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Winchester, IN Homes for Sale

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  • /18

    $179,900

    • 3 Beds
    • 2 Baths
    • 2,010 Sq Ft

    527 W South St, Winchester, IN 47394

    Step into this welcoming home filled with charm, comfort, and thoughtful upgrades throughout. Beautiful hardwood floors lead you into a spacious living and dining room combo for an open, airy space perfect for hosting, relaxing, and everything in between. With two full bathrooms, you’ll enjoy a luxurious soaker tub in one and a brand-new shower in the other. Custom window blinds add both style

    Brianna Turner Key Realty Indiana

    527 W South St, Winchester, IN 47394
  • /19

    $244,900

    • 2 Beds
    • 2 Baths
    • 1,676 Sq Ft

    4 Crestwood Dr, Winchester, IN 47394

    Well-maintained brick ranch offering 2 bedrooms and 2 full bathrooms in Winchester. Recent updates include new paint, new flooring, and a new furnace installed in 2024. The home features an all-seasons room with tile flooring that opens to the back patio for warm-weather enjoyment. The family room offers large windows and flows into the living room, with multiple doorways creating an open yet

    Paul Faddis Tarter Realty Auction and Appraisal Company

    4 Crestwood Dr, Winchester, IN 47394
  • /23

    $209,900

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    501 N Maple St, Winchester, IN 47394

    Charming 3-bed, 2-bath brick ranch situated on a spacious oversized corner lot. This home offers great curb appeal and a functional layout, featuring an updated master suite with its own bathroom and walk-in closet. Enjoy the fenced backyard - perfect for pets, play or entertaining - plus the convenience of an attached 1.5-car garage. Lovingly cared for by the same family for over 25 years, this

    Jairo Correa RE/MAX Evolve

    501 N Maple St, Winchester, IN 47394
  • /28

    $269,900

    • 3 Beds
    • 2 Baths
    • 2,606 Sq Ft

    504 S Meridian St, Winchester, IN 47394

    NEW, NEW, NEW! Beautifully remodeled throughout, this move-in-ready home offers modern style and exceptional space. Step inside to a welcoming foyer that opens to a large living room, a separate dining room and a versatile office/bedroom. The updated kitchen sits conveniently next to a dedicated laundry room and a full bathroom completes the main level. Upstairs features two bright bedrooms and a

    Jairo Correa RE/MAX Evolve

    504 S Meridian St, Winchester, IN 47394
  • /15

    $109,900

    • 3 Beds
    • 1 Bath
    • 1,307 Sq Ft

    706 W Washington St, Winchester, IN 47394

    Updated 3 bedroom, 1 bathroom home in Winchester with large yard, deck and off-street parking. On the inside you will find a large utility room, central air, enclosed porch. 1 bedroom on the main floor and 2 bedrooms upstairs.

    Brody Tarter RE/MAX Evolve

    706 W Washington St, 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

    $64,900

    • Land
    • 2.38 Acres
    • $27,269 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
  • /22

    $94,900

    • 3 Beds
    • 1.5 Baths
    • 1,290 Sq Ft

    2212 E Greenville Pike, Winchester, IN 47394

    There is work to do in this one, but once it's finished, you'll have a great home in the country! nestled on a 1.3acre lot. this ranch may be just the fixer-upper you're looking for. Lots of potential for the right buyer. Sold as-is, inspections for buyer's knowledge only. Agents, please see agent remarks.

    Vanessa Lauritsen Hoosier Real Estate Group

    2212 E Greenville Pike, Winchester, IN 47394
  • /3

    $32,000

    • Land
    • 0.34 Acre
    • $94,118 per Acre

    Lot 5 Huntsville Rd, Winchester, IN 47394

    Check out this building lot on the beautiful Winchester Golf Course! Seller is a licensed agent.

    Paul Faddis Tarter Realty, Auction & Appraisals Co

    Lot 5 Huntsville Rd, Winchester, IN 47394
  • /22

    $134,900

    • 2 Beds
    • 1 Bath
    • 806 Sq Ft

    407 Westwood Dr, Winchester, IN 47394

    2-bedroom, 1-bath, one-level home located near Willard Elementary. The front living room features multiple windows and opens to an eat-in kitchen with a large pantry. The kitchen offers direct access to the attached one-car garage. The opposite end of the home includes two bedrooms with closets, with the bathroom and laundry located just outside the bedrooms. Recent updates include new carpet and

    Paul Faddis Tarter Realty Auction and Appraisal Company

    407 Westwood Dr, 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
  • /36

    $339,900

    • 3 Beds
    • 2.5 Baths
    • 2,096 Sq Ft

    889 S Huntsville Rd, Winchester, IN 47394

    Welcome to Willow Ridge III at the Winchester Golf Course! Built in 2023, this beautifully designed 3 bedroom, 2.5 bathroom home offers a modern yet functional layout perfect for today’s lifestyle. Enjoy cozy evenings by the stunning stone gas insert fireplace or entertain outdoors on the 14x18 covered stamped patio. Upstairs, the Jack & Jill bathroom layout is a must see, providing both style

    Jill Friend Tarter Realty Auction and Appraisal Company

    889 S Huntsville Rd, Winchester, IN 47394
  • /32

    $269,900

    • 2 Beds
    • 2 Baths
    • 1,388 Sq Ft

    28 Stonebridge Dr, Winchester, IN 47394

    Beautifully updated 2-bed, 2-bath condo featuring an open floor plan, modern finishes and abundant natural light. The master suite includes custom closets and a private full bath. Enjoy cooking in the stylish kitchen with stainless steel appliances. An attached 2-car garage provides added convenience and storage. Move-in ready and perfectly designed for low-maintenance living!

    Jairo Correa RE/MAX Evolve

    28 Stonebridge Dr, Winchester, IN 47394
  • /2

    $35,000

    • Land
    • 0.36 Acre
    • $97,222 per Acre

    1033 S Huntsville Rd, Winchester, IN 47394

    Check out this building lot on the beautiful Winchester Golf Course! Seller is a licensed agent.

    Paul Faddis Tarter Realty, Auction & Appraisals Co

    1033 S Huntsville Rd, Winchester, IN 47394
  • /24

    $129,900

    • 3 Beds
    • 1 Bath
    • 1,224 Sq Ft

    114 E Orange St, Winchester, IN 47394

    Updated home in Winchester with 3 bedrooms, 1 bathroom and an attached garage. Roof, siding and windows have all been recently replaced. Big kitchen with newer cabinets, appliances and flooring. USDA, FHA and VA buyers are welcomed.

    Brody Tarter RE/MAX Evolve

    114 E Orange St, Winchester, IN 47394
  • /36

    $164,900

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft

    603 S Stone St, Winchester, IN 47394

    Come see this beautifully renovated 3 bedroom, 2 full bath home in Winchester! This home offers a functional layout and timeless charm with modern updates throughout. Recent improvements include new vinyl plank flooring, carpet, cabinets, countertops, furnace, paint inside & out and central air unit. The durable metal roof was replaced in 2024, providing peace of mind for years to come. Move in

    Jill Friend Tarter Realty Auction and Appraisal Company

    603 S Stone St, Winchester, IN 47394
  • /27

    $359,900

    • 3 Beds
    • 2.5 Baths
    • 1,977 Sq Ft

    1041 S Huntsville Rd, Winchester, IN 47394

    BRAND NEW 3-bedroom, 2.5-bath home in Winchester with top-tier construction throughout. This open-concept layout is filled with natural light and features beautiful woodwork, solid interior doors, custom kitchen cabinetry, a large island, and pantry. The main-floor primary suite includes a private bath with a walk-in shower, while two bedrooms and a full bath are upstairs. Built with quality in

    Paul Faddis Tarter Realty Auction and Appraisal Company

    1041 S Huntsville Rd, Winchester, IN 47394
  • /23

    $118,900

    • 2 Beds
    • 1 Bath
    • 1,014 Sq Ft

    625 E Beech St, Winchester, IN 47394

    Charming 2 bedroom, 1 bath home featuring a welcoming covered front deck and a back deck. The property also includes a detached 2-car garage, offering ample parking and storage. There's main floor laundry in the spacious bathroom as well. Enjoy the large backyard with an additional concrete patio, ideal for gatherings or relaxing outdoors. A must-see home that combines comfort and convenience!

    Heather Clemmons Starr Real Estate LLC

    625 E Beech St, Winchester, IN 47394

Why Live in Winchester

Surrounded by farmland and intersected by forks of the White River, Winchester is a rural community of about 5,000 people and the seat of Randolph County. “I was born and raised in Winchester and found myself back in 2013 doing real estate. I try to ...

Frequently Asked Questions

What is the average home price in Winchester, IN?
Homes for sale in Winchester, IN have an average home price of $159,248.
How many homes have sold over the last 12 months in Winchester, IN?
125 homes have sold in Winchester, IN over the last 12 months.
What are the most popular zip codes in Winchester, IN?
The most popular zip codes in Winchester, IN include 47394, 47390, 47380, 47340 and 45390.
How much do you need to make to afford a house in Winchester?
The median home price in Winchester is $154,900. If you put a 20% down payment of $31,000 and had a 30-year fixed mortgage with an interest rate of 6.09%, your estimated principal and interest payment would be $750 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $32K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Winchester, IN?
Winchester, IN has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are O.R. Baker Elementary School, Willard Elementary School and Winchester Community High School. Browse all the schools in Winchester, IN to learn more.

Home Trends in Winchester, IN

Housing Trends

Median Sale Price
$141,000
Median Single Family Sale Price
$137,500
Median 2 Bedroom Sale Price
$189,900
Average Price Per Sq Ft
$97
Number of Homes for Sale
10
Last 12 months Home Sales
125
Months of Supply
1.00
Median List Price
$154,900
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
18%
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