What if your next home came wrapped in centuries of history?
In Italy, the past isn’t locked behind museum doors. It lingers in the places people still call home.
Some of the most captivating residences today are tucked within former convents, countryside mills, and long-silent cloisters—buildings that have been reimagined—with respect and care—into elegant homes, ready for modern living without losing their soul.
Each one whispers a different story—and invites you to be part of its next chapter.
And right now, you can own one for less than you might expect.
We’ve uncovered three unique dream homes on the market in Italy now, from the Tuscan hills to a Piedmont village in northern Italy.
Renaissance Mill Retreat Near Cortona for $235,100
Perched high above the Val di Chiana, Cortona is one of Tuscany’s oldest hill towns—founded by the Etruscans over 2,500 years ago. Its medieval walls still encircle steep cobbled lanes, honey-hued stone houses, and a vibrant piazza where time seems to idle.
Cortona found modern fame in the 2003 movie Under the Tuscan Sun, starring Diane Lane, but long before that, Cortona was a center of Renaissance learning, art, and philosophy.
Today, it draws artists, scholars, and dreamers alike.
The Santa Maria delle Grazie al Calcinaio church in Cortona enjoys panoramic views of the scenic countryside that surrounds it.
Just 1.9 miles from Cortona, this one-bed apartment spanning over 807 square fee t occupies part of a former mill complex.
Inside, you’ll find traditional Tuscan features—terracotta tiles, a rustic fireplace, and wooden beams—blended with modern comforts. There’s a shared pool, landscaped gardens, and glorious views of Cortona rising in the distance.
This is the kind of place that invites a slower rhythm: morning swims, market-fresh lunches in the courtyard, and evenings spent under a canopy of stars.
This property is on the market for €200,000 ($235,100) Read more here.
This one-bed apartment in a former mill complex is a charming rural oasis.
Apartment in a Former Convent near Castiglion Fiorentino From $111,700
Often overshadowed by nearby Cortona and Arezzo, Castiglion Fiorentino is a hidden jewel of southern Tuscany. Its name—“Little Castle of the Florentines”—hints at its past as a strategic medieval outpost between warring city-states.
The hilltop town still brims with old-world charm: Romanesque churches, Renaissance palazzi, and sweeping views of the Val di Chio.
Every summer, a jousting tournament fills the streets with costumed parades and medieval fanfare.
The historic town of Castiglion Fiorentino got its current name when Florence took control of it in 1384.
This recently transformed convent and adjoining farmhouse now house 17 apartments—each carefully restored with original details like exposed beams, vaulted ceilings, and terracotta floors.
Set amid the sunflower fields – just outside Castiglion Fiorentino, this is true Tuscan countryside—authentic, untouched, and within easy reach of Florence and Rome by train.
You can get a charming studio here for just €95,000 ($111,700). Read the full listing here.
There are 17 apartments for sale in this newly renovated convent and farmhouse near Castiglion Fiorentino.
Baroque Elegance in Piedmont For $327,900
Nestled among rolling vineyards and chestnut woods, Marentino is a quiet Piedmontese village less than 30 minutes from Turin.
This region was once the domain of the powerful House of Savoy, whose influence gave rise to a Baroque architectural style marked by ornate churches and stately villas.
From vineyard-cloaked slopes to alpine peaks, the Piedmont region’s layered landscape stuns in every direction. It earns its name, meaning “at the foot of the mountains”.
In the green hills east of Turin, within a beautiful estate from the 1700s, you’ll find this extraordinary first-floor apartment.
At over 1,600 square feet, it’s a romantic blend of old and new: a coffered wood ceiling here, a carved stone fireplace there, plus sleek finishes and modern conveniences throughout.
French doors open onto a small private garden, while the wider grounds—over seven acres—include manicured lawns and walking paths shaded by ancient trees.
It’s a place of inspiration and beauty—ideal for writers, artists, or anyone seeking a soulful escape with grand flair.
This property is on the market for €279,000 ($327,900). You can find all the details here.
This stunning apartment is located in the “Maiolo Castle”, a former convent that dates from the 1700s.
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.
