Rolling Oaks Ph 5 Homes for Sale

Rolling Oaks Ph 5 Homes for Sale

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

Rolling Oaks Phase 5 boasts a variety of beautifully designed homes, each showcasing unique architectural styles and features that cater to diverse tastes. Whether you're searching for a cozy single-family home or a spacious residence perfect for entertaining, you're sure to find a property that meets your needs. The homes for sale in this inviting community are equipped with modern amenities, open floor plans, and lush outdoor spaces, allowing residents to enjoy the best of Florida living.

Beyond the beautiful homes, Rolling Oaks Phase 5 is strategically located near major highways, making it easy to access local attractions, shopping centers, and dining options. Families will appreciate the proximity to top-rated schools and parks, ensuring that children have plenty of opportunities for education and recreation.

Embrace the warm Florida sunshine and the friendly atmosphere of Rolling Oaks Phase 5, where neighbors become friends and memories are made. With homes for sale, now is the perfect time to explore this charming subdivision and discover your dream home in Kissimmee. Don't miss out on the chance to be part of this thriving community—your new beginning awaits!

Newest Rolling Oaks Ph 5 Homes for Sale

8028 Dreamsicle Drive, Kissimmee
$399,000
2 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
BEAUTIFUL and SPACIOUS Cottage For Sale with 2 Bedrooms, 2.5 Bathrooms and a HOT TUB at Margaritaville Resort Orlando! Located in a PREMIUM RESORT LOCATION, Close to the Pedestrian Bridge and just a Short Walk to the Resort Amenities! This HOME IS RENT READY. MRO Approved City Furniture/Housewares Package is INCLUDED IN LIST PRICE! The home features "IN PARADISE" Interior Upgrades, QUARTZ Countertops, Ceiling Fans, Upgraded Appliances, High Ceilings, 'WOOD' Tile Flooring Throughout, TANKLESS WATER HEATER, HIGH CAPACITY Washer and Dryer and a Large Backyard with Paved Patio and Tropical Foliage. Upstairs You Will Find Two En Suite Bedrooms. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! List Price INCLUDES Furniture/Housewares with Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation!

8028 Dreamsicle Drive, Kissimmee
8036 Surf Street, Kissimmee
$470,000
4 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
BEST PARKVIEW BACKYARD IN THE ENTIRE RESORT WITH GRASS! NOTHING ELSE COMPARES! 'PIRATES IN PARROTDISE' Cottage at Margaritaville Resort Orlando! Spacious Model 1384-C with 3 Bedrooms, 3 Bathrooms and an ADDITIONAL BONUS BEDROOM, BACK PATIO RETRACTABLE AWNING and a HOT TUB! Premium Location Near the Pedestrian Bridge! Spacious Living Room has a HUGE 75-INCH TV. IMMACULATE CONDITION ~ WELL MAINTAINED HOME. This home has NEVER been an STR and has been used as a SECOND HOME and LONG-TERM RENTAL most recently. First Floor Bedroom has En-Suite Bathroom and French Doors Leading to Spacious Backyard Patio with a Gorgeous GRASSY Backyard and TIKI HUTS. Second Floor has Primary En-Suite Bedroom with Front Balcony Access. Bonus Room has been Converted to a Bunk Room. The Kitchen features Upgraded Appliances, and Quartz Countertops. This Home also features Tile Flooring, Ceiling Fans Throughout, Washer and Dryer, Landscaping has Beautiful Foliage! All Furniture, Linens, Housewares and Decor INCLUDED IN LIST PRICE! Includes HIGH END ETHAN ALLEN FURNISHINGS, Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail and More! This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! LOCATED MINUTES FROM DISNEY PARKS! Come Enjoy the Margaritaville Lifestyle in Paradise!

8036 Surf Street, Kissimmee
8060 Dreamsicle Drive, Kissimmee
$399,900
3 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
YOUR ORLANDO VACATION HOME IS READY—JUST BRING YOUR SUITCASE! Fully furnished and turnkey inside Margaritaville Resort Orlando, this 3-bedroom + BONUS ROOM, 3-bath cottage delivers the resort lifestyle buyers dream about just minutes from Walt Disney World. A desirable CORNER LOCATION and DUAL PRIMARY SUITES one upstairs and one downstairs, create exceptional flexibility for owners, families, and vacationing guests. Inside, soaring ceilings and abundant natural light complement the open-concept design, quartz countertops, stainless steel appliances, upgraded cabinetry, and signature “Son of a Sailor” interior package. Step outside to your private tropical retreat featuring a paved patio and HEATED HOT TUB, the perfect ending to a day at the parks.Best of all, it’s FULLY FURNISHED, including furniture, TVs, décor, linens, kitchen essentials, housewares, and more. Enjoy it immediately as your Florida getaway, second home, or SHORT-TERM RENTAL opportunity. Walk to Margaritaville resort amenities and enjoy nearby Sunset Walk dining, shopping, entertainment, and live music. Minutes from Disney, Universal Orlando, Epic Universe, golf, and Central Florida attractions. Don’t just visit paradise...OWN IT.

8060 Dreamsicle Drive, Kissimmee
3054 Pirate Way, Kissimmee
$299,999
1 Beds ⋅ 1 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
Welcome to Pirate Way — a beautifully furnished, fun 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
8056 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
8017 Surf Street, 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
3052 Parrot Head Place, 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
3056 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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