27 Woodside Avenue

Creating a private oasis at the water’s edge, this extraordinary custom residence presides over 1.10 acres in Westport’s sought-after Old Hill neighborhood. Shaded by leafy mature trees, the picturesque grounds are enhanced by vibrant gardens and sweeping, manicured lawns. Inspired by the natural surroundings, the 2006 Colonial home reflects its idyllic setting with a timeless design...

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Creating a private oasis at the water’s edge, this extraordinary custom residence presides over 1.10 acres in Westport’s sought-after Old Hill neighborhood. Shaded by leafy mature trees, the picturesque grounds are enhanced by vibrant gardens and sweeping, manicured lawns. Inspired by the natural surroundings, the 2006 Colonial home reflects its idyllic setting with a timeless design and breathtaking views across Nash’s Pond.

Introducing 9,035 square feet of refined living space, a two-story foyer gracefully extends to the back of the home to provide dazzling water views. The dramatic entry flows to a series of light-filled principal rooms enriched by classic millwork and sumptuous materials. Suited for gracious entertaining, the elegantly-appointed living and dining rooms are served by a granite butler’s pantry, which streamlines the dynamic flow between formal and dining areas. The gourmet chef’s kitchen features an exquisite modern design with marble counters, custom cabinetry, professional appliances, and a honed granite center island. Warmed by a custom fireplace, the eat-in area opens to an expansive mahogany deck accented by a bead board ceiling. As a main level focal point, the airy family room is canopied with a coffered ceiling and centers on a fireplace with natural stone surround. The family room opens to the deck along with an airy screened-in sun room to capture amazing views and emphasize the flow between indoor and outdoor spaces.  Highlighted by a tray ceiling, the library is an inviting retreat with ample built-ins and wood paneling. Two powder rooms and a custom mudroom serve the main floor.

Rising to the second level, a grand staircase is a sophisticated prelude to the master suite. Combining unparalleled craftsmanship and superb details, the master bedroom is distinguished by its soaring cathedral ceiling, fireplace, and access to a wonderful private deck. Enormous windows offer panoramic vistas of Nash’s Pond, while a spa-like marble bath and two outfitted dressing rooms add to the remarkable space. Completing the second level family quarters, four en suite bedrooms include luxurious baths and large closets, while two share a private deck. The third floor features a fabulous bedroom with a vaulted ceiling, built-ins, and serene property views. A full bath, generous bonus room, and abundant storage space complete the level.

An expansive walkout lower level boasts 1,500 square feet of additional living space. This versatile area is crowned with a coffered ceiling and opens to a gym/playroom along with a plush home theater with nine leather seats and a massive viewing screen. A resplendent full bath serves as a future cabana for the approved pool site just beyond the doors. This magnificent property is part of a private association with access to Nash’s Pond. At the edge of the emerald lawns, a personal dock allows for swimming, kayaking and paddle boarding. While sequestered in an enchanting locale, this premier estate offers convenient proximity to trains, highways, and Westport’s delightful town center. 

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