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616 Altamont Street, Ashland
$699,000
3 Beds ⋅ 3 Baths ⋅ 220230499 MLS
Beautifully remodeled and immaculately maintained home in sought-after downtown Ashland neighborhood with private oasis backyard and mountain views. Warm wood floors and gas fireplace create a welcoming feel to the living space, while the kitchen boasts granite counters, painted cabinetry, pantry and newer stainless-steel appliances. A thoughtful layout separates the two additional bedrooms from the primary bedroom wing which includes an office, walk-in closet and beautiful ensuite bathroom with tiled shower and clawfoot tub. The backyard is truly enchanting, featuring a koi pond and flowing water feature to be enjoyed from the grapevine-draped covered patio. The front wraparound deck is perfect for visiting or dining outside with mountain views. Modern, high-efficiency upgrades include solar panels, vinyl windows, newer HVAC, tankless water heater, and rain catchment. Detached garage offers private alley access and potential for an ADU. Turn-key and close to downtown!

616 Altamont Street, Ashland

Courtesy of John L Scott Ashland

786 Pompadour Drive, Ashland
$3,250,000
4 Beds ⋅ 6 Baths ⋅ 220230483 MLS
Seller financing now available! Paradox Vineyard Estate is uniquely defined by elements of air, water, and natural light. Senses are captivated by a soaring skylight galleria spanning through the home, open-air water courts with columnar basalt fountains, and stunning panoramic mountain views. Award-winning architecture and landscape design, exceptional workmanship, and material selections demonstrate a commitment to environmental stewardship. Tranquil outdoor spaces with mature ornamental trees, 64-foot infinity-edge lap pool and spa, berry and rose garden, block barn, 96-panel solar system, four private wells with water delivery rebuilt in 2022, expansive paver motor court, and secure gated entry. Professionally managed vineyard producing CCOF-certified organic Syrah and Chenin Blanc acclaimed by local and regional winemakers. Close-in rural community of high-end estates, just five miles from downtown Ashland. Inquire for details!

786 Pompadour Drive, Ashland

Courtesy of John L Scott Ashland

496 Beach Street, Ashland
$845,000
5 Beds ⋅ 6 Baths ⋅ 220230213 MLS
Gorgeously renovated Victorian blends historic charm with modern luxury in the heart of Ashland. R2 zoning offers versatile living: A gracious private residence, a home with Airbnb units, or a B&B with owner-occupied quarters. Once the beloved Midsummer Night's Dream B&B, it's now a private home with 2 vacation rentals in a stunning detached annex. The annex has produced income of up to $7500 a month in season. The main house (2375 SF) features hardwood floors, a lovely living room with fireplace, parlor/game room, formal dining room, chef's kitchen, laundry room, & small office. 3 luxurious suites are in the main home, with 2 more in the annex (1092 SF), each with a fireplace, spa bath, shower & a private deck. Expansive lush lawn areas with mature flowering trees & mountain views create a peaceful & picturesque setting. Unbeatable location near theaters, dining, & the magic that is Ashland. Off street parking. Inquire about purchase as turn-key operation with negotiated inclusions.

496 Beach Street, Ashland

Courtesy of Millen Property Group

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

25 S Mountain Avenue, Ashland
$439,000
3 Beds ⋅ 2 Baths ⋅ 220230127 MLS
Ideally located in Phillips Corner near the heart of Ashland, this 3-bedroom, 2-bath townhome was built with efficiency and sustainability in mined. Built to Earth Advantage standards, this home features high-efficiency, mini-split HVAC and an on-demand gas water heater. The living room has high vaulted ceilings, a gas fireplace, and an open staircase. The kitchen offers modern cabinetry, stainless steel appliances, lots of storage, and a convenient pantry. Enjoy outdoor living on the spacious, covered front porch or private back patio. A 2-car garage provides additional parking and storage. Affordable HOA dues include landscape maintenance, garbage service, and access to the community playground and garden. Just minutes from downtown Ashland, shopping, dining, entertainment, SOU, and nearby parks, this townhome offers comfortable, low-maintenance living in a convenient location.

25 S Mountain Avenue, Ashland

Courtesy of RE/MAX Platinum

1311 Neil Creek Road, Ashland
$515,000
3 Beds ⋅ 2 Baths ⋅ 220230033 MLS
Searching for a sweat equity project in rural Ashland? If so, this is the one for you! This charming single level property (needs TLC) features a spacious 3 bed, 2 bath, 2366 sq ft home that offers an open floor plan, bamboo flooring throughout, large (partially covered) deck, woodstove in the living room, 6+ wooded acres, circular driveway, multiple sheds, & much more! In addition, you also have a detached 2018 built, 2 bed, 1 bath manufactured home (very livable) that offers an open floor plan, covered deck, and chef's kitchen. Manufactured home was installed under a medical hardship as well. Buyer to perform their own due diligence pertaining to usability of the manufactured home. Perfect opportunity for a contractor looking for their next project and/or anyone that wants to get lost in the woods and enjoy the ambiance of rural Southern Oregon. This one won't last long on the market, so contact your agent today for a personal tour, before it's too late!

1311 Neil Creek Road, Ashland

Courtesy of John L. Scott Medford

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

726 Iowa Street, Ashland
$605,000
3 Beds ⋅ 2 Baths ⋅ 220229966 MLS
This charming 3 bed / 2 bath 1890 Victorian farmhouse is on a beautiful tree-lined street close to downtown Ashland. The covered front porch leads you into the 1658 sq ft home with original fir floors, high ceilings and period light fixtures. There are generous windows and skylights bringing wonderful light into the parlor, large kitchen and living room. French doors off the kitchen lead to the covered side porch and a large backyard including 4 fig trees, 10 raised beds and your own potting sunroom. The big jobs have been completed in this well maintained home- the foundation and roof were replaced in 2015. The HVAC system is new as of 2022 and ductless mini-splits were added upstairs in 2019.

726 Iowa Street, Ashland

Courtesy of Windermere Van Vleet & Associates

472 Waterline Road, Ashland
$600,000
4 Beds ⋅ 3 Baths ⋅ 220229914 MLS
Spacious home with stunning panoramic views in an established neighborhood above the boulevard near hiking and biking trails in Ashland's Lower Watershed. Vaulted great room with walls of windows and sliding glass doors to wrap-around deck, gas fireplace with river rock surround, wet bar, formal and informal dining areas with solid oak flooring, kitchen with tiled dining counter, walk-in pantry, electric cooktop and stainless appliances, main-level bedroom with walk-in closet and ensuite access to full bathroom with tiled vanity and tub shower. Lower level includes an expansive primary bedroom with wood-burning fireplace, full ensuite bath with radiant-heated tile floor, two separate vanities, tiled shower, jetted tub, and two mirrored walk-in closets; third and fourth bedrooms with deck access and walk-in closets, full guest bath with tiled tub shower, storage room, and laundry room with washer and dryer. Home is priced for ''As-Is'' sale. Inquire for details!

472 Waterline Road, Ashland

Courtesy of John L Scott Ashland

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

524 W Nevada Street, Ashland
$475,000
3 Beds ⋅ 3 Baths ⋅ 220229876 MLS
Desirable end-unit townhome with quality finishes and abundant natural light, directly adjacent to 1.77-acre community park in Billings Ranch! Main level great room with high vaulted ceiling, hardwood floors, gas fireplace, covered view balcony, kitchen with granite counters and dining island, knotty alder cabinets and built-in buffet, stainless appliances including five-burner gas range with a double oven, powder room, two-car garage, and private side-yard patio. Vaulted upper-level primary with view balcony and a full ensuite bathroom with double vanity, shower, and walk-in closet. Tiled lower entry foyer with built-in shelving and desk, full guest bath with tub shower, laundry room, and two bedrooms with shelving and sliding glass door to covered deck. All new exterior paint and updated landscaping in 2026; HVAC units replaced in 2024. Association dues cover all exterior maintenance and landscaping. Inquire for details!

524 W Nevada Street, Ashland

Courtesy of John L Scott Ashland

425 W Nevada Street, Ashland
$839,000
5 Beds ⋅ 3 Baths ⋅ 220229842 MLS
Beautiful 2018 Craftsman home in Ashland's Billings Ranch neighborhood with 5 bedrooms and 2.5 baths, backing to open space with Cascade mountain and valley views. A covered porch opens to a bright foyer and main-level office or fifth bedroom behind French doors. The vaulted great room has view windows and stacked-stone fireplace, open to dining and a kitchen with white shaker cabinetry, pantry, breakfast bar, and smart convection gas double oven plus a third oven. The main-level primary suite has patio access, dual copper sinks, soaking tub, walk-in shower, and walk-in closet. Upstairs: second living room with built-in desk, a bedroom with a second walk-in closet, additional bedrooms, and a full bath. Washer and dryer stay. Outside: xeriscaped front, fenced backyard with firewise patio, fruit trees, grape vines, raised beds, garden shed, and 4-zone smart drip/sprinkler irrigation. Extra-deep 2-car garage with storage and workbench. Nearby wetland offers great bird watching!

425 W Nevada Street, Ashland

Courtesy of John L Scott Ashland

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

827 Tyler Creek Road, Ashland
$474,900
3 Beds ⋅ 3 Baths ⋅ 220229660 MLS
Escape to a private retreat in the hills outside Ashland. Set on 5.13 wooded acres, this peaceful property feels worlds away, yet is about 20 minutes from the South Ashland I-5 exit. The distinctive 3-bedroom, 2.5-bath home offers 2,833 sq ft with forest, mountain and creek views. Radiant floors, vaulted ceilings, skylights, large windows and straw-bale insulated walls provide year-round comfort and connection to the landscape. The updated kitchen features granite counters, an island, walk-in pantry and stainless appliances, opening to living and dining areas anchored by a wood-burning fireplace. Upstairs, the spacious primary suite includes a private balcony, soaking tub and tiled shower. Two additional bedrooms offer space for family or guests. A finished lower level with exterior access is ideal for an office, studio, recreation room or guest space. Enjoy a wraparound deck, garden areas and mature trees, plus RV parking and hookup, EV charging, storage and a two-car garage.

827 Tyler Creek Road, Ashland

Courtesy of Real Broker

380 E Butler Lane, Ashland
$3,900,000
3 Beds ⋅ 3 Baths ⋅ 220229525 MLS
Turnkey cannabis production and processing facility in Ashland, OR, offered with real estate, business assets, and an adjacent 4.97-acre buildable parcel featuring homesite approval. The property includes a 5,000 SF (50' x 100') red iron building complete with office space, break room, bathroom, climate-controlled dry room, vegetative room, trim area, storage mezzanine, dedicated ice-water extraction wash room, and packaging area. Cultivation infrastructure is anchored by two 40' x 120' GrowSpan internal-deprivation mix-light greenhouses, with power supplied by two separate 800-amp single-phase electrical services (~1,400 amps dedicated to the commercial facility and ~200 amps to the residence). The existing improvements sit on a 4.97-acre parcel, combining with the neighboring lot for nearly 10 acres total with expansion potential. Included in the sale is an established brand with active Oregon-wide distribution and a proven history of indoor flower and solventless production.

380 E Butler Lane, Ashland

Courtesy of Keller Williams Realty Southern Oregon

359 Otis Street, Ashland
$685,000
3 Beds ⋅ 3 Baths ⋅ 220229521 MLS
Enjoy fantastic views of Grizzly Peak & the surrounding hills! Conveniently located close to downtown, this 2021 built home offers 1,624 square feet, 3 bedrooms plus an office and 2.5 baths, with the primary bedroom & main living areas on the main floor. The open floor plan features engineered hardwood floors, a gas fireplace, lots of natural light, and a well designed kitchen with an island, quartz countertops, stainless steel appliances, and custom cabinetry with soft close drawers and cabinet hinges. The primary suite features a walk-in closet, tiled shower, and dual vanity. Also on the main level are the office, laundry room, half bath & garage access. Built by Taylored Elements Construction to Earth Advantage Platinum Standard, the home features ductless heating and cooling, paid off solar panels, and an EV charger in the garage. The front and back yards are fully landscaped with irrigation. A great combination of views, thoughtful design, & comfortable living close to downtown.

359 Otis Street, Ashland

Courtesy of Windermere Van Vleet & Assoc.

210 Alicia Street, Ashland
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 220229442 MLS
Enjoy the relaxed Ashland lifestyle just minutes from downtown, parks, and trails. Tucked into a peaceful setting with lovely East Hills views, this light-filled home is the final new build in a four-lot subdivision. Spacious rooms and an open layout are designed for comfortable living and entertaining. The custom island kitchen features a butler's pantry and flows effortlessly into the dramatic vaulted great room with a striking fireplace. The primary suite offers a spa-like retreat with walk-in shower, dual vanities, and generous walk-in closet. Abundant storage throughout adds everyday convenience. Living spaces extend outdoors to a covered patio, perfect for dining and enjoying the views. Thoughtful finishes, natural light, and a welcoming floor plan make this new Ashland home something special.

210 Alicia Street, Ashland

Courtesy of John L Scott Ashland

1650 Neil Creek Road, Ashland
$1,175,000
5 Beds ⋅ 4 Baths ⋅ 220229364 MLS
OWNER CARRY AVAILABLE! GOURMET KITCHEN. EMIGRANT LAKE VIEWS. 22 ACRES OF PRIVACY. This updated 5-bedroom, 3.5-bath home offers 3,270 sq ft on 22.05 acres. The gourmet kitchen features granite countertops and a stunning oversized island with 360-degree access for cooking and entertaining. Guest quarters and two separate laundry rooms provide flexibility. Updates include all-new doors and windows, a new roof, and new stucco with an imperfect smooth finish and upgraded cloth underneath designed to help reduce temperatures. A large garage with generous shop space accommodates vehicles, tools, and hobbies. The engineered greenhouse includes a concrete perimeter and separate power meter, with potential for shop conversion, subject to buyer due diligence. Level areas offer possibilities for future projects; buyers to verify permitted uses and development options. Enjoy beautiful lake views, exceptional privacy, and versatile spaces--with owner financing available to bring your vision to life!

1650 Neil Creek Road, Ashland

Courtesy of eXp Realty, LLC

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

487 Rock Street, Ashland
$600,000
4 Beds ⋅ 3 Baths ⋅ 220229270 MLS
Beautiful, charming, updated craftsman in the historic Skidmore Academy district with close to proximity to downtown Ashland, Lithia Park, shops, and dining. The peaceful 'Pollinator Garden' has abundant, beautiful perennials, many fruit trees, and a separate octagon shaped office/art/yoga studio. Both front and back yards/gardens have sprinkler systems for low maintenance gardening. High quality finishes such as Douglas fir, bamboo and Marmoleum flooring throughout the home, along bamboo cabinets and exquisite light fixtures. There is also a great cellar for storage or use as a root cellar! This unique property is loaded with historic charm but don't let the year-built fool you, as there are many upgrades and everything is in great working order. Enjoy Ashland living at it's finest.

487 Rock Street, Ashland

Courtesy of Gateway Real Estate

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

164 5th Street, Ashland
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 220229137 MLS
An amazing opportunity in an unbeatable location! Three separate living spaces surround gorgeous lush gardens in the heart of the Railroad District. The main home (164 5th) dates to the late 1800s and offers 3+ bedrooms, 2 baths and approximately 2,071 SF, with many improvements including a new foundation, electrical, plumbing, and HVAC ducting in '94. A detached 1 bed/1 bath apartment above the workshop provides vaulted ceilings, abundant natural light, and a private deck overlooking the gardens, plus bonus space below. A separate cottage-style home (162 5th), circa 1945, offers 2 bedrooms, 1 bath and its own private outdoor space. All three living spaces have separate meters for electric and gas. The main house and cottage also have separate water and sewer. Enjoy a greenhouse and outdoor storage bins for gardening. Lovingly cared for by the same owners for over 45 years, this special property shows true pride of ownership!

164 5th Street, Ashland

Courtesy of Ashland Homes Real Estate Inc.

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.

1068 E Main Street, Ashland
$1,250,000
5 Beds ⋅ 3 Baths ⋅ 220228921 MLS
Own a piece of Ashland's history with this incredible historical home, cherished by the same family for 100 years. Built in 1900, this 3,092 sq.ft. home offers 5 bedrooms and 3 full bathrooms and has been beautifully renovated for modern living while preserving its historic elegance. Original details include beautiful woodwork throughout, formal living and dining rooms, inglenook seating, wood flooring, original entry stairwell, and an original fireplace updated with a gas insert. The updated kitchen features custom cabinetry, granite countertops, a large island, and skylights. Updated bathrooms retain their vintage charm with claw-foot soaking tubs and gorgeous custom shower tile-work. The fully fenced property features gated entry, mature landscaping, and a large 2-car garage. Ideally located in the heart of Ashland, just minutes from downtown shopping, dining, entertainment, and nearby parks, making it easy to enjoy everything Ashland has to offer.

1068 E Main Street, Ashland

Courtesy of RE/MAX Platinum

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