Westport

Westport, CT, strikes a seamless blend of carefree coastal elegance, classic New England charm, creative edge, and modern sophistication all wrapped into one vibrant town. With around 27,000 residents, this quintessential waterfront town has long been a magnet for artists, entrepreneurs, and executives alike - think celebrity retreat meets cultural powerhouse. Nestled where the Saugatuck River flows into Long Island Sound, Westport offers everything from beachy escapes at Compo, Mill Cove, and Burying Hill to countryside estates with stonewalls and sweeping views. Beachside Avenue is renowned for its collection of premier waterfront estates, where properties have been cherished for generations, and discerning buyers, including the nation’s wealthiest, are drawn by the stunning views and unparalleled access to Long Island Sound. Westport’s Downtown Main Street and the revitalized Saugatuck Center pulse with upscale and casual dining, trendy boutiques and national and international brands, art galleries, summer concerts (Levitt Pavilion), and Farmer’s Markets. Beloved neighborhoods include: Compo Beach, Greens Farms, Long Lots, Hunt Club, Coleytown, Old Hill, & Redcoat.

 

Education here is top-tier: Staples High School ranks #1 in Connecticut and among the top in the nation, backed by five elementary schools, two middle schools, and the private Green’s Farms Academy. The arts thrive at Westport Country Playhouse, MoCA Westport, and Levitt Pavilion, while outdoor lovers flock to Longshore Club Park (Westport’s public country club-like facility for residents with golf, sports courts, pool, and ice skating in the winter), Sherwood Island State Park, and the beloved Winslow “Dog” Park. Indoor fitness is taken seriously here too. From state-of-the-art YMCA to boutique studios and high-performance gyms, Westport offers elite options for all levels and ages. Just a short Metro North train ride into Manhattan, Westport is a town defined not just by its shoreline and charm, but by a vibrant, diverse community united by a shared pursuit of living well, creatively, and with purpose.

Fun Facts: Westport’s past and present residents include Paul Newman, Martha Stewart, Michael Bolton, Shonda Rhimes, Craig Melvin, and Olympic snowboarder Julia Marino.