Connecticut’s priciest towns and cities have seen their real estate values skyrocket over the past decade. An analysis of the top 20 most expensive municipalities as of November 2024 reveals some striking common threads along with eye-popping price tags and growth rates. Data sourced from Zillow Home Value Index.
Fairfield County in the southwest corner of the state dominates the list, with shoreline communities also well represented, highlighting the premiums placed on proximity to New York City and waterfront living. The lucky residents of these exclusive zip codes enjoy charming historic architecture, vibrant downtown centers, cultural attractions, abundant natural beauty and recreation – and of course, top-ranked schools. But the privilege of calling these coveted communities home comes at an ever-steepening cost, with the “cheapest” towns on the list surpassing $600,000 and the priciest exceeding $2 million as of 2024.
#20. Woodbridge
The median home value in Woodbridge was $373,774 in 2015, $385,488 in 2020, and reached $623,598 by 2024. Over the 2015 to 2024 period, home values appreciated by a substantial 66.84%.
Woodbridge is a quaint suburban town near New Haven, known for its picturesque countryside setting, historic homes, and highly-regarded school system. Its convenient location and rural charm make it an attractive community for families.
#19. Madison
In Madison, the median home value started at $405,213 in 2015, dipped slightly to $400,120 by 2020, but then surged to $654,923 as of 2024. The coastal town experienced a 61.62% increase in home values from 2015 to 2024.
Situated along the Long Island Sound shoreline, Madison offers beautiful beaches, a charming downtown with boutique shopping and dining, and a friendly small-town atmosphere. Its waterfront location is a key draw for residents and visitors alike.
#18. Stamford
Stamford’s median home value was $437,487 in 2015, growing to $465,341 by 2020 and then $665,734 in 2024, marking a 52.17% appreciation from 2015 to 2024.
As Connecticut’s third-largest city, Stamford is a major business hub with a thriving downtown, diverse neighborhoods, and ample parks and recreation. Its proximity to New York City combined with lower cost of living makes Stamford an appealing location.
#17. Cornwall
Cornwall’s median home values were $392,071 in 2015, $416,751 in 2020, and $666,841 by 2024, increasing 70.08% over the 2015 to 2024 timeframe.
Located in scenic Litchfield County, Cornwall is a rural gem known for its vibrant arts community, beautiful Housatonic River, and outdoor recreation like hiking, fishing and skiing. The town’s natural beauty and cultural offerings are highly appealing.
#16. Sherman
In Sherman, median home values started at $395,586 in 2015, rose to $429,175 by 2020, and reached $670,892 in 2024, appreciating by 69.59% from 2015 to 2024.
Sherman is a charming town tucked in the hills of northern Fairfield County, offering peaceful country living around the popular Candlewood Lake. Outdoor enthusiasts are drawn to the area’s natural beauty and recreational opportunities.
#15. Bridgewater
Bridgewater saw median home values of $437,310 in 2015, $433,907 in 2020, and $713,374 by 2024, a 63.13% increase over 2015 to 2024.
Known for its picturesque rural setting, Bridgewater offers a quaint New England atmosphere with historic architecture, antique shops, art galleries and pristine parks. The small-town ambiance is a draw for those seeking a quiet lifestyle.
#14. Lyme
Lyme’s median home value was $437,363 in 2015, $454,115 by 2020, and grew to $737,247 in 2024, appreciating 68.57% from 2015 to 2024.
Situated along the Connecticut River, Lyme is known for its beautiful landscapes, land preserves, art galleries and the renowned Lyme Academy of Fine Arts. The town’s scenic beauty and strong arts presence are highly appealing.
#13. Redding
Redding’s median home values started at $524,412 in 2015, dipped to $499,998 by 2020, but rebounded to $813,787 in 2024, a 55.18% increase from 2015 to 2024.
Redding is prized for its open spaces, historic charm, and convenience to major employment centers. The town boasts excellent schools, beautiful parks like Huntington State Park, and a tight-knit community feel that draws residents.
#12. Salisbury
In Salisbury, median home values grew from $455,821 in 2015 to $489,736 by 2020 and $837,660 in 2024, an impressive 83.77% appreciation from 2015 to 2024.
Located in the picturesque northwest corner, Salisbury offers stunning natural beauty with mountains, lakes, and the Appalachian Trail. The town is known for its vibrant cultural scene with art galleries, live music, unique shops and fine dining.
#11. Fairfield
Fairfield’s median home value was $545,335 in 2015, saw a modest uptick to $549,641 by 2020, then jumped to $856,816 in 2024, a 57.12% increase over the 2015 to 2024 period.
Fairfield offers a vibrant mix of shoreline beauty, historic charm, universities, and a thriving downtown. Residents enjoy beaches, marinas, parks, and a convenient location between New York City and New Haven.
#10. Easton
In Easton, the median home value was $600,595 in 2015, dipped to $549,631 by 2020, but rebounded strongly to $885,951 in 2024, appreciating 47.51% from 2015 to 2024.
Easton is a quiet, rural town characterized by open spaces, historic farms, and large residential properties. Known for excellent schools and a tight-knit community, Easton offers a peaceful country setting within reach of urban amenities.
#9. Ridgefield
Ridgefield’s median home values were $568,745 in 2015, $558,176 by 2020, and grew to $903,723 in 2024, increasing 58.90% over the 2015 to 2024 timeframe.
This charming town boasts a vibrant downtown with unique shops, galleries, theater and fine dining. Ridgefield’s historic district, beautiful parks, and community events foster a strong sense of place appreciated by residents.
#8. Washington
In Washington, median home values started at $509,612 in 2015, grew to $533,037 by 2020, and reached $909,982 in 2024, an impressive 78.56% increase from 2015 to 2024.
The scenic town of Washington is known for its rolling hills, historic architecture, antique shops and art galleries. The prestigious Gunnery prep school and vibrant arts scene centered on the Washington Art Association are key community assets.
#7. Roxbury
Roxbury saw median home values appreciate 69.54% from 2015 to 2024, starting at $549,251 in 2015, $555,607 by 2020, and reaching $931,174 in 2024.
This pretty rural town in Litchfield County is characterized by rolling farmland, historic homes, and land preserves. Roxbury’s natural beauty, land conservation, and small-town charm are a strong draw for residents.
#6. Wilton
In Wilton, the median home value was $770,324 in 2015, dipped to $687,814 by 2020, but rebounded to $1,106,974 in 2024, a 43.70% appreciation over 2015 to 2024.
Wilton is an affluent community known for its excellent schools, historic architecture, quaint town center, and ample green spaces. The town’s rural character balanced with convenient amenities is highly desirable.
#5. Weston
Weston’s median home values grew 49.02% from 2015 to 2024, starting at $813,006 in 2015, receding a bit to $712,683 by 2020, but jumping to $1,211,517 in 2024.
This rustic town is characterized by open spaces, wooded areas, historic farms and grand estates. Weston’s rural tranquility, top-notch schools, and proximity to NYC make it a sought-after place to live.
#4. Westport
In Westport, the median home value was $1,143,138 in 2015, dipped to $1,031,316 by 2020, but surged to $1,728,844 in 2024, appreciating 51.24% from 2015 to 2024.
Westport offers waterfront beauty, a vibrant downtown, and strong arts and culture scene. The town’s beaches, marinas, excellent schools and convenient access to NYC are key draws for its residents.
#3. New Canaan
New Canaan’s median home values started at $1,377,705 in 2015, decreased to $1,134,856 by 2020, but rebounded strongly to $1,871,728 in 2024, marking 35.86% appreciation from 2015 to 2024.
Known for its classic New England charm, New Canaan boasts a pretty downtown with exceptional shopping and dining. The town’s excellent schools, beautiful parks, and iconic modern architecture are highly valued by residents.
#2. Darien
In Darien, median home values were $1,383,605 in 2015, dipped to $1,238,398 by 2020, but grew to $1,995,419 in 2024, a 44.22% increase over 2015 to 2024.
This beautiful coastal town offers beaches, marinas, country clubs, and a charming downtown. Darien’s waterfront location, top-ranked schools, and convenient train access to NYC make it a highly desirable place to live.
#1. Greenwich
Greenwich saw median home values start at $1,402,906 in 2015, decline a bit to $1,318,278 by 2020, then jump to $2,016,552 in 2024, appreciating 43.74% from 2015 to 2024.
Famed for its wealth, Greenwich offers a posh yet charming setting with luxury shopping, fine dining, and spectacular waterfront estates. Its beaches, parks, elite schools and proximity to NYC make Greenwich one of the nation’s most coveted places to live.
