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.


V5274AB    |    Castellina in Chianti, Tuscany    |    €5,000,000

This 80 hectare wine estate is situated in the heart of the Chianti Classico area in Castellina in Chianti between Florence and Siena. The sale includes a historic villa with a pool as well as 3 restored farmhouses, several business premises and a filly equipped wine cellar. Run as an agriturismo with wine and olive oil for over 20 years, its vineyard consists of 11 hectares of Chianti Classico Gallo Nero with the possibility to increase by a further 15 hectares. There are also 1,500 olives trees, 24 hectares of agriculture land and the rest is woods. Yearly production: 90,000 bottles of high quality wine, sold all over the world.

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.

V4617PV    |    Pisa, Tuscany    |    €2,000,000

This beautiful 18th century winery is located in the Pisan countryside and comprises a recently renovated main villa of approx. 750 sqm, a farmhouse of 500 sqm with a cellar, tasting rooms and 2 apartments (one still to restore). In addition, there are annexes for agricultural use. In total there are 11 bedrooms and 6 bathrooms. The sale also includes 3.25 hectares of land with a vineyard producing 15-18,000 bottles of wine per year. The vineyard produces 15,000 – 18,000 bottles of wine per year made up of: 2,000 bottles white wine, 10,000 bottles of Sangiovese red wine, 4,000 bottles of Super Tuscan red wine, said to be one of the best red wines produced in the Pisa area. The wine is sold in Germany and Switzerland.

V4157PV    |    Florence, Tuscany    |    €3,200,000

Dating back to the 15th century, this impressive property is situated in the hills near Rignano sull’Arno and offers wonderful countryside views. Located about 20km from Florence, the property comprises a historic estate composed of 3 separate buildings divided into 9 apartments providing a total living space of 3,000 sqm. The sale also includes 10 hectares of land including 1 hectare of cultivated vineyards with production of IGT red wine. The current annual production is about 4,000 bottles per year.

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.

V4600AB    |    Castellina in Chianti, Tuscany    |    €10,200,000

This historic renaissance villa and wine estate is located near Castellina in Chianti. With Roman/Etruscan origins, this prestigious property is a well known landmark in the Chianti area, visible from great distances. It has a total area of 4,285 sqm with 19 bedrooms, and scope to increase the accommodation available. The property features a chapel, olive press, vegetable garden and wine cellars carved into the rock with vaults and barrels. The old cellars have been been transformed into spacious dining/reception areas for up to 150 people. Accessed via a 2km private drive lined with Cypress trees. Private heliport. 101 hectares of land including vineyards and olive groves. Wine production of approx 41,000 bottles p.a.

V4913SC    |    San Gimignano, Tuscany    |    €2,950,000

This luxurious historic property is located just 5km from the hill top town of San Gimignano, famous all over the world for its medieval towers, ancient traditions and delightful wine and food. Dating back to the 18th century with parts as old as the 16th century, this beautiful 4 bedroom country house has 400 sqm of living space and a stunning interior. There is an annex opposite that houses a further 1 bedroom apartment and cellars for wine storage and also an old barn that could be restored. The property is surrounded by a delightful garden with a panoramic infinity pool that offers views over the countryside.  The sale includes an additional 14 hectares of private land with vineyards and olive groves that produce certified organic red and white wine and olive oil.

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.

V4441CP    |    Siena, Tuscany    |    €14,000,000 

Steeped in 1000 years of history, this majestic medieval castle is located in the heart of the world famous wine region of Chianti. The castle dates back to the 11th century and is an an elevated position, surrounded by a vast estate of approximately 120 hectares. The land includes 15 hectares of vineyards with a current annual production of 75,000 bottles of Chianti Classico. There are further buildings which are with guest apartments and a private chapel. The property  includes 11 suites and 8 apartments and offers a total floor area of approximately 4,000 sqm. There is also a restaurant with an outdoor setting that can accommodate up to 220 guests, a perfect venue for weddings and events. The former moat has been transformed into a luxurious swimming pool.

V4998AB    |    Cortona, Tuscany    |    €1,600,000

Situated close to the beautiful historic town of Cortona, this extensive property enjoys one of the best Tuscan landscapes, attracting tourists from around the world. Dating back to the 1700s, this distinguished villa bears testimony to its past with a wealth of original features such as the emblem of the Medici family to whom the property once belonged. In an elevated position, this stately building offers 950 sqm of space on 3 storeys above ground. Divided into 4 units it has 10 double bedrooms, 2 single bedrooms, 8 bathrooms and 4 kitchens in total. In addition, there is an ancient chapel, now used for agricultural activities. Surrounded by 2 hectares of fenced parkland, the property features an entrance of ancient cypresses of majestic proportions, an olive grove and a small vineyard of about 2,500 sqm.

V5233AB    |    Gaiole in Chianti, Tuscany    |   €7,300,000 

Winery with several buildings and a total of 25 bedrooms, 15 hectares of vineyards, 2 swimming pools, tennis court and an annual wine production of 95,000 bottles. The property consists of: Residential buildings: 1,820 sqm, agricultural outbuildings, equipped winery and wine tasting area, 15 hectares (37 acres) of vineyards, wine production: approx. 95,000 bottles, 2 swimming pools; one indoor and one outdoor, spa/wellness centre, restaurant. Sporting facilities include a tennis court, a small lake, and table tennis.

V2695C    |    Castelfiorentino, Tuscany    |    €5,000,000 

Medieval hamlet perched on a hill overlooking the whole winery. Located in the heart of Tuscany, near Castelfiorentino, San Gimignano and Volterra. Surrounded by an unspoilt panorama, the property covers over 40 ha of land, including 16 ha of vineyard, a hamlet of 1,057 sqm with three buildings divided into 15 restored apartments. In a secluded position, connected to the hamlet by steps, there is the swimming pool overlooking the vineyards. The winery covers a total area of about 40 ha, including 16 ha of wonderful vineyard. The cellar, the tools and machinery for making, bottling and storing wine are included.

V5230AB    |    Gaiole in Chianti, Tuscany     |    €4,000,000 

10th century winery with a castle comprising 7 bedrooms, 7 bathrooms, 52 hectares of land and an annual wine production of up to 100,000 bottles. There are 5 hectares of olive grove, 30 hectares of woodland, 16 hectares of vineyards, of which annually produce between 60,000 and 100,000 bottles of high-end DOCG Chianti Classico, Riserva and 2 Supertuscans. The grapes: 2.7 hectares of traditional Sangiovese, Canaiolo, Malvasia, 2 hectares of Sangiovese Grosso, 1.5 hectares of Cabernet Sauvignon, 1.5 hectares of Merlot, 8.3 hectares of Sangiovese planted in 2000–2006.

V4897C    |    Terranuova Bracciolini, Tuscany    |   POA

This impressive estate is located in the hills of the Chianti Valdarno, in the heart of Tuscany. The estate comprises a magnificent Art Nouveau villa, a second 19th century villa, a farmhouse with its own 2 hectares and 2 agricultural buildings. The sale includes 170 hectares of land, 16 of which is fertile vineyard and the rest: arable land and a game reserve. All the buildings require various degrees of restoration.  With its wonderful original features including frescoed ceilings, the main villa could become a fabulous stately home once again.


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.

V4948BM    |    Lucca, Tuscany    |    €2,300,000

7km from Lucca, this unique historic property of immense value is located in a peaceful panoramic setting, among the picturesque Lucca hills in the Tuscan countryside. The magnificent property comprises an exquisite 17th century villa, 2 charming lemon houses/orangeries, a well-proportioned guest house and a character farmhouse. It is surrounded by 5 hectares of mature grounds including a vineyard, a large olive-grove with approx. 1,100 olive trees which produce an excellent olive oil and 2 hectares of woodland. The main villa, dating back to the early 1600s, is a perfect example of historic Lucca architecture and is surrounded by a landscaped walled garden with a wonderful nymphaeum to the rear.

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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