Winchester, IN Homes

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  /14

  $139,000 Pending

  • 4 Beds
  • 1 Bath
  • 1,588 Sq Ft

  625 N West St, Winchester, IN 47394

  Freshly remodeled 3/4-bedroom, 1-bath home located in Winchester! This move-in-ready property features recent updates throughout, offering comfort and functionality at an affordable price. The fourth bedroom is smaller in size and does not have a closet, making it a great option for a home office, nursery, or cozy den. With a spacious overall layout and plenty of room to spread out, this home is

  Jammie Michael Tarter Realty Auction and Appraisal Company

  625 N West St, Winchester, IN 47394
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  /9

  $63,500 Sold Mar 20, 2026

  230 W South St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 1,076 Sq Ft
  • Built 1900

  Last Sold Summary

  • 9% Below List Price
  • $59/SF
  • 30 Days On Market

  Current Estimated Value $74,247

  Last Listing Agent Brody Tarter RE/MAX Evolve

  230 W South St, Winchester, IN 47394
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  /29

  Est $335,400 Not Listed For Sale

  4180 E Greenville Pike, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 2024

  4180 E Greenville Pike, Winchester, IN 47394

  Last Sold Summary

  • 2% Above List Price
  • $200/SF
  • 3 Days On Market

  Last Sold Price $329,900

  Last Listing Agent Brody Tarter Re/Max Evolve
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  /18

  $79,900

  • 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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  /17

  $310,000 Sold Jul 16, 2025

  1687 S 300 E, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,884 Sq Ft
  • Built 1900

  Last Sold Summary

  • 14% Below List Price
  • $165/SF
  • 109 Days On Market

  Current Estimated Value $336,807

  Last Listing Agent Paul Faddis Tarter Realty, Auction & Appraisals Co

  1687 S 300 E, Winchester, IN 47394
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  /32

  Est $269,181 Not Listed For Sale

  14 Deercross Dr, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft
  • Built 1999

  14 Deercross Dr, Winchester, IN 47394

  Last Sold Summary

  • 17% Above List Price
  • $139/SF
  • 107 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Brody Tarter RE/MAX
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  /33

  $264,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,423 Sq Ft

  19 Deer Cross Dr, Winchester, IN 47394

  Low-maintenance, community-oriented lifestyle on the Winchester Golf Course with over 1,400 SQ FT of living space. This home features 2 bedrooms, 2 full bathrooms with attached garage. Paver patio, central air, vaulted ceilings and open concept living and kitchen area. Master bedroom (18X20) has attached bathroom and large closets. Ventless fireplace in the living area. Plenty of curb appeal with

  Brody Tarter RE/MAX Evolve

  19 Deer Cross Dr, Winchester, IN 47394
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  /20

  $78,000 Sold Dec 08, 2025

  516 N Union St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 1,049 Sq Ft
  • Built 1900

  Last Sold Summary

  • 21% Below List Price
  • $74/SF
  • 12 Days On Market

  Current Estimated Value $87,309

  Last Listing Agent Debbie Busby Better Homes and Gardens First Realty Group

  516 N Union St, Winchester, IN 47394
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  /23

  Est $262,031 Not Listed For Sale

  17 Stonebridge Dr, Winchester, IN 47394

  • 2 Beds
  • 2 Baths
  • 1,246 Sq Ft
  • Built 2001

  17 Stonebridge Dr, Winchester, IN 47394

  Last Sold Summary

  • 8% Above List Price
  • $195/SF
  • 3 Days On Market

  Last Sold Price $242,575

  Last Listing Agent Brody Tarter RE/MAX
• 

  

  /18

  $119,900

  • 2 Beds
  • 1 Bath
  • 916 Sq Ft

  544 N Meridian St, Winchester, IN 47394

  Welcome to 544 N Meridian Street! This charming 2-bed, 1-bath home offers 916 square feet of comfortable living space with a spacious feel. You'll love the generously sized rooms and ample closet space, providing both functionality and flexibility. Recent updates - including fresh paint and new flooring - give the home a clean, modern touch while maintaining its inviting character. Whether you're

  Jairo Correa RE/MAX Evolve

  544 N Meridian St, Winchester, IN 47394
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  /31

  $199,900 Sold Dec 31, 2025

  317 E North St, Winchester, IN 47394

  • 4 Beds
  • 3 Baths
  • 1,810 Sq Ft
  • Built 1900

  Last Sold Summary

  • $110/SF
  • 4 Days On Market

  Current Estimated Value $187,951

  Last Listing Agent Mark Tooley Tarter Realty Auction and Appraisal Company

  317 E North St, Winchester, IN 47394
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  /50

  Est $472,975 Not Listed For Sale

  6 Peck Dr, Winchester, IN 47394

  • 4 Beds
  • 4 Baths
  • 3,177 Sq Ft
  • Built 1997

  6 Peck Dr, Winchester, IN 47394

  Last Sold Summary

  • 5% Above List Price
  • $142/SF
  • 12 Days On Market

  Last Sold Price $450,000

  Last Listing Agent Paul Faddis Tarter Realty, Auction & Appraisals Co
• 

  

  /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
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  /6

  $108,000 Sold May 22, 2025

  840 N West St, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1953

  Last Sold Summary

  • 3% Above List Price
  • $141/SF
  • 2 Days On Market

  Current Estimated Value $109,185

  Last Listing Agent Miranda Martin Re/Max Evolve

  840 N West St, Winchester, IN 47394
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  /36

  Est $489,775 Not Listed For Sale

  9 Peck Dr, Winchester, IN 47394

  • 3 Beds
  • 3 Baths
  • 4,248 Sq Ft
  • Built 1999

  9 Peck Dr, Winchester, IN 47394

  Last Sold Summary

  • 11% Below List Price
  • $129/SF
  • 0 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Brody Tarter RE/MAX
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  /21

  $94,900

  • 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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  /7

  $84,900 Sold May 19, 2025

  3268 S 400 W, Winchester, IN 47394

  • Land
  • 8.16 Acres
  • $10,404 per Acre

  Last Sold Summary

  • 1 Day On Market

  Current Estimated Value $94,381

  Last Listing Agent Andrew Wagner Wagner Auctioneering and Real Estate

  3268 S 400 W, Winchester, IN 47394
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  /21

  Est $269,527 Not Listed For Sale

  9 Shannon Dr, Winchester, IN 47394

  • 2 Beds
  • 2.5 Baths
  • 1,702 Sq Ft
  • Built 1997

  9 Shannon Dr, Winchester, IN 47394

  Last Sold Summary

  • 15% Above List Price
  • $138/SF
  • 155 Days On Market

  Last Sold Price $234,500

  Last Listing Agent Paul Faddis Tarter Realty, Auction & Appraisals Co
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  /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
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  /15

  $89,000 Sold Aug 15, 2025

  118 W Third St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 748 Sq Ft
  • Built 1920

  Last Sold Summary

  • 23% Below List Price
  • $119/SF
  • 119 Days On Market

  Current Estimated Value $89,712

  Last Listing Agent Paul Faddis Tarter Realty Auction and Appraisal Company

  118 W Third St, Winchester, IN 47394
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  /26

  Est $163,580 Not Listed For Sale

  835 S Beeson Dr, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft
  • Built 1978

  835 S Beeson Dr, Winchester, IN 47394

  Last Sold Summary

  • 11% Above List Price
  • $93/SF
  • 92 Days On Market

  Last Sold Price $147,000

  Last Listing Agent Brittany Cavanaugh Epique Inc.
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  /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
• 

  

  /25

  $125,000 Sold Sep 30, 2025

  619 S Richmond St, Winchester, IN 47394

  • 4 Beds
  • 1.5 Baths
  • 1,520 Sq Ft
  • Built 1900

  Last Sold Summary

  • 17% Below List Price
  • $82/SF
  • 43 Days On Market

  Current Estimated Value $122,353

  Last Listing Agent Miranda Martin Re/Max Evolve

  619 S Richmond St, Winchester, IN 47394
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  /10

  Est $127,493 Not Listed For Sale

  758 S Beeson Dr, Winchester, IN 47394

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

  758 S Beeson Dr, Winchester, IN 47394

  Last Sold Summary

  • 159% Above List Price
  • $49/SF
  • 0 Days On Market

  Last Sold Price $49,250

  Last Listing Agent Brody Tarter Re/Max Evolve
• 

  

  /23

  $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
• 

  

  /5

  $50,000 Sold Oct 15, 2025

  619 N Residence St, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 2,400 Sq Ft
  • Built 1875

  Last Sold Summary

  • 28% Below List Price
  • $21/SF
  • 96 Days On Market

  Current Estimated Value $106,273

  Last Listing Agent DAVE TARTER Tarter Realty, Auction & Appraisals Co

  619 N Residence St, Winchester, IN 47394
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  /11

  Est $119,820 Not Listed For Sale

  736 S Beeson Dr, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 1,096 Sq Ft
  • Built 1900

  736 S Beeson Dr, Winchester, IN 47394

  Last Sold Summary

  • 179% Above List Price
  • $39/SF
  • 4 Days On Market

  Last Sold Price $43,000

  Last Listing Agent Brody Tarter RE/MAX
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  /36

  $579,900 Open House 4/11

  • 3 Beds
  • 2 Baths
  • 1,399 Sq Ft

  1027 S Huntsville Rd, Winchester, IN 47394

  Stunning new construction featuring eye-catching stone accents and a beautifully designed open layout. The welcoming entry leads into a bright open-concept living room, dining area, and kitchen, creating an ideal space for everyday living and entertaining. Just off the kitchen, the primary suite offers scenic golf course views and a luxurious private bath complete with a tiled shower, soaking

  Paul Faddis Tarter Realty Auction and Appraisal Company

  1027 S Huntsville Rd, Winchester, IN 47394
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  /44

  $150,000 Sold Feb 24, 2026

  300 S Evans St, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 2,504 Sq Ft
  • Built 1906

  Last Sold Summary

  • $60/SF
  • 212 Days On Market

  Last Listing Agent Karin Barga EB Real Estate

  300 S Evans St, Winchester, IN 47394
• 

  

  /10

  Est $112,852 Not Listed For Sale

  722 S Beeson Dr, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1940

  722 S Beeson Dr, Winchester, IN 47394

  Last Sold Summary

  • 19% Above List Price
  • $65/SF
  • 2 Days On Market

  Last Sold Price $94,900

  Last Listing Agent Paul Faddis Tarter Realty Auction and Appraisal Company
• 

  

  /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
• 

  

  /19

  $185,000 Sold Oct 14, 2025

  176 Sunset Dr, Winchester, IN 47394

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

  Last Sold Summary

  • 5% Below List Price
  • $152/SF
  • 54 Days On Market

  Current Estimated Value $195,852

  Last Listing Agent Paul Faddis Tarter Realty, Auction & Appraisals Co

  176 Sunset Dr, Winchester, IN 47394
• 

  

  /19

  Est $242,900 Not Listed For Sale

  408 E 100 S, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,529 Sq Ft
  • Built 1993

  408 E 100 S, Winchester, IN 47394

  Last Sold Summary

  • 10% Below List Price
  • $177/SF
  • 97 Days On Market

  Last Sold Price $270,000

  Last Listing Agent Jairo Correa Re/Max Evolve
• 

  

  /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
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  /24

  $295,000 Sold Nov 14, 2025

  4803 W 500 N, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 1,703 Sq Ft
  • Built 1890

  Last Sold Summary

  • 2% Below List Price
  • $173/SF
  • 35 Days On Market

  Current Estimated Value $275,860

  Last Listing Agent Tyler Hartzell Tarter Realty Auction and Appraisal Company

  4803 W 500 N, Winchester, IN 47394
• 

  

  /11

  Est $158,931 Not Listed For Sale

  807 S Elm Blvd, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1978

  807 S Elm Blvd, Winchester, IN 47394

  Last Sold Summary

  • 40% Above List Price
  • $109/SF
  • 3 Days On Market

  Last Sold Price $113,500

  Last Listing Agent Mark Tooley Tarter Realty Auction and Appraisal Company
• 

  

  /36

  $334,900 Open House 4/11

  • 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
• 

  

  /9

  $40,000 Sold Apr 16, 2025

  529 W Franklin St, Winchester, IN 47394

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1900

  Last Sold Summary

  • 20% Below List Price
  • $28/SF
  • 2 Days On Market

  Current Estimated Value $103,196

  Last Listing Agent Brody Tarter Re/Max Evolve

  529 W Franklin St, Winchester, IN 47394
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  /7

  Est $46,374 Not Listed For Sale

  1030 E Cedar Rd, Winchester, IN 47394

  • 3 Beds
  • Built 1982

  1030 E Cedar Rd, Winchester, IN 47394

  Last Sold Summary

  • 209% Above List Price
  • $14/SF
  • 1 Day On Market

  Last Sold Price $15,000

  Last Listing Agent Diana Martin NonMember MEIAR
• 

  /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

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