Say Tuscany, and most people will think of cypress-covered hilltops with a sprinkling of olive groves. But Italy’s fifth largest region has nearly as many landscapes as it has contrade (neighbourhoods). Some 100 miles will take you from snowy mountains to soft golden beaches, from the art cities’ urban wonderland to valleys where pine is more common than cypress. Each area has its own architecture and building styles, which don’t always match the stereotypical view of a Tuscan farmhouse.

This diversity of landscapes and housing can confuse buyers looking for a second home in the land of Leonardo. But it can also work to their advantage, because, with a modicum of research, it nearly always allows people to find the perfect setting to suit their preferences. ‘We always tell people to decide which part of Tuscany they like best before they start looking for a property, because the areas are so different,’ say Rupert Fawcett and Bill Thomson of Knight Frank. ‘It’s better to look at the area first, then the house.’

Tuscany’s many countrysides

When faced with a choice of landscapes, most buyers are likely to say they want to purchase a house in the Tuscan countryside. But rural districts such as Chianti, Val D’Orcia or Val Di Chiana, although equally verdant, look and feel very different. The Tuscan countryside par excellence is Chianti, a historic district linking Florence to Siena and, eastwards, to the Valdarno. Traditionally, this was a favourite destination among international second-home owners and, after a couple of quiet years it has seen a marked return in interest. This is partly because buyers are fleeing market uncertainty, preferring tried and trusted destinations, and partly because Chianti prices experienced a 10%-20% dip over the past two years. With average values now ranging between €3,000 and €5,000-€6,000 per square metre, according to Valerie Bottazzi of Tuscany Real Estate, Chianti is once again competing with other top destinations.

The area is as appealing as ever, with steep hills covered by thick woodland, vineyards and olive groves. ‘In Chianti, particularly in Chianti Classico, the heart of the district, you find three landscapes-woods of ilex, oaks and chestnut, vineyards and olive groves,’ says Miss Bottazzi. Despite its undulation, however, ‘Chianti is a bit closed,’ say Mr Thomson and Mr Fawcett. ‘Because of the woodland, you don’t really get very long views.’ If topography dictates the panorama, geology shapes the local architecture. In rock-peppered Chianti, casolari and farmhouses are usually built in the local Albarese stone, which, explain Mr Fawcett and Mr Thomson, ‘when cut, is greyish blue’. Broken up by external shutters and topped with terracotta tiled roofs, the cool-hued stone gives houses a strong rustic flavour, which is especially popular with international buyers. Travel southwards past Siena, and the Albarese grey gives way first to Le Crete’s warm red bricks, then to the rose and yellow stones of Val d’Orcia. Home to some of Italy’s most famous wines, including Brunello di Montalcino and Vino Nobile di Montepulciano, Val d’Orcia is the archetypal Sienese landscape, where ancient casolari overlook lush farmed fields and tidy rows of vines.

‘The Val D’Orcia landscape is truly amazing, with magnificent depths, because there are soft hills of different heights that make for ample views,’ says Eugenio Greco of Hamptons Italy. Only a handful of miles separate Val d’Orcia from Chianti, and house prices are nearly on a par, but the landscape is so fundamentally different that ‘people are for either one of the other,’ explain Mr Fawcett and Mr Thomson. ‘They will either love Val D’Orcia, or they will love Chianti.’

That said, both places are highly sought after and it is becoming difficult to find rustici to restore from scratch. Instead, there is a good selection of period villas and farmhouses that may at most need a touch-up. Also available are managed homes in converted borghi, which are increasingly popular thanks to their ease of maintenance.

Further east, the municipality of Cortona has hills that rise high above the flat Val di Chiana, giving superb views. ‘From the hills of Cortona, you can see 60 miles to Montpulciano, Lake Trasimeno and the countryside towards Arezzo,’ says Roger Coombes of Cluttons Italy. The terrain is so steep that, in the town of Cortona itself, there is only one flat road, the Via Nazionale (also known as Ruga Piana, or ‘Flat Street’). Medieval Cortona has narrow, sloping alleys lined with exposed stone or plastered town houses. In the surrounding countryside, buildings are predominantly made of local stone, which has an attractive grey hue.

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A good number of these stone farmhouses come up for sale at any given time, and you can still find the odd rustico to restore, although ‘there aren’t so many left,’ according to Mr Coombes. Borghi apartments and village houses can also be found, both in the Val di Chiana and, more rarely, on the hillsides. Cortona prices depend on location and condition, but usually remain in the region of €3,000 to €4,000 per square metre, reaching the €5,000s for the most sought-after properties. This is up to €1,000 per square metre less than the 2008 peak value.

Tuscany by sea – Forte dei Marmi

If Chianti and Cortona have seen a reduction in value, albeit modest, prices show little sign of dipping in Tuscany’s most fashionable seaside resorts, which are among the most expensive in Italy.. The Tuscan coastline is just under 400 miles long, with 250 on the mainland and the rest on the islands of the Tuscan archipelago. Some stretches have jagged cliffs, but most of the shoreline is taken up by long expanses of golden sand.

The quintessential beach resort of this kind is Forte dei Marmi, in the Versilia district. The village became popular with Italian aristocrats in the early 20th century, says Beatrice Sidoli of Winkworth Italy, and, later, with entrepreneurs from the north of the country. In their wake came private lidos with bars and restaurants, luxury shops that give London’s Knightsbridge a run for its money, and a lively club scene. ‘For the Italians, Forte dei Marmi has been a destination of choice for decades,’ says Miss Sidoli. ‘There are families that have known one another for generations and meet every summer at the beach clubs.’ The resort’s relatively recent history means that houses mostly date from the 1960s to the 1980s, and may sometimes need renovation. Yet Forte’s housing prices are solidly in the region of €20,000 per square metre.

The art cities – Florence, Siena and Luca

Only properties in Tuscany’s art cities can command similar values to those of Forte, and particularly so Florence, which attracts both local and international demand. Historically the capital of Tuscany, Florence has the grandest feel (and the grandest prices). ‘As well as monuments such as the Duomo or the Battistero, it has plenty of aristocratic palazzi,’ says Mr Greco. ‘They have an opulence rarely seen elsewhere in Tuscany.’ The most lavish properties are set on the northern Lungarni, the roads that flank the River Arno. ‘Here, you can find apartments in palazzi that have 16ft-23ft-high coffered ceilings and huge windows with views over the Arno or the Fiesole hill,’ says Mr Greco. Alas, prices match this magnificence, reaching up to €14,500 per square metre.

Although it was nearly as powerful and rich as Florence, Siena has a more sober look.‘It is a typical medieval city, perched up on a hill dominating a valley,’ says Mr Greco. ‘The streets are smaller and narrower than in Florence, and, although the types of properties available are similar-usually, apartments in converted palazzi-their architectural style, Gothic, is far more austere.’

Values are, however, far from austere, ranging from about €4,000 to about €9,000 per square metre for city-centre properties. Lucca is positively cheap by comparison, with city-centre apartments fetching in the region of €3,600 to €4,400 per square metre.

Once Italy’s second largest city-state, and one of the richest, Lucca has an individual character that reflects its long history. The city centre is a rare blend of medieval, Renaissance, Baroque and neo-Classical architecture, and this varied heritage appeals to sophisticated buyers looking for art, culture, food and wine slightly off the beaten track.

Most of the properties for sale in the walled city are in period buildings dating at the latest from the early 20th century. ‘Some are very prestigious and expensive, others are more affordable and romantic,’ says Miss Sidoli. What makes Lucca unique, however, are the Baroque villas in the hills around the city. Most of these houses were built by prominent families in the 17th and 18th centuries and are in ornate Baroque style- an unusual sight in Tuscany, where the clean shapes of medieval architecture and the Classical forms of the Renaissance predominate.

The rarity, historic importance and grandeur of these villas makes them the objects of a highly confidential market with dizzying prices, often €10 million-€20 million.

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** This article features in COUNTRY LIFE INTERNATIONAL, out on March 2 with COUNTRY LIFE magazine