Five towns on the Sound
Where to look, what it costs and how long the train takes, from people who live here. Prices are what we see most homes trade for, not the extremes.
Westport
Beach town with a theater habit
Compo Beach in summer, the Saugatuck River all year, and a downtown of independent shops and restaurants that stays busy well past Labor Day. Lots range from tidy beach-area cottages to wooded acre parcels north of the Merritt.
- Schools
- Westport Public Schools, with one high school at the center of town life.
- Commute
- Saugatuck and Greens Farms stations on Metro-North. About 65 to 75 minutes to Grand Central.
- Price range
- Most single-family homes trade between $1.1M and $4M.
Fairfield
Village greens and beach roads
Two towns in one: the beach-road cottages and university energy near the shore, and the quiet Greek Revival streets of Southport village. Fairfield has more variety at more price points than anywhere else on our list.
- Schools
- Fairfield Public Schools, with two public high schools and several well-regarded private options nearby.
- Commute
- Fairfield, Fairfield Metro and Southport stations. About 75 to 85 minutes to Grand Central.
- Price range
- Most single-family homes trade between $700k and $2.5M.
Darien
Small, leafy and close-knit
A compact town with a walkable Post Road center, beach and boating clubs along Noroton Bay, and quiet cul-de-sacs where children still ride bikes to school. Inventory is thin, so good houses move quickly.
- Schools
- Darien Public Schools, with a single high school that draws families from across the region.
- Commute
- Darien and Noroton Heights stations. About 55 to 65 minutes to Grand Central.
- Price range
- Most single-family homes trade between $1.5M and $5M.
Norwalk
Harbor villages and mill lofts
The most varied town we cover: SoNo’s lofts and restaurants, Rowayton’s harbor village, and the wooded hills of Silvermine. It is where many of our first-time buyers find a way into the shoreline.
- Schools
- Norwalk Public Schools, with several magnet and choice programs alongside the neighborhood schools.
- Commute
- South Norwalk, East Norwalk and Rowayton stations. About 55 to 65 minutes to Grand Central.
- Price range
- Condos from about $400k; most single-family homes between $650k and $1.8M.
Greenwich
Closest to the city
Greenwich Avenue’s shops and restaurants, the small harbors of Cos Cob and Old Greenwich, and estate country to the north with stone walls and long driveways. Buyers here often trade a few minutes of commute for a lot more land.
- Schools
- Greenwich Public Schools, plus one of the densest clusters of private schools in the state.
- Commute
- Four stations from Cos Cob to Old Greenwich. About 45 to 55 minutes to Grand Central.
- Price range
- Condos from about $700k; most single-family homes between $1.8M and $8M.