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A beautifully restored 14th-century convent, transformed into a luxurious contemporary villa

Nestled in the serene Chianti Hills of Tuscany, Le Masse di San Leolino is a beautifully restored 14th-century convent. Seamlessly combining historic charm with modern luxury, it offers the perfect place for a tranquil and memorable stay in one of Italy’s top wine regions.

The infinity pool overlooking the verdant countryside is perfect for a refreshing dip while enjoying the views. Post-swim, guests can recline on poolside loungers, relax in the wooden hot tub, or enjoy a friendly game of pétanque.

The villa boasts sprawling gardens bursting with colourful local flora for those who want to make the most of the outdoors. The private olive groves, fruit orchards, and vineyards are ideal for leisurely strolls or al fresco dining, while the medicinal herb garden offers a chance to learn more about the healing properties of these aromatic plants.

Throughout the grounds are several areas for outdoor dining and relaxation. Sunny terraces provide space to soak up the views, while the internal courtyard is the perfect setting for atmospheric meals or gatherings with loved ones.

The elegant villa interiors focus on comfort and style with a beautiful mix of antique and contemporary furniture in keeping with the restoration. Spacious living areas allow for both socialising and quiet moments of solitude, while the bright and airy dining room is ideal for convivial meals prepared in the large country-style kitchen.

Perfect for entertaining guests of all ages, the villa offers a plethora of amenities. From a cinema room for movie nights, a games room with a table tennis set for some friendly competition, a gym equipped with Technogym machines for fitness enthusiasts, to a sauna for post-workout relaxation, there’s something for everyone to enjoy.

Six well-appointed bedrooms sleep up to 12 guests comfortably, all offering en-suite or private facilities. One bedroom is on the ground floor, four bedrooms are on the first floor, and one bedroom is in the enchanting Upper Tower, which is accessed via the courtyard, perfect for a romantic escape.

For those seeking a luxurious Tuscan countryside escape with a touch of history and romance, Le Masse di San Leolino is the perfect choice.

CIN number: IT04821B58WE78Z5P

Highlights

Heated Swimming Pool

Heated Swimming Pool

Outdoor Hot Tub

Outdoor Hot Tub

Historic Property

Historic Property

Services

Included

Available extras

Enhance Your Stay with Personalised Services

After booking, your dedicated concierge will craft the perfect experience — tailored to your preferences. From everyday essentials to exclusive experiences, our curated add-ons elevate every villa stay.

Essential

Essential

Signature

Signature

Prestige

Prestige

Features

Indoor

Outdoor

Bedrooms

This property comfortably accommodates up to 12 guests in its 6 bedrooms.

MAIN VILLA – FIRST FLOOR
Bedroom 1 – super-king-size bed, lounge area with fireplace, walk-in wardrobe, and en-suite bathroom with dual vanity, bathtub & separate shower
Bedroom 2 – super-king-size bed (converted to twins on request), sitting area, and en-suite bathroom with dual vanity & shower
Bedroom 3 – king-size bed, fireplace, and en-suite bathroom with dual vanity, bathtub & separate shower
Bedroom 4 – super-king-size bed, sitting area, ensuite bathroom with dual vanity & shower, and garden access (via external staircase)

MAIN VILLA – GROUND FLOOR
Bedroom 5 – king-size bed, private living room, en-suite bathroom with shower, and courtyard access

MAIN VILLA – TOWER
Bedroom 6 – king-size bed and separate bathroom (on first floor, accessed via stairs) with dual vanity, bathtub, separate shower, and sauna

Location

Disclaimer: the location on the map may be approximate due to privacy reasons.

About the area

Le Masse di San Leolino is situated in the picturesque Pieve di San Leolino, providing stunning views of the rolling hills of Lamole and Volpaia in Chianti. Guests enjoy access to a tennis court just five minutes’ walk away (booking required).

A leisurely stroll from the villa is the charming town of Panzano in Chianti, known for its organic olive oils and wines. Visitors can explore quaint boutiques and local restaurants while enjoying the beautiful landscape.

The larger surrounding area is home to numerous top wineries, each offering unique experiences such as tastings, tours, and vineyard lunches. Additionally, visitors can delve into the region’s rich history by wandering through charming medieval villages and historic towns, including Greve in Chianti, Radda in Chianti, and Castellina in Chianti, all of which boast breathtaking views and delicious local cuisine.

Distances

Frequently asked questions

Inclusions vary by property but generally cover accommodation, cleaning services, and basic utilities. Some villas may also include additional services such as concierge, breakfast, or a private chef. Full details can be found on each villa’s page. If a service is not included in the price, our concierge team can arrange it for you, ensuring a fully personalised stay. Let us know your preferences, and we’ll take care of the rest!
Booking is simple! If you have a specific villa in mind, click "Send Enquiry" on its page. If you're considering multiple options, click the heart icon to save your favorites and send one enquiry for all of them. Our team will check availability and send you a detailed offer within 24 hours. Need help choosing? We’re happy to assist!
Yes, a deposit is required at the time of booking, typically 30% of the total amount. The remaining balance is usually due 30 to 90 days before check-in, depending on the property. Some villas may have different payment schedules, which will be specified in the offer we send you.
We accept bank transfers and major credit cards. Payment details will be provided during the booking process.
Yes, we offer a wide range of services, including in-villa options like private chefs, chauffeurs, and spa treatments, as well as activities such as yacht charters, wine tastings, and guided tours. We can also arrange experiences for the rest of your holiday, even beyond your villa stay. After booking, your dedicated concierge will contact you to customise your itinerary.
Yes, most high-end villas require a minimum stay of 7 nights, usually starting from a Saturday. However, many properties offer flexibility during certain times of the year, except for peak seasons like summer and Christmas holidays, which typically have stricter requirements. A smaller number of properties accept shorter stays year-round. If you have specific dates in mind, please contact us for availability.
Yes, we offer commission to travel agents booking on behalf of their clients. The commission amount varies by property, please contact us for specific details regarding a particular villa.

Have more questions?

Connect with our Villa Experts – we’ll handle the rest.

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From 39.500,00 EUR to 39.500,00 EUR per week

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