Homes for Sale in Westport, CT

Westport occupies a prime stretch of the Connecticut shoreline where the Saugatuck River meets Long Island Sound, and for decades it has attracted writers, executives, media professionals, and anyone who wants the lifestyle of coastal New England without actually leaving the orbit of New York City. The town is defined by water — marinas, yacht clubs, town beaches, the historic Saugatuck neighborhood, and the famed Longshore Club Park, which packs an 18-hole golf course, sailing school, tennis complex, and waterfront dining into a single town-owned facility.

The real estate market reflects the town's enduring appeal. The median home price reached approximately $2.0M in early 2026, up 27.8% year-over-year. At the high end, waterfront estates trade for $5M to nearly $20M. The most coveted properties cluster around Saugatuck and Saugatuck Shores — walkable to downtown restaurants and shops, with water views and, in some cases, private docks. Homes near the two Metro-North stations command a consistent premium and tend to sell significantly faster than the town average.

Westport's school system consistently ranks in the top 10 for the New York metropolitan area. Staples High School is widely regarded as one of the finest public high schools in Connecticut, known for its college preparation rigor, performing arts program, and competitive athletics. For buyers weighing the price premium of a Westport address against a neighboring town, the school district — and the lifestyle that comes with it — is almost always the deciding factor.

Westport is one of Connecticut's most competitive real estate markets — and one where the difference between a good listing agent and a great one shows up clearly in the final sale price. With median prices regularly exceeding $1.5M and a buyer pool that includes experienced New York City transplants who know value, every aspect of how your home is priced, prepared, and presented matters.

Alex Capozzoli has a documented track record of over-ask results across Connecticut — including $36,000 above asking in Newtown, $35,100 above in Naugatuck, and $31,000 above in Morris. Those results come from a consistent approach: pricing to create competition rather than waiting for a single buyer to bite, combined with professional presentation and Keller Williams' full marketing platform.

If you're considering selling your Westport home, Alex offers a free market analysis to give you an honest, data-based view of what it would sell for today — and what strategy would get you there.