Rolling Oaks Homes with Two Story Property Description

Welcome to Rolling Oaks, a serene and picturesque subdivision nestled in the heart of Kissimmee, Florida. This charming community is located in Osceola County, where lush landscapes and vibrant flora create a tranquil retreat just minutes from the excitement of Orlando. Rolling Oaks is perfect for families, professionals, and retirees alike, offering a harmonious blend of comfort and convenience.

One of the standout features of Rolling Oaks is its stunning two-story homes. These residences are designed with both elegance and functionality in mind, providing ample living space for families to grow and thrive. With spacious floor plans, these homes often feature open-concept layouts that seamlessly connect living, dining, and kitchen areas, perfect for entertaining guests or enjoying cozy family evenings. Large windows invite natural light to fill the spaces, creating a warm and welcoming atmosphere.

The two-story design allows for added privacy, with bedrooms often located on the upper level, providing a peaceful retreat away from the hustle and bustle of daily life. Many homes in Rolling Oaks boast modern amenities, including gourmet kitchens, spacious master suites, and beautifully landscaped yards, ideal for outdoor gatherings or quiet afternoons in the sun.

Residents of Rolling Oaks enjoy a friendly neighborhood vibe, with nearby parks, shopping, and dining options just a short drive away. With its prime location and charming homes, Rolling Oaks is not just a place to live; it’s a place to call home. Discover the beauty and community spirit of Rolling Oaks today!

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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