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Best Neighborhoods to Live in the Southport, CT Area

A charming coastal hamlet infused with rich history, Southport, CT, is a haven. 

It's a backdrop beautiful enough to be featured in Leonardo DiCaprio and Kate Winslet's 2008 film "Revolutionary Road." But looks aren't the only thing this community has to offer; we know because Raymond Design-Builders has been cultivating homes here for over 20 years. 

We'll be your guide to the area as you search for the perfect place to call home. Let's get the tour started! 

What is Southport, CT, like to live in? 

Living in Southport, CT means plentiful access to Long Island Sound, stunning ocean views, and breathtaking 18th-and-19th-century architecture everywhere you look. Country and yacht clubs are a favorite pastime, where members can go golfing, play tennis, enroll their children in sailing lessons, and hit the water before returning from a day's fun for a hearty club dinner. 

If you were to look at a Southport, CT map, you'd see that it's located in the town of Fairfield and borders Westport. Mill River runs on one side and Sasco Brook on the other. Long Island Sound is at its front, making the neighborhood surrounded by water on three sides. With natural beauty abounding, gorgeous homes, excellent public and private schools, and a civically-minded community, Southport offers a place to call home unlike any other.  

Best Places to Live in Connecticut Near Southport

Having options is always a good thing. So, let's look at nearby neighborhoods in the Fairfield and Westport, Connecticut, area with similar characteristics!

Southport CT waterfront business with white brick and wood patio furniture - photo by Greenwich Time

Fairfield, Connecticut Neighborhoods  

Greenfield Hill

Greenfield Hill is a historic neighborhood located on the northwest side of town. It's known for the protected 19th-century and pre-Revolutionary War buildings that dot the landscape, as well as the Dogwood Festival, a fixture in the community since 1936. 

Greenfield Hill is the most rural district in Fairfield, tucked away from the busyness of the town. Homes here are on large lots with much space between each house. If you want to escape from a bustling city, this is the place to do it. You'll have room to put in a pool (if the property you buy doesn't already have one) and any other home accessories you desire. Of course, the distance from shops and restaurants can be a downside, but the plus side is quiet country privacy!

Sasco Hill

Sasco Hill is part of Southport. The neighborhood rests along Long Island Sound and adjacent to Southport Harbor, lined with multi-million dollar homes. The luxury homes here have spectacular ocean overlooks and are themselves a sight to behold, forming one of the most sought-after neighborhoods in Fairfield. Sasco Hill dwellers are minutes away from the Country Club of Fairfield and the secluded Sasco beach, which is only open to town residents. 


Sturges is the best of both worlds. It's conveniently near downtown and Perry's Mill Pond Open Space Area. Enjoy regular walks or morning runs through the 58-acre area before heading into town to tackle your errands for the day or visit an award-winning restaurant. The neighborhood is also close to the Fairfield train station, making this an ideal location for commuters. Historic architecture abounds here, too, with homes like the 1840 Jonathan Sturges House, a gothic revival cottage. 

Westport, Connecticut Neighborhoods

Greens Farms

The oldest neighborhood in town, Green's Farms, was founded as a settlement in 1648 by five farmers, including John Green (for whom the area is named). Today this once farmer's paradise retains its rural beauty and woodlands while becoming a thriving suburb in close proximity to the railroad station. Many residents join the Green's Farms Association to help preserve the historic area. The neighborhood is known for the massive luxury homes along Beachside Avenue, where celebrities such as Phil Donahue, Marlo Thomas, and Marc Lasry have lived. 

Old Hill

As the name suggests, Old Hill is a similarly historic neighborhood. It primarily features homes from the Revolutionary and Victorian eras, which have been revamped for modern life. Many residents move here for high-quality schools. At the center of the community is Earthplace, a 62-acre park and wildlife sanctuary with a museum and amphitheater that offers continual family fun. 

What Is the Best Place to Live in Connecticut? A Home Built for You

Picking a neighborhood is only the first step. After that, there's the task of finding a home that fits your family's needs, which can be more complicated than you might think. It's rare to come across a pre-lived-in house that matches your vision for your dream home. The odds are that to get the home you've always wanted, you'll have to do some level of customization through remodeling. 

Prepare yourself for creating the perfect home with the Connecticut Remodeling Cost Guide from Raymond Design-Builders. 

Once you've found a neighborhood and property, contact us. We can turn that pre-built house into a personally-built home — or design you a new custom home from scratch! 


Get A Quote Raymond Design

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