Winchester Homes with Custom Style

Welcome to Winchester, Oregon – a hidden gem nestled in the heart of Douglas County. Known for its breathtaking landscapes and a warm sense of community, Winchester offers a unique blend of small-town charm and natural beauty. With the majestic Umpqua River flowing nearby and the stunning foothills of the Cascade Mountains as your backdrop, this city is a haven for outdoor enthusiasts and those seeking a peaceful lifestyle.

Winchester boasts a variety of homes that reflect custom styles, catering to diverse tastes and preferences. From cozy cottages to modern masterpieces, each residence tells a story of creativity and craftsmanship. The architectural variety in this area allows homeowners to find a space that truly feels like their own. Whether you’re looking for a home with rustic charm, contemporary flair, or something in between, Winchester’s real estate market is sure to impress.

In addition to its picturesque homes, Winchester offers residents access to a plethora of recreational activities. Explore the scenic trails, enjoy fishing in the Umpqua River, or take a leisurely stroll through the local parks. The community is also rich in history, with quaint shops and eateries that invite you to experience the local culture.

Living in Winchester means embracing a lifestyle where nature and community intertwine seamlessly. With its custom-style homes and welcoming atmosphere, this city is not just a place to live; it’s a place to thrive. Come discover the magic of Winchester, where your dream home awaits amid the stunning Oregon landscape!

Newest Winchester Homes with Custom Style

$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

$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

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