144 Cherry & Webb Ln (Westport, MA)

Welcome to “Second Wind” — your serene coastal retreat on Westport Point!
Set on over four private oceanfront acres with 150 feet of sandy beachfront along the Atlantic, this stunning 4-bedroom home offers one of the most beautiful natural settings you’ll ever experience. Nestled in the dunes, it combines privacy, comfort, and panoramic views of Buzzards Bay for the perfect seaside escape.

Designed for relaxation and entertaining, this spacious three-story residence features cathedral ceilings, an artist’s loft, a double-sided fireplace, and a dumbwaiter serving all levels. Enjoy mornings walking your private beach and evenings taking in the sound of the waves. Outdoor amenities include a shower and architect-designed expansion plans for a garage and elevator available upon request.

Located within a short walk or cart ride to Tripps Marina and The Back Eddy Restaurant, you can park your car for the weekend and truly unwind. Whether you’re seeking a seasonal getaway, a year-round oasis, or investment potential through Airbnb, Second Wind offers the ultimate luxury coastal lifestyle—reminiscent of the outer Cape, but without the bridges, traffic, or crowds.