Historic Wine Estate for Sale in Gaiole in Chianti, Siena

Set in the heart of Chianti Classico, this historic wine estate in Gaiole in Chianti brings together a substantial manor house, a working winery, guest accommodation and extensive agricultural land. Dating back to the 10th century, the property combines exposed stone architecture and refined interiors with a production facility designed for serious winemaking.

The estate occupies a secluded position among the rolling hills of the Siena countryside, with vineyards, olive groves and a panoramic infinity pool overlooking the surrounding landscape. It is well suited to buyers seeking a private country residence with agricultural production, as well as those looking for a large-scale wine estate with hospitality potential.

Property Summary

• Historic wine estate in Gaiole in Chianti, Siena
• Main villa of approximately 800 square metres
• Three apartments in the main residence
• Guest cottage with one double bedroom and private bathroom
• Conserved private chapel
• 37 hectares of land in total
• 19.50 hectares of vineyard
• Organic olive groves, woodland and arable land
• Private infinity pool overlooking the vineyards and hills
• Covered garage and large private outdoor parking area

Architecture and Main Residence

The main villa is arranged over a generous interior footprint of approximately 800 square metres and retains the character of the estate’s historic origins. Exposed stonework, wooden-beamed ceilings, antique terracotta floors and large fireplaces create a traditional Tuscan setting that has been carefully maintained.

The residence is described as elegantly restored and organised for both private living and entertaining. It includes spacious reception rooms, a master suite and a large owner’s apartment on the upper floor with three bedrooms.

Accommodation in the Main Villa

• Refined interiors with wooden-beamed ceilings
• Antique terracotta flooring
• Large fireplaces
• Spacious reception and entertaining rooms
• 1 master suite
• Upper-floor owner’s apartment with 3 bedrooms

Guest Accommodation and Ancillary Buildings

Beyond the main residence, the estate includes a guest cottage, a consecrated private chapel and additional accommodation within the historic hamlet. These buildings add flexibility for extended family, staff or visitor use, depending on the owner’s intended lifestyle and operation.

• Guest cottage with one double bedroom and private bathroom
• Concecrated private chapel
• 7 rustic apartments in the hamlet
• Multi-level wine cellar and Vinsantaia
• Covered garage
• Utility rooms

Winery and Wine Production Facilities

The estate is centred around a substantial and fully equipped winemaking facility spread across multiple levels. Cellars extend to approximately 600 square metres on the estate, with an additional 70 square metres of cellars in the village and a 90 square metre Vinsantaia on the upper floor.

The production spaces are fitted with stainless steel tanks and wooden barrels for ageing, supporting the estate’s established wine programme and bottle production capacity.

• Approximately 600 sq m of cellars on the estate
• 70 sq m of cellars in the village
• 90 sq m Vinsantaia on the upper floor
• Stainless steel tanks with capacity for 1,800 HL / 180,000 litres
• Wooden barrels for ageing with capacity for 470 HL / 47,000 litres
• Annual production potential of up to 90,000 bottles
• International export network already established

Land, Vineyards and Olive Groves

The estate extends over 37 hectares of privately owned land managed under certified organic farming practices. The mix of vineyard, olive grove, woodland and arable land creates a classic Chianti agricultural setting with meaningful scale and visual variety.

• 37 hectares / 91.4 acres of land
• 19.50 hectares of vineyard area
• Approximately 3–7 hectares of organic olive groves
• Woodland and arable land
• 1,000 olive trees of the Coreggiolo and Moraiolo varieties
• Certified organic farming practices

Outdoor Living and Grounds

The outdoor spaces are arranged to complement the historic architecture and the surrounding landscape. A paved courtyard and manicured gardens frame the property, while the infinity pool is positioned to take in open views across the vineyards and the Sienese hills.

• Paved courtyard
• Manicured gardens
• Private infinity pool measuring 4 x 11 metres
• Pool depth of 1.60 metres
• Views over the vineyards and surrounding hills
• Covered garage
• Large private outdoor parking area

Gaiole in Chianti and the Siena Countryside

Located in Gaiole in Chianti, within the Province of Siena and the broader Tuscany region, the estate sits in one of Italy’s most recognised wine areas. Its secluded setting offers privacy while remaining within reach of Tuscany’s celebrated towns, making it suitable for both residential and production-focused use.

Who This Estate May Suit

This property is likely to appeal to buyers seeking a historic country estate with established wine production, substantial guest accommodation and a strong sense of place. It may also suit those looking for a prestigious private residence, a working winery or a hospitality-led country estate in Chianti Classico.

Enquire About This Wine Estate in Gaiole in Chianti

For further information, pricing details or to arrange a private viewing, please contact Worldwide Dream Properties. Our team will be pleased to assist with your enquiry.

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