From Orange Groves to Orlando's Hottest Market

I went to high school in Winter Garden. Back then, if you’d told me that our sleepy little citrus town would become one of Florida’s most desirable housing markets, I would have laughed. Downtown Plant Street was practically a ghost town. The area south of town? Nothing but orange groves as far as you could see.

Fast forward to today, and Winter Garden has become the #1 destination in Central Florida for families, young professionals, and transplants from across the country. The transformation has been nothing short of remarkable, and my family’s home value tells the story better than anything else: we haven’t done a single renovation, yet our home has tripled in value.

The Ghost Town That Came Back to Life

Remember when downtown Winter Garden was empty storefronts and cracked sidewalks? Those brick-lined streets felt frozen in time, but not in a charming way. Now, historic Plant Street is the crown jewel of West Orange County. The farmer’s market draws thousands every Saturday. Boutique shops, breweries, and restaurants have breathed new life into those beautiful old buildings.

The West Orange Trail transformed us into a “Trail Town” destination, and suddenly people from across Central Florida were discovering what we’d always had. They just needed a reason to visit.

The 429 Changed Everything

When State Road 429 opened through the area, it was like someone flipped a switch. Suddenly, Winter Garden wasn’t isolated anymore. You could reach downtown Orlando in 20 minutes, Disney in 15, the airport in 30. That connectivity unlocked everything.

And those orange groves I used to drive past on my way to school? They’re now Horizon West, a 30-square-mile master-planned region with five complete villages, A-rated schools, and over 58,000 residents. The population grew by more than 300% in just over a decade. Where there used to be cattle and citrus, there are now communities like Summerlake, Waterleigh, and Lakeshore, each with resort-style amenities, community pools, and modern homes.

The Numbers Don’t Lie

The Winter Garden housing market has been on fire.

Home values have approximately doubled over the past five years, with cumulative appreciation around 84%. The median home price reached $570,000 by late 2025, up from prices that seem almost quaint looking back at 2019.

My family’s experience is typical: homes that haven’t been touched are worth triple what they were worth a decade ago. Over the last 10 years, Winter Garden home values rose about 162%, putting us in the top tier nationally for appreciation.

Even during the 2023-2024 market cooldown when other areas struggled, Winter Garden held strong. Our annual appreciation rate outperformed 70% of other Florida cities.

Two Winter Gardens, One Hot Market

What makes Winter Garden unique is that we’re really two markets in one.

Historic Downtown Winter Garden retains its old Florida charm with restored bungalows, Victorian homes, brick streets, and that irreplaceable character. Buyers here want walkability, history, and community connection. Properties are scarce, which keeps values high and competition fierce.

Horizon West/Hamlin offers the opposite appeal: brand-new construction, master-planned communities, modern amenities, and family-friendly infrastructure. The Hamlin Town Center alone features over 2 million square feet of retail, dining, and entertainment, anchored by everything from a luxury Cinepolis theater to Orlando Health’s Horizon West Hospital.

Both markets are thriving. Buyers in their 30s and 40s with families gravitate south to the new developments. Empty-nesters, young professionals, and those who value historic character stay close to downtown.

Why Everyone’s Moving Here

Winter Garden consistently ranks among Florida’s hottest housing markets, and it’s easy to see why.

Location. Close enough to Orlando’s job centers and theme parks, far enough to feel suburban.

Schools. Nearly every Horizon West village has its own A-rated elementary or middle school.

Lifestyle. You get both historic downtown charm and modern convenience.

Value. Compared to older Orlando neighborhoods, buyers get more house for their money.

Growth. Continuous investment in infrastructure, parks, schools, and commercial development.

Opendoor included Winter Garden’s ZIP code 34787 as one of its notable “hidden gem” housing markets, and many of our new neighbors come from expensive markets like New York, Washington D.C., and Chicago, selling high-priced homes up north and finding tremendous value here.

Growing Pains and Future Outlook

Let’s be honest: rapid growth comes with challenges. Traffic on CR 535 and New Independence Parkway can be brutal during rush hour. Road expansions are planned but lag behind development. Construction seems endless.

But Orange County is investing heavily to catch up by widening roads, adding fire stations, building the 220-acre Horizon West Regional Park, and continuously improving infrastructure.

The market itself has normalized after the pandemic frenzy. In 2021-2022, homes sold in days with multiple offers above asking price. Now, inventory has increased, homes take about 60 days to sell, and buyers have negotiating power. It’s a healthier, more balanced market, but demand remains strong.

A Personal Reflection

Watching Winter Garden transform from the quiet town where I went to high school into this booming, dynamic community has been surreal. Part of me misses those orange groves and the slower pace. But another part is proud to see my hometown thriving, attracting families, creating opportunities, and becoming a place people dream of moving to.

My family’s home (the same house, same floors, same roof) tripling in value without us lifting a finger shows just how hot this market has been. That’s not luck. That’s Winter Garden becoming exactly what Central Florida needed: a place that honors its history while embracing smart growth.

If you’re considering Winter Garden, whether you’re drawn to the historic charm of Plant Street or the modern communities of Horizon West, you’re looking at one of Florida’s strongest markets. The fundamentals (population growth, strategic location, quality of life, and ongoing investment) suggest this isn’t a bubble. It’s the new reality.

From orange groves to Orlando’s hottest market: Winter Garden’s transformation has been remarkable. And honestly? I think we’re just getting started.