Ashland Homes with Trees/Woods View

Welcome to Ashland, Oregon – a picturesque gem nestled in the heart of Jackson County. Renowned for its vibrant arts scene, stunning landscapes, and a welcoming community, Ashland offers a unique blend of small-town charm and cultural richness. Home to the famous Oregon Shakespeare Festival, this enchanting city draws visitors and residents alike with its year-round events, outdoor adventures, and culinary delights.

One of Ashland's most captivating features is its breathtaking natural surroundings. Imagine waking up to the serene beauty of trees and woods right outside your window. Homes with trees and woods views in Ashland provide a tranquil escape from the hustle and bustle of daily life. These properties not only offer stunning vistas but also a sense of privacy and peace, allowing you to immerse yourself in nature's splendor.

Whether you're enjoying a morning coffee on your deck surrounded by towering pines or taking a leisurely stroll through the nearby trails, the connection to nature is palpable. The lush greenery and vibrant wildlife create a perfect backdrop for your everyday life, making it easy to unwind and recharge.

In Ashland, you can find a variety of homes that embrace this woodland charm, from cozy cottages to spacious family residences. Each property is a unique sanctuary, designed to enhance your lifestyle while keeping you close to the vibrant community and all the amenities the city has to offer.

Discover the allure of Ashland, where the beauty of trees and woods views awaits you! Your dream home in this enchanting city is just a step away.

Newest Ashland Homes with Trees/Woods View

$3,800,000

5 Beds ⋅ 5 Baths ⋅ 674538872 MLS

Set on 3.48 private acres just 500 ft from Lithia Park and within a 1/2 mile of downtown Ashland, 237 Granite is a rare, legacy estate inspired by the timeless design principles of Greene & Greene Architects. Showcasing over 5,700 sq ft of refined living, this 5-bedroom, 5.5-bath residence embodies the essence of the Arts and Crafts Movement with exceptional craftsmanship, rich walnut flooring throughout, and a seamless connection to its natural surroundings. The grounds are a destination unto themselves--featuring a solar-heated pool, tranquil Japanese gardens with a tea house, two waterfalls, a koi pond, and direct access to nearby hiking trails. Main-level living w/ 871 sq ft primary wing, private caretaker quarters, and a separate 676 sq ft guest cottage with 1 bed, 1 bath, 2-car garage--offering flexibility for guests or extended living. ''The Gamble House'' of Ashland, this is the largest private estate of its kind in such close proximity to the cultural and natural heart of Ashland.

237 GRANITE ST, Ashland

$950,000

3 Beds ⋅ 4 Baths ⋅ 786738387 MLS

Set among more than 37 private acres in the beautiful Siskiyou Mountains, this remarkable property offers space, privacy and versatility within easy reach of Ashland and the Rogue Valley. Mt. Ashland Ski Area, Emigrant Lake and the Pacific Crest Trail are all just minutes away, putting some of Southern Oregon’s best outdoor recreation close at hand.The thoughtfully designed main residence captures the warmth and character of its surroundings. Soaring wood-clad ceilings, exposed beams, expansive windows and a striking stone fireplace create a dramatic yet inviting great room filled with natural light. The open layout flows into a spacious gourmet kitchen with abundant cabinetry and prep space, full-size refrigerator and freezer, double ovens and a generous island—equally suited to everyday living or gathering with family and friends. A dedicated media room provides another comfortable place to relax, while geothermal heating and cooling and a hard-wired generator add year-round comfort and peace of mind. A detached four-car garage offers exceptional space for vehicles, storage and more.A substantial auxiliary building adds another dimension to the property, featuring a large finished open area, kitchen, full bath and three-car garage. With room for hobbies, recreation, a studio, workshop or a variety of other uses, the space provides tremendous flexibility to adapt to your needs.Additional features include a charming loft studio, greenhouse, garden areas and abundant water storage. Wooded acreage, natural rock outcroppings, a creek and abundant wildlife create a peaceful setting with room to explore, garden or simply enjoy the natural beauty that surrounds you.Thoughtfully designed, quality built and carefully maintained, this distinctive property combines the space and privacy of a rural setting with convenient access to Ashland, the Rogue Valley and all that Southern Oregon has to offer.

5831 OLD HIGHWAY 99, 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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