Oakland, MD Real Estate Search

Oakland, MD Homes with a Pool for Sale

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Newest Oakland, MD Homes with a Pool for Sale

$2,925,000
4 Beds ⋅ 4 Baths
A rare opportunity to own a lakefront property in the Blakeslee. Located in one of best coves and communities on Deep Creek Lake, the 4 bedroom, 3.5 bath property offers the perfect home and lot package for the best in lakefront living. The 1+ acre wooded property with 150' of premium frontage was the first building site purchased when the development opened . The gently sloping wooded sunset facing lot provides easy access to the lake and dock areas. The current owners have added multiple landscape upgrades including paver stone walkways along with lakeside picnic and fire pit areas. A paved circular driveway provides easy year round access from the street. With lake and summer sunset views from nearly every room, the well designed home offers an open floor plan featuring plenty of window coverage. The main level offers a recently upgraded kitchen and lake facing eating area. A large lake facing great room with fireplace adjoins a cozy family room with its own fireplace and direct deck access. The recently added primary bedroom suite includes a spacious bedroom, luxurious bath, 2 walk in closets and a bonus room currently used as an office. The second floor includes a second primary suite and two spacious bedrooms along with a loft. There is also a lower level with a room that could be a game and or work out area. Many would consider the recently added lakeside covered porch with impressive wood fireplace their favorite spot. It offers direct access to the new deck and primary suite. The property also offers an attached 2 car garage and a detached 24 x 24 garage with plenty of interior height for boat and or tall vehicle storage. Additional upgrades and features includes the addition of a detached 2 car garage, complete deck replacement, whole house generator, replacement and updated HVAC and security systems. The roof shingles have also been recently replaced . Blakeslee is considered by many to be the finest community in the Deep Creek Lake area. The developers believed quality was more important than quantity and designed a community with great amenities and over 100 acres of open space that is restricted from additional development. Blakeslee has also attracted a healthy mixture of full time and vacation owners. The self managed community offers many unique amenities. These amenities include a community center with indoor heated pool, locker rooms, kitchen and decking. Two tennis courts along with a basketball and pickleball courts are well maintained . A multipurpose field is available for outdoor games. A trail system runs through the wooded areas for area residents. Other important features include a storage areas for boats and trailers along with a dedicated trash removal area. It all adds up to a a great opportunity to experience all the benefits that home ownership in the Deep Creek Lake area has to offer. Schedule your showing today as homes for sale in this community typically don't last long.

255 Thornberry Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$998,000
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.

17240 Garrett Hwy, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$6,499,900
8 Beds ⋅ 9 Baths
Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with a sprawling island, Wolf range, and access to a four-season room that opens fully to the outdoors through custom bi-fold doors. The main-level primary suite spans nearly 900 sq ft with a private balcony, soaking tub, his-and-her vanities, and a massive walk-in closet. Enjoy five fireplaces, an indoor pool with fountains and a full bath, and three levels of outdoor living, including an outdoor kitchen, built-in hot tub with gazebo, outdoor shower, and deck drainage system to keep lower levels dry. Entertain with ease in the rec room with an industrial-style bar, climate-controlled wine cellar, and fully equipped gym. Three attached garages connect to a locker-style mudroom, with a lower-level garage ideal for a side-by-side or lake toys. Radiant heat, a whole-house generator, and three dock slips make this property as functional as it is flawless. A rare opportunity to own a true statement home in one of Deep Creek Lake’s most prestigious communities. Call today for your private tour!

47 Holy Cross, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$760,000
4 Beds ⋅ 5 Baths
Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just minutes from Deep Creek Lake and Oakland. This 4-bedroom, 4.5-bath home has been carefully updated to balance comfort, practicality, and modern style. The main level features hardwood floors, radiant heat for added comfort, and open gathering spaces with quiet nooks for reading or hobbies. Upstairs, two primary bedrooms with private baths provide flexibility for family or guests. The full apartment-style basement includes its own kitchen, laundry, and heated floors, offering an inviting space for extended stays or independent living. Outdoors, a stamped concrete driveway leads to an oversized two-car garage, with additional garages and sheds for storage or projects. A fenced in-ground pool, hot tub, and wood decking create a welcoming space for entertaining and relaxation. With thoughtful upgrades throughout, extensive amenities, and close proximity to both town and lake, this property offers the best of convenience and privacy in one setting.

1909 Pysell Crosscut Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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