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$375,000
3 Beds ⋅ 3 Baths ⋅ 220223627 MLS
Tucked into the desirable Chautauqua Trace neighborhood in Ashland, this well-maintained home was made for indoor-outdoor living. The real showstopper is the spacious private deck, accessed right off the dining area through a sliding glass door, creating an effortless flow from kitchen to open air. Picture slow morning coffee, summer dinners under the sky, and easy evenings hosting the people you love, all in your own peaceful retreat. Inside, easy-care laminate flooring runs throughout the main level, and the home offers three bedrooms and two and a half bathrooms with tiled baths that add both style and durability. The kitchen keeps everything within reach thanks to a large pantry. Beyond your doorstep, walking paths and open space invite you outside, while shopping and the YMCA sit just minutes away. Come experience it in person and picture yourself settling in.

162 Crocker Street, Ashland

Listing courtesy of John L. Scott Ashland.

$799,000
5 Beds ⋅ 2 Baths ⋅ 220223588 MLS
Offered for the first time in generations, this extraordinary fourth-generation Ashland treasure presents a rare opportunity. Own a piece of local history just steps away from world-renowned Lithia Park. This timeless two-story residence sits on beautifully landscaped .32 acre lot. It offers 5 bedrooms, 2 bathrooms, and a character that cannot be replicated. This home is rich in charm and architectural detail. It showcases the craftsmanship of a bygone era, while providing ample space for modern living. Enjoy peaceful mornings on the porch, stroll through Lithia Park, and easy access to downtown Ashland's theaters, galleries, restaurants, and cultural attractions. Homes of this caliber, location, and historical significance seldom become available. This is a once-in-a-generation opportunity to continue the legacy of one of Ashland's cherished homes.

143 Granite Street, Ashland

Listing courtesy of RE/MAX Platinum.

$385,000
2 Beds ⋅ 1 Baths ⋅ 220223583 MLS
Welcome to one of Ashland's most desirable locations - Phillips Corner, just minutes from downtown Ashland. This beautiful 2 bedroom/1 bathroom townhouse was thoughtfully built by KDA Homes with efficiency and sustainability in mind and meets Earth Advantage certification standards. The home features high-efficiency mini split HVAC systems for year-round comfort & energy savings. The kitchen offers ample countertop space, a pantry, and stainless steel appliances, including a gas range, microwave, dishwasher, and refrigerator. Enjoy elegant living spaces & a private balcony, perfect for relaxing outdoors. HOA dues are very affordable and include beautifully maintained landscaping, garbage service, and access to a community playground. The property also features a spacious 2-car garage. Ideally located in the heart of Ashland, you will be just minutes from downtown shopping, dining, entertainment, SOU, and nearby parks, allowing you to fully enjoy everything Ashland has to offer.

61 S Mountain Avenue, Ashland

Listing courtesy of RE/MAX Platinum.

$225,000
220223514 MLS
Hard to find large buildable lots in Ashland at this price. Flat 1 acre residential lot, offering mountain views and the opportunity to build in one of Rogue Valley's most desirable neighborhoods. Conveniently set on E. Main Street, minutes from Southern Oregon University, the renowned Oregon Shakespeare Festival and the plaza. Potential for home and ADU creates endless possibilities with multi-generational living or rental income. Enjoy a sunny setting with ample space for outdoor living, gardens and animals. Build your custom dream home today. Owner-financing available.

E Main Street, Ashland

Listing courtesy of Millen Property Group.

$200,000
220223513 MLS
You won't find a superior residential lot in Ashland at this price. Conveniently set on E. Main Street, minutes from Southern Oregon University, the renowned Oregon Shakespeare Festival and the plaza, this flat lot features mountain views and the chance to build in one of the most desired neighborhoods in the Rogue Valley. Potential for home and ADU creates endless possibilities with multi-generational living or rental income. Enjoy a sunny setting with ample space for outdoor living, gardens and animals. Build your custom dream home today. Owner-financing available.

E Main Street, Ashland

Listing courtesy of Millen Property Group.

$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

Listing courtesy of Keller Williams Realty GP Branch.

$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

Listing courtesy of eXp Realty, LLC.

$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

Listing courtesy of Gateway Real Estate.

$669,900
220223383 MLS
Super Ashland Investment Opportunity--Three Small Homes on One Big Lot! Located just steps to downtown and the Oregon Shakespeare Festival, this property offers many potential uses--owner occupied, rental investment, or perhaps an upgrade to condos or overnight accommodations (verify uses with Ashland Planning). Each well-maintained unit is two bedrooms, one bath with vaulted living, compact kitchen and dining, newer mini-splits, large front entry decks, nice views and two dedicated off-street parking spaces per unit off the alley access. Separate electric meters, owner pays water/sewer. Large lot, mature landscaping, great long-term tenants. A Truly Unique Offering--Don't Miss It!

207 Gresham Street Units 207, 209, 211 Unit Units 207, 209, 211, Ashland

Listing courtesy of John L Scott Ashland.

$699,000
220223307 MLS
Check out this Chalet-style triplex with R-2 zoning offering both short- and long-term rental possibilities just minutes from downtown Ashland. Units 1 & 3 are one-bedroom, unit 2 is 2 bedroom, all units have tile flooring, a kitchen with granite countertops and breakfast bar, a full bathroom with tile shower, and generous living area. Private decks provide outdoor living space, while the upper unit enjoys spectacular views. The property includes off-street parking, one space per unit, plus basement with shared laundry facilities and additional storage. Two units are currently vacant, creating flexibility for an owner-occupant, investor, or those seeking a combination. Updates completed in 2016 include ductless heating and cooling system, electrical improvements, and interior finishes. The metal roof has been recently painted, decks have been updated and water heaters were new in '23. This is a rare opportunity to own a versatile income-producing property in a desirable location.

326 N Main Street, Ashland

Listing courtesy of Full Circle Real Estate.

$779,000
4 Beds ⋅ 4 Baths ⋅ 220223301 MLS
Custom view home with charming detached guest cottage located just above downtown between Lithia Park and the Ashland Public Library. Main level great room with vaulted double-height ceiling, walls of windows, reclaimed clear-grain fir trim, solid-core doors, refinished oak floors, kitchen with composite dining bar, tile counters and backsplash, cabinets with solid wood interiors and custom pull-outs, dining room with glass door to view deck with gas BBQ hookup, bedroom with closet and full ensuite bath, and pantry with washer and dryer. Upper level primary with skylights, hanging closet, French doors to private balcony, and full ensuite bath with jetted tub. Versatile lower guest suite or family room with French doors to paver patio, full bathroom with oversized shower, storage cellar with stainless utility sink, and one-car garage. Detached cottage with permitted kitchen, living area, full bathroom, loft bedroom, and private gated entrance from Terrace Street. Inquire for details!

307 Hillcrest Street, Ashland

Listing courtesy of John L. Scott Ashland.

$360,000
2 Beds ⋅ 2 Baths ⋅ 220223166 MLS
Light-filled townhome in one of Ashland's most desirable locations. This two-bedroom, two-bath home blends comfort, style, and functionality. Soaring vaulted ceilings and abundant natural light streaming through the striking arched window with stunning views of the hills. Living area with cozy fireplace, perfect for relaxing evenings. Durable vinyl plank flooring flows seamlessly throughout. Practical main level bedroom and full bath, ideal for guests or flexible living. Downstairs, spacious primary suite feels like a private retreat, complete with an en-suite bath, walk-in closet, and French doors that open to a charming courtyard sitting area. Large kitchen provides generous counter space and storage. Enjoy beautifully maintained grounds along with community amenities including a fitness room and pool. Fantastic location with inviting features in desirable Ashland.

360 Glenn Street, Ashland

Listing courtesy of John L. Scott Ashland.

$499,000
3 Beds ⋅ 2 Baths ⋅ 220223157 MLS
Lovely single level home within the Oak Knoll Meadows subdivision, also known as ''Ashland's Hidden Gem'' a wonderful neighborhood at the southeast end of town. Home has three bedrooms, two bathrooms with approx. 1741 SF of living space. Light filled kitchen has lots of cabinetry and surface space with a cozy breakfast nook area and window seat. Kitchen opens to the dining area and great room. There is also versatile separate space off the main living area perfect for a den or media room. Primary bedroom suite with dual vanities and walk-in closet. 2nd bedroom is close to the shared bathroom and bedroom number three is up by the entryway and could make for a nice office depending on one's needs. Great curb appeal, nicely landscaped grounds and the backyard is fenced in. Neighborhood has lots of open space, trails, a pond and streams for all to enjoy!

935 Cypress Point Loop, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

$310,000
2 Beds ⋅ 2 Baths ⋅ 220222924 MLS
Welcome home to this light-filled & beautifully maintained 2-bedroom, 2-bath condo in a desirable Ashland location near the YMCA! Perched on the second floor, this inviting home boasts what may be the best Grizzly Peak views in the entire complex, enjoyed from your private balcony. The open living space features durable Pergo waterproof, scratch-resistant laminate flooring throughout most of the home, while a mini-split system provides efficient heating & cooling. Bedrooms are equipped with their own heat & air conditioning window units for personalized comfort. The kitchen shines with stainless steel appliances & opens to a laundry room with shelving that doubles as valuable pantry storage. A single-car garage plus an additional parking space offer convenience, while the shared courtyard with patio furniture creates a welcoming outdoor gathering space for the adjoining four condos. Move-in ready, thoughtfully updated, & perfectly positioned to enjoy all that Ashland has to offer!

2244 McCall Drive, Ashland

Listing courtesy of Windermere Van Vleet & Associates.

$185,000
220222786 MLS
Homesite approval granted. Buyer to conduct due diligence regarding all conditions and requirements applicable prior to permitting and construction. Beautiful 1.17-acre gently sloping parcel with stunning lake views, just 10 minutes south of Ashland. Features an excellent building site, productive well area, easy access, and approximately 0.9 irrigated acres through the Talent Irrigation District. Partially fenced and ready for your dream home!

Highway 66, Ashland

Listing courtesy of John L. Scott Ashland.

$515,000
220222605 MLS
Position your business for success in this flexible commercial opportunity in the desirable hills of Ashland! Formerly operated as a fitness and wellness space, this unique property features an open gym-style floor plan with multiple private rooms ideal for offices, storage, treatment rooms, massage, counseling, personal training, studio use, or creative workspace. The current business is relocating, opening the door for a new owner or tenant to bring fresh vision and energy to the space. Take all the space as your own or divide the space into 3 units as either commercial or residential for additional income and offset of expenses! There are 3 separate entrances, 3 meters, and 3 bathrooms. Don't wait, this is the only one like this!

905 Skylark Place, Ashland

Listing courtesy of Ford Real Estate.

$399,000
3 Beds ⋅ 3 Baths ⋅ 220222380 MLS
Exceptional end-unit townhome less than 1 mile from Southern Oregon University! Originally built as the developer's personal residence, this thoughtfully designed home offers approximately 30% more living space than other units in the community. Inside, you'll find rich Brazilian cherry hardwood floors, elegant Italian mosaic tile accents, new interior paint, and stainless-steel kitchen appliances. The spacious kitchen features granite countertops, abundant cabinetry, and a walk-in pantry, opening to a comfortable living area with a gas stove. The main level also includes a half bath, laundry area, and access to a private fenced patio with additional storage. Upstairs, the generous primary suite captures beautiful mountain views and offers a spa-inspired bath with dual sinks, soaking tub, walk-in shower, and two closets. A detached garage, deeded parking space, community pool, exterior maintenance, and landscaped common areas complete this outstanding property.

820 Park Street, Ashland

Listing courtesy of Windermere Van Vleet & Assoc..

$335,000
220222249 MLS
Prime Ashland location just off Strawberry Lane in an area of fine homes. Perched above neighboring properties, this exceptional .28-acre parcel captures sweeping valley and mountain views, expansive skies, and abundant natural light. The setting is both inspiring and serene, with mature oaks and conifers creating a beautiful natural backdrop. Thoughtfully positioned to take full advantage of its elevated location, the property enjoys remarkable view protection and a sense of openness that is increasingly difficult to find. With no homes immediately on either side, privacy is enhanced while still being just minutes from Ashland's celebrated Plaza, Lithia Park, and the extensive North Ashland trail system. Whether envisioning a contemporary showpiece or a timeless custom residence, this is a rare opportunity to build in one of Ashland's most sought-after locations and enjoy views that will be treasured for years to come.

163 Hitt Road, Ashland

Listing courtesy of Millen Property Group.

$319,500
2 Beds ⋅ 2 Baths ⋅ 220222004 MLS
Light and bright upstairs condo in the McCall Drive Condominium subdivision. This well-maintained 2-bedroom, 2-bath home offers 1,005 sq ft, a single-car garage below, cherry laminate flooring, and a spacious deck off the living area. Peekaboo views of Grizzly Peak can be enjoyed from the primary suite and front door landing. Both bathrooms include tub/shower combinations, and the home also offers a laundry room, heating and air conditioning in all rooms, and all appliances included in the sale. Convenient Ashland location, moments to the YMCA and close to shopping, bike path, and everyday amenities. Per the seller, the owner is currently first in line with the HOA for rental eligibility, making this a potential opportunity for an owner-occupant or investor.

2214 McCall Drive, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

$475,000
4 Beds ⋅ 3 Baths ⋅ 220221886 MLS
3 bed, 2 bath main home with an attached 1 bed, 1 bath studio featuring a separate entrance! You'll love this wonderful neighborhood just 3 blocks from Helman Elementary School, with easy access to the bike path, tennis courts, playground, dog park, and community gardens -- all just 1 mile from Ashland Plaza. This home sits on nearly a quarter of an acre so lots of space to entertain and garden. Incredible fenced rear yard with expansive lawn areas, apple, plum & apricot trees, raised garden beds & grape arbor, covered patio and views of Mt Ashland. Two car garage creates a large space for a workshop or all your outdoor gear.

374 Cambridge Street, Ashland

Listing courtesy of Beyond Real Estate Brokers.

$525,000
220221566 MLS
Prime Ashland Commercial Property - Now Available! 509 Siskiyou Boulevard offers unmatched visibility and a standout location in the heart of town. Situated just south of the Ashland Fire station, this high-traffic property guarantees incredible exposure to both drivers and pedestrians. Don't miss your chance to secure a vibrant commercial space just steps from downtown!

509 Siskiyou Boulevard, Ashland

Listing courtesy of Windermere Van Vleet & Associates.

$325,000
220221434 MLS
Incredible opportunity to own over an acre inside the city limits of Ashland! Beautiful view lots in a desirable close-in location surrounded by other quality homes. These spacious parcels capture incredible views of the Cascades, Grizzly Peak, and Billings Pond. Close to town, but tucked away at the same time. Plenty of room to create a custom home that takes advantage of the space and scenery. City services are at the street. Two separate tax lots allow for a potential multi family opportunity or just one gorgeous dream home!

Schofield Street, Ashland

Listing courtesy of Full Circle Real Estate.

$175,000
220221397 MLS
Beautiful view lot in a desirable close-in location surrounded by other quality homes. This spacious parcel captures incredible views of the Cascades, Grizzly Peak, and Billings Pond. Close to town, but tucked away at the same time. Plenty of room to create a custom home that takes advantage of the space and scenery. City services are at the street. The adjacent lot (TL 7100) is also available for purchase for those looking for additional flexibility, extra space, or a multi-home opportunity.

Schofield Street, Ashland

Listing courtesy of Full Circle Real Estate.

$175,000
220221398 MLS
Beautiful view lot in a desirable close-in location surrounded by other quality homes. This spacious parcel captures incredible views of the Cascades, Grizzly Peak, and Billings Pond. Close to town, but tucked away at the same time. Plenty of room to create a custom home that takes advantage of the space and scenery. City services are at the street. The adjacent lot (TL 7200) is also available for purchase for those looking for additional flexibility, extra space, or a multi-home opportunity.

Schofield Street, Ashland

Listing courtesy of Full Circle Real Estate.

$759,000
5 Beds ⋅ 6 Baths ⋅ 220221349 MLS
71, 73 and 75 Wimer. Gorgeous updated including plumbing and electric vintage home w/charm remaining a few blocks to downtown Ashland. The main home has 3 bedrooms (2 with ensuite baths) the 3rd bedroom has an ensuite 1/2 bath. Formal living and dining and eat in large kitchen w/breakfast bar & nook. Granite countertops. Wood floors on main level & carpet on stairs & bdrms. The woodwork door trim is beautiful & probably original. Newer deck & A/C unit. Detached building (71 and 73 Wimer) are one level studio units with kitchens & baths. 73 Wimer has private deck. Main house is rented for $2375.00 p/month & tenant pays utilities except water. Studios have been rented for $1250.00 & $1350.00 per month with utilities included & they have a separate shared laundry facility. Unique property for owner occupied or income producing. Circular driveway for main home & 2 parking spaces in front for studios. Has been traveler accomodations in the past. Buyer to do own due diligence on u

75 Wimer Street, Ashland

Listing courtesy of Absolute Realty.

$525,000
4 Beds ⋅ 2 Baths ⋅ 220221283 MLS
Charming historic home with 29+ years of improvements and stewardship. Updated electrical, HVAC, plumbing, sewer line, new roof, solar tubes, skylights, wood-wrapped casement windows, and decks. Wood flooring, vintage fixtures and hardware, period lighting, leaded-glass windows, and picture rail moldings. Spacious open living and dining area with wood stove and door to covered side-porch, kitchen with wood and glass-fronted display cabinets, laundry closet, two bedrooms, and full bathroom. Vaulted upper-level landing, wood-paneled bedroom with panoramic mountain views, full bathroom, and fourth bedroom with closet. Terraced grounds with mature trees, ornamental plantings, paver patio, meandering pathways, sunny fenced gardening areas, rustic garden shed, and renovated detached garage workshop. Property backs to 1.43-acre natural greenspace owned by the City of Ashland near Hald-Straberry Park; conveniently located within a half-mile of downtown. Inquire for details!

71 Scenic Drive, Ashland

Listing courtesy of John L. Scott Ashland.

$449,000
220221201 MLS
Perched in Ashland's sought after Eastfield neighborhood, this ready to build homesite offers a rare opportunity to create your vision in one of the area's most desirable settings. Positioned along quiet Sunnyview Drive, the property enjoys a peaceful residential atmosphere with immediate access to the natural beauty of Ashland's west hills. Just moments away, Hald/Strawberry Park and its network of walking and hiking trails provide a seamless connection between neighborhood living and the outdoors. Eastfield is known for its scenic surroundings, established homes, dead end street, and resident tennis court. This lot has been thoughtfully prepared for construction, with geotechnical work completed and building plans ready, but have not been approved yet. Utilities including water, sewer, and power are available at the street, offering a streamlined path from purchase to building in a location defined by privacy, beauty, and long term appeal.

168 Sunnyview Street, Ashland

Listing courtesy of John L. Scott Medford.

$379,000
2 Beds ⋅ 1 Baths ⋅ 220221178 MLS
Ashland Garden Cottages boast Earth Advantage Platinum Status with Owned Solar Panels. Energy Star appliances, efficient layout of 2 bedrooms, 1 bathroom, stackable washer/dryer, and a living area to include the kitchen, dining area, and living room. Covered front porch, no common walls, quartz countertops, tile shower, and designer lighting. All appliances shown are included in the sale.

162 Mountain View Drive, Ashland

Listing courtesy of Full Circle Real Estate.

$749,000
2 Beds ⋅ 2 Baths ⋅ 220221177 MLS
This sophisticated home combines high-end finishes & top-of-the-line infrastructure w/ stunning sunset views, a strong producing well w/ water rights, & a professional-scale solar array designed for complete self-sufficiency. Enjoy a grand layout featuring vaulted ceilings, wide plank engineered white oak floors, two wood stoves, and Knotty Alder solid core doors. Sliders lead to a brand new two-tiered deck, while the primary offers a free standing tub, marble shower, & a view balcony. This smart home provides seamless control over lighting, media, HVAC, etc via a central wireless hub. The firewise exterior includes a metal roof and fiber cement siding. A 28 solar panel array with 22,000KW storage is backed by two generators integrated for automatic operation. There's a heated barn with drive-through doors, two climate-controlled 40' shipping containers, & a storage shed. Newly completed in 2024 & 15min to town, this property is one of a kind. Inquire for a full features list.

8351 Dead Indian Memorial Road, Ashland

Listing courtesy of Gateway Real Estate.

$150,000
220221155 MLS
Incredible views facing the sunrise, Pilot Rock and Mount Ashland! The non-expiring homesite is approved by Jackson County! Pad for home and the driveway are both in and the acreage gives you plenty of privacy. There are two seasonal creeks running through this property and plenty Ponderosa pines and oak trees are sprinkled on the land. Deer and other wildlife also call this home so you might want to as well! Priced right, hurry! Don't wait on this 20.41 acre piece of beauty!

8074 Highway 66, Ashland

Listing courtesy of Ford Real Estate.

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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: