3321 N Old Us Highway 421 , Greensburg, IN 47240

Perched on the highest point between Cincinnati and Indianapolis, Highpoint Estate blends timeless 19th-century architecture with the flexibility of modern event spaces. Once home to State Senator Joseph Pleak, the estate has been thoughtfully restored and expanded to host everything from intimate gatherings to grand weddings of up to 500 guests. The expanded Main Event Hall (2024) anchors the property, seating up to 299 guests indoors with seamless tenting options for larger celebrations. A wrap-around porch, fully stocked bar, catering kitchen, 3-way liquor license with off-premise permit, and recent roof (2019) make hosting effortless and turnkey. Just steps away, the Mill Barn offers a rustic yet refined setting for up to 80 guests. With a new roof in 2025, two flexible levels, fireplaces, restrooms on each floor, and a covered patio spanning the length of the building, it’s both charming and comfortable. The 60-person rear terrace overlooks the orchard and gazebo stage, creating a perfect backdrop for ceremonies and receptions alike. At the heart of the estate sits the historic Pleak House, now known as Highpoint. This 5,006 sq. ft. residence features four bedrooms, three baths, nine fireplaces, original hardwood floors, ornate trim, and updated HVAC (2020), making it ideal for bridal suites, family lodging, or distinguished guest accommodations. Surrounded by 1,400 apple trees, an original 1858 smokehouse, and sweeping views, the property also includes a 76′ x 36′ workshop with walk-in cooler, decor barn, greenhouse, and parking for up to 450 guests. More than a venue, Highpoint Estate is a destination where history, beauty, and unforgettable memories meet.