Winchester, IN Homes

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  /28

  $155,000 Pending

  • 5 Beds
  • 1 Bath
  • 2,626 Sq Ft

  766 W 300 N, Winchester, IN 47394

  Discover the potential of this spacious 5-bedroom, 1-bathroom home offering 2,600 finished square feet and set on five peaceful rural acres. This property combines the charm of country living with valuable improvements and abundant storage options—perfect for hobby farmers, collectors, or anyone seeking room to grow. The home is equipped with central air and a gas forced-air furnace, ensuring

  

  Jerrett Flesher

  Flesher Brothers Auctioneering and Real Estate Inc

  (765) 752-1030

  766 W 300 N, Winchester, IN 47394
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  /26

  $259,900 Sold Dec 09, 2025

  2 Crestwood Dr, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 2025

  Last Sold Summary

  • $158/SF
  • 1 Day On Market

  Last Listing Agent Brody Tarter RE/MAX Evolve

  2 Crestwood Dr, Winchester, IN 47394
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  /8

  Est $91,888 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  425 S Western Ave, Winchester, IN 47394

  425 S Western Ave, Winchester, IN 47394
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  /7

  $20,000

  • Land
  • 0.36 Acre
  • $55,556 per Acre

  545/555 Western Ave, Winchester, IN 47394

  This is your opportunity to build your dream home, multiple homes, or whatever you can imagine. The concrete pads of 2 garages still remain on this site. This piece of property contains 3 lots.

  

  Matt Glentzer

  RE/MAX Evolve

  (765) 308-5831

  545/555 Western Ave, Winchester, IN 47394
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  /30

  $235,000 Sold Oct 14, 2025

  601 W Franklin St, Winchester, IN 47394

  • 3 Beds
  • 2.5 Baths
  • 2,202 Sq Ft
  • Built 1934

  Last Sold Summary

  • 10% Below List Price
  • $107/SF
  • 25 Days On Market

  Current Estimated Value $231,039

  Last Listing Agent Mark Tooley Tarter Realty, Auction & Appraisals Co

  601 W Franklin St, Winchester, IN 47394
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  /15

  Est $153,733 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 846 Sq Ft

  4058 N Us Hwy 27, Winchester, IN 47394

  4058 N Us Hwy 27, Winchester, IN 47394
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  /36

  $297,000 Pending

  • 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
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  /9

  $122,000 Sold Apr 30, 2025

  515 W Franklin St, Winchester, IN 47394

  • 4 Beds
  • 2 Baths
  • 2,310 Sq Ft
  • Built 1900

  Last Sold Summary

  • 6% Below List Price
  • $53/SF
  • 1 Day On Market

  Current Estimated Value $152,982

  Last Listing Agent Brody Tarter Re/Max Evolve

  515 W Franklin St, Winchester, IN 47394
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  /7

  Not Listed For Sale

  • 2 Beds
  • 4 Baths
  • 2,880 Sq Ft

  220 N Main St, Winchester, IN 47394

  220 N Main St, Winchester, IN 47394
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  /36

  $139,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,764 Sq Ft

  326 S Meridian St, Winchester, IN 47394

  This classic home features 2 bedrooms with the possibility of a 3rd and 2 full bathrooms, 1 on each level. This house really does feel like home with the warm hardwood floors, classic woodwork, and inviting front porch. The den could be used as a bedroom on the main level. The owners have invested $50k+ in this home since purchasing it to remodel and upgrade, so now it is move in ready for you!

  

  Matt Glentzer

  RE/MAX Evolve

  (765) 790-5248

  326 S Meridian St, Winchester, IN 47394
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  /2

  $50,000 Sold Apr 25, 2025

  325 W Orange St, Winchester, IN 47394

  • Land
  • 2.39 Acres
  • $20,921 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 61 Days On Market

  Current Estimated Value $93,000

  Last Listing Agent Aaron Loy Loy Real Estate

  325 W Orange St, Winchester, IN 47394
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  /15

  Est $182,177 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft

  150 Sunset Dr, Winchester, IN 47394

  150 Sunset Dr, Winchester, IN 47394
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  /37

  $198,900

  • 2 Beds
  • 1 Bath

  5109 W Maxville Rd, Winchester, IN 47394

  Quaint 2 bedroom, 1 bathroom, 1200 square foot brick Ranch with full basement built in 1948 by Hinshaw Building Service of Winchester. 2 Acre home tract is being separated from farm land that has been in the same family since 1932

  

  Gary Coats

  Flesher Brothers Auctioneering Real Estate

  (765) 688-5417

  5109 W Maxville Rd, Winchester, IN 47394
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  /2

  $20,000 Sold Sep 17, 2025

  St Rd Indiana 32, Winchester, IN 47394

  • Land
  • 1.89 Acres
  • $10,582 per Acre

  Last Sold Summary

  • 43% Below List Price
  • 9 Days On Market

  Last Listing Agent Paul Faddis Tarter Realty Auction and Appraisal Company

  St Rd Indiana 32, Winchester, IN 47394
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  /28

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  2109 N 500 W, Winchester, IN 47394

  2109 N 500 W, Winchester, IN 47394
• 

  

  /23

  $174,900 Pending

  • 4 Beds
  • 2 Baths
  • 2,256 Sq Ft

  622 W South St, Winchester, IN 47394

  Spacious 4-bedroom, 2-bathroom home conveniently located across from Willard Elementary. This property features a large attached garage with a bonus room and plenty of storage throughout. Enjoy comfortable living with generous room sizes and practical spaces designed for everyday use.

  Matt Tarter Tarter Realty Auction & Apprai

  622 W South St, Winchester, IN 47394
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  /19

  $199,500 Sold Feb 27, 2025

  609 Englewood Dr, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,185 Sq Ft
  • Built 1969

  Last Sold Summary

  • 3% Below List Price
  • $168/SF
  • 9 Days On Market

  Current Estimated Value $205,204

  Last Listing Agent Jammie Michael Tarter Realty Auction and Appraisal Company

  609 Englewood Dr, Winchester, IN 47394
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  /25

  Est $298,442 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,044 Sq Ft

  5301 W 400 N, Winchester, IN 47394

  5301 W 400 N, Winchester, IN 47394
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  /15

  $109,900 Pending

  • 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
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  /10

  $49,250 Sold Jan 21, 2025

  758 S Beeson Dr, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1952

  Last Sold Summary

  • 1% Below List Price
  • $49/SF
  • 0 Days On Market

  Current Estimated Value $79,000

  Last Listing Agent Brody Tarter Re/Max Evolve

  758 S Beeson Dr, Winchester, IN 47394
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  /15

  Est $264,538 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,966 Sq Ft

  2747 W 500 S, Winchester, IN 47394

  2747 W 500 S, Winchester, IN 47394
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  /18

  $79,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,086 Sq Ft

  508 N West St, Winchester, IN 47394

  A great 2 bedroom, 1 bathroom home option in Winchester! This property features a spacious kitchen with plenty of room for dining, an oversized 1 car detached garage perfect for storage or hobbies, and an inviting enclosed front porch ideal for relaxing year round. Enjoy peace of mind with a durable metal roof and a convenient location close to downtown. Whether you’re a first time buyer or

  Jill Friend Tarter Realty Auction and Appraisal Company

  508 N West St, Winchester, IN 47394
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  /14

  $84,900 Sold Nov 04, 2025

  524 N Oak St, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1939

  Last Sold Summary

  • $80/SF
  • 11 Days On Market

  Last Listing Agent Jill Friend Tarter Realty, Auction & Appraisals Co

  524 N Oak St, Winchester, IN 47394
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  /13

  Est $181,810 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,988 Sq Ft

  3587 W 500 S, Winchester, IN 47394

  3587 W 500 S, Winchester, IN 47394
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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
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  /16

  $125,000 Sold Dec 23, 2025

  424 E South St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1939

  Last Sold Summary

  • 11% Below List Price
  • $112/SF
  • 35 Days On Market

  Last Listing Agent Jill Friend Tarter Realty Auction and Appraisal Company

  424 E South St, Winchester, IN 47394
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  /20

  Est $165,030 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 2,244 Sq Ft

  3928 W 300 S, Winchester, IN 47394

  3928 W 300 S, Winchester, IN 47394
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  /9

  $69,900

  • 2 Beds
  • 1 Bath
  • 1,076 Sq Ft

  230 W South St, Winchester, IN 47394

  2 bedroom, 1 bathroom home in Winchester.

  Brody Tarter RE/MAX Evolve

  230 W South St, Winchester, IN 47394
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  /30

  $225,000 Sold Mar 07, 2025

  892 S 125 E, Winchester, IN 47394

  • 4 Beds
  • 2 Baths
  • 2,352 Sq Ft
  • Built 1925

  Last Sold Summary

  • 10% Below List Price
  • $96/SF
  • 127 Days On Market

  Current Estimated Value $255,106

  Last Listing Agent Jill Friend Tarter Realty, Auction & Appraisals Co

  892 S 125 E, Winchester, IN 47394
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  /7

  Est $71,461 Not Listed For Sale

  • 4 Beds

  1319 W 500 S, Winchester, IN 47394

  1319 W 500 S, Winchester, IN 47394
• 

  

  /44

  $155,000

  • 3 Beds
  • 1 Bath

  300 S Evans St, Winchester, IN 47394

  Charming Home with a Countryside Feel! Experience the warmth of small-town living with a touch of countryside tranquility at 300 S. Evans Street, Saratoga, Indiana. Conveniently located near local favorites like Manning Pizza and Subs and Saratoga Park, this home is also just a short drive from both Union City and Winchester—offering the perfect blend of peaceful living and accessibility.Step

  Karin Barga EB Real Estate

  300 S Evans St, Winchester, IN 47394
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  /36

  $200,900 Sold Dec 30, 2025

  544 N Main St, Winchester, IN 47394

  • 5 Beds
  • 2 Baths
  • 2,349 Sq Ft
  • Built 1911

  Last Sold Summary

  • 19% Below List Price
  • $86/SF
  • 140 Days On Market

  Last Listing Agent Brody Tarter RE/MAX Evolve

  544 N Main St, Winchester, IN 47394
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  /40

  Est $346,016 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,576 Sq Ft

  3023 S Base Rd, Winchester, IN 47394

  3023 S Base Rd, Winchester, IN 47394
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  /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
• 

  

  /19

  $145,000 Sold Nov 10, 2025

  1446 Harbours Woodland Ct, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 1,704 Sq Ft
  • Built 1952

  Last Sold Summary

  • 12% Below List Price
  • $85/SF
  • 78 Days On Market

  Last Listing Agent Jammie Michael Tarter Realty Auction and Appraisal Company

  1446 Harbours Woodland Ct, Winchester, IN 47394
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  /35

  Est $273,827 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,415 Sq Ft

  1088 E 250 S, Winchester, IN 47394

  1088 E 250 S, Winchester, IN 47394
• 

  

  /21

  $94,900 Pending

  • 2 Beds
  • 1 Bath
  • 948 Sq Ft

  315 W Orange St, Winchester, IN 47394

  Step inside this beautifully remodeled 1.5-story home and fall in love with the modern updates and low-maintenance living. Every detail has been thoughtfully renovated --featuring new flooring, windows, siding, appliances, plumbing, and updated electrical throughout. The spacious kitchen has been completely remodeled and shines with new finishes and fixtures, perfect for home-cooked meals and

  Dean Retz Coldwell Banker Lingle

  315 W Orange St, Winchester, IN 47394
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  /8

  $73,000 Sold Sep 26, 2025

  719 N West St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 1,116 Sq Ft
  • Built 1900

  Last Sold Summary

  • 14% Below List Price
  • $65/SF
  • 29 Days On Market

  Current Estimated Value $77,170

  Last Listing Agent Jill Friend Tarter Realty Auction and Appraisal Company

  719 N West St, Winchester, IN 47394
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  /29

  Est $345,573 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  4180 E Greenville Pike, Winchester, IN 47394

  4180 E Greenville Pike, Winchester, IN 47394
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  /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

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