3321 N Old Us Highway 421, Greensburg, IN 47240

• 5,006 sqft

Property Description

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.

Listing Status:

Pending

Data Last Updated:

April 4, 2026 at 2:17PM

Listing Office:

Mossy Oak Properties : 812-614-2620

Listing Agent:

Torry Miller : 812-614-2620

MLS ID:

22082647

Exterior

• Parking: AsphaltGravelGarage Door OpenerGatedGuest

Construction

• Roofing: Metal

Location

• Road/Access: Asphalt
• Originating MLS: mibor
• School District: Decatur County Community Schools
• County: Decatur

Lot

• Zoning: Com Res16-06-20-310-007.010-001 Pt Sw 1/4 20-11-9 6.365 A Survey 202003374 16-06-20-310-006.050-017 PT E 1/2 SW 1/4 20-11-9 6.61 A TRACT 1 SURVEY 201100926 3-24-2011 16-06-20-310-007.000-001 PT SW 1/4 20-11-9 1.551 A160620310007010001
• View: RuralTrees/WoodsWaterView
• Fencing: PartialPrivacyFront YardGate
• Current Use: Orchard

Utilities

• Utilities: Electricity ConnectedSep Electric MeterSeptic SystemWater Connected
• Water: Well

Financial

• Source: mibor