50 MOST EXPENSIVE TOWNS
IN CONNECTICUT

As we saw in our 2023 Year in Review Housing Report, home prices continue to rise across Connecticut.  The average selling price for a home hit $496,664 by year’s end, an increase of 7.1% compared to 2022, and the highest monthly average selling price this year.

Here is a list of the most expensive towns in Connecticut in 2023:

1. Darien

Darien comes first on our list, with the average selling price for a home at $2,378,483, and a total of 253 homes sold in 2023. Darien is known for its beautiful beaches, such as Weed Beach and Pear Tree Point Beach, popular destinations for sunbathing, swimming, and picnicking. Darien also has a rich cultural scene, with a variety of art galleries, historic landmarks, and museums to explore. For example, the Darien Historical Society Museum is a great place to learn about the town’s fascinating past. Foodies will love the variety of restaurants and cafes, which serve up everything from classic New England fare to global cuisine.

2. Westport

The town of Westport, Connecticut is number two on the list! In 2023, The average selling price for a home in Westport is $2,306,871. Westport is a charming New England town with a vibrant cultural scene. The town is home to a variety of cultural attractions, including the Westport Country Playhouse, Levitt Pavilion for the Performing Arts, and the Westport Arts Center. Visitors can also explore the historic Saugatuck neighborhood, which is lined with unique shops, restaurants, and art galleries. For outdoor enthusiasts, Westport boasts beautiful beaches, nature preserves, and hiking trails. With its picturesque New England scenery and rich cultural offerings, Westport is a must-visit destination, and a great place to live!

3. Greenwich

Coming in at number three is the town of Greenwich with an average home selling price of $2,228,902. Located on the coast of Long Island Sound, Greenwich is a picturesque town with a rich history and a thriving cultural scene. Visitors can explore the historic Greenwich Point Park, take a stroll through the Bruce Museum of Arts and Science, or enjoy the stunning natural beauty of the Audubon Center. The town is also home to a variety of world-class restaurants, boutique shops, and galleries, making it a perfect destination for a day trip or weekend getaway. With its charming New England architecture and abundance of local attractions, Greenwich has something for everyone to enjoy.

4. New Canaan

New Canaan, another small town, places fourth on our list, with an average selling price of $1,975,324. New Canaan is a perfect place for both nature and art lovers alike! Stroll through Waveny Park and Grace Farms or get lost in the art featured at the Silvermine Arts Center. New Canaan is also the home of some of New England’s most amazing architecture, including Philip Johnson’s Glass House. The food scene is also something to remember, with an abundance of farm-to-table restaurants to explore!

5. Washington

Washington has an average selling price of $1,359,963 and a total of 41 homes sold in 2023. With a mix of natural beauty, history, and culture, Washington is a wonderful place for anyone looking to escape the hustle and bustle of city life. The town is known for its stunning natural beauty, with plenty of parks, lakes, and forests to explore, including Steep Rock Preserve and Lake Waramaug State Park. Despite its rural setting, the town boasts a thriving arts and culture scene, with a variety of galleries, theaters, and music venues!

6. Salisbury

In 2023, the average price for a home in Salisbury was $1,337,024, up 3 spots from 2022! Salisbury is a nature lover’s dream, with an abundance of lush forests, and several state parks and nature preserves nearby, including the Appalachian Trail, which runs through the town. It is also the home to several galleries, museums, and performing arts venues to explore, and hosts the very popular Labor Day Weekend Arts Festival each year! With a population of just over 3,000 people, Salisbury has a very close-knit community.

7. Weston

Weston has an average home selling price of $1,326,909. Weston is a charming town located in Fairfield County, Connecticut. It’s a small town known for its picturesque landscape, rural character, and excellent schools. Weston is a great place to live if you enjoy the outdoors, as there are many parks and nature preserves in the area, including Devil’s Den Preserve and Trout Brook Valley Preserve. One of the top attractions in Weston is the Lachat Town Farm, a historic farm that’s been transformed into a community space with events, programs, and a farm stand. The town also has a thriving arts scene, with the Weston Playhouse and the Weston Historical Society offering a variety of events throughout the year.

8. Roxbury

Roxbury had 20 home sales in 2023 and the average selling price for a home was $1,181,931. Roxbury is known for its rural charm, rolling hills, and historic homes. It’s a great place to live if you’re looking for a peaceful lifestyle. The town is also home to Mine Hill Preserve, which features hiking trails and stunning views of the surrounding countryside. It is also a great place to live if you value a strong sense of community. The town hosts a variety of events throughout the year, including an annual farmers’ market, a Fourth of July celebration, and a holiday tree lighting ceremony.

9. Wilton

Wilton is number nine on the list with an average selling price of $1,121,021 in 2023. Wilton is a great place to live if you value a tight-knit community, excellent schools, and plenty of natural beauty. Wilton is home to several private schools, including the Montessori School and the Academy of Dance and Music, and its many other schools rank among the top in the state. Its proximity to larger cities like Stamford and Norwalk makes it a convenient choice for commuters, while its small-town charm and amenities make it a popular choice for families and professionals alike.

10. Ridgefield

Ridgefield rounds out our list for 2023 with an average selling price of $1,083,523 and 327 home sales. Ridgefield is mainly known for its unique blend of history and modernity. The town’s founding took place in 1709, and much of its charming colonial architecture has been meticulously maintained. Residents take pride in preserving the town’s heritage while embracing innovation and progress. Some popular attractions in Ridgefield include the Ridgefield Playhouse, showing lively performances throughout the year, The Aldrich Contemporary Art Museum boasting fascinating pieces, and the Ridgefield Symphony Orchestra serenading the town with music. Additionally, there are plenty of opportunities to explore the outdoors and all the serene New England landscapes Ridgefield has to offer. 

**All total sales and average selling price data provided by Smart MLS