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$1,200,000
220224634 MLS ⋅ 5,662 Sqft. Lot ⋅ 0.13 Acres
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
$669,900
220223383 MLS ⋅ 8,712 Sqft. Lot ⋅ 0.2 Acres
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
$699,000
220223307 MLS ⋅ 6,534 Sqft. Lot ⋅ 0.15 Acres
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
$714,900
220222841 MLS ⋅ 9,583 Sqft. Lot ⋅ 0.22 Acres
Exceptional investment opportunity in the heart of Ashland, being sold ''As-Is''. Long-term pride of ownership shines throughout this well-maintained, fully occupied triplex offering immediate income potential and a strong rental history. The property features three legal and compliant units, each with two bedrooms and two baths, complemented by vaulted ceilings and skylights that create bright, open living spaces. With attractive curb appeal and a desirable location close to downtown Ashland, shopping, dining, parks, and SOU, this is a rare chance to own a stabilized multi-family asset in one of Southern Oregon's most sought-after markets. Properties like this do not come available often and are expected to move quickly. Please do not disturb occupants. Shown by appointment only.

473 Scenic Drive, Ashland
$1,250,000
220222311 MLS ⋅ 5,662 Sqft. Lot ⋅ 0.13 Acres
Versatile mixed-use commercial and residential building with strong rental history in Ashland's historic Railroad District - near parks, shopping, restaurants, and downtown. Full due diligence package available - including updated investment analysis, pro forma, improvements, maintenance records, and floor plans. Main level with two long-standing commercial tenants occupying three units, multiple entrances from A Street, alley access to central bike path, five private parking spaces, and one shared ADA space. Two upper-level residential units - each with spacious living room, kitchen with dining counter and gas range oven, one to two bedrooms, full bathrooms, abundant natural light, and mountain views. Well-maintained property with low-e windows, recent exterior paint, new furnaces and AC units, and a new roof in 2015. Common area courtyard with ornamental trees and plantings. Inquire for details!

545 A Street, Ashland
$450,000
220221378 MLS ⋅ 3,484 Sqft. Lot ⋅ 0.08 Acres
Opportunity is knocking. This charming duplex in Ashland's beloved Railroad District has had extensive updating throughout. Both units offer 1 bed/1 bath layouts with a new foundation, plumbing, and electrical, plus fresh interior and exterior paint, new carpet, and laminate flooring. Currently tenant-occupied on both sides, this is a true turn-key addition to any investment portfolio. Walk to shops, restaurants, and the heart of Ashland from one of the most sought-after neighborhoods in town. Investors, this one's for you. Please do not disturb tenants. Showings are by appointment only.

457 C Street, Ashland
$950,000
220220698 MLS ⋅ 6,534 Sqft. Lot ⋅ 0.15 Acres
Historic 'Alice Foster House' with fully renovated detached ARU permitted for Traveler's Accommodations located on a corner lot in downtown Ashland, directly across from the public library. Seller-carried financing available at 5% interest rate. Main residence with charming wrap-around covered porch, original solid fir floors, built-ins with leaded glass display cabinets, wood-wrapped windows, spacious living room, formal and informal dining areas, kitchen with butcher block island, walk-in pantry, half-bath, three main-level bedrooms with full bath, and a wide stairwell to two upper-level bedrooms with additional full bath. Detached ARU rebuilt in 2014 with a complete kitchen, alder cabinetry with glass displays, solid oak flooring, skylight, full bath, French doors to private covered view balcony, plus a tiled main-level studio or bedroom and additional full bath and laundry room. Fully fenced private brick courtyard and three off-street parking spaces. Inquire for details!

19 Gresham Street, Ashland
$1,195,000
220220575 MLS ⋅ 17,859 Sqft. Lot ⋅ 0.41000000000000003 Acres
Hard to find 4 plex plus separate home on large R-2 lot. Walking distance to downtown. The units have been updated and are well maintained. Fully rented. One unit is rented fully furnished . The main home was remodeled 4 years ago. All units have private rear yards that are newly fenced. One of the apartments is complimented with a tile shower plus separate bathtub. Washers and dryers included in all units. Ample parking for tenants.

67 Woolen Way, Ashland
$2,250,000
220220428 MLS
Rare 10-unit investment opportunity in Ashland's Hillview Condominiums -- close to Scenic Park, Asante Ashland Community Hospital, downtown dining and entertainment. Three-year seller-carried financing available at 3.75% rate with interest-only payments and balloon at maturity. Each unit ranges from 1,034 to 1,174 SqFt with two bedrooms, one full bath, open living and dining space, high ceilings, in-unit laundry, kitchen with granite counters and all appliances included, dedicated parking, storage, and access to landscaped common areas. Ground-level units with fully fenced private backyards and poured concrete patios. Portfolio includes stable tenancy, average occupancy of 4.2 years, room for rent growth, and association-maintained exterior building components including roofs, siding, paint, and landscaping. Complete investment analysis and user guide, rent roll, association documents, title information, and additional due diligence materials available upon request.

230 Grant 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
$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
$557,000
220215494 MLS ⋅ 12,632 Sqft. Lot ⋅ 0.29 Acres
Lovingly maintained duplex with beautiful mountain views. The upstairs unit, 1870, offers 3 bedrooms and 1.5 baths, with abundant natural light filling the living room, highlighted by a wood-burning brick fireplace. The kitchen features generous tile counter space and ample storage. The primary bedroom includes a private half bath, while one of the two additional bedrooms provides direct access to the deck overlooking the peaceful backyard. The downstairs studio, 1872, is thoughtfully designed with its own private entrance, full kitchen, and full bathroom. Cozy and highly functional! Both units share a convenient laundry area located in the basement. Parcel has irrigation through the Talent district.

1872 Hope Street, Ashland
$649,000
220215348 MLS ⋅ 9,583 Sqft. Lot ⋅ 0.22 Acres
Ashland duplex built in 1996 with 2,831 SF and two well-designed units: one is a 1BD/2BA with office and one is a 2BD/2BA--an ideal setup for owner-occupancy or long-term investment. The main residence feels like a single-family home, offering a double garage, inviting foyer, vaulted ceilings, hardwood floors, granite counters, a spacious laundry room, and two gas fireplaces with one anchoring the living room and another in the primary suite. The primary bedroom also opens to a private deck, while the generous bathroom includes a soaking tub for an easy end-of-day retreat. A large view deck extends the great room, creating a comfortable indoor-outdoor flow for entertaining, morning coffee, or evening sunsets. The second unit features a functional single-level layout with two bedrooms, two full baths, and its own two-car garage, plus a tenant already in place, providing immediate rental opportunity. A rare Ashland property that blends space, privacy, and flexibility.

369 Alta Avenue, Ashland
$577,100
220212095 MLS ⋅ 4,791 Sqft. Lot ⋅ 0.11 Acres
Fully renovated historic home and detached cottage on a corner lot with alley access in the Skidmore Academy Historic District - just three blocks from Ashland's downtown plaza or one block to Briscoe Park! New foundation, roofing, sewer line, and utility services - including all electrical, gas, and plumbing. Single-level home with high ceilings, living room with crown molding, dining area with built-in china cabinet, kitchen with granite counters, stainless appliances including gas range with convection oven, two bedrooms with closet and built-in wardrobe - each with access to full ensuite bathroom with marble vanity and tiled tub shower. Charming period fixtures and vintage hardware throughout. Detached cottage with vaulted ceiling, vinyl plank flooring, sliding glass door to covered back porch, kitchenette with quartzite counter, and full bathroom with shower. Fully fenced backyard, mature trees, and off-street gravel parking for vehicles, boat, or RV. Inquire for details!

155 Central Avenue, Ashland
$925,000
220209916 MLS ⋅ 10,018 Sqft. Lot ⋅ 0.23 Acres
This beautiful Ashland triplex in the heart of the Railroad District, blocks from Food Co-op, theater and downtown, has a large .23 acre lot, plenty of parking and lovely historic curb appeal with modern amenities and upgrades. Currently owner-occupied, 254 has a large living area, a 2017 kitchen remodel, 2 bedrooms each with its own bath and laundry. 256 is a one bedroom w/ full kitchen, living area, bathroom and a patio with garden boxes. 252 is upstairs and was newly built in 2017. It is a permitted vacation rental with gorgeous high ceilings, large view windows, spacious kitchen, 2 beds, 2 baths and washer/dryer. Upgrades galore- tankless water heaters, new concrete pathway and parking for 4 cars, plus 1 RV & a sundeck. Whether you seek an investment property or a primary residence w/ a multi-generational layout, this beautiful home is a must-see. Buyer to perform their own due diligence regarding permitted uses & future possibilities.

252 B Street, Ashland
$695,000
220209197 MLS ⋅ 8,712 Sqft. Lot ⋅ 0.2 Acres
Excellent investment opportunity near downtown Ashland! This fully rented 4-plex is nestled in a quiet, desirable neighborhood. Each spacious unit features a main level living room, dining area, kitchen, laundry closet, and half bath. Upstairs includes two generously sized bedrooms and a full bath. Sliding doors lead from the dining area to private patios and small outside green space. Convenient alley access with paved off-street parking. Individually metered, tenants pay electric and water, owner pays some trash. Each unit has central heat/air. Great for 1031 exchange, small investment property. Fee appraisal in hand at asking price. Close to downtown, shops, restaurants, and all that Ashland has to offer!

330 High Street 1-4 Unit 1-4, Ashland
$615,000
220209104 MLS ⋅ 6,969 Sqft. Lot ⋅ 0.16 Acres
Motivated seller! Situated on a corner lot just minutes from downtown Ashland and SOU, this tastefully updated Victorian home offers two distinct living spaces and exceptional flexibility. The 1,024 sqft main level unit features , 3 bedrooms and 1 bathroom. Highlights include high ceilings, a remodeled kitchen and bathroom, luxury plank flooring, marble floors in the bathroom and laundry room, new windows, updated copper plumbing and electrical systems, and energy-efficient ductless heating and air conditioning. The 988 sqft upper-level unit offers 2 bedrooms and 1 bathroom. It includes a spacious living room with a gas heater, new luxury plank flooring in the kitchen, and bathroom. The large backyard provides space for gardening. A small shop offers additional storage or space for your creative projects. Live in one unit and rent the other, or lease both for income potential.

770 Iowa Street, Ashland
$1,010,000
220208620 MLS ⋅ 40,510 Sqft. Lot ⋅ 0.93 Acres
8-unit residential income property in Ashland on beautiful Park Street! Six 2 bed/1 bath units and two 3 bed/1 bath units. Lots of off-street parking. Each building has a 2 car-carport except the 3 bed/1 bath building there is a garage. Lovely open common area with trees and grass on this .93 of an acre property! All single level units. Units all have laundry rooms. All information is deemed reliable but not guaranteed. Buyers are advised to conduct their own due diligence. Price reflects condition.

635 Park Street, Ashland
$1,100,000
220206369 MLS ⋅ 6,969 Sqft. Lot ⋅ 0.16 Acres
Three units with median gross receipts over $100,000 per year in Ashland's Railroad District! The charming and thoroughly updated Second Street Cottages feature two furnished and permitted vacation rentals along with a spacious and comfortable owner's suite — each with full kitchen, central air conditioning, gas furnace and water heater, separate laundry facilities, double-paned windows and sliding glass doors to private fenced and gated outdoor spaces. Heritage House has four bedrooms and three full baths, large front porch, original fir floors, and operable Velux skylights. Garden Cottage has two bedrooms and two full baths, vaulted ceilings, oak floors, quartz and granite counters, and new kitchen appliances. The owner's Hideaway Suite has two separate exterior entrances, full main-level bath, office or formal dining, pantry, upper-level bedroom with full ensuite bath and ample closet storage. Accommodations featured on top booking sites in Ashland. Inquire for details!

144 N 2nd Street, Ashland
$625,000
220205786 MLS ⋅ 5,662 Sqft. Lot ⋅ 0.13 Acres
A rare opportunity located in Ashland's beloved Railroad District! This charming & versatile property offers 3 separate units just blocks from the Co-op, OSF, & downtown Ashland. Lovingly maintained, the property blends timeless character w/ modern functionality & includes newer sewer & water lines, electrical panel, & window coverings. The main unit offers a spacious 2-bedroom layout w/ stunning wood accents & built-ins throughout. The kitchen is conveniently located next to the dining area & has its own laundry facility. Unit #2 is a 1-bedroom apartment w/ a galley kitchen + great natural light. Unit #3 is a charming studio. Large fenced yard w/ mature landscaping, garden space, deck + 4 alley off street parking spaces. Whether you seek a primary residence with added flexibility, a multi-generational layout, or a unique investment opportunity, this one-of-a-kind property is full of potential. Buyer to perform their own due diligence regarding permitted uses and future possibilities

237 B Street, Ashland
$925,000
220205870 MLS ⋅ 9,583 Sqft. Lot ⋅ 0.22 Acres
971, 975, and 977 Siskiyou Blvd. Extremely hard-to-find Ashland three unit property! Unit 1) 1940 built - 1713 sf single level with 3 beds and 2 baths completely remodeled from the ground up in 2018. Units 2 & 3 - 2018 built - detached duplex with 875 sf on each side. Each unit includes 1 bedroom and 1.5 baths. The light filled duplex has vaulted ceilings, stainless steel appliances, and vinyl wood plank flooring. The upper level is entirely devoted to the owner's suite with a loft style bedroom, full bath, bonus space, and a walk-in closet. The property includes separate electrical meters for all units and a large private parking area across from Southern Oregon University. All three units are currently rented with monthly income totaling $5,350. The listing photos were taken in 2018 at the completion of the house remodel and duplex new construction.

971 Siskiyou Boulevard, Ashland
$550,000
220205577 MLS ⋅ 9,147 Sqft. Lot ⋅ 0.21 Acres
Attention Investors or 1st time home buyers. This one just got better! This Duplex has income potential all over it. A large lot with mature trees, located on a quiet street near the hospital. A rare find is that this property also has TID water rights for outside yard care. Both units have been remodeled with major upgrades including HVAC mini-splits systems for maximum efficiency and each with over 900 sq ft. Unit 682 has 2 bedrooms with a lower bonus room. Unit 684 has just been refreshed this month and ready for a brand-new tenant or move in yourself. Includes new plank flooring, new countertops with an additional wood block counter as well. The cabinets have just been painted and look fantastic. Each unit has indoor laundry hookups, private decks with mountain views and their own fenced yards. Other recent upgrades are exterior paint 2024, new roof 2019, newer water heaters 2019 & 2022. Decks were rebuilt in 2014.

682 Chestnut Street, Ashland
$650,000
220203741 MLS ⋅ 8,712 Sqft. Lot ⋅ 0.2 Acres
Comp Only - this information is for statistical purposes only.

132 Van Ness Avenue, Ashland
$483,500
220201290 MLS ⋅ 6,534 Sqft. Lot ⋅ 0.15 Acres
Rare opportunity to own a clean and neat duplex in Ashland. Located between Ashland High School and Southern Oregon University, this single-level duplex sits at the quiet corner of Iowa Street and Wolfard's Alley. The two units are mirror images of each other, with two bedrooms, one bath, a large living room, a separate kitchen/eating area, and its own one-car garage with laundry facilities. The duplex is set back from the street, with mature trees, a fenced yard with lawn, and off-street parking. Easy access to schools, shopping, public transit and all that Ashland offers. Quiet neighborhood makes this an ideal setting. The property has stable tenants and has been a solid producer for years. Rental properties like this don't come on the market very often. Seize this opportunity to own a consistently rented duplex in the heart of Ashland.

1208 Iowa Street, Ashland
$955,000
220198643 MLS ⋅ 7,405 Sqft. Lot ⋅ 0.17 Acres
This property is ideally located in a prime commercial district, just a few blocks from Ashland Public Library and within close proximity to major city attractions. The main house is a charming 2-bedroom, 1-bath Craftsman-style home featuring a fireplace insert and fir floors. The triplex includes Unit #2 and Unit #3, both offering loft-style bedrooms with 20-ft cedar-lined ceilings and skylights that brighten the living spaces below. Each unit also has a small office/bedroom on the main floor, a full kitchen, and a bathroom with a shower/tub. Unit #4 is a single-level unit with a vaulted cedar ceiling and skylight, allowing ample natural light. The house, Unit #2, and Unit #4 all come with a washer/dryer. The owner could live in the main house while renting out the triplex for additional income.

574 E Main Street, Ashland
$425,000
220197266 MLS ⋅ 15,246 Sqft. Lot ⋅ 0.35000000000000003 Acres
So much potential on Main Street! Bring your vision and your contractor! This is one of those rare finds! Currently a 6 unit array of unique, historical abodes. Located in the Skidmore Historic District. Conveniently located close to downtown on a 1/3 acre lot. Renovate? Build new? or a combination of both? Here is an opportunity for your creative team! Check with the City for building options/density bonuses etc.

431 N Main Street, Ashland
$750,000
220194422 MLS ⋅ 14,810 Sqft. Lot ⋅ 0.34 Acres
Sold Only. Duplex and single family home.

223 W Hersey Street, Ashland
$272,000
220190474 MLS ⋅ 7,405 Sqft. Lot ⋅ 0.17 Acres
Two-story duplex. Both two bedroom one bath units. Investment opportunity to be purchased with 721 N Main. Property provides easement and has shared parking with 12-plex.

715 N Main Street, Ashland
$1,328,000
220190475 MLS ⋅ 27,878 Sqft. Lot ⋅ 0.64 Acres
Great investment opportunity. 12-plex - all two-bedroom one bath units. Solid build. Downstairs units with backyards. On-site laundry room and additional storage area for each unit. Ample off-street parking.

721 N Main Street, Ashland
$648,175
220190209 MLS ⋅ 6,534 Sqft. Lot ⋅ 0.15 Acres
Charming multiplex super close to downtown Ashland with excellent income, lots of off street parking and mature trees. The two units in front have great craftsman-style curb appeal with covered painted concrete porches. Both front units have 805 sqft, 1 bedroom, 1 bathroom, large laundry room with sink, open great room with kitchen, dining room and living room, laminate wood & vinyl flooring, vinyl windows. Kitchens have laminate countertops, pantry, gas range, breakfast bar, and lots of cabinets. The dining rooms have a lovely original built-in hutch. The studio in the back has a covered front patio, kitchenette, vaulted ceilings, and access to a fenced back yard. Storage shed and appliances included. Separate electric and water meters. Off-street parking for 3+ cars off of alleyway in the back plus lots of room for on-street parking in the front on Helman Street. Concrete pathways and lawn space around the property. Currently leased by OSF.

145-149 Helman Street, 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: