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$2,500,000
5 Beds 7 Baths 220220624 MLS
Discover this extraordinary Southern Oregon Luxury 2 acre estate perched above downtown Ashland w/views & incredible privacy. This custom built Pagnini home 5313 SQ FT, 5 bdrms, 5.5 bthms, 5 Car Garage + an additional 720 sq ft detached guest quarters. Grand entry, stunning wood floors, soaring ceilings, multiple fireplaces & walls of windows to take in the incredible views & abundant natural light. Gourmet kitchen w/quartz countertops, skylights & SS appliances w/double ovens. Main level primary suite w/ terrace access offers a soaking tub & steam shower. 2 upstairs guest suites both come complete w/private balcony & breakfast bar. Additionally this incredible home features a slate roof, sauna, elevator, a spacious office w/ en-suite + so much more. European-style terrace w/big natural boulders, fruit trees, a dog run, greenhouse, and manicured gardens along w/ abundant wildlife- no expense was spared on this remarkable Ashland retreat & it truly shows

500 Ashland Loop Road, Ashland

Listing courtesy of John L. Scott Medford.

$715,000
3 Beds 3 Baths 220221008 MLS
Back on the market through no fault of the property! Custom-built home on a private .69-acre lot in Ashland with breathtaking valley and mountain views. This versatile property offers a primary bedroom on the main level, vaulted ceilings, fireplace, built-ins, and spacious living areas designed for comfort and entertaining. Large kitchen with breakfast nook and abundant storage throughout. The primary suite features double sinks, separate shower, and a jetted soaking tub with its own hot water system. Downstairs includes a finished daylight basement with separate entrance and plumbing in place ideal for guest quarters, multi-generational living, or future mother-in-law suite potential. Enjoy the fenced garden with raised beds, TID irrigation water, oversized 2-car garage, easy-care landscaping, and a new roof installed in 2023. Rare blend of privacy, flexibility, and stunning views.

1020 Walker Avenue, Ashland

Listing courtesy of Oregon Adventure Realty.

$935,000
3 Beds 3 Baths 220220668 MLS
Quality custom view home in a private natural setting above the boulevard, just six minutes to Ashland's downtown plaza. Abundant natural light and airflow with operable wood-wrapped casement windows, high vaulted ceilings, solid core doors, and unique architectural view corridors throughout. Great room with solid Brazilian cherry flooring, gas fireplace, formal dining with built-in buffet, French doors to wrap-around view deck, kitchen with granite dining counter and stainless appliances, open family and informal dining room, powder room, laundry with utility sink, and two-car garage. Step-down primary suite with French doors to private balcony, walk-in closet, full ensuite bathroom with travertine double vanity, jetted tub, shower, and water closet. Upper loft with mountain views and stairwell skylights. Two lower-level guest bedrooms, full bath with tub shower, den, and French doors to pebbled concrete patio and organic garden. Newer HVAC and exterior paint. Inquire for details!

602 Ashland Street, Ashland

Listing courtesy of John L. Scott Ashland.

$795,000
220220422 MLS
Back on market at a new price -- 3.57-acre build-ready E-1 (Employment) parcel at the south gateway to Ashland's primary commercial corridor. Flat, fully unimproved, with full City utilities, FEMA Zone X, and frontage on two public streets (190 ft Jefferson Ave, 868 ft Washington St). E-1 allows broad use: distribution/warehouse, light manufacturing, retail, office, and institutional. Under the R-Overlay, up to ~53 mixed-use residential units by right over ground-floor commercial. Set in an established distribution corridor with long-tenured operators nearby -- a proven warehouse/industrial location with flexibility for other uses. I-5 Exit 14 ~1.1 mi; private rail-spur feasibility confirmed (see docs, estimate only). Priced 43% below the adjacent 777 Jefferson sale; very favorable seller financing available. Buyer to verify intended uses with City of Ashland (Code 18.2.2.030). Contact listing agent for details.

799 E Jefferson Avenue, Ashland

Listing courtesy of Coldwell Banker Commercial Professional Group.

$375,000
2 Beds 1 Baths 220219842 MLS
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. Lease-to-own possibility with down-payment.

480 Harrison Street, Ashland

Listing courtesy of Millen Property Group.

$149,000
220219767 MLS
Exceptional opportunity to acquire a fully operational second-generation restaurant in Ashland, OR. The business is generating strong revenue ($350K+ in 2024) with established infrastructure and consistent operations in place. Fully equipped with commercial kitchen infrastructure including Type-1 hood, walk-in cooler, grease trap, wok range, tandoori oven, and POS system. All FF&E is included, offering a true turnkey transition for a new operator. New lease structure offers significant value, including tenant improvement allowance and initial rent abatement, reducing upfront capital requirements. Property also includes approx. 600SF of on-site residential space, providing a unique advantage for owner-operators or employee housing in Ashland's constrained rental market. Ideal for owner-users or operators seeking a ready to go restaurant location with immediate income potential.

1667 Siskiyou Boulevard, Ashland

Listing courtesy of Coldwell Banker Commercial Professional Group.

$575,000
5 Beds 3 Baths 220219281 MLS
NEW PRICE! Seller is offering $10k towards repairs or buy downs! 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

Listing courtesy of Cascade Hasson Sotheby's International Realty.

$1,466,000
2 Beds 4 Baths 220218853 MLS
You'll be in a prime spot right in Ashland's Railroad District/Spur Rail Subdivision, a super desirable area! Just hop on the elevator to the top! This place has a fantastic modern design, with 770 square feet of first-floor commercial space and a luxurious 2-story home on the 2nd and 3rd floors. You'll find premium finishes everywhere, a huge rear patio, vaulted ceilings, big windows, an open floor plan, and materials that are easy to take care of, so they last. Plus, the property is set up to get the most out of solar panels. You'll have amazing views of Grizzly Peak to the north and Mt. Ashland to the south--it's truly a dream location. The property is zoned E1 commercial (Ashland Employment District with Residential Overlay). There's a single-car garage, EV charging, and the square footage has grown. The windows have also been upgraded to Milgard Fiberglas;, each parcel comes with a 1/6th interest in the parking lot next door.

138 Clear Creek Drive, Ashland

Listing courtesy of Millen Property Group.

$2,500,000
220217226 MLS
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

Listing courtesy of Bespoke Real Estate.

$855,000
220217221 MLS
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

Listing courtesy of RE/MAX Integrity.

$675,000
4 Beds 3 Baths 220216451 MLS
Panoramic valley views, seconds from Downtown Ashland & Lithia Park - a rare combination of space, quality, and location. This 4-bedroom, 3-bath home offers 2,711 sqft on a private 0.26-acre lot. The vaulted living room features hardwood floors that continue throughout both levels, and nearly every room captures sweeping valley views. Two large decks extend the living space outdoors. The updated primary suite includes radiant floor heating, walk-in shower, soaking tub, and dual vanities. The galley kitchen offers granite countertops, custom cabinetry, and quality appliances. Detached sauna/private office, EV-equipped 2-car garage, wood stove, and tankless water heater. Shared private cul-de-sac with two neighbors - the approach is short and the privacy at the top is exceptional. Walkable to Lithia Park, the Oregon Shakespeare Festival, and downtown Ashland. Pre-inspection completed. 1-yr home warranty included. At $249 per sq ft, priced below comparable 2026 Ashland sales.

211 Glenview Drive, Ashland

Listing courtesy of John L. Scott Medford.

$750,000
220216441 MLS
Versatile commercial building in the heart of downtown Ashland - surrounded by retail and restaurants, within one block of the Oregon Shakespeare Festival! Eight tenant suites with an established mix of professional and personal services, restaurant, and hair salon. Main level features a 55' x 10' breezeway to Will Dodge Way, three individual suites, and one common area bathroom. Upper level with five additional suites, full commercial kitchen, two additional shared bathrooms, and storage closets. High-traffic location with excellent visibility and ample public parking directly across Lithia Way. Recent appraisal of income and comparable sales with market value opinion available. Inquire with agents to access additional documentation and details!

116 Lithia Way, Ashland

Listing courtesy of John L. Scott Ashland.

$499,000
4 Beds 3 Baths 220216358 MLS
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

Listing courtesy of Ashland Homes Real Estate Inc..

$325,000
1 Beds 1 Baths 220215889 MLS
This 1 br/1bath 2nd-floor corner condo greets you w/ sunlight pouring through generous windows, illuminating the inviting finishes that give the space its timeless, easy charm. Its open floor plan unfolds naturally, with the living area flowing into the kitchen with abundant counter space, ample storage, & brand-new appliances waiting to be used for the very first time. You'll love spending your mornings on your private balcony gazing out toward the Cascade Mountains as the light shifts across the peaks. Even workdays feel lighter here, thanks to a dedicated office nook that keeps productivity close to comfort. With its own dedicated laundry area & built-in storage, even the practical parts of life feel organized & beautifully tucked away. Perfectly located minutes from downtown Ashland, the Oregon Shakespeare Festival, shopping, dining, & scenic hiking/ biking trails -- with quick access to I-5 & just 30 minutes north of the California state line -- you're moments from everything!

2205 Ashland Street 210 Unit 210, Ashland

Listing courtesy of Bespoke Real Estate.

$255,000
2 Beds 2 Baths 220214906 MLS
Nestled within a quiet, well-kept complex, this charming 960 sq ft end-unit condo, built in 2002, offers a comfortable blend of privacy and convenience. The home features 2 bedrooms & 2 full baths, a generously sized laundry & pantry room, a dedicated dining area, & an inviting living space ideal for everyday living. The kitchen is well appointed with abundant cabinetry for storage, & a stackable washer and dryer are included. The primary bedroom offers a peaceful retreat w/an ensuite bath and spacious closet, while a second bedroom & full bath provide flexibility for guests, a home office, or creative pursuits. Situated on the 2nd floor w/no neighbors above & only one adjoining unit, the condo enjoys a sense of calm & seclusion. A one-car garage & large storage unit add practicality, while the location--close to shopping, Southern Oregon University, restaurants, and scenic hiking trails--makes this affordable Ashland home especially appealing.

790 Park Street, Ashland

Listing courtesy of Windermere Van Vleet & Associates.

$785,000
4 Beds 4 Baths 220211772 MLS
Tucked away on a quiet, tree-lined street, this beautiful home strikes the perfect balance of space, comfort, and mountain charm. Boasting 3,404 square feet, 4 bedrooms (plus an office) and 3 bathrooms, it offers plenty of room for both relaxation and entertaining. The open main level flows easily from the spacious living and dining areas to a warm, inviting kitchen with rich wood cabinetry, generous counter space, and windows that frame peaceful forest views. New front and rear cedar decks (2022) extend your living space outdoors, perfect for morning coffee or evening gatherings. The lower level hosts the primary suite and three additional bedrooms, three with private deck access and peaceful vistas. A large basement provides easy access to nearby trails and could be finished for extra living space, while also offering convenient access to the home's major systems. With a clean pre-listing inspection and thoughtful updates throughout, this home truly embodies refined mountain living.

461 Waterline Road, Ashland

Listing courtesy of John L. Scott Ashland.

$2,900,000
220211191 MLS
PRICE REDUCED-$2,900,000. A rare opportunity to acquire ±9.71 acres of prime, developable land within Ashland's adopted Normal Neighborhood Plan, the city's designated area for sustainable, mixed-use growth. Three contiguous parcels with direct East Main Street frontage lie just outside city limits yet within the Urban Growth Boundary, contiguous to existing city limits and services -- the only parcel in the Plan area with stand-alone annexation-readiness in the chain of contiguity, providing a clear, efficient path to Type III annexation. The City may establish an Advance Financing District (AFD) to help offset infrastructure costs such as sewer oversizing and frontage improvements, reducing upfront expense. The site also carries the only commercial overlay (NN-1-3.5-C) in the entire 93-acre Plan area. With utilities at frontage and anticipated zoning of NN-1-5, NN-1-3.5, and NN-1-3.5-C, the assemblage suits a blend of residential and neighborhood-scale commercial uses.

2082 E Main Street, Ashland

Listing courtesy of Coldwell Banker Commercial Professional Group.

$850,000
4 Beds 4 Baths 220209966 MLS
Quality built contemporary home placed among the madrone and pine trees in the hills of beautiful Ashland OR. Versatile, user-friendly floor plan with many unique architectural features. The cozy living room w/ fireplace, kitchen and dining area surround a well-designed multi use pantry closet. Soaring open beam ceiling above leads to a wall of windows allowing for natural light and views of the trees and mountains afar. Two spacious decks to enjoy the natural setting. Main level has an artistically designed room with a spoke pattern beam ceiling, custom lighting, handcrafted shelving and a full bathroom. Lower level you will find a large spa primary bedroom suite w/ private patio, attached office/ reading room with access to the lower deck. Bathroom has double vanities, a soaking tub and radiant heat floors. Two additional bedrooms, a full bath and a laundry room are also on the lower level. Perfect for the outdoor enthusiast w/ hiking trails just a few feet from the front door.

774 Lisa Lane, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

$229,900
2 Beds 1 Baths 220204025 MLS
BEAUTIFUL LIGHT AND BRIGHT END UNIT with views of the golf course. Don't miss this opportunity! This 2-bedroom, 1-bath condo is located in the Oak Knolls neighborhood of Ashland. The kitchen is bright with plenty of cabinet space, a garden window and a pass-through to the dining room. The living room and primary bedroom open up onto a spacious, covered private outdoor patio. This unit boasts upgraded flooring with newer kitchen and laundry appliances. The bathroom features a large step-in shower and a bidet. This unit has a lot of storage space with 3 hall closets, a storage closet on the balcony and in the covered parking area, as well as large bedroom closets. You can enjoy the tranquil views of the community garden & backyard, and the beautiful Ashland hills from your living room or primary bedroom. The unit has updated plumbing, fresh paint inside & out and a newly repaved parking lot with carport! One Seller has active Real Estate License in the State of Oregon

854 Twin Pines Circle 7 Unit 7, Ashland

Listing courtesy of John L Scott Real Estate Grants Pass.

$1,100,000
220203024 MLS
Great development opportunity at the first major I5 intersection as one arrives from California to Ashland, Oregon. This high-traffic corridor property is perfectly positioned for maximum exposure to tens of thousands of vehicles daily. Potential uses include hotel/lodging, retail, restaurant, or mixed-use development—subject to local zoning approvals. An annexation for the development of a hotel is supported by Economic Data provided in Ashland's Comprehensive Plan and within the economic data provided since last Ashland Comprehensive Plan update. Required for annexation is a zone change from RR-5 to C1. Data and information from City of Ashland should align & justify the development request and address the shortage of adequate retail/commercial in the City. Perfect site for hotel with restaurant and conference facilities or an array of other commercial facilities.

OR-66, Ashland

Listing courtesy of Millen Property Group.

$646,000
3 Beds 2 Baths 220197028 MLS
Fall in love with this home of luminous spaces and serene views in a beautiful Ashland neighborhood perched above it all, with fresh air and plenty of quiet • Huge, main, open-layout room with dining area and cabinetry • Sunroom for casual dining & games • Irrigation system • Wood-burning fireplace • Full city services This 2332sf home mirrors the tranquility of its wooded surroundings--its vistas across the Rogue Valley will leave you and your guests beauty-struck and smiling. Sunlight floods the interior; Acacia wood floors add luxe and warmth. The MBR suite is spacious with scenic views. Two BDRMS face west: 1 carpeted, 1 office w/ skylight. The 2+car garage with storage. An expansive backyard deck connects the living space to the mountainside above, with direct access to Siskiyou Mtn Park trails and protected-from-development, watershed land. The house sits uphill from Siskiyou Blvd., between SOU and The Plaza, minutes from everything, and only 30 minutes to Mt. Ashland skiing.

932 Morton Street, Ashland

Listing courtesy of eXp Realty, LLC.

$459,000
220196344 MLS
Exclusively presented for sale - 30 Knoll Crest Drive, a rare public offering of flexible development land in Ashland of size (the ''Site''). Spanning 3.90-acres with additional land available to the North, the Site provides the opportunity for an entrepreneurial developer to create their vision on a stunning parcel of land. While currently zoned C-1, the Site lends itself to a mixed-use or residential-focused use (buyer responsible to confirm uses with City). Directly adjacent to one of the top hotels in Southern Oregon, the Site has a commanding presence at the 'Main and Main' intersection of this pocket of Ashland. The slope of the property allows for unimpeded views towards the Cascade and Siskiyou mountains. Visibility and access is exceptional, with a combined 11k+ VPD and easy paved access from either Hwy 66 or East Main. Utilities are relatively close (on East Main), but not yet connected. An exceptional Site - contact brokers! Buyer responsible for all due diligence.

30 Knoll Crest Drive, Ashland

Listing courtesy of Merit Commercial RE, LLC.

$1,050,000
220191240 MLS
Hard to find Commercial investment property in Ashland right across from SOU college! Located on the main road through town Siskiyou Blvd. This great business opportunity consists of 5 updated units. These units are updated and clean and would be great for many types of business. Units 1-2 1483 sqft have been made into 1 business rents for $2,188. As you enter it has a great inviting reception area, private rooms and is light and bright and has great flow. Unit 3 just went through a major remodel and has a great reception area and private rooms and is very inviting and rents for $1,620. Unit 4 1080 Sqft offers 5 private offices with a reception area and break counter area and rents for $1,626. Unit 5 is a quaint quiet spot with approx 700 sqft, would make a good rental or for your business and is vacant. A large parking lot allows for ample parking for all units.

993 Siskiyou Boulevard, Ashland

Listing courtesy of eXp Realty, LLC.

$550,000
220171722 MLS
Introducing 580 Clover Lane, a leased commercial investment anchored by a fully operational Tesla, Inc. Supercharger Station adjacent to the high-visibility I-5 corridor of Ashland. This 0.57-acre E-1 zoned parcel features 24 dedicated Tesla charging stalls operating 24/7 and generates consistent lease income from a corporate tenant. The property offers stable cash flow with minimal landlord responsibilities. Strategically positioned near the I-5 South Ashland interchange, the site benefits from strong regional and interstate traffic and proximity to established retail and hospitality amenities. In addition to the in-place income, the property offers compelling future upside. The sale includes architectural renderings for a proposed multi-level convenience store concept designed to capitalize on built-in charging traffic. A rare opportunity to acquire essential EV infrastructure with long-term positioning in a growing transportation corridor.

580 Clover Lane, Ashland

Listing courtesy of eXp Realty, LLC.

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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: