Rolling Oaks Homes with Key West Architectural style

Rolling Oaks Homes with Key West Architectural style

Welcome to Rolling Oaks, a captivating subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This charming community is a hidden gem that perfectly marries the allure of nature with the vibrancy of suburban living. With its lush landscapes and serene surroundings, Rolling Oaks is designed for those seeking a tranquil lifestyle while remaining conveniently close to all the excitement that Central Florida has to offer.

One of the most enchanting features of Rolling Oaks is its distinctive Key West architectural style. These homes are characterized by their vibrant colors, airy porches, and charming metal roofs, evoking a sense of coastal elegance that is both inviting and timeless. Each residence is thoughtfully designed to maximize natural light and create a breezy, open atmosphere that embodies the relaxed Florida lifestyle. Imagine sipping your morning coffee on a spacious porch, surrounded by swaying palms and the gentle sounds of nature.

Residents of Rolling Oaks enjoy access to a variety of amenities, including nearby parks, shopping centers, and top-rated schools. The community is also just a short drive away from the world-famous attractions of Orlando, making it an ideal location for families and professionals alike. Whether you’re looking for a peaceful retreat or a place to create lasting memories with loved ones, Rolling Oaks offers the perfect backdrop for your next chapter.

Discover your dream home in Rolling Oaks today, where the charm of Key West architecture meets the beauty of Florida living!

Newest Rolling Oaks Homes with Key West Architectural style

2939 Castaway Lane, Kissimmee
$330,000
2 Beds ⋅ 3 Baths ⋅ Rolling Oaks SubDv. ⋅ 34747 Zip Code
Welcome to resort-style living in the heart of Margaritaville Resort Orlando! This bright and spacious 2-bedroom townhome with a bonus room is located in the desirable Rolling Oaks community, just minutes from Walt Disney World. The flexible bonus room is currently set up with a twin bed, making it a great additional sleeping space, guest room, or cozy retreat. Inside, you’ll find stylish wood-look tile, quartz countertops, upgraded appliances, wood stairs, high ceilings, a private owner’s closet, and plenty of space to relax and unwind. Whether you’re looking for a full-time residence, a Florida getaway, or a short-term rental investment, this property offers incredible flexibility. Margaritaville Resort delivers the vacation lifestyle with multiple resort-style pools, restaurants and bars, a fitness center, full-service spa, walking trails, gated security, and convenient access to Sunset Walk, where shopping, dining, entertainment, and Island H2O Water Park are practically at your doorstep. With exterior maintenance, landscaping, and lawn care included, you can spend less time worrying about upkeep and more time enjoying everything Central Florida has to offer!

2939 Castaway Lane, Kissimmee
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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