Winchester, IN Homes

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  /36

  $144,900

  • 2 Beds
  • 2 Baths
  • 1,764 Sq Ft

  326 S Meridian St, Winchester, IN 47394

  This classic home features 2 bedrooms with the possibility of a 3rd and 2 full bathrooms, 1 on each level. This house really does feel like home with the warm hardwood floors, classic woodwork, and inviting front porch. The den could be used as a bedroom on the main level. The owners have invested $50k+ in this home since purchasing it to remodel and upgrade, so now it is move in ready for

  

  Matt Glentzer

  RE/MAX Evolve

  (765) 790-5248

  326 S Meridian St, Winchester, IN 47394
• 

  

  

  /18

  $184,900 Sold Oct 17, 2025

  • 1,310 Sq Ft
  • $141/SF
  • 43 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1954

  3224 E Union City Pike, Winchester, IN 47394

  Set on 2 peaceful acres in rural Winchester, this 3-bedroom, 1-bath home offers the perfect blend of space, privacy, and character. Enjoy hardwood floors, a large living room, a welcoming kitchen and dining area, an attached 1-car garage, and a 20x30 detached garage for extra storage or workspace. With its charm and room to personalize, it’s a wonderful chance to embrace quiet country living just

  Paul Faddis Tarter Realty Auction and Appraisal Company

  3224 E Union City Pike, Winchester, IN 47394
• 

  

  

  /15

  Est $163,141 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 846 Sq Ft

  4058 N Us Hwy 27, Winchester, IN 47394

  4058 N Us Hwy 27, Winchester, IN 47394
• 

  

  

  /33

  $189,900

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

  162 Sunset Dr, Winchester, IN 47394

  New Roof and Gutters, Windows and Screens, Attic Insulation, Garage Door and Siding. Freshly painted interior (including garage) and carpet cleaning. This unit features a Sun Room overlooking a pond.

  

  Gary Coats

  Flesher Brothers Auctioneering & Real Estate Inc.

  (765) 737-2529

  162 Sunset Dr, Winchester, IN 47394
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  /5

  $50,000 Sold Oct 15, 2025

  • 2,400 Sq Ft
  • $21/SF
  • 96 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1875

  619 N Residence St, Winchester, IN 47394

  2-3 bedroom home close to the park and swimming pool. One car attached garage. Low exterior maintenance.

  DAVE TARTER Tarter Realty, Auction & Appraisals Co

  619 N Residence St, Winchester, IN 47394
• 

  

  /7

  Not Listed For Sale

  • 2 Beds
  • 4 Baths
  • 2,880 Sq Ft

  220 N Main St, Winchester, IN 47394

  220 N Main St, Winchester, IN 47394
• 

  

  /19

  $269,900

  • 3 Beds
  • 2.5 Baths
  • 1,642 Sq Ft

  919 Water View St, Winchester, IN 47394

  Currently under construction this extraordinary custom-built ranch home with nearly 1700 square feet has 3 bedrooms 2 baths and is currently being constructed in one of Winchesters most beautiful subdivisions “Lakeview Park”. This amazing Lakeview Construction home is one of the last 12 homes that will be constructed in the subdivision, and has a floor plan that is very modern and inviting. You

  

  Kyle Tom

  Coldwell Banker Lingle

  (765) 562-8784

  919 Water View St, Winchester, IN 47394
• 

  

  /30

  $235,000 Sold Oct 14, 2025

  • 2,202 Sq Ft
  • $107/SF
  • 25 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1934

  601 W Franklin St, Winchester, IN 47394

  Welcome to this inviting 3-bedroom, 2.5-bathroom home that offers comfort, character, and plenty of room to grow. The primary bedroom features its own en suite for added privacy, while the gas furnace and central air ensure year-round comfort. The main floor laundry adds convenience to your daily routine, and the living room’s wood-burning fireplace creates the perfect cozy gathering spot. The

  Mark Tooley Tarter Realty, Auction & Appraisals Co

  601 W Franklin St, Winchester, IN 47394
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  /15

  Est $181,087 Not Listed For Sale

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

  150 Sunset Dr, Winchester, IN 47394

  150 Sunset Dr, Winchester, IN 47394
• 

  

  /18

  $299,900

  • 3 Beds
  • 2.5 Baths
  • 2,093 Sq Ft

  924 Water View St, Winchester, IN 47394

  Currently under construction this extraordinary custom-built 2 Story home with nearly 2,100 square feet has 3 bedrooms 2 baths and is currently being constructed in one of Winchesters most beautiful subdivisions “Lakeview Park”. This amazing Lakeview Construction home is one of the last 12 homes that will be constructed in the subdivision, and has a floor plan that is very modern and inviting.

  

  Kyle Tom

  Coldwell Banker Lingle

  (765) 739-3258

  924 Water View St, Winchester, IN 47394
• 

  

  /19

  $185,000 Sold Oct 14, 2025

  • 1,220 Sq Ft
  • $152/SF
  • 54 Days On Market

  • 2 Beds
  • 2 Baths

  176 Sunset Dr, Winchester, IN 47394

  Newly updated 2 bed, 2 bath condo in desirable Summers Pointe! This charming unit offers a spacious living room with a cozy gas log fireplace, an adjoining office, and a beautiful back patio view. One bedroom sits next to the first full bath, while the primary suite includes a private bath with a stand-up shower. Enjoy the convenience of a 2 car attached garage that connects to the kitchen.

  Paul Faddis Tarter Realty, Auction & Appraisals Co

  176 Sunset Dr, Winchester, IN 47394
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  /28

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  2109 N 500 W, Winchester, IN 47394

  2109 N 500 W, Winchester, IN 47394
• 

  

  /36

  $84,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,384 Sq Ft

  613 S Main St, Winchester, IN 47394

  This 2 bedroom home could become a 3 bedroom by converting the attic space which already has a dedicated stairway. Metal roof is less than 3 years of age. Vinyl windows updated in last 5 years. Newer gas furnace. Front porch brick recently tuck pointed.

  

  Gary Coats

  Flesher Brothers Auctioneering and Real Estate Inc

  (765) 417-4158

  613 S Main St, Winchester, IN 47394
• 

  

  /50

  $307,000 Sold Oct 07, 2025

  • 2,090 Sq Ft
  • $147/SF
  • 63 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1955

  1430 E Union City Pike, Winchester, IN 47394

  Welcome to this stunning mid-century ranch, offering the perfect blend of charm, space, and modern updates. This beautifully renovated home boasts 2,090 square feet of living space with 3 bedrooms, 2 fully remodeled bathrooms, and a dedicated office—ideal for today’s work-from-home lifestyle. Step inside to an inviting open-concept floor plan, where the spacious living area seamlessly flows into

  Dustin Leis Leis Realty Company

  1430 E Union City Pike, Winchester, IN 47394
• 

  

  /25

  Est $331,978 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,044 Sq Ft

  5301 W 400 N, Winchester, IN 47394

  5301 W 400 N, Winchester, IN 47394
• 

  

  /23

  $174,900

  • 4 Beds
  • 2 Baths
  • 2,256 Sq Ft

  622 W South St, Winchester, IN 47394

  Spacious 4-bedroom, 2-bathroom home conveniently located across from Willard Elementary. This property features a large attached garage with a bonus room and plenty of storage throughout. Enjoy comfortable living with generous room sizes and practical spaces designed for everyday use.

  Matt Tarter Tarter Realty Auction & Apprai

  622 W South St, Winchester, IN 47394
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  /16

  $50,000 Sold Oct 07, 2025

  • 2,256 Sq Ft
  • $22/SF
  • 170 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1866

  439 S Meridian St, Winchester, IN 47394

  This charming 3-4 bedroom, 2 bathroom Victorian home offers ample space and great potential. It features a fenced yard, an attached garage and stunning woodwork along with beautiful hardwood floors.

  Jairo Correa RE/MAX Evolve

  439 S Meridian St, Winchester, IN 47394
• 

  

  /15

  Est $250,853 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,966 Sq Ft

  2747 W 500 S, Winchester, IN 47394

  2747 W 500 S, Winchester, IN 47394
• 

  

  /19

  $198,000

  • 3 Beds
  • 2 Baths
  • 2,291 Sq Ft

  316 E Franklin St, Winchester, IN 47394

  Welcome to this charming 3-4 bedroom, 2 full bathroom home in the heart of Winchester! Bursting with character, this property features spacious rooms throughout and a thoughtful layout. The large detached 3 car garage offers ample storage and parking, while the fenced in yard provides privacy for outdoor enjoyment. You’ll love the beautiful brick detail on the covered front porch, the convenience

  Jill Friend Tarter Realty Auction and Appraisal Company

  316 E Franklin St, Winchester, IN 47394
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  /24

  $200,000 Sold Oct 03, 2025

  • 1,392 Sq Ft
  • $144/SF
  • 38 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1875

  1492 S Old Highway 27, Winchester, IN 47394

  This 3-bedroom, 1.5-bath home features custom woodwork throughout and a beautifully crafted kitchen with red oak cabinets and custom barstools. Relax on the screened-in front porch or enjoy the meticulously landscaped yard. The large garden area has been enriched with compost for 48 years—ideal for any gardening enthusiast. Outside, you'll find a 25x19 enclosed carport and a 30x18 outbuilding

  Paul Faddis Tarter Realty Auction and Appraisal Company

  1492 S Old Highway 27, Winchester, IN 47394
• 

  

  /13

  Est $160,785 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,988 Sq Ft

  3587 W 500 S, Winchester, IN 47394

  3587 W 500 S, Winchester, IN 47394
• 

  

  /23

  $219,900

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  501 N Maple St, Winchester, IN 47394

  Charming 3-bed, 2-bath brick ranch situated on a spacious oversized corner lot. This home offers great curb appeal and a functional layout, featuring an updated master suite with its own bathroom and walk-in closet. Enjoy the fenced backyard - perfect for pets, play or entertaining - plus the convenience of an attached 1.5-car garage. Lovingly cared for by the same family for over 25 years, this

  Jairo Correa Re/Max Evolve

  501 N Maple St, Winchester, IN 47394
• 

  

  /36

  $387,000 Sold Oct 01, 2025

  • 2,259 Sq Ft
  • $171/SF
  • 34 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1920

  2554 E 100 S, Winchester, IN 47394

  Country Living at Its Best – Spacious Home with Barns, Shop & Gazebo Retreat! Beautifully maintained 4-bedroom, 2-1/2 bathroom farmhouse on 4.97 acres with 2,259 sq ft of finished living space. The heart of the home is the large eat-in kitchen, complete with solid oak cabinetry, a classic farmhouse porcelain sink, and plenty of counter space—ideal for gatherings and everyday living. You will also

  Jerrett Flesher Flesher Brothers Auctioneering and Real Estate Inc

  2554 E 100 S, Winchester, IN 47394
• 

  

  /20

  Est $177,215 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 2,244 Sq Ft

  3928 W 300 S, Winchester, IN 47394

  3928 W 300 S, Winchester, IN 47394
• 

  

  /18

  $219,900

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  742 S Huntsville Rd, Winchester, IN 47394

  Welcome to this beautifully updated 3-bedroom, 2-bath home in Winchester! This move-in ready property offers a well-designed floor plan with modern updates throughout. You’ll love the ample storage, large backyard perfect for gatherings or gardening, and the convenience of an attached garage. With its blend of comfort, style, and functionality, this home is ready for its next owner. Don’t miss

  Jammie Michael Tarter Realty Auction and Appraisal Company

  742 S Huntsville Rd, Winchester, IN 47394
• 

  

  /25

  $125,000 Sold Sep 30, 2025

  • 1,520 Sq Ft
  • $82/SF
  • 43 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1900

  619 S Richmond St, Winchester, IN 47394

  Spacious 4-bedroom, 1.5-bathroom home with a solid brick exterior and detached garage. Features a convenient half bath in one of the main floor bedrooms and recent upgrades throughout. A great mix of charm and modern updates!

  Miranda Fields Re/Max Evolve

  619 S Richmond St, Winchester, IN 47394
• 

  

  /7

  Est $64,702 Not Listed For Sale

  • 4 Beds

  1319 W 500 S, Winchester, IN 47394

  1319 W 500 S, Winchester, IN 47394
• 

  

  /16

  $139,900

  • 2 Beds
  • 1 Bath
  • 1,120 Sq Ft

  424 E South St, Winchester, IN 47394

  Nicely updated 2 bedroom, 1 bathroom home in Winchester. This property offers a comfortable layout with recent improvements throughout and a spacious fenced in yard. Conveniently located near town amenities, it’s move-in ready and waiting for its new owner.

  Jill Friend Tarter Realty Auction and Appraisal Company

  424 E South St, Winchester, IN 47394
• 

  

  /8

  $73,000 Sold Sep 26, 2025

  • 1,116 Sq Ft
  • $65/SF
  • 29 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  719 N West St, Winchester, IN 47394

  Welcome to this 2 bedroom, 1 bathroom home in Winchester! You’ll love the beautiful stone wood burning fireplace that creates a warm and inviting atmosphere. The property also features a detached 1 car garage, a covered front porch perfect for relaxing, and central air to keep you comfortable year round. Don’t miss your chance to make this cozy home yours!

  Jill Friend Tarter Realty Auction and Appraisal Company

  719 N West St, Winchester, IN 47394
• 

  

  /25

  Est $259,263 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft

  4020 S Bloomingsport Rd, Winchester, IN 47394

  4020 S Bloomingsport Rd, Winchester, IN 47394
• 

  

  /18

  $169,900

  • 3 Beds
  • 1 Bath
  • 1,257 Sq Ft

  2588 N Old Highway 27, Winchester, IN 47394

  3-bedroom, 1-bath home featuring numerous recent updates, including fresh paint, new flooring, roof, well pump, and kitchen counters. The home offers a functional layout with two main-level bedrooms and a spacious open upstairs area for the third bedroom, complete with closets in each room. Outside, enjoy a detached garage, additional storage shed, and a generous open backyard.

  Paul Faddis Tarter Realty Auction and Appraisal Company

  2588 N Old Highway 27, Winchester, IN 47394
• 

  

  /36

  $99,000 Sold Sep 16, 2025

  • 1,922 Sq Ft
  • $52/SF
  • 1 Day On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1960

  426 E South St, Winchester, IN 47394

  Quaint Dutch Colonial 3 bedroom, 1 1/2 bathroom home needs updates and repairs, priced at $55 per sq. ft. allows margin for such improvements to a buyer's preference. Dimensional shingle roof has less than 5 years of age since complete replacement so that's an improvement box that's already checked. This home features a spacious 28'x20' addition with wet bar and serving island with many usage

  Gary Coats Flesher Brothers Auctioneering and Real Estate Inc

  426 E South St, Winchester, IN 47394
• 

  

  /40

  Est $347,180 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,576 Sq Ft

  3023 S Base Rd, Winchester, IN 47394

  3023 S Base Rd, Winchester, IN 47394
• 

  

  /26

  $154,900

  • 4 Beds
  • 1 Bath
  • 1,864 Sq Ft

  410 E Thompson St, Winchester, IN 47394

  Welcome to 410 Thompson Street! This charming home offers 3-4 bedrooms, 1 bathroom and 1,864 sq ft of living space with spacious rooms throughout. Enjoy the outdoors with a large back deck, a fully fenced backyard with vinyl fencing and a detached garage for extra storage or parking. With its versatile layout and inviting features, this property is ready for you to make it your own.

  Jairo Correa Re/Max Evolve

  410 E Thompson St, Winchester, IN 47394
• 

  

  /24

  $280,000 Sold Sep 16, 2025

  • 2,368 Sq Ft
  • $118/SF
  • 70 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2005

  2 Saint Marys Cir, Winchester, IN 47394

  Welcome to this beautiful 4-bed, 2.5-bath home ideally located just minutes from a variety of local amenities. Step inside to an inviting open-concept layout that seamlessly connects the spacious living room and modern kitchen, perfect for everyday living and entertaining. Outside, you can enjoy relaxing mornings on the charming front porch or host guests on the back patio - ideal for summer

  Jairo Correa RE/MAX Evolve

  2 Saint Marys Cir, Winchester, IN 47394
• 

  

  /35

  Est $298,105 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,415 Sq Ft

  1088 E 250 S, Winchester, IN 47394

  1088 E 250 S, Winchester, IN 47394
• 

  

  /10

  $169,900

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

  1249 E Greenville Pike, Winchester, IN 47394

  Ranch home sitting just outside of Winchester on a large lot. 3 bedrooms, 1.5 bathroom with attached garage. Nicely updated kitchen, flooring and vinyl windows. Additional sheds for storage. Concrete driveway, central air and new gas furnace. Affordable utility bills.

  Brody Tarter RE/MAX Evolve

  1249 E Greenville Pike, Winchester, IN 47394
• 

  

  /13

  $103,900 Sold Sep 12, 2025

  • 877 Sq Ft
  • $118/SF
  • 159 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  419 E Carl St, Winchester, IN 47394

  Welcome to this charming newly-listed home! Boasting a practical layout with 2 cozy bedrooms and 1 well-appointed bathroom, this residence is designed for comfort. Recent upgrades ensure a turn-key experience, including a brand-new central air unit and various modern renovations that are sure to impress. The home features a detached garage - ideal for your vehicle or extra storage needs, and a

  Emily Williams Re/Max Evolve

  419 E Carl St, Winchester, IN 47394
• 

  

  /17

  Est $261,071 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,760 Sq Ft

  2615 E 200 S, Winchester, IN 47394

  2615 E 200 S, Winchester, IN 47394
• 

  

  /50

  $299,900

  • 4 Beds
  • 1 Bath
  • 1,703 Sq Ft

  4803 W 500 N, Winchester, IN 47394

  4803 West 500 North in Winchester, Indiana is a homesteader’s dream nestled on 6.7 scenic acres. This rural property blends comfort, practicality, and outdoor living, making it a perfect fit for those seeking country independence, investment opportunity, or a lifestyle rooted in agriculture and nature. It features a gorgeous 1.5-acre fully stocked pond, ideal for quiet evenings or fishing, paired

  BRIAN INGLE FC Tucker Richmond

  4803 W 500 N, Winchester, IN 47394

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