Clermont Vs. Winter Garden

In our Facebook Group Magical Moves, I posted a poll of the top questions our buyers had. Want to know what was number #1? “What are the differences between Clermont & Winter Garden?!” Undeniably, these two areas are also our most popular areas for Magical Movers! If you live out of state, differentiating between the two Orlando, Florida suburbs via google maps can only take you so far. Getting a feel for an area while you’re 1,000 miles away is difficult. Personally, I really love both. I think they’re both great areas to raise a family. I’m actually moving to Clermont shortly! 

What’s the difference between Winter Garden and Clermont? Are they relatively similar, or completely different? What are the advantages and disadvantages of each?

Clermont has much more land. Clermont is still largely undeveloped, the miles of rolling hills on HWY-27 are proof. The City of Clermont also recently lifted a sanction allowing builders to build more residential and commercial property, opening the gates to construction. The rural Clemont I know and love may be gone within the next 20 years, but the beautiful lakes and hills wont. 

Winter Garden has more Charm. Winter Garden is the “it” city for anyone looking to live in an area with a charming, beautiful, and vibrant downtown community feel. Historic Downtown Winter Garden reminds me of Celebration, without the feeling of being a pre-programed, perfect neighborhood.

Downtown Winter Garden

Clermont has more hills. A lot more. Clermont is a unicorn in Central Florida. While most of Orlando is incredibly flat, lowlyings swampland, Clermont is the complete opposite.  Rolling hills and scenic vistas abound. Winter Garden does have one or two hills, and isn’t as low-lying as the rest of Orlando, but it can’t compete with Clermont.

The hills are alive in Clermont!

Winter Garden is more expensive. Winter Garden has a great location, amazing culture and a hometown feel. Because demand is high to live here, home prices have increased too. Winter Garden sits right above Magic Kingdom to the West, which is perfect for an afternoon at Disney and avoiding Orlando/Kissimmee traffic too!

If you live along HWY 27, (Clermont) there’s a good chance you’ll be connected to Winter Garden in the near future. Currently there are no roads along Southern Clermont & Winter Garden (except a very cumbersome dirt road) that connect between HWY 27 and Toll Road 429 (Winter Garden / Hamlin / Horizon’s West). The highlighted squiggles below are my best attempts at highlighting future roads that will connect HWY 27 to Toll Road 429, creating a super quick link between Clermont and Winter Garden. 

While Winter Garden is a little more upscale, both Winter Garden and Clermont provide a sense of relief from the hustle and bustle. If you’re looking for natural beauty without pretense, Clermont might be for you. But if you want to live in the coolest town with fun shops and restaurants, Winter Garden is the place to be. No matter which area you choose, both Winter Garden and Clermont are family-focused, residential neighborhoods. 

Eric Gross

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1 Comment

  1. Cyn Uehara on June 6, 2020 at 1:01 am

    Eric, Clermont seems like the perfect place for my hubby and I. We will be retired and want a maintenance-free newer home. Our girls will move there first, maybe sometime next year, and we will follow a few years later. Thank you for all this information. I can’t wait to contact you when we are nearer to moving/purchasing.

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