1245 High School Road NE

Sited at the head of the 8th fairway of Wing Point Golf & Country Club, this rare, south-facing home has long been considered one of the most prominent and stately properties on the course. Perfectly manicured grounds frame serene views of flowering gardens, tranquil ponds, and majestic evergreens — creating a picturesque setting for this elegant yet comfortable retreat. With over 3,200 sq ft of finished living area, the thoughtfully designed floor plan provides generous room for both relaxed everyday living and sophisticated entertaining. A gracious two-story entry hall leads to a private Library / Home Office, and in turn to the refined living and dining spaces, which feature soaring ceilings and a marble fireplace. At the heart of the home, is an impressive chef’s kitchen with an adjoining casual dining area that flows seamlessly to expansive decks and patios; perfectly positioned to capture both all day sun and evening twilight. The open and inviting family room, with its exposed wood beams and brick fireplace, ensures warm and memorable evenings. Upstairs, there are three spacious bedrooms, including a magnificent primary suite with vaulted ceilings, a luxurious sitting area, an extraordinary walk-in closet, and a charming private deck overlooking the gardens and fairway below. Additional highlights include a heated 3-car garage with workshop space, 10-foot ceilings (providing ample room for a golf simulator) and an additional 1,400 sq ft of semi-finished attic space, including 800 sq ft currently in use as a bonus family room. Enjoy the best of Island living in this exceptional property where privacy, comfortable living spaces and captivating views come together in perfect harmony — just minutes from the ferry, Winslow’s shops, restaurants and top-rated schools.