On the Market: Six Waterfront Properties in the Hamptons
by Grace Cassidy
June 2025
40 & 42 Deforest Road, Montauk | $39,995,000
This newly built Montauk retreat is sited on two waterfront acres, made up of two separate lots. The Ditch Plains area property has two homes with a combined 9,942 square feet, 14 bedrooms, 12 full bathrooms, two half-bathrooms, two pools, and two spas. Additional features include covered outdoor living spaces, hardwood floors, walls of windows, modern kitchens, and multiple fireplaces.
34 Westbridge Road, Westhampton Beach | $24,750,000
Spanning over 14,000 square feet in size, this newly built oceanfront estate in Westhampton Beach comprises eight bedrooms and 10 bathrooms. Features include top-of-the-line kitchen appliances, a luxurious second-floor primary suite with water views and a private covered deck, and a private guest suite with a separate entrance and kitchenette. The outdoor living space features a heated saltwater pool, spacious decks, a fire pit, custom outdoor kitchen, and cabana bathroom.
2056 Montauk Highway, Amagansett | $22,500,000
Sited on 2.4 private oceanfront acres in beautiful Amagansett, this 8,200-square-foot home offers six bedrooms, seven full bathrooms, and two half-baths. The great room is a perfect place to relax with loved ones around the fireplace, grab a drink from the wet bar, and watch the ocean from the generous glass doors. The primary suite is a restful space, complete with a sitting room, spa-like bathroom with a soaking tub, dual walk-in closets, and access to two private outdoor decks. A formal dining room, gym, and bonus room are also included.
199 Dune Road, Westhampton Beach | $14,250,000
This 1988 modern home (below, at left) has been totally renovated to bring the interiors up to date and offers 360-degree views of both the ocean and the bay. The 5,000-square-foot home features six bedrooms, seven and a half bathrooms, walls of windows, a stone fireplace in the living room, beautiful wood paneling, cathedral ceilings, and indoor-outdoor living with direct beach access. A fireplace, sitting area, walk-in closet, and spa-like bathroom come together to create a restful primary suite on the second floor. Outdoor space includes a heated gunite pool, outdoor kitchen, and cabana complete with a bathroom.
101 Jessup Lane, Westhampton Beach | $7,950,000
Residents of this Westhampton Beach shingle-style home (below, at right) will appreciate its waterfront location, private dock, and panoramic water views. The 8,040-square-foot retreat includes seven bedrooms, eight and a half bathrooms, seven fireplaces, expansive living spaces, hardwood floors, walls of windows, and a well-equipped chef’s kitchen with a spacious center island, top-of-the-line stainless steel appliances, a wine refrigerator, and warm brick details. Meanwhile, the outdoor living space features a heated pool, beautiful landscaping, covered living areas, and a short walk to ocean beaches on nearby Dune Road.
27 Dune Road, East Quogue | $5,495,000
This oceanfront Dune Road property in East Quogue (below, at bottom) comprises two beach cottages, making this a great option for intergenerational living or for households who frequently host guests and loved ones. The homes have both recently been renovated and brought up to date, complete with custom kitchens, hardwood flooring, wide windows and sliding glass doors, built-in bookcases, and outdoor living areas. Residents will love the fact that the property is situated next to town-owned land (for extra privacy) and that the beach is just a short walk away.
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