The Ultimate Guide to Living in Southport, CT

Tucked along the scenic shores of Long Island Sound, Southport is a coastal village within Fairfield that has a charm and identity all its own. Steeped in history and known for its elegant homes, walkable town center, and vibrant harbor, it’s no surprise that Southport is one of the most desirable neighborhoods in Fairfield County.

A Blend of History, Luxury, and Community

Southport’s history dates back to 1639, and its historic character is carefully preserved through strict zoning regulations. As a designated local historic district, many of the homes—especially near the coastline—feature 18th and 19th century Federal and Greek Revival architecture, creating a timeless sense of place.

Today, Southport continues to attract buyers seeking a luxurious yet laid-back coastal lifestyle. The median sale price for a home in Southport is currently $1,362,500, reflecting the area's strong demand and upscale offerings. While grand waterfront estates dominate the shoreline, smaller homes closer to I-95 are attracting younger buyers who value both charm and convenience.

The town center is filled with boutique shops, antique stores, and locally loved restaurants. The Delamar Hotel, a luxury boutique hotel, adds to the village's upscale yet approachable feel. Southport is also home to two historic churches—Southport Congregational Church and Trinity Episcopal Church—that play an active role in community events and outreach.

Waterfront Living and Recreation

Southport’s coastal location offers more than just views. It’s a haven for boaters and nature lovers alike. The private Pequot Yacht Club is a staple of the community, offering a variety of sailing programs. Ye Yacht Yard, a town-owned marina, provides public access with moorings, boat launches, and kayak racks for residents.

In addition to its harbor, Southport has its own beach, perfect for residents looking for a quieter shoreline experience. The Pequot Library, a privately run cultural hub, hosts events throughout the year, including concerts, lectures, the beloved Southport Garden Stroll, and one of New England’s largest summer book sales. Community fundraisers like Rooms with a View, organized by Southport Congregational Church, blend design, art, and philanthropy in support of local missions.

Schools and Convenience

Families are drawn to Southport for its strong education options and commuter-friendly location. The private Southport School offers a specialized K–8 education for students with language-based learning differences like dyslexia and ADHD. Public school students typically attend Mill Hill Elementary School, or Timothy Dwight Elementary for some areas just outside the census tract, followed by Roger Ludlowe or Tomlinson Middle School, and Fairfield Ludlowe High School.

Southport also offers one of the most convenient commutes into NYC, thanks to its own Metro-North train station, and quick access to Interstate 95, which runs through the neighborhood.

Why Southport?

Southport offers the perfect blend of beauty, lifestyle, and heritage. From its historic homes and stunning harbor to its strong schools and commuter access, it delivers a high-quality coastal living experience with the charm of a small village. Whether you're sailing at sunset, browsing local shops, or enjoying the timeless streetscapes, Southport is a place that truly feels like home.

Thinking of making Southport your home?
Let’s talk! As a Fairfield native and local expert, I’d love to help you discover everything this special community has to offer. I am to help you along your journey to homeownership.