5 Waterfront and Prewar Luxury Homes Across New York and Connecticut

Along the water’s edge on Judy Point Lane in Westport, this gated estate unfolds across more than three private acres with sweeping water views and a rare compound-style layout. Two complete residences are connected by a breezeway, offering natural flexibility for multi-generational living, extended guests, or a dedicated guest house. Inside, soaring ceilings and expansive windows bring the landscape into focus, while multiple stone fireplaces anchor the dramatic interiors. Generous living and entertaining areas transition seamlessly to outdoor terraces and landscaped grounds designed for both relaxation and gathering. A waterside pool overlooks the water, and a private dock adds effortless access for boating. Mature plantings and a gated driveway heighten the sense of seclusion, with the added potential for an indoor pool and spa to further shape a resort-like routine.

Along the Hudson River on Riverside Drive, Apartment 11C offers a rare convergence of Gilded Age splendor and 21st-century sophistication. Originally completed in 1910 and credited to architect Ralph Townsend, this prewar condominium has been reimagined through a comprehensive, studs-out renovation that threads state-of-the-art infrastructure into a pristine historical envelope. A classic floorplate is anchored by a graceful central gallery, opening to a sensational trio of entertaining rooms overlooking the river—an effortless setting for evenings in and hosting alike. Restored fin de siècle craftsmanship runs throughout, from intricate white oak marquetry floors to newly installed double-glazed windows and doors framed in exquisite period millwork. The result is a residence that feels at once deeply rooted and quietly current, with the river as a daily backdrop.

Set on just shy of three acres on a quiet cul-de-sac in East Hampton, this expansive estate is designed for hosting with ease and privacy, backing to reserve land and located about two miles from East Hampton Village. Inside, the first floor moves from an inviting entryway to a chef’s kitchen with a casual seating area, alongside a dramatic double-height living room and a private dining room. A main-level primary suite adds flexibility for everyday living. Upstairs, three ensuite guest bedrooms complement a large primary suite with a fireplace, plus a billiards area that comfortably doubles as an office. The finished lower level deepens the amenities with a custom theater, gym space, guest bedroom and full bath, an office, and a 3,000-bottle wine cellar. Outdoors, a screened-in porch overlooks a backyard with an extensive patio, heated pool, and spa—ready-made for long, lingering weekends.

Along the water’s edge on Reynolds Channel, this brand-new, never-lived-in four-level estate pairs 60 feet of premium waterfront with a new bulkhead and a private dock. Inside, expansive living spaces are oriented to unobstructed water views, with an elevator connecting all levels for effortless daily flow. A chef’s kitchen anchors the home, complemented by five bedrooms and 4.5 designer baths that underscore the property’s polished, contemporary feel. Outdoors, resort-style amenities set the tone for weekends at home: a hot tub, built-in BBQs, and a heated rooftop deck where NYC views stretch beyond the shoreline. Practical comforts are equally considered, with a three-car garage and ample parking. Set in Point Lookout, the home also includes exclusive beach and playground rights—an easy invitation to linger longer by the water.

Along the water’s edge on Shelter Island, this custom-built residence is set on 1.1 private acres at the end of a long driveway, balancing luxury with genuine seclusion. Inside, radiant heat, a Sonos sound system, and a dramatic two-story great room with an indoor/outdoor stone fireplace set an easy, elevated tone. The first-floor primary suite opens to a private deck and includes a walk-in closet and a spa-inspired bath with rain shower. In the chef’s kitchen, custom cabinetry and granite counters are paired with walls of glass that open to a wraparound mahogany deck overlooking lush grounds, a gunite pool, and a slate patio. A full finished basement with egress adds flexible living space. A barn-style four-car garage offers lift potential, topped by a one-bedroom apartment with full kitchen and open living area—ideal for extended stays. Nearby, Shelter Island Heights, ferry access, golf, tennis, hiking, and bay beaches shape the everyday rhythm.