Winchester, IN Homes for Sale with Acreage

/36
$309,000
- 4 Beds
- 1 Bath
- 2,492 Sq Ft
2980 S 225 E, Winchester, IN 47394

Discover the perfect blend of historic charm and rural comfort in this beautifully maintained 1900 farmhouse, offering 2,492 finished sq. ft. of inviting living space. Resting on 3.34 acres, this property is ideal for anyone seeking privacy, space, and a true country-living experience. The home features 4 bedrooms, including a spacious main-level primary suite. Upstairs, one of the bedrooms

Jerrett Flesher

Flesher Brothers Auctioneering and Real Estate Inc

(765) 754-4088

2980 S 225 E, Winchester, IN 47394
/23
$220,000
- 3 Beds
- 1 Bath
- 1,848 Sq Ft
684 E 225 N, Winchester, IN 47394

Discover this 3 bedroom, 1 bathroom farmhouse offering 1,848 square feet of living space, perfectly situated on just under 6 acres. This property is thoughtfully set up for livestock and outdoor living, combining country charm with updates. The home features dual heating, a newer refrigerator and dishwasher, new kitchen flooring (October 2025), and the metal roof was installed in 2019. Outdoor

Jill Friend Tarter Realty Auction and Appraisal Company

684 E 225 N, Winchester, IN 47394
/3
$349,900
- Land
- 3.57 Acres
- $98,011 per Acre
TBD Symmes Center Dr, Winchester, IN 47394

Great location on a high traffic road with easy access to Highway 27 & Highway 32. This 3.57 +/- Acre parcel is located near major retail, restaurants, medical, and residential. Several recent and current developments in the area make this an ideal location. There are additional parcels available as well.

Paul Faddis Tarter Realty, Auction & Appraisals Co

TBD Symmes Center Dr, Winchester, IN 47394
/4
$69,900
- Land
- 2.38 Acres
- $29,370 per Acre
TBD W 500 N, Winchester, IN 47394

2.38 acres located just north of IN-32 in Randolph County. The property includes a livestock barn with a hay loft and open ground. With its convenient location and versatile layout, this land offers plenty of potential for it's next owner.

Paul Faddis Tarter Realty Auction and Appraisal Company

TBD W 500 N, Winchester, IN 47394
/4
$364,900
- Land
- 3.44 Acres
- $106,076 per Acre
TBD Symmes Center Dr, Winchester, IN 47394

Great location on a high traffic road with easy access to Highway 27 & Highway 32. This 3.44 +/- Are parcel is located near major retail, restaurants, Medical, and residential. Several recent and current developments in the area make this an ideal location. There are additional parcels available as well. Call today for more information.

Paul Faddis Tarter Realty, Auction & Appraisals Co

TBD Symmes Center Dr, Winchester, IN 47394
/3
$249,900
- Land
- 1.49 Acres
- $167,718 per Acre
TBD Progress Blvd, Winchester, IN 47394

Prime 1.48-acre parcel on US 27, positioned near Walmart and a variety of thriving businesses including restaurants, retail stores, gas stations, and medical offices. High-visibility location with strong traffic counts makes this property an excellent opportunity for commercial development.

Paul Faddis Tarter Realty Auction and Appraisal Company

TBD Progress Blvd, Winchester, IN 47394
/10
$1
- Land
- 194 Acres
- $0 per Acre
500 W North St, Winchester, IN 47394

A rare chance to acquire quality farm ground in Northwest Randolph County! This property consists of approximately 194 acres of productive tillable ground, located at the intersection of 300 W and 500 N. Three adjoining lots will be sold together as one tract. Auction will be held online only on September 30, 2025 from 8:00 AM to 6:00 PM.

Matt Tarter Tarter Realty, Auction & Appraisals Co

500 W North St, Winchester, IN 47394

Indiana Randolph County Winchester

Home Trends in Winchester, IN

On average, homes in Winchester, IN sell after 38 days on the market compared to the national average of 53 days. The median sale price for homes in Winchester, IN over the last 12 months is $134,200, up 12% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$134,200

Median Single Family Sale Price

$133,400

Median 2 Bedroom Sale Price

$189,900

Average Price Per Sq Ft

$96

Number of Homes for Sale

Last 12 months Home Sales

120

Months of Supply

1.50

Median List Price

$147,400

Median Change From 1st List Price

Median Home Sale Price YoY Change

12%

How to Buy a Home How to Finance a Home How to Sell a Home

In Winchester, there are currently 7 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Winchester, IN offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Winchester and discover the potential and freedom that comes with owning your own piece of property.

Winchester Types of Homes for Sale

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