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 vibrant Osceola County. This charming community is a hidden gem, offering a perfect blend of tranquility and accessibility, making it an ideal place for families, retirees, and everyone in between.

Rolling Oaks is renowned for its stunning homes that showcase the enchanting Key West architectural style. With their vibrant colors, inviting porches, and lush landscaping, these homes exude a tropical charm that transports you to a sunny paradise. Each residence is thoughtfully designed to maximize comfort and style, featuring spacious layouts, modern amenities, and plenty of natural light. Imagine sipping your morning coffee on a breezy porch or hosting friends and family in your expansive backyard—this is the lifestyle that Rolling Oaks offers.

Beyond the beautiful homes, the community is surrounded by lush greenery and scenic views that create a serene atmosphere. Residents enjoy a variety of local parks, recreational facilities, and nearby shopping and dining options, ensuring that everything you need is just a stone's throw away. The proximity to major highways and attractions, including the world-famous Walt Disney World, adds to the allure of this location, making it perfect for those who crave adventure and excitement.

Whether you’re looking for a permanent residence or a vacation getaway, Rolling Oaks in Kissimmee is the perfect place to call home. Discover the charm of Key West-style living in this vibrant community—your dream home awaits!

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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