Historic Italian Properties with Vineyards


It’s no secret that Italy is home to magnificent architecture, rich history and picturesque settings. Are you looking for a truly unique property that not only takes your breath away but also has a story to tell? Dating back as far as the 10th century, we offer a range of historical properties including former convents, estates, villas, hamlets, and castles with vineyards and features from the past. These properties are in a variety of areas in Tuscany with vineyards that produce different wines such as Cabernet, Merlot, Sangiovese, Chianti Classico and more. See below for just a selection of some of our best historic properties complete with vineyards.

V3487AB    |    Castelnuovo Berardenga, Tuscany    |    €2,900,000

This stunning estate is located in the countryside just 21km from Siena. It comprises a beautifully restored villa with a 13th century watch tower, once home to the guards of the Cerreto Castle. There is also a guest annex of 140 sqm as well as 27 hectares of land consisting of 150 olive trees, vineyards (4.5 hectares) and woods. The estate produces its own wine from Cabernet, Merlot and Sangiovese grapes. There is also a large swimming pool. Renovated in 1998, The main house has a watch tower to which two lateral structures were added over time. This particular layout, with the annex separate from the main villa, makes the property ideal for large groups who can have their own privacy when needed.

V5258PV     |      Greve in Chianti, Tuscany       |     €6,800,000

Located in the beautiful region of Chianti with easy access to Florence, this well established working winery is made up of approximately 100 hectares of land. 17 hectares of this land is covered by DOCG vineyards, plus 3 hectares of IGT Toscana and another 20 hectares of cultivated olive groves. The borgo comprises a main villa, constructed in the early 1800s, several other buildings that support the business (wine, oil production, rental apartments) and two swimming pools.  The remaining land consists of a forest, woodlands, and land that may be cultivated in the future.


V4879AB    |    Lucca, Tuscany   |    €5,500,000

Just a few minutes from the walls of the historic town of Lucca, this fantastic 17th century villa, once used as a summer residence by the local nobility, enjoys breathtaking views over the Tuscan landscape. The property comprises a stunning restored, 4 storey villa of 1,343 sqm with 11 luxurious bedrooms. It also features elegant reception rooms and dining halls with frescoes which testify to the original Roman origins of the site and a chapel. In addition, a former barn has been restored and houses 2 further apartments with a total of 5 additional bedrooms. The buildings are set in delightful landscaped gardens with 2 swimming pools and a tennis court. The sale also includes 8 hectares of olive groves and vineyards in perfect condition which provide excellent oil and wine.

4473     l  Castellina in Chianti, Tuscany      l      €12,000,000

NEW! Large wine and olive oil farm of the highest quality with 166 hectares in the heart of Chianti Classico, 40 km from Florence. This prestigious property complex dating back to the year 1000 AD has a historic villa, multiple further buildings, park, swimming pool, lemon house, wonderful terraces, loggias and belvedere. State-of-the-art wine cellar for the production of wine, and olive oil mill. Italian excellence in the heart of Tuscany. The vineyard covers 19.5 hectares, the olive grove 21.5 hectares, the forest 105 hectares and the remaining land is planted with fruit trees in production. The wine produced is Chianti Classico as well as riserva and vin santo. The nearest town is Castellina in Chianti. €12 million.

V3908AB    |   Montepulciano, Tuscany    |    €4,500,000 

In a wonderful panoramic location, about 2km from the centre of Montepulciano, this property comprises a sumptuous villa with 10 beautifully decorated suites and a cottage, a restaurant, a wine cellar and an infinity pool. The property is surrounded by wonderful gardens which provide a peaceful haven of relaxation. Renovated in the year 2000, the 16th century property was once the country residence of a noble family of Montepulciano. There is a Tuscan garden, with olive trees and flowers which leads to the infinity pool. There are also various other gardens around the Villa that change their colours and scents with the seasons. In spring, there is a sea of wild flowers while during the summer the lavender and rosemary bloom.

V5092CR    |    San Gimignano, Tuscany    |    Price on Request

In a superb panoramic position between Certaldo and the iconic town of San Gimignano, 50km from Florence and Siena, this wonderful medieval property dates back to the 13th century. The property comprises a restored manor house of approx 3,500 sqm divided into apartments and is currently used as an accommodation business with a pool. The sale also includes 285 hectares of land with 30 hectares of vineyards, 1,600 olive trees, woodland and arable land. The property is surrounded by a classic Italian garden with two large terraces, a swimming pool and a pergola from which you can enjoy a fantastic view of San Gimignano and its countryside.

V5455V   |   San Miniato, Tuscany   |   €2,500,000

This beautiful farm dates back to the 1700s and is set on 54 hectares of land comprising vegetable crops, two vineyards, an olive grove, arable land and coppice. The modern organic farm produces large quantities of various vegetables, aromatic herbs, strawberries and of course, wine. The main house has been completely restored in keeping with the traditional rustic Tuscan style with a total of 6 bedrooms, 7 bathrooms, 2 living rooms and a sumptuous open plan kitchen leading to a dining area, which features an amazing fireplace. The property also includes several outbuildings.

V56515   |   Chianti, Tuscany   |  €7,500,000

Prepare to be amazed by this luxury 17th century Chianti estate, located just a few kilometres from Florence. The outstanding property belongs to a noble family, who settled there in the year 1000 and have carried out important changes and improvements up to the present day. The vast estate comprises a main villa and numerous other buildings including a chapel, lemon house and stables and is surrounded by 230 hectares of land including vineyards, woods, coppice and arable land. The impressive home, as well as being a wine and olive producing company, is often used as a location for weddings, ceremonies and other events due to its luxurious interior, beautiful grounds and majestic views.

V57071   |   Cetona, Tuscany   |   €5,800,000

Set upon 100 hectares of vineyard, olive grove, arable land and woods, this enchanting property includes two farmhouses (one in need of restoration), as well as a storage barn and several other outbuildings.. Situated just 3km from the medieval village of Cetona, the renovated farmhouse is on three levels and exhibits plenty of rustic charm and authentic features. Further to this, the hilltop property also enjoys a swimming pool, panoramic views and desirable privacy.

V4151AB   |   Monteroni d’Arbia, Tuscany   |   €2,500,000

Immersed in greenery and surrounded by farmland, this historic property near Siena dates back to 1550 and has been completely renovated to combine modern comfort with original Tuscan charm. The main house and annex have been divided into apartments and are currently being used as tourist accommodation. A superb saltwater pool and 3 hectares of land, some of which is a vineyard, complete this wonderful property, not to mention the photovoltaic power and secure surveillance system.

V56475   |   San Miniato, Tuscany   |   €5,500,000

In a superb hilltop location, this fabulous historic property offers a villa with 16th century origins, a vast 205 hectares of land with vineyards and olive groves and panoramic views stretching as far as San Gimignano, Volterra and the open sea. Many outbuildings for residential, production or commercial use are also included in the sale, as well as a large fully equipped winery cellar with a production capacity of 210,000 bottles.

V3877M   |   Florence, Tuscany   |   €9,000,000

In the rolling hills of the Chianti countryside sits this impressive 11th century castle with a further farmhouse, restored barn, church and other buildings. The 5 storey castle has been completely renovated, preserving its original features and historical importance. The farmhouse has been divided into 6 apartments, all equipped with modern comforts, while the barn comprises a garage and an indoor heated swimming pool, which is connected to an outdoor pool for the summer months. The property has a total of 25 bedrooms, 15 bathrooms and 62 hectares of land including 11 hectares of vineyard, 14 hectares of olive grove and 37 hectares of woodland.

9158   |   Chianti, Tuscany   |   €1,500,000

Originally a 1700s mill, this delightful stone farmhouse has been carefully restored into a rustic 5 bedroom property whilst still maintaining its original charm and features. There’s also a beautiful neighbouring annex comprising a further 2 bedrooms, a garage, wine cellar and a ruined building with potential to be transformed into a residential space. The charming property also enjoys 8 hectares of vineyard, olive grove and orchard and is completed by a wonderful garden with a swimming pool, panoramic views, a pergola and a tranquil seating area.

V57846   |   Lucca, Tuscany   |   €3,950,000

This property exemplifies the ultimate mansion, located just a few kilometres from the beautiful historical centre of Lucca and less than 30 minutes from the coast of Versilia. Conveniently located in a private yet accessible location surrounded by lush greenery and panoramic views of vineyards, the property consists of 3 main buildings; the villa, the farmhouse, the private chapel and a storage building. With a total of 12 bedrooms and 8 bathrooms, the unique residence is surrounded by 5 hectares of land, which includes a centuries-old ancient park, an olive grove, a vineyard in production and a glistening swimming pool.

V57117   |   Gambassi Terme, Tuscany   |   €1,700,000

Surrounded by 52.7 hectares of land with a hunting reserve and Chianti DOCG vineyards, this incredible farm comprises 4 main buildings, several other buildings and a total of 13 bedrooms. Characterised by an impressive watchtower, the property is located between Siena and Florence and enjoys panoramic views of the medieval town of San Gimignano. Restoration required.

V5543AB   |   Siena, Tuscany   |  €3,950,000

Accessed via a beautiful tree-lined avenue, this 17th century prestigious villa, currently used as tourist accommodation, specialises in the production of oil and wine. The property includes 4 buildings divided into 7 restored apartments of various sizes, 2 swimming pools, beautiful arched porches, vaulted ceilings, original fireplaces and spacious rooms. The surrounding land totals 10.5 hectares.

V5347AB   |   Sinalunga, Tuscany   |   €3,500,000

Prestigious panoramic hilltop complex, located in the centre of a large agricultural estate with about 63 hectares of land. The land includes 13 hectares of olive groves, 10 hectares of vineyard and 40 hectares of wood, pasture and arable land and a swimming pool. With 20 bedrooms and 20 bathrooms, the complex is made up of a main villa and five other buildings used as homes, a private chapel and annexes.

V4735TS   |   Tuscany   |   Price on Request

Located in the beautiful Tuscan landscape near Arezzo, this vast historic estate is a luxury accommodation and event business with an extensive farm of 377 hectares, which includes vineyards, olive groves, woodland and more. The main 5 storey villa operates as a hotel with 24 suites, wine cellars, an osteria and tasting room, restaurant, billiard room, church and function rooms. There are also 6 annexes that are home to 16 apartments and a wellness centre. In total, there are 44 bedrooms and 44 bathrooms. FURTHER DETAILS ON REQUEST.


7207   |   Montalcino, Tuscany   |   Price on Request

In the enchanting setting of the Crete Senesi, this winery features a wonderful farmhouse, a panoramic swimming pool, 13 hectares of land and cellar production of the excellent world-renowned wine of the area. With views of the surrounding rolling hills, the privately situated farmhouse has been perfectly restored with 9 bedrooms and 8 bathrooms and is full of characterful features such as exposed beams, terracotta tiles and fireplaces.

5299   |   Florence, Tuscany   |   €3,200,000

On the banks of the Arno river, in a hilly and panoramic position is this wine estate with a 15th century manor house and 10 hectares of land. Producing up to 4,000 bottles of wine per year, the property is immersed in the Florentine Chianti landscape, characterised by cypress trees and famous vineyards. The manor house currently comprises 20 bedrooms and 20 bathrooms with the possibility of creating more through the conversion of the old cellars. Alternatively, these could instead be turned into a larger cellar to increase the annual production of wine.

9593   |   Chianti Valdarno, Tuscany   |   Price on Request

An ancient hamlet with a perfectly restored period villa and farmhouse, encompassed by 434 hectares of land. In a dominant position, the core of the estate consists of 3 main bodies which are connected internally by cellars, and externally by courtyards and hallways, which also delimit the two gardens. Altogether, this Tuscan estate offers 50 bedrooms and 50 bathrooms, as well as vineyards, olive groves, a fountain, swimming pool and lovely views of the valley below.

6587   |   Gaiole in Chianti, Tuscany   |   €11,500,000

In the exclusive world-famous Chianti Classico setting, this wine and oil producing ancient estate consists of 20 hectares of amazing land, partly cultivated with excellent wine, oil, arable land and forest. The buildings included in this estate include a restored villa with ancient features and four apartments, a farmhouse divided into two apartments and two further farmhouses in need of renovation. Wonderful outdoor spaces make this property even more special such as the panoramic swimming pool situated at the top of a hill, private terraces with breathtaking views and well maintained gardens.

9254   |   Chianti, Tuscany   |   €11,000,000

Extending over 133.7 hectares of land, largely used for the production of wine and oil, this ancient hamlet with a winery and farmhouse is located in the picturesque hills in the heart of the prestigious Chianti Classico area. The main manor house dates back to the 17th century and hosts the equipped wine cellar with an annual production of 75,000 bottles with potential to be increased to 415,000. A separate farmhouse hosts 4 individual apartments while another detached house offers additional living space, bringing the total to 15 bedrooms and 18 bathrooms.

7747   |   Dicomano, Tuscany   |   €5,500,000

Prestigious and historic wine farm straddling the Chianti Rufina and Mugello areas with 350 hectares of land and hunting reserve. The extensive property comprises three hamlets, two of which host villas and apartments housing up to 160 beds in total and the third has a former convent, hunting reserve and dilapidated farmhouse to be restored. With 15 hectares of olive groves and 7 hectares of vineyards, there are also two beautiful swimming pools, a barbecue area, a range of sports and entertainment activities and of course remarkable views.

6322   |   Siena, Tuscany   |   €13,000,000

A scene of frequent battles since the 12th century, this extraordinary Sienese castle is now very important in the production of world-famous wines. Steeped in history and set on 44 hectares of vineyards, olive groves, woods and arable land, the 30 bedrooms, 20 bathrooms and large communal areas within the castle have been restored to a high standard, allowing guests to relive the atmospheric period residence without sacrificing comfort and elegance.

7655   |   Vinci, Tuscany   |   €4,800,000

Situated in the beautiful Florentine countryside in a panoramic position, this eye catching residence offers 18 bedrooms and 22 bathrooms, spread across the main villa and a farmhouse with additional apartments. The imposing property dominates the entire landscape embellished by Chianti hills, were rows of centuries-old vines alternate with majestic olive trees. 35 hectares of land complete the property, mostly populated by Chianti DOCG vineyards.

8916   |   Pontassieve, Tuscany   |   €7,850,000

A few kilometers from Florence, an important organic wine and oil farm with about 40 hectares of land, and a winery for the production of oil and wine. Historic villa and wonderful farmhouse complex to be restored. Excellent accommodation business and building land located in an excellent position near the town of Pontassieve.

6676   |   Chianti, Tuscany   |   €2,200,000

With 18th century origins, this property consists of a main villa, a caretaker’s house and a further 7 apartments, each with private courtyards. 17 hectares of land surrounds this these buildings, which includes 120 olive tress and 2.5 hectares of Chianti Classico vineyard. In total, there are 13 bedrooms and 9 bedrooms plus a wonderful swimming pool and panoramic terrace with views of the estate and surrounding countryside.

V56291   |   Chianti, Tuscany   |   €42,000,000

This breathtaking castle is what dreams are made of! In a fantastic private yet convenient location between Florence and Siena, the property is home to an impressive 80 bedrooms, 50 bathrooms and 1200 hectares of land. Built in 1424 by the noble Pucci family, the castle has welcomed many illustrious visitors over the centuries. Within the castle, there’s a beautiful chapel and spectacular natural wine cellars and beyond the castle are over 50 other farmhouses also included in the sale. The vast land attached to the property features 26 hectares of vineyard, 14 hectares of olive groves, a tennis court, swimming pool and lots more.


Drop us a line at [email protected] with your requirements or visit our website casatuscany.com to see our full range of properties. Join our email list here to receive updates on properties for sale, news and reductions.

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