Rolling Oaks Homes with Key West Architectural style

Rolling Oaks Homes with Key West Architectural style

Welcome to Rolling Oaks, an enchanting subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This vibrant community offers a unique blend of charm, comfort, and tropical elegance, making it an ideal place for families, retirees, and everyone in between.

The homes in Rolling Oaks are characterized by their stunning Key West architectural style, which evokes the breezy, laid-back atmosphere of the Florida Keys. With their vibrant colors, spacious porches, and inviting designs, these homes are a true reflection of coastal living. Imagine sipping your morning coffee on a wide, wrap-around porch, surrounded by lush landscaping and the gentle sounds of nature. The open floor plans and abundant natural light create a warm and welcoming environment that is perfect for both entertaining and relaxation.

Beyond the beautiful homes, Rolling Oaks offers residents a sense of community that is hard to find elsewhere. Enjoy leisurely strolls through tree-lined streets, friendly neighbors, and a variety of nearby amenities. From parks and recreational facilities to shopping and dining options, everything you need is just a stone's throw away.

Living in Kissimmee means you’re also close to some of Florida’s most famous attractions, including world-renowned theme parks, beautiful lakes, and stunning golf courses. Whether you’re seeking adventure or tranquility, Rolling Oaks is the perfect place to call home. Embrace the Key West lifestyle in this delightful community, where sunshine and smiles are always in season!

Newest Rolling Oaks Homes with Key West Architectural style

$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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