Rolling Oaks Homes with Fitness Center Community Features

Welcome to Rolling Oaks, a vibrant subdivision nestled in the heart of Kissimmee, Florida, within the beautiful Osceola County. This charming community is a perfect blend of suburban tranquility and modern conveniences, making it an ideal place for families, retirees, and anyone seeking a peaceful yet active lifestyle.

Rolling Oaks boasts a variety of stunning homes that cater to diverse tastes and budgets. From cozy single-family residences to spacious modern designs, each property is thoughtfully crafted to provide comfort and style. The lush landscaping and meticulously maintained streets create an inviting atmosphere that residents are proud to call home.

One of the standout features of Rolling Oaks is its commitment to wellness and fitness. The community offers an exclusive fitness center, equipped with state-of-the-art equipment and facilities that cater to all fitness levels. Whether you prefer an energizing workout or a relaxing yoga session, the fitness center provides ample opportunities to stay active and healthy without leaving the comfort of your neighborhood.

Beyond fitness, Rolling Oaks fosters a sense of community with its numerous amenities and social gatherings. Residents enjoy access to parks, walking trails, and recreational areas that encourage outdoor activities and foster connections among neighbors. The friendly atmosphere and community spirit make it easy to forge lasting friendships and enjoy a fulfilling lifestyle.

Located just minutes away from the vibrant attractions of Kissimmee, including shopping, dining, and entertainment options, Rolling Oaks offers the perfect balance of convenience and serenity. Discover the charm of Rolling Oaks and experience a community that truly embodies the essence of Florida living!

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

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