If you’ve been dreaming of a home that combines resort-style amenities, golf course views, and a family-friendly atmosphere, Winston Trails in Lake Worth, FL, is your perfect match. As a gated golf community with nearly 1,900 homes spread across 20 villages, Winston Trails offers a rare blend of tranquility, convenience, and active living.

What’s It Like Living in Winston Trails?

When you pass through the secure gates of Winston Trails, the world seems to slow down. Palm-lined streets, shimmering lakes, and neighbors out for evening walks set the tone for this peaceful yet vibrant community. Whether you’re a retiree seeking a low-maintenance villa, a growing family in need of space, or a golf enthusiast ready to live steps from the fairway — Winston Trails has something for everyone.

Community highlights:

• 18-hole Winston Trails Golf Club (semi-private, no mandatory membership)

• Two resort-style pools & modern fitness center

• Lighted tennis courts & basketball courts

• Children’s playgrounds & walking trails

• 24-hour gated security for peace of mind

Real Estate Market Trends in Winston Trails

Median Sale Price: ~$610,000 (July 2025) — down 8.3% YoY
Median Listing Price: ~$649,500 — stable YoY
Active Listings Range: $399,900 – $859,000
Average Price per Sq Ft: ~$307 (active listings)

Over the past 6 months, Winston Trails has seen a 23% increase in homes sold, signaling strong buyer interest despite slight pricing dips. Homes here sell in 73 days on average, with golf course and lake view properties moving the fastest.

Simon’s insight: “Today’s market gives buyers an edge to negotiate — especially if you’re ready to move fast on the right home. For sellers, updated finishes and smart pricing will attract motivated buyers quickly.”

Top 3 Restaurants Near Winston Trails

Chris’ Taverna

Simon’s take: “The lemon chicken soup here is comfort in a bowl — perfect after a long day of showings.”

Park Avenue BBQ Grille 

Simon’s take: “Rib combo platter… my Friday night guilty pleasure.”

Sushi Yama Siam

Simon’s take: “Spicy tuna roll + Panang curry = unbeatable combo.”

Top 3 Parks Near Winston Trails

John Prince Park

Simon’s take: “Weekend recharge spot with unbeatable lake views.”

Okeeheelee Park

Simon’s take: “The kids love the playground — I love the kayaking.”

Freedom Park

Simon’s take: “My quick escape for coffee and quiet.”

Top 3 Local Shops Near Winston Trails

The Gardens Mall 

Worth Avenue

Simon’s take: “I bring out-of-town clients here when I want them to fall in love with the Palm Beach lifestyle — it works every time.”

Palm Beach Outlets

Simon’s take: “I’ve scored some incredible finds here — it’s my go-to for surprise gifts and last-minute client baskets.”

Zoned Schools for Winston Trails

• Manatee Elementary (PK–5) – 7–8/10 rating, strong academics, STEM & arts programs.

• Christa McAuliffe Middle (6–8) – Gifted & STEM tracks, robotics & coding clubs.

• Park Vista High (9–12) – A– rated, AP courses, dual enrollment, engineering academy.

Simon’s take: “Families move here for the schools as much as the homes — it’s a smart long-term investment.”

If you want to learn more about our communities then visit:

1. Villages of Windsor
2. Savannah Estates