Rolling Oaks Homes with Key West Architectural style

Rolling Oaks Homes with Key West Architectural style

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of Kissimmee, Florida, within the charming Osceola County. This vibrant community offers a perfect blend of serene living and modern conveniences, making it an ideal choice for families, retirees, and everyone in between.

Rolling Oaks is renowned for its stunning homes that showcase the iconic Key West architectural style. These residences are characterized by their vibrant colors, spacious porches, and charming metal roofs, reflecting the laid-back elegance of coastal living. Each home is thoughtfully designed to maximize both comfort and style, with open floor plans, abundant natural light, and lush landscaping that creates a welcoming atmosphere.

Living in Rolling Oaks means enjoying the best of Florida living. Residents have access to a variety of amenities, including well-maintained parks, walking trails, and recreational facilities that encourage an active lifestyle. The community is conveniently located near shopping centers, dining options, and top-rated schools, ensuring that everything you need is just a stone's throw away.

Moreover, the proximity to major highways and attractions like Walt Disney World and Universal Studios makes Rolling Oaks an excellent choice for those who enjoy the excitement of theme parks and outdoor adventures. Whether you’re sipping coffee on your porch or exploring the vibrant local scene, Rolling Oaks offers a lifestyle that is as enchanting as its homes.

Discover the charm of Rolling Oaks today, where your dream home awaits amidst the beauty of Kissimmee!

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

Start Your Search