Search results; Over 1,000 homes in MontepulcianoOver 1,000 homes in Montepulciano

This Montepulciano villa nestles you among vineyards with a private pool and hot tub

Look out over Val d’Orcia from your terrace at this Montepulciano condo

Wooden beams, stone walls, and a fireplace greet you at this Montepulciano loft

A 17th century Tuscan-style apartment in Montepulciano with a cinema room

Infinite valley views greet you at this Chiusi guesthouse with a private pool

Look out over Tuscan hills from this Montepulciano apartment’s terrace

Wake to valley views at this 17th-century Chiusi farmstay with breakfast included

A converted schoolhouse in Val d’Orcia where you’ll find a pool and garden

This spacious Montepulciano apartment puts you in the historic center among boutiques and wineries

This Pienza farmstay gives you Val d’Orcia views, a fireplace, and terracotta floors

This hilltop apartment in a 13th-century monastery gives you all of Montepulciano’s views

Wake to Val d’Orcia views from this vineyard-surrounded San Quirico farmstay

This renovated 1200s farmhouse in Chianciano Terme gives you a pool and resident hawks

This wine-inspired Montepulciano apartment gives you a shared garden and hammock

This 500-year-old house on 33 private acres gives you a pool and Tuscan hills

Valley views from your terrace at this XV-century Montepulciano condo

Look out over Val d’Orcia’s rolling hills from this Pienza farmstay’s travertine pool

This Trequanda apartment gives you panoramic hill views and a private garden