Rolling Oaks Real Estate

Rolling Oaks Real Estate

Welcome to Rolling Oaks, a charming subdivision nestled in the heart of Kissimmee, Florida, within the beautiful Osceola County. This picturesque community offers a perfect blend of suburban tranquility and convenient access to the vibrant attractions of Central Florida.

Rolling Oaks is characterized by its lush landscapes, tree-lined streets, and a warm sense of community. The subdivision features an array of well-designed homes, ranging from cozy single-family residences to spacious modern designs, catering to families of all sizes. Residents enjoy the privacy of their own backyards while being part of a friendly neighborhood atmosphere.

One of the standout features of Rolling Oaks is its prime location. Just a short drive away, you’ll find the world-renowned theme parks of Walt Disney World and Universal Studios, making it an ideal spot for families and adventure seekers alike. Additionally, the community is conveniently situated near shopping centers, dining options, and recreational facilities, ensuring that all your daily needs are within easy reach.

For outdoor enthusiasts, Rolling Oaks offers access to nearby parks and nature trails, perfect for weekend strolls or family picnics. The community also hosts various events throughout the year, fostering connections among neighbors and creating lasting memories.

Whether you’re looking to settle down in a friendly environment or seeking a vacation home close to the excitement of Central Florida, Rolling Oaks is the perfect place to call home. Experience the charm and convenience of this delightful subdivision, where community spirit meets the thrill of nearby attractions!

Newest Listings in Rolling Oaks

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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