Rolling Oaks Ph 5 Homes with Gated Community - Guard Community Features

Rolling Oaks Ph 5 Homes with Gated Community - Guard Community Features

Welcome to Rolling Oaks Phase 5, a serene and picturesque subdivision nestled in the heart of Kissimmee, Florida, within the beautiful Osceola County. This gated community offers an unparalleled sense of security and tranquility, making it the perfect haven for families, retirees, and anyone seeking a peaceful lifestyle.

Rolling Oaks Phase 5 boasts an array of stunning homes, each designed with modern elegance and comfort in mind. From spacious single-family residences to charming townhomes, there’s a perfect fit for every lifestyle and budget. The meticulously landscaped grounds and well-maintained common areas create a welcoming atmosphere that residents take pride in.

One of the standout features of this community is its 24-hour guard service, ensuring that residents feel safe and secure in their homes. The gated entry provides an extra layer of privacy, allowing you to relax and enjoy the beautiful Florida weather without worry.

In addition to its impressive security features, Rolling Oaks Phase 5 is conveniently located near a variety of amenities. Residents can easily access shopping centers, dining options, and recreational facilities, making it a breeze to enjoy everything Kissimmee has to offer. The nearby parks and nature trails provide ample opportunities for outdoor activities, whether you prefer hiking, biking, or simply taking a leisurely stroll.

Discover the charm and comfort of Rolling Oaks Phase 5, where community, security, and convenience come together to create the ideal living environment in sunny Florida. Come and experience the lifestyle you’ve always dreamed of!

Newest Rolling Oaks Ph 5 Homes with Gated Community - Guard Community Features

$545,000
4 Beds 3 Baths Rolling Oaks Ph 5 SubDv. 34747 Zip Code
Welcome to 8060 Dreamsicle Drive, where every day feels like a vacation and every stay creates an opportunity. Located within the world-renowned Margaritaville Resort Orlando, and is just a short walk to the amenities. This beautifully FULLY FURNISHED and income-producing cottage offers the perfect combination of luxury resort living, investment potential, and unforgettable Florida lifestyle experiences, all just minutes from Walt Disney World. Whether you're searching for a high-performing vacation rental, a second home in paradise, or a personal retreat that generates income when you're away, this turnkey property delivers on every level. From the moment you arrive, the charming Key West-inspired architecture, tropical landscaping, and colorful coastal design create an atmosphere that instantly transports you into vacation mode. Inside, you'll discover a thoughtfully designed open-concept floor plan featuring soaring ceilings, abundant natural light, designer finishes, and the highly sought-after "Son of a Sailor" interior package. The beautifully appointed kitchen features quartz countertops, upgraded cabinetry, stainless steel appliances, and ample space for gathering with family and friends after a day of enjoying everything Orlando has to offer. The spacious living and dining areas flow seamlessly together, creating the perfect environment for entertaining, relaxing, and making lasting memories. This home is a 3 bedroom with a bonus room. One of the most desirable features of this home is the rare dual-primary-suite layout, with (2) PRIVATE OWNER'S SUITES located on both the first and second floors, providing exceptional comfort and flexibility for owners and guests alike. Step outside to your private tropical oasis where a beautifully paved patio, lush landscaping, and above-ground hot tub create the perfect setting to unwind under the Florida sunshine or enjoy peaceful evenings after visiting the nearby theme parks. This home is being offered fully furnished and turnkey, including furniture, televisions, artwork, décor, linens, kitchen essentials, window treatments, housewares, and more, allowing the next owner to immediately begin enjoying the property or continue operating it as a successful vacation rental. Beyond the home itself lies one of Central Florida's most exciting resort destinations. Margaritaville Resort Orlando offers a truly unmatched lifestyle experience featuring multiple resort-style pools, fitness center, on-site water park, entertainment venues, concierge services, and access to the vibrant Sunset Walk district featuring restaurants, bars, live music, shopping, nightlife, family attractions, and year-round events. Located just minutes from Disney Parks, Universal Studios, Epic Universe, championship golf courses, Orlando International Airport, shopping, dining, and major highways, this prime location continues to attract vacationers and investors from around the world. Opportunities like this are becoming increasingly rare. Whether your goal is generating rental income, owning a luxury vacation home, building a real estate investment portfolio, or simply embracing the Margaritaville lifestyle. Paradise isn't just a destination, it can be your next address. Schedule your private showing TODAY!

8060 Dreamsicle Drive, Kissimmee

$394,999
2 Beds 3 Baths Rolling Oaks Ph 5 SubDv. 34747 Zip Code
CALL TO SEE IT TODAY! - FULLY FURNISHED!!! This Margaritaville Resort beauty is amazing and has the Ethan Allen Furniture Package. Your back patio has a PERSONAL HOT TUB. With 2-bedrooms, 2.5-baths, it is the perfect blend of luxury, comfort, and unforgettable full-time or vacation living. Inside you'll find an inviting open-concept floor plan with upgrades throughout, including wood-look ceramic tile flooring, over- and under-cabinet lighting, and custom backsplash and island kickplate tiling in the kitchen. The open living area has in-ceiling speakers, a Klipsch soundbar, Samsung Frame TV, and a queen sleeper sofa for extra guests. Each of the two spacious bedrooms has a large flat screen TV and its own private ensuite bathroom, providing comfort and privacy for owners and guests alike.  The primary suite has a walk-in closet and its own balcony for morning views and coffee, and the second bedroom also has its very own balcony as well, making it the perfect place to unwind while enjoying breathtaking views. Your back patio is designed for ultimate outdoor living. You can enjoy the tranquil park views or relax in your very own hot tub. Your patio area is ideal for entertaining or relaxing after a day at work or the fun day at the parks with a patio table, chairs and sun loungers, giving you endless possibilities to create your own private oasis.  Whether you’re looking for a luxury vacation home, investment property, or a personal retreat, this rare offering delivers the best resort-style living just minutes from world-class attractions, dining, and entertainment. Sunset Walk is located within the resort and is filled with a ton of restaurants, a movie theater, live entertainment, and more. The resort also has H20 Waterpark and a ton of retail which is ALL walkable from this home. HOA and The Fins Up Club cover daily trash removal, internet, cable, phone, pest control, landscaping, free resort shuttle, shuttle to parks, resort pools, and fitness center.

3009 Sea Plane Lane, Kissimmee

$459,900
4 Beds 3 Baths Rolling Oaks Ph 5 SubDv. 34747 Zip Code
"LAZY PARROT" is a Charming Cottage at Margaritaville Resort Orlando. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Located in PREMIUM RESORT LOCATION Just a Short Walk to All the Amenities! MRO Approved City Furniture "SAIL AWAY" Furniture/Housewares Included in List Price. Beautiful 1539-C Model, 3 Bedrooms, 3 Bathrooms with BONUSROOM and CUSTOM PARROT DESIGN SHUTTERS. Master Suites on BOTH First and Second Floors. Downstairs Suite has French Doors Leading to Tranquil Backyard with Paved Patio, Beautiful Tropical Foliage and Shell Pathways. All Three Bedrooms have KING BEDS! The Furniture is the Original City Furniture MRO Approved and Some Items are No Longer Available to Purchase. Home Features High Capacity Washer and Dryer, "SON OF A SAILOR" Interior Upgrade with "WOOD" Tile Flooring, Upgraded Appliances, QUARTZ Countertops, Ceiling Fans and TANKLESS WATER HEATER. There is an Additional Bonus Room Upstairs with a BUILT IN TWIN BED and TV. Furniture/Housewares Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishwasher, Linens, and so MUCH MORE! This Unique First of its Kind Resort has Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail and More! LOCATED MINUTES FROM DISNEY PARKS!, All While Being Conveniently Close To The Best Shopping, Dining, and Entertainment Options In Florida. This Home Is Not Just A Residence; It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation.

8080 Dreamsicle Drive, Kissimmee

$1,375,000
8 Beds 9 Baths Rolling Oaks Ph 5 SubDv. 34747 Zip Code
'EASY BREEZY' Cottage on Margaritaville Resort Orlando's 'TROPHY ROW'! EXTREMELY RARE OPPORTUNITY TO OWN ONE of the LARGEST WATERFRONT COTTAGES WITH POOL and SPA Plus Your Very Own ELEVATOR ($40k Upgrade)! Home is FULLY HANDICAP ACCESSIBLE. 4131-A Model, 8 Bedrooms, 8 Full Bathrooms and 1 Half Bathroom with IN PARADISE Upgrade. This Amazing Home Features One En Suite Bedroom on First Floor Along with Another Bedroom with Hallway Bath, Large Kitchen with Tiled Backsplash and Breakfast Bar, Spacious Pantry with CUSTOM SHELVING, Living Room with Sliders that Lead to Beautiful Paved Patio, Fenced In Backyard has Covered Area, Cabana Bath, Outdoor Speakers and TV Hookup, In-Ground Pool and Spa with Custom Safety Handrails and Spectacular SUNSET VIEWS Over the Pond! Second Floor has Primary Suite with Separate Tub and Shower, CUSTOM BUILT CLOSET and Access to Balcony Overlooking Backyard. Three En Suite Bedrooms Complete Second Floor with Hallway Access to the Large Front Balcony. Third Floor has Upgraded Mosaic Tiled Alcoves which Compliment the Stairs leading to a Suite with Separate Tub and Shower, Access to Huge Tiled and COVERED PARTY DECK with Sweeping Lake Views. Loft with Wet Bar is Next to the Eighth Bedroom with Full Bathroom. Home also has Covered Front Porch, Upgraded 'Wood' Tile Flooring, Quartz Countertops. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail and More! LOCATED MINUTES FROM DISNEY PARKS! There's Nothing Like Living the Margaritaville Lifestyle in Paradise!

3056 Parrot Head Place, Kissimmee

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