Rolling Oaks Homes with Pool Community Features

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 residents a perfect blend of tranquility and convenience. With its lush landscapes and friendly atmosphere, Rolling Oaks is an ideal place to call home.

One of the standout features of this delightful neighborhood is its array of stunning homes, many of which boast private pools. Imagine stepping into your own backyard oasis, where you can unwind under the Florida sun or host memorable gatherings with family and friends. The poolside lifestyle is not just a luxury; it’s a way of life here in Rolling Oaks.

Beyond the inviting homes, the community is designed with family-friendly amenities that promote an active and engaging lifestyle. Residents can enjoy leisurely strolls along scenic walking paths, while children can play in well-maintained parks and playgrounds. The sense of community is palpable, with friendly neighbors and a welcoming spirit that makes everyone feel at home.

Rolling Oaks is conveniently located near shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away. Plus, with easy access to major highways, you can explore all that Central Florida has to offer—from the magical attractions of Walt Disney World to the serene beauty of local lakes and nature preserves.

If you’re seeking a vibrant community with beautiful homes and the luxury of a pool, Rolling Oaks in Kissimmee is the perfect place to make your dreams come true. Come experience the charm and warmth of this wonderful neighborhood today!

Newest Rolling Oaks Homes with Pool Community Features

$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

$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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