Rolling Woods Homes for Sale

Welcome to Rolling Woods, a hidden gem nestled in the heart of Orlando, Florida. This charming subdivision offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, young professionals, and retirees alike. With its lush greenery and beautifully manicured landscapes, Rolling Woods provides a serene escape from the hustle and bustle of city life while still being just a stone’s throw away from Orlando’s vibrant attractions.

As you stroll through the tree-lined streets of Rolling Woods, you’ll find a diverse selection of homes for sale that cater to various tastes and lifestyles. From spacious single-family residences to cozy townhomes, there’s something for everyone in this welcoming community. Many of the homes feature modern amenities, open floor plans, and private outdoor spaces, perfect for entertaining or simply enjoying the Florida sunshine.

Residents of Rolling Woods enjoy easy access to top-rated schools, shopping centers, and recreational facilities, ensuring that everything you need is within reach. The community is also conveniently located near major highways, making commutes to downtown Orlando and surrounding areas a breeze.

Whether you’re looking to invest in your first home or searching for the perfect place to settle down, Rolling Woods presents an exceptional opportunity to embrace a vibrant lifestyle in one of Florida’s most sought-after cities. Explore the homes for sale in Rolling Woods today and discover the perfect backdrop for your next chapter!

Newest Rolling Woods Homes for Sale

$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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