Rolling Woods Real Estate

Welcome to Rolling Woods, a hidden gem nestled in the heart of Orlando, Florida, within the vibrant Orange County. This enchanting subdivision is known for its lush landscapes, serene atmosphere, and a strong sense of community, making it an ideal place for families, professionals, and retirees alike.

Rolling Woods boasts a variety of charming homes that cater to diverse tastes and lifestyles. From cozy single-family residences to spacious modern designs, there’s something for everyone in this picturesque neighborhood. The tree-lined streets are perfect for leisurely strolls, and the well-maintained yards add to the overall appeal of the area.

One of the standout features of Rolling Woods is its proximity to some of Orlando’s most sought-after amenities. Residents enjoy easy access to top-rated schools, parks, and recreational facilities, ensuring that families have everything they need within reach. The nearby shopping centers and dining options offer a delightful mix of local favorites and popular chains, providing a vibrant lifestyle just minutes from home.

Nature enthusiasts will appreciate the nearby parks and green spaces, perfect for weekend picnics, jogging, or simply soaking in the Florida sun. The community spirit in Rolling Woods is palpable, with neighborhood events and gatherings fostering connections among residents.

With its prime location, charming homes, and welcoming atmosphere, Rolling Woods is more than just a subdivision; it’s a community where memories are made and friendships flourish. Discover the magic of Rolling Woods and let it be the backdrop for your next chapter in Orlando.

Newest Listings in Rolling Woods

$374,900

3 Beds ⋅ 2 Baths ⋅ Rolling Woods SubDv. ⋅ 33813 Zip Code

Remodeled, move-in ready 3-bed, 2-bath home on a spacious 1/3-acre lot in a highly desirable South Lakeland neighborhood. Bright, open floor plan with abundant natural light, a large family room and eat-in kitchen, plus a moody den/office overlooking the expansive backyard. Luxury vinyl plank flooring flows through the main living areas; bedrooms feature newer carpeting. The updated kitchen showcases stainless steel appliances, quartz countertops, a striking tile backsplash, an island with extra seating, and a large walk-in pantry. The generous primary suite offers a walk-in closet and an ensuite with dual sinks and a walk-in shower. Additional highlights: central vacuum system, enclosed back porch with a charming wood ceiling, mature oak-shaded backyard, storage shed and attached 2-car garage. Recent upgrades include a roof (2017), HVAC (2025), stainless refrigerator (2025), and a new garage door (2024). Excellent location just off Cleveland Heights; close to shopping, the YMCA, parks, schools, Lake Hollingsworth, and Cleveland Heights Golf Course and tennis courts. Schedule your private showing today!

851 Rolling Woods Lane, Lakeland

$142,000

2 Beds ⋅ 1 Baths ⋅ Rolling Woods SubDv. ⋅ 32784 Zip Code

Concrete block home on a large lot in a quiet neighborhood. Come take a look at this two bedroom one bathroom home with mature landscaping. This home has updated kitchen appliances.

17247 Se 284th Terrace, Umatilla

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