Welcome to Feature Friday, where we shine a spotlight on hidden gems and high-demand communities that locals actually love to live in.
This week’s feature brings us to a community that blends timeless charm with modern comfort, nestled just minutes from the heart of Horizon West and the magic of Walt Disney World:
✨ Oakland Trails
Where front porch living, tree-lined streets, and access to nature create the kind of neighborhood that just feels right.
🏡 Where Is Oakland Trails?
Oakland Trails sits on the western edge of Winter Garden, bordering the quaint and historic town of Oakland, FL.
📍 Just off FL-50 and near the Florida Turnpike, it offers:
- 🚗 ~20–25 minutes to Disney property via SR-429
- 🚲 Direct access to the West Orange Trail—perfect for walking, biking, or even golf carts
- 🛍️ 10 minutes to downtown Winter Garden + Plant Street Market
- 🏫 Top-rated Orange County schools
You get the best of both worlds: peaceful, small-town vibes with quick connections to Orlando’s best amenities.
🛠️ What Makes Oakland Trails Unique?
Developed by M/I Homes, Oakland Trails was thoughtfully designed with community and sustainability in mind.
Expect:
- 🏠 Craftsman- and bungalow-style architecture with high curb appeal
- 🪟 Spacious front porches that encourage neighborly connection
- 🌳 Mature landscaping, tree-lined sidewalks, and plenty of green space
- 🏡 Floorplans from ~1,700–3,000+ sq ft
- 🔑 Smart-home features, energy-efficient designs, and quality craftsmanship
🏷️ Resale pricing currently ranges from the mid-$400Ks to $600Ks, depending on lot and upgrades…a solid value in today’s market given its location and community design.
🌿 The Lifestyle: Slower, Simpler, and More Connected
Oakland Trails was built for living, not just sleeping.
Here’s what makes everyday life special:
- 🛝 A beautiful central park with playground, green space, and dog park
- 🚴♀️ Direct access to 22+ miles of the West Orange Trail
- 🌞 Covered pavilions, BBQ areas, and gathering spots
- 🧘 Peaceful streets, friendly neighbors, and zero tourist traffic
- 🐾 Pet-friendly and perfect for families, professionals, or active retirees
This is one of those communities where everyone waves, kids ride their bikes, and neighbors look out for each other.
💬 What Residents Are Saying
“It’s the kind of place you move to for a quieter life…and realize how much you needed it.” – Kayla B.
“We wanted space and charm, but also to stay close to Disney. This was the answer.” – David & Sheree H.
“We ride our bikes to downtown Winter Garden and stop for coffee on the trail. It’s like living in a Hallmark movie.” – Felix R.
If you’ve been craving a place that feels a little more grounded, a little more human, and a whole lot more intentional…
Oakland Trails may be exactly where your next chapter belongs.
It’s not just about living near Disney.
It’s about living in a way that feels good every day of the week.
I’m Timothy Carter, your dedicated Disney World Orlando area relocation expert with The Funk Collection brokered by eXp Realty.
I specialize in helping Disney lovers & theme park enthusiasts find their perfect home or vacation investment property. I’m here to help turn your dreams into reality!
You’ll find everything you need to know about living in the greater Orlando area – from neighborhood guides, real estate tips & the lifestyle of living near the theme parks, to insider advice on relocating to this magical place.
My family moved to Orlando to LIVE the ultimate Disney lifestyle!
You can too! I can help! Click here —-> Meet With Timothy Carter
