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Contatta Romolini Immobiliare


The Valdelsa (often written Val d’Elsa), is a valley crossed by the river Elsa and shares its brders with the Chianti Hills, the Valdarno, the Val di Merse and the Valle di Cecina. Internally split between Upper and Lower Valdelsa, better known respectively as Sienese Valdelsa and Florentine Valdelsa, it includes several important Tuscan hamlet such as Poggibonsi, Castelfiorentino, Certaldo and Colle di Val d’Elsa.

Thanks to the numerous findings unearthed in the area, it’s been possible to have a reliable idea of the history of Valdelsa. Tools, necropolis and pottery testify the presence of Etruscans in the area, while recent archaeological expeditions unearthed the remains of several Roman villas.

Located among Florence, Siena and Volterra, the Valdelsa was an important crossroad on the Via Francigena during the Middle Ages, the period where an intense urbanization of the area took place with the birth of churches, castles and hamlets. Linking Northern Europe with Rome, the Via Francigena contributed to the economical and political development of the area, a process which unfortunately ended with the Medici. Only the realization of the railway in 1848 allowed the Valdelsa to stand back up and nowadays it attracts tourists from all over the world, eager to discover the beauties Tuscany has to offer.

If you want to rent a farmhouse or a villa in Valdelsa, Agenzia Romolini Immobiliare – Christie’s International Real Estate offers farmhouses and luxury villas for rent both in the Valdelsa Senese and Fiorentina.



In the area known as Valdelsa Senese, or Upper Valdelsa, are located the municipalities of Casole d’Elsa, Colle Val d’Elsa, Monteriggioni, Poggibonsi, Radicondoli and San Gimignano.

The small hamlet of Casole d’Elsa, with a typically medieval urban asset, is built on a rocky spur which allows it to dominate the underlying valley. Originally founded by the Etruscans (as testified by several tombs found in the area), the hamlet hosts several points of interest worth visiting such as the Chiesa della Collegiata di Santa Maria Assunta and the annexed cloister, the Cappella degli Aringhieri with frescos by the school of Duccio da Buoninsegna, the Palazzo Pretorio and the Palazzo Comunale but most of all the archaeological museum, full of paintings from the Sienese and Florentine area.

Etruscan and Roman findings have been unearthed in the area of Colle Val d’Elsa, a medieval town born after the union of three preexisting hamlets (Borgo Santa Caterina, Castello di Piticciano and Piano). Knows as Colle Alto, the hilly area hosting the historic centre and the castle is the most ancient. Here one can see the Cattedrale dei Santi Alberto e Marziale, the Palazzo Pretorio, the Chiesa di Santa Maria in Canonica, the towerhouse of Arnolfo di Cambio and the Chiesa di Santa Caterina. Colle basso is the most recent part of the town and hosts the modern city.

Mentioned by Dante in its Divina Commedia with the verses “on its circular parapets / Montereggione crowns itself with towers”, Monteriggioni is a dive into the past thanks to its nice walls and the perfectly preserved towers defending the hamlet. Built by Siena at the beginning of the 13th century as a defense against Florentine raids, Monteriggioni is located right at the border between Valdelsa and Chianti. Through the main gate one can reach the central square with the Chiesa di Santa Maria Assunta.

Next to the hills of Chianti, Poggibonsi is a hamlet born around the old Pieve di Santa Maria, whose only remains today are the foundations of the bell tower. Contended for century between Florence and Siena, Poggibonsi is nowadays an important commercial and industrial town, widely known for wood crafting.

In panoramic position, Radicondoli is known for its hydrothermal plants and the Natural Reseve of Cornate and Fosini. Important places of interest are the Collegiata dei Santi Simone e Giuda, with its impressive bell tower, the Pieve Vecchia della Madonna and the Convento di San Francesco dell’Osservanza.

Included in the list of the UNESCO World Heritage Sites, San Gimignano dominates the Valdelsa with its beautiful towers. Widely known for its Vernaccia, an excellent white wine, San Gimignano is also an important producer of saffron.



The municipalities included in the Florentine Valdelsa’s territory are Castelfiorentino, Certaldo, Gambassi Terme, Montaione e Montespertoli, where Agenzia Romolini Immobiliare offers prestigious villas and farmhouses for rent, an ideal choice for those dreaming of a vacation in the Tuscan countryside.

The original core of Castelfiorentino, named Timignano, was initially a Roman settlement located in a strategic location between the Via Francigena and the Via Volterrana, next to the river Elsa. The name Castelfiorentino was only used for the castle built on the hill above the town. Inside the hamlet are located several churches, among which the Pieve di Sant’Ippolito and the Santuario di Santa Verdiana. Frescoes and sinopias by Benozzo Gozzoli are exhibited in the BEGO-Museum.

Home town of Giovanni Boccaccio, known for his Decameron, Certaldo is a beautiful hamlet built atop of a hill whose name can be traced to the Latin Cerrus Altus, which indicated a hill covered in Turkey oaks. The higher section of the town is the oldest one, where the castle is located, while the modern one is located in the lowlands. Unlike many medieval towns, Certaldo is not laid out around a central square but around an Avenue, called Via Boccaccio, where one can find the main church, the Palazzo Pretorio and the Palazzo Stiozzi-Ridolfi (le Logge del Mercato).

Once district of Montaione, Gambassi became formally independent in 1917 and gained in 1977 the follow-up name of Terme following the foundation of thermal plants. The castle, whose first appearance can be dated to 1037 AD, was partially gifted to the Bishop of Volterra Goddifredo. It took several years before it was totally acquired by the church, which kept possession of it until the 12th century. Next to the castle was built a palace which would eventually become the town hall.

Founded according to the legends by Ajone, a young Volterra citizen who saved the beautiful Figline da Gambasso, Montaione is a fortified hamlet protected by towers. Historically rich, the town hosts several palaces and churched from the early Middle Ages, such as the Pieve di San Regolo overlooking the main square. Around Montaione are located numerous castles, among which the castle of Figline, Collegalli and Vignale.

Located just 20 km from Florence, Montespertoli is dotted by palaces, churches and castles. The oldest documents about the town dates back to the 12th century. Just around the hamlet are located the castles of Bottinaccio e Poppiano, owned by the famous Guicciardini family.



Findings dating back to the Etruscan age allow us to determine an intensely human activity in the region starting from the 6th-century b.C. in the form of scattered settlements and agricultural estates, a model undertaken and carried out by Romans too.

During the Middle Ages the construction of the Via Francigena, which permitted an easy route between northern Europe and Rome, gave a determinant impulse for the urbanization of the region. Churches, watchtowers, castles and even fortified hamlets (San Gimignano and Borgo San Genesio) were built along the road.

At the same time, Valdelsa became an important strategic and military hub: Florence showed a growing interest in the region, with a not really enthusiastic reaction on part of the local families, unwilling to give up their possessions. Construction of fortresses and castles such as Certaldo, San Miniato, Castelfiorentino and Semifonte was an attempt to keep control of the area.

Between the 13th and 14th century, Florence’s dominion reached the river Elsa and with the conquest of Castelfiorentino and Certaldo the city finally won the access to the Via Francigena. The track was moved to the valley floor and the opposite bank of the river, promoting the flowering of lowland towns (Castelfiorentino, Certaldo, Poggibonsi…) to the detriment of those along the old road (Coiano, Gambassi Terme, San Gimignano…). The Republic of Siena kept Monteriggioni as its only fortress in the region.

Florence managed to occupy the whole region during the 15th century with the siege of San Gimignano and Poggibonsi, included in the Vicariato di Certaldo (established in 1415).

Used as an “agricultural exploitation area”, the Valdelsa lived a period of economic and cultural regression under the Medici. Winds of changes only started to blow with the reign of the Lorena family (after 1737) and the real impulse was given by the central Tuscan railroad built in 1848 which fostered the establishment of numerous industrial sites in the region.

VAL D’ELSA Wine Estates, Farmhouses with vineyards, Luxury Villas for sale in Elsa Valley (Valdelsa), Florence Siena

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