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. Private Remarks
Sold
$1,765,000
3321 N Old Us Highway 421, Greensburg, IN 47240
4beds
5,906sqft
Residential, Farm
Built in 1856
14.6 Acres Lot
$-- Zestimate®
$299/sqft
$3,201 Estimated rent
Home value
Not available
Estimated sales range
Not available
$3,201/mo
Zestimate® history
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List your homeWhat's special
Decor barnExpanded main event hallNine fireplacesWrap-around porchFour bedroomsSweeping viewsOrnate trim
Zillow last checked:
Listing updated:
Listed by:
Torry Miller 812-614-2620,
Mossy Oak Properties
Source: MIBOR as distributed by MLS GRID,MLS#: 22088594
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Primary bedroom
- Level: Upper
- Area: 288 Square Feet
- Dimensions: 16x18
Bedroom 2
- Level: Upper
- Area: 168 Square Feet
- Dimensions: 12x14
Bedroom 3
- Level: Upper
- Area: 240 Square Feet
- Dimensions: 15x16
Bedroom 4
- Level: Upper
- Area: 240 Square Feet
- Dimensions: 15x16
Dining room
- Level: Main
- Area: 252 Square Feet
- Dimensions: 14x18
Kitchen
- Features: Tile-Ceramic
- Level: Main
- Area: 224 Square Feet
- Dimensions: 16x14
Laundry
- Features: Tile-Ceramic
- Level: Main
- Area: 120 Square Feet
- Dimensions: 10x12
Living room
- Level: Main
- Area: 288 Square Feet
- Dimensions: 16x18
Heating
- Forced Air, Heat Pump
Cooling
- Central Air
Appliances
- Included: Electric Cooktop, Dishwasher, Electric Water Heater, Refrigerator
Features
- Built-in Features, High Ceilings, Entrance Foyer, Hardwood Floors, Eat-in Kitchen, Smart Thermostat, Walk-In Closet(s)
- Flooring: Hardwood
- Basement: Cellar
- Number of fireplaces: 9
- Fireplace features: Gas Log
Interior area
- Total structure area: 5,906
- Total interior livable area: 5,906 sqft
- Finished area below ground: 90
Property
Parking
- Total spaces: 2
- Parking features: Detached
- Garage spaces: 2
Features
- Levels: Two
- Stories: 2
Lot
- Size: 14.6 Acres
- Features: Not In Subdivision, Rural - Not Subdivision, Mature Trees, Trees-Small (Under 20 Ft), Wooded
Details
- Additional parcels included: 160620310006.050017;160620310007.000001
- Parcel number: 160620310007010001
- Horse amenities: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Dutch Colonial
- Property subtype: Residential, Farm
- Attached to another structure: Yes
Materials
- Brick, Block
- Foundation: Concrete Perimeter
Condition
- Updated/Remodeled
- New construction: No
- Year built: 1856
Utilities & green energy
- Water: Public
Community & HOA
Community
- Subdivision: No Subdivision
HOA
- Has HOA: No
Location
- Region: Greensburg
Financial & listing details
- Price per square foot: $299/sqft
- Tax assessed value: $371,700
- Annual tax amount: $9,000
- Date on market: 3/13/2026
- Cumulative days on market: 7 days
Price history
| Date | Event | Price |
|---|---|---|
| 6/8/2026 | Sold | $1,765,000-8.4%$299/sqft |
Source:  MIBOR as distributed by MLS GRID #22088594 Report a problem | ||
| 3/17/2026 | Pending sale | $1,927,000$326/sqft |
Source: MLS of Southeastern Indiana #207000 Report a problem | ||
| 2/6/2026 | Listed for sale | $1,927,000+48.2%$326/sqft |
Source: REALSTACK #86831 Report a problem | ||
| 9/27/2022 | Sold | $1,300,000-13.3%$220/sqft |
Source: MIBOR as distributed by MLS GRID #21855668 Report a problem | ||
| 8/26/2022 | Pending sale | $1,500,000$254/sqft |
Source: MIBOR as distributed by MLS GRID #21855668 Report a problem | ||
| 6/16/2022 | Price change | $1,500,000-1.6%$254/sqft |
Source: MIBOR as distributed by MLS GRID #21855668 Report a problem | ||
| 5/24/2022 | Listed for sale | $1,525,000+48.8%$258/sqft |
Source: MIBOR as distributed by MLS GRID #21855668 Report a problem | ||
| 2/21/2019 | Sold | $1,025,000$174/sqft |
Source: Agent Provided Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2020 | $3,721 +16.6% | $371,700 -3.3% |
| 2019 | $3,192 +6.8% | $384,200 -0.1% |
| 2018 | $2,988 +1.7% | $384,700 +2% |
| 2017 | $2,937 -2.1% | $377,000 -0.1% |
| 2016 | $3,000 +3.1% | $377,300 -0.7% |
| 2014 | $2,909 -15.2% | $380,100 -7.2% |
| 2013 | $3,429 +5.7% | $409,700 +3.4% |
| 2012 | $3,245 -12.5% | $396,100 -7.5% |
| 2010 | $3,709 +40.4% | $428,100 +21.4% |
| 2009 | $2,642 | $352,700 +11.6% |
| 2007 | -- | $315,900 |
Find assessor info on the county website
Neighborhood: 47240
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Nearby schools
GreatSchools rating
- 7/10North Decatur Elementary SchoolGrades: K-6Distance: 3.7 mi
- 7/10North Decatur Jr-Sr High SchoolGrades: 7-12Distance: 3.7 mi
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- Indiana
- Decatur County
- Greensburg
- 47240
- 3321 N Old Us Highway 421
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