Winchester IN Real Estate & Homes for Sale

27 Properties Found

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,627
Status:
NEW LISTING
MLS#:
202646009
Type:
Single Family
Subdivision:
Willow Ridge / Willowridge
Lot size:
0.31 Acres
Year built:
2023
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

Golf course living meets modern design in this 2023-built, 3-bedroom, 2-bath home in Winchester's Willow Ridge. Positioned along the Winchester Golf Course, this single-level home offers an open-concept layout designed for easy living. The living room, dining area, and kitchen flow together, with sliding patio doors framing views of the course, pond, and green. The primary suite features two walk-in closets, a large course-facing window, and a private bath with tile finishes and a walk-in shower. Two additional bedrooms, a full hall bath with tile flooring and walk-in shower, and an attached two-car garage complete the layout. Central air and gas furnace provide efficient heating and cooling. Modern construction, golf course views, and convenient one-level living come together in one exceptional property.

Beds:
5
Baths:
1.00
Sq.Ft.:
2,241
Status:
NEW LISTING
MLS#:
202645935
Type:
Single Family
Subdivision:
Other
Lot size:
0.33 Acres
Year built:
1900
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

Old-home charm with a lot of big updates already done. This 5-bedroom home just east of downtown Winchester has beautiful hardwood floors, original woodwork, high ceilings and large rooms that give everyone space. A lot of big ticket items are already taken care of: a new metal roof, updated electrical and replacement windows along with an updated kitchen and bathroom. You can move in and enjoy the character without the usual worries of an older home. Outside, the large covered front porch is perfect for morning coffee, summer evenings and waiving to the neighbors. Out back, a huge double lot with a privacy fence gives you room for gardening, play, pets or entertaining. Homes with this much space, character and recent work don't come along often in Winchester.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,449
Status:
NEW LISTING
MLS#:
202645415
Type:
Single Family
Subdivision:
None
Lot size:
0.17 Acres
Year built:
1900
Courtesy: Flesher Brothers Auctioneering and Real Estate Inc
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ADDITIONAL INFORMATION

Classic Winchester 2 story, 3 bedroom, 1 1/2 bathroom home on a corner lot featuring a Forced Air Gas Furnace with Central A/C (2017) Gas Water Heater owned (2016) Water Softener owned, updated vinyl windows and attached garage. Extra large main bath with free standing soaking tub and walk-in bathroom closet. 1/2 bath upstairs and 1/4 bath downstairs with stand up shower and sink by laundry room.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,264
Status:
Active
MLS#:
202645229
Type:
Single Family
Subdivision:
None
Lot size:
0.19 Acres
Year built:
1900
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

Welcome to this well maintained 3 bedroom, 1 bathroom home in Winchester! Offering a large, welcoming front porch, a conveniently attached 1 car garage with a built in workshop area, metal roof, and vinyl windows. This move in ready home is ready for its next chapter and offers a great opportunity to make it yours. Don’t miss your chance to see all it has to offer!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,384
Status:
Active
MLS#:
202644809
Type:
Single Family
Subdivision:
None
Lot size:
0.81 Acres
Year built:
1932
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

Enjoy country living just 2 miles from downtown Winchester! Situated on 0.81 acre with mature trees and a spacious yard, this 3-bedroom, 1-bath home offers a peaceful setting close to local amenities. The inviting living room features a gas stove and warm wood walls and ceilings, creating a cozy cabin feel. The spacious eat-in kitchen includes a walk-in pantry, while two bedrooms are located just off the living room. The primary bedroom features updated tile flooring, and the recently remodeled bathroom offers a beautiful tile walk-in shower. A laundry room leads to the attached 2-car garage with storage space. Outside, enjoy a quaint shed/playhouse and plenty of room to spread out. Lovingly maintained by the same family for decades, this home is ready for its next owners!

Beds:
3
Baths:
3.00
Sq.Ft.:
4,698
Status:
Active
MLS#:
202643267
Type:
Single Family
Subdivision:
None
Lot size:
10.51 Acres
Year built:
1979
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

Built in 1979 and set on 10 acres with a pond, this distinctive 3-bedroom, 2.5-bath home showcases craftsmanship and architectural character rarely found today. A fountain welcomes you at the entry, leading to a dramatic living room featuring a fireplace with a striking architectural wood detail, a statement chandelier, custom bookcases, and a solid wood railing that follows the spiral staircase to the basement. Rounded quarter-circle rooms, a character-filled kitchen with island, and a primary bathroom with dual sinks, a sunken soaking tub, and patio doors reflect the home's unmistakable 1970s design. The finished basement expands the possibilities for entertaining, featuring a full kitchen, family room with fireplace, wet bar, indoor pool, full bathroom, laundry room, and abundant storage. Access the lower level by spiral staircase or elevator. Outside, a well-maintained pole barn and horse stalls complement the property's 10-acre setting. Rich in character and designed for gathering, this one-of-a-kind property offers space, privacy, and amenities for both everyday living and memorable entertaining.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,071
Status:
Active
MLS#:
202642916
Type:
Single Family
Subdivision:
Wood Crest / Woodcrest
Lot size:
0.21 Acres
Year built:
1971
Courtesy: RE/MAX Evolve
View additional info

ADDITIONAL INFORMATION

Spacious 5-bedroom, 3-bathroom home with approximately 2,071 square feet on a comfortable lot in Winchester, IN. The generous layout offers plenty of room to spread out, with multiple bedrooms and full bathrooms that make everyday living easy for a family. Recent updates include a metal roof, vinyl siding, and some windows, adding lasting durability and curb appeal. An attached garage and fenced yard provide extra convenience and outdoor space. Central air and heat keep the home comfortable year-round.

Beds:
4
Baths:
2.00
Sq.Ft.:
4,204
Status:
Active
MLS#:
202642909
Type:
Single Family
Subdivision:
Other
Lot size:
0.19 Acres
Year built:
1915
Courtesy: RE/MAX Evolve
View additional info

ADDITIONAL INFORMATION

Charming 4-bedroom, 1.5-bathroom home full of authentic character in Winchester, IN. Step into an inviting foyer with a staircase leading upstairs to large bedrooms and a bathroom. The main level features beautiful hardwood floors and built-ins, plus a kitchen that showcases original cabinetry with thoughtful updates where they count. A four-seasons room overlooks the backyard for year-round enjoyment. Additional highlights include a detached garage, central air, and a durable standing-seam roof. Need more space? The functional basement is ready for storage, a workshop, or future finishing. This home blends classic charm with everyday practicality.

Beds:
4
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
202642246
Type:
Single Family
Subdivision:
None
Lot size:
0.2 Acres
Year built:
1900
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,582
Status:
Active
MLS#:
202641347
Type:
Single Family
Subdivision:
None
Lot size:
1.12 Acres
Year built:
1860
Courtesy: Tarter Realty Auction and Appraisal Company
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ADDITIONAL INFORMATION

Farmhouse charm meets true country living on 1.12 acres! This 3 bedroom, 1 bathroom and 1,510 sq ft home sits in a peaceful country setting with the private, wide open feel so many buyers are searching for. Two barns offer endless possibilities for livestock, hobbies, a workshop or extra storage. The farmhouse character shines throughout, with updates including PEX plumbing, vinyl plank flooring, a newer water heater and a functional layout. Space, privacy and charm all in one place!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,220
Status:
Active
MLS#:
202640104
Type:
Condo
Subdivision:
None
Year built:
2025
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

Welcome home to this thoughtfully designed 2025 built condo in Summers Pointe! This 2 bedroom, 2 full bathroom home features a spacious living area with a cozy fireplace and a den offering additional flexible space. Enjoy the convenience of a 2 car garage, generator and an open patio for relaxing outdoors. With newer construction, a comfortable layout, and low maintenance living, this home makes everyday living easy. Conveniently located near shopping, restaurants, and everyday amenities. Come take a look and see all this beautiful condo has to offer!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,428
Status:
Active
MLS#:
202638840
Type:
Single Family
Subdivision:
Summerfield
Lot size:
0.33 Acres
Year built:
2003
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

Welcome to this well-maintained 4-bedroom, 2.5-bath two-story home with an attached 2-car garage nestled in a premier Winchester cul-de-sac. The inviting foyer showcases the staircase and opens to the formal living room, kitchen, and dining area, flowing into the family room with high ceilings and a fireplace. Patio doors lead to a large composite deck, above-ground pool, and dedicated pool storage room. Upstairs features four bedrooms and two full baths, including a private primary suite with walk-in closet and en-suite bath. Three additional bedrooms each offer their own closet and easy access to the second full bath. Updates include siding, roofing, utilities, and high quality landscaping. A well-maintained home with thoughtful updates, excellent outdoor living, and a sought-after cul-de-sac setting.

Beds:
4
Baths:
2.00
Sq.Ft.:
3,726
Status:
Active
MLS#:
202637654
Type:
Single Family
Subdivision:
None
Lot size:
0.21 Acres
Year built:
1900
Courtesy: The Taflinger Real Estate Group
View additional info

ADDITIONAL INFORMATION

Two-story home offering 4 bedrooms and 1.5 baths. The property includes a detached one-car garage and offers an opportunity for renovation and improvement. Property is being sold as-is. Due to the condition of the property, buyers and agents should conduct their own due diligence regarding the condition and potential repairs.

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
202634969
Type:
Single Family
Subdivision:
None
Lot size:
0.19 Acres
Year built:
1958
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

One-story home in Winchester offering 3 bedrooms and 1.5 baths, all conveniently located on the same level. Built on a slab foundation with a gas furnace and central air for year-round comfort. A bright front living room welcomes you in, while a separate family room off the kitchen offers additional space to relax or entertain. The kitchen features a connected dining area and built-in laundry closet for everyday convenience. Attached 1-car garage provides direct access, and the fully fenced backyard, enclosed with a vinyl privacy fence - includes an attached shed for extra storage.

Beds:
5
Baths:
1.00
Sq.Ft.:
2,080
Status:
Active
MLS#:
22122351
Type:
Single Family
Subdivision:
No Subdivision
Lot size:
0.18 Acres
Year built:
1900
Courtesy: Trusted Realty Partners of Ind (317) 796-38
View additional info

ADDITIONAL INFORMATION

Attention all investors! Check out this 5 bedroom, 1 bath home in Winchester ready to be brought back to life. Over 2000 square feet and situated on a nice lot, this home offers endless potential. Don't wait, schedule your showing today!

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
202634762
Type:
Single Family
Subdivision:
None
Lot size:
9.76 Acres
Year built:
1974
Courtesy: RE/MAX Evolve
View additional info

ADDITIONAL INFORMATION

Rare opportunity awaits! This 10-acre property offers the perfect blend of country living and versatility, featuring a pond, open pasture, barn with stables and a chicken coop that was previously set up as a dog kennel and now awaits some TLC. The 3-bedroom, 1-bath home features an open-concept kitchen, dining and living area with new flooring throughout. The walk-out basement provides an attached 2-car garage for convenient access and storage. A new roof was installed in 2025. Bring your vision and make this unique property your own!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,200
Status:
Active
MLS#:
202633921
Type:
Single Family
Subdivision:
Other
Lot size:
0.17 Acres
Year built:
1949
Courtesy: RE/MAX Evolve
View additional info

ADDITIONAL INFORMATION

Welcome home to this inviting 3-bedroom, 1-bath home featuring spacious rooms and plenty of room to live and entertain. Enjoy the convenience of an attached garage, plus a fenced pet area for four-legged family members. Beautiful curb appeal welcomes you from the moment you arrive, making this a home you won’t want to miss!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,482
Status:
Active
MLS#:
202633788
Type:
Single Family
Subdivision:
South West / Southwest
Lot size:
0.17 Acres
Year built:
1959
Courtesy: Flesher Brothers Auctioneering and Real Estate Inc
View additional info

ADDITIONAL INFORMATION

Welcome to your next home with this Ranch style house offering 3 bedrooms, 2 bathrooms with over 1900 sq. ft. of living space that features an extra large master suite, a dining room and a flex room. The gas log fireplace is a functional focal point to enjoy. A spacious attached 2 car garage with built-in storage. This home is nestled between Willard school and Winchester's Gaslight addition. Bonus features include a new roof, new facia, new gutters and gutter helmet, as well as windows and flooring all installed in 2024.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,092
Status:
Active
MLS#:
202632642
Type:
Single Family
Subdivision:
None
Lot size:
0.17 Acres
Year built:
1843
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

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 laundry/utility room provides excellent storage. Outside, enjoy a generous backyard, detached 1-car garage, and additional covered storage under the attached carport.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,200
Status:
Active
MLS#:
22118565
Type:
Single Family
Subdivision:
N Meridian Place Lot
Lot size:
0.13 Acres
Year built:
2025
Courtesy: Doug Rector (765) 730-40
View additional info

ADDITIONAL INFORMATION

Discover unparalleled modern living at 528 N Meridian ST, WINCHESTER, IN. Built in 2025, this brand-new single-family residence offers 1200 square feet of thoughtfully designed living space, promising a fresh start in a vibrant community. This inviting home features two comfortable bedrooms, providing ample private retreats for relaxation and personal space. A well-appointed full bathroom serves the home, designed for both functionality and comfort. The single-story layout ensures effortless living, with all areas easily accessible and contributing to an open, integrated feel. With a generous lot size of 5767 square feet, there's ample outdoor potential to create your ideal personal haven. This is more than a home; it's an invitation to a new chapter of comfort and convenience. This home offers attached 2 car garage with opener with a epoxy floor.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,998
Status:
Active
MLS#:
202627612
Type:
Single Family
Subdivision:
None
Lot size:
0.48 Acres
Year built:
1986
Courtesy: RE/MAX Evolve
View additional info

ADDITIONAL INFORMATION

Stunning 3-bed, 2 full/2 half bath home offers over 2,000 sq ft of pure elegance. This spacious floor plan offers an abundance of natural light leading into an updated kitchen with new cabinetry, solid surface countertops. Master suite comes complete with a custom walk-in closet as well as an updated full bathroom. This home offers many features such as the on-demand hot water heater, affordable utility bills, as well as generously sized bedrooms. Situated perfectly on 1 acre with elegant landscaping, the fully fenced pool area is a private oasis with an inground pool and charming pavilion, perfect for entertaining. Conveniently located, this home offers easy access to amenities such as the walking track in short proximity, local shopping, and dining. Don't miss this opportunity to experience luxury private living with a sense of community.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,128
Status:
Active
MLS#:
202622209
Type:
Single Family
Subdivision:
None
Lot size:
0.1 Acres
Year built:
1900
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
1.00
Sq.Ft.:
834
Status:
Active
MLS#:
22106167
Type:
Single Family
Subdivision:
Southwest
Lot size:
0.12 Acres
Year built:
1900
Courtesy: Beycome Brokerage Realty LLC 8046565007
View additional info

ADDITIONAL INFORMATION

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

Beds:
3
Baths:
2.00
Sq.Ft.:
1,783
Status:
Active
MLS#:
202619600
Type:
Single Family
Subdivision:
None
Lot size:
0.23 Acres
Year built:
2026
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

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 covered porch ideal for relaxing and enjoying the outdoors. With attention to detail throughout, this home is truly move in ready. A must see!

Beds:
3
Baths:
4.00
Sq.Ft.:
15,312
Status:
Active
MLS#:
202619416
Type:
Single Family
Subdivision:
None
Lot size:
5 Acres
Year built:
2003
Courtesy: Tarter Realty Auction and Appraisal Company
View additional info

ADDITIONAL INFORMATION

Imagine waking up at home, walking to work, and building your family’s future around a business you own. Countryside Barkyard is a rare opportunity to acquire an established, high-end pet boarding, grooming and daycare business with a private residence on the same property. The purpose-built facility is fully operational, the customer base is established, and the residence provides a comfortable home base without the daily commute. For an owner-operator, this could mean greater control over your schedule, more time at home and the opportunity to involve your family in a meaningful business environment - learning responsibility, work ethic and real-world skills along the way. For the right buyer, this isn't simply a business acquisition. It's a lifestyle change. Countryside Barkyard Business + Residence $1,349,000 Confidential inquiries from serious, qualified buyers are welcome.

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Albert Wright Page, License RB14038157, Xome Inc., License RC51300094, [email protected], 844-400-XOME (9663), 4471 North Billman Estates, Shelbyville, IN 46176


Information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX information provided by the Indiana Regional MLS. Copyright 2026 Indiana Regional MLS. All rights reserved.

Albert Wright Page, License RB14038157, Xome Inc., License RC51300094, [email protected], 844-400-XOME (9663), 4471 North Billman Estates, Shelbyville, IN 46176

Listings courtesy of MIBOR as distributed by MLS GRID. Based on information submitted to the MLS GRID as of {{last updated}}. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. © 2024 Metropolitan Indianapolis Board of REALTORS®. All Rights Reserved.




Winchester Real Estate

Winchester is located in Indiana. Winchester, Indiana has a population of 5,016. Winchester is more family-centric than the surrounding county with 31.45% of the households containing married families with children. The county average for households married with children is 29.25%.

The median household income in Winchester, Indiana is $51,985. The median household income for the surrounding county is $54,912 compared to the national median of $69,021. The median age of people living in Winchester is 39.6 years.

Winchester Weather

The average high temperature in July is 83.3 degrees, with an average low temperature in January of 17.3 degrees. The average rainfall is approximately 39.1 inches per year, with 20.1 inches of snow per year.

Winchester Map

Winchester Real Estate Market Conditions

  • Median sales price

    $177,000
    15.1%
    change since last quarter
  • # Active listings

    40
    30-day change

Winchester Schools and Demographics

Education near Winchester, IN

City County
High School Graduates 88.08 89.06
College Degree - 2 year 6.78 8.08
College Degree - 4 year 14.76 16.21
Graduate Degree 4.05 4.88
Expenditures per Student 9,504 9,504
Students per Teacher 18.8 18.8

Elementary Schools near Winchester, IN

Grades Students P/T Ratio ZIP
Deerfield Elementary School KG - 05 207 13.8 47380
North Side Elementary School PK - 06 514 13.9 47390
O R Baker Elementary School PK - 02 323 17 47394
Randolph Southern Elementary School KG - 06 242 13 47355
Union Elementary School KG - 06 162 16.2 47358
Willard Elementary School 03 - 05 215 13.4 47394

Middle Schools near Winchester, IN

Grades Students P/T Ratio ZIP
Lee L Driver Middle School 06 - 08 364 15.2 47394

High Schools near Winchester, IN

Grades Students P/T Ratio ZIP
Randolph Southern Junior/Senior High School 07 - 12 241 11.5 47355
Union City Community High School 07 - 12 418 13.9 47390
Union Junior & High School 07 - 12 174 10.2 47358
Winchester Community High School 09 - 12 460 15.3 47394

Demographics near Winchester, IN

City County
Neighborhood Type Small Town
Population 5,016 24,681
Population Density 1,454 55
Median Age 39.6 42.6
People per Household 2.3 2.4
Median Household Income 51,985 54,912
Average Income per Capita 25,822 28,044

Real estate near Winchester