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The 15 Richest Towns in Connecticut

Old Greenwich

Connecticut entered the union in 1788 as the fifth state. Hartford is the state capital and is considered the Insurance Capital of the U.S. as well.

Connecticut has eight counties that include 169 municipalities, 19 cities, 149 towns, and one borough. It is known as the Constitution State and is the most southern state in New England. However, the state is typically included in the behemoth tri-state New York metropolitan area that consists of the Empire State (N.Y.) and New Jersey.

So, where are the richest towns in Connecticut?

Like most states, Connecticut has exceptionally desirable places to reside. However, in the case of Connecticut, its Gold Coast is home to some of the state's priciest zip codes in the country because this is where a New York City commute is quick, convenient, and comfortable. Other tony places are situated along the state’s southern coastline with the Long Island Sound.  

Our Methodology

Our analysis applied two fundamental metrics to determine which of Connecticut’s towns are the wealthiest.

  1. The first metric applied to the analysis was the city/town’s median home price. To provide some context, it is noted that  Zillow reports that the median home price across the state is $377,247 - strikingly similar to Bankrate’s and NAR’s median price for the entire country of $387,600 (2023-Q4). However, the richest towns in Connecticut have homes that likely require down payments that far exceed the median price of a home across the state and country!
  2. The second metric refers to the location’s median household income, which can be sourced from various government and data/statistical websites. To determine the richest towns in C.T., we reviewed data and information sourced from multiple real estate and government reporting sites (i.e., U.S. Census, Connecticu-Demographics.com, Point2Homes, Data USA, etc.).

Given this current data and the application of some applied statistical analysis, we formulated the list below of the richest towns in Connecticut.

The 15 Richest Towns in Connecticut (Updated 2023)

Our list of richest towns in C.T. is ranked based on median property values, with a secondary metric of median household income for the residents of the town -

15. Stamford, Connecticut

  • Median Property Value: $614,530 - up 10% over the past year.
  • Median Household income: $99,791
  • Population – 136,309

Stamford is Connecticut’s third largest city, located along the Long Island Sound about 30 miles from the Big Apple. Despite being an economic hub with many corporate headquarters, the city is known for its diverse neighborhoods, with home prices that rise to some of the richest towns in Connecticut.  Shopping options for this modern city range from boutique shops to larger retail centers. Stamford has a vibrant cultural scene with theaters, art galleries, and museums. The city is known for the quality of its schools, private schools, and even institutions of higher education.

14. Essex Village, Connecticut

  • Median Property Value: $680,731 - up 8.7% over the past year.
  • Median Household income: $101,458
  • Population – 2,814

Essex Village is located in Middlesex County and is known for its historic New England village charm within the town of Essex. The small village sits along the Connecticut River, which offers scenic views and opportunities to enjoy water recreational activities. Most of the residents of Essex Village have gainful employment with high-paying jobs. Essex Village is a highly desirable community in which to live and one of the richest towns in CT.

13. Redding, Connecticut

  • Median Property Value:  $778,283 -up 10.2% over the past year.
  • Median Household income: $165,391
  • Population – 8,787

Redding is a small, tony, upper-middle-class town located in Fairfield County, which shares its border with Danbury and Georgetown. Redding, which is only about 60 miles from New York City, is known for its scenic and natural beauty, including the Saugatuck Reservoir and Devil's Den Preserve and many movie shoot locations. The town’s schools are rated excellent, and there are private school options as well; its library’s first books were donated by one of the famous residents, Samuel Clemens/Mark Twain.  In 2012, Connecticut ranked Redding as the state’s second-best town in which to reside; a few years earlier, CNN Money selected it as the 4th best place in the country!

12 Fairfield, Connecticut

  • Median Property Value: $800,485 -up 11.9% over the past year.
  • Median Household income: $165,316
  • Population – 61,512

Fairfield, which is situated about 50 miles from NYC, is a moderate-sized city in Connecticut’s Fairfield County that ranks among the richest towns in CT. Fairfield is situated along the Long Island Sound, providing its residents/visitors with access to coastal areas that lead to the Atlantic Ocean. Redding’s streets are safe, and despite the size of the town, there are many venues for recreation, boutiques, restaurants, cafes, and more. Test performance scores and the quality of Fairfield’s public schools are highly rated. Fairfield maintains several public beaches (for example, Jennings Beach and Penfield Beach) with access to the Long Island Sound.

11. Easton, Connecticut

  • Median Property Value: $845,457 -up 9.9% over the past year.
  • Median Household income: $181,934
  • Population – 7,630

Easton is a small, affluent community that is considered a part of the Greater Bridgeport area in southwestern Connecticut, with Redding located to the north and Weston to the west. The small town is rich with history and places on the National Historic Register. The town, which many consider an Equestrian Community, is characterized by wooded areas and streams and is home to the Aspetuck Land Trust, a non-profit committed to preserving the town’s open space. Helen Keller’s Easton Home is still the same as when she lived in the now exclusive town about an hour from midtown New York.

10. Ridgefield, Connecticut

  • Median Property Value: $857,553 -  up 13.2% over the past year.
  • Median Household income: $129,919
  • Population – 7,228

Ridgefield is situated in southwest Connecticut’s Fairfield County at Berkshire Mountains foothills – only about an honor from New York City and accessible, like most of this part of the state, with ease by Metro North Railway Service, mostly by the convenient access offered by Metro North into Grand Central Station in NYC. The town is near Redding and Danbury but also abuts North Salem, New York, which is a part of Westchester County. The town is surrounded by natural beauty, with outdoor recreational opportunities for enthusiasts to explore hiking trails, nature preserves, and scenic landscapes. The Ridgefield Rail Trail is a popular spot for walking and biking.

9. Wilton, Connecticut

  • Median Property Value: 1,022,886  - up 8.9% over the past year.
  • Median Household income: $234,545
  • Population – 18,457

Wilton is the first town on the list of the richest towns in Connecticut to have a median home sales price that tops $1 million and a median household income that tops $200,000/year. It is bordered by the towns of Ridgefield, Redding, Weston, Norwalk, and New The city is a hop, skip, and jump from New York City, which offers residents all the amenities of the big city without the negative impacts of a large urban area. Wilton has impressive parks and recreational programs to provide residents with many open spaces and public events. Wilton is also home to the state's only national historic site, Weir Farm.

8. Weston, Connecticut

  • Median Property Value: $1,120,040 - up 7.8% over the past year.
  • Median Household income: $220,754
  • Population – 10,278

Weston is situated in southwestern Connecticut in Fairfield County, bordered by Westport, Easton, and Wilton. About 20% of its residents commute 40-plus miles to NYC. The town, which has been ranked among the safest in the nation and the state of Connecticut, has implemented zoning regulations to maintain its suburban character, as it is its objective to keep 25% of the town dedicated to open spaces. Weston High Public Schools are known for its academic achievements and quality of education, with the high school ranked the second best in the state by U.S. News and World Report in April 2019.

7. Southport, Connecticut

  • Median Property Value:  $1,202,003 - up 11.8% over the past year.
  • Median Household income: $161,642
  • Population – 1,710

Southport, which was settled in the 1600s, boasts a well-preserved historic character with colonial-era architecture and tree-lined streets characterized by fluent residential flair. Southport is near NYC in Fairfield County, with its southern border along the Long Island Sound and near the Sasco Brook and Mill River. The town’s library was founded by two prominent residents in the 1880s – with a special collection that includes the first cookbook ever printed – circa 1475. Residents are offered an easy NYC commute as they are served by the New Haven line of Metro North and are even offered limited buses to the Big Apple.

6. COS COB, Connecticut

  • Median Property Value: $1,400,000 – N/A.
  • Median Household income: $138,125
  • Population – 7,065

Cos Cob is situated in the southern part of Greenwich, along the Connecticut Shoreline adjacent to the Long Island Sound and on the shores of the Mianus River. It is approximately 30 miles northeast of New York City. Cos Cob was home to the Cos Cob art colony, a community of American Impressionist artists that found their way from nearby New York City.  Cos Cob neighborhoods consist of residential areas that include a diverse mixture of waterfront estates, modern homes, and historic residences, among others. In 2015, Forbes Magazine ranked Cos Cob as the 287th wealthiest community in the nation. Where would it fall today?

5. Westport, Connecticut

  • Median Property Value: $1,633,345 - up 8.7% over the past year.
  • Median Household income: $236,892
  • Population – 27,141

Westport ranks among the five most affluent and richest towns in C.T. Westport, which sits along the state’s Gold Coast/Long Island Sound, is home to many affluent residents who have access to yachts,  private country clubs, and unsullied beaches. Westport's public school system has been top-ranked in the state and often falls within the top twenty of the nation’s top public school districts.  The town is home to the Westport Country Playhouse, founded nearly a century ago but re-emerged in the 1960s when Paul Newman moved to the town, as well as several other museums.

4. New Canaan, Connecticut

  • Median Property Value: $1,730,896 - up 8% over the past year.
  • Median Household income: $190,227
  • Population – 20,622

New Canaan is located in southwest Connecticut, with a 40-minute commute to New York City from the town’s train station. New Canaan is bordered by Darien, Wilton Stamford, and Norwalk. New Canaan offers a variety of residence types, including single-family homes, palatial estates, and upscale modern neighborhoods. Residents of New Canaan will find boutiques, local eateries, and upscale dining options. Waveny Park, a large and well-maintained park, provides residents and visitors with sports fields, walking trails, and a historic mansion.

3. Darien, Connecticut

  • Median Property Value: $1,835,090 - up 7.9% over the past year.
  • Median Household income: $250,001
  • Population – 21,499

Darien, located on Connecticut’s Gold Coast and known as the smallest town in the area, holds the title of being the richest town in Connecticut. Its affluence stems from a combination of factors, including its location near prosperous neighborhoods and its picturesque coastal setting. With a remarkable me­dian household income of $250,001, Darien is home­ to a significant number of affluent reside­nts. Moreover, in June 2012, Darie­n was acknowledged by 24/7 Wall St. as the 10th we­althiest school district in the United State­s—an accolade that further underscores its prosperity and access to abundant resources.

2. Old Greenwich, Connecticut

  • Median Property Value: $1,907,737 - up 7.1% over the past year.
  • Median Household income: $234,152
  • Population – 6,980

Old Greenwich, Connecticut refers to a picturesque and charming seaside/coastal neighborhood that is part of the Town of Greenwich. Old Greenwich is characterized by natural scenic beauty, including tree-lined streets, water views, and well-maintained open green spaces. The town’s pricey real estate includes beautiful waterfront homes that have private beaches and access to boats/yachts. The town, which is only 37 miles from New York City, offers quaint boutiques and elite dining venues. This year-round hamlet has a staggering median household income of $234,152,

1. Riverside, Connecticut

  • Median Property Value: $2,121,922 - up 7.2% over the past year.
  • Median Household income: $250,000
  • Population – 9,130

Suburbs 101 notes that Riverside, Connecticut, is a wealthy suburb/section within the Town of Greenwich with opulent residences, seriously robust incomes, and the benefit of “location, location. location.” As such, Riverside holds the distinction of topping the 2023 list of the richest towns in Connecticut, with a median property value that now exceeds $2.1 million. With plenty of shopping and fine dining venues and a short Metro North commute to Grand Central Station, Riverside is a great place to live in Connecticut if you have the funds.

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Allen Lee

Written by Allen Lee

Allen Lee is a Toronto-based freelance writer who studied business in school but has since turned to other pursuits. He spends more time than is perhaps wise with his eyes fixed on a screen either reading history books, keeping up with international news, or playing the latest releases on the Steam platform, which serve as the subject matter for much of his writing output. Currently, Lee is practicing the smidgen of Chinese that he picked up while visiting the Chinese mainland in hopes of someday being able to read certain historical texts in their original language.

Read more posts by Allen Lee

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