Oakland, MD Real Estate | Oakland, MD Single Family Homes for Sale

Aww shucks - the sellers have reduced the price!! 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:

$745,000

5 Beds ⋅ 3 Baths

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:

$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:

$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:

$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:

$949,000

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:

$869,900

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:

$349,000

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! Exterior painted summer 2026. Seller will consider owner financing for a well qualified buyer.

1167 Tall Oaks Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$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:

$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:

$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 1.29 private acres, this 4-bedroom, 3.5-bath retreat offers 3,780 finished square feet, sweeping Deep Creek Lake and mountain views, lake access, abundant outdoor living, and an established vacation-rental history. The seller is offering a $30,000 credit towards renovations at closing. This is an opportunity to acquire a substantial Deep Creek property with exceptional views, privacy, rental potential, and a strong collection of amenities—while having immediate resources to make it your own. The open main level features abundant natural light, two wood-burning fireplaces, and expansive entertaining space. The upper-level game room includes a pool table and balcony, while the outdoor living areas include a large deck, hot tub patio, and fire pit. The property also offers a two-car garage and convenient access to the lake for swimming, fishing and paddling. Paradise View is an established vacation rental and is being offered fully furnished, providing the option to continue the existing rental operation while planning future improvements. Located minutes from Deep Creek's restaurants, shops, activities and Wisp Resort, this is a rare combination of privacy, views, space and accessibility.

467 Paradise Ridge Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$1,059,900

4 Beds ⋅ 6 Baths

Panoramic Lake views in the Bray Run community, just minutes from Deep Creek Lake, state parks, and more! Completed 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. Sold Turn-Key, Fully Furnished! If you’re looking for a new home that 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

4 Beds ⋅ 3 Baths

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:

$155,000

3 Beds ⋅ 1 Baths

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:

$1,329,000

6 Beds ⋅ 5 Baths

Stunning 6-Bedroom Kathadin Log Home with Breathtaking 180° views of Deep Creek Lake with Lake Access and a Boat Slip! This exceptional vacation home offers the perfect blend of rustic charm and modern luxury. Boasting 180-degree panoramic views of the sparkling lake, this property is a true mountain retreat. Every room is designed to capture the beauty of the surrounding landscape, with expansive windows allowing natural light to flood the interior and provide endless vistas of the tranquil water. With over 4,000 sq ft of living space, this spacious home features soaring ceilings, rich wood finishes, and an open-concept floor plan that’s perfect for entertaining. The main level living room, with its impressive stone fireplace, is the heart of the home, leading seamlessly into the kitchen and dining area. Whether you’re hosting gatherings or relaxing by the fire, this space offers comfort and style in equal measure. The home includes six generously-sized bedrooms, each offering a serene escape and 5 of them with picturesque lake views. Step outside to the expansive deck that spans the length of the home, perfect for enjoying morning sunrises . A boat slip provides direct access to Deep Creek Lake, offering the ultimate convenience for boating, fishing, and water sports enthusiasts. Additional highlights include a fully finished lower level with a family room, second fireplace, and walk-out access to the outdoor living spaces. The property is complemented by a detached garage and additional parking areas off the drive that can accommodate up to 4 additional cars. Whether you’re looking for a year-round residence, a vacation home, or rental home, this stunning log home offers unparalleled views, a prime location, and a serene lake lifestyle. High rental potential and projection. Don’t miss the opportunity to make this magnificent property your own!

439 Paradise Hts, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$264,500

3 Beds ⋅ 2 Baths

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:

$735,000

5 Beds ⋅ 4 Baths

Beautiful lake access retreat located in the Silver Tree Landings community with an available home warranty. This recently updated contemporary home feels warm and inviting from the moment you walk in (upgrade list available). Offering hardwood flooring, granite countertops, two stone propane fireplaces and cathedral ceilings. The abundance of windows allows the natural light to brighten any season, while offering views from almost every room. The covered and uncovered decks offer plenty of outdoor space to enjoy with family and friends during any season, and the hot tub is always a big hit. If all this isn't enough, take a short walk down to the community docks/lake access area, where you can enjoy the lake and everything it offers. The location checks off one more box, centrally located and just minutes to Unos/Honi Honi, grocery stores, Deep Creek State Park/beach area, Dutch's Restaurant & Harbor Bar, Cinema, Ice Cream, Thousand Acres Golf Club, and Wisp Ski Resort. “Crosswinds” is an established rental. Call today to preview this gorgeous home!

25 Silver Tree Ln, Oakland

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

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