Casa Olivia in Chianti

Casa Olivia rises above the hills of Chianti — a centuries-old Tuscan retreat shaped by stone, terracotta, and light.

Set within an established garden of ancient olive trees and stately cypresses, the historic stone house overlooks the countryside just outside Barberino Tavarnelle. It is a place that seems to gather many of Tuscany’s most compelling elements into one setting: rolling hills, vineyards, medieval villages, architecture layered with centuries of history — and that unmistakable Tuscan light, constantly shifting the mood of both house and landscape throughout the day.

Yet Casa Olivia never feels staged. The house has belonged to this landscape for centuries, and therein lies much of its appeal.

In the Heart of Chianti

Positioned between Florence and Siena, Casa Olivia offers an ideal base for exploring the region while remaining wonderfully removed from it all. The tiny medieval hamlet of Tignano is only minutes away, while Tavarnelle and Barberino Val d’Elsa offer cafés, restaurants, local shops, and everything needed for day-to-day life.

Narrow country roads wind from the house through vineyards and olive groves toward wineries, hilltop villages, and tucked-away trattorias. San Gimignano, Florence, and Siena are all within easy reach — although some of the most memorable days here may well be those with no particular destination at all.

A House with a Past

The origins of Casa Olivia date back to the 13th century. Historic church records suggest that the building served a number of different purposes over the course of its long life. Its distinctive tower, substantial stone walls, small window openings, and unconventional layout still reveal traces of that history today.

The house is also connected to one of those stories that linger in Tuscany somewhere between historical tradition and legend. It is believed that Dante Alighieri may have stayed — perhaps even lived for a period — in one of the rooms while he was in the area. The story cannot be documented with certainty, but it adds an intriguing layer to a house whose past already spans many centuries.

That historic fabric has been deliberately preserved. Terracotta floors, ancient timber beams, and natural stone provide the backdrop for interiors that feel contemporary and personal without overwhelming the character of the building.

The House

• Casa Olivia does not follow a conventional floor plan. Its original architecture sets the rhythm, creating a sequence of rooms with distinctly different moods.
• At the center of the ground floor are the fully equipped kitchen and adjoining dining room. Both feature large original stone fireplaces that remain fully functional and become natural gathering points on cooler evenings.
• On either side of this central section are two separate living rooms, each with its own purpose and personality. One is a relaxed media and reading room with a large television, books, and comfortable seating, as well as access to a small guest bathroom with shower. The second salon is warmer and more convivial, centered around a private bar and designed with the atmosphere of an intimate Tuscan drawing room.
• A separate staircase rises from each living room to the upper floor, creating two distinct sleeping wings, each with two individually designed double bedrooms. Three bathrooms with showers serve the four bedrooms. Original beams, terracotta, and stone are paired with carefully chosen textiles, understated colors, and contemporary details.
• From the first floor of the right wing, a wooden staircase ascends to the tower room — a quiet retreat for reading or working, furnished with a antique leather armchair and desk

This unusual layout works particularly well for families or friends traveling together: the heart of the house remains social and shared, while the two separate bedroom wings offer a welcome degree of privacy.

Terrace, Garden & Pool

• The covered terrace extends directly from both the kitchen and dining room, becoming an additional living space throughout the warmer months. A generous dining table, comfortable rattan furniture, and relaxed natural fabrics set the scene for long breakfasts, lunches in the shade, and dinners that stretch well beyond sunset.
• From here, the view opens across the lush, mature garden. Tall cypresses rise among olive trees and Mediterranean planting, giving the grounds the unmistakable silhouette of an old Tuscan estate.
• A path winds through the garden to the 13 × 6-meter swimming pool, positioned slightly below the house and opening fully toward the surrounding landscape.
• Framed in warm terracotta, the pool terrace offers several areas for sunbathing and relaxing. Eight elegant rattan loungers with pale cushions and three sun umbrellas are oriented toward the panorama. Beneath one vine-covered pergola is a generous rattan lounge area, while a second pergola, furnished with two armchairs and a small table, creates a more intimate place to retreat.