There’s something about a Tuscan hill town that stirs the soul.
Maybe it’s the golden light, the scent of cypress and wild herbs, or the views rolling out toward the horizon in waves of vineyards and olive groves.
Life moves differently in this fabled region of Italy. Slower. Richer. More rooted.
This week, I’ve pulled together three Italian escapes that recently featured on the Your Overseas Dream Home Instagram account.
They capture the essence of that timeless Tuscan lifestyle.
The hills of Tuscany are dotted with beautifully dreamlike hill towns where you can live the rural Italian dream, rooted in a sense of history and tradition.
They’re all perched high above the valleys, in medieval towns where the architecture is centuries old and the food tastes like it’s been perfected over generations.
These are real, character-filled homes in Massa Marittima, Montepulciano, and Roccastrada.
Each one offers something rare: a foothold in Tuscany…and for pricing that can be surprisingly affordable.
Roccastrada: A Bijou Hideaway
Listing price: €55,000 ($64,800)
Perched 1,500 feet above Tuscany’s Maremma region on a volcanic ridge, Roccastrada enjoys panoramic views sweeping from rolling vineyards to distant coastlines.
The surrounding oak and chestnut forests contain natural springs within the Metalliferous Hills Park, a protected area preserving the region’s mining heritage.
The Monteregio wine trail winds through town, pairing local tastings with traditional wild boar and hare ragù. Historic Siena lies 19 miles northeast, the Mediterranean coast 19 miles southwest.
The stunning sight of sunset over the mountains in Roccastrada.
Set within this remarkable landscape, this charming, renovated apartment sits in the historic center on a narrow street facing the church of Santa Maria delle Grazie.
The bijou apartment has a living room with kitchenette, a double bedroom, and a bathroom with shower, plus views over the medieval fortress.
This property is on the market for €55,000 ($64,800). Check out the full listing here.
This bijou apartment in Roccastrada opens out onto rustic hillside lanes.
Massa Marittima: A Restored Gem in a Medieval Hilltop Town
Listing price: €230,000 ($271,100)
This bright first-floor apartment sits within a 12th-century building in Massa Marittima’s historic center, where cobblestone streets spiral around the magnificent Cathedral of San Cerbone. Perched on a hilltop at 1,247 feet above sea level, this Tuscan gem sits where Etruscan settlements once flourished and silver mines created centuries of prosperity.
This is the medieval old town of Massa Marittima in Tuscany.
The property has been sensitively restored, preserving original features like exposed wooden beams, terracotta floors, and brick arches. The apartment has a living room, an open-plan kitchen, a laundry room, a reading room, a bathroom, and two double bedrooms.
The region enjoys a Mediterranean climate with warm, dry summers and mild winters. July and August offer endless sunshine hours and virtually no rainfall, while spring and autumn transform the rolling countryside with rich seasonal colors.
Just 11 miles away lies the coastal town of Follonica, where sea breezes drift inland to soften even the warmest summer day.
This property is on the market for €230,000 ($271,100). Read the full listing here.
This Massa Marittima apartment has one bathroom and two double bedrooms.
Montepulciano: Renaissance Living in a Palazzo Apartment
Listing price: €260,000 ($306,600)
Perched majestically on a limestone ridge nearly 2,000 feet above sea level, Montepulciano commands breathtaking views across southern Tuscany’s rolling valleys. This Renaissance town nestles within gentle hills and golden fields that define the classic Tuscan landscape, rising dramatically from vineyards that produce Vino Nobile di Montepulciano, one of Tuscany’s principal red wines.
The town sits 48 miles southeast of Siena, the UNESCO medieval masterpiece famous for its shell-shaped Piazza del Campo, and 77 miles southeast of Florence, birthplace of the Renaissance and home to Michelangelo’s David.
Aerial view of Montepulciano, a medieval and Renaissance hill town in the Italian province of Siena in southern Tuscany, Italy.
This charming two-bedroom apartment sits in a 14th-century palazzo at Montepulciano’s historic heart, just steps from shops and restaurants.
Spanning 1,001 square feet across two floors, the thoughtfully renovated property features a living area with kitchenette, guest bathroom, and storage on the first level, while upstairs two bedrooms offer sweeping views over Tuscan rooftops and countryside.
This property is on the market for €260,000 ($306,600). You’ll find all the details here.
This apartment is in the heart of the historic center of Montepulciano.
Wishing you good real estate investing,
P.S. If you’re interested in any of these listings you should hire an attorney and do your own due diligence. We haven’t done any due diligence on them.
P.P.S. For more listings of affordable overseas dream homes, click here to follow our Your Overseas Dream Home Instagram account.
