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The Best Places for Young Families in Connecticut

If you’re starting a family and are also looking to buy a home, you probably already have a very different wishlist from your pre-family days. Now it’s likely you’re looking for affordable homes, reasonable mortgages, excellent schools, neighborhoods filled with other families and a commute that may not be zen-like, but still offers plenty of time with the kids.

In Connecticut, families looking for a place to call home have no shortage of communities to choose from, but they may have to make concessions in some areas to gain what they’re looking for, such as lower housing costs, in others. If you’re considering Connecticut for your next home, read on to see how researchers at LendingTree compiled a list of the best places for young families.

Key takeaways

  • Cheshire Village is the best place to raise a family in Connecticut, with a final score of 74.3.
  • Northwest Harwinton and Riverside take the second and third spots, with final scores of 71.4 and 71.0, respectively.
  • On the other end of the list, we found Putnam to be the most challenging place for young families in Connecticut, with a final score of 43.5.
  • Winsted and Hartford finished out the bottom three towns on our list, with final scores of 47.4 and 48.8 respectively.

The top 10 cities to live in Connecticut

No. 1: Cheshire Village

Topping our list is the central Connecticut village of Cheshire, part of the larger town of Cheshire. With an estimated 6,251 residents, Cheshire has less than a 1% unemployment rate among 25- to 44-year-olds, strong schools and an exceedingly high homeownership rate for families with children, 96.4%.

As with most Connecticut cities on our overall list, housing costs here are very high; but, compared to income, they make Cheshire one of the more affordable places on the top 10 list. That’s because housing costs a median of $1,423 per month, less than in some communities further down the list. With a relatively short commute of 23 minutes and proximity to both New Haven and Hartford, the state capital, Cheshire Village offers residents both small-town living and city access.

No. 2: Northwest Harwinton

This small community is part of rural Harwinton in Litchfield County, and it earned a top 10 ranking with a winning combination of some of the qualities young families value most. Despite a median housing cost of $1,389 monthly, close to 98% of families with children own homes — the highest homeownership rate we found in the state. Families can find good schools here, and job prospects also appear excellent. That may be because Northwest Harwinton is only about 20 miles from Interstate 84, a major eastern U.S. thoroughfare that also links Connecticut cities such as Danbury, Waterbury and Hartford.

No. 3: Riverside

With an estimated population of 8,385, Riverside is a part of the town Greenwich in southwestern Fairfield County. It ranks third on our 10 best list, but the median housing cost of $3,140 per month will most likely be too high for families just starting out, even if it is in line with high local household incomes. Almost half of Riverside households have children, one of the highest percentages for a top-ranked community. However, only 78% of those families own homes, possibly because of the area’s high prices. Living here means proximity to New York City, about an hour-long train ride away.

No. 4: North Haven

With an estimated population of 23,877, North Haven has a small-town feel but is one of the larger communities on our top 10 list. Residents enjoy a short commute (about 22 minutes on average), strong schools and relatively more affordable housing costs, a median of $1,656 monthly. Meanwhile, North Haven’s location within the larger New Haven area means residents have access to nearby cultural draws, such as Yale University, and the beaches and waterfront life of Long Island Sound.

No. 5: Durham

Coming in fifth on this list is the rural town of Durham, located midway between two of Connecticut’s largest cities, Hartford and New Haven. With a monthly median of $1,801, housing costs in Durham are higher than they are in North Haven, but more than a third of families have children here. This town is known for its annual Durham Fair, an agricultural event that draws more than 200,000 visitors every fall. The homeownership rate for families is a high 85.4%, and both local job prospects and schools appear excellent.

No. 6: Darien

Another town in affluent Fairfield County, Darien is a big draw for families. More than 52% of households have children, and 89% of those households own homes, despite a median housing cost of $3,705 per month, the highest on our list. In Darien, which has a population of about 21,000, the median household income is the same as it is in Riverside and eighth-ranked Old Greenwich ($250,001 per year). Like many towns in Fairfield County, this is a commuter-friendly place for anyone who works in New York City, but it also offers fast access to both Stamford and Norwalk in Connecticut.

No. 7: Ridgefield

Ridgefield may be in Fairfield County, but with a median housing cost of $2,309 per month, it has far lower housing costs than some of its neighbors, such as Darien and Riverside. Household income is high in this community, which is a subset of the larger Ridgefield town and has an estimated 8,000 residents, but Ridgefield has a lower percentage of families with children, about 38%. Still, low unemployment, good schools and a location relatively near to New York help explain why this community is a top 10 pick.

No. 8: Old Greenwich

Located in the affluent town of Greenwich, Old Greenwich is a smaller neighborhood with an estimated population of 6,860. It has the same, very high median household income as do Riverside and Darien, but housing costs that fall in about the middle of those two cities. Almost half of households have children. Family amenities here include quality schools, low unemployment, a town beach and a water-sports-friendly location on Long Island Sound. Old Greenwich is also just more than an hour from New York City by train, a popular option with commuters.

No. 9: Conning Towers Nautilus Park

This small, unincorporated neighborhood is part of Groton, a town in southeastern Connecticut that is also home to Naval Submarine Base New London, a major Navy submarine base. The median housing cost here is $1,591 per month, so it’s one of the most affordable places on our list. The average commute time is short — about 14 minutes — probably due to the presence of the naval base and major employers, such as Pfizer. Over half of households in this area have children, but only 4% of those families own homes, most likely due to the large number of military employees. Groton is on Connecticut’s shoreline and is close to family-friendly destinations, such as Mystic Aquarium and Mystic Seaport.

No. 10: Kensington

Located in the center of Connecticut, Kensington is within reasonable distance of Hartford and smaller cities, such as New Britain and Meriden. Officially, it’s part of Berlin and houses that town’s municipal offices. Kensington has the most affordable housing for a top 10 city on our list, with a median monthly cost of $1,358. Meanwhile, household income is high, which helps explain why more than 96% of families with children here own homes.

Understanding the rankings

We chose seven indicators to rank cities and towns with above 2,435 people in Connecticut for how good they are for young families, which were then scored to create an overall ranking of the best places for young families. The seven indicators we used were:

  • Median family income: Money isn’t everything, but a place with high family incomes suggests a place with good job opportunities and a community with more resources.
  • Median monthly housing costs for all households: For families already dealing with new child care expenses, reasonably affordable housing is important.
  • Homeownership rate of families with children: This indicates where homeownership is both more common and — perhaps important for a family looking to buy — more practical.
  • Unemployment rate of 25- to 44-year-olds: This indicates where the job market is healthy and suggests a higher quality of life locally. We focused on 25- to 44-year-olds in particular to capture the most common ages for parents of young families.
  • Percentage of 16- to 19-year-olds not enrolled or graduated from high school: To estimate high school graduation rates and, therefore, school quality, we calculated the percentage of older teenagers who were not in high school yet had no high school degree. This number is not the actual high school dropout rate, but is well-correlated.
  • Average commute time: Shorter commutes mean less stressed workers who have more time to spend with their families.
  • Percentage of households that have children: A community with more children means that other families have already decided it’s attractive. It also usually means more educational and recreational activities suitable for children and their parents and that residents are concerned about policies that benefit families with kids.


Analysts used data from the 2017 5-Year American Community Survey by the U.S. Census. Each of the seven metrics was given a value according to its relative location between the highest and lowest values. The values were then summed and divided by seven for an equal weighting. The analysis was limited to Census-designated places with populations of at least 2,435.


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