The best places to live in Tuscany are certainly subjective to your preferences for markets, wine, food, and great landscapes. If you are on a small budget then real estate in Tuscany like Valdarno villas or Garfagnana apartments might be more your style. Chianti is going to be highly expensive; however, it is most convenient for travel throughout the Tuscan region.
Chianti has exploded in popularity in recent years due to the famous Chianti wines. This region of Tuscany is highly famous for its red wine, food and natural ambience. Living in this region can be expensive as most real estate is either a winery or in the city; however, you are also near plenty of wineries for tasting and tours. The Chianti Region includes the cities of Florence, Siena, Reggello, Greve, Val di Pesa, Tavarnelle Val di Pesa, Radda, Castellina; Gaiole, Panzano, Montemarciano, and Castelnuovo Berardenga.
Many of the interesting areas in Chianti are in Florence or Siena especially for museums, galleries, schools, and markets; however, the countryside offers a beauty that is unmatched. Affordable and less touristy locations in Tuscany to live include Valdarno which is just one of the more inexpensive places to live in Tuscany, with fewer tourists and a more natural landscape than the cities offer. Valdarno is in the valley of the Arno River with several towns that you could live in or near like Rignano sull'Arno or Incisa Valdarno. The Valdarno area is easily reached from florence (30 minutes) and Rome (under 2 hours ) by train and highway.
Casentino is another valley that lies along the river, known for its beautiful landscapes and mountains like Mount Falterona. It is the northern boundary to Casentino and Romagna with the Alp of Serra and Alp of Catenaia. It is known for its forests as well as its larger communes: Bibbiena and Poppi. Saint Francis lived the later part of his life in this area.
The Empoli area is south of Florence by 12 miles offering you history, museums, and archaeological finds of importance. Here you can live and learn about the Roman Empire, enjoy the main railway line and travel throughout Tuscany with relative ease. One of the main sights is Piazza Farinata degli Uberti, a fountain created by Luigi Pampaloni. Several notable people called Empoli their home and now you could too.
The area of Pisa is another place to consider. It has a very small population making it an amazing community with beautiful sights you may enjoy.
The secluded Garfagnana is the cheapest of the locations mentioned here where you could live and enjoy Italy. It is also the most secluded with mountains, the Apennines surrounding you, a small lake, and the river Serchio. Historically it is of significance to the Roman Empire and then the Duchy of Modena. It is the most verdant due to heavy rainfall.