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 captures the essence of laid-back Florida living, offering a perfect blend of tranquility and convenience.

As you stroll through the tree-lined streets of Rolling Oaks, you’ll be captivated by the stunning Key West architectural style that defines many of the homes in this vibrant neighborhood. With their pastel-colored exteriors, metal roofs, and inviting porches, these residences exude a sense of coastal charm that transports you to a tropical paradise. Each home is thoughtfully designed to maximize natural light and create a warm, welcoming atmosphere, perfect for both relaxation and entertaining.

Rolling Oaks is more than just a beautiful collection of homes; it’s a community that fosters connections. Neighbors often gather for weekend barbecues, and children can be seen playing in the nearby parks, creating a friendly and inviting environment. The subdivision is conveniently located near shopping centers, dining options, and recreational facilities, ensuring that all your needs are just a stone’s throw away.

For those who appreciate the allure of Key West architecture and the vibrant lifestyle of Kissimmee, Rolling Oaks is an ideal place to call home. Whether you’re looking for a family residence or a vacation retreat, this charming community offers a unique blend of style and comfort that is hard to resist. Come discover the magic of Rolling Oaks, where your dream home awaits!

$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

Rolling Oaks Homes with Key West Architectural style

Newest Rolling Oaks Homes with Key West Architectural style