Rolling Oaks Ph 5 Homes with Sidewalk Exterior Features

Rolling Oaks Ph 5 Homes with Sidewalk Exterior Features

Welcome to Rolling Oaks Phase 5, a delightful subdivision nestled in the heart of Kissimmee, Florida, within beautiful Osceola County. This charming community is designed for those who appreciate the perfect blend of comfort, convenience, and a vibrant lifestyle. With its meticulously planned layout and picturesque surroundings, Rolling Oaks Phase 5 is the ideal place to call home.

One of the standout features of this community is its commitment to connectivity and outdoor living. Homes in Rolling Oaks Phase 5 boast inviting sidewalks that meander through the neighborhood, encouraging residents to take leisurely strolls, enjoy morning jogs, or simply connect with neighbors. The picturesque streets are lined with lush landscaping, creating a serene atmosphere that enhances the overall charm of the area.

The homes in this subdivision are thoughtfully designed, offering a variety of layouts to suit diverse lifestyles. Whether you’re a growing family, a first-time homebuyer, or looking to downsize, you’ll find a perfect fit here. Each residence is crafted with attention to detail, featuring modern amenities and spacious interiors that promote both comfort and functionality.

Living in Rolling Oaks Phase 5 means you’re conveniently located near a wealth of shopping, dining, and recreational options. With easy access to major highways, you’re just a short drive away from the attractions of Orlando, making this community a prime choice for those who enjoy a blend of suburban tranquility and urban excitement.

Discover the charm of Rolling Oaks Phase 5 and envision your new life in this vibrant Kissimmee community!

Newest Rolling Oaks Ph 5 Homes with Sidewalk Exterior 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
$465,000
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
$315,000
1 Beds ⋅ 1 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
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
$1,375,000
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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