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, an enchanting subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This exquisite community offers a perfect blend of tranquility and modern living, making it an ideal choice for families and individuals seeking a serene lifestyle.

Rolling Oaks Phase 5 is a gated community, providing residents with the peace of mind that comes from living in a secure environment. With 24/7 guard services, you can rest easy knowing that your safety is a top priority. The beautifully landscaped surroundings and well-maintained entrance create an inviting atmosphere that welcomes you home.

The homes in this charming subdivision are designed with comfort and style in mind. From spacious layouts to modern finishes, Rolling Oaks Phase 5 boasts a variety of architectural styles that cater to diverse tastes. Whether you're looking for a cozy single-family home or a more expansive residence, you’ll find options that suit your lifestyle perfectly.

Beyond the gates, residents can enjoy a wealth of amenities and recreational opportunities. The community is conveniently located near shopping centers, dining options, and top-rated schools, ensuring that everything you need is just a stone's throw away. Additionally, the nearby parks and nature trails provide ample opportunities for outdoor activities, making it easy to embrace the Florida sunshine.

Experience the charm and security of Rolling Oaks Phase 5, where your dream home awaits in a vibrant community that feels like a retreat. Come explore this hidden gem in Kissimmee and discover the perfect place to create lasting memories!

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

$470,000
4 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
'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
$425,000
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
$394,999
2 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
YOUR PRIVATE PIECE OF PARADISE IN MARGARITAVILLE! Fully furnished, beautifully upgraded, and complete with your own private hot tub, 3009 Sea Plane Lane is the Margaritaville vacation home you've been waiting for! This stunning 2-bedroom, 2.5-bath cottage combines the carefree Margaritaville lifestyle with thoughtful upgrades, beautiful furnishings and a private outdoor retreat. From the moment you walk in, you'll notice the difference. This home features the Ethan Allen furniture package, wood-look ceramic tile flooring, high ceilings, upgraded lighting, and a beautifully designed kitchen with custom backsplash and island details, plus convenient over- and under-cabinet lighting. The open-concept living area is made for relaxing and entertaining, featuring in-ceiling speakers, a Klipsch soundbar, Samsung Frame TV and a queen sleeper sofa for additional guests. The home is being offered fully furnished, making it truly turnkey for your next vacation getaway, second home or investment property. Step through the kitchen and into your private backyard oasis! The spacious paver patio features a personal hot tub, lounge chairs and lush tropical landscaping, creating a peaceful and private space to unwind after a day at the parks or enjoy an evening under the Florida sky. Upstairs, you'll find two comfortable bedrooms and two full bathrooms, providing plenty of privacy for owners and guests. The thoughtful layout makes this home equally appealing for personal use or vacation rental opportunities. And then there's the location! You are inside Margaritaville Resort Orlando, surrounded by everything that makes this community one of Central Florida's most sought-after vacation destinations. Sunset Walk is right within the resort, offering restaurants, bars, live entertainment, shopping and a movie theater. Island H2O Water Park is also walkable, while Disney, Universal and Orlando's world-famous attractions are just minutes away. Resort amenities include multiple pools, fitness facilities, dog park, resort transportation and shuttle service to the theme parks. The HOA/Fins Up Club also includes services such as internet, cable, phone, landscaping, pest control and daily trash removal, making ownership incredibly convenient. Whether you're looking for a luxury vacation home, a second home, a full-time Florida residence or a vacation rental investment, this turnkey Margaritaville cottage gives you the opportunity to own the lifestyle everyone comes to Central Florida to enjoy. Private hot tub. Designer furnishings. Resort amenities. Sunset Walk. Theme parks. Margaritaville. Come see why life really is better in Margaritaville! Schedule your private showing today.

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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