Rolling Oaks Homes with Two Story Property Description

Welcome to Rolling Oaks, a charming subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This vibrant community is perfect for families, professionals, and anyone seeking a serene lifestyle while remaining close to the excitement of Orlando's attractions.

Rolling Oaks boasts a diverse array of stunning homes, with a particular emphasis on elegant two-story properties. These homes are designed with both style and functionality in mind, featuring spacious floor plans that cater to modern living. Imagine coming home to a beautifully appointed residence, where the first floor invites you to entertain guests in expansive living areas, while the second floor provides a private retreat for relaxation. With multiple bedrooms and bathrooms, these homes offer ample space for families to grow and thrive.

The community itself is a haven of tranquility, surrounded by lush greenery and scenic landscapes. Residents can enjoy leisurely strolls through well-maintained parks and winding pathways, fostering a sense of camaraderie among neighbors. Additionally, Rolling Oaks is conveniently located near top-rated schools, shopping centers, and recreational facilities, making it an ideal place to call home.

Whether you're looking for your first home or a place to settle down, Rolling Oaks offers the perfect blend of comfort, elegance, and community spirit. Come explore the possibilities and discover why this enchanting subdivision is the perfect backdrop for your next chapter. Embrace the Florida lifestyle in Rolling Oaks, where your dream home awaits!

Newest Rolling Oaks Homes with Two Story Property Description

$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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