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160 Timberlake Drive, Ashland
$615,000
3 Beds ⋅ 2 Baths ⋅ 220230196 MLS
A joyful canvas ready for its next chapter! Perfectly positioned at the bottom of Timberlake Drive, this property offers country living just 10 minutes from Ashland's Plaza with easy access to Mt. Ashland and other outdoor recreation. Set on gently sloping acreage bordering the TID ditch, the property includes active water rights with all infrastructure fully in place. Enjoy mountain and ridgeline views from the back deck or the large waterproof balcony off the upstairs primary bedroom. Inside, this 1966 time capsule features a unique living room layout with multiple fireplaces, large windows framing the views, generously sized bedrooms, a dedicated laundry room, plus bonus and storage rooms off the garage. The house was lovingly lived in and cared for since 1974 by the same owners. Bring your vision to embrace the original aesthetic or update to your modern tastes.

160 Timberlake Drive, Ashland

Courtesy of Gateway Real Estate

806 S Mountain Avenue, Ashland
$672,000
3 Beds ⋅ 3 Baths ⋅ 220229977 MLS
Located in such a unique location with abundant forest and wild life! This home has been loved and cared for with walk around out side paths and a gardening area. There is a back deck and the sounds of wildlife all around you. Upon entering your castle the rounded arch through the front door and open living area feel grand! as you walk through this home there is a large room with a fire place, a huge living room with a half bath. Then you can turn to the left where there is a wonderful dining space private from the kitchen. Speaking of the kitchen it is a very large with lots of storage! Also the kitchen is such a perfect working space for the chef of the home. Upstairs you will find the main bedroom with 2 other bedrooms that are very spacious! The spare full bath has the laundry room in it so you don't need to carry your laundry up and down stairs and laundry is not in the way when you come home and walk through the garage. The garage houses 2 cars come see this today!

806 S Mountain Avenue, Ashland

Courtesy of eXp Realty, LLC

800 Park Street, Ashland
$320,000
2 Beds ⋅ 2 Baths ⋅ 220229936 MLS
Light-filled and thoughtfully updated, this home offers comfortable living in a quiet neighborhood with convenient access to everything you need. Recent improvements include new LVP flooring throughout, fresh interior paint, updated lighting and plumbing fixtures, new baseboards and door trim, and a new garbage disposal. The kitchen features stainless steel appliances installed in 2024 and an under-sink water filtration system. A Samsung washer and dryer are also included for added convenience. The garage offers access to a private, lockable storage room, providing extra space for your belongings. Set back from the street, the property offers a peaceful setting while remaining close to hiking and biking trails, downtown, SOU, local restaurants, and grocery stores. Enjoy the best of convenience and quiet neighborhood living in this updated home.

800 Park Street, Ashland

Courtesy of eXp Realty, LLC

1120 S Mountain Avenue, Ashland
$1,400,000
4 Beds ⋅ 4 Baths ⋅ 220229911 MLS
Rare Opportunity: Custom Ashland Estate with Panoramic Views! First time on the market! This unique, one-owner 4-bedroom (plus bonus room/den) and 3.5-bath home spans 5,192 sq. ft. on a .43-acre lot at the top of coveted South Mountain Avenue. Designed to capture breathtaking valley and Cascade Mountain views, the home features a massive wrap-around deck perfect for outdoor living and entertaining. Inside, you'll find unmatched potential and grand living spaces. Currently undergoing updates, this property offers a rare chance for a buyer to step in and customize the final finishes to their exact taste. (Note: Listing details and finished items are subject to change as renovations progress.) Unbeatable location, incredible footprint, and views that will take your breath away--don't miss one of Ashland's most unique properties!

1120 S Mountain Avenue, Ashland

Courtesy of eXp Realty, LLC

890 Twin Pines Circle, Ashland
$489,000
3 Beds ⋅ 2 Baths ⋅ 220229757 MLS
Move-in ready home right on Oak Knoll Golf Course in Ashland! There are literally no neighbors here...surrounded by Golf Course and HOA park. Fresh and inviting with all-new interior paint and flooring throughout. The spacious, open living room offers plenty of room for entertaining, while the charming kitchen and large laundry room provide great everyday functionality. The primary suite offers a comfortable retreat, and the sun room adds a unique space to relax and enjoy the natural light. Large attached 2-car garage features a convenient golf cart door for easy access to the course. Step outside to the back patio surrounded by mature landscaping and enjoy the beautiful golf course setting. A wonderful opportunity to enjoy comfortable living with the course right outside your door!

890 Twin Pines Circle, Ashland

Courtesy of Home Quest Realty

1395 Woodland Drive, Ashland
$899,000
4 Beds ⋅ 3 Baths ⋅ 220229360 MLS
There's something special about a home that gives you room to live a little bigger. Your mornings can start with coffee on the large porch with unobstructed views of Grizzly Peak, while evenings offer the same backdrop from the large sitting room on the main level. Built in 1932 and offering 3,127 SF on a .30-acre lot, this is a home with history, personality, and plenty of room for what comes next. The main house has 3 bedrooms and 1.5 baths, while a permitted 1/1 ADU on the lower level creates a separate space for guests, family, or rental income. Beyond the house, the oversized heated two-story garage and shop is a major part of what makes this property unique. There's room for serious projects, hobbies, gear, storage, and vehicles, plus dedicated off-street RV parking. Inside, the home hasn't been updated to look like every other house on the market--and that's part of the opportunity.

1395 Woodland Drive, Ashland

Courtesy of John L Scott Ashland

2200 Lupine Drive, Ashland
$1,395,000
4 Beds ⋅ 5 Baths ⋅ 220229205 MLS
Some homes are addresses. This one was a destination. Set high in the Ashland hills, this connected double geodesic dome was the longtime home of internationally influential author Jean Houston. Inside, faceted ceilings soar overhead, pierced by triangular skylights that move light through the day. Fresh paint, restored floors, and a bold gold hearth in the great room. Below, a self-contained multi-generational suite with its own entrance, plus a 2,000 sq ft finished bonus room, once a private library. Working elevator, ramps, and accessible design throughout. Outside, a wraparound deck opens to nearly twelve acres: orchard, gardens, and matured vines on the property's own well. New septic, upgraded electrical, and completed wildfire mitigation. Bordered by BLM and protected city land, the valley views stay private and pristine. A home with a soul, ready for its next chapter.

2200 Lupine Drive, Ashland

Courtesy of RE/MAX Integrity Grants Pass

2690 Takelma Way, Ashland
$507,000
3 Beds ⋅ 2 Baths ⋅ 220229157 MLS
Welcome to this single-level, wonderfully maintained home in the highly desired Clay Creek Gardens subdivision! Move-in ready for its next owners, this home features an open-concept layout connecting the kitchen, dining, and living rooms--all filled with fantastic natural light and gorgeous Oak hardwood flooring. The kitchen includes sleek slab granite countertops and bar seating. Recent updates include fresh paint, newer appliances and water heater. From the large primary suite, step outside the slider under the charming pergola to enjoy a high fence sheltering the rear patio in privacy, with plenty of room for gardening, as well as a 500-gallon rain barrel. Complete with a spacious two-car garage and a cozy front porch, you'll also enjoy neighborhood access to multiple designated open green spaces/parks, a community garden, and walking trails!

2690 Takelma Way, Ashland

Courtesy of Ford Real Estate

380 Clay Street, Ashland
$175,000
3 Beds ⋅ 1 Baths ⋅ 220229064 MLS
Excellent opportunity to build your dream home! Conveniently located near the future site of East Main Park, this property offers the potential to create a custom home in an area positioned for future neighborhood amenities. Offered for sale via online auction. Opening bid meets reserve and will sell to the highest bidder. A 5% buyer's premium will be added to the winning bid. The property will be sold in its present ''AS IS, WHERE IS'' condition, with no financing or inspection contingencies. A large Fremont Cottonwood, designated as a Heritage Tree, provides shade and adds character to the property. Buyers should be aware that removal of the Cottonwood requires a Tree Removal Permit in accordance with City requirements. See Gov Deals for more information, disclosures, and auction terms and conditions.

380 Clay Street, Ashland

Courtesy of Bang Realty-Oregon Inc.

100 Belle Fiore Lane, Ashland
$14,000,000
3 Beds ⋅ 2 Baths ⋅ 220228854 MLS
Offered for sale for the first time ever, Belle Fiore Estate Winery is Oregon's most significant vineyard estate and event destination situated on 51+ acres, including 37+ irrigated acres and an established vineyard with 14 grape varieties. Encompassing more than 27,000 sqft, the winery features multiple tasting rooms, an elegant ballroom, a restaurant, expansive terraces, and outdoor dining areas overlooking the vineyard and valley. The production facility is designed for commercial-scale operations with 8 barrel-storage bays, refrigerated wine storage, soaring ceilings, and extensive infrastructure. Hosting more than 50,000 visitors annually, Belle Fiore is a recognized destination for wine tourism, weddings, and private events. A 13.17 acre RR-5 zoned parcel with legal homesite is included in acreage. Business assets and inventory available, subject to applicable licensing and regulatory requirements. Property may be purchased together with 200 Belle Fiore Lane, Ashland, OR 97520.

100 Belle Fiore Lane, Ashland

Courtesy of Cascade Hasson Sotheby's International Realty

295 Tolman Creek Road 7 Unit 7, Ashland
$312,000
2 Beds ⋅ 2 Baths ⋅ 220228812 MLS
Nature meets urban convenience in this ideal Ashland home! Experience treetop living in this meticulously maintained, second story, one level condo. Enjoy an abundance of natural light in this open-concept home with bright, large kitchen and a living room with direct views of Grizzly Peak. The spacious private deck provides outdoor enjoyment. The two large bedrooms offer large closets and mountain views. Both full bathrooms have shower-tub combos and plenty of cabinet space. Updates include a new HVAC system (2025) and new fire-resistant hardi-plank siding (2024). Washer, dryer, and appliances are included. There is one dedicated carport space and the newly resurfaced drive and parking areas provide guest parking. Close to restaurants, shopping, and the YMCA. Easy freeway and school access, as well.

295 Tolman Creek Road 7 Unit 7, Ashland

Courtesy of Windermere Van Vleet & Associates

1750 Crestview Drive, Ashland
$735,000
3 Beds ⋅ 3 Baths ⋅ 220228500 MLS
Impeccable views and quality updated home is ready to go! Step outside directly onto hiking trails and return to this tranquil turn-key home on the end of a dead end street! Ample parking and covered space for storage of all ski gear and all your toys, make this home a year round gem to come home to after a long day of adventure! Only 30 mins from Mt Ashland from the front door! Fully updated bathrooms, kitchen and backyard make this home completely turn-key! The expansive primary suite features a sauna, walk-in closet and private wrap-around deck. Impeccable views with an open floorplan provide ample opportunities for hosting. This rare gem of views, storage and quality upgrades is one you won't want to miss!

1750 Crestview Drive, Ashland

Courtesy of John L. Scott Medford

901 Hillview Drive, Ashland
$874,000
3 Beds ⋅ 2 Baths ⋅ 220228466 MLS
Under construction for mid-December 2026 completion, this architecturally inspired midcentury home sits off-street on a private flag lot in an established neighborhood with mature trees. Vertical-grain cedar and stucco meet clean lines and covered porches. This 3-bed, 2-bath home is light and bright with clerestory windows, 8 ft doors, and vaulted ceilings. The kitchen's large island with eating bar opens to the great room, where a fireplace with a built-in bench-and-mantel sits by a wall of windows. The primary suite offers a roll-in shower, double vanity, and walk-in closet. A rare pass-through garage links the driveway and rear alley; drive straight through in either direction. No HOA. Built by Suncrest Homes, an Ashland builder with 35+ years of experience, this Earth Advantage home is energy-efficient and exceeds code. Ask about a promo 5.125% rate with the builder's lender. Listing broker is related to the owners of Suncrest Homes, one of whom is a licensed OR real estate broker.

901 Hillview Drive, Ashland

Courtesy of Gateway Real Estate

1058 Linda Avenue, Ashland
$599,000
5 Beds ⋅ 3 Baths ⋅ 220228065 MLS
Welcome home to this spacious 5 bedroom, 3 bath multigenerational home offering approximately 3,100 square feet of comfortable living space on a roomy .23-acre lot. Thoughtfully designed with two living rooms, there's plenty of room for gathering, relaxing, or creating separate spaces for extended family. A 2-car garage provides convenient parking and storage, while the covered back deck provides space to enjoy the tranquil backyard complete with a charming fish pond; perfect for enjoying your morning coffee or unwinding at the end of the day. Located in a quiet neighborhood just minutes from everything Ashland has to offer, you're less than 10 minutes from downtown Ashland, the Oregon Shakespeare Festival, and Emigrant Lake. Come experience the space, flexibility, and peaceful setting this special home has to offer!

1058 Linda Avenue, Ashland

Courtesy of John L Scott Real Estate Grants Pass

527 Sutton Place, Ashland
$745,000
3 Beds ⋅ 3 Baths ⋅ 220227832 MLS
Delightful and lovingly maintained 3-bedroom, 2.5-bath home nestled in a desirable neighborhood with minimal through traffic. This inviting property features a covered front porch entry, an open great room- dining area designed for comfortable living and entertaining, a convenient guest bath, and a bright, sunny kitchen with a breakfast nook, abundant natural light, and direct access to a covered outdoor living space. The main-level primary ensuite offers privacy and convenience with direct access to the backyard patio. Eco-friendly bamboo and cork flooring add warmth and character, while the spacious second-floor bonus room provides flexible space for a home office, media room, playroom, or guest retreat. Enjoy beautiful landscapes, mountain views, and a private fenced backyard with a covered patio overlooking a serene common area. Complete with an attached two-car garage and situated in a wonderful neighborhood, this home offers comfort, privacy, and easy living.

527 Sutton Place, Ashland

Courtesy of Ashland Homes Real Estate Inc.

2025 Green Meadows Way, Ashland
$595,000
3 Beds ⋅ 2 Baths ⋅ 220227602 MLS
What an amazing home in this highly desirable neighborhood. You have the best curbside look on the block with low maintained manicured front and backyard. Close to the Oredson Todd Woods and surrounding Ashland trails. Featured with abundant living space for all to enjoy. A large living room with dining area, wood stove and open space that leads you to an additional enclosed sunroom to enjoy the abundant sunlight, crafts and comfortable summer evenings. Also, there is a great living room for additional entertainment. Hard wood, laminate & vinyl flooring. Both bathrooms have been recently remodeled. One bedroom has been used as an office with a long countertop working space. The primary bedroom also leads you out to a wonderful large deck. Rear deck is designed for BBQ's and entertainment. Come and enjoy this special backyard with views of the Cascades and Grizzley Peak. Just 3 miles from the Shakespeare Festival. TID water comes with this property.

2025 Green Meadows Way, Ashland

Courtesy of John L. Scott Ashland

2140 Birchwood Lane, Ashland
$410,000
2 Beds ⋅ 2 Baths ⋅ 220227463 MLS
This inviting, move-in-ready home is filled with natural light and offers a functional, comfortable layout with fresh interior paint and upgraded blinds throughout. The living room features a cozy gas fireplace and flows seamlessly into the kitchen and dining area. Brand-new, high-end stainless appliances, a stylish backsplash behind the range, and a dedicated eating area complete the kitchen. The spacious primary suite offers a generous closet and ensuite bath with a walk-in shower. A second bedroom, additional full bathroom with a tub/shower combination, and conveniently located hall laundry closet add to the thoughtful layout. Step outside to a fully fenced, low-maintenance backyard featuring a concrete patio, southwest-facing exposure, and mature trees that provide beautiful filtered light and welcome shade. A beautifully landscaped front yard with a drip irrigation system and an attached two-car garage complete this truly charming home!

2140 Birchwood Lane, Ashland

Courtesy of John L Scott Ashland

3404 Siskiyou Boulevard, Ashland
$699,000
4 Beds ⋅ 3 Baths ⋅ 220227055 MLS
Beautiful Mountain Views on 5.4 Acres ! Enjoy stunning mountain views from the spacious front deck of this beautiful 2,989 sq. ft. home situated on 5.4 acres. The open--concept upper level features large, bright windows that fill the home with natural light, creating a warm and inviting living space . This home offers 4 bedrooms and 3 bathrooms, providing plenty of room for family, guests, or a home office. Additional features include TID irrigation, a newer roof, and a newer energy--efficient heat pump for year--round comfort. The lower level has 2 bedrooms with a full bath and side access door to enter. Whether you're relaxing on the deck, entertaining in the open living area, or enjoying the privacy of your acreage, this property offers the perfect blend of space, comfort, and scenic beauty.

3404 Siskiyou Boulevard, Ashland

Courtesy of RE/MAX Platinum

830 Park Street, Ashland
$339,000
2 Beds ⋅ 2 Baths ⋅ 220226785 MLS
Step inside through the custom tile foyer and into a light-filled living room with high ceilings and a cozy free-standing gas stove. This 1234 sq ft home comes with 2 bedrooms and 1.5 baths, a convenient main level laundry space and half bath off the kitchen. The kitchen has tiled countertops with a breakfast bar, dedicated dining area, and comes equipped with all appliances. Upstairs, the primary suite has great natural light, and the large spa-like bath comes with a jetted tub, glass enclosed shower, and dual vanity sinks. A second bedroom has flexibility for guests or home office. Off the dining area enjoy your own fenced yard ideal for a small garden, or to relax. Residents also enjoy access to the community pool. HOA dues of $475/mo include $175 currently put toward a roof assesment. Dues cover exterior maintenance and repairs, landscaping, garbage service, pool maintenance, and common areas. The home also comes with a detached one-car garage. Enjoy easy Ashland living!

830 Park Street, Ashland

Courtesy of Windermere Van Vleet & Associates

738 Normal Avenue, Ashland
$322,000
2 Beds ⋅ 3 Baths ⋅ 220226663 MLS
Tucked away from the main road yet just a short distance to Southern Oregon University, this well-maintained Ashland townhome offers privacy, convenience, and a bright, functional layout. Step inside to find an abundance of natural light and an open living room on the main level, complete with a half bath and under-stair storage. The kitchen features granite countertops and stainless-steel appliances. Beautiful laminate flooring runs throughout, complemented by fresh paint and new carpet upstairs. The upper level includes two bedrooms, two full baths, a laundry area with washer and dryer included, and a versatile bonus small flex room. The primary suite offers an en-suite bath and a private deck, perfect for morning coffee or evening relaxation. A private patio extends from the dining area, and a one-car garage provides secure parking and additional storage. Ideal for students, professionals, or anyone seeking a comfortable home near campus and Ashland amenities.

738 Normal Avenue, Ashland

Courtesy of eXp Realty, LLC

197 Timberlake Drive, Ashland
$725,000
4 Beds ⋅ 4 Baths ⋅ 220226035 MLS
Private 5.5-acre mountain retreat with stunning views, gated entry, asphalt drive, and expansive paved parking, only 5 minutes to town! Perched above Emigrant Lake, this impeccably maintained 2,700 sq ft home offers flexible living: two inviting living areas (one with a cozy fireplace, the other with a wet bar and patio access), a sunlit kitchen with tile floors, granite counters & backsplash, and all appliances included. Main level features formal dining, a bedroom and 1.5 baths; upstairs the spacious primary suite with walk-in closet plus two more bedrooms, 2 full baths and larger storage room. Huge attached workshop with shelving, workbenches and 220/240A service (could be converted to ADU), plus an attached 2-car garage. Entertain or unwind on the deck with pergola and hot tub, enjoy outdoor/indoor living and private hiking trails right on the property.

197 Timberlake Drive, Ashland

Courtesy of John L Scott Ashland

690 Normal Avenue, Ashland
$324,000
3 Beds ⋅ 2 Baths ⋅ 220225712 MLS
Charming and move-in ready, this Ashland townhome is priced to sell! Set back from the street on a quiet shared drive, the inviting 3-bedroom, 1.5-bath home has been freshly repainted and features updated kitchen cabinets with modern hardware, a brand-new refrigerator, new carpeting, and a bright, clean interior. The modified single-car garage offers convenient storage access from the driveway, while the spacious interior laundry/bonus room provides added versatility. Outside, the private, fully fenced backyard includes a peaceful water feature and ample space for gardening, relaxing, and entertaining. Ideally located within walking distance of everyday amenities, the home is also just a five-minute drive from downtown Ashland's restaurants, shops, theaters, and community events. Rental units are permitted, offering flexibility for homeowners and investors alike.

690 Normal Avenue, Ashland

Courtesy of RE/MAX Platinum

923 Bellview Avenue 2 Unit 2, Ashland
$410,000
4 Beds ⋅ 2 Baths ⋅ 220225100 MLS
Great value for the sqft! Delightful 4-bed, 2-bath home tucked back off Bellview Ave in a well-located community (No HOA!). Built in 1997 and updated with a new HVAC in 2026, this home features simulated wood floors throughout and fresh interior paint. Living room with wood beamed ceiling flows into kitchen with pantry and new 2025 refrigerator and dishwasher. Private, wraparound Trex deck--perfect for morning coffee, evening grilling, or relaxed entertaining. Front and back timed sprinklers make yard care effortless. Main-level living includes a bedroom and full bath featuring quartz countertops and tile flooring. Upstairs is another full bathroom with double sinks and 3 bedrooms with vaulted ceilings--one with two conjoined rooms ideal for a cozy sitting area, dressing space, or home office. Attached single-car garage. Ideal location close to Bellview Elementary, grocery stores, public transit, restaurants and more.

923 Bellview Avenue 2 Unit 2, Ashland

Courtesy of John L Scott Ashland

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The data relating to real estate for sale on this web site comes in part from the Internet Data Display (IDX) of the Southern Oregon Multiple Listing Service. Real estate listings held by brokerage firms other than our company are marked with the IDX logo and detailed information about them includes the name of the listing brokers. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information subject to change and should be independently verified. Last updated:

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