Rolling Oaks Homes with Fitness Center Community Features

Welcome to Rolling Oaks, a hidden gem nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This charming subdivision offers a perfect blend of serene living and vibrant community life, making it an ideal choice for families, retirees, and everyone in between.

Rolling Oaks is known for its spacious homes, beautifully landscaped yards, and friendly neighbors. Each residence is thoughtfully designed, providing ample space for relaxation and entertainment. With a variety of floor plans available, you can find the perfect fit for your lifestyle, whether you seek a cozy retreat or a larger family home.

One of the standout features of Rolling Oaks is its commitment to wellness and community engagement. Residents enjoy exclusive access to a state-of-the-art fitness center, where you can maintain your active lifestyle right at home. Whether you're lifting weights, taking a yoga class, or enjoying a morning jog on the scenic trails, the fitness center is designed to cater to all your health and wellness needs.

In addition to the fitness center, Rolling Oaks boasts a range of community amenities that foster connection and camaraderie among residents. From sparkling swimming pools to playgrounds and picnic areas, there are plenty of opportunities to unwind and socialize. The community hosts regular events, ensuring that there’s always something happening, whether it’s a seasonal celebration or a casual get-together.

With its prime location in Kissimmee, Rolling Oaks offers easy access to shopping, dining, and entertainment options, along with proximity to the enchanting attractions of Central Florida. Discover the perfect blend of comfort, community, and convenience at Rolling Oaks—your dream home awaits!

Newest Rolling Oaks Homes with Fitness Center Community Features

$330,000

2 Beds ⋅ 3 Baths ⋅ Rolling Oaks SubDv. ⋅ 34747 Zip Code

Welcome to resort-style living in the heart of Margaritaville Resort Orlando! This bright and spacious 2-bedroom townhome with a bonus room is located in the desirable Rolling Oaks community, just minutes from Walt Disney World. The flexible bonus room is currently set up with a twin bed, making it a great additional sleeping space, guest room, or cozy retreat. Inside, you’ll find stylish wood-look tile, quartz countertops, upgraded appliances, wood stairs, high ceilings, a private owner’s closet, and plenty of space to relax and unwind. Whether you’re looking for a full-time residence, a Florida getaway, or a short-term rental investment, this property offers incredible flexibility. Margaritaville Resort delivers the vacation lifestyle with multiple resort-style pools, restaurants and bars, a fitness center, full-service spa, walking trails, gated security, and convenient access to Sunset Walk, where shopping, dining, entertainment, and Island H2O Water Park are practically at your doorstep. With exterior maintenance, landscaping, and lawn care included, you can spend less time worrying about upkeep and more time enjoying everything Central Florida has to offer!

2939 Castaway Lane, Kissimmee

$615,000

3 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 34747 Zip Code

**Rare waterfront cottage in Margaritaville Resort Orlando!** One of the few cottages in the community with a premium direct waterfront location, this beautiful 3-bedroom, 2-bath home offers breathtaking water views from both private balconies and a lifestyle unlike any other. **Unlike heavily rented vacation homes, this residence has been privately enjoyed and carefully maintained**, giving it a like-new feel without the wear and tear often associated with short-term rental properties. Whether you're looking for a primary residence, vacation home, or investment property, this home is eligible for short-term rentals and can easily be placed into the resort's rental program if desired. Inside, you'll find numerous upgrades, including tile flooring throughout, an open-concept floor plan, a durable metal roof, quartz countertops, stainless steel appliances, and beautifully designed living spaces that are both stylish and functional. The thoughtfully selected coastal décor perfectly complements the home's character and inviting atmosphere. The spacious kitchen opens seamlessly to the living and dining areas, creating the perfect space for entertaining family and friends. One of the home's most desirable features is its two private waterfront balconies—one on each level—where you can enjoy peaceful water views, your morning coffee, or spectacular Florida sunsets. Margaritaville Resort Orlando offers an exceptional resort lifestyle with multiple resort pools, a fitness center, live entertainment, shopping, dining, Island H2O Water Park, and the vibrant Promenade at Sunset Walk featuring restaurants, bars, boutiques, and year-round entertainment. Located just minutes from Walt Disney World and Orlando's other world-famous attractions, this rare waterfront property offers an outstanding opportunity as a primary residence, second home, or income-producing investment.

8117 Surf Street, Kissimmee

Start Your Search