22 Evergreen Avenue

Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate where classic Arts & Crafts architecture meets the tranquility of a private countryside retreat. Set on over 2.5+ sprawling acres of pristine grounds, this exceptional 5 Bed, 5 Bath residence offers more than 5,100 sqft of refined living, surrounded by natural beauty & complete privacy. From the moment you arrive down the private, meandering drive framed by mature landscaping; The Winslow Manor evokes a sense of warmth, character, and enduring craftsmanship. Rich architectural details, beamed ceilings, inviting living spaces, & thoughtfully designed interiors create a home that feels both grand and deeply welcoming- as if stepping into a piece of cozy history, carefully preserved and elevated for modern living. Designed for both relaxation & recreation, the estate unfolds into an extraordinary outdoor experience. A sparkling Gunite pool, multiple terraces, Pergolas, & dedicated home gym create the ultimate summer retreat, while the surrounding pond and protected wetlands attract an abundance of wildlife, offering peaceful views and a connection to nature rarely found so close town. Despite its secluded setting, The Winslow Manor enjoys an unrivaled location just steps from everything that defines the Westport lifestyle. The Metro-North train, Levitt Pavilion, Compo Beach, the Westport Farmers Market, Longshore Golf Club, Cranberry Park, Sherwood Island State Park, the Westport Observatory, and Playhouse Square are all moments away, offering effortless access to culture, recreation, dining, and coastal living. Whether hosting unforgettable gatherings or enjoying quiet mornings overlooking the landscape, The Winslow Manor is more than a home - it's a sanctuary, a retreat, and a rare opportunity to own one of Westport's most captivating properties.