Rolling Oaks Ph 5 Homes with Gated Amenities

Rolling Oaks Ph 5 Homes with Gated Amenities

Welcome to Rolling Oaks Phase 5, a hidden gem nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This exquisite subdivision offers a perfect blend of tranquility and modern living, making it an ideal haven for families and individuals alike.

Rolling Oaks Phase 5 is characterized by its beautifully designed homes that reflect contemporary architecture and thoughtful layouts. Each residence is crafted with attention to detail, providing spacious interiors and inviting outdoor spaces that are perfect for entertaining or simply enjoying the Florida sunshine. The community's gated amenities ensure peace of mind, offering residents a secure environment to relax and thrive.

As you explore this charming neighborhood, you'll find lush landscaping and well-maintained common areas that enhance the community's appeal. Rolling Oaks Phase 5 is not just a place to live; it's a lifestyle choice. Residents enjoy access to a variety of amenities, including walking trails, recreational areas, and serene green spaces, fostering a sense of community and connection among neighbors.

Located just minutes away from the bustling attractions of Kissimmee, including world-renowned theme parks, shopping centers, and fine dining, Rolling Oaks Phase 5 strikes the perfect balance between suburban serenity and urban convenience. Whether you’re looking for a family home or a peaceful retreat, this subdivision is a perfect choice for those seeking a vibrant and secure environment in sunny Florida. Discover your dream home in Rolling Oaks Phase 5, where comfort meets community!

Newest Rolling Oaks Ph 5 Homes with Gated Amenities

4 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code

NEW PRICE $465,000 | FULLY FURNISHED | 3 BEDROOMS + BONUS ROOM | 3 FULL BATHS | DUAL PRIMARY SUITES | PRIVATE HOT TUB | MINUTES FROM DISNEY. A NEW PRICE. A PRIME LOCATION. AN OPPORTUNITY WORTH A SECOND LOOK. Newly offered at $465,000 a fully furnished, turnkey cottage ideally positioned within Margaritaville Resort Orlando and just a short walk to the resort amenities.This property delivers the combination today's vacation-home buyer is searching for: location, flexible accommodations, resort lifestyle and exceptional value near Walt Disney World. Whether you're searching for a Florida vacation home, second residence, short-term rental opportunity or personal getaway with income potential, this home offers versatility in one of Central Florida's most recognizable vacation destinations. The prime corner location immediately sets this cottage apart, while its thoughtfully designed 3-bedroom + bonus-room floor plan with 3 full bathrooms provides flexible space for owners, families and vacationing guests. A standout feature is the DUAL PRIMARY-SUITE DESIGN, with private suites located on BOTH the first and second floors. The first-floor primary offers added convenience and direct access to the outdoor living area, while the second suite creates additional privacy for guests or multigenerational stays. Inside, the bright, open-concept design features soaring ceilings, abundant natural light, quartz countertops, stainless steel appliances, upgraded cabinetry and the sought-after "Son of a Sailor" interior package. The kitchen, dining and living areas flow together beautifully, creating a welcoming central gathering space for entertaining, relaxing and vacation living. Step outside and the Florida lifestyle continues. A private paved patio, tropical landscaping and heated above-ground hot tub create your own outdoor retreat, the perfect place to unwind after a day at Disney, enjoy an evening under the palms or simply escape into vacation mode without leaving home. Even better, IT'S ALL INCLUDED. This home is being offered FULLY FURNISHED AND TURNKEY, including furniture, televisions, artwork, décor, linens, kitchen essentials, window treatments, housewares and more. Skip the expense and hassle of furnishing a vacation property and start enjoying it from day one. And then there's the LOCATION. Situated inside Margaritaville Resort Orlando, you're surrounded by the resort lifestyle while remaining just minutes from Walt Disney World, Universal Orlando, Epic Universe, championship golf, shopping, dining and Central Florida's world-famous attractions. Nearby Sunset Walk adds restaurants, entertainment, live music, shopping and year-round events to the experience.What an exciting opportunity to own a furnished, flexible-layout vacation property in the heart of Orlando's tourism corridor.Dual primary suites. Bonus room. Private hot tub. Fully furnished. Resort lifestyle. Minutes from Disney. Don't just vacation in paradise, OWN IT. Schedule your private showing of 8060 Dreamsicle Drive today.

8060 Dreamsicle Drive, Kissimmee

1 Beds ⋅ 1 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code

Welcome to Pirate Way — a beautifully furnished 1-bedroom cottage located in the heart of Margaritaville Resort Orlando! If you've been dreaming of owning your own piece of paradise, this charming, turnkey cottage offers the perfect combination of vacation-home lifestyle, resort living and investment potential. Step inside and you'll immediately feel the Margaritaville vibe. This fully furnished, one-story cottage features ceiling fans throughout, a bright and colorful coastal-inspired design, and an open-concept kitchen that flows seamlessly into the living area — perfect for relaxing after a day at the parks or entertaining family and friends and NO carpet! Step outside to your private back patio, complete with a table and four chairs plus two lounge chairs — the perfect spot to enjoy your morning coffee or unwind after a day of fun. And then there's the LOCATION! This cottage is ideally positioned within Margaritaville Resort Orlando, just steps from the resort's incredible amenities. Enjoy access to 7 resort pools, the Fins Up Beach Club, fitness center, resort transportation and shuttle service to the theme parks. The community is also pet-friendly and features Barkaritaville, a dedicated dog park. When you're ready to venture out, you're surrounded by everything that makes this area one of Central Florida's most desirable vacation destinations. Sunset Walk is just steps away, offering restaurants, bars, live entertainment, shopping and more, while Island H2O Water Park is right nearby. Disney, Universal, SeaWorld and Orlando's other major attractions are all just minutes away. Even better, the monthly HOA includes high-speed internet, cable, phone service, daily doorstep trash pickup, landscaping, pest control, a resort shuttle and a shuttle to the parks adding even more convenience to resort living. Whether you're looking for a vacation getaway, second home, full-time residence or a short-term rental investment, this is your opportunity to own a fully furnished cottage in one of Central Florida's most popular resort communities. Pack your flip-flops and come see why life really is better in Margaritaville! Schedule your private showing today!

3054 Pirate Way, Kissimmee

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

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Brian Scott Smith PA

Before launching his real estate career, Brian Smith spent over a decade in the construction industry, working hands-on with builders throughout Central Florida. That experience gave him an in-depth understanding of the homebuilding process—insight he now brings to his real estate clients, offering a level of expertise that sets him apart from most agents. In 2012, Brian joined his family’s firm, ERA Professional Realty. It was a “sink or swim” environment, and at the time, he wasn’t sure why his parents were so tough on him. Looking back, he’s grateful—they were preparing him for the challenges of a demanding industry, and that foundation shaped the dedicated, knowledgeable agent he is today. Since then, Brian has consistently ranked among the area’s top producers. His success is built on attention to detail, deep market knowledge, and a genuine commitment to client service. He stays current with real estate technology and prides himself on creating a smooth, informed experience for every buyer and seller. Brian has helped countless retirees transition to and from Florida, and he takes particular pride in assisting veterans and seniors through major life changes. In 2015, he was honored as REALTOR® of the Year at ERA Grizzard Real Estate. Today, he continues to list and sell millions of dollars in residential real estate annually and is expanding into commercial properties to serve an even broader range of client needs. A fifth-generation Floridian, Brian was born and raised in Central Florida. His local knowledge runs deep—something clients find to be a true asset when navigating the real estate market. Outside of work, Brian’s greatest pride is being a dad. He enjoys fishing with his son and watching his daughters grow into her own unique spirit. If you’re thinking about making a move, Brian Smith, REALTOR®, is a full-time agent ready to bring hard work, experience, and local expertise to your next real estate transaction.

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