Rolling Oaks Real Estate

Rolling Oaks Real Estate

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of Florida, where serene landscapes meet modern living. This charming community is designed for those who appreciate the beauty of nature while enjoying the conveniences of contemporary life.

Rolling Oaks is renowned for its lush, mature oak trees that line the streets, creating a tranquil and inviting atmosphere. The subdivision boasts a variety of well-crafted homes, each showcasing unique architectural styles that cater to diverse tastes. Whether you’re seeking a cozy single-family home or a spacious residence for your growing family, Rolling Oaks has something to offer everyone.

One of the standout features of this community is its commitment to outdoor living. Residents can take advantage of beautifully landscaped parks, walking trails, and picnic areas, perfect for family gatherings or a peaceful afternoon stroll. The neighborhood's design encourages a strong sense of community, where neighbors become friends and children can play safely outside.

Conveniently located, Rolling Oaks provides easy access to major highways, making commuting a breeze. You’ll find an array of shopping, dining, and entertainment options just a short drive away, along with top-rated schools that cater to families.

For those who love the great outdoors, nearby attractions include stunning beaches, nature reserves, and recreational areas, all within a short distance.

Embrace the charm and warmth of Rolling Oaks, where community spirit thrives and the beauty of Florida living awaits you. Come discover your dream home in this idyllic subdivision today!

Newest Listings in Rolling Oaks

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

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

Prime residential land opportunity in the sought-after town of Southwest Ranches, FL. This corner lot, facing 178 Ave, offers a rare chance to build your dream home in a rapidly developing area. Surrounded by new, upscale residences, this property presents an ideal canvas for a custom-built home. The spacious lot provides ample room for a variety of architectural styles and outdoor amenities. Take advantage of this rare offering to create a personalized oasis in a thriving community

4800 SW 178 Avenue, Southwest Ranches

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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Keisha Weir

I’m not just a real estate agent, I’m your trusted advisor, your advocate, and your go-to expert for turning property goals into reality. I bring unmatched dedication, market knowledge, and a personal touch to every client I serve because I know that real estate is more than a transaction , it’s about building a legacy and creating a lifestyle.I specialize in South Florida’s most desirable homes, offering white-glove service with deep local insight, strong negotiation skills, and a keen eye for design. Whether you’re buying your first home, selling a high-end property, or investing for the future, I tailor every step of the process to your vision , making it seamless, informed, and empowering.Let’s find the space where your next chapter begins.

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