Drone image of boats in Southport, Connecticut

Connecticut’s 19 Richest Cities and Towns

Richest Cities in Connecticut

Connecticut, a state renowned for its esteemed educational institutions and close proximity to the financial powerhouse of New York City, also lays claim to a number of opulent cities and towns. These pockets of affluence mirror the economic vibrancy and historical importance deeply ingrained in the Constitution State. 

In this article, we will travel through Connecticut’s cities and towns, beginning with notable but less prosperous towns and progressing to Connecticut’s financial apex. Economic growth, communal values, strategic advantages, and lifestyle, educational, and cultural options distinguish each location. As we examine Connecticut’s 19 richest cities and towns, we will examine their finances, quality of life, and opportunities for homeowners and renters.

You can also find out the richest cities in Maryland here.

19. Madison, CT: $115,766 Median Household Income

Madison, situated gracefully on the Connecticut shoreline, embodies coastal New England life. Boasting a median household income of $115,766, it serves as a gateway to financial security and a premium standard of living. Madison’s prosperity is often attributed to its excellent schools and the many professional opportunities in nearby cities.

Many of its residents discover employment in the adjacent city of New Haven or undertake the manageable commute to Hartford or New York City. Furthermore, the town’s real estate market thrives thanks to its picturesque beaches, historical architectural gems, and a community-focused lifestyle, all of which magnetize a financially well-off populace.

The local economy is supported by small businesses, healthcare institutions, and innovative startups that value Madison’s location and educated workforce.

18. Guilford, CT: $116,250 Median Household Income

Guilford, with a median household income of $116,250, blends historical preservation and modern affluence. Residents of Guilford often feel like they are in a place with a lot of history. The well-kept 17th-century homes and the lively town green that dates back to 1639 are two examples. Due to its proximity to Yale University and other prestigious New Haven institutions, many residents work in academia, healthcare, or technology.

The real estate panorama here is diverse, offering an wide range of properties, from historic homes to modern condominiums, alluring a financially secure demographic that values the town’s fusion of history with modern comforts.

Local businesses, in tandem with a variety of recreational amenities, further enrich Guilford’s appealing living standards, cementing its position on our list of most affluent cities in Connecticut.

17. Woodbridge, CT: $117,614 Median Household Income

Woodbridge, with a median household income of $117,614, attracts professionals seeking residential peace. Its strategic location, a short drive from New Haven, provides access to diverse employment opportunities across sectors.

Professionals and their families are drawn to the town’s well-kept public spaces, prestigious schools, and strong community. This is what makes Woodbridge worthy as one of the richest cities in Connecticut. Residential neighborhoods offer a peaceful escape from urban life while remaining connected. Woodbridge’s real estate market attracts affluent individuals due to the presence of spacious homes and well-maintained neighborhoods.

Furthermore, the local government’s focus on nurturing a sustainable and environmentally conscious community renders Woodbridge an enticing destination for those with comfortable incomes seeking a wholesome community to call home.

16. Easton, CT: $120,357 Median Household Income

Easton, with a median household income of $120,357, has a charming rural feel while being close to vibrant urban centers. The town represents Connecticut’s lush countryside with the modern amenities wealthy residents want.

Many of its residents find employment in neighboring cities such as Bridgeport and Stamford, or even within the nearby state of New York, returning to the peaceful and spacious residences that the city provides. The town’s real estate market mirrors its affluence, presenting a range of expansive homes nestled amidst the natural surroundings.

Also, Easton’s dedication to preserving its historical and natural heritage attracts a demographic that values a peaceful living environment, strong education, and community support. The fusion of rural allure and accessibility to urban opportunities encapsulates why Easton secures its place in the upper echelons of affluent towns. 

15. Fairfield, CT: $122,519 Median Household Income

Featuring a median household income of $122,519, Fairfield blends history, modern conveniences, and a promising economy. Its strategic placement along the Long Island Sound and its proximity to New York City have always been its key strengths, attracting professionals from diverse sectors.

The town’s real estate landscape encompasses a diverse array of premium waterfront properties, contemporary urban residences, and historic homes, providing an appealing cluster of options for affluent buyers and renters.

Due to its well-rounded educational institutions and dynamic local economy driven by small businesses, retail, and nearby corporate centers, it attracts financially secure families and individuals.

The plethora of recreational amenities, cultural happenings, and a tightly-knit community further elevate Fairfield’s charm, rendering it a highly sought-after locale for those in search of a prosperous and engaging living experience.

14. Redding, CT: $126,250 Median Household Income

Redding, with its median household income at an impressive $126,250, epitomizes a lifestyle often associated with serenity, community involvement, and a premium living standard. The town is an irresistible draw for well-off individuals who treasure its scenic landscapes, exceptional school system, and the wealth of outdoor recreational opportunities it presents.

Redding’s proximity to employment hubs in Fairfield County and New York City further enhances its appeal to professionals seeking a harmonious work-life equilibrium. Elegant homes in lush surroundings attract a demographic that values aesthetics and financial investment in Redding real estate.

Redding is also one of Connecticut’s wealthiest towns due to its commitment to rural charm and modern amenities. Rich residents love its natural beauty, economic security, and supportive community.

13. Ridgefield, CT: $130,000 Median Household Income

Moving up the list of the richest cities in Connecticut we come to Ridgefield. Boasting a median household income of $130,000, Ridgefield stands as the embodiment of a thriving suburban enclave with a rich historical tapestry. High-earners in finance, technology, and healthcare choose this town for its quality of life and economic success.

The real estate market here is notably dynamic, providing a plethora of housing options, from opulent estates to contemporary residences, all set against the scenic backdrop of rolling hills and meticulously-maintained public spaces. Ridgefield’s educational institutions are top-tier, further amplifying the town’s appeal to affluent families.

Moreover, a flourishing cultural scene with art galleries, theaters, and a multitude of local events enriches community life, making Ridgefield not just an economically prosperous town but also a culturally vibrant one.

12. Simsbury, CT: $130,175 Median Household Income

Simsbury, enjoying a slight edge with a median household income of $130,175, epitomizes suburban prosperity intertwined with a robust community ethos.

Nestled in the Farmington Valley, Simsbury harmoniously blends historical landmarks with modern conveniences, making it a magnet for a demographic that cherishes both the richness of the past and the comforts of the present. The town’s real estate market is vibrant, offering an array of homes tailored to a well-off clientele.

Proximity to Hartford brings forth a multitude of employment opportunities for residents, while the local economy thrives through a mix of small businesses, retail establishments, and service providers. Simsbury’s school system is also very well known and respected, which brings in families who value a strong academic foundation for their children.

Access to recreational facilities and a myriad of community events further elevate Simsbury’s quality of life, solidifying its position among the affluent towns in Connecticut.

11. Glastonbury, CT: $132,500 Median Household Income

Glastonbury, boasting a median household income of $132,500, unravels a compelling story of economic expansion, top-tier education, and an alluring suburban lifestyle. Its strategic proximity to Hartford serves as a gateway to numerous professional opportunities, attracting a financially secure population.

The real estate landscape in Glastonbury is diverse, offering an array of options, from swank residences to modern condominiums, appealing to a wide spectrum of affluent preferences. The local economy thrives with the vigor of small businesses, retail outlets, and a burgeoning tech sector, further enhancing the town’s desirability.

Glastonbury’s educational institutions are held in high regard, rendering it a sought-after destination for families. A vibrant community with many local events and recreational activities gives residents a deep sense of belonging, cementing Glastonbury’s place among Connecticut’s affluent towns.

10. New Canaan, CT: $140,963 Median Household Income

New Canaan, with a median household income of $140,963, combines suburban elegance with opulence. New Canaan attracts classy residents with its architectural heritage and luxurious lifestyle. The town’s strategic proximity to New York City is a notable advantage, offering residents a multitude of employment opportunities and cultural experiences.

The real estate landscape mirrors its affluence, showcasing sumptuous residences, modern architectural wonders, and meticulously kept neighborhoods. New Canaan’s schools rank among the top in the state, making it an even more appealing destination for affluent families.

There are many businesses in New Canaan that help the economy, and the cultural scene is thriving with art galleries, theaters, and community events that make people’s lives better. This makes New Canaan one of the most wealthy suburban areas in Connecticut.

9. Wilton, CT: $152,794 Median Household Income

Wilton, boasting a median household income of $152,794, stands as a symbol of suburban affluence seamlessly fused with a tranquil, nature-rich environment. Its strategic proximity to New York City and Stamford unfolds a spectrum of employment opportunities for its residents, spanning finance, technology, and more.

The town’s real estate market offers luxury estates and modern family homes in picturesque settings. Wilton’s schools are often ranked among Connecticut’s best, attracting families who value academics.

The community here is vibrant and participatory, offering a multitude of local events, recreational programs, and cultural activities that enhance the quality of life. The amalgamation of financial stability, educational excellence, and a close-knit community accentuates Wilton’s allure to the affluent demographic.

8. West Hartford, CT: $153,657 Median Household Income

West Hartford, with a median household income of $153,657, radiates economic vitality and a rich cultural scene. Being close to Hartford, the town is full of diverse, well-educated professionals in the academic, healthcare, and insurance sectors.

The real estate market in West Hartford is dynamic, offering a spectrum of housing options, from historic homes to contemporary condominiums, to meet the discerning tastes of the affluent. Top-rated schools and a bustling downtown with shops, restaurants, and cultural venues give West Hartford a modern edge.

Additionally, a plethora of parks and recreational facilities contribute to an enhanced quality of life, making it a sought-after destination for wealthy individuals and families seeking a harmonious and culturally enriched living environment.

7. Greenwich, CT: $154,502 Median Household Income

Greenwich is wealthy and prestigious, with a median household income of $154,502. Wealthy people, many of whom work in finance, prefer its Long Island Sound location near New York City.

The real estate market here is among the most luxurious in Connecticut, featuring grand estates, waterfront properties, and modern architectural masterpieces. Greenwich’s educational institutions are exemplary, and the town also hosts a variety of exclusive social clubs and recreational facilities.

The cultural richness, from art galleries to theater performances, further enhances the allure of Greenwich, making it not only a financially prosperous locale but also a one of the best places for black families to live in Connecticut.

6. Riverside, CT: $215,791 Median Household Income

Riverside, with a median household income of $215,791, sees a huge jump in household income on this list of the richest cities in Connecticut.

Riverside offers an oasis of suburban opulence in the calm waters of the Long Island Sound. As a part of Greenwich, it shares in the affluence and reputation the area is known for. The proximity to New York City opens up numerous professional opportunities, particularly in high-paying sectors like finance and law.

The real estate market in Riverside is luxurious, featuring homes with waterfront views and modern amenities. Its businesses and proximity to major economic hubs support its thriving economy and high-quality education. Riverside combines scenic beauty, economic success, and educational excellence, making it a highly desired community for the affluent in search of a peaceful yet prosperous living environment.

5. Westport, CT: $222,535 Median Household Income

Westport, with a median household income of $222,535, epitomizes coastal prosperity in Connecticut. This shoreline town has always been popular with wealthy families and individuals due to its beauty and proximity to New York City. Westport has many lucrative finance, law, and creative jobs locally and in nearby urban hubs.

The real estate market in Westport is thriving, featuring a wide array of homes, from waterfront estates to modern architectural wonders, reflecting the financial success of its residents. The town’s educational system is highly respected, and the abundance of cultural and recreational offerings, including beaches, parks, theaters, and art galleries, adds to the richness of life in Westport.

The perfect blend of a robust economy, exceptional education, and a vibrant cultural scene underscores Westport’s allure for the affluent demographic.

4. Old Greenwich, CT: $222,794 Median Household Income

Old Greenwich’s median household income of $222,794 exemplifies a peaceful, prosperous lifestyle. Situated along the Long Island Sound and within the town of Greenwich, this neighborhood offers a serene coastal living experience while maintaining proximity to the financial centers of Greenwich and New York City.

Many residents are high-earning professionals with careers in lucrative sectors like finance and real estate. Old Greenwich real estate is known for grand homes with waterfront and garden views.

The educational institutions here are of top-notch quality, ensuring an exceptional academic foundation for the younger generation. With a community-focused atmosphere and a range of recreational and cultural activities, Old Greenwich stands out as an attractive destination for affluent individuals in search of a harmonious blend of prosperity, education, and quality of life.

3. Darien, CT: $232,523 Median Household Income

Darien, with a median household income of $232,523, stands out as one of Connecticut’s prime examples of affluent living. Its strategic location between the cities of Stamford and Norwalk, along with easy access to New York City, opens the door to numerous professional opportunities for its well-off residents.

Its real estate market reflects its prosperity, with luxury homes, condos, and waterfront properties. Families that value a good education will like this state’s top education system. Recreational facilities, clubs, and cultural events also make the town a vibrant social scene for a well-rounded lifestyle.

The harmonious blend of economic vitality, educational excellence, and social involvement positions Darien as a sought-after destination for the affluent, offering a fulfilling and prosperous living environment.

2. Weston, CT: $222,535 Median Household Income

Weston, with an identical median household income of $222,535 to Westport, offers a different kind of charm, nestled amidst lush hills and serene landscapes. It serves as a peaceful retreat for those with successful careers in nearby cities like New York and Stamford.

The real estate market in Weston is thriving, with a variety of luxurious homes situated in tranquil, nature-filled settings. The town’s public schools have an excellent reputation, attracting well-off families who seek both academic excellence and a peaceful living environment for their children. Weston has a close-knit liberal community, and its commitment to maintaining a rural charm while providing modern amenities creates a unique and attractive blend.

The combination of natural beauty, top-tier education, and proximity to urban centers defines Weston’s appeal to the financially prosperous demographic.

1. Southport, CT: $310,831 Median Household Income

Southport, a picturesquely wealthy coastal village in Fairfield, has the highest median household income at $310,831, and is therefore the richest town in Connecticut. Southport’s allure is rooted in its scenic harbor, historic architecture, and serene atmosphere, all within a short commute to the bustling financial districts of New York City and Stamford.

The real estate market in Southport is thriving, featuring luxurious waterfront residences, historic estates, and modern homes, all catering to the affluent individuals and families who call this village home. The educational institutions in and around Southport are of the highest caliber, and the village’s proximity to cultural and recreational amenities in Fairfield County further elevates the quality of life.

Southport epitomizes the pinnacle of affluent living in Connecticut, offering a harmonious fusion of economic prosperity, educational excellence, and a high-quality, tranquil living environment.


Connecticut, with its rich historical legacy, prime location near major urban centers, and wide range of lifestyle options, is home to a multitude of cities and towns where affluence thrives. From the peaceful, rural landscapes of places like Weston to the coastal elegance of Southport, each locale on this list reveals a unique story of economic prosperity intertwined with distinctive local characteristics. 

The high-quality education, numerous professional opportunities, and strong community spirit prevalent in these towns and cities further emphasize the appeal of calling these communities home. Whether one is drawn to New Canaan’s architectural heritage, Westport’s vibrant social scene, or Southport’s tranquil waterfronts, Connecticut’s affluent population is diverse and appealing.

By exploring these wealthy areas, one can learn more about Connecticut’s complex story of wealth, which makes it an appealing state for people looking for a better place to live, whether they own their own home or rent.

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