1. Darien, CT – The Quintessence of Coastal Luxury
Darien blends its natural coastal beauty with a rich social tapestry, boasting events like the Darien Nature Center’s annual “Down on the Farm” event. With a median home price of $1,656,964, the town offers an enviable mix of cultural activities, highly-rated schools, and the serene ambiance of its beaches, making it a perfect spot for both nature lovers and social butterflies.
2. Old Greenwich, CT – Where Seaside Serenity Meets Elegance
Old Greenwich is more than its shoreline; it’s a community where history meets modern living. The annual Greenwich Point Conservancy Beach Ball is a highlight, celebrating the town’s heritage. With homes averaging $1,928,271, residents enjoy a blend of upscale local shopping, community-focused events, and a strong sense of belonging, all within the charm of a coastal town.
3. Weston, CT – A Haven of Greenery and Grace
In Weston, where homes average $1,415,052, the town is not just a nature lover’s paradise but also a cultural hub. The Weston Historical Society frequently hosts events that celebrate the town’s rich history, providing a deep sense of community amidst the backdrop of natural preserves and engaging local events like the Weston5K Run and Walk.
4. Riverside, CT – The Picture-Perfect Neighborhood
Riverside, with its average home value of $1,220,093, is renowned for its community-centric lifestyle. The annual Riverside Garden Club Plant Sale is a local favorite, fostering community spirit. The town combines the allure of the Riverside Yacht Club and the scenic beauty of the Riverside Avenue Bridge with excellent public schools, making it a top choice for families.
5. New Canaan, CT – Where Tradition Meets Trendy
New Canaan, with a median home price of $1,303,975, is a haven for architectural enthusiasts and community gatherings. The town is not only famous for its Philip Johnson Glass House but also for its vibrant downtown area, hosting events like the “Caffeine and Carburetors” car show, which blends community spirit with a flair for the finer things in life.
6. Westport, CT – Coastal Charm with a Creative Twist
Westport’s median home value of $1,802,918 is complemented by its artistic soul. The town is a hotspot for creatives, home to the famed Levitt Pavilion for Performing Arts and the bustling Farmers’ Market, making it a place where arts, culture, and coastal living blend seamlessly.
7. Greenwich, CT – Synonymous with Sophistication
Greenwich, with homes averaging $1,710,154, offers more than just luxurious living; it’s a cultural haven. The town is known for its exclusive shopping districts and the Greenwich Polo Club, combining high-end leisure with cultural richness, making it an epitome of upscale living.
8. Wilton, CT – A Blend of Affluence and Artistry
Wilton, where homes average $1,013,265, balances its luxury with a strong community spirit. The town hosts the popular Wilton Library Annual Book Sale, attracting book lovers and families. Its commitment to conservation and a thriving arts scene makes it a unique blend of affluence and community-oriented living.
9. Cos Cob, CT – Small-Town Feel, Big-Time Luxury
Cos Cob’s average home price of $1,319,067 reflects its serene yet rich historical background. The town hosts the Cos Cob Archers Open Shoot, appealing to outdoor enthusiasts. Its blend of historical sites like the Bush-Holley House and natural beauty like the Mianus River Park offers a unique living experience.
10. Groton Long Point, CT – Coastal Living at Its Finest
In Groton Long Point, with average home prices at $1,191,472, life is about embracing the sea. The Groton Long Point Yacht Club hosts sailing lessons and regattas, enhancing the maritime lifestyle. It’s a place where beach life and boating create a relaxed yet vibrant community atmosphere.
11. Madison, CT – Coastal Charm with a Cultural Spin
Madison, with an average home price of $1,112,856, is a coastal gem that thrives on its cultural and natural richness. The annual “Shakespeare on the Shoreline” event is a testament to the town’s cultural vibrancy. It’s a place where the charm of beachside living meets a rich tapestry of arts and community events.