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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
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 €3,800,000
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.
V5258PV | Greve in Chianti, Tuscany | €6,500,000
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.
V63575 l Sarteano, Tuscany l €15,000,000
Fine winery and resort with spa facilities and wine cellar near Sartano. 125 hectares including vineyards and olive groves. Prestigious winery in energy class A and agricultural estate with luxury resort, spa, and truffle reserve, 20 km from Montepulciano, Pienza, and Lake Trasimeno. Sangiovese to Cabernet and Merlot, with an average annual production of approximately 100,000 bottles in the modern cellar built in 2007, equipped with all the necessary for the vinification, bottling, and conservation.
V56291 l Chianti, Tuscany l €42,000,000
Historic dream castle with a private chapel and numerous towers and details dating back in time bearing the Brunelleschi signature dominating one of the Tuscan hills, surrounded by more than 1200 hectares of land and serving as the capital of the well-established company that produces excellent wines and oil; in addition there is a number of farmhouses used for production or as accommodation for guests and workers.
V63545 l Monteriggioni, Tuscany l €3,800,000
Historic 18th century restored villa enveloped in 205 hectares (506 acres) of absolute privacy, offering olive groves, an exclusive winery and pool potential. In the Chianti hills, at 350 meters above sea level, halfway between the magnificent city of Siena and the medieval castle of Monteriggioni, just 40 minutes south of Florence. The villa dominates the enchanting scenery over its 205 hectares/506 acres of private land which include its first vineyards which were planted back in the 1970s.
V63485 l Montepulciano, Tuscany l €15,000,000
Organic Winery boasting a historical farmstead, 31 hectares of vineyards, cellar and olive groves for sale near Montepulciano, Siena. This breathtaking estate offers an extraordinary opportunity to acquire a turnkey organic winery, with expansive vineyards, state-of-the-art winemaking facilities, and historical farmhouses. Located in one of Tuscany’s most iconic wine regions, Montepulciano, it combines tradition, modernity, and natural beauty—an idyllic setting for producing world-class wines and olive oil.
V63585 l Asti, Piedmont l €2,550,000
An outstanding 13.3 hectare/32 acre estate with a luxury 17th century villa, cellar with infernòt, pool, and lake for sale in Asti, Piedmont. The U-shaped manor house dominates the hill with spectacular 360-degree views of the countryside, surrounded by a park with swimming pool, vineyards and a state-of-the-art winery with cellars.
V62855 l Chianti, Tuscany l €10,000,000
102-hectare/252-acre estate for sale in the heart of Chianti Classico with vineyards, winemaking facilities and historic villa with farmstead. About 10 km north of Siena, the estate covers the municipalities of Radda in Chianti and Castelnuovo Berardenga, made of rolling hills, valleys and a private lake. The vineyards cover 70.4 acres (28.5 hectares), with rights for an additional 7 hectares (17 acres) to be replanted, and each has its own unique terroir: a combination of soil, altitude and exposure, resulting in wines of extraordinary complexity.
V5060AB l Montalcino, Tuscany l €2,750,000
Extensive farm, winery and accommodation business is located in a tranquil and panoramic position a few kilometres from Montalcino and San Giovanni d’Asso, Pienza and Montepulciano, within the Val D’Orcia, a UNESCO World Heritage Site. The sale includes 30 hectares of land with a large garden, terrace and pool, arable land and woodland, as well as extensive producing olive groves, DOC Orcia registered vineyards producing 5-6,000 bottles of excellent wine per year and truffle land. Cellar of 200 sqm fully equipped for bottling
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.
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