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 vibrant Osceola County. This charming community offers a serene escape from the hustle and bustle of everyday life, while still being conveniently located near the attractions and amenities that make Kissimmee a sought-after destination.

Rolling Oaks is known for its beautifully designed homes, many of which come complete with luxurious pool amenities. Imagine stepping out into your own private oasis, where you can unwind and soak up the Florida sunshine in your sparkling pool. Whether you’re hosting a summer barbecue, enjoying a morning swim, or simply lounging poolside with a good book, these homes provide the perfect backdrop for relaxation and entertainment.

The subdivision is characterized by its lush landscaping, tree-lined streets, and a friendly neighborhood atmosphere. Families and individuals alike are drawn to the community’s welcoming spirit and strong sense of camaraderie. With nearby parks, walking trails, and recreational facilities, Rolling Oaks is ideal for those who enjoy an active lifestyle.

In addition to its stunning homes and amenities, Rolling Oaks boasts easy access to shopping, dining, and world-renowned attractions, including Walt Disney World and Universal Studios, making it an ideal location for both residents and vacationers.

Discover the charm of Rolling Oaks, where your dream home with a pool awaits. Experience the perfect blend of comfort, convenience, and community in this beautiful Kissimmee subdivision!

Newest Rolling Oaks Homes with Pool Amenities

$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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