Greenwich vs Darien: Which Town is Right for Your Family?

Both towns hug the Long Island Sound coastline. You get waterfront access, coastal breezes, and that New England shoreline charm. Greenwich sits roughly 30 miles from Manhattan. Darien is about 37 miles out.

Here is why the distance matters. Greenwich operates four Metro-North stations: Old Greenwich, Riverside, Cos Cob, and the main Greenwich station. Express trains reach Grand Central in about 45 minutes. Darien runs two stations (Darien and Noroton Heights) with express trains clocking in around 50 minutes.

I've watched families choose Greenwich purely for those extra train options. When you have four stations spread across town, most homes sit within a quick walk or five-minute drive of a platform. Darien's two stations work well, but you might need a longer drive depending on your neighborhood.

Both towns connect to I-95 and the Merritt Parkway (Route 15). Driving access is straightforward from either location. Greenwich puts you closer to Stamford's corporate offices and restaurants. Darien sits nicely between Greenwich and Norwalk, giving you options in both directions.

That five-minute commute difference adds up. If you ride the train five days a week, you're looking at roughly 20 extra minutes weekly, or about 17 hours annually. Some people shrug this off. Others find Greenwich's proximity worth the premium.

Let's break it down: Greenwich gives you more station choices and a shorter ride. Darien still delivers solid train access with a slightly longer commute. Your choice depends on how much those minutes matter to your daily routine.

Source: Blaise Punturo Real Estate, "Greenwich vs Darien 2025: Schools, Commute, Neighborhoods, Homes," 2025.View source

Greenwich feels more diverse. You get everything from bustling downtown areas to quiet waterfront communities like Old Greenwich and Riverside. The town's larger size means more variety in neighborhoods and lifestyles.

Greenwich's downtown area buzzes with activity. Restaurants, shops, and services create a vibrant center. Neighborhoods like Belle Haven and Cos Cob each have distinct personalities. You can find your niche within the larger town.

Darien has a tighter, more cohesive feel. The town is smaller, so neighborhoods feel closer together. You'll find family-friendly areas near schools and parks, plus coastal pockets that give you that beach town vibe.

Darien's community events bring people together. The town hosts festivals, farmers markets, and local gatherings that create connections. Parents often know each other through school activities and sports. This creates that small-town feel within a wealthy suburb.

I've noticed Greenwich attracts people who want options. You might want an in-town condo one year and a waterfront estate the next. Darien tends to draw families who want that classic suburban community where everyone knows their neighbors. The choice depends on whether you value variety or intimacy.

Source: Blaise Punturo Real Estate, "Greenwich vs Darien 2025: Schools, Commute, Neighborhoods, Homes," 2025.

Greenwich offers more variety. You'll find in-town condominiums, historic homes, waterfront estates, and everything in between. The market caters to different budgets and preferences.

Greenwich's housing ranges from $500,000 condos to multi-million dollar waterfront properties. This variety means first-time buyers and established families both find options. Neighborhoods like Riverside and Old Greenwich command premium prices for their coastal locations.

Darien focuses on single-family homes, many with that traditional New England look. Think colonial and Cape Cod styles on spacious lots. The housing stock is more uniform, which some people prefer.

Darien's homes typically start around $800,000 and go up from there. The market skews toward single-family properties on larger lots. This creates a more consistent neighborhood aesthetic. Buyers who want architectural variety might find Greenwich more appealing.

Both towns rank among the wealthiest in America. Greenwich's Old Greenwich section ranks as the 16th richest town nationally. Darien also sits in the top 10. Property taxes in Greenwich tend to be slightly lower, though the difference isn't dramatic. On a $2 million home, you might save a few thousand dollars per year in Greenwich.

Sources: Blaise Punturo Real Estate, "Greenwich vs Darien 2025"; Sivo Blog, "Richest CT Towns," 2025.

Both school districts perform well. Greenwich High School serves around 2,633 students with a 13:1 student-teacher ratio. The graduation rate sits at 94%, with 64% proficient in math and 79% in reading.

Greenwich High offers over 200 courses, including 30 Advanced Placement options. The school fields competitive sports teams and supports extensive arts programs. Students benefit from the larger pool of peers and resources.

Darien High School is smaller, with about 1,398 students and an 11:1 ratio. The graduation rate is 99% or higher, with 76% proficient in math and 89% in reading. The smaller size can mean more individual attention.

Darien High offers strong academics with a focus on college preparation. The smaller student body creates closer relationships between teachers and students. Parents often report feeling more connected to the school community.

Both districts offer strong academic programs and extracurricular activities. Greenwich's larger size means more course variety and program options. Darien's smaller size can create a tighter community feel within the schools. The choice depends on whether your child thrives in a larger environment or prefers more personal attention.

Source: Public School Review, "Greenwich High School vs Darien High School," 2025.

Both towns are expensive. You're paying for excellent schools, safe neighborhoods, and proximity to NYC. Greenwich property taxes tend to be slightly lower, which can matter on a high-value home.

Property taxes in Greenwich average around 1.1% of assessed value. Darien's rates run slightly higher, around 1.2%. On a $2 million home, that's roughly $2,000 per year difference. Not huge, but it adds up over time.

Housing costs vary by neighborhood in both towns. Greenwich's variety means you might find more entry points, from condos to estates. Darien's focus on single-family homes means the market is more consistent.

Living expenses beyond housing are similar. Groceries, restaurants, and services cost about the same in both towns. Both have excellent healthcare facilities nearby. The real cost difference comes down to housing choices and property taxes.

The real difference isn't in the numbers. It's in what you get for your money. Greenwich offers more variety and a larger town center. Darien offers that tight-knit community feel. Both cost a lot, but the lifestyle differs. You're choosing between options and intimacy.