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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.
V61235 l Chianti, Tuscany l €8,000,000
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.
V56515 l Chianti, Tuscany l €7,500,000
Splendid ancient noble residence, a few kilometres from Florence. The Villa, built around the year 1600, is surrounded by vineyards and olive groves, a panorama that can be appreciated from the windows of the frescoed halls and the gardens of the villa, one of which is Italian style with the classic essences of this one. The estate extends on the southern slope of the slopes of Montalbano, in the municipality of Vinci, Leonardo’s homeland, for 230 ha at an altitude ranging from 98 m, overlooking the city of Vinci, to 642 m at the highest peak. The scrupulous attention to wine has also made the estate stand out, thanks also to the high quality products.
V59595 l Castelfiorentino, Tuscany l €5,500,000
A wonderful Chianti DOC organic vineyard and winery, with 22.4 hectares, a villa with pool, spa, banqueting halls and top-class amenities for sale 20 km from Florence, in an enchanting and classic Tuscan landscape of vineyards, olive groves, ancient towns and some the most world’s prestigious wineries and estates. With a dominant 360-degree open views, this property is a superb wine-lovers paradise with 10.9 ha/26.9 acres of organic vineyards producing over 115,000 bottles of the finest Chianti DOC and IGT Toscana wines paired to a wine-making facility built back in 2009 offering over 405 sq m/4359 sq ft sq m of fully equipped premises.
V60807 l San Gimignano, Tuscany l €6,500,000
Situated in a splendid panoramic position in the San Gimignano countryside, this wonderful organic winery consists of a group of buildings with 10 apartments including 8 guest apartments, 63 hectares of land, cellars, offices, warehouses, tasting room, covered parking spaces, machinery shed and a beautiful swimming pool. The hilltop property sits 350 metres above sea level in the Chianti Colli Senesi and DOCG Vernaccia di San Gimignano area and specialises in the production of the most prestigious DOCG, DOC, and “Supertuscans” denominations.
V59641 l San Casciano Val di Pesa l €7,450,000
Reached by a well-maintained driveway surrounded by tall cypress trees, you are immediately greeted by the architectural beauty of the historic villa. The villa is surrounded by its spectacular carefully designed and well-cared for Italian garden. The pool is located in a position of great privacy and with fantastic views. The land of 3.7 hectares is cultivated with vines for 1.5 hectares and olive groves for 2.2 hectares, with a total of 900 olive trees. The annex (currently a tasting room) can be converted in a winery for the processing of the grapes.
V606021 l Castellina in Chianti l €3,500,000
A few minutes from enchanting Castellina in Chianti, beautifully renovated traditional stone villa with 22 hectares including vineyards and an olive grove. The main villa spans 1,100 sqm and features 14 luxurious bedrooms and 17 bathrooms, Main villa + annex and private chapel. The ground floor of the annex serves as a storage area, providing plenty of room for wine and olive oil production. The 22 hectares of land include 2 hectares of vineyards (Sangiovese and Merlot) producing fine wines and over 800 olive trees that yield premium extra virgin olive oil.
V61301 l Chianti, Tuscany l €11,000,000
Prestigious organic winery extending over 133.7 hectares and consisting of an ancient hamlet with winery and farmhouse located in the picturesque timeless hills in the heart of the prestigious Chianti Classico area. 7300 sqm with charming medieval hamlet which includes an elegant manor house dating back to the 17th century of about 1228 sqm, and the splendid underground and perfectly equipped wine cellar of 2077 sqm. 33.1 ha of vineyards, 6.7 ha of olive groves, 47.1 ha of arable land + 40.9 ha of woods + 3.8 ha of pasture. The wines are each year listed in the world’s best wine guides. Production is about 75,000 bottles, with a potential capacity of as many as 415,000 bottles.
V59363 l Chianti, Tuscany l €9,000,000
Winery with castle for sale in the heart of Chianti, just 15 km from Siena. The property of 1,420 sqm dates back to the 10th century and was renovated between 1996 and 2001. A new building was subsequently added to house the wine cellar, offices and tasting room. 48.6 hectares of land inc. vineyard (12.1 ha) which annually produce between 60,000 and 100,000 bottles of high-end DOCG Chianti Classico, Riserva and 2 Supertuscans.
V610721 l San Casciano in Val di Pesa l €3,200,000 negotiable
In the enchanting hills of Chianti, just 30 minutes from Florence, this elegant villa complete with vineyard and olive grove offers a unique opportunity to own a piece of authentic Tuscany. 1,500 sqm property with 5.3 hectares dominated by a fine Chianti Classico DOCG vineyard of 3.2 hectares and an olive grove of 1.1 hectares, with around 350 trees. Wine cellar equipped for producing Chianti Classico DOCG wine.
V5543AB l Siena, Tuscany l €3,950,000
Prestigious 17th century property of 3160 sqm comprising villa, farmhouse, land, garden, 2 swimming pools, vineyards and olive groves in the province of Siena. 4 buildings divided into 7 apartments of various sizes, all renovated. The historic villa, accessed via a beautiful tree-lined avenue, reflects the aristocratic characteristics of the entire property with beautiful porches on the façade both on the ground floor and on the first floor, vaulted decorated ceilings, original fireplaces, terracotta floors and large bright rooms. The farm specialises in in the production of oil and wine (Rosso di Toscana IGT: 100% Sangiovese, Rosso di Toscana IGT: 100% Cabernet Sauvignon, Rosso di Toscana IGT: 100% Merlot, Rosso di Toscana IGT: 100% Syrah).
V61311 l Chianti, Tuscany l €1,200,000
Delightful rustic stone farmhouse with annex and ruin for a total of 650 sqm plus beautiful swimming pool and large amount of land with vineyard, in the renowned Chianti area. The rustic stone farmhouse of about 350 sqm is an old mill dating back to the 1700s which has been completely and carefully restored. 80 sqm garage used as tool shed, a 40 sqm wine cellar fully equipped for wine production with steel barrels, and a third ruined rustic building of 208 sqm to be renovated with potential to become an apartment, wine cellar or restaurant. 9 hectares of land including 8 hectares of Merlot iGT vineyard with 4000 vines, olive grove with 100 olive trees and orchard with 400 trees in addition to arable land and woodland.
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 €10,000,000
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.
V5455V l San Miniato, Tuscany l €2,500,000
This beautiful farm dates back to the 1700s and is spread over 54 hectares of land comprising vegetable crops, two vineyards, an olive grove, arable land and coppice. Originally a podere, the modern organic farm produces large quantities of various vegetables aromatic herbs and strawberries and of course, wine.The property is located in a pretty unspoiled valley nestled in the rolling hills that surround the medieval village of San Miniato. This is a great position as it’s within easy driving distance of the main 4 cities in Tuscany: Florence, Pisa, Lucca and Siena.
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.
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.
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.
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