Greenwich offers a diversity of options, but modest homes under $1 million are in short supply. Near downtown Greenwich, you’ll find homes on smaller lots, providing quick access to the shopping, dining and retail of Greenwich Avenue and the train station. Closer to the shores sits Belle Haven, a gated waterfront community with its own yacht club and access to the beach and tennis club. Price points in this exclusive area are typically the highest in all of Greenwich.

As you travel further out to mid-country which is bounded by the Merritt Parkway to the north and Post Road to the South, you’ll find larger lots (typically 1-2 acres). Neighbors are close enough to develop a friendly community atmosphere, but properties are spread out enough to feel like a personal country retreat. Close enough yet away from it all, the average drive to the Greenwich train station to Manhattan is ten minutes.

Situated north of the Merritt Parkway and bounded by Westchester County and North Stamford, back-country offers larger lots (typically 4-acre zoning). Here you’ll find tree-lined streets, stately residences on rolling hills and historic estates on equestrian farms. There is also an abundance of nature trails, golf courses, horseback riding trails and plenty of outdoor spaces which have been preserved through the Greenwich Land Trust. Backcountry offers tranquility and privacy, but no shopping or dining options.

Cos Cob provides relatively affordable prices compared to the other neighborhoods within Greenwich, making it a perfect option for those seeking to enjoy the sought-after amenities without the ultra-luxury price tag. Near the town’s commercial center, you can find more modest homes on smaller lots. As you travel north, newer contemporaries and colonials with pools and tennis courts fill two-acre parcels. There are certainly many majestic homes with high price points throughout the town, but you’ll find fewer of the opulent estates in Cos Cob than some of the neighboring hamlets of Greenwich.

Riverside offers a diversity of options in style and price. During the 1930s and 1940s, when houses began cropping up on large leafy lots, this neighborhood had some of the highest real estate values in the area. Today, the waterfront community is still wealthy, but buyers can find an impressive variety of options, both in housing styles and price points, making it a sought-after New York City suburb for house-hunters seeking a serene outpost. 

Prices in Old Greenwich reflect proximity to the water and access to the Village. While homes are typically closer together, this contributes to the tight-knit community feel. The majority of homes are single-family, though there are a handful of condo complexes on or near Post Road. In the northern part of town above Post Road, you can find Cape Cods and Colonials for under $1 million, but most of these homes will be less than 2,000 square feet and sit on less than a half acre. Newly constructed houses and those on the waterfront (below Route 1) sell for considerably higher, and houses directly on the Long Island Sound can sell for over $10 million.