365 Greens Farms Road, WestPORT
$3,800,000 • 6 Bedrooms • 4 | 1 Baths
2% to Buyers Agent
Private Exclusive
Generously sited on 2.15 stunning acres in Greens Farms, the Joseph H. Wakeman House is a perfect example of New England ingenuity and warmth. Built in 1840, this distinguished Federal-style residence was thoughtfully reimagined in the 1930s by an owner intent on showcasing its craftsmanship and enduring quality.
The current residents were similarly captivated by its character and history. Located in the heart of one of Westport’s most coveted and convenient neighborhoods, the park-like grounds, with sweeping lawns and meandering stone walls, are enchanting in every season.
Inside, the home is warm and inviting—walls painted in pristine white provide a clean backdrop that highlights architectural details and period millwork. Wideboard floors and 9-foot ceilings extend throughout, underscoring the timeless proportions and charm. Welcomed through double front doors, guests are immediately drawn to the gracious front hall or library, lined with bookshelves and anchored by the home’s original staircase—a space so inviting, it is hard to leave. The elegant living room, with its rare double fireplaces, easily accommodates a grand piano, while the intimate formal dining room—also with a fireplace, encourages evenings when friends linger. A butler’s pantry connects seamlessly to the gourmet kitchen, which opens to the terrace and is bathed in natural light. The spacious family room features wide French doors to the yard, while a charming mudroom offers a practical yet welcoming entry.
Throughout the home, greenery and garden views blur the line between inside and out.
Upstairs, the second floor is anchored by a tranquil primary suite with an exquisite new bathroom.
Four additional bedrooms provide comfort and flexibility for family or guests. The third floor offers its own sense of retreat, with a bunkroom, full bathroom, and a cheerful playroom.
Outbuildings include a separate garage with custom-made doors, a barn, corn crib and garden shed.
Southport Harbor and beach are both within walking distance. This is a timeless, magical home - come walk through it and feel some of our town’s early history.
