Rolling Oaks Real Estate

Rolling Oaks Real Estate

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of Florida, where the sun shines bright and the lifestyle is nothing short of idyllic. This charming community offers a perfect blend of serene suburban living and convenient access to vibrant city life, making it an ideal choice for families, retirees, and everyone in between.

Rolling Oaks boasts beautifully landscaped streets lined with majestic oak trees, creating a tranquil atmosphere that invites you to unwind and enjoy nature. The homes here are a delightful mix of modern designs and classic architecture, each with spacious yards that provide ample room for outdoor activities and gatherings with friends and family.

Residents of Rolling Oaks enjoy a wealth of amenities, including well-maintained parks, walking trails, and recreational facilities that encourage an active lifestyle. Families will appreciate the proximity to highly rated schools, ensuring an excellent education for children of all ages. Additionally, the community is conveniently located near shopping centers, restaurants, and entertainment options, making everyday errands a breeze.

For those who love the outdoors, Rolling Oaks is just a short drive away from Florida’s stunning beaches and lush nature reserves, perfect for weekend getaways or leisurely afternoons spent soaking up the sun. With its friendly atmosphere, strong sense of community, and beautiful surroundings, Rolling Oaks is more than just a place to live; it’s a place to call home.

Discover the charm of Rolling Oaks today, and experience the perfect blend of comfort, convenience, and community in sunny Florida!

Newest Listings in Rolling Oaks

$1,375,000
A12084469 MLS
VACANT LOT | BRING YOUR OFFERS! Right-sized and right-priced, this 2.8-acre parcel offers an accessible opportunity to create your own ranch retreat in the highly desirable Rolling Oaks community of Southwest Ranches. Lush, private, and full of character, the property fronts SW 178th Avenue and is surrounded by many beautiful recently built estates in the area. A breathtaking, grand-scale mature tree already anchors the entrance, creating an exceptional natural focal point and a memorable sense of arrival, as shown in the images. The canal traversing the site creates a distinctive configuration and influences the available building areas, while also providing tranquil water views and an appealing rustic setting. With thoughtful planning, the property presents the exciting possibility of combining a contemporary ranch residence, outdoor living spaces, equestrian amenities or even a sizeable car barn, studio or detached gym facility. The listing renderings illustrate one potential vision for transforming this unique parcel into a charming South Florida ranch lifestyle. Conveniently located with excellent accessibility and offered at a compelling value for the area. Conceptual RENDERINGS are for illustrative purposes ONLY. Buyers should independently verify zoning, setbacks, permitting requirements, and development feasibility.

4800 SW 178th Avenue, Southwest Ranches
$1,375,000
A12084490 MLS
VACANT LOT | BRING YOUR OFFERS! Right-sized and right-priced, this 2.8-acre parcel offers an accessible opportunity to create your own ranch retreat in the highly desirable Rolling Oaks community of Southwest Ranches. Lush, private, and full of character, the property fronts SW 178th Avenue and is surrounded by many beautiful recently built estates in the area. A breathtaking, grand-scale mature tree already anchors the entrance, creating an exceptional natural focal point and a memorable sense of arrival, as shown in the images. The canal traversing the site creates a distinctive configuration and influences the available building areas, while also providing tranquil water views and an appealing rustic setting. With thoughtful planning, the property presents the exciting possibility of combining a contemporary ranch residence, outdoor living spaces, equestrian amenities or even a sizeable car barn, studio or detached gym facility. The listing renderings illustrate one potential vision for transforming this unique parcel into a charming South Florida ranch lifestyle. Conveniently located with excellent accessibility and offered at a compelling value for the area. Conceptual RENDERINGS are for illustrative purposes ONLY. Buyers should independently verify zoning, setbacks, permitting requirements, and development feasibility.

4800 SW 178th Avenue, Southwest Ranches
$615,000
3 Beds ⋅ 2 Baths ⋅ A12053754 MLS ⋅ Margaritaville BLDG.
**Rare waterfront cottage in Margaritaville Resort Orlando!** One of the few cottages with a premium direct waterfront location, this beautiful 3-bedroom, 2-bath home offers breathtaking water views from two private balconies.**Unlike heavily rented vacation homes, this residence has been privately enjoyed and carefully maintained**, giving it a like-new feel without the wear and tear often associated with short-term rentals. While never enrolled in a rental program, it is fully eligible for short-term rental, making it an excellent primary residence, vacation home, or investment opportunity.The home features tile flooring throughout, an open-concept floor plan, a durable metal roof, quartz countertops, stainless steel appliances, and beautifully designed living spaces with tasteful coastal décor. The spacious kitchen flows seamlessly into the living and dining areas, creating the perfect setting for entertaining.Enjoy peaceful water views, morning coffee, or spectacular Florida sunsets from either of the two private balconies.Margaritaville Resort Orlando offers resort-style amenities including multiple pools, a fitness center, Island H2O Water Park, shopping, dining, live entertainment, and the Promenade at Sunset Walk. Located just minutes from Walt Disney World and Orlando's major attractions, this rare waterfront property is an exceptional opportunity to own one of Margaritaville's most desirable cottages. **Rare waterfront cottage in Margaritaville Resort Orlando!** One of the few cottages in the community with a premium direct waterfront location, this beautiful 3-bedroom, 2-bath home offers breathtaking water views from both private balconies and a lifestyle unlike any other. **Unlike heavily rented vacation homes, this residence has been privately enjoyed and carefully maintained**, giving it a like-new feel without the wear and tear often associated with short-term rental properties. Whether you're looking for a primary residence, vacation home, or investment property, this home is eligible for short-term rentals and can easily be placed into the resort's rental program if desired. Inside, you'll find numerous upgrades, including tile flooring throughout, an open-concept floor plan, a durable metal roof, quartz countertops, stainless steel appliances, and beautifully designed living spaces that are both stylish and functional. The thoughtfully selected coastal décor perfectly complements the home's character and inviting atmosphere. The spacious kitchen opens seamlessly to the living and dining areas, creating the perfect space for entertaining family and friends. One of the home's most desirable features is its two private waterfront balconies—one on each level—where you can enjoy peaceful water views, your morning coffee, or spectacular Florida sunsets. Margaritaville Resort Orlando offers an exceptional resort lifestyle with multiple resort pools, a fitness center, live entertainment, shopping, dining, Island H2O Water Park, and the vibrant Promenade at Sunset Walk featuring restaurants, bars, boutiques, and year-round entertainment. Located just minutes from Walt Disney World and Orlando's other world-famous attractions, this rare waterfront property offers an outstanding opportunity as a primary residence, second home, or income-producing investment.

8117 Surf Street, Kissimmee
$2,600,000
4 Beds ⋅ 3 Baths ⋅ A12047272 MLS ⋅ Rolling Oaks BLDG.
Opportunity to live on this spectacular fenced-in corner lot parcel in Southwest Ranches. 4 bedroom + office, 3 bathroom estate offers the perfect blend of country living and modern comfort with a split floor-bedroom plan. Elegant spaces with formal living, dining and family rooms with large windows and French doors overlooking the backyard. Spacious kitchen features distressed white wood cabinetry, stainless steel appliances, wine cooler, granite counters, island, coffee-bar area, countertop seating and breakfast nook. Primary suite offers a spa-like bathroom with a jetted tub, double vanities, step in shower and walk-in closets. Impact glass, central vacuum system, Tesla EV charger and 2 car garage. Outside you will find an incredible outdoor living area featuring a covered patio, summer kitchen, refreshing pool and spa, and lush tropical landscaping designed for relaxing and entertaining. Beyond the backyard, the expansive grounds continue with a 6 stall horse barn, paddock riding area, chicken coop and plenty of room for horses and other farm animals. Whether you are an equestrian, hobby farmer or simply looking for privacy and open space, this exceptional property offers endless possibilities in one of South Florida's most renowned towns.

17710 SW 63rd Manor, Southwest Ranches
$375,000
3 Beds ⋅ 3 Baths ⋅ A11899936 MLS
Calling all investors: This unit is already generating income!! Turnkey, fully furnished 3BR/3 BA townhome in highly desirable Margaritaville Resort Orlando. Located just minutes from Disney, this property is already operating as a successful short-term rental with management in place or option to self-manage. Features include an open floor plan, 1 FULL BED & BATH on 1ST FLOOR, quartz countertops, tile flooring, and included linens, housewares, and decor. Resort amenities include multiple pools, fitness center, spa, restaurants, live music, water park, and free shuttles to theme parks. HOA covers cable, internet, landscaping, daily trash pickup, pest control, and 24/7 security. Ideal as an investment property, vacation home, or primary residence in one of Orlandos top resort communities. .

2971 Castaway Lane, Kissimmee
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