Winchester, IN Homes for Sale under $300,000

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

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

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

2,673 sq feet open concept with 2 bathrooms! Could be an awesome home outside of Winchester! 2 furnaces. Great roof and limestone structure! Would make an awesome daycare! 765-914-8169

Jeff Hazelett Better Homes and Gardens First Realty Group

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

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

Paul Faddis Tarter Realty Auction and Appraisal Company

Welcome home to this charming and cozy 2 bedroom, 1.5 bathroom home in the heart of Winchester. This home features a large front porch perfect for enjoying this summer. Once inside you will find 1,472 sq feet of living space including a large living room that opens to an open concept kitchen and dining room. Upstairs your two bedrooms provide ample room for your family. The full bath upstairs

Taylor Huntwork Vision One Real Estate

Welcome to this charming 1.5-story home offering 1,357 square feet of comfortable living space! It features 3 bedrooms, 1 full bath, and the convenience of a main-level laundry room. Enjoy the functional layout with room to make it your own. Step outside to a back deck overlooking the spacious backyard—perfect for entertaining, relaxing, or enjoying outdoor activities. A partial basement provides

Heather Clemmons Starr Real Estate LLC

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

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

Paul Faddis Tarter Realty Auction and Appraisal Company

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

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

Miranda Martin RE/MAX Evolve

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!

Erika Rojas Trusted Realty Partners of Ind

Chloe Taflinger The Taflinger Real Estate Group

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

Doug Rector Doug Rector

Make the discovery! NEW GUTTER SYSTEM BEING INSTALLED!! 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

Shaina Chatman Austyn Avenue Real Estate