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Winchester, IN Homes for Sale

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  • /35

    $370,000

    • 4 Beds
    • 2 Baths
    • 2,272 Sq Ft

    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

    Agent Photo

    Gary Coats

    Flesher Brothers Auctioneering & Real Estate Inc.

    (765) 375-1550

    2468 S Us Highway 27, Winchester, IN 47394
  • /36

    $370,000

    • 4 Beds
    • 2 Baths
    • 2,272 Sq Ft

    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

    Agent Photo

    Gary Coats

    Flesher Brothers Auctioneering and Real Estate Inc

    (765) 542-5323

    2468 S Us Hwy 27, Winchester, IN 47394
  • /36

    $86,900

    • 2 Beds
    • 1 Bath

    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.

    Agent Photo

    Gary Coats

    Flesher Brothers Auctioneering Real Estate

    (765) 417-4158

    613 S 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

    Agent Photo

    Kyle Tom

    Coldwell Banker Lingle

    (765) 562-8784

    919 Water View St, 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.

    Agent Photo

    Kyle Tom

    Coldwell Banker Lingle

    (765) 739-3258

    924 Water View St, Winchester, IN 47394
  • /5

    $984,500

    • Land
    • 55 Acres
    • $17,900 per Acre

    Co Rd 500 N, Winchester, IN 47390

    55 Acres of Productive Farmland Ready for Your OperationSituated in Jackson Township, Randolph County, Indiana, this 55-acre farm is a fantastic opportunity for farmers looking to expand their operation. With approximately 52 tillable acres, the ground is currently cash rented for the 2025 season, offering immediate income or the option to plan ahead for your own use. The land is

    Dustin Leis Leis Realty

    Co Rd 500 N, Winchester, IN 47390
  • /35

    $199,900

    • 3 Beds
    • 2 Baths
    • 1,228 Sq Ft

    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
  • /36

    $219,900

    • 4 Beds
    • 2 Baths
    • 2,836 Sq Ft

    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
  • /57

    $348,500

    • 3 Beds
    • 2 Baths
    • 2,090 Sq Ft

    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
  • /24

    $289,900

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

    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
  • /36

    $249,900

    • 3 Beds
    • 1.5 Baths
    • 1,946 Sq Ft

    2031 N 350 E, Winchester, IN 47394

    This home is a 'Choose your own adventure' of real estate purchases. It needs some work, the seller is willing to do that work. Also, the seller is willing to make an awesome deal. Think about it! You can save thousands by doing some of you own work and buying the home cheaper, or we can call in the contractors and get them to work! Write your own story to include this amazing setting,

    Lucius Conner Viking Realty

    2031 N 350 E, Winchester, IN 47394
  • /31

    $399,900

    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    2105 N 100 W, Winchester, IN 47394

    Brick home located on 8 acres just outside of Winchester with approximately 3 acres of woods. There is a large pole building (30'X48') with concrete floor and 9' overhead door. The home was built in 1979 and has a full walkout basement that is finished with a kitchen and bedroom. On the main floor, you will find 3 bedrooms, 1 full bathroom, large kitchen with dining room, living room and

    Brody Tarter RE/MAX Evolve

    2105 N 100 W, Winchester, IN 47394
  • /28

    $189,900

    • 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
  • /35

    $450,000

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

    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
  • /27

    $364,900

    • 4 Beds
    • 2.5 Baths
    • 2,684 Sq Ft

    4 St Mary's Cir, Winchester, IN 47394

    Step into this beautifully maintained 4-bedroom, 2.5-bath home, offering an inviting and functional layout you have to see for yourself! From the moment you enter the foyer, you’ll appreciate the thoughtful design, including a dedicated office space and a bright and airy sunroom—perfect for relaxing or entertaining. The master suite provides a private retreat with a stand alone bathtub and

    Paul Faddis Tarter Realty, Auction & Appraisals Co

    4 St Mary's Cir, Winchester, IN 47394
  • /16

    $159,900

    • 2 Beds
    • 1 Bath
    • 1,636 Sq Ft

    627 S Main St, Winchester, IN 47394

    This beautifully remodeled 2-bedroom, 1-bathroom home offers a perfect blend of classic charm and modern upgrades. Fresh paint and new flooring run throughout the home, creating a clean and inviting atmosphere. The layout includes both a comfortable living room and an adjacent family room, providing flexible space for relaxing or entertaining. The spacious kitchen features plenty of room for

    Paul Faddis Tarter Realty Auction and Appraisal Company

    627 S Main St, Winchester, IN 47394
  • /19

    $129,900

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

    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
  • /19

    $159,900

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

    326 S Meridian St, Winchester, IN 47394

    Welcome to this cozy, yet spacious 2-bedroom, 2-bathroom home in the heart of Winchester! Bursting with character and charm, this unique property features beautifully restored hardwood floors and thoughtful updates throughout. Enjoy outdoor living with a covered front porch, an open deck perfect for gatherings, and plenty of storage with a detached garage and two additional sheds. This home

    Jill Friend Tarter Realty Auction and Appraisal Company

    326 S Meridian St, Winchester, IN 47394
  • /2

    $25,750

    • Land
    • 0.26 Acre
    • $99,038 per Acre

    418 N Union St, Winchester, IN 47394

    Build your dream property in the heart of Winchester! This vacant lot offers the perfect opportunity for new construction. Conveniently located near the high school, pool and park, this lot provides easy access to everything the community has to offer. Public utilities available. Don’t miss this chance to invest in a prime area with great potential!

    Jammie Michael Tarter Realty Auction and Appraisal Company

    418 N Union St, Winchester, IN 47394
  • /16

    $89,900

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

    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
  • /19

    $87,000

    • 4 Beds
    • 1 Bath
    • 1,886 Sq Ft

    516 N Meridian St, Winchester, IN 47394

    This spacious 4-bedroom, 1-bathroom home offers endless potential for the right buyer looking to put their personal touch on a fixer-upper. Situated on a generously sized lot, this property is perfect for those who value space and opportunity. The large backyard offers room for expansion, outdoor entertaining, or gardening. Inside, you'll find a classic layout with four well-sized bedrooms,

    Jason and Sarah Wagner F.C. Tucker Company

    516 N Meridian St, Winchester, IN 47394
  • /15

    $99,900

    • 2 Beds
    • 1 Bath
    • 748 Sq Ft

    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 & Appraisals Co

    118 W Third St, Winchester, IN 47394
  • /25

    $74,500

    • 3,540 Sq Ft

    220 N Main St, Winchester, IN 47394

    This property features an 18x50 storefront commercial space, perfect for business owners or investors, featuring a convenient half-bath and great visibility for foot traffic. Upstairs, you'll find two 1-bedroom apartments, each equipped with their own kitchens and bathrooms—currently rented and generating $1400/month combined income. With dual income potential and a central location, this

    Paul Faddis Tarter Realty, Auction & Appraisals Co

    220 N Main St, Winchester, IN 47394
  • /13

    $103,900

    • 2 Beds
    • 1 Bath
    • 877 Sq Ft

    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
  • /3

    $249,900

    • 4,906 Sq Ft

    Multiple Adresses Unit See Remarks, Winchester, IN 47394

    Properties Included 803 S Beeson Winchester, IN 10050347 $79,900 216 N Vine St Muncie, IN 10050350 $99,900 1901 N Turner St Muncie, IN 10050346 $70,000

    BRIAN INGLE FC Tucker Richmond

    Multiple Adresses Unit See Remarks, Winchester, IN 47394
  • /9

    $64,900

    • 2 Beds
    • 1 Bath
    • 1,674 Sq Ft

    803 S Beeson Dr, Winchester, IN 47394

    Welcome to 803 South Beeson, Winchester, Indiana, a charming property that offers both comfort and potential. This home features two bedrooms, with two additional rooms that can be converted into bedrooms, providing flexible living space for your needs. It also includes one bathroom and boasts a nice, large backyard that is fenced in, perfect for outdoor activities and gatherings. With its

    BRIAN INGLE FC Tucker Richmond

    803 S Beeson Dr, Winchester, IN 47394
  • /3

    $349,900

    • Land
    • 3.57 Acres
    • $98,011 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 & Appraisals Co

    TBD Symmes Center Dr, Winchester, IN 47394
  • /4

    $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 +/- Are 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. Call today for more information.

    Paul Faddis Tarter Realty, Auction & Appraisals Co

    TBD Symmes Center Dr, Winchester, IN 47394
  • /3

    $32,000

    • Land
    • 0.34 Acre
    • $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
  • /2

    $35,000

    • Land
    • 0.36 Acre
    • $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
  • /2

    $339,675

    • Land
    • 19 Acres
    • $17,500 per Acre

    TBD S 300 E, Winchester, IN 47394

    Approximately 19.41 tillable acres for sale in Winchester. Whether you're expanding your farming operation or seeking an investment opportunity, this well-maintained acreage provides endless possibilities. Don't miss this chance to own quality farmland in a desirable location!

    Paul Faddis Tarter Realty Auction and Appraisal Company

    TBD S 300 E, Winchester, IN 47394

Frequently Asked Questions

What are the most popular zip codes in Winchester, IN?
The most popular zip codes in Winchester, IN include 45331, 47394, 47390, 47336 and 47371.
What are the most popular neighborhoods near Winchester, IN?
The most popular neighborhood near Winchester, IN is Ashland-Millville.
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