Ashland Oregon homes for sale starting at Fifty Thousand Dollars

$1,475,000 - Ashland, OR

988 Dead Indian Memorial Road Ashland, OR - Rare Ashland opportunity on a 5+ acre tax lot, close proximity to town, only 2 miles up DIMR. This stunning open concept home, is over 4,668 sq ft with 3 bedrooms & 3 full bathrooms. Innovative design w/ radius walls, stucco exterior & perfect window placement. Rustic maple hardwood cabinets, trim & flooring. The dream kitchen has a Wolf cooktop, double ovens, full freezer/fridge combo, two sinks, & granite counters. Travertine, granite & marble adorn the entry. Main level master w/ large walk-in closet, serene bath w/ double head shower & corner tub. There is a second living area on the main floor. 360-degree views from the tower room, perfect for a home office. The wine cellar and bonus rec room downstairs complete the house. Single car garage + detached RV shop. Views of Mt. Ashland, Pompadour Bluff & the Ashland city lights. The landscaping is nothing short of a dream w/ raised beds, mature trees, sitting areas and more. Don't miss the creek frontage.

$1,449,999 - Ashland, OR

451 E Ashland Lane Ashland, OR - Your Dream Country Escape Awaits!Have you ever dreamed of country living? Your very own ''Green Acres'' Mini Ranch is ready for you! This sought-after 4,100 sq. ft. single-level country home sits on 5 level, irrigated acres, offering endless possibilities-think vineyard, horse property, or a private retreat just minutes from Downtown Ashland, the world-famous Shakespearean Theatre, Immigrant Lake, and a world-class ski resort and just minutes from Downtown Ashland, the world-famous Shakespearean Theatre, ✨ Why You'll Love It: ✅ Breathtaking 360 Views - Enjoy stunning panoramic views of Mt. Ashland from your spacious vaulted-ceiling living room.✅ Versatile & Spacious - Ideal for a large family home, two-family setup, Airbnb, or home business with multiple office spaces✅ Luxury Features - Contemporary remodeled kitchen with granite counters, new cabinets, & wood laminate floors. ✅ High-Production Well - 100+ GPM per well log. Ashland Lane Website - Must See Video Tour!!

$1,375,000 - Ashland, OR

1694 Old Siskiyou Highway Ashland, OR - Welcome to 1694 Old SiskiyouTucked into 22 gated acres just minutes south of Ashland, Oregon, this exceptional estate offers a rare mix of luxury, privacy, and natural beauty. Framed by mature forest and mountain views, the property includes a custom-designed home using ICF & SIPs construction, a newly built 5,000+ square foot shop, and carefully landscaped grounds that invite both relaxation and exploration. Whether you're seeking a peaceful retreat or a base for adventure, this is a home that lives in harmony with its surroundings.Designed for Comfort and Elegance Step into the 3,206-square-foot custom home and you're greeted by a bright two-story foyer with soaring ceilings and a striking Tulikivi soapstone woodstove—both functional and visually stunning. Natural light pours in from every direction, and views of the lush backyard are visible the moment you walk through the door. To one side, a formal dining room with coffered ceilings and an arched entryway offers a refined setting for entertaining. The kitchen, warm and modern, features rich wood cabinetry with zebra wood accents, stainless steel appliances including a Wolf gas cooktop and double ovens, and a spacious island with bar seating. A large walk-in pantry adds practical storage, while the sunny breakfast nook makes everyday dining feel special. Nearby, a utility space with laundry, mudroom, and half bath keeps everything organized and convenient. The living room is inviting and filled with eastern light, perfectly framing views of the forested landscape and distant mountains—ideal for quiet mornings or cozy evenings. The main-level bedroom offers wonderful flexibility, whether used as a guest suite, secondary primary, or space for multi-generational living. It features a generous walk-in closet and easy access to a full bath just across the hall. Upstairs, an open balcony landing overlooks the foyer and features custom built-ins and wrought iron detailing. The primary suite is a serene escape, with vaulted ceilings, large windows, a walk-in closet, and a spa-style bathroom complete with tile flooring, a walk-in shower, and a soaking tub. Two additional upstairs bedrooms share a well-appointed guest bath, while a second full laundry room adds convenience for busy households or long-term guests. New Shop The newly constructed shop spans over 5,000 square feet and offers unmatched versatility. Clean and modern in design, the space includes multiple overhead doors—including full pull-through bays—making it ideal for vehicle storage, a workshop, gym, or creative studio. Whether you're restoring classic cars, building furniture, or launching your next project, this space is ready to support any endeavor. Outdoor Living Step outside to a large deck, hot tub, and beautifully landscaped backyard, protected by a deer fence and surrounded by mature trees. Raised garden beds offer space for homegrown produce or flowers, and the gentle sound of Slide Creek flowing through over 900 feet of the property adds to the sense of peace. A charming footbridge crosses the creek, leading to the southern portion of the property where an open oak savannah invites hiking, wildlife watching, or simple solitude. The entire forested area has undergone fuels reduction to promote healthy growth and reduce wildfire risk, creating a safe and sustainable natural environment. A Rare Balance of Seclusion and Access While the home feels secluded and peaceful, it's just a short drive to Ashland’s lively downtown—home to the Oregon Shakespeare Festival, award-winning restaurants, art galleries, and boutique shopping. Outdoor enthusiasts will love the proximity to world-class recreation, including over 50 miles of mountain biking and hiking trails, the Pacific Crest Trail, and Mount Ashland Ski Area, which offers year-round adventure. 1694 Old Siskiyou is more than a home—it’s a thoughtfully curated lifestyle property where luxury, craftsmanship, and natural beauty come together. Whether you’re drawn to its peaceful setting, incredible versatility, or proximity to culture and recreation, this estate offers a truly rare opportunity to live well, inside and out.

$1,350,000 - Ashland, OR

5631 Old Highway 99 Ashland, OR - This meticulously maintained private 20.9 acre estate features an elegant main house with majestic views from every room, original oak and reclaimed oak barnwood floors, mature landscaping, a large sprawling lawn area and an outdoor guest bathroom. The attached 2 car garage is insulated and finished with windows and shelving. The property includes an 1,800 sq ft. barndominium, a deer fenced garden, firewood storage custom built from logs off the land, six outbuildings, a large pasture and horse shelter, and a magnificent arena and round pen. In your own private park enjoy the lovely walking/riding paths that wind through meadows, a conifer forest over a seasonal pond and into a large oak savannah where you can lose yourself in the beauty of nature. In the main house the master bedroom has a lovely screened-in porch, the upstairs bedroom has inspiring views of the land and sky with a separate staircase entrance. Come experience the joy and peace this property offers.

$1,300,000 - Ashland, OR

2570 Siskiyou Boulevard Ashland, OR - Exquisite estate on 3.4 irrigated acres with manicured grounds, pasture, and multiple outbuildings. The single-level, 3014 sf home features 3 bedrooms + study, and 3 baths with gorgeous mosaic tile. The spacious kitchen boasts leathered granite, antique glass-front cabinets, center island, gas range, and large pantry. Enjoy hardwood floors throughout, gas fireplace, and energy-efficient Mitsubishi mini-split system. The elegant primary suite offers a light-filled sitting area, walk-in closet, and courtyard access. Outdoor living includes a pebbled-concrete courtyard with boulder water feature and fire pit, huge fenced-in garden, tons of parking space, and all the outbuildings you could need: finished barn with bathroom, studio garden workshop, storage building, detached 2-car garage with carport + office space, plus a magical tree house! Complete with gated paved entry, TID irrigation pond, RV parking and serene private rural setting with all the conveniences of being in town.

$997,000 - Ashland, OR

520 Helman Street Ashland, OR - Immerse yourself in the Lithia Creekfront lifestyle. This 2,244SF single level home features 4 bds & 1.5 bthms & an additional .36ac lot adding to the lush garden setting with room to make future dreams come true. Large picture windows bathe the great room & living area in natural light. Dining area & woodstove seamlessly connect to the fully updated kitchen. Granite countertops, stylish tile backsplash & skylight where cooking feels like a starlit affair! Spacious breakfast bar island ideal for hosting gatherings. Large laundry/mud room w/cabinets, walk-in pantry & convenient utility sink w/access to back yard. Desirable split floor plan with En suite Primary bedroom & large, lovely finished upstairs office/playroom w/open beam ceiling. Personal putting green to perfect your skills, unwind in the hot tub or explore your Zen. Nearby School, restaurants, Shakespearean Theatre & gorgeous Lithia Park

$975,000 - Ashland, OR

19015 Dead Indian Memorial Road Ashland, OR - Lovely home on beautiful Oregon Horse Property! 30+ acres surrounded by BLM and US Forestry land giving you miles and miles of riding and recreation. Located just 1 mile from Lily Glen Equestrian Park and about 5 miles from the Howard Prairie Resort. The inviting home was completely renovated in 2015 and has an open floor plan with a wrap -around covered porch. At 2624sqft with a large living room, perfect screened in porch for the summer evenings, 3 bedrooms and2 bathrooms plus a bonus room upstairs. 48 x 44 barn with stalls, access to outdoor pens, round pen and tack room. Land is fenced and cross fenced and cleared just right for your pasture and shady trees. This off the grid property is powered by a solar with new generator and batteries. The generator has an auto switch when necessary. This home will come furnished! The climate provides for solar power year round! Don't miss out of the Oregon Equestrian Dream this property provides!

$974,900 - Ashland, OR

3729 Old Hwy 99 Ashland, OR - Private retreat at 3729 Old Hwy 99 S, Ashland. A 3-bed, 3.5-bath, 3,713-sqft contemporary home on 32.44 gated acres. Just 10 min from Ashland's shops, this secluded estate, with a tree-lined drive and gated entry, ensures privacy and epic views of Emigrant Lake and surrounding peaks. The front door opens to a grand living room with vaulted ceilings, wide plank hickory floors, and a floor-to-ceiling rock fireplace. The open-concept kitchen boasts double ovens, a new fridge, granite counters, and a cooktop island, perfect for gatherings. Over $145,000 in updates in the last 2 years, including new carpet, a refinished driveway, and more, offer move-in-ready ease. The primary suite, with a spa-like bath and fireplace, looks out to the scenery. Each bdrm provides space and views. A wrap-around deck and waterfall water feature create an outdoor oasis. 32 acres invite exploration under starry skies. With a 3-car garage and strong well. Don't miss out on this beautiful place to call home.

$969,000 - Ashland, OR

961 Pinecrest Terrace Ashland, OR - New single-level Earth Advantage certified home in the Ashland hills. This contemporary home offers 2005 sqft, 4 bedrooms, 2 full bathrooms, light & bright open great room with vaulted ceilings, gas fireplace, and access to covered patio. The spacious kitchen boasts a center island, breakfast bar, large pantry, gas range & hood, and stainless steel appliances. The primary bedroom suite boasts walk-in closet, double vanity & oversized tiled shower. Highly-reputable builder of over 400 homes in the valley, Suncrest Homes, offers top quality craftsmanship, efficiency and amenities including quartz countertops, tile floors/shower, luxury laminate floors, mini-split heating/cooling system and more. Nearly 1/3 of an acre, this lovely lot has mature trees and gorgeous views and is tucked away nestled within other high-end homes.

$900,000 - Ashland, OR

2809 Dead Indian Memorial Rd Ashland, OR - Experience refined country living on just over 23 acres of rolling green hills, and panoramic mountain views. Immaculately maintained, this exceptional home welcomes you with a wide covered porch, perfect for taking in serene vistas from sunrise to sunset. Inside, beautiful hardwood floors flow throughout the open-concept design. The vaulted great room features a striking fireplace and expansive windows that bring the outdoors in. The gourmet kitchen is a showpiece, complete with sleek granite countertops, an island with seating, stainless steel appliances, and seamless flow to the formal dining room, which shows off custom built-in cabinetry and a door to the patio for effortless indoor-outdoor entertaining. The spacious primary suite is thoughtfully placed at one end of the home, featuring a walk-in closet, luxurious bath with double sinks and walk-in shower, a door to the back patio, plus a private exercise room. Two additional bedrooms and a full bath with a jetted tub and shower are located at the opposite end for privacy and comfort. A dedicated office with custom built-ins and a fully equipped laundry room with sink and storage add everyday convenience. The oversized two-car garage includes a workspace and half bath, with an adjacent mudroom entry. A designated RV parking area with hookups enhances the property’s versatility. Outside, enjoy a covered patio, manicured garden areas, and a full sprinkler system, all set against a backdrop of nature’s finest. This is a rare opportunity to own a peaceful retreat that’s just minutes from hiking trails, dining, 2 wineries, and Emigrant Lake County Park for camping, fishing, and swimming. Just 8 minutes from the shopping center. A true slice of paradise without sacrificing proximity to modern amenities.

Ashland, Oregon listings for sale

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