Winchester, OR Homes for Sale with Pool

/48
$600,000

$100K PRICE DROP
- 3 Beds
- 2 Baths
- 2,400 Sq Ft
1381 Oak Hill Rd, Roseburg, OR 97471

Tucked away on 3.28 acres of lush, park-like grounds, this one-of-a-kind Oregon retreat offers something increasingly difficult to find: privacy, space, and a setting that feels worlds away, all just minutes from town. The property itself is the experience. Wander beneath mature trees to the tranquil pond, gather around the firepit or relax in the gazebo overlooking the water. Multiple outdoor

Nick Shivers

eXp Realty, LLC

1381 Oak Hill Rd, Roseburg, OR 97471
/19
$219,000

$10K PRICE DROP
- 2 Beds
- 1.5 Baths
- 1,296 Sq Ft
11 NW Mountain View Dr, Roseburg, OR 97471

Turn-key corner-unit condo offering privacy, style, and modern updates throughout! This spacious 1,296 sq. ft. home features 2 bedrooms, 1.5 bathrooms, a large loft, and only one adjoining wall. Enjoy the convenience of a detached garage and an open-concept floor plan created through recent renovations.The beautifully remodeled kitchen has been opened to the main living area and features a large

Theresa Montoya

Vantage Point Brokers, LLC

11 NW Mountain View Dr, Roseburg, OR 97471
/48
$465,000
- 4 Beds
- 2.5 Baths
- 1,920 Sq Ft
299 Wild Fern Dr, Winchester, OR 97495

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

Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

299 Wild Fern Dr, Winchester, OR 97495
/122
$1,340,000

$250K PRICE DROP
- 4 Beds
- 4 Baths
- 4,422 Sq Ft
1025 Echo Dr, Roseburg, OR 97470

Back on market. No fault of seller or property. Clean inspections on file. Welcome to this one-of-a-kind estate offering luxury, privacy, and stunning views. Situated on landscaped grounds with fenced pasture and pond for horses, this custom home blends high-end elegance with comfort. Soaring ceilings, 12-ft wood pillars, and rich walnut floors flowing throughout. The chef's kitchen boasts custom

Jerry Norman Oregon Life Homes

1025 Echo Dr, Roseburg, OR 97470
/29
$214,000

$9K PRICE DROP
- 2 Beds
- 1.5 Baths
- 1,296 Sq Ft
17 NW Mountain View Dr, Roseburg, OR 97471

Move right into this beautifully updated Mountain View Condo offering low-maintenance living in one of Roseburg's most convenient locations. This thoughtfully refreshed 2-bedroom, 1.5-bath home features an open, light-filled floor plan with soaring vaulted ceiling, updated flooring, and a spacious loft that provides the perfect space for a home office, den, guest area, or hobby room. Recent

D'Anna Caylor RE/MAX Integrity

17 NW Mountain View Dr, Roseburg, OR 97471
/48
$949,900

$49K PRICE DROP
- 4 Beds
- 2.5 Baths
- 3,774 Sq Ft
539 Wild Fern Dr, Winchester, OR 97495

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

Jennifer Kramer RE/MAX Integrity

539 Wild Fern Dr, Winchester, OR 97495
/24
$745,000
- 3 Beds
- 2 Baths
- 1,664 Sq Ft
8017 Old Highway 99 N, Roseburg, OR 97470

Value is in the M-2 zoned land but this is a nice liveable home. Windows have been replaced, great view of surrounding area, pond, pool, outbuildings. Great potential for many uses including warehouse, manufacturing, or mini storage.

Timothy A Smith RE/MAX Integrity

8017 Old Highway 99 N, Roseburg, OR 97470

Oregon Douglas County

How to Buy a Home How to Finance a Home How to Sell a Home

In Winchester, there are currently 7 homes for sale with a pool, providing a refreshing retreat and a space for leisure. Whether it's a house for sale with a pool for those warm summer days, or a property featuring an indoor or screened-in pool for year-round enjoyment, these homes offer recreation right at home. Additionally, buyers can consider properties with access to community pools, offering a convenient space for relaxation and socializing. Whether you prefer a private pool or the convenience of a community pool, browse homes for sale with a pool in Winchester, OR and discover your ideal residence.

Winchester Types of Homes for Sale

Winchester Homes by Price

Winchester Real Estate

Search Agents in Winchester

More About Living in Winchester

Homes for Sale in Nearby Neighborhoods

Homes for Sale in Nearby Cities

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage