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. Located in the picturesque Osceola County, this charming community offers the perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and everyone in between.

Rolling Oaks is renowned for its stunning homes situated within a secure, gated community, ensuring peace of mind for all residents. The guard-gated entrance provides an added layer of security, allowing you to relax and enjoy the comforts of home without worry. The beautifully landscaped surroundings, paired with well-maintained streets, create a welcoming atmosphere that you’ll be proud to call home.

The homes in Rolling Oaks boast a variety of architectural styles, catering to diverse tastes and preferences. Whether you’re looking for a cozy single-family home or a spacious property for entertaining, you’ll find a range of options to suit your needs. Many of these residences feature modern amenities, open floor plans, and lush outdoor spaces perfect for enjoying Florida’s year-round sunshine.

Beyond the gates, Rolling Oaks offers easy access to a variety of shopping, dining, and recreational opportunities. With nearby parks, golf courses, and the enchanting attractions of Kissimmee and Orlando just a short drive away, you’ll never run out of things to do.

Experience the charm of Rolling Oaks, where community spirit thrives, and your dream home awaits. Embrace the lifestyle you’ve always wanted in this beautiful Florida oasis!

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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