The Lamacchia Realty Top 10 Most Expensive Connecticut Towns report for 2024 is here! To compile this list, we analyzed every town in the state with a minimum of 200 homes sold in 2024, then ranked them by median sales price from highest to lowest.
Connecticut’s real estate market reached impressive heights in 2024, especially in these 10 standout towns. Known for their blend of coastal beauty, historic charm, and upscale appeal, these communities rank among the most desirable places to live in the state. Whether you’re thinking of making a move, or simply curious about where the market soared, this list spotlights the Connecticut towns where luxury living and New England character truly shine.
See below for the full breakdown for 2024:
#1 – Greenwich, CT
Greenwich takes the number one spot with 661 home sales in 2024 and a median home price of $1,900,000. Greenwich offers an exceptional blend of historic charm, luxurious living, and coastal beauty—making it one of the most desirable places to call home in the state
Attractions/Things to Do in/near Greenwich:
#2 – Westport, CT
Westport ranked second on the list with 354 homes sold and an average sales price of $1,730,072 in 2024. Known for its top-rated schools, thriving arts scene, and upscale suburban lifestyle, this vibrant coastal town is a highly sought-after community for families and professionals alike.
Attractions/Things to Do in/near Westport:
#3 – New Canaan, CT
Ranking third on the list, New Canaan reported 245 home sales and a median sale price of $1,700,000 in 2024. New Canaan offers a sophisticated yet family-friendly lifestyle with its distinctive architecture, top-tier educational system, and walkable village center.
Attractions/Things to Do in/near New Canaan:
The Philip Johnson Glass House
#4 – Wilton, CT
Coming in fourth, Wilton had 252 homes sold in 2024 and an average selling price of $1,107,650. This picturesque and family-oriented town is perfect for people seeking a peaceful wooded setting, strong community atmosphere and convenient commuting options to New York City.
Attractions/Things to Do in/near Wilton:
Weir Farm National Historic Site
#5 – Ridgefield, CT
Placing fifth, Ridgefield saw 310 home sales in 2024, with a median price of $888,000. Set against a backdrop of rolling hills and historic charm, Ridgefield features a vibrant cultural scene that appeals to those seeking both elegance and community.
Attractions/Things to Do in/near Ridgefield:
The Aldrich Contemporary Art Museum
#6 – Fairfield, CT
In sixth, Fairfield had 724 home sales in 2024 and an average sales price of $805,000. Fairfield combines small-town appeal with big-city amenities, offering a mix of coastal homes and charming neighborhoods.
Attractions/Things to Do in/near Fairfield:
Edgerton Center for the Performing Arts
#7 – Madison, CT
Ranked seventh on the list, Madison recorded 244 home sales in 2024 with a median sale price of $650,000. With its classic New England vibe, beachfront access, and gorgeous colonial architecture, Madison is a top choice for those drawn to scenic beauty and upscale, relaxed living.
Attractions/Things to Do in/near Madison:
#8 – Stamford, CT
Coming in eighth, in 2024 Stamford had 1,245 homes sold and an average sale price of $635,000. As one of Connecticut’s most dynamic cities, Stamford offers a wide range of living—from luxury apartments to suburban homes, coupled with a thriving business district and direct commuter access to Manhattan.
Attractions/Things to Do in/near Stamford:
Bartlett Arboretum and Gardens
#9 – Trumbull, CT
In ninth place, Brentwood recorded 373 home sales and a median price of $610,00 in 2024. Known for its family-friendly neighborhoods and highly regarded schools, Trumbull provides a suburban lifestyle with a strong community feel, and easy access to major highways and metro areas.
Attractions/Things to Do in/near Trumbull:
#10 – Norwalk, CT
Rounding out the top ten, the town of Norwalk had 818 home sales and an average selling price of $600,000 in 2024. From waterfront condos to historic homes, Norwalk has unique blend of city-like energy and coastal living, making it a prime spot for residents and vacationers alike.
Attractions/Things to Do in/near Norwalk: