Oakland Homes with Pool

Oakland Homes with Pool

Welcome to Oakland, Maryland – a charming gem nestled in the heart of Garrett County, where the beauty of nature meets the warmth of a close-knit community. Known for its stunning landscapes and outdoor recreational opportunities, Oakland is a haven for those who appreciate the great outdoors. With its picturesque lakes, lush forests, and scenic mountains, residents enjoy a plethora of activities, from hiking and biking to fishing and boating.

One of the most enticing features of Oakland is its selection of homes with pools. Imagine coming home after a long day to your very own private oasis, where you can unwind and soak up the sun. These homes not only offer the luxury of a refreshing pool but also provide a perfect setting for entertaining friends and family. Picture summer barbecues, evening swims, and laughter-filled gatherings right in your backyard.

The real estate market in Oakland boasts a variety of properties, each with its unique charm and character. Whether you’re seeking a cozy cottage or a spacious family home, you’ll find options that cater to every lifestyle. Many of these homes are designed with modern amenities while still embracing the rustic charm that Oakland is known for.

With its friendly atmosphere, rich history, and abundant recreational opportunities, Oakland, MD, is the perfect place to call home. Dive into the serenity of poolside living and discover the enchanting lifestyle that awaits you in this beautiful town. Your dream home with a pool is just a splash away!

Newest Oakland Homes with Pool

$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:

$379,500
1 Beds 1 Baths
Experience the best of Deep Creek Lake from this beautifully situated 2-story, 1-bedroom, 1-bath condominium at Will O' The Wisp. Offering 636 square feet of comfortable living space and spectacular lake views, this waterfront retreat is the perfect personal getaway, year-round residence, or vacation rental investment. Enjoy your morning coffee while taking in panoramic views of the water, then spend the day enjoying the incredible amenities that make Will O' The Wisp one of Deep Creek Lake's most sought-after destinations. Residents and guests have access to an indoor swimming pool and hot tub, racquetball court, fitness center, and arcade, providing year-round entertainment for all ages. 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. Boating enthusiasts will appreciate the community's 22 dock slips available for reservation and 4 dedicated jet ski docks, making it easy to get out and enjoy the lake. When it's time to relax, take advantage of two exceptional waterfront restaurant and bar venues located on-site, both featuring stunning lake views and convenient commercial docking. With professional on-site management, resort-style amenities, and a premier lakefront location just minutes from Wisp Resort, state parks, golf courses, and countless outdoor activities, this property offers an incredible opportunity to own a piece of Deep Creek Lake's waterfront lifestyle. Whether you're looking for a weekend escape or a property with strong rental appeal, this lakeview condo checks all the boxes.

20160 Garrett Hwy Unit #C307, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$575,000
3 Beds 2 Baths
With some minor modifications to the unit, it is possible for this condo to be rented as two separate condos (501 two BR and 701 one BR). Lakefront living at it's best can be found in this completely renovated spacious condo. This three-level unit is the perfect place to get away together! With space to come together and space to escape, this unit promises both privacy and togetherness for a memorable Deep Creek Lake experience! The first level has a full kitchen with wine fridge and attached living room with an electric fireplace, queen sleeper sofa, high top table with stools and a breathtaking balcony. Just up the stairs, enjoy the king bed in a loft bedroom that overlooks the living room and towering two-story window facing Deep Creek Lake! Also on this level is another bedroom with a Queen bed that shares a hallway bathroom with luxury finishes and a walk-in shower. On the top level you will enjoy even more space and accommodations. The 7th floor level has an additional hallway entrance for more privacy. Relax in the King bed and look out to your private balcony with gorgeous lake views. This space also features a well appointed luxury bathroom with walk-in shower and double bowl sinks. An additional mini-fridge and Keurig coffee maker provide easy access if you don't want to go downstairs. Up above in the vaulted loft curl up in the Queen size bed and take in panoramic sunrise views from every angle. Head down to the sandy beach to watch the water gently roll along the sandy shore of the resort’s private beachfront. No matter the season, there is plenty to keep you entertained with an on-site indoor pool, game room, fitness center, and more! 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.

20160 Garrett Hwy Unit #F501-701, 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:

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