Rolling Oaks Ph 5 Real Estate

Rolling Oaks Ph 5 Real Estate

Welcome to Rolling Oaks Phase 5, a picturesque subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This charming community offers a harmonious blend of suburban tranquility and modern convenience, making it the perfect place for families, retirees, and anyone seeking a serene lifestyle close to the excitement of Central Florida.

Rolling Oaks Phase 5 features beautifully designed homes that cater to a variety of tastes and lifestyles. From spacious single-family residences to cozy townhomes, each property is crafted with quality and comfort in mind. The lush landscaping and well-maintained streets create an inviting atmosphere that residents are proud to call home.

One of the standout features of Rolling Oaks is its prime location. Just minutes away from the world-renowned attractions of Walt Disney World and Universal Studios, residents can easily enjoy the magic of theme parks while also relishing the peaceful retreat of their neighborhood. Additionally, the subdivision is conveniently situated near major highways, shopping centers, and dining options, ensuring that everything you need is within reach.

For outdoor enthusiasts, Rolling Oaks Phase 5 boasts proximity to beautiful parks and recreational areas, perfect for hiking, biking, or simply enjoying Florida's sunshine. With a strong sense of community and friendly neighbors, this subdivision is not just a place to live, but a place to thrive.

Discover the charm and convenience of Rolling Oaks Phase 5, where your dream home awaits in the enchanting city of Kissimmee!

Newest Listings in Rolling Oaks Ph 5

$525,000
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
$329,900
1 Beds ⋅ 1 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
SELLER MOTIVATED - CALL FOR YOUR PRIVATE SHOWING TODAY! LOCATION! LOCATION! LOCATION! This spectacular, FULLY FURNISHED home is not only centrally located and with in 20 mins of all Disney Parks, but it is also perfectly located within the resort, just feet away from the amenitities including the pool, spa abd fitness center. It features tile flooring and ceiling fans throughout. It is a 1 story, 1 bedroom and 1 bath fully furnished cottage, beautifully themed, bright and colorfully decorated. The kitchen opens seamlessly to the main living area, making it perfect for entertaining or vacation hosting. The back patio includes a table and 4 chairs as well as 2 sun loungers, Margaritaville is a pet-friendly community, which also features Barkaritaville, a great dog park. The monthly HOA covers high-speed internet, cable, phone, daily doorstep garbage pickup, professional landscaping, and pest control. The Fins UP Beach Club gives you access to enjoy full access to world-class resort amenities including 7 resort pools, a fitness center/gym, an internal resort shuttle, and free transportation shuttles directly to the local theme parks. This unique resort setup is highly walkable, situated just steps from Island H2O Water Park and Sunset Walk’s vibrant mix of restaurants, bars, live music, Target, Ulta and more. Centrally located with lightning-fast access to Disney, Universal, SeaWorld, and Gatorland, this property is a premier choice for a primary residence, second home, or lucrative vacation investment.

3054 Pirate Way, 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
$390,000
2 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
Welcome to 8056 Dreamsicle Drive in Kissimmee, a beautifully maintained 2 bedroom, 2 1/2 bathroom home located in the highly sought-after Margaritaville Resort Orlando community. This charming two-story home features inviting coastal architecture, bright interior spaces, and a functional layout designed for both comfortable living and successful vacation rental potential. The exterior showcases a picturesque front porch and balcony along with tropical landscaping that complements the vibrant resort-style surroundings. Inside, the home offers an open-concept living area filled with natural light, tile flooring throughout the main living spaces, and modern finishes. The spacious kitchen features quartz countertops, stainless steel appliances, abundant cabinetry, and a convenient breakfast bar perfect for entertaining or casual dining. The adjoining living and dining areas create a welcoming space to relax or host guests. Each of the three bedrooms provides comfort and privacy, while the three full bathrooms provide updated fixtures and ample space for residents and visitors alike. The rear of the home features a private patio area ideal for outdoor seating, relaxation, or enjoying Florida’s warm weather. Located within the world-renowned Margaritaville Resort Orlando, residents and guests enjoy access to exceptional resort-style amenities including multiple swimming pools, a fitness center, spa services, water park access, and beautifully maintained walking paths. Just a short stroll away is the vibrant Sunset Walk entertainment district offering a variety of restaurants, live music venues, boutique shopping, and family-friendly attractions. Popular dining options nearby include Ford’s Garage, Estefan Kitchen, Rock & Brews, and multiple casual waterfront-style eateries perfect for enjoying the Florida lifestyle. This property offers an unbeatable location just minutes from Walt Disney World Resort, including Magic Kingdom, EPCOT, Hollywood Studios, and Animal Kingdom. Other major attractions such as Universal Orlando Resort, SeaWorld Orlando, and ICON Park are also easily accessible. For shopping enthusiasts, nearby options include Orlando Vineland Premium Outlets, The Mall at Millenia, and a wide variety of retail stores along US-192 and nearby ChampionsGate. Travel convenience is another advantage, with Orlando International Airport approximately 30 minutes away and Orlando Sanford International Airport about 50 minutes away, making travel simple for both homeowners and visiting guests. The home is also located near several medical facilities including AdventHealth Celebration Hospital, Orlando Health Horizon West Hospital, and HCA Florida Osceola Hospital, providing excellent healthcare access. With its prime location near world-class attractions, resort amenities, entertainment, dining, shopping, and major travel routes, 8056 Dreamsicle Drive offers an exceptional opportunity whether you are seeking a vacation home, investment property, or primary residence in one of Central Florida’s most desirable resort communities.

8056 Dreamsicle Drive, Kissimmee
$1,275,000
7 Beds ⋅ 9 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
**7 Bedrooms | 8.5 Bathrooms | Waterfront Living at Its Finest** ENJOY DISNEY MAGIC KINGDOM AND EPCOT FIREWORKS FROM THE TOP DECK. Welcome to your dream home on the lake! This stunning 7-bedroom, 8.5-bathroom house just hit the market and it's everything you've been looking for. Sitting right on the water, you'll enjoy gorgeous sunsets from your backyard every single evening. No hauling suitcases up the stairs here — this home comes with its own elevator! Three balconies give you plenty of outdoor space to relax, and one of the balconies even has a TV and overlooks the lake. Talk about the perfect spot to unwind. Inside, you'll find beautiful tile flooring throughout, quartz countertops, solid wood cabinets, and stainless steel appliances in the kitchen. Every bedroom is generously sized with a private bath, giving everyone plenty of room to spread out. The large game room with a wet bar with a pool table is ideal for entertaining guests. Step outside to your private pool and spa, where lakefront views make every swim feel like a vacation. The sunsets from this property are truly something special. Location is a huge bonus here. You're just minutes from Walt Disney World, Island H2O Waterpark, Sunset Walk, and plenty of shopping — including Target Grocery just down the road on Rolling Oaks Boulevard. Here's the best part — live here full-time as your forever home or rent it out on Airbnb for excellent rental income. Either way, this lakefront gem is a smart investment you don't want to miss!

8017 Surf Street, Kissimmee
$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
$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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