25 Winding Way

Rental Registration #: RP250930 Annual rental available beginning October 1, 2026. An elegant home nestled in the serene and picturesque landscape of the East End. With its strategic positioning and graceful design, it possesses an unparalleled perspective of its surroundings, allowing residents to immerse themselves in the beauty of nature. Privacy is ensured by the mature plantings lining the winding driveway, creating a tranquil retreat for residents and guests alike. The interior of the home radiates elegance and sophistication, and an array of luxurious amenities. Close to 6500' of living space on 3 levels offers 6+ bedrooms, 6.5 Luxe baths, 5 fireplaces and finished lower level. A gracious Foyer unfolds into a naturally bright open flow that consists of Living, dining and a deluxe gourmet kitchen where every detail has been meticulously crafted for comfort and convenience. Cozy up around the wood burning fireplace while enjoying the breathtaking vista. Sound system on this level as well as the pool area. Completing the main floor there is a Junior primary suite, a 15x23 custom mudroom with laundry and attached 2 car garage with EV plug. Upstairs the Primary bedroom suite features a fireplace and a private balcony with open views. Three other generous bedrooms suites, a study/media room and a convenient 2nd laundry room completes the upper level. The finished lower level unfolds to a media room with fireplace, a well- proportioned bedroom, lovely marble bath and gym/multi use room. Outdoor living is taken to new heights with the meticulously manicured rear yard, complete with a covered porch, heated 20'x40' gunite pool, sound system and an outdoor shower. Top of the line outdoor grill station promises endless opportunities for al fresco dining and entertaining. Located in sought-after Water Mill, this lovely home is just moments away from the Ocean or Vineyard, offering residents easy access to leisurely activities and premium amenities. Whether it's a day at the Beach or an evening in Southampton Village, this idyllic retreat offers the perfect balance of tranquility and convenience. [[Rental Registration # RP250930]]