Westport, CT: The Hottest Town in Fairfield County

Over the past two years, Westport, Connecticut, has emerged as the hottest town in Fairfield County. This vibrant community, nestled on the Long Island Sound, offers a unique blend of small-town charm and cosmopolitan appeal that has attracted homebuyers from across the region and beyond. With its top-rated schools, thriving dining scene, and diverse range of activities, it’s no wonder that Westport has become such a desirable place to live.

A Thriving Real Estate Market

One of the key factors driving Westport’s popularity is its thriving real estate market. Despite the challenges posed by the global pandemic, the Westport housing market has remained robust, with home values steadily increasing over the past two years.

In April 2023, the median listing home price in Westport was $2.5M, trending up 9.1% year-over-year. The median listing home price per square foot was $574. The median home sold price was $1.5M. Homes in Westport sold for approximately the asking price on average in April 2023, with a sale-to-list price ratio of 99.22%.

On average, homes in Westport sell after 43 days on the market. The trend for median days on market in Westport has gone down since last month, and slightly up since last year. There are 245 homes for sale, ranging from $350K to $12M, providing a wide range of options for prospective homebuyers.

Top-Rated Schools in Westport

Westport is part of the Westport School District, which is known for its strong academic programs and commitment to student success. According to GreatSchools, some of the top-rated schools in the district include:

  • Staples High School: Known for its strong academic programs and wide range of extracurricular activities, Staples High is one of the top high schools in Connecticut.
  • Bedford Middle School: This school is known for its dedicated teachers and supportive community. The school offers a wide range of programs to help students succeed.
  • Green’s Farms School: This elementary school is known for its strong academic programs and supportive community. The school’s staff is dedicated to helping students succeed.

A Foodie’s Paradise

Westport is also a food lover’s dream. Here are the top five restaurants that you must try:

  1. The Whelk: Known for its seafood dishes and waterfront views, The Whelk is a local favorite. With its cozy atmosphere and excellent service, it’s the perfect place for a romantic dinner or a special occasion.
  2. Kawa Ni: This upscale restaurant offers a menu that changes with the seasons, ensuring that you’ll always find something new and delicious to try.
  3. Terrain Garden Cafe: If you’re in the mood for a unique dining experience, Terrain Garden Cafe is the place to go. Their menu is a hit with locals and visitors alike.
  4. Tarry Lodge: Located in the heart of Westport, Tarry Lodge offers a menu that combines classic Italian dishes with modern twists.
  5. Jesup Hall: This restaurant is known for its American cuisine and extensive wine list. The menu also includes a variety of seafood and vegetarian options.

Things to Do in Westport

Westport is a town that’s full of things to do. Whether you’re a nature lover, a history buff, or a foodie, you’ll find something to enjoy in Westport. Here are the top 10 recurring popular community events that are likely to take place in Westport:

  1. Westport Fine Arts Festival: This annual event showcases the work of local and regional artists in a variety of mediums, including painting, sculpture, photography, and more.
  2. Westport Farmers Market: A weekly event during the warmer months where local farmers and artisans sell fresh produce, baked goods, and handcrafted items.
  3. Levitt Pavilion Summer Concert Series: A series of free outdoor concerts held at the Levitt Pavilion throughout the summer months.
  4. Westport Library Book Sale: This annual event is a book lover’s dream, offering thousands of books in all genres at bargain prices.
  5. Westport Country Playhouse Season: The historic Westport Country Playhouse offers a season of plays and musicals, often featuring well-known actors and directors.
  6. Westport’s Slice of Saugatuck Festival: A food and music festival celebrating the Saugatuck neighborhood of Westport with food tastings, live music, and activities for kids.
  7. Westport Restaurant Week: This event, held twice a year, offers diners the chance to try prix fixe menus at participating Westport restaurants.
  8. Blues, Views & BBQ Festival: This annual event features live blues music, a BBQ competition, food vendors, and activities for kids.
  9. Holiday Lights Festival: A holiday event featuring a tree lighting ceremony, holiday music, and festive decorations throughout downtown Westport.
  10. Westport Road Runners Summer Series: A series of weekly road races held throughout the summer, with distances ranging from 2.2 miles to 10 miles.



In conclusion, Westport, Connecticut, with its thriving real estate market, top-rated schools, and vibrant dining scene, has rightfully earned its title as the hottest town in Fairfield County over the past two years. Its rich history, diverse community, and plethora of activities make it a truly unique place to call home. Whether you’re a nature enthusiast, a food lover, or someone seeking a community with a strong sense of place, Westport has something to offer. As the town continues to grow and evolve, it remains committed to preserving its small-town charm and fostering a community that is inclusive, dynamic, and forward-thinking. Come and see for yourself why so many people have chosen to call Westport home.