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Winchester, IN Homes for Sale

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  • /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

    924 Water View 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

    919 Water View St, Winchester, IN 47394
  • /19

    $49,900

    • 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 & Appraisals Co

    713 E Short St, Winchester, IN 47394
  • /20

    $89,900

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,085 Sq Ft

    134 E Carl St, Winchester, IN 47394

    AFFORDABLE 2 bedroom, 1 bathroom home in Winchester. Attached garage, central air, and lots of recent improvements! Improvements include new flooring, paint, and countertops.

    Brody Tarter RE/MAX Evolve

    134 E Carl St, Winchester, IN 47394
  • /22

    $44,900

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 910 Sq Ft

    78 S Amanda Dr Unit Lot 18, Winchester, IN 47394

    HGTV Baby! Single wide for sale in Winchester, IN. $49,900. 78 Amanda Drive. Gutted and all new! Kids go to Ball State??? House them here!!! Flooring, insulation, walls, electrical, plumbing, bathrooms, kitchen, windows. Check this out! Owners moving. This place is amazing. No land contract. I have lenders for you on this already!!!!!! Call me 765-914-8169 Better Homes and Gardens. Lot rent is

    Jeff Hazelett Better Homes and Gardens First Realty Group

    78 S Amanda Dr Unit Lot 18, Winchester, IN 47394
  • /25

    $194,900

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

    124 Sunset Dr, Winchester, IN 47394

    This thoughtfully designed 2-bedroom, 2-bath condo offers a spacious living room that seamlessly connects to the kitchen, dining area, and private back patio—creating an open, comfortable space for everyday living. The functional layout is easy to navigate and ideal for low-maintenance living. Additional features include a 1.5-car garage with a convenient utility closet. Located in Summers

    Paul Faddis Tarter Realty Auction and Appraisal Company

    124 Sunset Dr, Winchester, IN 47394
  • /22

    $227,000

    $8K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    25 N 500 W, Winchester, IN 47394

    Character, charm, and acreage, this one has it all! This inviting 3 bedroom, 2 bathroom home offers approximately 1,200 square feet of living space and sits on nearly 3 picturesque acres. Featuring an attached 2 car garage, a partially fenced yard, and plenty of room to spread out, this property offers the ideal balance of comfort and outdoor enjoyment. Full of warmth and unique appeal, this home

    Jill Friend Tarter Realty, Auction & Appraisals Co

    25 N 500 W, Winchester, IN 47394
  • /22

    $94,900

    • 2 Beds
    • 1 Bath
    • 894 Sq Ft

    420 N West St, Winchester, IN 47394

    2BR/1BA home in Winchester featuring a welcoming front living room that flows through to the dining room and open kitchen with a laundry area. A full bath sits just off the dining room, and two connected bedrooms await upstairs. Close to town amenities and a great fit as a starter home or rental.

    Paul Faddis Tarter Realty Auction and Appraisal Company

    420 N West St, Winchester, IN 47394
  • /26

    $224,900

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,676 Sq Ft

    4 Crestwood Dr, Winchester, IN 47394

    Well-maintained brick ranch offering 2 bedrooms and 2 full bathrooms in Winchester. Recent updates include new paint, new flooring, and a new furnace installed in 2024. The home features an all-seasons room with tile flooring that opens to the back patio for warm-weather enjoyment. The family room offers large windows and flows into the living room, with multiple doorways creating an open yet

    Paul Faddis Tarter Realty Auction and Appraisal Company

    4 Crestwood Dr, Winchester, IN 47394
  • /27

    $222,555

    • 3 Beds
    • 1.5 Baths
    • 2,000 Sq Ft

    221 W South St, Winchester, IN 47394

    A rare find in the heart of Winchester. This solid brick home was built in 1900 and has been exceptionally well kept with so much character. The property boast over 2,000 sq feet with original wood finishes. Newer roof put on in the last 6 years. The basement offers additional extra space with a workshop and flexible area for storage or a cozy hangout space. Schedule your tour today!

    Austin Vandevender Coldwell Banker Lingle

    221 W South St, Winchester, IN 47394
  • /7

    $349,900

    • Land
    • 3.57 Acres
    • $97,902 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 and Appraisal Company

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

    $32,000

    • Land
    • 14,810 Sq Ft
    • $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
  • /36

    $579,900

    • 3 Beds
    • 2 Baths
    • 1,575 Sq Ft

    1027 S Huntsville Rd, Winchester, IN 47394

    Stunning new construction featuring eye-catching stone accents and a beautifully designed open layout. The welcoming entry leads into a bright open-concept living room, dining area, and kitchen equipped with all new appliances, creating an ideal space for everyday living and entertaining. Just off the kitchen, the primary suite offers scenic golf course views and a luxurious private bath complete

    Paul Faddis Tarter Realty Auction and Appraisal Company

    1027 S Huntsville Rd, Winchester, IN 47394
  • /5

    $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 +/- 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 and Appraisal Company

    TBD Symmes Center Dr, Winchester, IN 47394
  • /27

    $319,900

    $55K PRICE DROP
    • 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
  • /22

    $219,900

    • 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
  • /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
  • /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
  • /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

    $1,399,000

    • 3 Beds
    • 3.5 Baths
    • 13,680 Sq Ft

    35 N 300 W, Winchester, IN 47394

    The 2003-built home features 3 bedrooms, 3 bathrooms, a full basement, and an attached 2-car garage — providing generous living space with room to grow. A separate 2-car detached garage adds exceptional storage and flexibility for equipment, vehicles, or hobbies. Included with the property is Countryside Barkyard, a thriving, high-end pet boarding, grooming, and daycare facility built just 4

    Paul Faddis Tarter Realty Auction and Appraisal Company

    35 N 300 W, Winchester, IN 47394
  • /32

    $194,900

    • 4 Beds
    • 2 Baths
    • 1,632 Sq Ft

    809 S Pine View Ln, Winchester, IN 47394

    Beautifully updated 4-bedroom, 2-bath home in Winchester featuring modern finishes throughout. The inviting foyer opens to a spacious living room and stunning kitchen with an open-concept design, perfect for everyday living and entertaining. The main level offers two bedrooms and a full bath with a walk-in tile shower, while upstairs features a loft, two spacious bedrooms, and a second full bath

    Paul Faddis Tarter Realty Auction and Appraisal Company

    809 S Pine View Ln, Winchester, IN 47394
  • /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
  • /32

    $144,900

    • 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
  • /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
  • /20

    $109,900

    $5K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,360 Sq Ft

    958 E Short St, Winchester, IN 47394

    Nicely updated home just outside of Winchester with 3 bedrooms and 1 bathroom. Metal roof, flooring, paint, and kitchen cabinets all new. Large laundry room; small garage and storage shed. USDA, FHA and VA buyers welcome!

    Brody Tarter RE/MAX Evolve

    958 E Short St, Winchester, IN 47394
  • /21

    $89,900

    $20K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,699 Sq Ft

    218 N Jackson St, Winchester, IN 47394

    Spacious 3-4 bedroom, 1 bathroom home in Winchester! This property features large living spaces, main floor laundry, a generously sized bathroom, and a flexible layout with multiple bedroom options. Upstairs includes a bright loft area and two additional bedrooms filled with natural light. A great opportunity with plenty of space for a growing family or future updates.

    Paul Faddis Tarter Realty Auction and Appraisal Company

    218 N Jackson St, Winchester, IN 47394
  • /31

    $249,900

    • 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
  • /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
  • /35

    $234,999

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

    200 E South St, Winchester, IN 47394

    Make the discovery! 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 have been done, and care taken to

    Shaina Chatman Austyn Avenue Real Estate

    200 E South St, Winchester, IN 47394
  • /5

    $44,900

    • Land
    • 15,246 Sq Ft
    • $128,286 per Acre

    302 N Main St, Winchester, IN 47394

    Paul Faddis Tarter Realty Auction and Appraisal Company

    302 N Main St, Winchester, IN 47394

Why Live in Winchester

Winchester, Indiana, is a rural community of about 5,000 people and the seat of Randolph County. Known for its vibrant small business scene, Winchester boasts a bustling downtown district with local shops, restaurants, and essential county services anchored by the Randolph County Courthouse. U.S. Route 27 offers casual franchise eateries and a Walmart for groceries. The town is famously dubbed the "sugar cream pie capital" due to Wick’s Pies, a regional institution known for its custard-based treats. Winchester provides ample green space with nearly 100 acres, primarily in Goodrich Park, which features walking trails, playgrounds, a skate park, and a village swimming pool. For high-speed thrills, the Winchester Speedway, known as the fastest half-mile in the world, has been a local attraction since 1916. The Winchester Golf Club and the Randolph County YMCA offer additional recreational opportunities. Housing in Winchester includes early 20th-century homes and new builds, with common styles being National, bungalow, and ranch-style. The town has seen recent residential development with new subdivisions like Lakeview Park. Education is served by the Randolph Central School Corporation, which offers dual credit programs through Ivy Tech Community College. Winchester is conveniently located less than two hours from Fort Wayne and Indianapolis, with easy access to Interstate 70 and I-69. The community hosts year-round events, including the Winchester Main Street Festival and Majestic Christmas, providing residents with a variety of things to do throughout the year.

Frequently Asked Questions

What is the average home price in Winchester, IN?
Homes for sale in Winchester, IN have an average home price of $169,069.
How many homes have sold over the last 12 months in Winchester, IN?
116 homes have sold in Winchester, IN over the last 12 months.
What is the average household income in Winchester, IN?
The average household income in Winchester, IN is $76K.
What are the most popular zip codes in Winchester, IN?
The most popular zip codes in Winchester, IN include 47394, 47390, 47355, 47340 and 45390.
How much do you need to make to afford a house in Winchester?
The median home price in Winchester is $164,900. If you put a 20% down payment of $33,000 and had a 30-year fixed mortgage with an interest rate of 6.43%, your estimated principal and interest payment would be $830 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $36K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winchester is $76K.
How are the schools in Winchester, IN?
Winchester, IN has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are O.R. Baker Elementary School, Willard Elementary School and Winchester Community High School. Browse all the schools in Winchester, IN to learn more.

Home Price Trends

Median Sale Price
$146,750
Median Single Family Sale Price
$143,900
Median 2 Bedroom Sale Price
$125,000
Average Price Per Sq Ft
$104
Number of Homes for Sale
16
Last 12 months Home Sales
116
Months of Supply
1.70
Median List Price
$164,900
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
11%
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