Winchester Homes with 2 Story Style

Welcome to Winchester, Oregon, a hidden gem nestled in the heart of Douglas County. This charming city is renowned for its breathtaking landscapes, vibrant community, and rich history. With the majestic Umpqua River flowing nearby, residents enjoy an abundance of outdoor activities, from fishing and boating to hiking and birdwatching. Winchester is not just about nature; it boasts a friendly, small-town atmosphere complemented by local shops, delightful eateries, and community events that bring neighbors together.

When it comes to finding the perfect home in Winchester, you’ll discover a variety of architectural styles, but the allure of two-story homes stands out. These spacious residences often feature open floor plans, allowing for seamless flow between living spaces, making them ideal for families and entertaining guests. With multiple levels, two-story homes provide ample room for privacy and personalization, whether you’re looking for cozy nooks for reading or expansive areas for gatherings.

Imagine waking up to stunning views of the surrounding hills and lush greenery from your second-story bedroom. Many of these homes come equipped with modern amenities and beautiful outdoor spaces, perfect for enjoying the temperate Oregon climate. The combination of comfort, style, and functionality makes two-story homes in Winchester a fantastic choice for anyone looking to settle in this picturesque locale.

If you’re ready to explore the enchanting community of Winchester and find your dream two-story home, let us guide you through the process. Your new adventure awaits in this beautiful corner of Oregon!

Newest Winchester Homes with 2 Story Style

$489,500

4 Beds ⋅ 3 Baths ⋅ 271779634 MLS

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

$615,000

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

$549,000

4 Beds ⋅ 3 Baths ⋅ 414398974 MLS

Located in the highly desirable Winchester Creek community, this well-maintained 4-bedroom, 3-bath home offers approximately 2,954 sq. ft. of living space, an oversized 2-car garage, and rare neighborhood privacy. Bordered by protected open space on three sides, it enjoys a sense of separation with the sounds of Winchester Creek nearby. The exterior features stone masonry accents, mature Japanese maples, a picket-fenced lawn, and low-maintenance landscaping. Inside, the main level offers an open-concept great room with formal dining, granite countertops, hardwood and tile flooring, recessed lighting, a dedicated office, full guest bath, and a secondary bedroom for guests, nursery, or workspace. The primary suite includes a soaking tub, walk-in tile shower, and walk-in closet. Sliding doors off the kitchen open to an elevated deck overlooking greenery, extending the living area outdoors. The daylight lower level functions as a second living suite with a large family room, abundant natural light, and access to a second deck. Established honeysuckle adds seasonal color and fragrance. This level includes two bedrooms, a full bath, dedicated laundry room, and flexible space for gym, media room, hobby area, guest quarters, or additional bedroom use. With its own exterior entrance, it offers strong multigenerational living or income potential. Additional features include laundry hookups on both levels, waterproof vinyl flooring in key lower areas, a pet door, Tesla Level 2 charger on a dedicated 240V circuit, and included Samsung washer/dryer plus large-screen TV. Outdoor living includes a raised brick planter, secluded patio retreat, fenced backyard, Rain Bird drip irrigation system, and landscaped pathways. Conveniently located near the North Umpqua River, I-5, Costco, and medical facilities, this home offers space, flexibility, privacy, and low-maintenance living in one of North Roseburg’s most sought-after neighborhoods.

286 WINCHESTER CREEK AVE, Winchester

$499,000

4 Beds ⋅ 2 Baths ⋅ 152479269 MLS

Priced to sell and offering exceptional value in Winchester's sought-after Oak Valley Loop neighborhood! This beautifully maintained 4-bedroom, 2.5-bath home offers 2,581 square feet of thoughtfully designed living space, combining timeless finishes, everyday comfort, and room to grow.Step inside to soaring vaulted ceilings, rich bamboo flooring, and a warm natural gas fireplace that creates an inviting focal point in the main living area. The spacious main-level primary suite provides a private retreat, featuring a luxurious ensuite bath with a tiled walk-in shower, double vanity, relaxing jetted tub, and generous walk-in closet.Designed with both entertaining and daily living in mind, the kitchen showcases granite countertops, stainless steel appliances, under-cabinet lighting, a walk-in pantry, and an eating bar that seamlessly connects to the formal dining area. Step outside to the deck and enjoy effortless indoor-outdoor living, perfect for summer barbecues, morning coffee, or evening gatherings.Upstairs, a versatile bonus loft offers additional living space, while three generously sized bedrooms—each with its own walk-in closet—provide comfort and flexibility for family, guests, hobbies, or a home office.An extra-deep two-car garage, abundant storage throughout, fresh interior and exterior paint, and mature landscaping add to the home's appeal. The fully fenced backyard creates a private outdoor oasis, offering plenty of space to relax, garden, or play.With a Real Market Value of $593,570, this home presents an incredible opportunity to own in one of Winchester's most desirable neighborhoods. Conveniently located near schools, shopping, and recreation, 556 N View Drive delivers the perfect blend of space, quality, and value. Schedule your private tour today!

556 NORTH VIEW DR, Winchester

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