Winchester Real Estate

Welcome to Winchester, Oregon – a hidden gem nestled in the heart of Douglas County! This charming city offers a unique blend of small-town warmth and stunning natural beauty, making it an ideal place for families, retirees, and outdoor enthusiasts alike.

Surrounded by the breathtaking landscapes of the Umpqua Valley, Winchester is characterized by its picturesque views, lush greenery, and proximity to the majestic Umpqua River. Residents and visitors can enjoy a plethora of outdoor activities, from hiking and fishing to boating and camping. The nearby Umpqua National Forest provides endless opportunities for exploration, with its diverse trails and serene lakes just waiting to be discovered.

Winchester boasts a tight-knit community atmosphere, where neighbors become friends and local events bring everyone together. The city hosts various festivals and farmers' markets that showcase the region's rich agricultural heritage, allowing you to savor fresh produce and artisanal goods while mingling with fellow residents.

For those who appreciate history, Winchester is steeped in rich heritage, offering charming architecture and a sense of nostalgia. The city's convenient location also means you're just a short drive away from the vibrant city of Roseburg, where you can find shopping, dining, and entertainment options to suit every taste.

Whether you're looking to settle down or invest in a vacation home, Winchester, Oregon, is a beautiful and welcoming place to call home. Experience the tranquility, community spirit, and natural wonders that make this city truly special! Come explore Winchester – where your dream lifestyle awaits!

Newest Listings in Winchester

$500,000

3 Beds ⋅ 2 Baths ⋅ 734531126 MLS

Looking for that 3 Br., but need an office? This custom contemporary home is located on a large corner lot in a beautiful Winchester neighborhood in an excellent school district. It offers super high ceilings, a large open kitchen looking into the breakfast nook and light/bright great room, and a large formal dining room for family gatherings. You'll fall in love with the semi-private outdoor living space with covered exposed ag. patio and outdoor ceiling fan. This would be the perfect spot for that gas fire pit on the cooler days! The primary bedroom is very large and has a ceiling fan, huge walk-in closet, dual sinks with granite countertops, and a full-size walk-in shower. The split floor plan is also a plus, with two extra bedrooms of nice size. This one comes with beautiful, low-maintenance landscaping, extra parking for a small RV or boat next to the garage, and a roof that is only 2 years old! This one is worth a look! Call your agent to schedule a showing today.

147 WINGFOOT CT, Winchester

$949,900

4 Beds ⋅ 3 Baths ⋅ 790208934 MLS

Exceptional space, elevated finishes and views that never get old.This impressive Roseburg home delivers a lifestyle that's hard to duplicate. The main level opens to soaring ceilings, extensive windows and beautiful views toward the UCC vineyards and surrounding mountains, with a balcony positioned to take it all in. Inside, the details stand out: quality trim work, tile and slate flooring, granite surfaces, and a formal dining room finished with a dramatic trayed, lighted ceiling.The kitchen is designed for those who enjoy gathering, with generous workspace, granite counters and a large island with seating. The primary suite feels equally considered with a jetted tub, tiled walk-in shower, slate floors, walk-in closet and access to the laundry room. Two additional bedrooms share a Jack-and-Jill bath, with a dedicated office completing the main level.Downstairs takes entertaining to another level with a private guest suite, home theater, second kitchen with granite bar and a generous gym space too. Outside, paver walkways lead to a private covered deck, hot tub with a view and fenced lawn.And the garage is in a category of its own: four-car capacity plus a workshop and concrete walk-in storage room. The car lift stays & a whole home generator too! Add the sought-after neighborhood and Roseburg schools, and this is a home that delivers far more than impressive square footage.

239 WINCHESTER CREEK AVE, Winchester

$465,000

4 Beds ⋅ 2 Baths ⋅ 404977959 MLS

Welcome to the Wild Fern community in Winchester, where quality craftsmanship, neighborhood amenities, and a beautiful natural setting come together. This meticulously maintained 4-bedroom, 2.5-bath home showcases custom woodworking, quality finishes, and an inviting floor plan designed for comfortable everyday living and entertaining.Step outside to multiple expansive decks overlooking a peaceful backyard where seasonal Winchester Creek meanders through the property, creating a picturesque setting for relaxing and entertaining. A dedicated BBQ area makes outdoor gatherings easy while the surrounding landscape provides a wonderful connection to nature.Wild Fern residents enjoy community amenities including a swimming pool, tennis courts, and basketball court, along with miles of paved neighborhood streets ideal for walking and enjoying the surroundings. The Winchester location offers the added benefit of city services while enjoying lower county property taxes.Conveniently located near Umpqua Community College, shopping, dining, schools, and Roseburg, with nearby hiking and outdoor recreation just minutes away. This exceptional home offers a rare combination of craftsmanship, comfort, community amenities, and natural beauty in one of Winchester's most desirable neighborhoods. Schedule your private showing today!

299 WILD FERN DR, Winchester

$530,000

3 Beds ⋅ 2 Baths ⋅ 636742962 MLS

Charming and ideally located at 849 N View Dr, this home offers a seamless blend of comfort, functionality, and convenience. The thoughtfully designed layout features 3 bedrooms and 2 bathrooms with inviting living spaces bathed in natural light, creating a warm and welcoming atmosphere. Enjoy a fenced yard, sprinkler system, RV parking, and a garage, perfect for both relaxation and practicality. Nestled in a peaceful setting, yet just minutes from shopping, dining, local amenities, and major commuter routes, it combines tranquility with accessibility. Set in a highly desirable neighborhood, this property is a fantastic opportunity for both homeowners and investors—don’t miss your chance!

849 NORTH VIEW DR, Winchester

$485,000

3 Beds ⋅ 2 Baths ⋅ 176433898 MLS

Welcome to this beautifully updated residence in one of Winchester's sought-after neighborhoods. Nestled on a quiet, dead-end street with a welcoming atmosphere, this home offers the perfect blend of comfort, style, and convenience. Filled with natural light from expansive windows, the thoughtfully designed floor plan features 3 spacious bedrooms, including a luxurious primary suite with a stunning walk-in closet complete with custom built-in storage and a dedicated vanity. Quartz countertops, tiled showers, and tasteful updates throughout create a fresh, modern feel. Designed for today's lifestyle, the home also offers a versatile bonus room with French doors—ideal as a home office or potential 4th bedroom. Plus an additional flex space - perfect for a family room, game room, or media room. The well-appointed kitchen features abundant cabinetry and two pantry/storage closets. The layout of the home and living spaces, make entertaining effortless. Additional storage includes a coat closet, oversized linen closet, utility/storage room, and generous cabinetry in the laundry room. Step outside to enjoy the spacious front and backyard, offering plenty of room for gatherings, play, or simply relaxing. The garage features an epoxy-coated floor, and the attached shop provides additional workspace with a bank of cabinets or the potential to convert into a covered carport. Large driveway that can easily fit 6 vehicles. Ideal location--less than five minutes from I-5, approx 10 minutes to Umpqua Community College, and less than 1 mile from the beautiful North Umpqua River, where swimming, rafting, kayaking, and fishing can be enjoyed all summer long. If you have been searching for a move-in-ready home in a peaceful, established neighborhood with room to entertain and an unbeatable location, this Winchester gem is one you won't want to miss! Current mortgage may be assumable with a 4.25% interest rate. Motivated sellers - please bring ALL offers! Agent is owner.

339 PIONEER WAY, Winchester

$474,900

4 Beds ⋅ 3 Baths ⋅ 271779634 MLS

MULTI-FAMILY / MULTI-GENERATION LIVING POTENTIAL! Stunning custom built home in Winchester! Enjoy views of the North Umpqua River and bridge views from the large wrap-around deck. Inside features a grand great room, granite counters, an upgraded range, vinyl windows, new ductless HVAC, and built-in storage. Ideal for large or multi-family potential: downstairs offers extended living area, office, and play space. Outside, enjoy a huge yard with fruit trees, RV parking, and river access. Minutes to schools, shopping, and easy I-5 access. Schedule a tour today!

170 HURRICANE LN, Winchester

$599,900

4 Beds ⋅ 2 Baths ⋅ 277360378 MLS

This beautiful custom home is located in one of Douglas County's premier neighborhoods and there is no HOA! The all level lot is nearly 1/2 acre in size and boasts an amazing amount of parking. Bring your automobiles, RVs, boats, golf carts, trailers, or whatever you have, as there is room for all! The home's interior features a spacious kitchen with built in-oven and microwave, a downdraft gas range/oven, island, eating bar, dining nook, refrigerator with water and ice, disposal and tile flooring. The comfortable living room is centered around a classy gas fireplace and has a cathedral ceiling. The primary bedroom is good sized and has direct access to the back patio, (which would be a great place to install a hot tub), along with a bathroom with a walk-in shower, garden tub, double sink vanity and a walk-in closet. The den/office has 2 doors, with one being a french door. The family room makes a great spot to enjoy your favorite indoor activities. There is a formal dining room directly off the kitchen. The upper level is very unique and has two bedrooms. Enjoy the wonderful summer weather in the fully fenced expansive back and side yards, and on the covered patio on the rear of the home, which is accessible directly from the kitchen, making for great outdoor entertaining and living. In addition to all the parking in, and adjacent to the driveway, there is a lot of parking behind the gated fence on the right side of the home. Detached carport structure and storage shed are included. All this and low county taxes! If this sounds like a place you would enjoy calling yours, don't delay, call for a viewing appointment today!

251 MARTHA DR, Winchester

$485,000

3 Beds ⋅ 3 Baths ⋅ 668222765 MLS

Beautifully updated Winchester home with approximately $80K in recent upgrades, offering flexible living options and move-in ready comfort. This charming single-level home sits on a spacious level,lot features a fully remodeled kitchen, new fixtures throughout,new flooring throuout including hickory engineered harwood, remolded master suite, new laundry room, new ductless heating/cooling,new tankless H2o tank, and a cozy gas fireplace insert. Two bonus rooms connected by a breezeway provides an ideal office, hobby room, or flex space, or added storage room adds even more utility. The property includes a carport, ample driveway parking, and a separate garage with its own laundry. Above the garage is a fully furnished 1BD/1BA guest studio—perfect for extended family, guests, or potential rental income. The expansive fully fenced backyard offers room for gardening, play, or projects, complete with a workshop and greenhouse for year-round gardening. Additional improvements include a new roof installed in 2023 and fresh interior and exterior paint. This super-cute property offers privacy, versatility, and excellent multi-use living options in a peaceful Winchester setting. Truly move-in ready and charming.

335 PAGE RD, Winchester

$410,000

3 Beds ⋅ 2 Baths ⋅ 317509469 MLS

Top location in subdivision for view of the pond and greenbelt. Fenced with back deck. Common area tennis court, playground and walking trail. This lovely 2001 built home has vaulted ceilings, 3 bedrooms, 2 baths 1427 sq ft. Recently upgraded remodeled kitchen with breakfast nook, both baths totally remodeled, and flooring upgraded. Quartz countertops, new sink, newly painted interior. Great floor plan with spacious double garage. Sprinkler system. Seller will install new roof. Covered porch in back yard overlooking pond. Great outdoor space. Seller will replace the roof.

260 VILLAGE DR, Winchester

$34,500

733023484 MLS

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 large 1/3 acre lot, this property presents endless possibilities to design and build your dream home tailored to your preferences and lifestyle. Embrace the Oregon dream with this serene property, offering a blend of natural beauty, tranquility, and proximity to urban conveniences. Close to medical facilities, shopping centers, and schools, ensuring easy access to essential amenities and services. Also enjoy proximity to recreational activities such as hiking, boating, fishing, and camping, providing opportunities for outdoor adventures right at your doorstep. Recent boundary survey on file.

214 GRAY SQUIRREL CT, Winchester

$949,900

4 Beds ⋅ 2 Baths ⋅ 786977472 MLS

Tucked away in one of Douglas County's most desirable neighborhoods, this stunning 19th century inspired custom Haynes-built home is a true showstopper. This 3,774 sq ft residence offers 4 bedrooms, 2.5 baths on a private, beautifully landscaped .63-acre lot.Step into a grand entry with soaring ceilings extending into the living and dining rooms, highlighted by 10-inch crown molding and hardwood floors with elegant mahogany inlay. The living room features a gas fireplace, while the family room offers a cozy wood stove. Decorative ornamental plaster adds timeless character to the living room and primary suite.The chef’s kitchen is designed for both function and style, featuring granite countertops, a large butcher block island with eating bar, gas cooktop, double ovens, custom built-in refrigerator, garden window, butler’s pantry, and additional pantry. Custom cabinetry throughout is inspired by Smallbone English design. The primary suite is a private retreat with French doors to its own deck, and a luxurious bath with Italian marble, jetted tub, and walk-in shower. A dedicated office showcases beautiful woodwork, hardwood floors, and built-ins.Outside, enjoy a large entertaining deck, gazebo, potting shed, and a peaceful seasonal creek. The exterior features reclaimed brick from the historic Umpqua Hotel, adding unique character.The impressive shop includes a 5-foot pit, loft “man cave,” and half bath—perfect for hobbies or storage. Community amenities include a swimming pool and tennis court.A rare blend of craftsmanship, history, and luxury—schedule your private tour today.

539 WILD FERN DR, Winchester

$425,000

754411558 MLS

Unique Mixed-Use Opportunity in Prime Winchester Location! Discover the potential of this property zoned C3 boasting over 5000 sqft in total space, allowing for both residential and commercial use—perfect for entrepreneurs, tradespeople, or investors. Located on high-traffic Stephens Street (Old Highway 99), this versatile property offers excellent visibility and accessibility, along with ample parking for up to 16 vehicles.The home features a spacious layout, 3030 sqft with a solid, well-built structure. While the main level is currently unfinished, it offers a blank canvas ready for customization—whether you envision a comfortable residence, business offices, or a blend of both.A large shop area at 2000 sqft provides ideal space for a workshop, business operations, or additional storage, and a seasonal creek adds a touch of natural charm to the back of the property.Whether you're looking to live where you work, expand your business footprint, or invest in a flexible-use property in a growing area, this one is full of possibilities.

5565 NE STEPHENS ST, Winchester

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