A truly rare offering on the shores of Winter Harbor, this remarkable 40± acre property presents a once-in-a-generation opportunity to own one of the most extraordinary waterfront estates in Wolfeboro. Comprised of two distinct 20-acre parcels, the property captures the very essence of lakeside New England living. On the lake side of North Main Street, an antique seasonal cottage overlooks the sparkling waters of Lake Winnipesaukee, where breathtaking sunsets paint the sky above Winter Harbor each evening. Sandy waterfront, sweeping views, and the tranquil setting create an idyllic retreat to enjoy today while envisioning what tomorrow may bring. Across the road, rolling fields and open meadows surround an antique Cape, forming a timeless pastoral landscape rich with character and possibility. The existing home offers an opportunity for restoration or redevelopment, while the gently sloping terrain provides exceptional flexibility for future plans, including the potential for walkout lower levels designed to maximize both views and indoor-outdoor living. Whether your vision is a private family compound, an equestrian estate, a multigenerational retreat, or a thoughtfully designed development opportunity, the rare combination of substantial acreage, waterfront, open fields, and lake views offers possibilities that are nearly impossible to replicate in today's market. This is a property meant to be cherished, shaped by its next steward, and enjoyed for generations to come. Adding to its appeal is the location itself. Welcome to Wolfeboro, often regarded as one of New England's most charming villages. Here, you'll find the perfect balance of peace and privacy while remaining just minutes from the vibrant downtown, with its boutique shops, restaurants, marinas, and year-round community events.