Living in Old Greenwich: A Lifestyle and Real Estate Guide to Old Greenwich, New York

Old Greenwich—A Treasured Locale on Connecticut’s Gold Coast

What and Where Is Old Greenwich, Connecticut

Old Greenwich, along with the neighborhoods of Byram, Cos Cob, Glenville, Mianus, and Riverside, is part of the Town of Greenwich in Fairfield County, Connecticut. Old Greenwich offers residents all the benefits of coastal living on the doorstep of New York City, just an hour away by car or train. The town extends from the southeastern edge of Greenwich town to Long Island Sound. The heart of Old Greenwich is the historic downtown, Sound Avenue, with its post office, listed railroad station, and locally owned shops and restaurants. But the real draw is its long stretch of Long Island Sound coastline with views of the New York City skyline.

Old Greenwich and the surrounding neighborhoods cater to the luxury lifestyle: there are beaches, parks, yacht clubs, tennis, golf, and country clubs. The town of Greenwich is a shopping mecca with McClaren, Bentley, and Rolls-Royce car dealerships and high-end retail stores, such as Saks Fifth Avenue, Hermès, and Apple.

Historical Old Greenwich

The original Town of Greenwich was originally known as Monekewaygo, marshland between the Asamuck and Potommuck brooks occupied by the Wecquaesgeek, a tribe of the Wappani Wappan First Peoples, for centuries. On July 18, 1640, they traded the land to the New Haven Colony. The signers were militia commander Captain Daniel Patrick, wealthy property owner Robert Feake, and Feake’s wife, Elizabeth Winthrop Feake. The niece of Massachusetts Bay Colony Governor John Winthrop, Elizabeth was immortalized in Anya Seton's 1958 novel The Winthrop Woman.

In the 17th and 18th centuries, the area was named “Horseneck” after a tract of pastureland used by the settlers to graze their horses. It was a stop along the main route from New York to Boston, "the Country Road,” a precipitous rocky road until it was improved in the early 19th century, and later became US Route 1. In 1848, the train first arrived and the name chosen for the only station was “Greenwich” later became Greenwich Old Town.

In 1872, the community’s name changed again, this time to “Sound Beach,” to attract affluent holidaymakers from New York and Boston. In the 1920s, Greenwich was the richest town per capita in the world. The Rockefellers, Lauders, and other titans of industry built rambling estates in Greenwich’s rolling countryside and along the Sound.

In 1931, the name reverted to Old Greenwich.

Sophisticated Coastal Living

Old Greenwich is the grande dame of the Town of Greenwich. Consistently ranked as one of the wealthiest in the United States by Bloomberg, the Town of Greenwich is known as the "hedge fund capital.” A third of its office space is occupied by the trillion-dollar hedge business and several residents are on Forbes’ 2021 World's Billionaires List.

Many of the private gated communities along Long Island Sound, such as the Indian Harbor Association, and Belle Haven, and rural enclaves of the Town of Greenwich, such as Round Hill and Conyers Farm, are home to famous names from show business. Henry Fonda and George C. Scott were residents in their day, as was Truman Capote, who attended Greenwich High School from 1939 to 1942.

The residents of Old Greenwich are what the locals call “quieter money.”

Real Estate in Old Greenwich

Old Greenwich lies along Connecticut’s Gold Coast, bounded by Long Island Sound on three sides. Residents refer to the Old Greenwich’s downtown as “the village” and other parts of town as either “south of the village” or “north of the Post Road.” Surprisingly, it has one of the lowest property tax rates in the New York metro area. The majority of homes are large single-family houses. The grandest are the Colonial-style waterfront properties along Long Island Sound. Many of the town’s private neighborhood associations maintain their own beach areas.

World-Class Recreation

Old Greenwich has a wealth of family-friendly recreation. Greenwich Point Park offers 147 acres of parkland, miles of walking trails, and two beaches on Long Island Sound. Open year round, the park is home to the Bruce Museum Seaside Center, which is dedicated to the wildlife of Long Island Sound. Two concession stands and boat and kayak rentals are open in the summer months. The 32-acre picture-postcard Binney Park has a gazebo, tennis courts, baseball diamonds, and a soccer pitch.

Old Greenwich also has its fair share of private clubs. The exclusive Innis Arden Golf Club was founded in 1899. Its 18-hole course, redesigned by Ken Dye, has hosted many qualifying events as well as several championships. Facilities include a clubhouse, tennis courts, swimming pool, and fitness center. The Old Greenwich Tennis Academy has five indoor championship Har-Tru tennis courts. The Old Greenwich Yacht Club was established in 1943. The Rocky Point Club is an independent, non-profit organization offering sailing, swimming, and other nautical activities.

Retail Therapy

Old Greenwich offers a slice of old town Americana. There’s a farmer’s market every Wednesday, clambakes and parades in the summer months, and a Fourth of July annual fireworks display. For a taste of 21st-century creature comforts, the Town of Greenwich has everything for the luxury consumer. The main thoroughfare, Greenwich Avenue, is one of the premier shopping streets in the United States and dubbed the "Rodeo Drive of the East.” Home to high-end retailers such as Apple, Hermès, Tiffany & Co., and Saks Fifth Avenue. Over on Putnam Avenue, there’s a slew of luxury car dealerships, from Rolls-Royce and Bentley to Bugatti and McLaren.

Dining in Old Greenwich

Beach House Café seafood restaurant; Le Fat Poodle French bistro; Applausi Osteria Toscana, and Lugano Wine Bar & Salumeria are elegant dining options in Old Greenwich. The town of Greenwich has several award-winning restaurants. For waterfront dining, L’escale, at Delamar Greenwich Harbor Hotel in the town of Greenwich, is a romantic spot with a Provençal menu created by Chef Frederic Kieffer.

Top-Rated Schools in Old Greenwich

The Greenwich Public Schools consist of eleven elementary schools, three middle schools, and one high school with an alternative high school program.

Old Greenwich School is a top-rated public school with 422 students in grades pre-kindergarten through five. Western Middle School and four elementary schools (Hamilton Avenue School, Julian Curtiss School, New Lebanon School, and International School at Dundee) are magnet schools. The International School at Dundee was named as a School of Distinction by the state education department for Highest Overall Performance. Other highly rated public schools include Chabad Hebrew School (kindergarten through grade seven) and Greenwich Japanese School (elementary and junior high).

There are a number of elite private schools in the environs. Among them are Greenwich Country Day School (nursery school through high school); Brunswick School, a college prep school for boys (pre-kindergarten through 12th grade); and Greenwich Academy, a college prep school for girls (pre-kindergarten through 12th grade).