Greenwich

Suburban Coastal Beaches

Population: 62k

Cost of Living: Very High

Near Train: Yes (Metro-North Railroad (New Haven Line) Line)

Near Bus: Yes (Greenwich Transit District (local buses) and Connecticut Transit Line)

Greenwich sits at Connecticut's southwestern edge, where Westchester County ends and the Gold Coast begins—often mistaken for a New York suburb, yet it operates as its own municipality with distinct character. The town straddles two identities: a waterfront community along Long Island Sound with deep maritime roots, and an affluent residential enclave known for estates, manicured neighborhoods, and strong schools. The downtown area along Greenwich Avenue hosts independent retailers, restaurants, and galleries alongside national chains. Belle Haven, the peninsula neighborhood, features some of the region's most expensive waterfront properties. Round Hill, Conyers Farm, and other established residential areas offer tree-lined streets and substantial homes on generous lots. The town maintains working marinas, public beaches, and parks including Tod's Point, a barrier beach with swimming and walking trails. Greenwich's economy historically centered on finance and commuting professionals; many residents work in Manhattan via Metro-North or car. The public school system ranks among Connecticut's strongest, a major draw for families. The town's tax base supports extensive municipal services and infrastructure.

VRBO Vacation Rentals
Learn More

With over 2 million bookable vacation rentals, Vrbo connects homeowners with families and vacationers looking for something more than a hotel for their trip. The Vrbo community offers families an array of rental property types such as condos, cabins, lake rentals, beach houses, and more. Discover properties in destinations that everyone dreams of visiting.

VRBO Vacation Rentals

Keep reading. It is free.