Southport is a coastal village within the town of Fairfield, Connecticut, sitting where Southport Harbor meets Long Island Sound. Settled in 1639, it is one of the oldest communities in the state, and it looks the part. Wide, tree-lined streets are bordered by Federal, Greek Revival, Victorian, and Colonial homes, many dating back two or three centuries. The entire village center is a designated local historic district, listed on the National Register of Historic Places, and strict zoning laws keep it that way.
But Southport isn't a museum. It's a working, walkable community with its own Metro-North station, a small but excellent retail and dining scene, two active churches, a luxury boutique hotel (The Delamar), and a harbor full of sailboats. The village borders Westport to the east and extends south toward the Sasco Hill area and Long Island Sound. It's roughly an hour and ten minutes to Manhattan by train, and about 50 miles by car.
Here's the thing: Southport functions almost like its own town while benefiting from all of Fairfield's infrastructure, schools, beaches, and services.
Southport's housing stock is one of its defining features. The historic district is filled with privately owned homes in styles you won't find assembled like this anywhere else in Fairfield County:
Most homes in the historic district are on generous lots with mature landscaping. Waterfront estates and properties with harbor views command the highest premiums. That said, streets closer to I-95 (which cuts through the southern edge of the village) offer more moderately priced options, and these are increasingly attracting younger buyers who want the Southport address and community feel at a lower entry point.
Local Tip: Southport's strict historic district zoning means exterior renovations require approval. Buyers should factor this in, but it's also what protects the village's character and long-term property values. The limited turnover in the historic core keeps competition tight when homes do come on the market.
The Sasco Hill area, technically part of the broader Southport community, sits south of the harbor along Sasco Hill Road. This is where you'll find some of Fairfield's most prestigious addresses: gated, multi-million-dollar estates with sweeping views of Long Island Sound and the Country Club of Fairfield at the water's edge.
What does that mean for buyers? Southport offers a rare combination: a protected, authentic historic village with real architectural significance, walkability, its own train station, and direct water access. Few places in Fairfield County can match that.
Southport's restaurant scene is small but well-curated:
Local Tip: Paci is housed in a former freight depot right at the Southport train station. The industrial-high-ceiling space is striking, and the summer live music nights are a local favorite. Artisan at The Delamar is the go-to for a more refined evening out.
The village center has a small but intentional retail lineup:
Additional boutique shops and antique stores line the village streets. For a wider shopping selection, downtown Fairfield and Westport's Main Street are both just minutes away.
Southport's activities center around the water and the community:
And the best part? Southport's two signature annual events bring the whole village together:
Two historic churches, Southport Congregational Church and Trinity Episcopal Church, remain active hubs for events, outreach, and cultural programming. The Southport Congregational Church's annual "Rooms with a View" fundraiser celebrating art and architecture is another highlight on the calendar.
Southport has its own Metro-North station on the New Haven Line. Trains reach Grand Central Terminal in approximately 70 to 90 minutes depending on express vs. local service. The station has commuter parking with permit and daily options (permits have a waitlist; daily parking is available). I-95 is also immediately accessible.
By car, Manhattan is about 50 miles away. Southport's position between the Fairfield Center and Westport (Saugatuck) stations also gives commuters flexibility if schedules or parking don't align on a given day.
Southport is part of the Fairfield Public Schools district. Local elementary schools feeding from Southport include:
These feed into:
Private school options in and near Southport include:
For a full list of Fairfield's public and private schools, see the Fairfield neighborhood guide.
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