Winchester, IN Homes

• 

  

  

  /31

  $194,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,554 Sq Ft

  1354 E Washington St, Winchester, IN 47394

  3 bedroom, 1 bathroom ranch home in Winchester on a corner half-acre lot. The living area features a gas log fireplace and floor-to-ceiling windows, opening to the dining room. The dining room has a doorway to the covered deck overlooking the backyard. Down the hall, all three bedrooms offer their own windows and closet space, with a full bath close by. The utility/laundry room off the kitchen

  Paul Faddis Tarter Realty Auction and Appraisal Company

  1354 E Washington St, Winchester, IN 47394
• 

  

  

  /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

  Current Estimated Value $121,943

  Last Listing Agent Jill Friend Tarter Realty Auction and Appraisal Company

  424 E South St, Winchester, IN 47394
• 

  

  

  /32

  Est $273,927

  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

  • 107 Days On Market

  Last Listing Agent Brody Tarter RE/MAX Evolve
• 

  

  

  /8

  $3,043,656

  • Land
  • 161.04 Acres
  • $18,900 per Acre

  0 N Unit 966954, Winchester, IN 47394

  Discover an exceptional 161-acre land offering located at the northwest corner of US Hwy 27 and W 300 N in Section 5 of White River Township, Randolph County, Indiana. With a proven cash-rent history and quality tillable ground, this tract presents an excellent opportunity for farmers, investors, or those seeking a significant land holding in a desirable location.

  Don Leis Leis Realty Company

  0 N Unit 966954, Winchester, IN 47394
• 

  

  

  /18

  $179,900

  Sold Jun 12, 2026

  527 W South St, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 2,010 Sq Ft
  • Built 1900

  Last Sold Summary

  • $90/SF
  • 168 Days On Market

  Current Estimated Value $180,359

  Last Listing Agent Brianna Turner Key Realty Indiana

  527 W South St, Winchester, IN 47394
• 

  

  /23

  Est $271,655

  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

  • 3 Days On Market

  Last Listing Agent Brody Tarter RE/MAX Evolve
• 

  

  /14

  $124,900

  $5K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 2,673 Sq Ft

  2015 E State Road 32, Winchester, IN 47394

  2,673 sq feet open concept with 2 bathrooms! Could be an awesome home outside of Winchester! 2 furnaces. Great roof and limestone structure! Would make an awesome daycare! 765-914-8169

  Jeff Hazelett Better Homes and Gardens First Realty Group

  2015 E State Road 32, Winchester, IN 47394
• 

  

  /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

  Current Estimated Value $197,207

  Last Listing Agent Brody Tarter RE/MAX Evolve

  544 N Main St, Winchester, IN 47394
• 

  

  /50

  Est $452,055

  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

  • 12 Days On Market

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

  

  /26

  $199,000

  $46K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /21

  Est $278,185

  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

  • 155 Days On Market

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

  

  /27

  $209,000

  $14K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,000 Sq Ft

  221 W South St, Winchester, IN 47394

  A rare find in the heart of Winchester. This solid brick home was built in 1900 and has been exceptionally well kept with so much character. The property boast over 2,000 sq feet with original wood finishes. Newer roof put on in the last 6 years. The basement offers additional extra space with a workshop and flexible area for storage or a cozy hangout space. Schedule your tour today!

  Austin Vandevender Coldwell Banker Lingle

  221 W South St, Winchester, IN 47394
• 

  

  /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 $86,483

  Last Listing Agent Jill Friend Tarter Realty Auction and Appraisal Company

  719 N West St, Winchester, IN 47394
• 

  

  /22

  Est $278,485

  Not Listed For Sale

  45 Stonebridge Dr, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,828 Sq Ft
  • Built 2006

  45 Stonebridge Dr, Winchester, IN 47394

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Andrew Wagner Wagner Auctioneering and Real Estate
• 

  

  /37

  $1,399,000

  • 3 Beds
  • 6 Baths
  • 12,880 Sq Ft

  35 N 300 W, Winchester, IN 47394

  Imagine waking up at home, walking to work, and building your family’s future around a business you own. Countryside Barkyard is a rare opportunity to acquire an established, high-end pet boarding, grooming and daycare business with a private residence on the same property. The purpose-built facility is fully operational, the customer base is established, and the residence provides a comfortable

  Paul Faddis Tarter Realty, Auction & Appraisals Co

  35 N 300 W, Winchester, IN 47394
• 

  

  /28

  $177,000

  Sold Dec 30, 2025

  521 E Short St, Winchester, IN 47394

  • 4 Beds
  • 2 Baths
  • 1,507 Sq Ft
  • Built 1900

  Last Sold Summary

  • 11% Below List Price
  • $117/SF
  • 204 Days On Market

  Current Estimated Value $163,679

  Last Listing Agent Brody Tarter RE/MAX Evolve

  521 E Short St, Winchester, IN 47394
• 

  

  /26

  Est $167,253

  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

  • 92 Days On Market

  Last Listing Agent Brittany Cavanaugh Epique Inc.
• 

  

  /19

  $109,900

  $10K PRICE DROP Pending

  • 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
• 

  

  /16

  $172,500

  Sold Mar 13, 2026

  170 Sunset Dr, Winchester, IN 47394

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft
  • Built 2011

  Last Sold Summary

  • 7% Below List Price
  • $141/SF
  • 199 Days On Market

  Current Estimated Value $182,683

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

  170 Sunset Dr, Winchester, IN 47394
• 

  

  /10

  Est $122,820

  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

  • 0 Days On Market

  Last Listing Agent Brody Tarter Re/Max Evolve
• 

  

  /7

  $349,900

  • Land
  • 3.57 Acres
  • $97,902 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 and Appraisal Company

  TBD Symmes Center Dr, Winchester, IN 47394
• 

  

  /14

  $141,000

  Sold Aug 29, 2025

  216 S West St, Winchester, IN 47394

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

  Last Sold Summary

  • 1% Above List Price
  • $129/SF
  • 4 Days On Market

  Current Estimated Value $124,399

  Last Listing Agent Jill Friend Tarter Realty Auction and Appraisal Company

  216 S West St, Winchester, IN 47394
• 

  

  /11

  Est $114,361

  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

  • 4 Days On Market

  Last Listing Agent Brody Tarter RE/MAX Evolve
• 

  

  /3

  $32,000

  • Land
  • 14,810 Sq Ft
  • $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
• 

  

  /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 $76,766

  Last Listing Agent Brody Tarter RE/MAX Evolve

  230 W South St, Winchester, IN 47394
• 

  

  /3

  Est $142,748

  Not Listed For Sale

  244 E Watson St, Winchester, IN 47394

  • 4 Beds
  • Built 1940

  244 E Watson St, Winchester, IN 47394

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Brody Tarter RE/MAX Evolve
• 

  

  /26

  $189,900

  • 3 Beds
  • 1.5 Baths
  • 1,456 Sq Ft

  508 S Clem St, Winchester, IN 47394

  One-story home in Winchester offering 3 bedrooms and 1.5 baths, all conveniently located on the same level. Built on a slab foundation with a gas furnace and central air for year-round comfort. A bright front living room welcomes you in, while a separate family room off the kitchen offers additional space to relax or entertain. The kitchen features a connected dining area and built-in laundry

  Paul Faddis Tarter Realty Auction and Appraisal Company

  508 S Clem St, Winchester, IN 47394
• 

  

  /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 $114,398

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

  516 N Union St, Winchester, IN 47394
• 

  

  /19

  Est $278,270

  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

  • 97 Days On Market

  Last Listing Agent Jairo Correa Re/Max Evolve
• 

  

  /33

  $239,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft

  569 SE Shadey Ln, Winchester, IN 47394

  This three-bedroom, two bath home sits on 1.4 acres just about one mile east of Winchester. The wooden deck off the back of the house offers a great view of the 1.4-acre completely fenced in lot that features some mature trees as well as several young trees and offers plenty of garden space. The home was completely gutted, down to the slab and exterior walls in 2020 due to a fire. A new floor

  Jerry Flanagan Wagner Auctioneering and Real Estate

  569 SE Shadey Ln, Winchester, IN 47394
• 

  

  /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 $188,542

  Last Listing Agent Mark Tooley Tarter Realty Auction and Appraisal Company

  317 E North St, Winchester, IN 47394
• 

  

  /35

  Est $382,758

  Not Listed For Sale

  953 S Main St, Winchester, IN 47394

  • 4 Beds
  • 3 Baths
  • 2,507 Sq Ft
  • Built 1960

  953 S Main St, Winchester, IN 47394

  Last Sold Summary

  • 90 Days On Market

  Last Listing Agent Matt Tarter Tarter Realty Auction and Appraisal Company
• 

  

  /36

  $579,900

  • 3 Beds
  • 2 Baths
  • 1,575 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 equipped with all new appliances, 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

  Paul Faddis Tarter Realty Auction and Appraisal Company

  1027 S 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 $123,610

  Last Listing Agent Miranda Martin Re/Max Evolve

  619 S Richmond St, Winchester, IN 47394
• 

  

  /7

  Est $60,018

  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

  • 1 Day On Market

  Last Listing Agent Diana Martin NonMember MEIAR
• 

  

  /5

  $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 +/- 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 and Appraisal Company

  TBD Symmes Center 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 $89,995

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

  619 N Residence St, Winchester, IN 47394
• 

  

  /20

  Est $192,667

  Not Listed For Sale

  104 Sunset Dr, Winchester, IN 47394

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft
  • Built 2025

  104 Sunset Dr, Winchester, IN 47394

  Last Sold Summary

  • 4 Days On Market

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

  

  /45

  $124,000

  Pending

  • 4 Beds
  • 1.5 Baths
  • 1,812 Sq Ft

  406 E South St, Winchester, IN 47394

  Welcome to this charming Victorian home in a great Winchester location! Rich in character and timeless architectural details, this spacious home offers over 2,300 square feet of living space with 4 bedrooms, 2 full bathrooms, and generously sized rooms throughout. From the moment you arrive, you'll appreciate the inviting wraparound front porch, stunning turret, and classic curb appeal that make

  Matt Tarter Tarter Realty Auction and Appraisal Company

  406 E South St, Winchester, IN 47394

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