Comparing Luxury Towns in Fairfield County

What’s the right fit for you?

With its top-rated schools, rich history, proximity to major cities, and charming towns, Fairfield County is one of the most desirable places to live in the U.S. Often referred to as the “Gold Coast,” Fairfield County is home to some of the nation’s most affluent towns.

While these towns share many similarities, each has its own unique personality. Here, we’ll take a look at life in the luxury towns of Westport, New Canaan, Wilton, Ridgefield, and Redding.


Located just 50 miles outside of New York City, this beautiful beach community offers the perfect balance between suburban tranquility and access to urban environments. An ideal location for commuters, Westport boasts beautiful public beaches, an extensive park system, and recreational facilities. Places like Compo Beach, Sherwood Island State Park, Longshore Club Park, and the Saugatuck River provide residents with opportunities for boating, golf, tennis, and other outdoor activities that are part of the active Westport lifestyle.

With one of the highest-performing high schools in the state and a strong sense of community, Westport also boasts a thriving art scene with the Westport Country Playhouse drawing both local and national performances. The town also hosts the Westport Arts Festival and many other cultural events, making it a hub for artists and creatives.


Considered more quiet than Westport, yet still offering a vibrant, suburban lifestyle, New Canaan is ideal for commuting professionals and their families. 

New Canaan is famed for its mid-20th-century modern architectural heritage. Included in this storied collection of modernist homes is by the “Harvard Five”—a group of architects influenced by Walter Gropius, the founder of the Bauhaus. This gives the town a unique architectural footprint that is rare in the region.

The town boasts a charming and bustling downtown area, blending together historic buildings, upscale boutiques, fine dining restaurants, and chic cafes. This busy downtown area serves as a social and commercial hub, attracting visitors from surrounding towns. 

And, most recently in 2024, New Canaan High School was named the Best Public High School in Connecticut.


Located east of New Canaan and Northwest of Westport lies the charming town of Wilton. While the town offers direct Metronorth train service to New York City, it is less of a commuter hub than busier Fairfield County towns. As a result, Wilton has a quieter, more laid-back feel, with winding country roads, less traffic, and ample green spaces. The town is committed to preserving its many historic buildings and landmarks like the Wilton Historical Society. 

In comparison to Westport or New Canaan, Wilton has less commercial development and a smaller selection of nightlife, retail, and dining options. Wilton residents enjoy more quality over quantity, with several high-quality eateries and boutiques that cater to a more local, intimate experience. All this results in a more subdued, residential character with a strong focus on family and local community events. 


Situated north of Wilton, Ridgefield balances historical charm with modern amenities and cultural richness. While maintaining its strong New England history (the town’s roots date back to the 1700s!), Ridgefield is also home to a vibrant cultural arts scene. With the Ridgefield Playhouse, Prospector Theatre, Aldrich Contemporary Art Museum, and more, residents and area guests enjoy a dynamic cultural experience in Ridgefield.  

The town also boasts what could be described as a Norman Rockwell-esque Main Street, which stretches more than a mile long and is lined with beautiful homes, museums, churches, shops, and restaurants. Compared to neighboring Wilton, Ridgefield’s offers a wider variety of dining and shopping options, especially around its downtown area. 

R E D D I N G 

Known for its scenic landscapes, tranquil beauty,  rolling hills, extensive forested areas, and conservation lands, Redding offers a more subdued and peaceful lifestyle. Its lower population density contributes to a quieter, more secluded living experience—a stark contrast to many of its neighboring towns. 

The Redding community is close-knit and there is limited commercial development and fewer retail and dining options in comparison to other towns in Fairfield County. Redding residents often travel to neighboring towns for shopping and entertainment, which contributes to a different kind of local economy centered more around local businesses. 

Fairfield County: There’s Something For Everyone

Whether you prefer a closer commute to New York City or a more rural lifestyle, each town in Fairfield County offers an abundance of benefits for its residents. Though each has its own unique personality, every town offers an award-winning school system, a strong sense of community, historical charm, beautiful landscapes, outdoor recreation and so much more!

Ridgefield realtor, Karla Murtaugh, and her team of experienced real estate specialists will be your guide as you determine what town is best suited for your lifestyle. Reach out to Karla today and let her help you find the home and town of your dreams.

Come see why they call it the “Gold Coast”!