5 Luxury Coastal Retreats from the Hamptons to Westport

Set on 3.79 acres of beautifully wooded land, 6 Clara Drive is a modern Hamptons retreat completed in 2023, quietly positioned at the end of a cul-de-sac in the coveted Southampton Pines development of East Quogue. The new construction is designed for comfort, functionality, and timeless appeal, offering five spacious bedrooms and 4.5 bathrooms within a layout that balances everyday ease with a considered sense of retreat. Arriving feels distinctly private: the home is tucked away and bordered by lush trees, creating a natural buffer that heightens the calm of the setting. Here, modern craftsmanship meets serene surroundings, with space to gather, unwind, and settle into the slower rhythm that wooded acreage in the Hamptons invites.

Steps from the shoreline on the coveted ocean block of Point Lookout, this turn-key residence pairs exceptional craftsmanship with new balconies and striking views. Parking is thoughtfully handled with a two-car driveway plus a one-car garage space with extra storage—an easy rhythm for beach days and weekends out. Inside, hardwood floors run throughout, setting a clean, continuous backdrop for everyday living. The living room feels especially airy and welcoming, thanks to high ceilings and an open, bright layout that lets the space breathe. Anchoring it all is a gas fireplace, bringing warmth and quiet atmosphere when the day winds down. From morning light to evening breezes off the balconies, the home is designed for a coastal routine that feels effortless.

Steps from the shoreline in Point Lookout, this brick Cape pairs classic character with thoughtful updates designed for easy coastal living. New windows and a brand-new roof bring a fresh sense of efficiency, while an upgraded heating system supports year-round comfort. Inside, wood floors and a fireplace set a warm, grounded tone, complemented by a modern kitchen that suits both everyday routines and relaxed gatherings.

Along the water’s edge in Westport’s coveted Old Hill, this timeless home pairs generous living space with a calm, landscaped rhythm. A gracious foyer opens to a living room with hardwood floors and a fireplace, while the eat-in kitchen—finished with marble countertops, double ovens, and abundant cabinetry—connects easily to both formal and casual dining areas and a sunlit great room. Everyday flow is considered, with a mudroom and laundry just off the garage. Upstairs, four bedrooms include a primary suite with a full bath, ample closets, and a bright porch that reads as a natural office or quiet retreat. The finished lower level adds an office/guest room and full bath. Outside, a private backyard offers a gunite pool and spa, complemented by a front pond with fountain.

Originally built in 1910, this rarely available penthouse duplex unfolds in a classic prewar walk-up co-op on a prime West Village street, with the added allure of roof rights. The sun-drenched lower level is organized for easy entertaining, anchored by a gracious south-facing living room and a charming wood-burning fireplace, with an elegant dining area and a thoughtfully designed kitchen close at hand. Upstairs, two south-facing bedrooms create a calm retreat: a serene primary bathed in natural light, and a second bedroom brightened by a skylight. Rich hardwood floors run throughout, while ceilings ranging from 9’5″ to 10’2″ lend an airy sense of volume. Set within the Greenwich Village Historic District, it offers a daily rhythm shaped by tree-lined streets, landmarked townhouses, and downtown dining and culture.

Size: – sf