Winchester, IN Homes

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  /36

  $169,900 Sold Sep 10, 2025

  • 1,733 Sq Ft
  • $98/SF
  • 3 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1937

  457 E South St, Winchester, IN 47394

  Charming 1937 Cape Cod Style Home with Bonus Apartment & Income Potential!! Step into timeless elegance with this beautiful 2-bedroom, 1.5-bathroom brick home, built in 1937. The home features stunning original hardwood floors, cedar closets, a cozy wood-burning fireplace in the spacious living room, solid wood doors and a formal dining room perfect for gatherings. Don't overlook the crown

  Jerrett Flesher Flesher Brothers Auctioneering and Real Estate Inc

  457 E South St, Winchester, IN 47394
• 

  

  

  /24

  Est $150,845 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,456 Sq Ft

  4662 E Union City Pike, Winchester, IN 47394

  4662 E Union City Pike, Winchester, IN 47394
• 

  

  

  /23

  $176,000

  • 3 Beds
  • 1 Bath
  • 1,746 Sq Ft

  300 S Evans St Unit Saratoga, 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 Unit Saratoga, Winchester, IN 47394
• 

  

  

  /16

  $182,000 Sold Sep 08, 2025

  • 1,548 Sq Ft
  • $118/SF
  • 24 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1959

  1392 E Washington St, Winchester, IN 47394

  Welcome to this charming and maintained 3 bedroom, 2 bathroom home offering 1,548 square feet of comfortable living space. Nestled on a generous .62 acre lot, this property provides both space and privacy with the convenience of a private well and septic system. Inside, you’ll love the natural light streaming through the beautiful bay window, adding warmth and character to the main living area.

  Jill Friend Tarter Realty Auction and Appraisal Company

  1392 E Washington St, Winchester, IN 47394
• 

  

  

  /32

  Est $276,561 Not Listed For Sale

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

  14 Deercross Dr, Winchester, IN 47394

  14 Deercross Dr, Winchester, IN 47394
• 

  

  /44

  $176,000

  • 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
• 

  

  /27

  $182,500 Sold Sep 03, 2025

  • 1,719 Sq Ft
  • $106/SF
  • 24 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1880

  1076 N Old Highway 27, Winchester, IN 47394

  Lovely 4 bed, 2 bath home that blends a charming farmhouse feel with modern update and conveniences. The spacious living room features a large window and classic archway that leads into the dining room. The updated kitchen includes a dishwasher, range, and breakfast bar. A hidden mudroom houses the laundry area and a nice pantry. A roomy main floor master has a private setting and access to the

  Ashley Swift-Morris RE/MAX Integrity Real Estate

  1076 N Old Highway 27, Winchester, IN 47394
• 

  

  /23

  Est $273,620 Not Listed For Sale

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

  17 Stonebridge Dr, Winchester, IN 47394

  17 Stonebridge Dr, Winchester, IN 47394
• 

  

  /19

  $158,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,704 Sq Ft

  1446 Harbours Woodland Ct, Winchester, IN 47394

  Take a look at this beautiful home nestled in a serene neighborhood just outside of Winchester. The main floor features a spacious primary bedroom for added convenience, while two additional bedrooms upstairs provide plenty of room for family or guests. Outside, you’ll love the detached garage and barn—perfect for storage, hobbies, or extra space. Whether you're enjoying the peaceful surroundings

  Jammie Michael Tarter Realty Auction and Appraisal Company

  1446 Harbours Woodland Ct, Winchester, IN 47394
• 

  

  /16

  $125,000 Sold Aug 29, 2025

  • 825 Sq Ft
  • $152/SF
  • 6 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1959

  534 S Western Ave, Winchester, IN 47394

  Welcome to this beautifully remodeled 2 bedroom, 1 bathroom home in the heart of Winchester! This charming property has been updated from top to bottom including roof, siding, fresh paint, new flooring, modern light fixtures, a new carport, landscaping, and a convenient storage shed. Perfectly situated in a great location, this home is move in ready and a must see!

  Paul Faddis Tarter Realty Auction and Appraisal Company

  534 S Western Ave, Winchester, IN 47394
• 

  

  /50

  Est $497,489 Not Listed For Sale

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

  6 Peck Dr, Winchester, IN 47394

  6 Peck Dr, Winchester, IN 47394
• 

  

  /19

  $139,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,370 Sq Ft

  232 E Washington St, Winchester, IN 47394

  2-bedroom, 1-bath home in Winchester featuring a spacious living room with electric fireplace, dining room, large utility room, and an office. Enjoy the porch, 1-car detached garage, and a chain-linked fenced backyard.

  Paul Faddis Tarter Realty Auction and Appraisal Company

  232 E Washington St, Winchester, IN 47394
• 

  

  /14

  $141,000 Sold Aug 29, 2025

  • 1,096 Sq Ft
  • $129/SF
  • 4 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  216 S West St, Winchester, IN 47394

  Welcome to this rejuvenated 2 bedroom, 1 bathroom home in Winchester! This property has been beautifully updated throughout featuring a new kitchen and bathroom, fresh luxury vinyl plank flooring and carpet, and a new central air unit and furnace for year round comfort. Outside, you’ll love the spacious fenced in yard and the attached 2 car garage that offers convenience and plenty of storage

  Jill Friend Tarter Realty Auction and Appraisal Company

  216 S West St, Winchester, IN 47394
• 

  

  /36

  Est $534,844 Not Listed For Sale

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

  9 Peck Dr, Winchester, IN 47394

  9 Peck Dr, Winchester, IN 47394
• 

  

  /28

  $179,900 Pending

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

  521 E Short St, Winchester, IN 47394

  Completely remodeled home in Winchester with plenty of space for your family! Located within walking distance of the Goodrich Park and High/Middle School, this home has a master bedroom/bathroom on the main floor and (3) large bedrooms upstairs. The living/kitchen area is open with recessed lighting, new cabinets, flooring and paint. Laundry room and full bathroom on the main floor. New HVAC,

  Brody Tarter RE/MAX Evolve

  521 E Short St, Winchester, IN 47394
• 

  

  /36

  $195,000 Sold Aug 28, 2025

  • 2,836 Sq Ft
  • $69/SF
  • 53 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  228 E North St, Winchester, IN 47394

  Large family home located in Winchester. 4 bedrooms with the possibility of a 5th along with 2 full bathrooms. You are greeted immediately with a large family room, stained glass and quarter sawn hardwood floors. Beautiful woodwork throughout and a great den with brick fireplace and gas insert perfect for an in-home office, mother-in-law suite or bedroom. A unique feature of the home are the

  Brody Tarter RE/MAX Evolve

  228 E North St, Winchester, IN 47394
• 

  

  /21

  Est $288,586 Not Listed For Sale

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

  9 Shannon Dr, Winchester, IN 47394

  9 Shannon Dr, Winchester, IN 47394
• 

  

  /26

  $195,000 Under Contract

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

  171 S Ball St, Winchester, IN 47394

  This 3-bedroom, 2.5-bath home sits on just over half an acre and offers the perfect balance of country charm and modern updates. The original attached garage has been converted into a spacious master suite, giving you plenty of room to relax and unwind. The home features a newer roof, comfortable living spaces, and a spa addition at the back of the house—ideal for year-round enjoyment. Outside,

  Emily Williams RE/MAX Evolve

  171 S Ball St, Winchester, IN 47394
• 

  

  /15

  $89,000 Sold Aug 15, 2025

  • 748 Sq Ft
  • $119/SF
  • 119 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1920

  118 W Third St, Winchester, IN 47394

  Charming and beautifully updated 2-bedroom, 1-bathroom home with a versatile bonus room perfect for an office or cozy den. This inviting property features modern finishes while maintaining its warm, welcoming character. Enjoy the convenience of a fenced-in yard, along with an 8x9 shed for extra storage. Don't miss this delightful home that's move-in ready and full of charm!

  Paul Faddis Tarter Realty Auction and Appraisal Company

  118 W Third St, Winchester, IN 47394
• 

  

  /11

  Est $88,098 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,096 Sq Ft

  736 S Beeson Dr, Winchester, IN 47394

  736 S Beeson Dr, Winchester, IN 47394
• 

  

  /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
• 

  

  /35

  $170,000 Sold Aug 11, 2025

  • 1,228 Sq Ft
  • $138/SF
  • 23 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1967

  4879 U S 27, Winchester, IN 47394

  Remodeled home with easy access to Winchester with 3 Bedrooms, 2 full Bathrooms, and a Detached Garage. Sitting on 2.5 +/- Acres with a storage shed. USDA, FHA, and VA buyers welcome.

  Brody Tarter Re/Max Evolve

  4879 U S 27, Winchester, IN 47394
• 

  

  /10

  Est $124,254 Not Listed For Sale

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

  722 S Beeson Dr, Winchester, IN 47394

  722 S Beeson Dr, Winchester, IN 47394
• 

  

  /25

  $374,900

  • 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 and Appraisal Company

  1041 S Huntsville Rd, Winchester, IN 47394
• 

  

  /11

  $125,000 Sold Aug 07, 2025

  • 1,264 Sq Ft
  • $99/SF
  • 23 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  407 W North St, Winchester, IN 47394

  Well maintained family home on a quiet street in Winchester. Standing seam roof, vinyl siding, huge front porch and an attached garage are features on the exterior. On the inside, you will find an updated kitchen with newer stainless appliances, new carpet and vinyl windows. There is a bedroom on the main floor with attached bathroom and 2 bedrooms on the upper floor. USDA, FHA and VA buyers

  Brody Tarter Re/Max Evolve

  407 W North St, Winchester, IN 47394
• 

  

  /27

  Est $84,056 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 938 Sq Ft

  105 Metz St, Winchester, IN 47394

  105 Metz St, Winchester, IN 47394
• 

  

  /23

  $128,999

  • 2 Beds
  • 1 Bath
  • 1,014 Sq Ft

  625 E Beech St, Winchester, IN 47394

  Charming 2 bedroom, 1 bath home featuring a welcoming covered front deck and a back deck. The property also includes a detached 2-car garage, offering ample parking and storage. There's main floor laundry in the spacious bathroom as well. Enjoy the large backyard with an additional concrete patio, ideal for gatherings or relaxing outdoors. A must-see home that combines comfort and convenience!

  Heather Clemmons Starr Real Estate LLC

  625 E Beech St, Winchester, IN 47394
• 

  

  /21

  $120,000 Sold Aug 01, 2025

  • 1,654 Sq Ft
  • $73/SF
  • 28 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  525 E Washington St, Winchester, IN 47394

  This centrally located 3-bed, 1-bath home offers comfort and convenience in one package. Enjoy relaxing mornings on the inviting front porch and make the most of the partially fenced backyard - ideal for outdoor activities or pets. A nice detached garage provides additional storage or workspace. Don't miss this great opportunity to own a well-situated home with solid features!

  Jairo Correa Re/Max Evolve

  525 E Washington St, Winchester, IN 47394
• 

  

  /11

  Est $145,409 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,384 Sq Ft

  216 E Watson St, Winchester, IN 47394

  216 E Watson St, Winchester, IN 47394
• 

  

  /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
• 

  

  /35

  $426,000 Sold Jul 31, 2025

  • 2,507 Sq Ft
  • $170/SF
  • 90 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1960

  953 S Main St, Winchester, IN 47394

  Nestled at the end of the secluded and picturesque PawPaw Lane, this beautiful brick home offers the perfect blend of luxury, privacy, and charm. Situated on approximately 6.5 acres at the edge of the city limits, the property provides plenty of space to enjoy the outdoors. The home features 4 spacious bedrooms and 3 full bathrooms, including a large master suite with a walk-in closet. A gas log

  Matt Tarter Tarter Realty Auction and Appraisal Company

  953 S Main St, Winchester, IN 47394
• 

  

  /11

  Est $161,663 Not Listed For Sale

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

  807 S Elm Blvd, Winchester, IN 47394

  807 S Elm Blvd, Winchester, IN 47394
• 

  

  /5

  $1,224,000

  • Land
  • 68 Acres
  • $18,000 per Acre

  TBD N 200 Rd E, Winchester, IN 47394

  ±68 Acres in White River Township, Winchester, Indiana for sale in 1 tract. Buyer will receive immediate possession at closing and the farm tenancy is open for the 2026 crop year. Bids for the property will be accepted from Monday, September 22nd through Friday, October 31st at noon. Purchase Agreement, along with proof of funds or financing approval, should be dropped off to 112 S Meridian St,

  Brody Tarter RE/MAX Evolve

  TBD N 200 Rd E, Winchester, IN 47394
• 

  

  /36

  $155,000 Sold Jul 29, 2025

  • 1,946 Sq Ft
  • $80/SF
  • 31 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1920

  2031 N 350 E, Winchester, IN 47394

  Opportunity knocks. This home owners has decided to make it a quick sale, we have marked the property down significantly and the seller is letting it go "as is" with one exception! A full price offer, we will replace the roof at the sellers expense! Land, outbuildings, brick home in a private rural setting with room to stretch your legs and grow a family. It's the perfect scenario for those

  Lucius Conner Viking Realty

  2031 N 350 E, Winchester, IN 47394
• 

  

  /7

  Est $62,504 Not Listed For Sale

  • 3 Beds

  1030 E Cedar Rd, Winchester, IN 47394

  1030 E Cedar Rd, Winchester, IN 47394
• 

  

  /17

  $79,500

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  215 Best Ave, Winchester, IN 47394

  3 bedroom, 2 bathroom home with approximately 1,280 square feet of living space, this two story property features a main level primary suite with walk-in closet and an updated full bath. Two additional bedrooms with a second full bath upstairs. The compact lot is easy to maintain while still providing room for outdoor enjoyment.

  Don Hall RE/MAX Evolve

  215 Best Ave, Winchester, IN 47394
• 

  

  /35

  $350,000 Sold Jul 22, 2025

  • 2,272 Sq Ft
  • $154/SF
  • 223 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  2468 S Us Highway 27, Winchester, IN 47394

  Charming Country Estate on 7 Acres with Modern Updates and Unique Features Welcome to your dream retreat! Nestled on 7 beautiful acres across two parcels, this 1.5-storyhome offers an extraordinary combination of modern updates and classic country charm. Thoughtfully renovated, this early 1900's "Rossville Sears Home" features everything from custom finishes to adaptable spaces that make it

  Gary Coats Flesher Brothers Auctioneering & Real Estate Inc.

  2468 S Us Highway 27, Winchester, IN 47394
• 

  

  /17

  Est $125,491 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  1051 E Greenville Pike, Winchester, IN 47394

  1051 E Greenville Pike, Winchester, IN 47394
• 

  

  /16

  $179,900

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

  170 Sunset Dr, Winchester, IN 47394

  This thoughtfully designed 2 bedroom, 2 bathroom condo offers a spacious living room that opens to a private back patio, a 2-car garage with a convenient utility closet, and an easy layout that’s ideal for everyday living. Located in Summers Pointe, just across from Walmart and close to local restaurants, shops, and gas stations — everything you need is right nearby.

  Paul Faddis Tarter Realty Auction and Appraisal Company

  170 Sunset Dr, Winchester, IN 47394
• 

  

  /36

  $350,000 Sold Jul 22, 2025

  • 2,272 Sq Ft
  • $154/SF
  • 223 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  2468 S Us Hwy 27, Winchester, IN 47394

  Charming Country Estate on 7 Acres with Modern Updates and Unique Features Welcome to your dream retreat! Nestled on 7 beautiful acres across two parcels, this 1.5-story home offers an extraordinary combination of modern updates and classic country charm. Thoughtfully renovated, this early 1900’s “Rossville Sears Home” features everything from custom finishes to adaptable spaces that make it

  Gary Coats Flesher Brothers Auctioneering and Real Estate Inc

  2468 S Us Hwy 27, Winchester, IN 47394

Showing Results 41 - 80, Page 2 of 18