, shopping, dining, and Deep Creek Lake attractions, this exceptional property combines modern living with a highly desirable location.

428 Sam Snead Cir, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$375,000

4 Beds ⋅ 2 Baths

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:

$899,900

5 Beds ⋅ 5 Baths

One-of-a-kind Youghiogheny riverfront estate offering 400 feet of water frontage on 5+ acres and 2 separate lots. Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to ceiling fireplace, log accent walls and exposed beams. Features include multiple fireplaces (wood & gas), Andersen doors & windows, trex decking, hardwood floors, metal roof, custom cabinets in kitchen & bedroom suites, eat-in kitchen, and sold furnished! Enjoy a picturesque setting in a riverfront setting with NO HOA restraints for this home. The house on lot 8 is also offered on its own WITHOUT the adjacent riverfront building lot for $775,000, MLS listing #MDGA2012378. Lot #9 offered by itself for $175,000 MLS #MDGA2012380

251 Robinwood Dr, Oakland

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

$1,499,000

5 Beds ⋅ 5 Baths

Experience what may be the most spectacular view in all of Deep Creek Lake! Perched in an extraordinary setting, this exceptional Yellowstone Log Home showcases breathtaking panoramic water views that create a true “top of the world” feel. Designed to capture the scenery from every angle, the main level features an open-concept layout with soaring natural light, a stunning stone fireplace, luxury kitchen, spacious primary suite, and a beautiful three-season room with its own stone fireplace. Step outside to the expansive deck—perfect for entertaining, relaxing, and taking in unforgettable sunsets. The loft offers flexible living space ideal for an office, rec room, or additional lounge area. Downstairs, the finished lower level includes a second family room with stone fireplace, an additional primary suite, two more bedrooms, full bath, and walk-out access to a covered patio. The impressive 40’ x 28’ detached garage provides three bays of storage plus finished living space above with a bedroom suite, living area, bunks, and private deck overlooking the lake. Projected to do over $75,000/year in rental income! A rare opportunity to own one of Deep Creek Lake’s most unforgettable vantage points—where luxury, space, and unmatched scenery come together.

670 Woodlands Hill Ln, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$1,200,000

4 Beds ⋅ 5 Baths

Outdoor lovers retreat! Wooded trails and wildlife - HUNTING ALLOWED with no HOA restrictions. Welcome to mountain and lake living at its finest. Nestled on 6.89 very private acres, 122 Woodlands Hill Lane offers the perfect blend of seclusion, space, and comfort in one of Garrett County’s most desirable settings in the heart of Deep Creek Lake. This impressive 4-bedroom, 4.5-bath home features approximately 4,000 square feet of living space designed for gathering, relaxing, and enjoying the beauty of Western Maryland. Spacious living areas and multiple levels of comfort. The home sits on a 6.89-acre lot with surrounding parcels also for sale SEPARATELY totalling 21 ACRES for privacy, building or both! Inside, you'll find generous living spaces with warm finishes, hardwood flooring, and a fireplace that creates an inviting atmosphere year-round. The thoughtfully designed layout offers room for family and guests alike, while the expansive setting outside provides privacy and endless opportunities to enjoy nature. Features include a fireplace, wood stove, hardwood flooring, large basement, storage shed and substantial interior space. Other features include Anderson windows and doors, steam room/shower, infrastructure for central A/C and generator. Whether you're looking for a full-time residence, a mountain retreat, or a place to create unforgettable memories near Deep Creek Lake, this property delivers a rare combination of acreage, privacy, and convenience. Enjoy the peaceful surroundings while remaining just minutes from Deep Creek Lake recreation, dining, state parks, Wisp Resort, and all the outdoor adventures Garrett County has to offer. Your mountain escape awaits. Call today! The following surrounding parcels are also available for sale, please inquire. Parcel 657 - 3.15 ACRES Parcel 634 - 5.0 ACRES Adjoining parcel 658 also for sale: 6.89 ACRES - MLS #MDGA2011974 can also be purchased from separate owner

122 Woodlands Hill Ln, Oakland

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

$2,499,900

4 Beds ⋅ 2 Baths

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:

$374,900

2 Beds ⋅ 1 Baths

Charming vintage Deep Creek Lake log cabin ideally located in the heart of Deep Creek Lake just minutes from area amenities. Full of character and thoughtfully restored, this established rental property is being sold completely furnished and turnkey. Enjoy filtered lake views from the inviting covered front porch, then unwind in the hot tub or gather around the fire pit after a day on the lake. Conveniently located directly across from Silver Tree Marine and Dutch’s at Silver Tree and just a short drive to Deep Creek Lake State Park. A rare opportunity to own a truly unique Deep Creek getaway with timeless cabin charm!

560 Glendale Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$999,999

3 Beds ⋅ 3 Baths

Beautifully renovated lake access log cabin with a deeded dock slip in a quiet cove with private 29 acres of trails (ATVs/snowmobiles permitted). Recent renovations (approx. $200K) include new wrap around deck, new roof, re-stained siding, new kitchen with granite counters, new appliances, new bathrooms, new LVFs throughout the house, new 2 car garage doors, new mini-split heat and A/C units, and mostly new Pella windows and furniture. Selling fully furnished. Enjoy stargazing on a quiet street in front of a fire pit or in your private hot tub. Filtered lake views with the deeded dock slip across the street. Centrally located in the mid-lake area, close to ski resort, beach, and state parks.

127 Paradise Hts, Oakland

Listing courtesy of XRealty.NET LLC. 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

$745,000

Spacious five-bedroom lakeview home offering the perfect blend of relaxation and warmth from the moment you enter. This established rental property “Terp’s Hideaway” features an open and inviting floorplan, five bedrooms, two family rooms, and three levels of living space, making it an ideal layout for hosting family and friends. Step outside onto the large deck to take in beautiful views or unwind in the private hot tub after a day of adventure. Conveniently located just minutes from Deep Creek Lake State Park, Wisp Ski & Golf Resort, Thousand Acres Golf Club, several dining options, convenience stores, ice cream, coffee shops, and cinema. Easy access to year-round recreation, dining, and entertainment. A fantastic opportunity, call today to preview!

638 Glendale Rd, Oakland

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

$699,000

5 Beds ⋅ 4 Baths

Tucked away on a picturesque 1.83-acre parcel, this charming log home offers the perfect blend of rustic character and modern comfort. Amongst the 4,200+ SF, you will find five spacious bedrooms, two family rooms, a playroom, an office/den, a large loft, spacious pantry, granite counter tops, hardwood flooring and two fireplaces. The warm wood interior and classic log construction create a cozy, inviting atmosphere throughout. A two-car attached garage provides everyday convenience, while the expansive detached garage offers endless possibilities—ideal for hobbies, a workshop, and plenty of space for equipment and boat storage, plus an unfinished room above. The Moss Creek community is centrally located off Sand Flat Road between Oakland and DCL, and this home happens to be at the end of the cul-de-sac on a no-thru street. Enjoy the peace and privacy of country-style living with ample outdoor space, which includes a great yard, large deck, and front covered porch, perfect for entertaining family and friends. Well-suited as a primary or secondary residence!

312 Moss Creek Cir, Oakland

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

$224,900

1 Beds ⋅ 1 Baths

Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath house blends cozy living with endless potential. The upper level offers a cozy living area, a full kitchen, laundry room, bedroom, and full bath. But the real bonus? A spacious 2-car garage with its own entrance. It is perfect for a workshop, extra storage, or even a rental opportunity. With separate entrances for the garage and living space, this property offers built-in flexibility for income potential or multi-purpose use. Plus, the location is minutes to lake activities and downtown Oakland. Don't miss out on the chance to own this versatile gem. Schedule a showing today!

206 Mayhew Inn Rd, Oakland

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

$999,000

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:

$249,900

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

$869,900

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:

$349,000