Generational opportunity...the chance of a lifetime now awaits in one of Winnetka's most premier "off lake" enclave neighborhood...936 Sunset Road with two golden options for this exclusive real estate offering. This extraordinary Ralph Lauren vibe, country ranch is all about casual elegance with a desirable first floor primary suite. Set on a magnificent 1.29 acre lot, this property now INCLUDES a Village approved subdivided .67 acre buildable lot option so you can sell off OR use & expand your dream estate with a second structure with separate service entrance. Inviting presence with circular drive & framed manicured grounds presents a very storybook residence with classic architecture, new composite cedar shake roof, copper gutters, and charming dormers creating unforgettable curb appeal. A welcoming covered front porch sets the tone as you enter the foyer thru the Farrow & Ball French blue doors, brick flooring and Nantucket inspired millwork. This expansive ranch with southern exposure naturally lights up the entire house as the formal living with picturesque windows showcases the breathtaking views of the expansive grounds & tennis court. Just beyond, the spectacular sunroom/family room serves as the heart of the home with panoramic views of the lush backyard and entertaining terraces, creating an effortless indoor-outdoor connection. The dining room offers an intimate yet refined setting for gatherings and leads to the updated classic all white kitchen accented with Carrera marble and designed by notable North Shore architect Chip Hackely. Custom cabinetry accented with huge breakfast bar island with seating for 6 and expansive prep space make this the hub of the house with great views of Sunset Road. An adjoining breakfast area surrounded by French doors overlooks the picturesque property and opens directly to the outdoors. Additional first floor living spaces include an inviting den with vaulted ceilings, custom built-ins, and stone fireplace, offering the perfect retreat for relaxing, entertaining or expansive option to make primary suite larger. Completing the main level is the luxurious first-floor primary suite, a peaceful sanctuary with rolling green views and spa stone bath. The spacious second floor continues with five family sized beds and three updated all white marble baths, including two private ensuite retreats and an additional hall bath. Each bedroom is flooded with light and can also be a perfect place to expand the house if needed. One of the bedrooms is currently being utilized as a sophisticated office space. The lower level offers an exceptional additional living space centered around a large recreation room, kitchenette, laundry center. Enchanting outdoor space with blue stone patios, tennis court and miniature replica playhouse make this property so special as there in incredible opportunity with second lot to elevate to another level of luxury by adding a 20x40 pool with separate tricked out cabana house with wellness gym, golf simulator room, 2nd office and guest quarters. If you rather just live in the house and sell off the back land, that is a fabulous option as well or even live as the house is now and plan for the future, it all works here. This opportunity is one of kind as there are many different ways to optimize 936 Sunset all while being in an A++ location, south of Willow, steps to Crow Island, FCH, and NSCD schools and either way to New Trier or Loyola, plus, don't forget, town and the train are right there too. This is your optimal long term forever house option as there many customized opportunities to make this your own. Either right away or over time, the most important this is that you have SECURED a prime address on the street that falls right behind living on the lake. The ultimate North Shore investment property to be offered in years!