Rolling Oaks Homes with Pool Community Features

Rolling Oaks Homes with Pool Community Features

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This charming community embodies the perfect blend of tranquility and modern living, making it an ideal sanctuary for families and individuals alike.

Rolling Oaks is renowned for its stunning homes, many of which feature private pools, inviting you to experience the ultimate in outdoor relaxation and entertainment. Imagine soaking up the Florida sun in your own backyard oasis or hosting memorable gatherings with friends and family around the shimmering waters of your pool. These homes are designed with comfort and luxury in mind, offering spacious layouts, contemporary finishes, and a variety of architectural styles that cater to diverse tastes.

Beyond the homes, Rolling Oaks boasts a wealth of community features designed to enhance your lifestyle. Residents can enjoy beautifully landscaped parks, walking trails, and recreational areas, perfect for morning jogs or leisurely strolls with loved ones. The community fosters a friendly atmosphere, encouraging neighbors to connect and engage in various social activities throughout the year.

Conveniently located, Rolling Oaks provides easy access to major highways, shopping centers, dining, and entertainment options, ensuring that everything you need is just a stone's throw away. With its prime location and exceptional amenities, Rolling Oaks is not just a place to live—it's a place to thrive. Discover the charm of this delightful community and make it your new home today!

Newest Rolling Oaks Homes with Pool 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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