Rolling Oaks Homes with Deed Restrictions Community Extras

Rolling Oaks: The Perfect Subdivision in Kissimmee, FL

Welcome to Rolling Oaks, a charming subdivision nestled in the heart of Kissimmee, FL. Located in Osceola County, this community is known for its peaceful atmosphere and family-friendly environment. With its convenient location and beautiful homes, Rolling Oaks is the perfect place to call home.

One of the standout features of Rolling Oaks is its Homes with Deed Restrictions Community Extras. This means that residents can enjoy the benefits of a well-maintained neighborhood with certain guidelines in place to ensure the overall quality and appearance of the community. From well-manicured lawns to consistent architectural standards, Rolling Oaks upholds a high standard of living that residents can be proud of.

In addition to the community extras, Rolling Oaks offers a range of amenities and conveniences. Residents can take advantage of nearby parks, walking trails, and recreational facilities, perfect for enjoying the outdoors and staying active. The subdivision is also conveniently located near shopping centers, restaurants, and entertainment options, making it easy to meet all your daily needs.

Whether you're a growing family looking for a spacious home or a retiree seeking a peaceful retreat, Rolling Oaks has something for everyone. The diverse range of homes in the subdivision ensures that there is a perfect fit for every lifestyle and budget.

Don't miss out on the opportunity to be a part of this wonderful community. Contact a real estate agent today to explore the available properties in Rolling Oaks and start living your dream life in Kissimmee, FL.

Newest Rolling Oaks Homes with Deed Restrictions Community Extras

$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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