Rolling Oaks Ph 5 Homes with Deed Restrictions Community Extras

Welcome to Rolling Oaks Phase 5, an enchanting community nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This charming subdivision is designed for those who appreciate the perfect blend of modern living and serene surroundings. Rolling Oaks Phase 5 boasts a collection of beautifully crafted homes, each thoughtfully designed to provide comfort and style.

As a deed-restricted community, Rolling Oaks Phase 5 ensures that the neighborhood maintains its aesthetic appeal and value over time. Homeowners can take pride in their properties, knowing that the community’s standards are upheld, creating a welcoming environment for families and individuals alike. The deed restrictions promote a sense of unity and pride, making it an ideal place to call home.

Residents of Rolling Oaks Phase 5 enjoy access to a variety of community extras that enhance the living experience. From lush green spaces and parks perfect for family picnics to walking trails that invite outdoor exploration, there’s something for everyone. The community’s strategic location means you’re just a short drive from the bustling attractions of Kissimmee, including shopping, dining, and entertainment options that cater to all tastes.

Whether you're a first-time homebuyer or looking to settle down in a vibrant community, Rolling Oaks Phase 5 offers a unique opportunity to embrace a lifestyle of comfort, convenience, and community spirit. Discover your dream home in this beautiful subdivision and experience the best that Kissimmee has to offer!

$1,349,000

8 Beds ⋅ 9 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code

JUST REDUCED $50,000! NOW IS THE TIME! Kick back and embrace the laid-back island rhythm at this breezy lakefront retreat in Margaritaville Resort Orlando, perfectly positioned on Parrot Head Place. Wrapped in carefree Key West charm, this home delivers sun-splashed interiors, coastal hues, and a relaxed, barefoot-friendly layout that makes every day feel like vacation. Out back, your private pool and spa overlook tranquil water views, creating the ultimate setting for lazy mornings, afternoon floats, and sunset cocktails with a soundtrack of good vibes (NEW POOL HEATER FEB 2026). The open living spaces flow effortlessly for easy entertaining, while spacious bedrooms provide a calm, salt-air escape after long days of fun and sun. Perfectly located just minutes from Walt Disney World, Universal Orlando Resort, including the highly anticipated Universal Epic Universe, and SeaWorld Orlando, this home offers the best of both worlds—action-packed adventures by day and laid-back island living by night. Whether you’re chasing thrills, fireworks, or unforgettable family memories, you’ll love coming home to your own private oasis where the pace slows, the music softens, and relaxation takes center stage. Designed for both personal enjoyment and short-term rental success, this home captures the essence of island living with a splash of luxury. Just steps from resort amenities, dining, and entertainment, it’s a place where worries drift away, flip-flops are the dress code, and life moves at a perfectly unhurried pace. Multiple tropical pools with cabanas, lounging areas, and full food & beverage service. Island-inspired restaurants, poolside bars, and casual spots all within walking distance. The St. Somewhere Spa offers massages, facials, body treatments, and salon services. Find your latitude, adjust your attitude, and come home to a true five-o’clock-somewhere lifestyle—complete with lake views, poolside living, and pure Margaritaville Magic! Sale is contingent upon Buyer entering into a property management agreement with Vstays Property Management and assuming and honoring all existing future reservations/bookings.

3052 Parrot Head Place, Kissimmee

Rolling Oaks Ph 5 Homes with Deed Restrictions Community Extras

Newest Rolling Oaks Ph 5 Homes with Deed Restrictions Community Extras