Rolling Oaks Homes with Gated Community - Guard Community Features

Rolling Oaks Homes with Gated Community - Guard Community Features

Welcome to Rolling Oaks, an enchanting gated community nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This charming subdivision is a hidden gem that offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and anyone seeking a peaceful lifestyle.

Rolling Oaks boasts a secure, guard-gated entrance, ensuring residents enjoy peace of mind and privacy. The community is designed with safety as a priority, allowing you to relax and unwind in your own sanctuary. As you drive through the beautifully landscaped streets, you'll be captivated by the serene environment and the sense of community that permeates this neighborhood.

The homes in Rolling Oaks are a testament to quality and style, featuring a variety of architectural designs and spacious layouts that cater to diverse tastes and lifestyles. Each residence is thoughtfully crafted with modern amenities, ensuring comfort and convenience for all. Whether you’re looking for a cozy single-family home or a more expansive property, Rolling Oaks has something for everyone.

Residents can take advantage of the community’s lush green spaces, perfect for leisurely strolls, family picnics, or simply enjoying the Florida sunshine. With its close proximity to local attractions, shopping, and dining, Rolling Oaks offers the best of both worlds—secluded living with easy access to the vibrant life of Kissimmee.

Discover the charm of Rolling Oaks and experience a lifestyle where community, security, and comfort come together seamlessly. Your dream home awaits in this delightful enclave!

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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