Chianti
CHIANTI HILLS REAL ESTATE, ITALIAN PROPERTY FOR SALE IN CHIANTI, WINE ESTATE FOR SALE IN CHIANTI
Looking for a villa or a wine estate on the Chianti Hills? Or maybe you prefer a farmhouse for sale on the Chianti Hills? We offer an ample selection of properties, both restored and to be restored, in the beautiful countrysides of Tuscany, between Arezzo, Siena and Florence.
Romolini Immobiliare offers an exclusive selection of villas, apartments and houses on the Chianti Hills with panoramic landscape, wine estate, farms, wineries with vineyards, period villas, castles, renovated farmhouses, luxury apartments, hunting reserves, villas with gardens, estate with vineyards and farmhouses with olive groves all over Tuscany.
CHIANTI HILLS IN TUSCANY, LUXURY ITALIAN PROPERTY FOR SALE | Chiantishire
Ref. 2983 Resort Via Francigena
€ 4,500,000
BOUTIQUE HOTEL WITH WELLNESS CENTER FOR SALE IN SIENA, TUSCANY
Tuscany - Siena - Siena
Interiors: 1,125 sqm
Bedrooms: 14
Bathrooms: 14
Exteriors: 51.70 ha
Pool: Yes
This resort is a breathtaking historical dwelling dating back to the year 1000, majestically located between Siena and Monteriggioni. This prestigious property represents an invaluable resource for the territory, offering the impression of being immersed in a natural park where human architecture and nature seamlessly blend. The estate encompasses a total of 51.7 hectares, featuring roughly 2.0 hectares of fenced grounds and 49 hectares of lush woodland. Access to the property is gained via an ancient road accredited as part of the complex network of the Via Francigena.
The complex underwent a meticulous renovation between 2007 and 2013 with the goal of creating a high-quality structure that fully integrates into its unique environmental context. The heart of the residence is a stunning internal courtyard that features a perfectly functional wood-burning oven and provides access to the primary living quarters. Accommodations consist of eight elegant suites that combine historical charm with modern comfort, featuring stone and brick walls, wooden beamed ceilings, and country-chic furnishings. These include four standard suites, two luxury suites equipped with fireplaces, and two expansive prestige suites that offer two bathrooms each. Additionally, a separate autonomous villa dominates the property, offering a large living room with a fireplace on the ground floor and two bedrooms on the upper level.
The estate is fully equipped for luxury hospitality and exclusive events, boasting a panoramic 10 × 6 m swimming pool and terrace that offer breathtaking views of Siena and the surrounding hills. Culinary excellence is found at the internal restaurant which serves traditional Tuscan dishes using seasonal ingredients from the property’s own organic garden. For wellness, the SPA has been masterfully carved into the historic dungeons, providing an indoor heated pool with hydromassage, a sauna, a Turkish bath, and emotional showers. Event capabilities are anchored by the eventhall, a structure capable of hosting 120 people, with approved plans already in place to replace it with a sophisticated glass and metal structure to further enhance the landscape.
Danilo Romolini
Sales Manager
6 years with Romolini
Ref. 1526 Castello de' Medici
€ 2,800,000
ITALIAN CASTLE FOR SALE IN THE CHIANTI WINE AREA
Tuscany - Arezzo - Bucine
Interiors: 1,040 sqm
Bedrooms: 12
Bathrooms: 12
Exteriors: 1.14 ha
Olive grove: 0.80 ha
Pool: Yes
Located in a small hamlet on the hills of Chianti, in the Tuscan countryside, 12th century medieval castle with luxury accommodation business, apartments, gym, pool, park and olive grove.
The castle (800 m²) is located in the center of the medieval hamlet, and constitutes one of the four sides of the main square. On the inside (and a small annex 50 m away) we can find nine luxury mini-apartments with just as many double (or twin) bedrooms with en-suite bathrooms.
The property is then completed by three independent apartments (for a grand total of 150 m²) located in the surrounding hamlet, a gym with dressing room (70 m²), a car garage (20 m²) and some storage rooms.
The building boasts an Italian garden on the left side, accessed both through the castle and via a metal gate from the road.
A short distance from the castle, descending towards the base of the hill on the other side of the hamlet, split on various terraces, we can find the beautiful 3,400-m² park with the 14 × 6 m panoramic pool. Last but not least, the property is fitted with a 8,000-m² 160-tree olive grove in perfect conditions.
Iacopo Rossi
Agronomist, Vineyards & Wineries Expert
2 years with Romolini
Ref. 2887 Villa Boccaccio
€ 1,650,000
VILLA WITH POOL AND OLIVE GROVE FOR SALE IN CERTALDO, TUSCANY
Tuscany - Florence - Certaldo
Interiors: 721 sqm
Bedrooms: 19
Bathrooms: 13
Exteriors: 1.71 ha
Olive grove: 1.13 ha
Pool: Yes
On the hills of Florence, not far from Certaldo and Montespertoli in the heart of Chianti, restored villa with outbuilding and olive grove for sale. The property is currently divided into six independent apartments, very suitable for an accommodation business, and has a panoramic swimming pool overlooking the surrounding countryside.
DESCRIPTION OF THE BUILDINGS
The main villa (397 m² – 4,272 ft², 12 bedrooms and 9 bathrooms) is a two-story, red-painted and fully renovated building divided into four independent apartments:
- Apt. Siena: living room with kitchen, three bedrooms and two bathrooms;
- Apt. Lucca: living room with kitchen, three bedrooms and three bathrooms;
- Apt. Florence: living room, kitchen, three bedrooms and two bathrooms;
- Apt. Pisa: living room, eat-in kitchen, three bedrooms and two bathrooms.
The farmhouse (268 m² – 2,884 ft², 5 bedrooms and 3 bathrooms), on the other hand, is divided into two units, one on each floor, and has two convenient exclusive garages. The renovation aimed to maintain most of the salient features of the structure such as the brick vaults and terracotta floors on the ground floor and the chestnut beams on the second floor. The Livorno apartment, inhabited by the owners, is also equipped with a photovoltaic system.
- Apt. Livorno: living room, equipped kitchen, office, two bedrooms and two bathrooms;
- Apt. Grosseto: living/dining room with kitchen, three bedrooms and one bathroom.
The old barn (56 m² – 602 ft², 2 bedrooms and 1 bathroom) has been fully renovated and converted into a charming two-story annex including living/dining room with kitchenette, two bedrooms and bathroom. Here, too, the renovation has preserved the Tuscan character of the building, which still shows wooden beams and terracotta floors.
Danilo Romolini
Sales Manager
6 years with Romolini
Ref. 2767 Castelletto Impruneta
€ 1,340,000
SMALL CASTLE TO BE RESTORED FOR SALE IN TUSCANY, IMPRUNETA
Tuscany - Florence - Impruneta
Interiors: 400 sqm
Bedrooms: 6
Bathrooms: 4
Exteriors: 1.43 ha
Olive grove: 0.70 ha
On the first hills of Chianti, not far from Impruneta, small castle to be restored for sale. The building needs major renovation and modernization works but could be a great starting point for a small charming accommodation business in one of the most sought-after places in Tuscany.
DESCRIPTION OF THE PROPERTY
The castle (290 m² – 3,120 ft², 4 bedrooms and 3 bathrooms) is a building developed mainly in height, decorated with friezes and crenellations, arranged on four floors connected internally by various staircases. On the ground floor, accessible from the numerous doors in the garden, are the living areas, with cozy decorated rooms, and a private chapel. . Going up the staircase one initially reaches a terrace (63 m², accessible by a door at mid-ramp) and then the sleeping area on the first floor, where four bedrooms could be obtained (one of which has an exclusive terrace of 12 m²). Going up further we instead find ourselves in the tower proper: on the second floor we find a room with access to the large panoramic terrace (90 m²), on the third another room with access to the panoramic terrace in the turret (15 m²).
Next to the tower there is a guesthouse (90 m² – 968 ft², 2 bedrooms and 1 bathroom) on two floors: in the basement there are the cellars (two rooms), while on the ground floor you could easily make a small independent house with living room, two bedrooms and bathroom.
Also part of the property are a small agricultural outbuilding (10 m² – 107 ft²) and the former pigsty (10 m² – 107 ft²), both usable as storage for tools.
The tower is surrounded by a tree-lined park of 15,980 m² that also includes a smallolive grove (to be recovered but with good production potential). The wooded part (about 8,000 m²) could be easily reclaimed and cleared to further expand the park. In front of the building is a chemin-de-ronde with several panoramic terraces, the famous Belvederi, overlooking the vineyards and Chianti hills: the castle in actually enjoys a privileged position on top of a hill, which allows for uninterrupted views of the surrounding countryside.
Danilo Romolini
Sales Manager
6 years with Romolini
Ref. 2739 Tenuta Belsogno
€ 5,000,000
HISTORIC ESTATE WITH RENAISSANCE VILLA AND ORGANIC VINEYARDS FOR SALE IN CHIANTI
Tuscany - Florence - Montespertoli
Interiors: 2,604 sqm
Bedrooms: 25
Bathrooms: 20
Exteriors: 123.92 ha
Vineyards: 27.15 ha
Olive grove: 24.86 ha
On the hills of Tuscany between Empoli and Florence, in a very panoramic position, estate with prestigious historical villa, farmhouses and 27 ha of vineyards for sale. The property consists of restored historic buildings with a total of 25 bedrooms that are currently used for accommodation, as well as a modern winery.
The main villa (500 m² – 5,380 ft², 5 bedrooms and 6 bathrooms) is an imposing building dating back to the 16th century, in typical late Renaissance style, and features large ornate reception halls and refined rooms, as well as five bedrooms and six bathrooms.
Not far from the villa is an outbuilding (226 m² – 2,431 ft², 7 bedrooms and 5 bathrooms) that has been divided into three independent guest units:
- Apt. A (44 m²): living room with kitchen, two bedrooms and bathroom;
- Apt. B (114 m²): living room with kitchen, three bedrooms and two bathrooms;
- Apt. C (68 m²): living room, storage room, two bedrooms and two bathrooms.
The farmer’s house (320 m² – 3,443 ft², 10 bedrooms and 7 bathrooms), on the other hand, is a rustic, typically Tuscan-style building divided into four guest apartments:
- Apt. D (57 m²): living room, two bedrooms and bathroom;
- Apt. E (102 m²): living room, three bedrooms and two bathrooms;
- Apt. F (69 m²): living room, two bedrooms and two bathrooms;
- Apt. G (92 m²): living room, three bedrooms and two bathrooms.
The old barn (158 m² – 1,700 ft², 3 bedrooms and 2 bathrooms), on two floors, has also been converted into a charming guest cottage consisting of living room with kitchen, three bedrooms and two bathrooms.
The winemaking cellar with agricultural outbuildings (1,400 m² – 15,064 ft²) has rooms for processing grapes, winemaking and aging wines, as well as warehouses for storing products.
Lorenzo Guerri
Enologist, Vineyards & Wineries Expert
3 years with Romolini
Ref. 2130 Villa Design Vinci
€ 1,520,000
LUXURY MODERN VILLA FOR SALE IN VINCI, ONE HOUR FROM FLORENCE
Tuscany - Florence - Vinci
Interiors: 630 sqm
Bedrooms: 6
Bathrooms: 7
Exteriors: 3,070 sqm
Pool: Yes
In a panoramic position on the hills of Tuscany, not far from Florence and Vinci, luxury villa with garden and pool. The building (600 m²) is modern in style, with simple geometric shapes and bright rooms, including 6 ample bedrooms, beautiful living areas and even a wellness center. Outside, over 3,000 m² of garden surrounds the house and house the 13 × 6 m swimming pool with view over the surrounding vineyards and olive groves.
DESCRIPTION OF THE BUILDINGS
The villa (600 m² – 6,456 ft², 6 bedrooms and 7 bathrooms) is laid over three floors, each with direct access from outside thanks to the terraced garden surrounding the building. Entering the ground floor one finds a bright living room connected to the kitchen with its own dining area. The living area is then completed by a laundry and a guest bathroom. A corridor leads to the first sleeping area made up of a studio, a bedroom with private bathroom and two more bedrooms sharing a bathroom.
A staircase from the living room leads to the upper floor, to a second living area, also characterized by ample windows opening onto a porch. From here one can then enter the dining area (connected to the underlying kitchen by a dumbwaiter). The central corridor leads to the second sleeping area housing a master bedroom with private bathroom and walk-in closet, a second bedroom with private bathroom and walk-in closet and a third bedroom with an independent bathroom.
Descending to the lower level of the villa, again from the living area on the ground floor, is a fitness area, brightened by a full-wall window and fitted with a bathroom with shower.
Outside, in a defiladed position from the villa, is a garage (30 m² – 323 ft²) with room to shelter up to two cars.
Danilo Romolini
Sales Manager
6 years with Romolini
Ref. 3092 Cantina Sant'Anna
€ 1,500,000
ORGANIC WINE ESTATE FOR SALE IN VINCI, CHIANTI
Tuscany - Florence - Vinci
Interiors: 608 sqm
Bedrooms: 0
Bathrooms: 1
Exteriors: 6.67 ha
Vineyards: 5.82 ha
Olive grove: 0.28 ha
Located on the gently rolling hills of Vinci and Cerreto Guidi, about forty minutes from Florence, winery for sale. The estate covers a total area of approximately 6.7 hectares, combined, ideal for smooth and rational agricultural management, all completed with organic certification.
- Vineyards surface: 5.8241 hectares (14.4 acres)
- Appellations: Chianti DOCG (5.2508 ha) + Toscana IGT (0.5733 ha)
- Varieties: Sangiovese, Colorino, Foglia Tonda, Cabernet Sauvignon, Malvasia Bianca, Trebbiano, Viognier, Ciliegiolo
- Training: Guyot (4,400 vines / ha)
- Planting years: 2003 – 2014
- Altitude and exposure: 40 m asl (south)
- Soil composition: clayish
- Yearly production: about 8,000 bottles + 382 hl bulk
The estate's biodiversity is completed by a specialized olive grove with 98 mature Leccino trees. The production (registrable as Toscana IGP) yields every year an extra virgin olive oil of extraordinary purity and freshness, ideal for complementing the estate’s product portfolio.
The operational core of the company is represented by a highly functional complex. The wine cellar (414 m²) is a real operational structure with very high capacity, equipped with a range of thermally controlled stainless steel tanks (1,131 hl) complemented by an 11.2 hl barrel cellar. Other buildings are intended for agricultural storage for vehicles and equipment (194 m²).
Near the entrance gate, a large flat area is perfectly suited for the realization of an exclusive stop and motorhome storage area, potentially integrated with an intimate bistro-restaurant ideal for tasting and direct enhancement of the wines and products of the cellar. The above-ground swimming pool located in front of the cellar allows for organizing events and tastings in an alternative format.
Lorenzo Guerri
Enologist, Vineyards & Wineries Expert
3 years with Romolini
Ref. 3081 Villa del Vescovo
€ 1,980,000
LUXURY COUNTRY HOUSE WITH POOL FOR SALE IN GAIOLE IN CHIANTI, TUSCANY
Tuscany - Siena - Gaiole in Chianti
Interiors: 333 sqm
Bedrooms: 3
Bathrooms: 4
Exteriors: 3.10 ha
Pool: Yes
In a panoramic position on the hills of Chianti, not far from Gaiole, elegant historic farmhouse for sale developed on two levels, characterized by well-distributed environments, charming elements, and pleasant outdoor spaces. Formerly the residence of a bishop, the house has been finely renovated with fine materials and combines reception rooms, characterized by ceilings over five-meters high, with more cozy and intimate rooms that ensure excellent livability.
On the ground floor, the property features an entrance, a large living room with fireplace, a dining room, a kitchen, a bedroom, a bathroom, a cellar, a loggia, a technical room, and an additional bathroom. The first floor hosts a hallway, two bedrooms, two bathrooms, two storage rooms, and a partially usable attic.
The property is immersed in a 3.1-hectare park embellished with an 11 × 4.5 m swimming pool with a solarium, perfect for relaxing moments and enjoying the tranquility and the picturesque landscape of Chianti, as well as a votive shrine, a shed, and a well, elements that enhance the authentic character of the property.
Danilo Romolini
Sales Manager
6 years with Romolini
Ref. 3078 Casale Montecchio
€ 2,950,000
FARMHOUSE WITH VINEYARD, OLIVE GROVE AND PRIVATE LAKE FOR SALE IN TUSCANY
Tuscany - Florence - Florence
Interiors: 1,604 sqm
Bedrooms: 5
Bathrooms: 4
Exteriors: 44.85 ha
Vineyards: 7.63 ha
Olive grove: 8.47 ha
In the Tuscan countryside, in a private and secluded position surrounded by greenery, rural property of approximately 44.8 hectares, featuring a private lake, an articulated complex of buildings and extensive areas of vineyards and olive groves.
The property comprises a main farmhouse, an agricultural outbuilding and an agricultural warehouse, in addition to further rooms used as storage and service areas. The presence of the agricultural buildings and land makes the estate particularly suitable for the continuation of an agricultural activity, while at the same time offering interesting possibilities for residential and tourism-accommodation development.
The main farmhouse is arranged over two floors. The ground floor is currently used as five storage and warehouse rooms, in addition to two further rooms.
The first floor houses two independent apartments, both with independent access via external staircases located on opposite sides of the building.
Apartment A is arranged over two levels. The first floor comprises a large kitchen with dining area, a living room, a bedroom and a bathroom; on the upper floor there is a second bedroom.
Apartment B, arranged on a single level, comprises a kitchen, living room with dining area, two bedrooms and a bathroom.
The agricultural outbuilding, featuring rustic-style interiors and an original antique fireplace, comprises a room for agricultural workers, a dining room, a storage room, a warehouse and a bathroom.
The agricultural warehouse is arranged over two levels. The basement floor houses an oil storage room, a bottling room, a warehouse, an ageing room and a canopy. The ground floor, located in a further wing of the complex, comprises a hallway, two warehouses, a wine-making room and a bathroom.
Danilo Romolini
Sales Manager
6 years with Romolini
Ref. 2515 Podere Sant'Agnese
€ 2,950,000
ESTATE WITH RENOVATED FARMHOUSES FOR SALE ON THE CHIANTI HILLS, TUSCANY
Tuscany - Siena - Castellina in Chianti
Interiors: 957 sqm
Bedrooms: 19
Bathrooms: 22
Exteriors: 52.09 ha
Olive grove: 7.63 ha
On the Chianti hills, in a very panoramic position near Castellina and Barberino Val d’Elsa, 52.1-ha estate with Agriturismo and olive grove for sale. The property, finely restored by the current owners, consists of rural buildings for a total of over 900 m² that currently house 19 bedrooms, almost all of which are intended to accommodate guests. The land surrounding the farmhouses is covered by woods and olive groves.
Basic services are available in the nearby village of Castellina in Chianti (7km; 10'), while if you are looking for something a little more well-stocked, just drive to Poggibonsi (13km; 20'). The Florence-Siena motorway junction is also in Poggibonsi, making it possible to travel through much of Tuscany and visit some of the region’s most renowned centers (Montepulciano, Pienza, Montalcino, Cortona, San Gimignano...).
Gionatan Guidi
Licensed Real Estate Agent
20 years with Romolini




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