Winchester, OR Homes for Sale under $100,000

Set an appointment and view this beautifully updated 1500 plus sq ft double wide in Rose Terrace a 55+ community! Located on the north end of town,shopping, restaurants, easy access to I-5. Move in ready home with many upgrades. Kitchen has new dishwasher, stove & refrigerator, improved lighting (LED)has been freshly painted, luxury vinyl plank flooring, and new bathroom vanities. An accessible

Pearl Hergert Heaton eXp Realty, LLC

Build your DREAM HOME on this gorgeous property in Winchester. ***Owner willing to carry contract*** Located in the desirable Page Road neighborhood, this vacant lot provides a peaceful and secluded retreat at the end of a quiet road. Enjoy stunning views of the mountains, North Umpqua River, Umpqua Community College, and vineyards, offering a picturesque backdrop from your future home. With a

Lisa Ollivant RE/MAX Integrity

Very well-maintained 1970 single-wide manufactured home featuring two bedrooms and one full bathroom. This charming home offers a fully fenced yard and a covered deck, creating the perfect space to relax and enjoy the outdoors. Laundry hookups are available inside the home—just bring your own washer and dryer—or you can take advantage of the park's convenient laundry facilities.Recent updates

Brenda Smith Stellar Realty Northwest

Come build your dream home on this 0.68 acre lot located in an area of newer homes! This area offers close proximity to Winchester recreation, parks, river, fishing, and the college.

Neil Hummel The Neil Company Real Estate

Single-level living in a 55+ community. This 1,344 sq ft double-wide offers 3 bedrooms and 2 full baths with an open layout and a covered patio for morning coffee or watching the wildlife. A heat pump provides efficient heating and cooling year-round, and a new electric range and refrigerator stay with the home along with W/D. A moisture barrier was installed in 2024. Roof was disclosed as new by

Michelle Kohlhoff Sundance Realty LLC

Come build your dream home on this 0.47 acre lot located in an area of newer homes! This area offers close proximity to Winchester recreation, parks, river, fishing, and the college.

Neil Hummel The Neil Company Real Estate

Well-maintained 1,440 sq. ft. double-wide in the desirable Rose Terrace 55+ community featuring numerous recent updates and move-in-ready comfort. Improvements include new carpet and flooring, fresh interior and exterior paint, a new composition roof, new A/C heat pump, and an automatic backup generator system. Inside offers two spacious bedrooms and two bathrooms with generously sized rooms

Anthony Beckham Different Better Real Estate

Development opportunity within city limits in the Rocky Ridge area. R10 zoning and two lots being sold together offer flexibility for future plans. Property features mountain and city views and a location that supports long term investment potential. A practical option for buyers focused on long term investment or future build prospect.

Nataly Mattox RE/MAX Integrity

This excavated lot offers incredible views of mountains, vineyards and stunning valleys. Don't miss your opportunity to build your dream home on this developed house pad in a highly desirable neighborhood in Winchester. Seller is a licensed home builder/ contractor and would be willing to provide services. Utilities are at the street.

Karina DiStefano Lamonte Real Estate Professionals

Beautifully Maintained home situated next to a quiet cul-de-sac.Step into this light, cheerful, and move-in-ready home featuring new high-quality flooring, an updated kitchen, refreshed windows, and fresh interior paint. The spacious layout includes a generous primary bedroom with its own ensuite bath, complete with a soaking tub and separate shower for added comfort. The kitchen offers

Christine Drake Berkshire Hathaway HomeServices Real Estate Professionals

Welcome to this all-ages family community, known for its strong sense of community and long-term residents. This home features numerous upgrades throughout, including brand-new front and back porches/decks. Relax on the inviting front porch with your morning coffee or unwind at the end of the day in your updated outdoor space.Don't miss the opportunity to make this charming home yours—schedule

Emily McCurry Safari Village Real Estate

Build a dream home or place a large mobile home on this lot that offers you plenty of room located right in the middle of the city and surrounded by other well-kept homes. A rare opportunity to even subdivide with city approvals. Zoned residential, 7500 sqft lots with utilities close by. Amazing views of Roseburg, mountains, and valley floor.

Neil Hummel The Neil Company Real Estate

Come build your dream home on this 0.59 acre lot located in an area of newer homes! This area offers close proximity to Winchester recreation, parks, river, fishing, and the college.

Neil Hummel The Neil Company Real Estate

Enjoy peaceful, easy living in this 2-bedroom, 1-bath home in a great 55+ park. Inside there is a nice woodstove to keep you cozy in the winters. The large covered deck is the perfect spot for morning coffee or evening relaxation. A lot of potential with this one!

Karissa Pangelina Keller Williams Southern Oregon-Umpqua Valley

Great view lot with fantastic views of Roseburg Airport, Garden Valley and surrounding area! Wonderful lot to build your forever home on. Located in a very nice gated, 55+ community. Come see this one of a kind property!

Roger Snyder Berkshire Hathaway HomeServices Real Estate Professionals

Come build your dream home on this 0.46 acre lot located in an area of newer homes! This area offers close proximity to Winchester recreation, parks, river, fishing, and the college.

Neil Hummel The Neil Company Real Estate

Come build your dream home on this 0.37 acre lot located in an area of newer homes! This area offers close proximity to Winchester recreation, parks, river, fishing, and the college.

Neil Hummel The Neil Company Real Estate

Enjoy stunning views of the West Hills of Roseburg from this peaceful lot located on a quiet, dead-end city street. Offering both privacy and convenience, the property is just minutes from cinemas, dining, medical offices, and other local amenities. The lot has been excavated and is ready for construction, making it an ideal setting to build your dream home. Beautifully rocked and well-prepared,

Cheyanne Boen Windermere Van Vleet & Associates

This well-cared-for 3 bedroom, 2 full bath home is located in the desirable Rose Terrace community for residents 55 and over. Enjoy a peaceful setting with convenient access to shopping, medical services, and all the amenities of the beautiful Umpqua Valley. I. Forced air heat with air conditioning will keep you comfortable year round. Kitchen appliances, plus washer and dryer are included!

Shane Mast Oregon Life Homes