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$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

$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

$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

$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

$165,000
24035561 MLS
Opportunity awaits in Winchester! Build your private dream home on this fantastic 1.26-acre lot, perfectly situated in the heart of Winchester. Zoned RS, this property offers a versatile canvas with gently sloping terrain (no steep grades), currently featuring open grass, blackberries, and scattered trees. Adding to its charm and history, the property includes the Original Amacher Barn, built in 1935. This wood-build barn with a metal roof half, wood floor and concrete slab was originally used by the Amacher family for caring for sheep. Today, it offers exciting possibilities—buyers must perform due diligence on potential options such as converting the barn into a barndominium, adding an ADU, or incorporating it alongside a brand-new dream home. With its generous size, the land also offers plenty of room for a garden, hobby farm, or space for animals, making it an ideal spot for those seeking a balance of history, lifestyle, and future potential. Conveniently located off Hurricane Lane. Must park by Oak Tree. DO NOT park at the barn entrance or in front of any gates. DO NOT enter the barn without being accompanied by a licensed real estate agent. Buyer to perform due diligence on all aspects of the property.

PIONEER WAY, Winchester

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