Winchester, IN Homes

• 

  $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
• 

  

  

  /30

  Est $264,476

  Not Listed For Sale

  892 S 125 E, Winchester, IN 47394

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

  892 S 125 E, Winchester, IN 47394

  Last Sold Summary

  • 127 Days On Market

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

  

  

  /27

  $319,900

  $55K PRICE DROP Pending

  • 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 & Appraisals Co

  1041 S Huntsville Rd, 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 $196,141

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

  176 Sunset Dr, Winchester, IN 47394
• 

  

  

  /33

  Est $387,066

  Not Listed For Sale

  182 S Tamarac Dr, Winchester, IN 47394

  • 3 Beds
  • 2.5 Baths
  • 2,782 Sq Ft
  • Built 1989

  182 S Tamarac Dr, Winchester, IN 47394

  Last Sold Summary

  • 116 Days On Market

  Last Listing Agent Brody Tarter RE/MAX Evolve
• 

  

  /34

  $289,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  3577 S 100 E, Winchester, IN 47394

  Welcome to this beautifully maintained 3 bedroom, 2 bathroom home nestled on just over 2 acres, offering the perfect blend of comfort, space, and functionality. From the moment you arrive, you’ll appreciate the pride of ownership throughout this impressive property. The home features an oversized attached 2 car garage, while the 40’ x 32’ detached garage with a concrete floor and electricity

  Jill Friend Tarter Realty Auction and Appraisal Company

  3577 S 100 E, Winchester, IN 47394
• 

  

  /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 $294,405

  Last Listing Agent Tyler Hartzell Tarter Realty Auction and Appraisal Company

  4803 W 500 N, Winchester, IN 47394
• 

  

  /35

  Est $274,936

  Not Listed For Sale

  1810 E Washington St, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,779 Sq Ft
  • Built 1956

  1810 E Washington St, Winchester, IN 47394

  Last Sold Summary

  • 8 Days On Market

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

  

  /16

  $144,999

  $2K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,472 Sq Ft

  219 S Brown St, Winchester, IN 47394

  Welcome home to this charming and cozy 2 bedroom, 1.5 bathroom home in the heart of Winchester. This home features a large front porch perfect for enjoying this summer. Once inside you will find 1,472 sq feet of living space including a large living room that opens to an open concept kitchen and dining room. Upstairs your two bedrooms provide ample room for your family. The full bath upstairs

  Taylor Huntwork Vision One Real Estate

  219 S Brown St, Winchester, IN 47394
• 

  

  /33

  $255,000

  Sold Apr 28, 2026

  19 Deer Cross Dr, Winchester, IN 47394

  • 2 Beds
  • 2 Baths
  • 1,423 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $179/SF
  • 7 Days On Market

  Current Estimated Value $258,267

  Last Listing Agent Brody Tarter RE/MAX Evolve

  19 Deer Cross Dr, Winchester, IN 47394
• 

  

  /22

  Est $245,740

  Not Listed For Sale

  1496 E Washington St, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft
  • Built 1968

  1496 E Washington St, Winchester, IN 47394

  Last Sold Summary

  • 1 Day On Market

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

  

  /22

  $194,900

  $25K PRICE DROP Pending

  • 8 Beds
  • 5 Baths
  • 4,718 Sq Ft

  219 N East St Unit 2195, Winchester, IN 47394

  Welcome to this turnkey investment opportunity offering immediate income potential! This unique property features both a triplex and a duplex on one parcel, creating a rare chance to expand your portfolio with five income producing units. All tenants are currently in place on 1 year leases, providing stable cash flow from day one. Professionally managed by Tarter Realty, this property has seen

  Jill Friend Tarter Realty Auction and Appraisal Company

  219 N East St Unit 2195, Winchester, IN 47394
• 

  

  /10

  $164,000

  Sold Dec 19, 2025

  1249 E Greenville Pike, Winchester, IN 47394

  • 3 Beds
  • 1.5 Baths
  • 1,196 Sq Ft
  • Built 1957

  Last Sold Summary

  • 9% Below List Price
  • $137/SF
  • 102 Days On Market

  Current Estimated Value $173,899

  Last Listing Agent Brody Tarter RE/MAX Evolve

  1249 E Greenville Pike, Winchester, IN 47394
• 

  

  /5

  Not Listed For Sale

  749 S Brown St, Winchester, IN 47394

  • 4 Beds

  749 S Brown St, Winchester, IN 47394

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Brody Tarter RE/MAX Evolve
• 

  

  /27

  $335,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,783 Sq Ft

  518 Lissaaron Dr, Winchester, IN 47394

  Welcome to this stunning BRAND NEW construction in one of Winchester’s most desirable neighborhoods! Thoughtfully designed from top to bottom, this beautiful 3 bedroom, 2 bathroom ranch offers modern style, quality craftsmanship, and an inviting open concept layout perfect for everyday living and entertaining. Enjoy the convenience of an attached one car garage, spacious living areas, and a large

  Jill Friend Tarter Realty Auction and Appraisal Company

  518 Lissaaron Dr, Winchester, IN 47394
• 

  

  /13

  $103,900

  Sold Sep 12, 2025

  419 E Carl St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 877 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Below List Price
  • $118/SF
  • 159 Days On Market

  Current Estimated Value $103,412

  Last Listing Agent Emily Williams Re/Max Evolve

  419 E Carl St, Winchester, IN 47394
• 

  

  /14

  Est $116,502

  Not Listed For Sale

  447 E Elm St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 1,089 Sq Ft
  • Built 1954

  447 E Elm St, Winchester, IN 47394

  Last Sold Summary

  • 3 Days On Market

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

  

  /30

  $69,900

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,357 Sq Ft

  619 S Stone St, Winchester, IN 47394

  Welcome to this charming 1.5-story home offering 1,357 square feet of comfortable living space! It features 3 bedrooms, 1 full bath, and the convenience of a main-level laundry room. Enjoy the functional layout with room to make it your own. Step outside to a back deck overlooking the spacious backyard—perfect for entertaining, relaxing, or enjoying outdoor activities. A partial basement provides

  Heather Clemmons Starr Real Estate LLC

  619 S Stone St, Winchester, IN 47394
• 

  

  /21

  $95,000

  Sold Aug 03, 2026

  3156 Indiana 32, Winchester, IN 47394

  • 3 Beds
  • 2 Baths
  • 1,742 Sq Ft
  • Built 1930

  Last Sold Summary

  • 6% Above List Price
  • $55/SF
  • 11 Days On Market

  Last Listing Agent Terry Jenkins Jenkins Real Estate

  3156 Indiana 32, Winchester, IN 47394
• 

  

  /24

  Est $194,344

  Not Listed For Sale

  410 E Carl St, Winchester, IN 47394

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1920

  410 E Carl St, Winchester, IN 47394

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Jairo Correa RE/MAX Evolve
• 

  

  /30

  $294,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,589 Sq Ft

  703 Wedgewood Dr, Winchester, IN 47394

  Welcome home to this stunning newly constructed 3-bedroom, 2-bathroom ranch-style home, built in 2025 by Hallmark Homes and located in a great Winchester neighborhood! It offers a unique and thoughtfully designed open concept floor plan that blends modern style with everyday functionality. The spacious living area flows seamlessly into the kitchen and dining space, making it ideal for

  Jill Friend Tarter Realty Auction and Appraisal Company

  703 Wedgewood Dr, Winchester, IN 47394
• 

  

  /31

  $205,000

  Sold Jul 15, 2026

  2691 E 400 N, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 1,512 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Above List Price
  • $136/SF
  • 1 Day On Market

  Current Estimated Value $196,683

  Last Listing Agent Brady Yoder Tarter Realty Auction and Appraisal Company

  2691 E 400 N, Winchester, IN 47394
• 

  

  /20

  Est $148,504

  Not Listed For Sale

  451 E Carl St, Winchester, IN 47394

  • 4 Beds
  • 2.5 Baths
  • 1,590 Sq Ft
  • Built 1940

  451 E Carl St, Winchester, IN 47394

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Bryce Conyers Starr Real Estate LLC
• 

  

  /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
• 

  

  /18

  $184,900

  Sold Oct 17, 2025

  3224 E Union City Pike, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 1,310 Sq Ft
  • Built 1954

  Last Sold Summary

  • $141/SF
  • 43 Days On Market

  Current Estimated Value $177,012

  Last Listing Agent Paul Faddis Tarter Realty Auction and Appraisal Company

  3224 E Union City Pike, Winchester, IN 47394
• 

  

  /18

  Est $145,287

  Not Listed For Sale

  407 E Carl St, Winchester, IN 47394

  • 3 Beds
  • 1.5 Baths
  • 960 Sq Ft
  • Built 1964

  407 E Carl St, Winchester, IN 47394

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Brianna Turner Key Realty Indiana
• 

  

  /8

  $29,900

  $6K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 834 Sq Ft

  542 S Wall St, Winchester, IN 47394

  Charming house located at 542 S Wall St in Winchester, IN. A great opportunity to own a property in this area.

  Steven Koleno Beycome Brokerage Realty LLC

  542 S Wall St, Winchester, IN 47394
• 

  

  /36

  $387,000

  Sold Oct 01, 2025

  2554 E 100 S, Winchester, IN 47394

  • 4 Beds
  • 2.5 Baths
  • 2,259 Sq Ft
  • Built 1920

  Last Sold Summary

  • 6% Below List Price
  • $171/SF
  • 34 Days On Market

  Current Estimated Value $365,289

  Last Listing Agent Jerrett Flesher Flesher Brothers Auctioneering and Real Estate Inc

  2554 E 100 S, Winchester, IN 47394
• 

  

  /22

  Est $138,635

  Not Listed For Sale

  462 E Thompson St, Winchester, IN 47394

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft
  • Built 1900

  462 E Thompson St, Winchester, IN 47394

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Jairo Correa RE/MAX Evolve
• 

  

  /3

  $374,900

  • 12 Beds
  • 12 Baths
  • 910 Sq Ft

  3533 N 100 E, Winchester, IN 47394

  Here is your chance to purchase a high revenue generating property with excellent ROI that and upside. Currently there are 13 spaces with 12 units that are all owned by the seller. Seller is also including the swingset and basketball goal with this sale. All tenants pay their own electric and the landlord pays the common electric for the well. Currently landlord does not carry structural

  Andrew Wagner Wagner Auctioneering and Real Estate

  3533 N 100 E, Winchester, IN 47394
• 

  

  /21

  $85,000

  Sold May 29, 2026

  315 W Orange St, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 948 Sq Ft
  • Built 1900

  Last Sold Summary

  • 10% Below List Price
  • $90/SF
  • 173 Days On Market

  Current Estimated Value $94,108

  Last Listing Agent Dean Retz Coldwell Banker Lingle

  315 W Orange St, Winchester, IN 47394
• 

  

  /36

  Est $146,161

  Not Listed For Sale

  421 E South St, Winchester, IN 47394

  • 4 Beds
  • 1 Bath
  • 1,818 Sq Ft
  • Built 1908

  421 E South St, Winchester, IN 47394

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Gary Coats Flesher Brothers Auctioneering and Real Estate Inc
• 

  

  /23

  $164,900

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,360 Sq Ft

  810 S Elm Blvd, Winchester, IN 47394

  Welcome home to this well-maintained 3-bedroom, 1.5-bath property offering comfort, space, and numerous updates. The home features central air and a cozy wood-burning fireplace, perfect for relaxing evenings. Recent improvements include a new roof, vinyl plank flooring, new carpet, most windows, and updated light fixtures throughout. The spacious backyard provides plenty of room to enjoy the

  Mark Tooley Tarter Realty, Auction & Appraisals Co

  810 S Elm Blvd, Winchester, IN 47394
• 

  

  /22

  $82,000

  Sold Mar 23, 2026

  2212 E Greenville Pike, Winchester, IN 47394

  • 3 Beds
  • 1.5 Baths
  • 1,290 Sq Ft
  • Built 1890

  Last Sold Summary

  • 18% Below List Price
  • $64/SF
  • 53 Days On Market

  Current Estimated Value $93,113

  Last Listing Agent Vanessa Lauritsen Hoosier Real Estate Group

  2212 E Greenville Pike, Winchester, IN 47394
• 

  

  /16

  Est $173,327

  Not Listed For Sale

  833 E Washington St, Winchester, IN 47394

  • 3 Beds
  • 1.5 Baths
  • 1,890 Sq Ft
  • Built 1964

  833 E Washington St, Winchester, IN 47394

  Last Sold Summary

  • 55 Days On Market

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

  /2

  $35,000

  • Land
  • 15,681 Sq Ft
  • $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
• 

  

  /14

  $120,000

  Sold May 04, 2026

  407 Westwood Dr, Winchester, IN 47394

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft
  • Built 1948

  Last Sold Summary

  • 11% Below List Price
  • $149/SF
  • 54 Days On Market

  Current Estimated Value $124,187

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

  407 Westwood Dr, Winchester, IN 47394
• 

  

  /26

  Est $175,390

  Not Listed For Sale

  615 E Washington St, Winchester, IN 47394

  • 4 Beds
  • 1.5 Baths
  • 1,560 Sq Ft
  • Built 1937

  615 E Washington St, Winchester, IN 47394

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Jairo Correa Re/Max Evolve
• 

  

  /25

  $159,900

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  523 S Richmond St, Winchester, IN 47394

  3-bedroom, 1-bath home in Winchester featuring a functional layout and tasteful updates throughout. The front living room connects to two bedrooms and showcases hardwood flooring. The updated kitchen offers new upper cabinets, countertops, and fresh paint, while the modernized bathroom provides a bright, spacious feel. The rear primary bedroom features new flooring and a closet. A spacious

  Paul Faddis Tarter Realty Auction and Appraisal Company

  523 S Richmond St, Winchester, IN 47394
• 

  

  /26

  $187,000

  Sold Dec 19, 2025

  171 S Ball St, Winchester, IN 47394

  • 3 Beds
  • 2.5 Baths
  • 1,890 Sq Ft
  • Built 1958

  Last Sold Summary

  • 4% Below List Price
  • $99/SF
  • 105 Days On Market

  Last Listing Agent Emily Williams RE/MAX Evolve

  171 S Ball St, Winchester, IN 47394

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