Rolling Oaks Homes with Gated Community - No Guard Community Features

Rolling Oaks Homes with Gated Community - No Guard Community Features

Welcome to Rolling Oaks, a serene and picturesque subdivision nestled in the heart of Kissimmee, Osceola County, Florida. This charming community embodies the perfect blend of tranquility and convenience, making it an ideal place for families, retirees, and everyone in between.

Rolling Oaks offers a selection of beautifully designed homes that cater to diverse lifestyles and preferences. Each residence is thoughtfully crafted with modern amenities and spacious layouts, ensuring comfort and style for every homeowner. The homes are set against a backdrop of lush greenery and vibrant landscapes, creating a peaceful retreat from the hustle and bustle of everyday life.

One of the standout features of Rolling Oaks is its gated community status, providing residents with an added sense of security and privacy. While the community is not staffed with a guard, the gated access ensures that you can enjoy peace of mind while relishing the beauty of your surroundings. The absence of a guard allows for a more relaxed atmosphere, fostering a close-knit community where neighbors become friends.

In addition to its stunning homes, Rolling Oaks is conveniently located near a variety of shopping, dining, and recreational options. Whether you're exploring the nearby parks, indulging in local cuisine, or enjoying family outings at the famous attractions of Kissimmee, you'll find that everything you need is just a short drive away.

Come discover the charm of Rolling Oaks, where your dream home awaits in a community that feels like family. Experience the perfect blend of comfort, security, and convenience in one of Florida's most desirable locations!

Newest Rolling Oaks Homes with Gated Community - No Guard Community Features

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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