Winchester Homes with Creek Waterfront

Winchester Homes with Creek Waterfront

Welcome to Winchester, Oregon—a hidden gem nestled in the heart of Douglas County. This charming city is renowned for its stunning natural beauty and a warm, welcoming community. With its picturesque landscapes and serene surroundings, Winchester offers a tranquil escape from the hustle and bustle of city life, making it an ideal place to call home.

One of the standout features of Winchester is its beautiful homes with creek waterfront. Imagine waking up to the soothing sounds of flowing water and enjoying breathtaking views right from your backyard. These properties provide a unique blend of rustic charm and modern comforts, perfect for those who appreciate nature and seek a peaceful retreat. Whether you're sipping your morning coffee on the deck or hosting friends for a summer barbecue, living by the creek transforms everyday moments into cherished memories.

Winchester is also conveniently located near outdoor recreational opportunities. The nearby Umpqua River and numerous hiking trails invite adventure enthusiasts to explore the stunning landscape, while local parks offer family-friendly activities and picnic spots. Additionally, the community's vibrant local culture is reflected in its charming shops, eateries, and events that foster a strong sense of belonging.

In Winchester, you’re not just buying a home; you’re investing in a lifestyle. With its enchanting creek waterfront properties and a community that feels like family, Winchester is a place where dreams take root and memories are made. Come discover the magic of this delightful city and find your perfect home by the water!

Newest Winchester Homes with Creek Waterfront

137 JACKS CT, Winchester
$585,000
3 Beds ⋅ 2 Baths ⋅ 223462778 MLS
Beautiful Custom-Built Home Nestled in the Woods on a desirable Cul-de-Sac. Home sits among the trees and backing to a creek, this property provides a serene setting while still being conveniently located near schools, restaurants, shopping, and everyday amenities. Thoughtfully upgraded inside and out, the home features professionally installed high-end artificial grass in the front and along the side of the home, providing a beautifully maintained look with minimal upkeep. The spacious deck is ideal for entertaining and includes a gas grill, along with steps leading to the side yard. The back area is thoughtfully enclosed with deck rails and a locking gate, creating a secure outdoor space currently designed with low-maintenance garden boxes and attractive planting beds. Near creek is natural open space with wildlife that frequently passes through. Inside, you'll find newer interior paint throughout and a spacious, inviting floor plan designed for both everyday living and entertaining. The open-concept layout features a large living and dining area, with a stunning granite countertop island providing a beautiful transition into the kitchen. The well-appointed kitchen offers abundant storage and newer stainless-steel appliances, including a refrigerator, dishwasher, and gas range. The living room is warm and inviting, featuring a gas fireplace and an abundance of windows that fill the space with beautiful natural light. All three bedrooms feature carpeting, with the oversized primary suite offering plenty of room to relax and unwind. The primary bedroom includes a generous walk-in closet complete with custom organizers. The spacious primary bathroom features tile flooring, a tile walk-in shower, deep garden tub, and a separate water closet. A convenient utility room leads directly into the oversized two-car garage with workbenches. Homes like this don't come along often—come see all that this beautiful Winchester home has to offer. You won't want to miss it!

137 JACKS CT, Winchester
539 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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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.

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