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16 E Pennington St E, Oakland
$189,900
3 Beds ⋅ 3 Baths
Welcome to 16 E. Pennington Street! This charming two-story home in the heart of downtown Oakland offers plenty of space, character, and an opportunity to make it your own, all at an affordable price! Just a short drive to Deep Creek Lake and priced to sell! Spacious colonial offering over 1,550 square feet, this home features three spacious bedrooms, two full bathrooms, and a convenient main-level half bath. The inviting front porch is a great place to relax, while the covered rear porch and deck provide additional space to enjoy the outdoors. Inside, you'll find a comfortable living room, a separate dining room with plenty of room to gather, and a spacious kitchen featuring oak cabinetry, a gas stove, and room for a large table. A generous laundry area, convenient half bath, and additional storage complete the main level. Upstairs, the primary bedroom offers great natural light and a spacious closet. Two additional generously sized bedrooms and two full bathrooms provide flexibility for family, guests, or a home office. The home underwent a full renovation in 2003 and offers additional improvements such as updated trex front porch steps and an insulated crawl space. Natural gas heat, public utilities, and no HOA add to the appeal. Situated on a nearly quarter-acre lot with off-street parking, this property offers the charm of an older home with plenty of room to personalize. Conveniently located in Oakland with access to local shopping, dining, and everyday amenities, it's a wonderful opportunity for a primary residence or investment property. Don't miss your chance to make this Oakland home your own!

16 E Pennington St E, Oakland

Listing courtesy of The KW Collective. Contact:

335 Pergin Farm Rd, Oakland
$475,000
3 Beds ⋅ 3 Baths
Enjoy the convenience of one-level living at 335 Pergin Farm Road. This 3-bedroom, 3-bath lake area home features recent interior upgrades that blend its original character with a refreshed feel, including updated flooring, bathrooms, appliances, cabinetry, and countertops. The primary bedroom offers a walk-in closet and tiled shower. Adding to the functional layout is a finished basement that provides additional living and flex space to suit a variety of needs and a full bathroom with a walkout. An attached 2-car garage adds everyday convenience, and the flat, 2.00-acre lot features an expansive grassy yard with plenty of room to enjoy the outdoors. Superior walls ensure a top of the line foundation from the ground up. Conveniently located near Deep Creek Lake, Wisp Resort, and the shops, restaurants, and amenities of Oakland, this property offers a great combination of updated interior features, usable outdoor space, and prime location for full time living or second home enjoyment.

335 Pergin Farm Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

74 Parks Rd, Oakland
$59,900
3 Beds ⋅ 1 Baths
**Investor Special with Mountain & Water Views** Opportunity is knocking at 74 Parks Road in Oakland, Maryland, 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 vacation rental. 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:

459 Santa Fe Trl, Oakland
$299,000
3 Beds ⋅ 2 Baths
Set at the end of a cul-de-sac in the conveniently located Roman Nose Spa community, this three-bedroom, two-bath prefab has a private, wooded setting and seasonal views of Deep Creek Lake! With no through traffic and close to the lake, Wisp Resort, restaurants, recreation, and other amenities, it offers potential as a primary residence, weekend getaway, or vacation rental. All three bedrooms are on the main level. The primary bedroom has its own bath with a jetted tub and walk-in shower, while the other two bedrooms share a second full bath. The home also features an open living area, a large kitchen with skylights, a breakfast area, and a separate dining area. The unfinished basement is currently accessed from outside. There is space to add a staircase from the main level, and the basement could be finished for additional living space. The home needs work and is being sold as-is. The annual road maintenance fee is $300 and covers snow plowing and other maintenance.

459 Santa Fe Trl, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

228 N 4th St, Oakland
$295,000
3 Beds ⋅ 2 Baths
Exquisite 3/4BR, 2BA Craftsman-style residence has been incredibly well maintained and lovingly cared for. Impressive kitchen remodel, hardwood floors, gas fireplace and multiple heat/cooling options. Home shows well - very clean and well-kept and a sensible floorplan. Full basement with overflow sleeping area and storage options. The kitchen is equipped with updated countertops & appliances. Cozy front porch and large rear deck with a spacious yard area (double lot) plus a storage shed. Fantastic location, close proximity to downtown Oakland, directly across the street from the hospital and close to pharmacies, dining options and shopping. Oakland offers a vibrant community atmosphere, with access to local parks, schools, and recreational areas. Conveys with most furnishings.

228 N 4th St, Oakland

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

210 Seneca Ave, Oakland
$225,000
3 Beds ⋅ 1 Baths
Excellent opportunity for first time home buyers or anyone looking for an easy to manage home. This charming ranch-style home offers a perfect blend of comfort and functionality. The floor plan seamlessly connects the combination kitchen and dining area, ideal for gatherings. The kitchen boasts stainless steel appliances, including a double oven and built-in microwave, making meal prep a delight. Cozy up in the inviting living space, perfect for relaxing evenings. The home features three well-appointed bedrooms, including an entry-level option for convenience. Enjoy the look of newly installed luxury vinyl plank throughout. Outside, the level lot and fenced in yard provides ample space for outdoor activities, complemented by a covered side porch and an outbuilding for extra storage. With a driveway for easy parking and a welcoming atmosphere, this home is ready to embrace new memories. Experience the warmth and charm that awaits in this delightful property! Call Today to schedule a showing.

210 Seneca Ave, Oakland

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

4866 Cranesville Rd, Oakland
$269,000
3 Beds ⋅ 2 Baths
Welcome to 4866 Cranesville Road! This 3-bedroom, 2-bath, one-level home offers comfortable living with recent updates throughout, while still maintaining the character of the original home. The layout provides convenient one-floor living and plenty of practical space for everyday life. Outside, the property truly stands out with a large driveway and an impressive detached 3-car garage/shop, offering abundant room for vehicles, storage, hobbies, projects, or a home workshop. Bordering nature conservancy, this home offers a private setting that eliminates the possibility of future development nearby. Located along Cranesville Road, you are just minutes from Oakland MD, Deep Creek Lake, and all of Garrett Counties most popular attractions. If you’re looking for a move-in-ready home with exceptional garage and workspace potential, this one is worth a look!

4866 Cranesville Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

1529 Paradise Point Rd, Oakland
$639,000
3 Beds ⋅ 3 Baths
This exquisite Northern White Cedar Construction (naturally rot resistant) log home offers a harmonious blend of rustic charm and modern luxury. The spacious, open floor plan invites you to experience a warm and inviting atmosphere, accentuated by stunning wood floors and walls, cathedral beam ceiling, and a cozy stone fireplace with glass doors, perfect for intimate gatherings. The heart of the home features a well-appointed kitchen equipped with nice appliances, and an eat-in bar. Retreat to the spacious primary suite, complemented by two additional bedrooms, providing ample space for relaxation. The fully finished basement, with a convenient walkout entrance just steps from the driveway, offers endless possibilities while offering plenty of space to host friends and family. Step outside to discover a beautifully landscaped 0.63-acre fenced yard that backs to lush trees, and includes a playhouse/shed. Enjoy the expansive wrap-around deck with a covered roomy front and rear porch, perfect for morning coffee or entertaining family and friends while watching the valley full of wildlife. The location is just minutes to Deep Creek Lake, Wisp Ski Resort, restaurants, entertainment and food markets.

1529 Paradise Point Rd, Oakland

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

139 S Oakhall Dr, Oakland
$229,000
3 Beds ⋅ 2 Baths
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:

482 Pergin Farm Rd, Oakland
$449,000
3 Beds ⋅ 2 Baths
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:

1407 Broadford Rd, Oakland
$399,900
3 Beds ⋅ 2 Baths
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:

40 Sunshine, Oakland
$159,000
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:

718 Boy Scout Crosscut Rd, Oakland
$459,900
3 Beds ⋅ 2 Baths
Assumable 2.75% VA loan may be available...contact listing agent for details. If peace and privacy are on your must-have list, this one delivers! Picture this: you pull into the driveway and the trees close in around you on three sides, like the forest itself is standing guard. Over an acre of land, and somehow it stays flat and usable instead of the steep terrain so common in this area. This is a lot you can actually walk, garden, and live on. Step onto the front porch and you'll want to grab a seat and get lost in the surroundings. The view stretches out far enough to make your cup of coffee last a little longer every morning. In the evenings, the saltwater hot tub (just a few years young) turns this into the kind of backyard people usually only dream about. Inside, the kitchen and main-level bathroom were recently remodeled with an eye for quality over trend, so you get the updates without the "flip house" feel. The ensuite bedroom on the main level is a fantastic one-level living option. Out back, a garage-sized shed and a separate potting shed give you room for tools, toys, or a hobby waiting to happen, and there's a garden plot already established for anyone who wants fresh vegetables all summer long. This is a property that's already figured out what matters: privacy, usability, upgrades that make daily life easier. Come see why the setting sells itself.

718 Boy Scout Crosscut Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

187 Lower Penn Point Dr, Oakland
$1,425,000
3 Beds ⋅ 2 Baths
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:

102 N 3rd St, Oakland
$259,900
3 Beds ⋅ 2 Baths
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:

321 Deer Park Hotel Rd, Oakland
$384,500
3 Beds ⋅ 2 Baths
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:

2918 Oakland Sang Run Rd, Oakland
$185,000
3 Beds ⋅ 1 Baths
This charming 3-bedroom, 1-bathroom ranch-style home in the desirable Oakland Sang Run Rd area near the Youghiogheny River offers a blend of modern upgrades and classic appeal. Recently renovated in 2022, the interior features an open floor plan with luxury vinyl tile flooring, built-ins, and a gourmet kitchen equipped with stainless steel appliances and upgraded countertops. Enjoy the convenience of main floor laundry and double-pane windows for energy efficiency. Set on a generous 4.88-acre lot, the exterior includes an outbuilding and a wood/metal shed, perfect for storage or hobbies. The property provides ample driveway parking and a serene outdoor space for relaxation. Located in a vibrant community, residents benefit from nearby parks, excellent schools, and convenient public services. This home is ideal for those seeking a peaceful retreat with easy access to local amenities. Don't miss the opportunity to make this property your own!

2918 Oakland Sang Run Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

127 Paradise Hts, Oakland
$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:

163 Mitchell Dr, Oakland
$279,000
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. SELLER OFFERING A $2500 BUYER CLOSING COST CREDIT AND A HOME WARRANTY WITH ACCEPTABLE OFFER.

163 Mitchell Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

1021 E High St, Oakland
$234,000
3 Beds ⋅ 2 Baths
***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:

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