In the rolling hills of Tuscany’s Chianti Classico region, a few kilometres from Castellina in Chianti, lies a wine estate unlike any other. Dating back to the 11th century, this historic hamlet has evolved over the past millennium into a thriving organic vineyard estate that combines timeless architecture with a forward-looking approach to agriculture and sustainability.
Today, it spans 335 acres (135.6 hectares) of certified organic vineyards, olive groves, forest, and refined residences. It produces approximately 75,000 bottles of wine each year – 75% of which are exported – and presents a rare opportunity to invest in one of Italy’s most sought-after sectors: high-end, eco-conscious winemaking.
Apolloni & Blom is the agency representing this exceptional property. Known for their experience in Italy’s most desirable regions, they specialize in connecting international buyers with rare, high-value real estate assets.
A Tuscan Estate Rooted in History But Built for the Future
This property is more than just a vineyard. It’s a living piece of Tuscan heritage, where medieval stone buildings meet the demands of today’s discerning wine investor.
A Historic Hamlet with an Organic Mission
At the heart of the estate is a restored 11th-century stone borgo, which was originally a small agricultural hamlet. It has been carefully preserved and thoughtfully updated, and the buildings include several guest residences featuring hallmark Tuscan design such as terracotta floors, exposed beam ceilings, loggias, and arched stone interiors.
The land itself tells its own story. Out of 335 acres, 82 (33 hectares) are dedicated to vineyards. The estate is planted primarily with Sangiovese, the noble grape of Chianti, alongside Merlot, Petit Verdot, Cabernet Sauvignon, Sauvignon Blanc, and Chardonnay. Since 2009, the entire operation has been certified organic.
With a focus on quality over quantity, the estate produces 75,000 bottles per year. A full 75% of production is exported to international markets, making this not just a beautiful place to live, but a functioning business with an established global presence.
There’s also an award-winning olive oil operation. Using the traditional local varieties of Moraiolo, Leccino, and Correggiolo the estate presses DOP-certified organic extra virgin olive oil, adding another layer to its agricultural output.
The winemaking infrastructure is equally impressive. The main winery spans over 22,000 square feet (2,077 sqm), combining modern enological equipment with classic Tuscan architecture. An additional 13,218-square-foot (1,228 sqm) country hamlet, along with a 16,113.5-square-foot (1,497 sqm) structure, features tasting rooms, holiday homes, and administrative offices.
Where Lifestyle and Legacy Meet
Chianti Classico is experiencing a shift. It’s not just about producing good wine but creating something enduring, and according to the Consorzio Vino Chianti Classico, high-end labels like Riserva and Gran Selezione now represent nearly half of all production value, reflecting a clear move toward quality.
This estate embodies that shift. Its organic credentials, international reputation, and architectural elegance make it a standout option for anyone looking to establish a luxury wine brand or invest in a fully operational, prestige-driven business. The nearby success stories of Il Palagio (owned by Sting), Alessandro Gabbani (partner to Giorgio Armani), and the Coppola family speak volumes: Chianti Classico is increasingly the domain of visionaries who see wine as both an art form and an investment.
Whether your goal is to create a boutique label, open a luxury agriturismo, or simply enjoy a private estate with meaningful returns, this property delivers on flexibility, authenticity, and long-term value.
Tuscan Simplicity, Global Sophistication
The setting alone makes this estate exceptional, but its accessibility and infrastructure complete the picture.
A Privileged Location in Castellina in Chianti
The property is just outside Castellina in Chianti, one of the historic towns in the Chianti Classico region. From here, Siena is only 25 kilometres to the south and Florence 45 kilometres to the north. The A1 Autostrada is 20 kilometres away, offering direct road access to Milan, Rome, and beyond.
Florence Airport (Amerigo Vespucci) is 55 kilometres away, and Pisa International Airport can be reached in about 110 kilometres. This central yet secluded location offers the best of both worlds: tranquil countryside living within easy reach of major cities, transport hubs, and cultural landmarks.
But despite its connections to major cities and urban centers, the surrounding landscape of rolling vineyards, olive groves, and forested hills is as quintessentially Tuscan as it gets. For those seeking both seclusion and prestige, this part of Italy remains unmatched.
A Region in High Demand
Recent market reports show that Tuscany continues to lead Italy in luxury real estate sales, with Chianti Classico at the forefront. According to Idealista, international demand for high-end properties has been particularly strong, with lifestyle investors seeking homes that offer natural beauty, historic charm, and income-generating potential.
Certified organic vineyards with architectural significance are especially rare. The combination of agricultural output, tourism potential, and historic real estate places this estate in a category of its own.
The growing interest from prominent figures in music, fashion, and film only adds to the region’s global appeal. Investors are no longer just buying property, they’re buying into a lifestyle, a legacy, and a brand.
A Rare Asset with a Timeless Story
This estate is a compelling balance between tradition and opportunity. With over 1,000 years of history, a successful wine and olive oil business, and a restored architectural offering that honours its past, it has something that’s increasingly hard to find: authenticity with scale.
Whether considered as a private residence, an investment, or the foundation for a wine brand with international potential, it stands as a lasting symbol of what Tuscany does best: combining beauty, culture, and craftsmanship. To learn more about this exceptional opportunity at the heart of Chianti Classico, contact Apolloni & Blom
