Winchester, IN Homes

• 

  

  

  /21

  Est $113,439

  Not Listed For Sale

  525 E Washington St, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 1,654 Sq Ft
  • Built 1900

  525 E Washington St, Winchester, IN 47394

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Jairo Correa Re/Max Evolve
• 

  

  

  /32

  $125,000

  $20K PRICE DROP Pending

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

  306 Best Ave, Winchester, IN 47394

  Welcome to this beautifully updated 3-bedroom, 1.5-bathroom home situated on a corner lot in Winchester! Featuring fresh, clean updates throughout, this move in ready home offers a bright and inviting atmosphere. Recent improvements include updated central air, new flooring, and numerous cosmetic updates that give the home a modern feel. Outside, you’ll enjoy a fully fenced backyard and a

  Jill Friend Tarter Realty Auction and Appraisal Company

  306 Best Ave, Winchester, IN 47394
• 

  

  /2

  $20,000

  Sold Sep 17, 2025

  0 W St Rd 32 Unit 10051896, 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 & Appraisals Co

  0 W St Rd 32 Unit 10051896, Winchester, IN 47394
• 

  

  

  /13

  Est $98,851

  Not Listed For Sale

  416 E North St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 1,014 Sq Ft
  • Built 1900

  416 E North St, Winchester, IN 47394

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Bryant Gentry Tarter Realty, Auction & Appraisals Co
• 

  

  

  /15

  $159,900

  $30K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,541 Sq Ft

  985 E Washington St, Winchester, IN 47394

  Brick and wood sided ranch style home on a large lot. 2 bedrooms 1.5 baths. Updated interior with new vinyl plank flooring in the kitchen and patio room, new carpet in the living rom and bedrooms. New paint. New well pump. 2 car attached garage and an addition detached garage, Sunroom. Fireplace.

  Mary Cordle Berkshire Hathaway Indiana Realty

  985 E Washington St, Winchester, IN 47394
• 

  

  /13

  $196,000

  Sold Aug 11, 2026

  548 W South St, Winchester, IN 47394

  • 4 Beds
  • 2 Baths
  • 2,579 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Below List Price
  • $76/SF
  • 15 Days On Market

  Current Estimated Value $196,587

  Last Listing Agent Brody Tarter RE/MAX Evolve

  548 W South St, Winchester, IN 47394
• 

  

  /8

  Est $97,216

  Not Listed For Sale

  420 E Short St, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 1,448 Sq Ft
  • Built 1900

  420 E Short St, Winchester, IN 47394

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Brody Tarter Re/Max Evolve
• 

  

  /49

  $939,900

  Pending

  • 6 Beds
  • 3.5 Baths
  • 3,648 Sq Ft

  4622 N US 27, Winchester, IN 47394

  39.35 total acres featuring approx. 25.5 tillable acres and a 6-bedroom, 3.5-bath home set on a professionally landscaped 3-acre yard. Two additions include a main-floor primary suite with private bath and 8-foot patio door, along with a grand foyer leading to formal dining, a stone fireplace family room, and an upper level with guest quarters, a study, and an additional bedroom. Hardwood floors

  Paul Faddis Tarter Realty Auction and Appraisal Company

  4622 N US 27, Winchester, IN 47394
• 

  

  /32

  $251,000

  Sold Jun 29, 2026

  1761 W Sr 32, Winchester, IN

  • 3 Beds
  • 2 Baths

  Last Sold Summary

  • 9% Below List Price
  • 6 Days On Market

  Current Estimated Value $264,620

  Last Listing Agent Matt Tarter Tarter Realty, Auction & Appraisals Co

  1761 W Sr 32, Winchester, IN
• 

  

  /8

  Est $123,007

  Not Listed For Sale

  416 E Short St, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 1,654 Sq Ft
  • Built 1900

  416 E Short St, Winchester, IN 47394

  Last Sold Summary

  • 104 Days On Market

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

  

  /36

  $319,900

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft

  4270 W State Road 32, Winchester, IN 47394

  Rare opportunity awaits! This 10-acre property offers the perfect blend of country living and versatility, featuring a pond, open pasture, barn with stables and a chicken coop that was previously set up as a dog kennel and now awaits some TLC. The 3-bedroom, 1-bath home features an open-concept kitchen, dining and living area with new flooring throughout. The walk-out basement provides an

  Miranda Martin RE/MAX Evolve

  4270 W State Road 32, Winchester, IN 47394
• 

  

  /22

  $157,000

  Sold Jul 23, 2026

  538 W Washington St, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,527 Sq Ft
  • Built 1906

  Last Sold Summary

  • 5% Above List Price
  • $103/SF
  • 3 Days On Market

  Current Estimated Value $152,848

  Last Listing Agent Andrew Wagner Wagner Auctioneering and Real Estate

  538 W Washington St, Winchester, IN 47394
• 

  

  /13

  Est $90,396

  Not Listed For Sale

  709 E Short St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 1,088 Sq Ft
  • Built 1900

  709 E Short St, Winchester, IN 47394

  Last Sold Summary

  • 1 Day On Market

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

  

  /15

  $129,900

  $5K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 1,534 Sq Ft

  240 E Watson St, Winchester, IN 47394

  This well-maintained 2-bedroom, 1-bath home offers the potential to easily convert an existing room into a 3rd bedroom, providing added flexibility for your needs. Recent updates include new carpet, newer interior paint, and a newer metal roof. Enjoy year-round comfort with forced-air heating and central air conditioning. Situated on approximately 1.417 acres within the city limits, this property

  Jerod Clark Green Realty Group

  240 E Watson St, Winchester, IN 47394
• 

  

  /16

  $125,000

  Sold Aug 29, 2025

  534 S Western Ave, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft
  • Built 1959

  Last Sold Summary

  • 12% Below List Price
  • $152/SF
  • 6 Days On Market

  Current Estimated Value $117,978

  Last Listing Agent Paul Faddis Tarter Realty Auction and Appraisal Company

  534 S Western Ave, Winchester, IN 47394
• 

  

  /21

  Est $159,425

  Not Listed For Sale

  521 N Oak St, Winchester, IN 47394

  • 4 Beds
  • 2 Baths
  • 1,590 Sq Ft
  • Built 1910

  521 N Oak St, Winchester, IN 47394

  Last Sold Summary

  • 65 Days On Market

  Last Listing Agent Curtis Cunningham Wagner Auctioneering and Real Estate
• 

  

  /31

  $239,900

  $10K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft

  1279 E Union City Pike, Winchester, IN 47394

  Enjoy peaceful country living on over 6 acres with this charming ranch-style home featuring an open-concept layout and a walkout basement. The property includes a hay field, an insulated and heated shed, and a barn, offering plenty of room for recreation, gardening, hobby farming, or simply enjoying the outdoors. The walkout basement provides additional living space, featuring a functional

  Jammie Michael Tarter Realty Auction and Appraisal Company

  1279 E Union City Pike, Winchester, IN 47394
• 

  

  /26

  $140,000

  Sold Dec 29, 2025

  410 E Thompson St, Winchester, IN 47394

  • 4 Beds
  • 1 Bath
  • 1,864 Sq Ft
  • Built 1900

  Last Sold Summary

  • 10% Below List Price
  • $75/SF
  • 68 Days On Market

  Current Estimated Value $144,390

  Last Listing Agent Jairo Correa RE/MAX Evolve

  410 E Thompson St, Winchester, IN 47394
• 

  

  /8

  Est $108,721

  Not Listed For Sale

  737 E Beech St, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 1,288 Sq Ft
  • Built 1957

  737 E Beech St, Winchester, IN 47394

  Last Sold Summary

  • 20 Days On Market

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

  

  /33

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 1,998 Sq Ft

  150 S Tamarac Dr, Winchester, IN 47394

  Stunning 3-bed, 2 full/2 half bath home offers over 2,000 sq ft of pure elegance. This spacious floor plan offers an abundance of natural light leading into an updated kitchen with new cabinetry, solid surface countertops. Master suite comes complete with a custom walk-in closet as well as an updated full bathroom. This home offers many features such as the on-demand hot water heater, affordable

  Brody Tarter RE/MAX Evolve

  150 S Tamarac Dr, Winchester, IN 47394
• 

  

  /27

  $182,500

  Sold Sep 03, 2025

  1076 N Old Highway 27, Winchester, IN 47394

  • 4 Beds
  • 1.5 Baths
  • 1,719 Sq Ft
  • Built 1880

  Last Sold Summary

  • 4% Below List Price
  • $106/SF
  • 24 Days On Market

  Current Estimated Value $173,572

  Last Listing Agent Ashley Swift-Morris RE/MAX Integrity Real Estate

  1076 N Old Highway 27, Winchester, IN 47394
• 

  

  /8

  Est $183,210

  Not Listed For Sale

  920 E Byrum Dr, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Built 1960

  920 E Byrum Dr, Winchester, IN 47394

  Last Sold Summary

  • 8 Days On Market

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

  

  /6

  $39,999

  • 5 Beds
  • 1 Bath
  • 2,080 Sq Ft

  300 E North St, Winchester, IN 47394

  Attention all investors! Check out this 5 bedroom, 1 bath home in Winchester ready to be brought back to life. Over 2000 square feet and situated on a nice lot, this home offers endless potential. Don't wait, schedule your showing today!

  Erika Rojas Trusted Realty Partners of Ind

  300 E North St, Winchester, IN 47394
• 

  

  /24

  $175,000

  Sold Jun 15, 2026

  404 E Thompson St, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,115 Sq Ft
  • Built 1900

  Last Sold Summary

  • 7% Below List Price
  • $157/SF
  • 57 Days On Market

  Current Estimated Value $174,261

  Last Listing Agent Matt Tarter Tarter Realty Auction & Apprai

  404 E Thompson St, Winchester, IN 47394
• 

  

  /9

  Est $124,307

  Not Listed For Sale

  942 E Short St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 1,006 Sq Ft
  • Built 1954

  942 E Short St, Winchester, IN 47394

  Last Sold Summary

  • 161 Days On Market

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

  /2

  $34,900

  • Land
  • 12,196 Sq Ft
  • $124,643 per Acre

  701 Englewood Dr, Winchester, IN 47394

  Brody Tarter RE/MAX Evolve

  701 Englewood Dr, Winchester, IN 47394
• 

  

  /33

  $189,900

  Sold Dec 12, 2025

  162 Sunset Dr, Winchester, IN 47394

  • 2 Beds
  • 2 Baths
  • 1,364 Sq Ft
  • Built 2012

  Last Sold Summary

  • $139/SF
  • 59 Days On Market

  Current Estimated Value $189,149

  Last Listing Agent Gary Coats Flesher Brothers Auctioneering Real Estate

  162 Sunset Dr, Winchester, IN 47394
• 

  

  /11

  Est $104,489

  Not Listed For Sale

  239 E Watson St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 1,159 Sq Ft
  • Built 1964

  239 E Watson St, Winchester, IN 47394

  Last Sold Summary

  • 198 Days On Market

  Last Listing Agent Brad Taflinger The Taflinger Real Estate Group
• 

  

  /6

  $3,043,656

  • Land
  • 161 Acres
  • $18,905 per Acre

  0 Hwy 27 W 300 N, 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 Hwy 27 W 300 N, Winchester, IN 47394
• 

  

  /15

  $175,000

  Sold Aug 24, 2026

  1167 N Old Highway 27, Winchester, IN 47394

  • 3 Beds
  • 1.5 Baths
  • 1,462 Sq Ft
  • Built 1981

  Last Sold Summary

  • 8% Below List Price
  • $120/SF
  • 11 Days On Market

  Current Estimated Value $185,924

  Last Listing Agent Matt Tarter Tarter Realty Auction & Apprai

  1167 N Old Highway 27, Winchester, IN 47394
• 

  

  /10

  Est $149,772

  Not Listed For Sale

  710 S Brown St, Winchester, IN 47394

  • 2 Beds
  • 1.5 Baths
  • 1,318 Sq Ft
  • Built 1982

  710 S Brown St, Winchester, IN 47394

  Last Sold Summary

  • 2 Days On Market

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

  

  /17

  $174,900

  New Construction

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  528 N Meridian St, Winchester, IN 47394

  Discover unparalleled modern living at 528 N Meridian ST, WINCHESTER, IN. Built in 2025, this brand-new single-family residence offers 1200 square feet of thoughtfully designed living space, promising a fresh start in a vibrant community. This inviting home features two comfortable bedrooms, providing ample private retreats for relaxation and personal space. A well-appointed full bathroom serves

  Doug Rector Doug Rector

  528 N Meridian St, Winchester, IN 47394
• 

  

  /3

  $1,020,000

  Sold Oct 20, 2025

  0 County Road 300 E, Winchester, IN 47394

  • Land
  • 60 Acres
  • $17,000 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 5 Days On Market

  Last Listing Agent Don Leis Leis Realty Company

  0 County Road 300 E, Winchester, IN 47394
• 

  

  /28

  Est $154,012

  Not Listed For Sale

  714 S Richmond St, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,686 Sq Ft
  • Built 1860

  714 S Richmond St, Winchester, IN 47394

  Last Sold Summary

  • 92 Days On Market

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

  

  /35

  $229,999

  $5K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,830 Sq Ft

  200 E South St, Winchester, IN 47394

  Make the discovery! NEW GUTTER SYSTEM BEING INSTALLED!! Looking for all the character of an older home with all the newer updates? This is the one! You won't find another one like it! This 5 Bed, 2 Bath home has a full unfinished basement and unfinished attic with a permanent staircase offering a blank canvas to significantly increase your square footage, over 5,000 total sqft! Multiple updates

  Shaina Chatman Austyn Avenue Real Estate

  200 E South St, Winchester, IN 47394
• 

  

  /20

  $110,000

  Sold Dec 19, 2025

  1071 N Old Highway 27, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1969

  Last Sold Summary

  • $118/SF
  • 22 Days On Market

  Current Estimated Value $108,838

  Last Listing Agent Jairo Correa Re/Max Evolve

  1071 N Old Highway 27, Winchester, IN 47394
• 

  

  /10

  Est $107,504

  Not Listed For Sale

  627 S Main St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 1,136 Sq Ft
  • Built 1900

  627 S Main St, Winchester, IN 47394

  Last Sold Summary

  • 8 Days On Market

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

  

  /19

  $49,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  713 E Short St, Winchester, IN 47394

  This 3BR/1BA home features plenty of opportunity with one bedroom on the main floor, two upstairs, a front living room, a dining room flowing into the kitchen overlooking the backyard, and a detached garage. Perfect for investors or buyers ready to make it their own.

  Paul Faddis Tarter Realty Auction and Appraisal Company

  713 E Short St, Winchester, IN 47394
• 

  

  /24

  $280,000

  Sold Sep 16, 2025

  2 Saint Marys Cir, Winchester, IN 47394

  • 4 Beds
  • 2.5 Baths
  • 2,368 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $118/SF
  • 70 Days On Market

  Current Estimated Value $256,906

  Last Listing Agent Jairo Correa RE/MAX Evolve

  2 Saint Marys Cir, Winchester, IN 47394
• 

  

  /28

  Est $148,470

  Not Listed For Sale

  500 S Richmond St, Winchester, IN 47394

  • 3 Beds
  • 1.5 Baths
  • 1,878 Sq Ft
  • Built 1900

  500 S Richmond St, Winchester, IN 47394

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Andrew Wagner Wagner Auctioneering and Real Estate

Showing Results 121 - 160, Page 4 of 18