Stunning Circa 1860 Italianate Victorian "Painted Lady", steps from Downtown Penn Yan & set on a generous deep lot in the heart of the Finger Lakes wine country. Exuding elegance across its expansive 4,290 sqft, the main house offers 4 generously sized bedrooms including 3 bed/full bath suites. Two grand parlors, a chestnut-paneled formal dining room, impeccable details such as hand-carved woodwork, soaring ceilings, & wallpaper transport you to a bygone era, while thoughtful modern updates ensure all the modern comforts. Adjacent to this stately home is a remarkable 1879 brick Carriage House, featuring 1,220 sqft of finished space above and two large garage bays, with central A/C, a full bath, and 200-amp 240-volt power. Perfect for a professional office, art studio, or additional living space, this Carriage House offers flexibility and income potential. The property’s outdoor space is equally impressive, with beautifully landscaped gardens featuring wisteria, hydrangea, and a grape arbor. With its prime location, historical significance, and business expansion potential—such as reopening its successful B&B—the possibilities for this property are endless!