Rolling Oaks Homes with Waterfront

Rolling Oaks Homes with Waterfront

Welcome to Rolling Oaks, a serene subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This charming community is a hidden gem that offers a perfect blend of nature and modern living, making it an ideal choice for families, retirees, and anyone looking to escape the hustle and bustle of city life.

One of the standout features of Rolling Oaks is its stunning waterfront properties. Imagine waking up each morning to the gentle sounds of water lapping at your doorstep, with breathtaking views right outside your window. These homes are designed to embrace the tranquility of waterfront living, providing residents with a unique opportunity to enjoy nature while still being close to the vibrant attractions of Kissimmee.

The homes in Rolling Oaks boast spacious layouts, modern amenities, and beautiful outdoor spaces, perfect for entertaining or simply enjoying a quiet evening by the water. Whether you’re looking for a cozy retreat or a family-friendly abode, you’ll find a variety of options that cater to diverse tastes and lifestyles.

In addition to the beautiful homes and waterfront views, Rolling Oaks is conveniently located near shopping, dining, and recreational activities. Enjoy a leisurely day at nearby parks, explore the local dining scene, or take a short drive to the world-famous attractions of Central Florida.

Experience the best of Florida living in Rolling Oaks, where every day feels like a vacation. Discover your dream home today and immerse yourself in the beauty and tranquility of this exceptional community!

Newest Rolling Oaks Homes with Waterfront

$615,000
3 Beds 2 Baths Rolling Oaks SubDv.
**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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