Rolling Oaks Homes with Gated Community - Guard Community Features

Rolling Oaks Homes with Gated Community - Guard Community Features

Welcome to Rolling Oaks, a serene and inviting subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This charming gated community offers a perfect blend of privacy and security, making it an ideal haven for families, retirees, and anyone seeking a peaceful lifestyle.

As you enter Rolling Oaks, you’ll be greeted by beautifully landscaped grounds and the comforting presence of a dedicated guard at the entrance, ensuring a safe and serene environment for all residents. The community is thoughtfully designed to foster a sense of belonging, featuring tree-lined streets, well-maintained sidewalks, and a friendly atmosphere that encourages neighborly connections.

The homes in Rolling Oaks are a testament to quality and craftsmanship, boasting a variety of architectural styles that cater to diverse tastes. From spacious single-family homes to charming villas, each residence is designed with comfort and functionality in mind. Many properties feature expansive yards, perfect for families and pets to enjoy the Florida sunshine.

In addition to its inviting homes, Rolling Oaks is conveniently located near a wealth of amenities. Residents can take advantage of nearby shopping, dining, and entertainment options, all while being just a short drive from the stunning attractions that Kissimmee and the greater Orlando area have to offer.

Whether you’re looking for a peaceful retreat or an active lifestyle, Rolling Oaks provides the perfect backdrop for creating lasting memories. Discover the charm and security of this exceptional community today, and see why so many have chosen to call Rolling Oaks home!

Newest Rolling Oaks Homes with Gated Community - Guard Community Features

$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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