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.
INVESTMENT OPPORTUNITY Gross Rents are 164,088 yr Utilities are 35,720 yr. Taxes are 3,478 yr. Paved parking in back. Some remodeling in 2022 to current. 518 is 2,084 sf with 8 units, 2 have a Kitchen & Livingroom/Bedroom Combo & 6 are efficiency units. All have private bathrooms. 516 is 3 Buildings - The front building is 1- 2Bedroom Kit & Bath, 2 Efficiency units w/Baths. The buildings behind are all efficiency units with bathrooms x 6. 17 UNITS TOTAL.
INVESTMENT OPPORTUNITY located on the square in the heart of the Historic town of Greensburg. Art on the Square and This & That are the two businesses on the main level. There are 4- 1 Bedroom 1 Bath apartments on the upper level. One tenant has been there many years, also Art on the Square has been there many years. The town square offers a variety of eateries, as well as, quaint shops and services. 57,884 yr gross rental income. 4,031 yr for common electric & trash dumpster. Parking in rear. Common outside space in rear. Tenants pay Electric & Water-Sewer-metered separately. There is coin laundry that is in the process of getting repaired and would bring in 100-150/m. Net operating income only includes owner paid utilities and dumpster. This property is sold as a package only with 516 & 518 W. Main St. BLC #22073536
Great investment opportunity! This multi-tenant building features one first floor commercial space and two upstairs apartments. With all spaces fully occupied this is an excellent income producing property. This property includes a beautifully landscaped area with benches and lighting and has high visibility road frontage with being located on Main Street - AKA - State Road 46. This property is part of the historical downtown square and has an amazing view of the courthouse and the famous tower tree! Zoned - B, public parking in the front and the back, as well as a 2 space parking pad. Relax on the charming courtyard with nice landscaping and walkways. Subject to tenant rights.
Introducing a prime investment opportunity in Greensburg, IN. This distinguished Building offers a spacious 28,422 SF building, positioned on over 4 acres of prime land with 240 convenient parking spaces. Renovated in 2009, the versatile space offers multi-tenant layout and presents an exceptional opportunity for Retail, Church, Office, family entertainment center, and a wide range of other business Venues.
Albert Wright Page, License RB14038157, Xome Inc., License RC51300094, [email protected], 844-400-XOME (9663), 4471 North Billman Estates, Shelbyville, IN 46176

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Greensburg is located in Indiana. Greensburg, Indiana has a population of 11,573. Greensburg is more family-centric than the surrounding county with 36.07% of the households containing married families with children. The county average for households married with children is 35.98%.
The median household income in Greensburg, Indiana is $59,174. The median household income for the surrounding county is $65,000 compared to the national median of $69,021. The median age of people living in Greensburg is 39.6 years.
The average high temperature in July is 85 degrees, with an average low temperature in January of 19.5 degrees. The average rainfall is approximately 44.8 inches per year, with 13.8 inches of snow per year.