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 delightful community is a haven for those seeking a blend of tranquility and convenience, making it the perfect place to call home.

Rolling Oaks features an array of stunning homes that embrace the enchanting Key West architectural style. With their vibrant colors, inviting porches, and distinctive metal roofs, these homes exude a unique charm that captures the essence of coastal living. Each residence is thoughtfully designed to maximize natural light and outdoor space, creating an atmosphere that is both welcoming and relaxing.

As you stroll through the tree-lined streets of Rolling Oaks, you’ll find beautifully landscaped yards and friendly neighbors who share a sense of community spirit. The subdivision is conveniently located near essential amenities, including shopping centers, restaurants, and schools, ensuring that everything you need is just a short drive away. Plus, with easy access to major highways, residents can enjoy all that Central Florida has to offer, from the magical attractions of Walt Disney World to the serene shores of nearby lakes.

Whether you’re looking to raise a family, retire in style, or simply enjoy the vibrant lifestyle that Kissimmee offers, Rolling Oaks is the perfect place to settle down. Experience the unique beauty of Key West architecture and the warmth of a close-knit community—come discover your dream home in Rolling Oaks today!

Newest Rolling Oaks Homes with Key West Architectural style

8117 Surf Street, Kissimmee
$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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