In a corner of Westport that still feels quietly untouched, properties like this rarely come to market. Tucked along a private lane in the Greens Farms neighborhood, 4 Sherwood Island Lane unfolds across more than 20 acres of protected waterfront land, where open sky, tidal marsh, and long views over Sherwood Island State Park define the experience as much as the home itself.
Offered for $15,000,000 and represented by Andrew Whiteley and Wendy Ryan of Brown Harris Stevens, the property has been held by the same family for more than 65 years, a tenure that speaks to both its rarity and its enduring appeal.
What distinguishes this offering is not simply scale, but setting. Surrounded by protected land with no immediate neighbors, the estate carries a sense of remove that feels closer to coastal enclaves like Nantucket or the Lowcountry than to suburban Connecticut. At the same time, it remains within easy reach of town, train, and Manhattan, balancing seclusion with accessibility.
The existing residence, a 1940 Colonial spanning over 6,000 square feet, anchors the property with seven bedrooms and a series of living spaces oriented toward the water. Across the grounds, a collection of additional structures, including two three-bedroom guesthouses, creates a compound-like arrangement that allows for both gathering and independence.
Outdoors, the estate leans fully into its landscape. Expansive lawns roll toward the shoreline, punctuated by formal gardens, a tennis court, and a pool with its own dedicated house. An indoor pool adds a year-round dimension, while the surrounding environment brings a constant sense of movement through light, weather, and wildlife.
There is also a notable flexibility to the offering. The property can be enjoyed as it stands, preserved as a legacy holding, or reimagined over time. Its scale and positioning open the door to a range of possibilities, from a private retreat to a multigenerational compound shaped for the future.
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