Jackson Co: Ashland Homes with Trees/Woods View

Welcome to Ashland, Oregon, a picturesque gem nestled in the heart of Jackson County. Known for its vibrant arts scene, stunning natural landscapes, and a welcoming community, Ashland offers an unparalleled lifestyle for those seeking a serene yet culturally rich environment.

Imagine waking up every morning to the gentle rustle of leaves and the whisper of the wind through the trees. Homes in Ashland with breathtaking views of trees and wooded landscapes provide a unique sanctuary that seamlessly blends comfort with nature. These properties often feature expansive windows that invite the outdoors in, allowing you to bask in the beauty of Oregon's diverse flora from the comfort of your living room.

Ashland is not just about beautiful homes; it’s a community that thrives on creativity and connection. The renowned Oregon Shakespeare Festival draws visitors from around the world, making the town a cultural hub. With charming downtown boutiques, delightful eateries, and a calendar full of local events, there’s always something to explore.

Outdoor enthusiasts will find their paradise here, with access to hiking trails, parks, and the stunning Ashland Creek. Whether you’re strolling through Lithia Park or enjoying a quiet evening at home surrounded by towering trees, Ashland offers a lifestyle that harmonizes relaxation and adventure.

If you're looking for a home that offers both tranquility and the vibrancy of community life, Ashland, with its enchanting wooded views, is the perfect place to plant your roots. Come discover the beauty and charm of Ashland, where every day feels like a retreat!

Newest Jackson Co: Ashland Homes with Trees/Woods View

$1,080,000

3 Beds ⋅ 2 Baths ⋅ 221762307 MLS

Set privately back on 5+ acres in the Sunny Oaks community, this custom 3 bed + office, 2.5 bath, 2644 sq ft home pairs open mountain views with easy access to town -- 15 min from Downtown Ashland and near Emigrant Lake. The groundwork for comfortable rural living is in place: a dedicated 1-gigabit fiber line, 300 amp electrical, whole-home water filtration, 2021 Lennox HVAC, irrigation rights, a large cedar-fenced area, and a roof under six years old. Inside, natural light fills an updated kitchen with quartz counters and hardwood floors, opening to a great room, with a separate family room, office, and laundry on the main level. Upstairs, the primary suite offers vaulted ceilings and a balcony framing the same sweeping mountain views as the wraparound deck below, plus two more bedrooms and a full bath. Outside, a gravel RV pad offers water, power, and internet, and a barn with corrals stands ready for horses. With over $200K in updates, the property is move-in ready.

7130 HIGHWAY 66, Ashland

$1,650,000

5 Beds ⋅ 3 Baths ⋅ 444414247 MLS

Addressed as 309 and 311 Granite Street, this exceptional estate is tucked above Lithia Park on nearly six private acres, blending timeless European elegance with the tranquility of a forested retreat. Surrounded by mature trees, stone pathways, outdoor patios, and serene water features, the property feels secluded and intentional, yet remains just minutes from downtown Ashland, the Oregon Shakespeare Festival, and the historic Ashland Plaza.Inside, the architecture immediately impresses with vaulted ceilings, dramatic wood craftsmanship, custom detailing, stained glass accents, and expansive windows that fill the home with natural light. Rich textures and thoughtful design elements create a warm, old-world atmosphere that is both grand and inviting.The main residence is centered around a generous open great room with a striking rock fireplace, flowing into an informal dining area and an oversized kitchen ideal for gathering. Multiple living spaces—including a formal dining room, den, and additional sitting rooms—allow flexibility for everyday living or entertaining on a larger scale.The primary residence offers 4,479 square feet, plus 2,364 square feet of flexible ground-level space. A second residence provides 844 square feet for guests or extended living, along with a separate 1,153 square foot multi-purpose room and carport. In total, the estate encompasses approximately 8,840 square feet of versatile living space.Ideally located near Mt. Ashland Ski Resort, Crater Lake National Park, the Britt Music & Arts Festival, and Rogue Valley wineries, this is a rare opportunity to own a private, architectural estate that seamlessly blends refined craftsmanship, natural beauty, and an exceptional cultural lifestyle.

309 GRANITE ST, Ashland

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