Winchester Homes with Contemporary Style

Welcome to Winchester, Oregon – a hidden gem nestled in the heart of Douglas County. This charming city is known for its stunning natural beauty, friendly community, and a lifestyle that perfectly balances tranquility with convenience. With the majestic Umpqua River flowing nearby and the picturesque landscapes of the surrounding mountains, Winchester offers a serene escape for nature lovers and outdoor enthusiasts alike.

One of the most exciting aspects of Winchester is its diverse real estate market, particularly the contemporary-style homes that are gaining popularity among buyers. These residences feature sleek designs, open floor plans, and an abundance of natural light, making them ideal for modern living. With clean lines and innovative architecture, contemporary homes in Winchester provide a fresh, stylish aesthetic that appeals to a wide range of tastes.

Imagine coming home to a contemporary oasis, where you can unwind in spacious living areas, entertain friends in chic kitchens, and enjoy the beauty of the outdoors from expansive windows or inviting patios. Many of these homes are thoughtfully situated to take advantage of Winchester's stunning views, allowing you to bask in the beauty of nature right from your doorstep.

In addition to its beautiful homes, Winchester boasts a close-knit community atmosphere, excellent schools, and easy access to local amenities, making it an ideal place for families and individuals alike. Whether you’re seeking adventure or relaxation, Winchester, Oregon, offers a vibrant lifestyle that you’ll love coming home to. Explore the contemporary homes available in this enchanting city and discover your perfect sanctuary today!

Newest Winchester Homes with Contemporary Style

$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

$519,900

3 Beds ⋅ 2 Baths ⋅ 190207928 MLS

Lower taxes in the Winchester area, outside the city limits! Home is all on one level! This quality-crafted home offers comfort, space, and exceptional curb appeal on a large corner lot. Featuring 3 bedrooms and 2 bathrooms, the thoughtfully designed floor plan combines functionality with timeless style. Inside, you’ll find soaring high ceilings that create an airy, inviting atmosphere, along with a dedicated office behind elegant French doors — perfect for working from home or a quiet retreat. The spacious kitchen offers abundant cabinetry, a convenient eating bar, and flows seamlessly into both the formal dining room and a cozy breakfast nook for everyday living. The private primary ensuite is designed for relaxation with granite countertops, double sinks, and a generous walk-in closet. Outside, the beautifully landscaped yard is filled with mature plantings and trees, creating a peaceful setting to enjoy from the covered rear patio. A circular driveway provides easy access and impressive curb appeal, while the private RV parking tucked behind the home offers added convenience and flexibility. A storage shed adds extra room for tools, hobbies, or seasonal storage. New roof in 2025. This well-appointed property combines comfort, privacy, and charm in one of Winchester’s desirable, most sought-after locations.

147 WINGFOOT CT, Winchester

$415,000

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. Move in ready!

260 VILLAGE DR, Winchester

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