Ashland Homes with Fenced Pool Features

Welcome to Ashland, Oregon—an enchanting city nestled in the picturesque Rogue Valley, renowned for its vibrant arts scene, stunning landscapes, and a welcoming community spirit. With the majestic Siskiyou Mountains as a backdrop, Ashland is not just a haven for nature lovers but also a cultural hub, famous for the Oregon Shakespeare Festival and a plethora of galleries, theaters, and festivals that celebrate creativity and diversity.

As you explore this charming town, you'll discover an array of homes that perfectly complement its unique character. Among these, properties featuring fenced pools stand out as a luxurious and practical choice for families and individuals alike. Imagine stepping out into your backyard oasis, where you can unwind in the sun or host lively gatherings with friends and family—your very own private retreat in the heart of Ashland.

Homes with fenced pool features offer the perfect blend of relaxation and security, allowing you to enjoy the beautiful Oregon weather while ensuring peace of mind for children and pets. Picture lazy summer afternoons spent poolside, or invigorating morning swims before a day of exploring the local hiking trails or enjoying a picnic in one of Ashland's many parks.

Whether you’re seeking a cozy bungalow or a spacious family home, Ashland’s real estate market has something for everyone. Embrace the charm of this vibrant community and make your dream of owning a home with a fenced pool a reality in this idyllic corner of Oregon. Come experience the best of Ashland—where culture, nature, and comfort converge.

Newest Ashland Homes with Fenced Pool Features

12800 Dead Indian Memorial Road, Ashland

$1,458,000

220230264 MLS

Discover a unique retreat center nestled in the forested mountains of Southern Oregon, just 20 minutes above Ashland in Jackson County. Located at 12800 Dead Indian Memorial Road, this expansive 40-acre property offers mountain views, wooded landscapes, open meadows, abundant wildlife, and spectacular sunrises and sunsets. The 15,000-square-foot retreat center features a Great Room for gatherings, dormitory-style accommodations, a commercial kitchen, multi-use office space, a swimming pool, and beautiful grounds to explore year-round. Multiple water storage features and a spring house add value to this exceptional property. An existing conditional use permit may offer opportunities for buyers whose intended use aligns with current approvals. Currently operating as a meditation retreat center, this property offers tremendous potential for retreats, organizational gatherings, group activities, and other retreat-style experiences.

12800 Dead Indian Memorial Road, Ashland

Listing courtesy of John L. Scott Medford.

$499,900

5 Beds ⋅ 3 Baths ⋅ 220226295 MLS

Escape to a private retreat on five level, wooded acres in the heart of the Highway 66 recreation corridor, just minutes from Howard Prairie, Hyatt Lake, and Lake of the Woods. This beautifully maintained, recently updated split-level home seamlessly blends comfort, privacy, and year-round adventure. A slate entry opens into a spacious living room featuring a bay window and a wood-burning stove insert. The home offers five bedrooms, three full baths, a formal dining area, and flexible living and family rooms--each with its own fireplace--plus a dedicated office or hobby space. The kitchen is equipped with granite countertops and tile flooring, ideal for casual meals or hosting guests. Set in a peaceful forest environment close to fishing, boating, hiking, mountain biking, and snowmobiling, this property is perfect as a primary residence, seasonal getaway, or investment property. Experience the quintessential Southern Oregon lifestyle in a serene, nature-filled setting.

12300 Oregon 66, Ashland

Listing courtesy of eXp Realty, LLC.

$12,000,000

7 Beds ⋅ 19 Baths ⋅ 220223437 MLS

Chateau at Belle Fiore is one of Oregon's most extraordinary estates. Spanning over 17,400 sqft across 4 levels, this French-inspired masterpiece offers 7 bedrooms, 19 bathrooms, and exceptional craftsmanship throughout. An elevator services all floors, including an 8,000 sqft lower level with a wine room, game room, gentleman's lounge, multiple wine bars, and expansive entertaining spaces. Premium finishes include custom cumaru flooring, granite surfaces, and intricate architectural detailing. Set on 17+ acres, including 12+ irrigated acres and a producing vineyard, the estate is ideal for private enjoyment, weddings, retreats, and special events. Exterior features include hand-chiseled golden granite, a hand-cut slate roof, custom copper gutters, dormers, and downspouts. A 2,500+ sqft carriage house, 4-car garage, prep kitchen, and grand gathering spaces complete this iconic estate. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

200 Belle Fiore Lane, Ashland

Listing courtesy of Cascade Hasson Sotheby's International Realty.

$26,000,000

7 Beds ⋅ 19 Baths ⋅ 220223434 MLS

Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is for sale for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,400+ sqft; it has four levels, 5 bedrooms, 19 bathrooms, a 4-stop elevator, vineyard, 2 bedroom 2500+ sqft carriage house, 4-car garage, resort style pool, hand-cut slate roof, custom copper detailing, and one of a kind craftsmanship throughout. ~ Separately, the Winery features a 32-acre vineyard with 14 distinguished grape varietals. The 27,000+ sqft Italian basilica-inspired facility includes tasting rooms, a ceremonial barrel room, ballroom, restaurant, outdoor dining areas, panoramic views of the Rogue Valley, and a commercial production facility with extensive refrigerated wine storage. Set on nearly 70 acres, this offering includes 49+ acres of water rights. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

200 Belle Fiore Lane, Ashland

Listing courtesy of Cascade Hasson Sotheby's International Realty.

$399,000

3 Beds ⋅ 3 Baths ⋅ 220222380 MLS

Exceptional end-unit townhome less than 1 mile from Southern Oregon University! Originally built as the developer's personal residence, this thoughtfully designed home offers approximately 30% more living space than other units in the community. Inside, you'll find rich Brazilian cherry hardwood floors, elegant Italian mosaic tile accents, new interior paint, and stainless-steel kitchen appliances. The spacious kitchen features granite countertops, abundant cabinetry, and a walk-in pantry, opening to a comfortable living area with a gas stove. The main level also includes a half bath, laundry area, and access to a private fenced patio with additional storage. Upstairs, the generous primary suite captures beautiful mountain views and offers a spa-inspired bath with dual sinks, soaking tub, walk-in shower, and two closets. A detached garage, deeded parking space, community pool, exterior maintenance, and landscaped common areas complete this outstanding property.

820 Park Street, Ashland

Listing courtesy of Windermere Van Vleet & Assoc..

$350,000

2 Beds ⋅ 2 Baths ⋅ 220214714 MLS

Thoughtfully updated Glenn Vista Estates end-unit townhome offering comfort, privacy, and flexibility. The floor plan includes a bedroom and full bath on the main level, plus an additional bedroom and bath upstairs. The kitchen and bathrooms have been tastefully updated, with a skylight that fills the space with natural light. Other recent improvements include windows, roof, siding, and a newer HVAC system. The living room features a wood-burning fireplace, currently used with an electric insert, and opens to a front deck through a large sliding door, creating a seamless indoor-outdoor feel. The downstairs bedroom opens to a private, walled-in patio. As an end unit, the home enjoys added privacy and light, along with extra storage space in the garage. Community amenities include a pool and spa, all just minutes from downtown Ashland, as well as shopping, dining, and the Oregon Shakespeare Festival.

372 Glenn Street, Ashland

Listing courtesy of Full Circle Real Estate.

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Ashland Homes with Fenced Pool Features

Newest Ashland Homes with Fenced Pool Features

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