Today, we begin a new series here at the Carriage Properties Blog – Sidewalk Chats. This series will give our readers the opportunity to get to know the Agents and Partners at Carriage Properties, as they stroll around the city they love. Up first is Partner/Realtor Thomas Bennett. A native Charlestonian with a strong knowledge of architecture and historic preservation, Bennett has owned and restored many notable properties within Charleston’s historic district – including the famed Pineapple Gate House at 14 Legare Street, pictured above. Below, our chat with Thomas.

What do you love most about Charleston?

This city is so incredible because it’s right on the ocean, and going across our bridges and over the marsh and looking towards the historic district is so beautiful. The combination of the city’s natural and architectural beauty is quite something. What can I say? – this city is a part of my soul, it’s in my DNA.


What is your favorite Charleston neighborhood?

The South of Broad Historic District, particularly from Legare Street east to the water.

What is your favorite Charleston street?

Legare Street. Absolutely no question. Quiet and serene. Stunning.


What is your favorite building in Charleston?

Honestly, there’s just no way to choose. And I have lived here all my life. Sometimes I see a building for the millionth time and I’m so in awe that it may as well be the first time I’m seeing it. And it may not be the best looking house on the block, or the most well kept, it won’t matter. I truly love all architectural periods, and we’re lucky here in Charleston because we have representation from the best of each period. That being said, however, one of my favorite “Charleston” buildings is Mulberry Plantation located out in Moncks Corner. The beauty and uniqueness of that house, coupled with its site on the high bluff overlooking the river is truly magical.


What is your favorite thing to do in Charleston?

Walking the city. The weather, the water, the streets, the food, the neighborhoods … did I mention the food? I love the ability to access good restaurants, museums, and outdoor spaces without having to use your car. Just walking is the best.

Thomas Bennett can be reached at 843-266-8002 or

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