Rolling Oaks Homes with Pool Amenities

Rolling Oaks Homes with Pool Amenities

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of Kissimmee, Florida, within the serene Osceola County. This charming community offers a perfect blend of tranquility and convenience, making it an ideal location for families, retirees, and anyone seeking a vibrant lifestyle under the Florida sun.

Rolling Oaks is renowned for its beautiful homes, many of which feature luxurious pool amenities that invite you to unwind and bask in the warm Florida climate. Imagine stepping out of your back door to a sparkling pool, perfect for refreshing dips on sunny afternoons or hosting lively gatherings with friends and family. These homes are designed not just for comfort but for creating lasting memories in an idyllic setting.

The subdivision boasts lush landscaping and tree-lined streets, providing a scenic backdrop for daily walks and outdoor activities. Residents enjoy easy access to a variety of local attractions, including shopping centers, dining establishments, and recreational parks. The proximity to major highways ensures that the excitement of Orlando, with its world-famous theme parks and entertainment options, is just a short drive away.

In Rolling Oaks, you’ll find a welcoming community that values connection and camaraderie. Whether you’re lounging by your pool, enjoying a barbecue with neighbors, or exploring nearby attractions, life here is all about enjoying the best of Florida living. Come discover your dream home in Rolling Oaks, where every day feels like a vacation!

Newest Rolling Oaks Homes with Pool Amenities

8117 Surf Street, 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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