Winchester Homes with Trees/Woods View

Welcome to Winchester, Oregon – a hidden gem nestled in the heart of Douglas County! Known for its stunning natural beauty and a warm sense of community, Winchester offers a tranquil lifestyle that seamlessly blends the charm of small-town living with the splendor of the great outdoors.

One of the most captivating features of Winchester is its picturesque homes that boast breathtaking views of lush trees and serene woodlands. Imagine waking up each morning to the gentle rustle of leaves and the soothing sounds of nature right outside your window. These homes are thoughtfully designed to maximize the stunning vistas, providing residents with a daily dose of tranquility and inspiration.

The community of Winchester is rich in history and culture, with a variety of local shops, parks, and recreational activities that cater to all ages. Whether you enjoy hiking, fishing, or simply taking leisurely strolls through the scenic landscapes, Winchester has something for everyone. The nearby Umpqua River adds to the area's allure, offering opportunities for water sports and fishing, while the surrounding forests invite you to explore their hidden trails and wildlife.

Living in Winchester means embracing a lifestyle where nature is at your doorstep. The homes with trees and woods views not only provide a peaceful sanctuary but also create a perfect backdrop for family gatherings, outdoor entertaining, and personal reflection. If you’re searching for a place where you can unwind, connect with nature, and enjoy the warmth of a close-knit community, Winchester, Oregon, is the ideal destination to call home. Come discover the beauty and charm that awaits you in this enchanting corner of the Pacific Northwest!

Newest Winchester Homes with Trees/Woods View

$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

$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

$999,000

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

$55,000

23486249 MLS

Come build your dream home on this 0.47 acre lot located in an area of newer homes! This area offers close proximity to Winchester recreation, parks, river, fishing, and the college.

647 NORTH VIEW DR, Winchester

$60,000

23349905 MLS

Come build your dream home on this 0.37 acre lot located in an area of newer homes! This area offers close proximity to Winchester recreation, parks, river, fishing, and the college.

817 NORTH VIEW DR, Winchester

$56,000

23297131 MLS

Come build your dream home on this 0.59 acre lot located in an area of newer homes! This area offers close proximity to Winchester recreation, parks, river, fishing, and the college.

675 NORTH VIEW DR, Winchester

$56,000

23291436 MLS

Come build your dream home on this 0.68 acre lot located in an area of newer homes! This area offers close proximity to Winchester recreation, parks, river, fishing, and the college.

719 NORTH VIEW DR, Winchester

$55,000

23029122 MLS

Come build your dream home on this 0.46 acre lot located in an area of newer homes! This area offers close proximity to Winchester recreation, parks, river, fishing, and the college.

611 NORTH VIEW DR, Winchester

Start Your Search

The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.