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$585,000
5 Beds 3 Baths 220219281 MLS 1,973 SqFt. 8,712 Sqft. Lot 0.2 Acres
Located above the Boulevard in one of Ashland's most sought-after neighborhoods, this 5-bedroom, 3-bath home offers the perfect blend of convenience and opportunity. Just minutes from downtown, local shops, restaurants, and hiking trails, the location is hard to beat. Inside, you'll find a functional layout with a cozy fireplace anchoring the main living space as well as original hardwood flooring. Updated solid wood interior doors throughout the home offer a touch of modern sophistication, while multiple sky lights allow for plenty of natural light. Outside, the lot provides plenty of room to garden, or reimagine the space to fit your vision. Whether you're looking for a solid investment property or a place to create your dream home, this one is full of potential.

430 Ashland Street, Ashland

$589,900
3 Beds 2 Baths 220219278 MLS 2,052 SqFt. 6,969 Sqft. Lot 0.16 Acres
Perched above the university in a prime central location, this bright and inviting 3 bedroom 2 bath home offers 2052 sq. ft. of living space. The open concept main level living is filled with natural light and features a spacious layout ideal for everyday living. There is a beautiful river rock fireplace providing a cozy element to the home. Downstairs is a separate living space that provides added versatility perfect for guests to gather or multigenerational living. This lovely home sits on a generous flat lot offering abundant grounds for gardening and outdoor activities. Two spacious decks provide the perfect spot to entertain, relax and take in the beauty this property has to offer. Due to its ideal location and living space, this home has been a great family home and income property for many years.

571 S Mountain Avenue, Ashland

$1,150,000
4 Beds 4 Baths 220219269 MLS 3,132 SqFt. 13,503 Sqft. Lot 0.31 Acres
Exceptional mid-century modern home on an oversized corner lot with sweeping mountain views in a highly sought-after neighborhood. Thoughtfully remodeled, it blends iconic design with modern comfort and seamless indoor/outdoor living. The light-filled living room features vaulted wood ceilings, expansive windows, and a striking stone fireplace. The open kitchen is a chef's dream and built for entertaining, with a 6-burner DCS range, quartz countertops, and a breakfast bar. The Dining area opens onto a wraparound deck and beautifully landscaped yard with Japanese-inspired design--ideal for relaxing or hosting while taking in the views. The main-level primary suite offers a private retreat with office/lounge space and a spa-like ensuite bath with soaking tub and steam shower. Downstairs includes two bedrooms, a full bath, storage, and a large bonus room for guests, media, or a gym. Steps from hiking and biking trails, this is a rare blend of design, location, and lifestyle.

1005 Timberline Terrace, Ashland

$555,000
3 Beds 2 Baths 220219258 MLS 1,778 SqFt. 7,405 Sqft. Lot 0.17 Acres
Versatile living with income potential, conveniently located near town. Extensive updates include new kitchens on each level, energy-efficient windows & hard-surface flooring (2021), & a renovated bathroom (2025). The main level offers 1,100 sq ft with 2 bedrooms, 1 bath, and a blend of 1949 charm and modern updates. Features include spacious living/dining areas, office nook, and a remodeled kitchen (2020) with new cabinets, appliances, and white Macaubas Brazilian stone counters. The lower level is a 678 sq ft ADU w/separate address/utilities, radiant floor heat, updated kitchen (2021), bath, laundry, & private patio. Detached studio (2017) w/ water, power, bath, & automatic garage, ideal for home office or art space. Set on a private, fenced, landscaped 0.17-acre lot w/ deck views.

251 E Hersey Street, Ashland

$695,000
4 Beds 3 Baths 220219192 MLS 2,902 SqFt. 9,147 Sqft. Lot 0.21 Acres
This home checks all the boxes - above boulevard; walking distance to downtown & hiking trails. This remodeled mid-century home has versatility for a multi generational family or an active couple looking for functional & social living spaces. Take in views from the front deck of the Ashland hills, which you'll also enjoy from the living & dining. Enjoy cooking on your induction stove, w/ newer appliances & a gorgeous acacia hardwood island that sits on top an antique asian cabinet. Master en-suite boasts ton of closet space. The 2nd floor w/ its high ceilings & sweet alcoves holds another master suite w/ walk in closet. Other bedrm used as the workout/yoga rm. Incl full bathrm. Basement was refinished w/ stained concrete floors, perfect hanging out in the family rm. Also incl bedrm/office, full bathrm, mud rm, w/ separate entrance, laundry rm, large pantry area & plenty of storage space. Out back, there is a covered eating area w/granite counters. Garage wired for level 2 EV charger.

796 Forest Street, Ashland

$555,000
2 Beds 1 Baths 220219190 MLS 1,239 SqFt. 7,405 Sqft. Lot 0.17 Acres
Prime Ashland location, single level and a detached single car garage wired for EV Charger + a workshop situated on a large corner lot. This 2 bed, 1 bath home offers 1,239 sq ft not including extra space in the basement. You'll fall in love w/ the plaster walls, barrel ceilings, arched doorways, built-ins & a quaint entryway that sets a warm, inviting tone. The spacious, open kitchen includes an island, plenty of counterspace & storage. True picture windows fill the space with natural light plus take in the large fenced backyard and oversized deck. Cozy up by the fireplace in the living room and enjoy the thoughtful craftsmanship throughout. Beautiful mature trees and flowers and plenty of space for gardening, recreation, or extra storage. New roofs on both the home and garage round out this Ashland gem. Located in a sought-after neighborhood close to town and everyday amenities--this is one you won't want to miss!

475 Liberty Street, Ashland

$512,500
3 Beds 2 Baths 220219026 MLS 1,727 SqFt. 8,712 Sqft. Lot 0.2 Acres
Charming Craftsman nestled in one of Ashland's most beloved neighborhoods, just two-level blocks from historic downtown and conveniently close to the Oregon Shakespeare Festival. Built in 1903, this 3-bedroom, 2-bath home carries over a century of character and history and is ready for its next chapter. Original wood floors, wood-framed windows, and classic Craftsman details offer a strong foundation for the buyer with vision and a passion for preservation. Situated on a .20-acre lot zoned R-2 with alley access, the property offers excellent potential for an ADU or additional units (buyer to perform due diligence). Priced to reflect the home's current condition, this is a rare opportunity to own a piece of Ashland history and shape it into something truly special.

590 Allison Street, Ashland

$603,000
4 Beds 3 Baths 220218790 MLS 2,435 SqFt. 12,632 Sqft. Lot 0.29 Acres
Check out this amazing split-level home with stunning views of Grizzly Peak! Nestled on a spacious corner lot in a sought-after neighborhood above Siskiyou boulevard, this four-bedroom gem has plenty to offer. You'll find three full baths, a laundry room, and a large bonus room that opens up to a private patio—perfect for relaxing. Upstairs,the living room features a cozy fireplace, and big windows flood the space with natural light. The bright kitchen has a sliding door that leads to a wraparound Trex deck that's perfect for entertaining or just soaking up the sun. The spacious primary bedroom comes with its own ensuite bath, plus there's another bedroom and full bath on this level. Head downstairs to discover two more bedrooms, a full bath, and a versatile flex space with its own entrance—ideal for guests or a home office. The oversized deck and huge backyard, complete with mature trees and a garden space, make outdoor living a breeze.

1120 Beswick Way, Ashland

$475,000
3 Beds 2 Baths 220218469 MLS 1,791 SqFt. 15,246 Sqft. Lot 0.35000000000000003 Acres
Builder/developer opportunity in one of Ashland's most sought-after neighborhoods. Exceptional redevelopment potential on a .35 acre corner lot just blocks from the Ashland Plaza. Elevated position captures sweeping mountain, city, and territorial views in an area of high-end homes. Existing structure is likely best suited for removal, creating a rare chance to build a stunning custom home on a large in-town lot or explore the potential for a lot split and development of two residences (buyer to complete all due diligence with the City of Ashland). Prime location near Lithia Park, OSF, and downtown amenities. Opportunities like this with size, views, and proximity to town are increasingly rare.

166 Nob Hill Street, Ashland

$547,500
3 Beds 3 Baths 220218409 MLS 1,836 SqFt. 6,534 Sqft. Lot 0.15 Acres
Bright, spacious, & ideally located just minutes from downtown Ashland, shopping, & theater! This 3 bedroom, 2.5 bath home offers 1,836 sq ft of sunny living space with an inviting, open feel. Enjoy brand new carpet in the bedrooms & stylish luxury vinyl plank flooring throughout the rest of the home. Thoughtful updates include new toilets, vanities, light fixtures, recessed lighting, & a ceiling fan. The living area features big picture windows, a cozy fireplace, & sliding doors that open to a welcoming front patio--perfect for enjoying the beautiful cherry blossoms in spring. Downstairs, a versatile family room with its own separate entrance offers great potential for guests, a home office, or multi-generational living. Outside, you'll find a deck & stairs to a fenced backyard, plus RV or boat parking. A double car garage with storage & a workbench adds convenience. Located just three blocks from Siskiyou Blvd, this home blends comfort, updates, & an unbeatable Ashland lifestyle!

390 Morton Street, Ashland

$485,000
3 Beds 2 Baths 220218266 MLS 2,180 SqFt. 6,969 Sqft. Lot 0.16 Acres
Spacious single-level midcentury ranch home with charming eclectic finishes, conveniently located nearby schools, parks, and groceries! Recent upgrades include new roof and skylight, repainted exterior siding and trim, and all new stainless steel kitchen appliances. Abundant natural light and air flow with sliding glass doors throughout home, vaulted primary bedroom with sitting room or office and full ensuite bath, huge media room or potential guest quarters with extensive built-in storage cabinets, kitchen with two pantry storage areas, open dining and living room with large picture window, two guest bedrooms with closets, full guest bathroom with tub shower, and hallway laundry room with washer and dryer. Private fenced front and back yards with mature trees and hedges, expansive concrete patio with hot tub, grass lawns, new garden shed, and extended driveway with ample space for multiple vehicles or RV parking. New gas furnace and central AC system in 2020. Inquire for details!

2999 Diane Street, Ashland

$595,000
2 Beds 2 Baths 220218232 MLS 1,005 SqFt. 3,484 Sqft. Lot 0.08 Acres
This charming bungalow is perfectly situated in the heart of Ashland's desirable Railroad District. The new exterior paint and cozy front porch invites you in with its beautiful craftsman charm. The 2 bed 2 bath 1005 sq. ft. home offers easy one level living that boasts lovely hardwood floors and modern amenities creating a warm and timeless ambiance. The dining room is filled with natural light, with a wall of windows to enjoy the beauty of the fully landscaped and private backyard. There is a picturesque Jack and Jill bathroom featuring a claw foot tub and tile that still represents the era of the home. A small garage is located at the back of the property with alley access and possible ADU potential. This is the perfect place to call home or invest in Ashland's vibrant community, located just up the street from one of Ashland's favorite spots, Noble Coffee.

131 4th Street, Ashland

$735,000
3 Beds 3 Baths 220218220 MLS 2,101 SqFt. 68,389 Sqft. Lot 1.57 Acres
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

$650,000
4 Beds 4 Baths 220218210 MLS 2,130 SqFt. 12,196 Sqft. Lot 0.28 Acres
Charming, updated VIEW home with legal detached ADU! The main home is 1470 SF & was tastefully updated the past 5 years. Wide plank ''Flooret'' LVP flooring throughout, new windows & sliding door, Ductless energy efficient heat/air system, granite counters & vanities, appliances & much more. Versatile floor plan w/ 3BR & 2 full baths allow for a nice separation of spaces & currently used for multi-generational living. Spectacular mountain views from the living space & back deck area to enjoy the changing colors of the seasons. Cozy woodburning FP in the living room. The kitchen has granite counters, pantry and newer appliances. The lower level has an attached 2 car garage, laundry & ½ bath. The detached ADU has its own off St driveway & newer view deck facing the large back yard. Open floor plan, large windows, vaulted ceiling, sleeping loft, kitchen, 3/4 bath & laundry in a total of 660 SF. Mature well-maintained trees grace the .28 AC lot & TID irrigation rights are a gardener's dream.

1159 Park Street, Ashland

$582,000
220217452 MLS 12,196 Sqft. Lot 0.28 Acres
Opportunities like this are rare in Ashland. Tucked into a quiet, established neighborhood, this property offers two homes on one lot. One unit has been thoughtfully remodeled by renowned local architect Milo Shubat, featuring a light-filled, modern interior with vaulted ceilings, skylights, clean finishes, and an open kitchen with custom cabinetry, tile accents, and stainless appliances. The larger home offers a unique coastal contemporary feel, with exposed painted beams, a striking stone hearth, and great natural light throughout. The layout has strong bones and a comfortable flow, with a spacious living area that opens toward the deck and backyard. Both homes feature level, fenced backyards with garden space, and the larger unit includes a generous deck. This is a rare chance to step into a highly sought-after Ashland location with flexibility, character, and room to add value over time. Property has three full bathrooms.

968 Garden Way, Ashland

$535,000
3 Beds 2 Baths 220217271 MLS 1,205 SqFt. 7,405 Sqft. Lot 0.17 Acres
Charming modern home with an open and inviting layout. The kitchen flows seamlessly into the living room, creating a comfortable gathering space centered around a cozy wood burning fireplace. Three bedrooms and one bathroom are located on one side of the home, offering a functional and private layout. The converted garage provides additional living space with a heated office space plus still enough room for plenty of storage. You won't want to miss the second bathroom complete with a newer stunning tiled shower. A wood sliding glass door from the living room provides easy access to the low-maintenance private backyard. The most charming in-ground heated solar pool with gazebo and concrete slab is perfect for relaxing or outdoor gatherings. Conveniently located near downtown Ashland and offering beautiful views of the valley. Situated on a large corner lot. Welcome Home!

325 Taylor Street, Ashland

$2,500,000
220217226 MLS 4,791 Sqft. Lot 0.11 Acres
Located in the vibrant core of Ashland, 145 E Main Street presents a rare opportunity to own a historic, income-producing commercial asset in one of Oregon's most desirable downtown districts. Built in 1905, this classic property blends timeless character with strong investment fundamentals, currently delivering a 6% cap rate. The building offers 3,960 sq ft of commercial/retail space, presently occupied by professional office users and a popular locally owned restaurant that benefits from excellent downtown foot traffic. In addition, the property includes 2,920 sq ft of parking or warehouse storage space, currently leased as income-generating parking spaces--an increasingly valuable amenity in downtown Ashland. Positioned along E. Main St in the heart of the city's dining, shopping, and cultural corridor, this property provides investors with stable tenancy, multiple revenue streams, and long-term upside in a highly sought-after market. And 1 block from the Shakespeare Festival!

145 E Main Street, Ashland

$855,000
220217221 MLS 11,761 Sqft. Lot 0.27 Acres
Prime Investment & Development Opportunity in Ashland. Well-maintained duplex located close to downtown offering immediate cash flow and long-term upside potential. Both units are rented at $1,450 per month ($2,900 total), with tenants paying all utilities, keeping operating expenses low. Property has an excellent rental history and is professionally managed. Capital improvements include newer roof, vinyl windows, stainless appliances, gas log fireplace (rear unit), new water heater and additional updates. Situated on a large approx. 0.27-acre R-3 high-density zoned lot, creating exceptional future redevelopment potential. The City of Ashland Planning Department indicates a 5.4 base density factor with potential for up to 20 units. (buyer due diligence required). For development details contact Aaron Anderson or Nick Schubert at City of Ashland Planning Department.

128 S Mountain Avenue, Ashland

$539,000
4 Beds 3 Baths 220216358 MLS 1,794 SqFt. 7,840 Sqft. Lot 0.18 Acres
Set on a private corner lot above the boulevard, this 4-bedroom, 2.5-bath home offers a versatile layout designed to accommodate a variety of lifestyles. Thoughtful modifications were made to support full-time care, including wheelchair accessibility to the main and lower levels and upgraded electrical features, while still maintaining a warm, inviting feel throughout. The main level includes the galley-style kitchen, living area, half bath, and garage access. A short flight up leads to three bedrooms and an updated bath with jetted tub and added storage. Downstairs, the spacious primary suite features a large accessible custom bath with Corian surround. Whether you're seeking enhanced accessibility, multigenerational living options, or simply a well-maintained, move-in ready home with flexible space, this property offers comfort and adaptability.

1059 Terra Avenue, Ashland

$549,000
3 Beds 2 Baths 220216210 MLS 2,209 SqFt. 18,295 Sqft. Lot 0.42 Acres
First time on the market in 50 years, this is an amazing opportunity to own a home that sits on .42 acres on the flat part of upper Park St. The home has a wonderful in-law, guest or home office set up that has the potential to be converted into an ADU (check with city). The main house is full of light and has a lovely living room with a fireplace that is a great gathering place. The three bedrooms are set away from the living space allowing for privacy. A large sunroom and interior greenhouse open to the level backyard that has mature plantings and plenty of open space, all irrigated with TID water. The guest/office area has it's own bathroom and kitchenette and is connected to the main house with a small breezeway, allowing for a nice separation of space. Sitting close to the shops of south Ashland and just down the street from an amazing trail network, this home is has so much potential to become a showpiece home on a prime lot in a prime location.

965 Park Street, Ashland

$500,000
3 Beds 2 Baths 220216167 MLS 1,270 SqFt. 9,147 Sqft. Lot 0.21 Acres
Enjoy beautiful views from this 3 bedroom, 2 bathroom Ashland home situated on a spacious lot. The full upstairs primary suite offers privacy and comfort, complete with a walk-in closet, private balcony, and dedicated heating and air unit. The large lot has room to expand, garden, or further develop, with ADU potential per the City of Ashland. Electric and water have already been run to the back of the lot, creating flexibility for future possibilities. Inside, you'll find numerous thoughtful upgrades including a fully remodeled downstairs bathroom, new roof, updated lighting, new appliances, a smart thermostat, sewer line replacement, and more. Located near Southern Oregon University and Ashland High School, this home offers easy access to schools, parks, and Ashland's vibrant downtown.

605 Elkader Street, Ashland

$675,000
4 Beds 3 Baths 220216097 MLS 2,094 SqFt. 6,534 Sqft. Lot 0.15 Acres
Charming vintage home and detached cottage with private gardens, paver patios, and mature ornamental trees located in the desirable Skidmore Academy Historic District directly across from Briscoe Park, within an eight-minute walk to Ashland's downtown plaza! Main home features fir floors, high ceilings, updated lighting, formal dining with glass door to fenced backyard, kitchen with refurbished cabinets, granite counters, tiled backsplash, double sink overlooking garden, stainless appliances, pantry with washer dryer, front bedroom with closet, full bath with penny round vinyl floor and tub shower with tile surround, second main-level bedroom or office with closet, upper-level primary suite and full ensuite bathroom with shower, plus a basement cellar. Detached cottage with pecan wood floor, kitchen area, laundry alcove with washer dryer, sliding glass door to private deck and paver patio, full bathroom with shower, and spiral stairs to vaulted bedroom. Inquire for details!

216 Central Avenue, Ashland

$437,000
3 Beds 2 Baths 220216075 MLS 1,152 SqFt. 9,583 Sqft. Lot 0.22 Acres
Sweet single-level living in the sought-after Quiet Village neighborhood. Located near Helman Elementary School, the dog park, Bear Creek Greenway, trails, and just minutes from downtown Ashland, this 3-bedroom, 2-bath home offers comfort and convenience. The spacious primary suite includes an ensuite 3/4 bathroom with tiled shower, while two additional bedrooms have backyard views. The kitchen features a gas range and sunny dining nook overlooking the covered side patio with outdoor fireplace area and space for a hot tub. Inviting living room with wood-burning fireplace opens to a rear deck and spacious, private, fully-fenced backyard. Set on a level .22-acre lot with mature landscaping, garden beds, fruit trees. Brand new roof (Jan 2024)!

349 Tudor Street, Ashland

$709,000
3 Beds 2 Baths 220215618 MLS 1,634 SqFt. 7,840 Sqft. Lot 0.18 Acres
Owning this Victorian home built in 1900 has been one of the great joys of my life. From the moment I stepped inside, I felt its timeless character in the tall ceilings, classic architectural details, and warm natural light throughout. The home has been lovingly maintained to honor its history while remaining comfortable and inviting. The mature landscaped yard is a sanctuary I treasure, offering beauty, shade, and peaceful moments through every season. Living in Ashland's cherished Railroad District has been a gift, placing downtown dining, theaters, parks, and everyday adventure nearby while still enjoying a quiet, established neighborhood. 156 8th Street has been more than a residence; it has been a place of pride, comfort, gathering, and meaningful memories. I hope its next steward feels inspired by its character, history, and the special lifestyle this remarkable home provides each day. It truly reflects Ashland charm and enduring craftsmanship for generations to admire and enjoy.

156 8th Street, Ashland

$600,000
3 Beds 3 Baths 220215540 MLS 2,290 SqFt. 32,670 Sqft. Lot 0.75 Acres
Close proximity to Mt. Ashland, Emigrant Lake, & numerous outdoor adventures, yet not far to Ashland's vibrant downtown. This beautifully updated home situated on a .75 acre lot seamlessly combines modern updates with timeless character. Original details such as stunning tongue-and-groove ceilings & restored hardwood floors preserve the home's original charm. The fully renovated & expansive primary suite is a true retreat, featuring warm pine floors, a cozy wood stove, generous closet space, & a spa-inspired en-suite bath . The light-filled main level living area is framed by abundant windows that invite the outdoors in. Step outside to the new wraparound deck & soak in the serene surroundings & views. The lower level provides an additional bedroom/living area & full bathroom that can serve a variety of uses, including multi-generational living space. Recent significant improvements include a new roof, HVAC, wraparound deck, interior & exterior paint, water treatment system.

200 Timberlake Drive, Ashland

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: