The Essential Greenwich CT Neighborhood Guide

It’s hard to miss the town of Greenwich, Connecticut’s charm and appeal. It certainly wasn’t lost on the Rockefellers, who began purchasing property here in the 1870s. Today they still own 141 acres in the area. With its close proximity to NYC, sparkling shoreline and quaint countryside Greenwich remains a wonderful place to call home. As a lifelong Greenwich resident turned Greenwich realtor, there’s no place else I’d rather call home. I’m breaking down everything you need to know about the area.

Perfectly nestled between Westchester County to the west and Stamford, CT to the east, Greenwich offers 32 miles of coastline to the south. Founded in 1640, the 50 square miles we know as Greenwich today wasn’t mapped out until 1730. Once rich farmland saturated with gristmills, the area saw a revolution with the introduction of the railroad in 1848. By the early 1900s, Greenwich served as a resort town for affluent New Yorkers wishing to escape city life.

Less than an hour’s commute to Grand Central, Greenwich still offers NYC commuters a small-town feel with sprawling green surroundings. It’s filled with nationally top-ranked schools and offers a rich cultural environment. And you don’t have to venture out to find premier shopping and dining options. If you haven’t yet discovered all that this town has to offer, read on for the breakdown of everything you need to know about Greenwich – by a lifelong native.

Greenwich, Ct Neighborhoods

The Greenwich area is divided into four main neighborhoods (listed from west to east):

Greenwich Proper
Cos Cob
Riverside
Old Greenwich

Let’s chat a little bit about each one and what they have to offer!

Greenwich CT Guide: Greenwich Proper

Greenwich Proper encompasses several smaller neighborhoods including Byram and Downtown Greenwich.

Byram offers some of the best value in the area – including low real estate taxes. It’s a great place to start your search if you’re on the hunt for a fantastic starter home. You’ll find more options for homes under a million dollars than anywhere else in Greenwich.

Byram sits at the westernmost part of Greenwich bordering New York. The quick 5-minute drive to Port Chester, NY means restaurants, shops and the Metro-North train station are easily accessible. Commuting to NYC is less than an hour away. Byram is also one of the most walkable areas of Greenwich. You’ll find plenty of sidewalks there – which isn’t the case in other areas of Greenwich. Do you love the beach? Byram features a family-friendly waterfront that is home to the Town of Greenwich pool. This impressive 6.8 million dollar facility offers a zero-entry pool, a lap pool, a kiddie pool and a splash pad. Fun for the whole family.

Downtown Greenwich, with its major shopping district, gives off a bustling cosmopolitan energy. You can find shops like Rag & Bone, Hermés, Alice + Olivia and Vince on Greenwich Ave – known locally as The Ave. Downtown Greenwich is home to world-class restaurants and hotels as well. Looking to soak in the arts? Stop into the Bruce Museum for over 15,000 permanent art pieces and a steady rotation of art installations.

The homes in downtown Greenwich are part of tight-knit communities. But if you’re looking for more space and land, it might not be the option for you.

Greenwich CT Guide: Cos Cob

If you’re an art enthusiast with a love for the unique, Cos Cob is right up your alley. Its origins are steeped in rich history. Impressionist painters like Childe Hassam, John H. Twachtman and Theodore Robinson were undeniably inspired by the landscape Cos Cob offers. 100 years ago visiting artists would spend all day with their easels propped up on the harbor capturing all the natural beauty.

A mere four and a half square miles, Cos Cob is home to Greenwich’s newest park – Cos Cob Park. Once the site of a power station, there you’ll find breathtaking views of the water and it’s a great spot to go yacht sighting.

The homes in the Cos Cob neighborhood range in size and style. No matter what’s on your residential must-have list, you’re sure to find a home that fits your needs in this quant neighborhood.

Greenwich CT Guide: Riverside

With a population of just over 8,000, Riverside is a gorgeous place to call home. Unlike other Greenwich neighborhoods, the area is mainly residential. Locals have a strong sense of community. You can often spot friendly residents on their morning jog.

Riverside has its own Metro-North station, making commuting to NYC a breeze in just under an hour. Are you a yacht owner? Riverside Yacht Club is located right on the tip of the waterfront, offering a member’s only bar and clubhouse.

If you’re looking for properties with bigger plots of land, Riverside should definitely be on your list. Near the waterfront, you’ll find spacious estates with wide green pastures. Riverside is also home to some of the best schools in the area.

Greenwich CT Guide: Old Greenwich

Old Greenwich was once the summer escape hub for well-to-do New Yorkers. Today, many Connecticut residents call it home. It’s also where you’ll find Tod’s Point, one of the best beachfront parks in the entire county. Locals love going to jog, cycle, fish, boat, swim or sunbathe. It’s easy to spend an entire day soaking in the ample scenic coastline.

Photo From: Jenny Allen | One of Bucky’s first beach days!

Old Greenwich offers first-class dining and shopping. Local store Back 40 Mercantile and eatery Le Fat Poodle are two of my personal favorites. Love libraries with heaps of charm and character? Stop into the Perrot Memorial Library named after Old Greenwich’s first private schoolmaster.

Northern Old Greenwich is home to quaint small neighborhoods like Hillcrest Park and Havemeyer Park. Southern Old Greenwich features private communities with luxury estates loaded with character and sophistication. From shops + restaurants to a vibrant residential community, Old Greenwich offers it ALL.

Have Greenwich CT neighborhood questions?

No matter what’s on your list of must-haves for your next dream home, having a knowledgeable Greenwich realtor makes all the difference. As a lifelong Greenwich resident, I’ll happily guide you through the area in a way only someone who has lived here her whole life can.

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