Prime location, romantic 4-star hotel with charming XIX-century mansion. Complete with vineyard, olive grove, private chapel, guest cottages, annexes, swimming pool for sale in Siena. Set high on a peaceful hilltop in the rolling heart of Chianti Classico, this magnificent 19th-century villa lies just outside Castellina in Chianti, perfectly positioned between Siena and Florence. Surrounded by 46 hectares of land, the estate offers a rare combination of historic grandeur, unspoiled Tuscan beauty, and the promise of an exceptional lifestyle or boutique hospitality venture. From its elevated position, the property enjoys sweeping views over vineyards, olive groves, and forested hills. The villa has been exquisitely restored, maintaining its noble character while offering refined comforts over 1,600 square metres across four levels comprising 18 appointed bedrooms, each with views over the gardens or the vines. The interiors celebrate the elegance of traditional Tuscan design, with exposed beams, handcrafted terracotta floors, authentic fireplaces. Beyond the villa, a former stable and a barn trasformed into two welcoming guest cottages, while two further annexes provide additional space for agricultural or hospitality use. Tucked discreetly within the grounds, a private chapel adds an extra layer of charm and versatility, making the property an ideal setting for intimate weddings or private ceremonies. The swimming pool is set in a panoramic belvedere paved terrace with sweeping views of the surroundings. The land is as productive as it is picturesque starring 6 hectares planted with Chianti Classico DOCG vineyards, some dating back to the 1970s and others renewed in recent years, collectively producing up to 60,000 bottles of wine annually. Currently the vineyard is rented out. More than 600 olive trees, mature and flourishing, yield over 1000 kgs of extra virgin olive oil each year. The remaining hectares are divided between pasture, arable land, and forest, offering both agricultural viability and unspoiled natural surroundings. This is a place of rare character and provenance—ideal for a private buyer seeking a legacy estate in the heart of Tuscany, or for an investor ready to embrace the established hospitality potential of one of the region’s most captivating properties. Its beauty lies not only in its architecture or landscape, but in the way it captures the spirit of Chianti: authentic, elegant, and entirely timeless. The property is already registered as Farming and Hospitality business.