Podere Gregorio 18 to 22
14th Century Three-House Chianti Estate for 22 with Pool and Cypress Avenue : South of Florence
Perfect for
- Large groups (18-22) who want to be together but not on top of each other - three separate houses, each with its own kitchen, means families or couples can have genuine privacy while sharing the pool and courtyard.
- Weddings, milestone birthdays and family reunions - the estate can be booked for a minimum of three nights for celebrations; the candlelit courtyard between Torre and Fienile is exceptional for evening dining
- History and culture enthusiasts - the estate dates to the 14th century and was once home to Marsilio Ficino, the Renaissance humanist who founded Florence's Platonic Academy and gave Medici-era Florence much of its intellectual identity
- Chianti wine lovers positioned for estate visits and tastings, with sommelier-led sessions available on-site
- Fashion and outlet shoppers - The Mall (Gucci, Prada, Bottega Veneta) is 15 minutes away
Good to know
- Weddings and large events are welcome with a 3-night minimum - ask us about this separately, as different arrangements apply
- The three houses share the pool and grounds but are otherwise self-contained, each with its own kitchen - check with us which configuration suits your group
- Pool is unfenced (1.4-2.4m deep)
- Central heating is charged extra at €100 per night
Podere Gregorio - known locally as Podere la Specola - is a 14th century Tuscan estate on a rare piece of flat land at the edge of the Chianti hills, approached through a cypress-lined avenue into an olive grove. The estate was once home to Marsilio Ficino, the Renaissance humanist who founded Florence's Platonic Academy and gave the Medici court much of its intellectual character. Something of that history lingers in the stone walls and the quiet.
The estate comprises three separate buildings - La Torre, Il Fienile, and Villa al Prato - set around a shared courtyard that comes alive at dusk when lights are strung between the ancient watchtower and the farmhouse. Each building has its own kitchen and living space, which means that a group of 22 can gather together or retreat into smaller groupings without anyone feeling crowded. A 16 x 8m pool with hydromassage tub sits in the grounds, surrounded by sun terraces and the silvery olive grove.
La Torre is the oldest structure, a fortified watchtower built to protect the Arno valley, with walls thick enough to keep it cool in summer. Il Fienile, the farmhouse, has its own wood-fired oven and opens directly toward the pool through a shaded loggia. Villa al Prato is the smallest of the three - a cottage for four tucked beyond the pool with its own terrace looking out over the olives. At dusk, the courtyard between La Torre and Il Fienile,adorned with lemon trees, comes alive with twinkling lights - ideal for a leisurely dinner or intimate gathering with friends and family .
Bespoke additions can be arranged: cooking classes, sommelier-led wine tastings, guided cycling through the Chianti hills, and massage. The Mall outlets (Gucci, Prada, Bottega Veneta) are 15 minutes away. Florence is 30 minutes. The estate is also available for weddings and celebrations with a three-night minimum - ask us for details.
With private parking, meticulous cleaning, and attentive hosts nearby (ensuring privacy but ready to assist), Podere Gregorio presents a seamless blend of rustic charm and refined luxury.
Podere Gregorio is listed under the following categories:
Accommodation
Inside La Torre
La Torre at Podere Gregorio is impressively old, built of stone, with thick walls that keep the heat out in summer and hold warmth in the colder months. You enter into a wide hallway with a cool terracotta floor and plain white walls. There is a sense of quiet. On your left an enormous and ancient family tree charts the owners' antecedent, to the right a stone staircase leads upstairs. The air smells faintly of dust, dry wood, and something herbal—maybe bay or fennel from the garden.
Ahead, large wood-beamed rooms are spacious living areas with comfortable sofas set up against the thousand year old stone walls, a few armchairs gathered around the fireplace. Light filters in through shuttered windows. There are shelves of books in various languages, a few board games, and a worn rug on the floor. On one side of the ground floor the kitchen is large and functional, with a long wooden table in the middle. The cupboards are painted in a pale colour, and there’s a wood-fired stove that still works, though most people use the gas range. It’s the kind of room where people tend to linger, even after the meal is finished.
Upstairs, the bedrooms are unadorned. Whitewashed walls, tiled floors, iron beds with good mattresses, old wardrobes. Linen curtains shift in the breeze. You hear birds in the morning, sometimes a tractor in the distance. The bathrooms are spacious, with strong showers and plenty of hot water.
Everything in the house has been chosen with care, and it is a house made for living in: there’s no pretence - just space, light, and a feeling of calm.
Il Fienile
Like La Torre, Il Fienile is spacious and well-equipped. The living areas have the same beautiful square terracotta tiles as the tower entrance, contrasting beautifully with the whitewashed walls and ceilings. The kitchen (each villa has its own kitchen) is spacious, centered around a long dining table. The kitchen opens out towards the pool, with a shaded loggia. The dining room opens on the other side of the house, onto the courtyard space between the Tower and the Fienile.
Upstairs the bedrooms have wooden beamed ceilings, windows with wonderful views over olive groves and the Chianti hills.
Villa al Prato
This Villa has the grandest name but is the smallest of the three buildings, a sweet little cottage for four set away from the other two, just beyond the pool and in the olive grove. It has a kitchen and living room, a bedroom downstairs, one upstairs and a wonderful little terrace that looks out over the olives and the pool.
Features
Villa Details
- Air Conditioning
- Swimming Pool
- All ensuite
- Wifi
- Free Parking
- Central Heating
- Private Pool
- Fireplace
- Insect Screens
- Jacuzzi
- Pets Welcome
- Barbecue
- EV Charging
Bedrooms and Bathrooms
- In The Tower: 3 Doubles And One Twin (Can Be Converted To A Double)
- In The Tower: 4 Bathrooms Upstairs Plus A Service Wc On The Ground Floor
- In Fienile: 3 Doubles, One Of Them A French Double
- In Fienile: 3 Ensuite Bathrooms Upstairs, A Further Bathroom On The Ground Floor
- In The Villa: A Twin Bedroom On The Ground Floor, A Double On The First Floor, Both With Bathrooms
Kitchen equipment
- In The Tower: Old Stove, Fully Equipped Kitchen, Fridge/Freezer, Oven With 5 Gas Hobs, Large Ancient Stone Sink, Long Table With Wooden Benches, French Door To Furnished Terrace.
- In Fienile: Fully Equipped Kitchen, Fridge/ Freezer, Oven With Gas Hobs, Wood-Fired Oven, French Doors To A Pergola Looking Over The Pool
- In The Villa: Fully Equipped Kitchen, Fridge, Oven With Gas Hob, Fireplace.
- Dishwashers
Amenities
- Washing Machine In Each House
- Tvs
- Libraries
- Snooker Table
- Air Conditioning In All Bedrooms
- Insect Screens
- Iron And Ironing Board
- Ev Charge Point
What's included
- Air Conditioning
- Tourist Tax
Extras
- Central Heating €100 Per Night
- Pets Welcome (€105/Stay)
Outdoors
- Private Pool, 8X16 M, 1.4 To 2.4 Mdeep, Not Fenced
- Jacuzzi
Nearby Activities
Photos
Reviews
Where is Podere Gregorio ?
Getting here
- Florence FLR Airport 50 mins
- Pisa Airport (PSA) 1 hr 30 mins
- Rome Airport (FCO) 3 hrs
Around Podere Gregorio
The estate sits at the foot of the Chianti hills just above the Arno valley, in what's called the Valdarno - the valley of the Arno river south of Florence. It's well-placed: close enough to Florence for day trips, with Chianti wine country on the doorstep and Siena an hour to the south.
Figline Valdarno (15 mins): The nearest town of any size, with supermarkets, restaurants, and a train station. Direct trains to Florence Santa Maria Novella take around 35-40 minutes - useful if some of your group wants to visit Florence without everyone piling into cars.
The Mall Outlets (15 mins): One of Italy's best luxury outlet centres, with Gucci, Prada, Bottega Veneta, Burberry, Saint Laurent, and others at significant reductions. Worth knowing about even if it's not your primary reason for coming.
Chianti Wine Country (20-30 mins): The classic Chianti Classico zone begins almost immediately to the west. Greve in Chianti is around 25 minutes - good market town with an enoteca on the piazza where you can taste and buy from dozens of estates. Greve in Chianti is the birthplace of Giovanni da Verrazzano, the explorer who discovered New York Bay and gave his name to the Verrazano Narrows Bridge. The Badia a Passignano monastery winery (Antinori) is around 30 minutes. Many smaller estates welcome visitors without appointments.
Nature reserves nearby: Sant'Antonio and Vallombrosa (the latter is a famous Benedictine monastery in ancient forest, immortalised by Milton in Paradise Lost - "thick as autumnal leaves that strow the Brooks / In Vallombrosa").
Le Balze - the eroded sandstone crags just outside Figline, dramatic geological formations good for hiking.
La Chiantigiana road (SR222) - one of the most enchanting roads in Europe, a great road to drive into Chianti on.
Florence (30 mins by car / 40 mins by train): All the major sites - Uffizi, Accademia (David), Duomo, Oltrarno neighbourhood, Mercato Centrale. Train from Figline Valdarno avoids the parking problem entirely. Book Uffizi and Accademia tickets well in advance in high season.
Arezzo (35 mins): Often overlooked but genuinely rewarding - Piero della Francesca's Legend of the True Cross fresco cycle in San Francesco is one of the masterpieces of Italian Renaissance painting. The monthly antiques fair (first Sunday of each month) fills the Piazza Grande. The Giostra del Saracino jousting event runs in June and September.
San Giovanni Valdarno (10 mins): The birthplace of Masaccio, the painter who effectively invented Renaissance perspective. Small but worthwhile museum. Good for a quick stop rather than a full day.
Siena (1 hour): Gothic Duomo with inlaid marble floors, shell-shaped Piazza del Campo, Torre del Mangia. The Palio horse race runs on July 2 and August 16 - extraordinary spectacle but plan well ahead for accommodation.
Cooking and Wine on the Estate: The owners can arrange cooking classes in the Torre kitchen, sommelier-led wine tastings, guided cycling through the Chianti hills, and massage. These benefit from being booked before arrival.
Nearby Activities
- Figline Valdarno 10 mins
- Greve in Chianti 20 mins
- Florence 40 mins
- Arezzo 50 mins
- Siena 1hr 20 mins
Podere Gregorio
Sleeps: 18 to 22
From € 1,375 to 2,695 per day
From € 9,625 to € 16,170 per week
Approximately
$ 11,261 to $ 18,919 in USD
Calendar for Podere Gregorio
How to book
Is Podere Gregorio perfect for you?
For over 40 years, Invitation to Tuscany has personally selected and visited every villa we represent. Our team knows each property and its surroundings intimately - allowing us to help you choose the perfect home for your family or group, and to make your stay as memorable as the place itself.
How to Book
Check availability: View pricing and availability in the calendar above. To book online, click your desired arrival date, then your departure date. The calendar will grey out dates for stay lengths that aren't accepted—most villas book Saturday to Saturday, but many also allow shorter stays or flexible dates.
Need help choosing?
We visit our properties regularly and can provide firsthand advice based on your wishlist. Contact us and we'll help you select the best villa for your holiday. Secure your dates: We can hold your preferred dates for 48 hours while you confirm flights and coordinate with your group. To confirm, simply pay the 30% deposit. Your balance will be due 10 weeks before arrival.
Complimentary Concierge Service
Every booking includes our free concierge service to help make your stay special:
- Up to 3 activity or restaurant bookings per stay
- Local recommendations and insider knowledge
- Standard check-in coordination
- General travel assistance
Need more support? Our Concierge Plus (€300) provides dedicated planning support for guests requiring more activity bookings, larger group logistics, or special occasions. Please note that weddings and event planning do not fall under this. Request this when booking or as early as possible.
Flexible Booking Options
Easy cancellation: Add XCover to your booking for a full refund if you can't travel. You can add XCover anytime before paying your balance - just ask your agent. See our Booking Conditions and XCover for more information. Need to change dates? Let us know - we can often modify your booking rather than cancelling outright.
Worth Knowing
Tourist Tax: Many local administrations charge a tourist tax for rental accommodation, which varies by town. Charges typically range from €0.50 to €5 per person per night, with a maximum of 5-7 nights. Children are sometimes exempt. These charges are collected by property owners and paid directly to them.
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