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$419,000
2 Beds 1 Baths 220222831 MLS 1,253 SqFt. 8,276 Sqft. Lot 0.19 Acres
Charming 2 bdrm, 1 bath home with large great room. Original hard wood floors. Gas brick fireplace and brand new appliances. Large windows & skylights throughout make this a light filled home. Kitchen remodeled in 2010 with handcrafted cabinetry, soft close drawers & granite counter tops. Custom tile & river rock in bathroom shower. Mini duct heating & air. Great room features 3 sliding glass doors, 3 skylights. Enter the backyard & find an urban homestead environment with fruit trees and a pond. Also in the garden, an insulated 8x10 room that could be used for an office, a magical 2 story playhouse with large windows, is insulated & has electricity. Playground w/swing set & monkey bars. Storage shed with covered deck and separate tool shed. Fully fenced. New roof in 2017. Lots of storage & parking space. R-2 zoning. Conveniently located with Southern Oregon University, public pool, Garfield Park, tennis courts, middle school & elementary schools within blocks.

1312 Iowa Street, Ashland

$400,000
2 Beds 1 Baths 220222433 MLS 1,630 SqFt. 11,325 Sqft. Lot 0.26 Acres
Charming historic fixer-upper on a private 0.26-acre lot with mature trees and incredible pollinator garden featuring 70+ plant species, lovingly cultivated over 30 years. New roof in 2019, new fencing in 2012, and new central ducting with gas furnace in 2006. Living and dining with solid oak floors and glass door to front office. Kitchen with antique gas stove, butcher block and tile counters, operable casement bay windows, wood and glass display cabinets, double sink with updated hardware, under-sink water filtration, and new dishwasher in 2023. Spacious main-level bedroom with closet, full bathroom with clawfoot tub shower, and sitting room with stairs to vaulted upper bedroom with closet. Backyard with deck and hot tub, raised beds, perennials, detached garage shop with alley access, and excellent potential for ADU or second dwelling. Centrally located above the boulevard in the desirable Siskiyou-Hargadine District near Triangle Park. Bring your ideas and inquire for details!

324 Liberty Street, Ashland

$1,000,000
220222324 MLS 5,662 Sqft. Lot 0.13 Acres
Unique opportunity in downtown Ashland. This commercial property offers two legal spaces with strong flexibility. 120 E Main features 1,520 sq ft plus an expansive deck--ideal for retail, office, hospitality, or possible restaurant use. 130 E Main adds 369 sq ft, well-suited for a boutique, studio, or office. Zoned C-1-D, allowing a variety of uses. Built in 1938, the building blends character and functionality with tile and hardwood floors and a convenient single-level layout. Alley access and designated parking add ease and functionality. Ideal for an owner-occupant--occupy both spaces, use one and lease the other, or maximize income by renting both. Prime location with strong visibility, steady foot traffic, and close proximity to downtown shops, dining, and everyday amenities.

120 E Main Street, Ashland

$1,250,000
2 Beds 2 Baths 220222210 MLS 2,224 SqFt. 6,969,600 Sqft. Lot 160 Acres
Rare opportunity to own 160 private acres on the outskirts of Ashland, offering extreme end-of-the-road seclusion, breathtaking panoramic views, and endless potential for recreation, hunting, and homesteading. Surrounded by nature and abundant wildlife, this remarkable mountain retreat delivers the peace and privacy that are increasingly difficult to find. Located just 30 minutes from Mt. Ashland and approximately 45 minutes to downtown Ashland, the property offers the perfect balance of remote living and convenient access to dining, culture, and outdoor adventure. The custom-built home features a stunning great room that truly must be experienced in person, with soaring ceilings, warm finishes, and walls of windows framing the surrounding landscape. A spacious primary suite, inviting guest accommodations, large barn, and substantial shop space make this property ideal as a full-time residence, legacy ranch, or unforgettable weekend mountain escape.

1969 Colestin Road, Ashland

$958,055
2 Beds 3 Baths 220222159 MLS 2,331 SqFt. 25,264 Sqft. Lot 0.58 Acres
Iconic architectural masterpiece designed by Donald Fairweather, a Frank Lloyd Wright fellow who studied at Taliesin. Sitting just above downtown Ashland, it is hard to describe the soul of this home without setting foot inside. Clad in vertical-grain redwood and featuring floor-to-ceiling windows, this home nestles beautifully into its natural surroundings. Inside, one is immediately met with the warmth of the materials and space. The beautifully updated kitchen is a chef's dream and connects to a lovely dining area and family room. The living room is the highlight, with windows on three sides, vaulted ceilings, redwood built-ins, and a large fireplace that adds warmth. It enjoys incredible views of the Cascades and begs to be enjoyed from inside or from the expansive deck. Two primary suites on opposite ends of the home. Both have updated en suite baths. Only a short jaunt from Lithia Park and downtown Ashland, this may be the last chance in a long time to own this architectural ge

155 Terrace Street, Ashland

$965,000
7 Beds 5 Baths 220222015 MLS 2,790 SqFt. 8,712 Sqft. Lot 0.2 Acres
Rare opportunity to own 2 residences plus a studio on one tax lot. Offers exceptional flexibility for multigenerational living, rental income, live-work, or guest accommodations. The 1,720 SF main residence was fully renovated in 2018, including a new poured foundation, and has 4 bedrooms, 2 baths, open living spaces, a kitchen with crisp white cabinets, subway tile backsplash & a main level bedroom. The main residence includes a double garage with a 480 SF upper-level studio with a full bath. A separate second 1,070 SF residence, built in 2018, offers stylish & charming single-level living with high ceilings, 2 bedrooms, 2 baths, & contemporary finishes. Situated in an established historic neighborhood with mature trees, the property has off-street parking, modern systems, and is close to Ashland's downtown. This R-2-zoned property features separate addresses & meters & allows for 2 Airbnb units with owner occupancy on premises. Request property offering details.

563 Rock Street, Ashland

$665,000
4 Beds 3 Baths 220222013 MLS 2,570 SqFt. 5,227 Sqft. Lot 0.12 Acres
Cherished historic Queen Anne Victorian with detached office shop in the heart of Ashland's historic Railroad District. Comprehensive improvements over 28 years include a fully permitted and historically compatible remodel addition, new roof, upgraded foundation, insulation, HVAC, electrical, plumbing, and new sewer line. Period fixtures, vintage hardware, and solid oak hardwood flooring throughout. Main level with entry foyer, original pocket doors, living room with bay window, formal dining room, spacious kitchen with walk-in pantry, enclosed porch utility room with sliding glass door to covered composite deck, full bathroom with vintage clawfoot tub shower, and bedroom with closet. Three upper-level bedrooms with closets, full bathroom with double vanity and operable skylight, and landing sitting room. Detached office with ceiling fan, full bathroom with shower, shop with skylight, and double doors to poured concrete parking area with alley access. Inquire for details!

138 Third Street, Ashland

$820,000
4 Beds 3 Baths 220221540 MLS 2,344 SqFt. 17,859 Sqft. Lot 0.41000000000000003 Acres
A beautifully updated home on nearly a half-acre in one of Ashland's desirable Above-the-Boulevard neighborhoods. Fully rebuilt to the studs in 2002, this 2,344 sq foot home features 4 bedrooms and 3 baths. The main level has 3 bedrooms and an office, including the private primary suite with remodeled bathroom and direct access to the hot tub and outdoor shower. The 4th bedroom downstairs has its own full bath and private entrance. The open-plan living room and kitchen feature a center island, built-in bookcases, vaulted ceiling, skylights and generous windows. The home is highly efficient with solar, radiant heat in every room and whole house fan. Enjoy outdoor living on the patio off the kitchen with a lovely water feature. The private grounds include mature fig, apple, pear, cherry, persimmon, almond and peach trees for harvesting all season long. Expansive irrigated raised beds, tons of storage and a partial basement that's perfect for a small shop. Don't wait on this one!

610 Beach Street, Ashland

$794,000
5 Beds 6 Baths 220221349 MLS 1,616 SqFt. 9,147 Sqft. Lot 0.21 Acres
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

$550,000
4 Beds 2 Baths 220221283 MLS 1,956 SqFt. 8,712 Sqft. Lot 0.2 Acres
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

$599,000
4 Beds 3 Baths 220220812 MLS 2,485 SqFt. 10,018 Sqft. Lot 0.23 Acres
Timeless mid-century home just a block above Lithia Park and only a short jaunt to the plaza. Sitting in a quiet location with views, this home offers serenity while still being close in. Exposed beam ceilings on the lower level offers warmth and charm. A bank of picture windows in the living room allows one to take in the mountain views as well as overlooking the backyard. The kitchen opens to the spacious back deck which is perfect for entertaining and indoor/outdoor living. An oversized mudroom/pantry as well as an office nook round out the downstairs. Upstairs sit 4 bedrooms, including a spacious primary suite that opens to a private deck with views to take in the natural beauty. One bedroom with vaulted ceiling could be used as a media room or flex space. Outside, the yard is fully fenced and has garden beds and room to play. With a solar array and backup battery, this home is well-equipped. All of this is so close to town, Lithia Park and the incredible trail network of Ashland!

34 Scenic Drive, Ashland

$500,000
2 Beds 2 Baths 220220776 MLS 1,440 SqFt. 6,534 Sqft. Lot 0.15 Acres
Charming 1915 cottage-style home in the heart of Ashland, set on a beautiful tree-lined street close to downtown, restaurants, parks and the OSF campus. With 1,440 sq ft, 2 bedrooms and 2 full baths, this home blends historic character with thoughtful updates. Original wood floors, high ceilings, period moldings and an open floor plan create an inviting feel. The eat-in kitchen features tile counters and custom cabinetry, and the main-level primary suite opens to a peaceful backyard deck. Upstairs offers a second bedroom and full bath, creating nice separation of space. Remodeled in 2000 by respected local craftsman Brad Roup. Partial basement provides extra storage. The 0.15-acre R-2 zoned lot is a true garden oasis with dogwoods, redbud, maple, lilacs, irises, peonies, roses, apple tree, fig tree and more, all served by an operating irrigation system. New roof in 2025; exterior painted in 2015.

200 Harrison Street, Ashland

$245,000
2 Beds 2 Baths 220220712 MLS 880 SqFt.
If you are looking for the best views in Ashland's Tudor Heights, this is it. Positioned as the premier front unit, this condo offers a perspective no other home in the complex can match. Stay comfortable year-round with the rare addition of efficient ductless mini-splits for heating and cooling--a significant upgrade over the standard baseboard heat found in most units. The main level offers a seamless open layout that flows to your outdoor patio. Upstairs, both bedrooms provide unobstructed mountain views to the north and east, including a private balcony off the main suite--perfect for watching the sunrise. Whether you're walking to the Downtown Plaza for dinner or hiking through Lithia Park, everything is within reach. Enjoy the security and ease of a comprehensive HOA that handles exterior upkeep, allowing you to simply relax and enjoy the Southern Oregon scenery.

495 Chestnut Street 1 Unit 1, 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

$215,000
2 Beds 2 Baths 220219913 MLS 832 SqFt.
Charming Ashland Condo in Prime Location! Conveniently situated near restaurants, shopping, medical facilities, & scenic hiking trails in beautiful Lithia Park, this inviting 2-bedroom, 1.5-bathroom condo offers both comfort & accessibility. Tucked toward the back of the desirable Tudor Heights Complex, updated w/ newer carpet, LVP flooring & exterior paint. The main level features a kitchen w/ refrigerator, range/oven, & microwave, plus a convenient half-bathroom. Living room opens to a covered back patio, perfect for enjoying your morning coffee. Upstairs, you'll find 2 bedrooms--one w/ a private balcony ideal for relaxation, the other w/ a walk-in closet & easterly mountain views. Full bathroom w/ a dual sink vanity & tub/shower combination. The HOA provides many amenities, including a covered assigned parking space w/ storage closet, water, sewer, garbage, roof maintenance, exterior upkeep, & common areas. Don't miss your opportunity to start enjoying the Southern Oregon Lifestyle!

495 Chestnut Street 19 Unit 19, Ashland

$375,000
2 Beds 1 Baths 220219842 MLS 886 SqFt. 4,791 Sqft. Lot 0.11 Acres
Charming single-level cottage in one of Ashland's most desirable locations, with stunning views of Grizzly Peak. This clean, well-maintained home features new flooring throughout and an inviting, light-filled interior, with two bedrooms plus a detached bonus room (not included in sq. footage), perfect for home office or studio. Additional storage can be found in the spacious basement. Large undeveloped adjoining lot (not included in the sale) gives the property a feeling of openness and privacy. Among the cherry and apple trees, grapevines and herb garden, enjoy peaceful mornings on the porch, a perfect spot for coffee while taking in the quiet neighborhood. Ideally located close to downtown Ashland, Lithia Park, the Oregon Shakespeare Festival, Southern Oregon University, dining, and nearby hiking and biking trails.

480 Harrison Street, Ashland

$718,150
2 Beds 2 Baths 220219778 MLS 1,508 SqFt. 139,392 Sqft. Lot 3.2 Acres
Bucolic setting on 3.2 acres with panoramic views. This is an incredible property with a wonderful single-level home and a separate guesthouse. The main house has a wraparound deck that takes in mountain and vineyard views. Inside is an open floor plan with newly finished oak floors that create a wonderful flow. The living room has floor-to-ceiling picture windows and a wood stove that provides both heat and ambiance. There are two large bedrooms with two full bathrooms, set apart from the living space, creating a nice separation. The detached guest house, 216 sqft, is perfect for guests or extended family and overlooks the quaint pond fed by Neil Creek. The current owner has been producing wine, and there are Merlot, Cab, and Zinfandel grapes. There are several other outbuildings that include a studio, shop, small barn, and storage- truly a compound for country living, yet still just minutes to downtown Ashland and at the gateway to wonderful outdoor activities in the area.

750 Neil Creek Road, Ashland

$570,900
3 Beds 2 Baths 220219499 MLS 1,728 SqFt. 10,018 Sqft. Lot 0.23 Acres
This beautiful home above the Boulevard, is in a very sought after location in Ashland. It has been updated inside with designer interior paint and wallpaper, new European appliances, Italian tile gas fireplace, imported French draperies, and gorgeous custom lights. There are three bedrooms, two bathrooms, large deck off the dining room, and a detached workshop with 110 and 220 power. There are charming built-in bookcases and a comfortable window seat in the living room. The gardens are truly amazing with mature magnolia tree, Japanese maple ornamental, and gorgeous crabapple tree, plus over 100 rose bushes and perennials. There is TID irrigation for the property, and a garden area plus greenhouse/potting shed in the backyard. It is a spacious and private corner lot with deer proof fencing and is in an established neighborhood. The seasonal blooms and beautiful colors will welcome you into this very special home.

945 Hillview Drive, Ashland

$260,000
2 Beds 2 Baths 220219424 MLS 1,102 SqFt.
Sweet condo, lovely interiors, & low-maintenance living just moments from the heart of Ashland. This charming 2-bedroom home is perfect for a simplified lifestyle -- the HOA covers all exterior maintenance & groundskeeping. Tucked in a quiet setting overlooking a lush lawn with mature trees, this desirable corner unit offers wonderful natural light & an open, contemporary floorplan. Stylish & welcoming inside -- open living area, kitchen with granite counters & dining bar, tile-floored living room, & access to a rear fenced patio. Bedrooms are nicely sized, one featuring a Murphy bed & sunny window seat. Bathrooms are updated with custom tile. Year-round comfort courtesy of high-efficiency mini-splits. Dedicated covered parking & private storage included. Fully furnished if buyer wishes -- negotiable. HOA may allow rentals subject to approval; buyer to verify. Onsite laundry room. Value, location, & ease of ownership. Barely lived in by out-of-area owner. This one is ready for you.

495 Chestnut Street 16 Unit 16, Ashland

$775,000
3 Beds 3 Baths 220219338 MLS 2,158 SqFt. 10,018 Sqft. Lot 0.23 Acres
Located in a prime neighborhood, close to downtown Ashland. Open concept design showcases beautiful hardwood flooring, skylights fill the space w/ abundant natural light, a stone-surround gas fireplace w/ mantle & custom built-ins. The kitchen is thoughtfully designed w/ stainless steel appliances, concrete & PaperStone countertops, tile backsplash, heated tile flooring + bar seating. The spacious primary suite features a well-appointed ensuite w/ a soaking tub, tile shower, dual sinks & direct access to the front decks, perfect for taking in expansive mountain views. Upstairs you'll find two additional generously sized bedrooms + a full guest bath. There is a dedicated laundry room + a large mud room w/ sink leading to the backyard. The backyard is fully fenced, w/ mature landscaping, a shed, swing set, gas fire pit plus a concrete stone patio w/ hot tub. Out front you'll enjoy an oversized deck + a fenced garden area w/ raised beds. New interior paint. This is a true Ashland gem.

301 Hillcrest Street, Ashland

$457,624
3 Beds 2 Baths 220219314 MLS 1,120 SqFt. 6,969 Sqft. Lot 0.16 Acres
Charming home just minutes from downtown Ashland, schools, Garfield Park, and the bike path. This period property blends classic character with thoughtful updates, including modern finishes, a newer roof, and an efficient heat pump. An enclosed front porch welcomes you into a bright living room that flows seamlessly into a spacious kitchen featuring white cabinetry, granite countertops, and stainless steel appliances. The main level offers two bedrooms, including one with an ensuite half bath, while the upper level provides a third bedroom and a versatile loft space ideal for an office, studio, or media room. The extra-deep backyard is a standout feature, complete with a deck, garden beds, mature trees, a chicken coop, a garden shed, and a large shop or studio. R-3 zoning offers added flexibility and potential for future development.

140 Lincoln Street, Ashland

$475,000
2 Beds 2 Baths 220219308 MLS 1,440 SqFt. 6,969 Sqft. Lot 0.16 Acres
Perched on a corner lot framed by five mature Deodar cedars and a striking giant sequoia, this thoughtfully maintained home offers treetop outlooks and filtered glimpses of the Rogue Valley. The main level features large windows, hardwood floors, and a living area with fireplace. A deck extends the living outdoors. Downstairs offers a flexible primary suite with open-concept bath, freestanding soaking tub, mosaic tile wet area, and radiant heated floors, a design-forward blend of bedroom and spa-inspired living. The separation between levels offers potential for multigenerational living, extended guest use, or rental flexibility. Major updates include sewer lateral (2022), roof (2013), exterior paint (2023), and professional tree pruning (2026). Deer-fenced yard with dual pedestrian gates and rear vehicle access. Conveniently located in Ashland, this home balances setting, privacy, and character.

621 Altamont 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: