Neoclassical Villa in Pistoia, Tuscany, Italy, approx. $20,040,292. View Listing
Diletta Giorgolo
Diletta Giorgolo
Head of sales, Central and Southern Italy at Italy Sotheby’s International Realty

Overseas buyers are increasingly eyeing Tuscany, world-famous for its historic mansions, wine estates and elegant villas. Home to Florence and Siena, Lucca and Pisa, a long stretch of the Mediterranean coast and stunning landscapes featuring hills and woods and a wonderful climate – in fact, Tuscany has plenty of charm to tempt even the most demanding jet setters.

But even Tuscany, of course, can feel different depending on the location you live in. So, we asked Diletta Giorgolo from Italy Sotheby’s International Realty to recommend the best places to settle down in this picturesque region.

Tuscany in numbers:

  • More than 2000 restaurants from the Michelin guide including 10 three-star, 39 two-star, 316 one-star restaurants.
  • 2493 scenic walking routes (travel aggregators data).
  • More than 1000 agriturismi (farm-holiday houses for tourists).
  • 53 highest quality wines: 42 DOC and 11 DOCG wines produced in Tuscany.
  • 30 landmarks including 23 historic villas and 7 UNESCO World Heritage Sites.
  • 10 provinces: Florence, Arezzo, Grosseto, Livorno, Lucca, Massa Carrara, Pisa, Pistoia, Prato, and Siena.

Siena, Province of Siena


Medieval house close to Siena, approx. $15,914,350, for sale by Italy Sotheby’s International Realty. View Listing

Sienna is one of Tuscany’s oldest Medieval cities, dating back to the Etruscan era, and the capital of the province of Siena located between the Chianti region and Montalcino. Living in Sienna is one of the most authentic ways to experience the Tuscan lifestyle. Imagine having an early morning espresso in the magnificent Piazza Del Campo, followed by a visit to the Duomo of Siena and rounding up your day with the traditional meals of Siena – the ‘pici’, a type of pasta with pepper and cheese or tomato sauce and typical almond cookies, ricciarelli.

Lucca, Province of Lucca

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Villa with swimming pool in the countryside of Lucca, approx. $4,089,931, for sale by Italy Sotheby’s International Realty. View Listing

Buyers are increasingly looking towards more authentic and less touristy locations that offer more options than the well-established second home markets. One of the examples is the wonderful city of Lucca famous for its unique well-preserved Renaissance walls encircling the city center, numerous palazzo and outstanding camellia gardens. And the Lucca countryside offers some of the most beautiful Medieval and Renaissance villas in Italy.

Montepulciano, Province of Siena


Wine estate with spectacular views of Montepulciano, approx. $11,788,407, for sale by Italy Sotheby’s International Realty. View Listing

Montepulciano, a medieval village set on top of a hill, is best known for its Vino Nobile, considered one of the top Tuscan wines in the world, made with grapes coming from vineyards surrounding the village. The area is picture-perfect, with cypress trees growing alongside rustic country lanes.

Cortona, Province of Arezzo


Historical palazzo in Cortona, approx. $3,524,733, for sale by Italy Sotheby’s International Realty. View Listing

This typically Tuscan town makes a perfect base for making forays into the countryside should you wish to find a villa to restore. The surrounding valleys dotted with olive groves are visible from Cortona as the historic city, enclosed by stone walls dating back to Etruscan and Roman times, sits on the top of a hill about 1968 feet (600 meters) above sea level.

Val D’Orcia, Province of Siena

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Equestrian Estate, approx.$9,989,775, for sale by Italy Sotheby’s International Realty. View Listing

Named after a river, the valley is quintessential Tuscany, and it has the badge of the UNESCO World Heritage Site to show for it. Oak forests, olive groves and vineyards that produce Brunello and other fine Tuscan wines cover the hillsides. Villages and monuments with loads of character and charm make for interesting excursions. Monte Amiata, Italy’s oldest extinct volcano, is another fascinating landmark.

Monte Argentario, Province of Grosseto


Villa with Seafront Pool, approx. $4,479,594, for sale by Italy Sotheby’s International Realty. View Listing

Monte Argentario, a municipality in Southern Tuscany, has its main centres in Porto Santo Stefano and Porto Ercole. Today, Porto Santo Stefano is not only known for its 17th century fortress and two Spanish lookout towers. It’s a lively port full of fishing boats and fish that comes from the Tyrrhenian Sea and sold fresh by the harbor. Interestingly, one of Italy’s most famous painters, Michelangelo Merisi, known as Caravaggio, exiled by the Pope, died in Porto Ercole of a fever on 18 July 1610. From the peninsula you can have easy access to the islands of the Tuscan Archipelago – Giglio, Giannutri and Montecristo and all the boating and sunbathing you can handle.

Florence, Province of Florence


Villa with pool on the Pian Dei Giullari hill, Florence, P.O.R. View Listing

In Florence, the region’s capital also known as the “cradle of Renaissance”, buyers are interested in historical landmark properties. I personally recommend to simply get lost in the historical city center of Florence: take a stroll by the stunning renaissance Palazzo Gondi in Piazza San Firenze, Palazzo Vecchio and the Uffizi Museum, have an Italian espresso in a historical cafe in Piazza della Signoria. Near Ponte Vecchio, stop and make a wish at the famous porcellino fountain under the medieval lodges. On crossing the bridge you’ll arrive in the Oltrarno area, where you can visit the magnificent Palazzo Pitti, an ideal spot for clubbing and shopping.

Real estate market in Tuscany

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Villa overlooking the sea in Porto Ercole, P.O.R. View Listing

  • In Tuscany, overseas buyers tend to be from financiers or international bankers and top managers and entrepreneurs. These savvy internationals own multiple homeowners in various countries and travel a lot.
  • Another category are couples, aged 50-60, looking for second homes, while singles and younger couples are eyeing properties in Florence.
  • Retirees mostly seek trophy asset villas and vacation homes in Tuscany, whilst many make their Florence property their main residence because of a flat property tax.
  • Serial investors and investment funds are mainly interested in commercial and hospitality real estate in Florence as well as castles and villas with top views and wine estates.
  • According to Sotheby’s International Realty, top countryside villas cost from 4 million euros, or 3,000-5,000 Euro/sq,m.
  • Even if your wallet doesn’t stretch that far, villas in less famous locations are on offer from 1,500 Euro/sq.m. Perhaps there are profits to be made as rural tourism is gathering momentum.
  • Real estate taxation in Italy is very favorable compared to many other EU countries.

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