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$765,000
3 Beds 2 Baths 220225306 MLS
Rolling pastures, gentle hills & gorgeous Mt. Ashland views create an exceptional setting for this beautifully updated single-level home on 6.85 acres. Rebuilt from the studs in 2004, it blends timeless craftsmanship with a light-filled, open design where every room connects to the surrounding landscape. Vaulted ceilings, expansive view windows, maple hardwood floors, custom Shaker-style woodwork, fir doors, built-ins & two fireplaces add warmth and character. The spacious kitchen with sunny breakfast nook opens to wraparound decking & gardens, inviting outdoor living amid sweeping views, colorful seasonal blooms, spectacular sunsets & brilliant star-filled skies. The rebuild included updated plumbing, electrical, Milgard windows, raised ceilings, remodeled kitchen & baths, added living space, on-demand hot water & underground utilities. Outbuildings with animal shed & approx. 850-sf shop complete this peaceful, private retreat, above the fog, below the snow & just 10 minutes to town

2815 Dead Indian Memorial Road, Ashland

$996,000
5 Beds 3 Baths 220225227 MLS
Beautifully restored 1908 classic home located on a rare R2 zoned double lot just blocks from downtown Ashland's theatres, restaurants, galleries, and parks. MAIN RESIDENCE Featuring 3 bedrooms and 2 full baths, interior highlights include original fir floors, high ceilings, designer lighting, updated kitchen, pantry and abundant natural light throughout. Flexible layout supports guest space, office, or extended living arrangements. LOWER LEVEL Remodeled with separate entrance, kitchen, bedroom and full bathroom offering independent living space. Foundation of main home was updated in 1997 with central heat, air, electrical and plumbing systems. DETACHED COTTAGE Separate remodeled cottage with bedroom and bath ideal for additional flexible living needs, guest suite, or office. OUTDOOR FEATURES Mature landscaping with fenced yard, irrigation, water feature, dry sauna, spa, storage shed, and ample off street parking. ADDITIONAL HIGHLIGHTS R2 zoning ideal for income producing living.

541 Fairview Street, Ashland

$420,000
4 Beds 2 Baths 220225100 MLS
This 4-bedroom, 2 bathroom home was built in 1997, and is tucked back off Bellview Ave in a charming, well-located community and has No HOA and new HVAC in 2026! Bright open kitchen with pantry, new 2025 refrigerator & dishwasher, and easy access to a private back Trex deck, --perfect for morning coffee or evening grilling, with front and back timed sprinkler system. Main level living includes a bedroom with full bath, quartz countertops and tile flooring. Simulated wood floors throughout and fresh interior paint. Upstairs features flexible living: the primary is light and bright, second bedroom has two conjoined rooms ideal for a sitting area, dressing room or home office. Upstairs also features a third bedroom and a full bathroom with beautiful dual vanity. It also has a Single-car garage. Close to Bellview Elementary, grocery stores, public transit, restaurants and more.

923 Bellview Avenue 2 Unit 2, Ashland

$799,000
1 Beds 2 Baths 220224982 MLS
It's all about the beautiful 13.39 contiguous acres with 12.6 acres of TID irrigation, panoramic views and just minutes to downtown Ashland. Family owned since 1964, the original home was built in 1915. There are 3 separate tax lots, one with the original home,8-stall horse barn and workshop (5.81 acres), one that has a non-expiring homesite (confirm with county) with fantastic panoramic views (4.53 acres) and the third with a large barn (3.05 acres) and separate access. All 3 may be sold separately (check with Jackson County Planning). Tax lot #700 has a small home, large shop, a 8-stall barn, tack room and small living quarters in the back. There is a 2-story barn on tax lot #300. The portion of the property growing grass and clover for hay produces approximately 400-600 bales and has wheel line irrigation. There are many other potentials for this EFU property.

1249 N Valley View Road, Ashland

$279,000
2 Beds 1 Baths 220224865 MLS
This Beautiful, turn key ready 2-bed / 1 bath condo, within a short walk to downtown Ashland, coffee shops , restaurants , shopping, & Southern Oregon University . Nice and bright natural light throughout with skylights in the living area. The kitchen has granite counters with stainless-steel appliances. Open floor plan flows into a spacious great room with 9ft ceilings and plenty of windows to take in the surrounding mountain views including Grizzly peak. Natural Fir doors and trim throughout. Ductless heating and air. Don't be fooled by the sq ft, this condo has a feel that it is much bigger. A modern and aesthetically pleasing living space in a small association. The furniture is included in the sale. Don't miss out on this rare opportunity to own a low maintenance home in Ashland. The unit is upstairs. Sellers are open to offers.

1249 Iowa, Ashland

$650,000
4 Beds 3 Baths 220223920 MLS
Welcome to desirable Clay Creek Gardens, where comfort & convenience meet in a peaceful, tree-lined neighborhood. This spacious, truly move in ready home, features quality finishes, abundant natural light, & generous living areas. Hardwood flooring highlights the main living spaces, while large rooms offer flexibility for entertaining, working from home, or everyday living. The well-designed floor plan provides ample storage & a warm, inviting feel throughout. The kitchen is heart of the home w/ granite counters, plenty of storage & is open to the dining/living areas. Main level primary suite w/ dual sinks, walk-in closet + a spacious shower. Outside, enjoy a low-maintenance lot & a private courtyard-style backyard w/ a patio. Residents benefit from low HOA fees and access to a neighborhood park with a gazebo + community gardens. Conveniently located near all Ashland has to offer. Don't miss the opportunity to enjoy spacious living in one of the area's most sought-after communities.

2685 Clay Creek Way, Ashland

$690,000
2 Beds 2 Baths 220224672 MLS
Amazing opportunity with 5 legal lots per City of Ashland and phenomenal views. Amy Gunter of Rogue Planning & Development Services has extensively researched and received letter from City of Ashland Legal Lot Determination stating 5 lots. TID water rights. In addition there is a cute, sweet 2 bedroom, 2 bath home with detached garage. Orignal wood floors in bedroom and livingroom and maybe under the carpet in the hall. Living room has fireplace with built in bookcases on either side and you will love the unbelievable mountain views through the picture window. Home has been rented for many years and sits ''as is''. Cute unique kitchen with dining nook. Call listing agent for details and property package. Buyer to do their own due diligence for their own plans for the property.

595 Monroe Street, Ashland

$1,150,000
220224634 MLS
Rare Ashland investment opportunity, three modern townhomes built in 2016, each on its own separate tax lot, offered together as a package. Every unit is a spacious 3-bedroom, 2-full-bath, a hard-to-find configuration in the local rental market. Unit 1173 offers 1,280 sf and a two-car garage, while 1169 and 1171 each offer 1,188 sf and a one-car garage. Turnkey interiors feature stainless steel appliances, warm shaker cabinetry, and 100% solid surface flooring, no carpet anywhere. Current rents total $6,605/month with near-zero vacancy since construction, a track record of dependable income that speaks for itself. Individual tax lots offer long-term flexibility that is rarely found in multi-unit properties. Ideal for the investor seeking newer, low-maintenance construction, or an owner-occupant living in one unit while the other two help pay the mortgage. Close to SOU, downtown, and everyday amenities. Not to be sold separately.

1169 Iowa Street, Ashland

$595,000
3 Beds 3 Baths 220224168 MLS
Welcome to this stunning 1993-built home on a private .29-acre lot. Dramatic floor-to-ceiling windows flood the front rooms with natural light and frame the gorgeous scenery. The main floor features 2 bedrooms, including a large primary suite and walk-in closet, a main-level office/3rd bedroom with built in Murphy bed, 2 full baths, a cozy den, a sunroom, a huge front living room with vaulted ceilings and separate dining space. The eat-in kitchen offers plentiful storage in a serene setting overlooking the hills. The basement has an additional room with a craft room already set up to be a photographer's dark room with ventilation, a sink, and a half bath. Outside is a terraced backyard with gazebo and a huge half wrap around deck all providing spectacular views. Complete with an attached 2-car garage. A Newer roof, washer, dryer, dishwasher, and Air conditioning unit all installed/replaces in 2023 and 2024. Minutes from hiking trails, parks, schools, and shopping! Move in ready.

1536 Pinecrest Terrace, Ashland

$1,200,000
5 Beds 3 Baths 220224554 MLS
One-of-a-kind Southern Oregon retreat just minutes from Ashland! A remarkable property offering a rare blend of privacy, craftsmanship and income potential in a private park-like setting with mature trees. This custom-built 5 bedroom home showcases soaring ceilings, walls of windows with views of Emigrant Lake/Grizzly Peak, large breakfast nook, custom pine log features/dramatic curved staircase, hardwood floors, granite/travertine countertops, floor-to-ceiling fireplace, large 3rd floor bonus wing, 1900+ sq. ft. wraparound cedar deck, workshop, charming playhouse and covered carport. The 1st floor ADU currently operates as a successful AirBNB with 2 bedrooms, beautiful kitchenette, granite countertops, stunning tile bathroom, ADA access, private driveway and entrance, for use as continued rental income or separate multigenerational family living. A former homesite offers additional potential. Rarely does a property combine this level of quiet privacy, quality and versatility.

4567 Old Highway 99 S, Ashland

$735,000
220224513 MLS
Fully renovated home by Coleman Creek Construction with detached studio and garage on rare E-1 zoned acreage with development potential in city limits! Charming front porch and covered wrap-around patio, open-concept living area with double-height vaulted ceiling, kitchen with quartz dining counter, designer lighting, and stainless appliances including gas range oven. Main-level primary suite with skylights, glass door to back patio with retractable awning, and full ensuite bathroom with quartz vanity, deep soaking tub, and oversized shower with seamless glass and tile surround. Additional main-level bedroom and full guest bathroom with quartz vanity, stacked washer dryer, and tiled shower. Vaulted upper-level media room, office, or third bedroom. Detached studio with quartz dining counter, stainless appliances including electric range oven, full bathroom with quartz vanity, tub shower, washer dryer, plus two-car garage. Ample off-street boat or RV parking. Inquire for details!

593 Crowson Road, Ashland

$390,000
2 Beds 1 Baths 220224333 MLS
Move-in ready and professionally cleaned, this charming cottage features central heating and air conditioning, along with numerous updates throughout. Situated on a spacious 0.17-acre lot, the property offers a fully fenced backyard, automatic sprinklers, off-street parking, a garden shed, and a deer-protected garden enclosure--ready for someone to make it shine again. Recent improvements include exterior paint, siding repairs, rebuilt exterior stairs, new luxury vinal plank flooring in the main living area, new tankless water heater, new refrigerator and electric range. The detached bonus room with an efficient wall heat and air AC unit, and abundant light offers endless possibilities as a home office, guest retreat, or hobby room. Conveniently located near downtown Ashland, schools, Grange Co-op, and Ace Hardware.

363 E Hersey Street, Ashland

$299,000
220224404 MLS
Your future homestead, farm, and launch pad for outdoor recreation! A well-maintained road leads to 18.8 usable acres w/panoramic backdrops. Forest & lovely pastures w/mountain views. Approved homesite in your choice of two locations. Septic system installed. 12gpm well drilled in 2013. The charming log-frame barn and paddocks are in full swing and ready for your animals! Property is partially fenced and fully surveyed, with all corners marked. Bring your plans and your joy to the getaway setting you've always wanted. Next door to adventure territory for hiking, biking, paddle-boarding and more! Near extensive BLM & just 15-20 minutes to Howard Prairie & Hyatt Lakes! Buyer to perform due diligence on all aspects of the property, its uses and development potential. One seller is a licensed Broker in the state of Oregon. Shown by appointment only--Buyer's agent must accompany.

15861 Highway 66, Ashland

$630,000
3 Beds 3 Baths 220224225 MLS
Charming custom home with panoramic mountain views on a spacious and private 0.29-acre flag lot located above the boulevard within six minutes of Ashland's downtown plaza. All new low-pile berber wool carpets and fresh interior paint in 2026, new central AC system in 2019, and new roof c. 2016. Main level with solid oak hardwood floors, living room with bay window and gas fireplace, formal dining with French door to concrete paver patio with fire pit, kitchen with tiled counters and backsplash, powder room, laundry closet, and two-car garage with extensive built-in storage cabinets. Versatile upper level with two guest bedrooms, a very spacious primary suite with private office or nursery, two full ensuite bathrooms, and three sets of French doors to the backyard. Abundant natural light with Eastern exposure - dormer windows throughout. Established trees and hedges, mature plantings, and grass lawns with automated drip and sprinkler irrigation. Inquire for details!

430 Wiley Street, Ashland

$699,000
3 Beds 3 Baths 785094435 MLS
This gorgeous home is priced to sell! Perched above the boulevard in an upscale neighborhood of high-end homes, this picturesque property offers the perfect blend of luxury and nature. Located just steps from the scenic hiking trails of Hald-Strawberry Park, less than 1 mile from Lithia Park, OSF, and the best restaurants and shops in Ashland. The main level welcomes you with beautiful views out of every window, solid oak hardwood floors, and a living room with a classic brick fireplace and French doors leading to a lovely deck. The fully renovated kitchen stuns with premium travertine tile flooring, stunning Brazilian quartzite counters, and stainless steel appliances. There's more to love upstairs- gorgeous views, a spacious primary suite, a light and bright guestroom, and a flexible 3rd bedroom that easily doubles as a home office, featuring built-in shelving and a charming window seat. This is a must see that truly feels like home. Solar. EV charging. Please refer to the attached document for a full list of features. Home appraised at 815k. Instant equity.

215 PIEDMONT DR, Ashland

$309,000
3 Beds 2 Baths 220223687 MLS
*Seller Motivated - will entertain all reasonable offers!* Affordable Ashland living in desirable Tudor Heights! This spacious 3-bedroom, 1.5-bath condo offers 1,392 sqaure feet of comfortable living space with mountain and territorial views from a private upper-corner location. The main level features a bright living room with a 60s style fireplace, kitchen, half bath, and flexible den perfect for a home office, guest space, or potential 4th bedroom! Upstairs you'll find three bedrooms, a full bath, and laundry area. Recent improvements include new carpet and a new water heater. Enjoy a private patio, detached carport, and additional storage. Conveniently located near downtown Ashland, Lithia Park, restaurants, shopping, and the hospital. HOA covers water, sewer, trash, landscaping, exterior maintenance, and exterior insurance for easy, low-maintenance living! Ownership occupancy only - no rental opportunities available at this time.

495 Chestnut Street 24 Unit 24, Ashland

$695,000
2 Beds 3 Baths 220223937 MLS
Beautifully Maintained Custom Ashland View Home! This property offers a blend of distinctive architecture and serene privacy with custom windows and natural beauty throughout. Step-down living room with gas fireplace, dining room has built-in shelving; house has engineered hardwood flooring and carpeted bedrooms; kitchen has newer 36'' gas range and built-in desk. Spacious ground-floor master bedroom, second upstairs bedroom, separate office that could be used as a guest bedroom, plus upstairs laundry room. View decks for indoor-outdoor living, mature landscaping and peaceful setting that includes patio, firepit, walking paths and fully fenced backyard. Quality upgrades include Karastan wool carpeting, newer roof, high-efficiency 2-stage HVAC, fresh interior paint, oversized garage with workshop/bonus area, central vac, 220v for EV charging and great storage throughout. Lovely hillside home on a quiet cul-de-sac just minutes from downtown with EZ access to Ashland's trail system.

590 Taylor Street, Ashland

$699,000
3 Beds 3 Baths 220223512 MLS
Gorgeous home, priced to sell!!! Perched above the boulevard in an upscale neighborhood of high-end homes, this picturesque property offers the perfect blend of luxury and nature. Located just steps from the scenic hiking trails of Hald-Strawberry Park, less than 1 mile from Lithia Park, OSF, and the best restaurants and shops in Ashland. The main level welcomes you with beautiful views out of every window, solid oak hardwood floors, and a living room with a classic brick fireplace and French doors leading to a lovely deck. The fully renovated kitchen stuns with premium travertine tile flooring, stunning Brazilian quartzite counters, and stainless steel appliances. There's more to love upstairs- gorgeous views, a spacious primary suite, a light and bright guest room, and a flexible 3rd bedroom that easily doubles as a home office, featuring built-in shelving and a charming window seat. Solar. EV charging. Garage workshop space and so much more! Home appraised at 815k. Instant equity!

215 Piedmont Drive, Ashland

$235,000
2 Beds 1 Baths 220223508 MLS
The cabin of your dreams is waiting for you just 35 minutes from downtown Ashland at The Cabins at Hyatt Lake. Tucked into the trees near the shores of the Lake, this peaceful mountain getaway offers the kind of escape people search for and rarely find. With one of the larger and more desirable layouts, the added bump-out creates extra room to relax, gather, and enjoy every season. Vaulted wood ceilings, warm natural light, and a spacious open living area create an inviting place to unwind after a day on the lake, hiking nearby trails, or winter adventures in the snow. Step outside to the wraparound deck, enjoy coffee in the crisp mountain air, soak in the hot tub, and take in the quiet forest setting. Never used as a rental, this fully furnished retreat is truly turnkey. Main-level bedroom and bath, loft sleeping space above, and an oversized shared 2-car garage for boats, gear, and toys complete the package. Just a short walk to the lake and endless outdoor recreation year-round.

7979 Hyatt Prairie Road 42 Unit 42, Ashland

$850,000
3 Beds 2 Baths 220223497 MLS
Tucked in the hills of Ashland, this exquisite light filled brick home offers a rare blend of elegance, privacy, views and natural beauty. This 3 bedroom, 2 bath house features a large open floorplan, skylights, chef's kitchen with 6 burner gas range and island, expansive great room, double paned windows, dining room, primary suite with walk in closet and so much more. This thoughtfully designed home showcases quality craftsmanship, refined finishes and allows for seamless indoor-outdoor living. The yard features fire safe landscaping, custom organic gardens, dozens of varieties of flowers and trees, Japanese maples, dogwoods, abundant wildlife and a koi pond with waterfall. Enjoy the large multiple car garage and workshop, along with an additional downstairs bonus room with multigenerational living potential. Total square footage including the garage/workshop and finished bonus room is 3436! The home has been very well maintained, with both a newer roof and brand new HVAC system

1365 Ponderosa Drive, Ashland

$14,000,000
220223436 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. The estate encompasses more than 27,000 sqft and features multiple tasting rooms, a ceremonial barrel room, elegant ballroom, full-service 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, corporate retreats, and private events. This combined with significant growth potential make this a rare opportunity to own a premier winery. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

100 Belle Fiore Lane, Ashland

$12,000,000
7 Beds 19 Baths 220223437 MLS
Chateau at Belle Fiore is one of Oregon's most extraordinary estates. Spanning over 17,400 sqft across 4 levels, this French-inspired masterpiece offers 7 bedrooms, 19 bathrooms, and exceptional craftsmanship throughout. An elevator services all floors, including an 8,000 sqft lower level with a wine room, game room, gentleman's lounge, multiple wine bars, and expansive entertaining spaces. Premium finishes include custom cumaru flooring, granite surfaces, and intricate architectural detailing. Set on 17+ acres, including 12+ irrigated acres and a producing vineyard, the estate is ideal for private enjoyment, weddings, retreats, and special events. Exterior features include hand-chiseled golden granite, a hand-cut slate roof, custom copper gutters, dormers, and downspouts. A 2,500+ sqft carriage house, 4-car garage, prep kitchen, and grand gathering spaces complete this iconic estate. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

200 Belle Fiore Lane, Ashland

$26,000,000
220223435 MLS
Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is for sale for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,400+ sqft; it has four levels, 5 bedrooms, 19 bathrooms, a 4-stop elevator, vineyard, 2 bedroom 2500+ sqft carriage house, 4-car garage, resort style pool, hand-cut slate roof, custom copper detailing, and one of a kind craftsmanship throughout. ~ Separately, the Winery features a 32-acre vineyard with 14 distinguished grape varietals. The 27,000+ sqft Italian basilica-inspired facility includes tasting rooms, a ceremonial barrel room, ballroom, restaurant, outdoor dining areas, panoramic views of the Rogue Valley, and a commercial production facility with extensive refrigerated wine storage. Set on nearly 70 acres, this offering includes 49+ acres of water rights. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

100 Belle Fiore Lane, Ashland

$26,000,000
7 Beds 19 Baths 220223434 MLS
Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is for sale for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,400+ sqft; it has four levels, 5 bedrooms, 19 bathrooms, a 4-stop elevator, vineyard, 2 bedroom 2500+ sqft carriage house, 4-car garage, resort style pool, hand-cut slate roof, custom copper detailing, and one of a kind craftsmanship throughout. ~ Separately, the Winery features a 32-acre vineyard with 14 distinguished grape varietals. The 27,000+ sqft Italian basilica-inspired facility includes tasting rooms, a ceremonial barrel room, ballroom, restaurant, outdoor dining areas, panoramic views of the Rogue Valley, and a commercial production facility with extensive refrigerated wine storage. Set on nearly 70 acres, this offering includes 49+ acres of water rights. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

200 Belle Fiore Lane, Ashland

$2,140,000
5 Beds 5 Baths 220223401 MLS
Rare 203-acre Ashland estate with sweeping south-facing views offers a resort setting tucked away at the end of a mountain road. Completed in 2015, the 7,468 sq ft Craftsman residence was designed for beauty and function. The main level showcases two primary suites, two additional oversized bedrooms, expansive living and family rooms, and a gourmet kitchen. One walnut staircase leads to a private loft while a second stairway leads to a spacious upper level bonus room. The partially finished daylight basement has exterior and patio access. The original 1,812 sq ft home is now an amazing fully finished flex space, ideal for guests, office, studio, or recreation. Surrounded on three sides by the Siskiyou Cascade National Monument for vast recreational opportunities. The property offers pasture, wooded terrain, and creek frontage. This rare legacy estate delivers self sufficiency, seclusion, and unparalleled outdoor access while remaining within reach of Ashland's renowned amenities.

22494 Jefferson Road, Ashland

$680,000
3 Beds 4 Baths 220223382 MLS
Enjoy exceptional privacy and beautiful views in this single-family retreat, nestled on a tree-lined 0.33-acre lot in one of Ashland's most desirable neighborhoods. A welcoming front deck leads to the 2,270 sq ft home featuring 3 bedrooms and 3 full bathrooms. The grand living room showcases expansive windows framing stunning trees, the valley and mountain views. The rear deck overlooks a professionally designed/built backyard with a charming gazebo. A versatile 336 sq ft house addition featuring a private half bath and a valley-view picture window is ideal for guests, a home office, or multi-generational living. The oversized 2-car garage provides ample storage and workspace. The garage backdoor leads to a custom Catio porch... Despite its peaceful and secluded setting, this home is conveniently located just minutes from downtown, the hospital, and Lithia Park, offering the perfect combination of tranquility and accessibility.

457 Walnut Street, Ashland

The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

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. Listing content is copyright © 2018 SOMLS, Medford, Oregon. Last updated: