Rolling Oaks Homes with Key West Architectural style

Rolling Oaks Homes with Key West Architectural style

Welcome to Rolling Oaks, a charming subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This picturesque community is designed for those who appreciate the beauty of nature and the warmth of a close-knit neighborhood. Rolling Oaks boasts lush landscapes, serene surroundings, and a welcoming atmosphere that invites residents to enjoy a comfortable and fulfilling lifestyle.

One of the standout features of Rolling Oaks is its stunning homes, many of which showcase the delightful Key West architectural style. Inspired by the coastal charm of the Florida Keys, these homes are characterized by their vibrant colors, spacious verandas, and distinctive metal roofs. The Key West style not only offers a unique aesthetic but also emphasizes outdoor living, allowing homeowners to embrace the sunny Florida weather year-round. Imagine sipping your morning coffee on a breezy porch or hosting evening gatherings under the stars—this is the lifestyle that Rolling Oaks offers.

Residents of Rolling Oaks enjoy easy access to a variety of amenities, including shopping centers, dining options, and recreational facilities. The community is also conveniently located near major highways, making it easy to explore the attractions of Central Florida, including the world-renowned theme parks and beautiful natural reserves.

Whether you’re a first-time homebuyer, a growing family, or looking to retire in a serene environment, Rolling Oaks in Kissimmee promises a vibrant community and beautiful homes that capture the essence of Florida living. Come discover your dream home in this enchanting subdivision!

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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