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852 Oak Street, Ashland
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 220217927 MLS
Platinum Earth Advantage home just minutes from downtown, offering 2,750 sq ft of thoughtfully designed 4BR, 3BA + office living space with stunning views of Grizzly Peak and the Cascades. This light-filled residence features 12' ceilings, expansive windows, quartz surfaces, designer lighting, and blonde wide-plank hardwood floors. The main level features two ensuite bedrooms, highlighted by a luxurious primary suite with radiant heated floors, dual shower system, and two walk-in closets. The chef's kitchen boasts an 11-ft island, double ovens, gas cooktop, beverage fridge, and walk-in pantry. Enjoy seamless indoor-outdoor living with an 8' slider to a spacious view deck. Lower level offers 2 bedrooms, office, second laundry, and potential for separate living. Professionally landscaped, private setting with detached 2-car garage, EV charging, and energy-efficient 2-zone HVAC system. Home designed by Vadim Agakhanov.

852 Oak Street, Ashland

Listing courtesy of Millen Property Group.

1068 E Main Street, Ashland
$1,250,000
5 Beds ⋅ 3 Baths ⋅ 220228921 MLS
Own a piece of Ashland's history with this incredible historical home, cherished by the same family for 100 years. Built in 1900, this 3,092 sq.ft. home offers 5 bedrooms and 3 full bathrooms and has been beautifully renovated for modern living while preserving its historic elegance. Original details include beautiful woodwork throughout, formal living and dining rooms, inglenook seating, wood flooring, original entry stairwell, and an original fireplace updated with a gas insert. The updated kitchen features custom cabinetry, granite countertops, a large island, and skylights. Updated bathrooms retain their vintage charm with claw-foot soaking tubs and gorgeous custom shower tile-work. The fully fenced property features gated entry, mature landscaping, and a large 2-car garage. Ideally located in the heart of Ashland, just minutes from downtown shopping, dining, entertainment, and nearby parks, making it easy to enjoy everything Ashland has to offer.

1068 E Main Street, Ashland

Listing courtesy of RE/MAX Platinum.

1969 Colestin Road, Ashland
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 220222210 MLS
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

Listing courtesy of Cascade Hasson Sotheby's International Realty.

451 N Main Street, Ashland
$1,249,000
8 Beds ⋅ 9 Baths ⋅ 220212846 MLS
Just blocks from downtown, this historic gem blends charm and flexibility. Original fir floors, built-ins, high ceilings, and abundant natural light pair with modern updates. Enjoy the welcoming lawn, pollinator garden, and large covered front porch. The main level offers spacious living and dining areas, kitchen, half bath, and generous entry spaces. A 1-bedroom apartment with interior and private exterior access--includes a kitchen, laundry and full bathroom--a separate additional en-suite bedroom with exterior entry adds versatility. Upstairs are four lovely en-suite bedrooms, one with a balcony, all with updated Renewal by Andersen windows and balcony door. A detached 704 sq ft, 2 bedroom, 1.5 bath, single level cottage with its own address and electric meter provides added flexibility or income potential. With six paved off-street parking spaces, sheds, on-street parking, and alley access, this property offers exceptional possibilities for multi-generational living or investors.

451 N Main Street, Ashland

Listing courtesy of Full Circle Real Estate.

545 Ashland Creek Drive, Ashland
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 220209743 MLS
Private tranquility in the treetops 4 min. to downtown Ashland. Views of Lithia Park w/soothing sounds of Ashland Creek flowing. Style meets sophistication on this beautiful architecturally designed home w/over ½ acre. $400K in new updates in the last 2 years. Private gated courtyard entry. Hardwood floors throughout, tile bathrooms floors, over 100 windows to bring in abundant light & cement balconies w/copper railings w/unobstructed views. Many trails close by. New massive artisan river rock wood burning fireplace in great rm. Chef's kitchen w/built in refrigerator, 6 burner gas cook top, dbl ovens, wine refrigerator, granite counters w/lg island. Formal dining & breakfast rm. 3 bdrms + lg office/meditation rm; 2 bdrm en-suites; Primary w/2 walk in closets, quartz counters, glass sinks, steam shower, air jetted tub, water closet & private balcony. 4 car garage, 2nd courtyard patio off entry. Home allows for an abundance of natural light w/vaulted ceilings & skylights.

545 Ashland Creek Drive, Ashland

Listing courtesy of John L. Scott Medford.

1650 Neil Creek Road, Ashland
$1,175,000
5 Beds ⋅ 4 Baths ⋅ 220229364 MLS
OWNER CARRY AVAILABLE! GOURMET KITCHEN. EMIGRANT LAKE VIEWS. 22 ACRES OF PRIVACY. This updated 5-bedroom, 3.5-bath home offers 3,270 sq ft on 22.05 acres. The gourmet kitchen features granite countertops and a stunning oversized island with 360-degree access for cooking and entertaining. Guest quarters and two separate laundry rooms provide flexibility. Updates include all-new doors and windows, a new roof, and new stucco with an imperfect smooth finish and upgraded cloth underneath designed to help reduce temperatures. A large garage with generous shop space accommodates vehicles, tools, and hobbies. The engineered greenhouse includes a concrete perimeter and separate power meter, with potential for shop conversion, subject to buyer due diligence. Level areas offer possibilities for future projects; buyers to verify permitted uses and development options. Enjoy beautiful lake views, exceptional privacy, and versatile spaces--with owner financing available to bring your vision to life!

1650 Neil Creek Road, Ashland

Listing courtesy of eXp Realty, LLC.

4567 Old Highway 99 S, Ashland
$1,175,000
5 Beds ⋅ 3 Baths ⋅ 220224554 MLS
One of a kind Southern Oregon retreat just 15 minutes from downtown Ashland, offering privacy, exceptional craftsmanship, sweeping views & proven income in a peaceful park like setting. A true money maker, the fully permitted first floor 2 bedroom/ 1 bath ADU currently operates as a successful Airbnb, generating approximately $25,000 a year in net income, per seller. The custom one owner main home features soaring ceilings, walls of windows framing Emigrant Lake and Grizzly Peak, a dramatic curved staircase, custom pine log accents, hardwood floors, granite and travertine finishes, floor to ceiling fireplace, kitchen with breakfast nook, third floor bonus wing & over 1,900 sq. ft. of wraparound cedar decking. Also includes workshop, playhouse and covered carport. The Airbnb has its own private driveway and entrance, ADA access, kitchenette with granite counters and a custom bath, ideal for rental income, guests or multigenerational living.

4567 Old Highway 99 S, Ashland

Listing courtesy of John L. Scott Medford.

1169 Iowa Street, Ashland
$1,150,000
220224634 MLS
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

Listing courtesy of Gateway Real Estate.

164 5th Street, Ashland
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 220229137 MLS
An amazing opportunity in an unbeatable location! Three separate living spaces surround gorgeous lush gardens in the heart of the Railroad District. The main home (164 5th) dates to the late 1800s and offers 3+ bedrooms, 2 baths and approximately 2,071 SF, with many improvements including a new foundation, electrical, plumbing, and HVAC ducting in '94. A detached 1 bed/1 bath apartment above the workshop provides vaulted ceilings, abundant natural light, and a private deck overlooking the gardens, plus bonus space below. A separate cottage-style home (162 5th), circa 1945, offers 2 bedrooms, 1 bath and its own private outdoor space. All three living spaces have separate meters for electric and gas. The main house and cottage also have separate water and sewer. Enjoy a greenhouse and outdoor storage bins for gardening. Lovingly cared for by the same owners for over 45 years, this special property shows true pride of ownership!

164 5th Street, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

400 Allison Street, Ashland
$1,100,000
2 Beds ⋅ 3 Baths ⋅ 220225582 MLS
Experience refined living just one block from downtown Ashland in this custom, open concept, built 2012 luxury home, designed for comfort and ease. An elevator to take you to all levels makes stair use unnecessary and 36 inch doorways provide seamless accessibility throughout. Rich oak and red oak floors and cabinetry pair beautifully with custom metalwork and soaring wood-paneled ceilings throughout the home. The chef's kitchen features a 6 burner Wolf cooktop, wall ovens, Sub Zero refrigerator, exposed edge granite countertops and custom pot racks. Spa inspired bathrooms include heated tile floors, dual vanities, tiled showers and abundant natural light, one with a soaking tub. The private flagstone courtyard with gas BBQ and pergola is perfect for relaxing and outdoor entertaining with lovely, low maintenance landscaping. The oversized, finished, two + car garage with sealed floors offers space for a workshop, gym and storage with an additional washer & dryer, sink and gas heater.

400 Allison Street, Ashland

Listing courtesy of Full Circle Real Estate.

OR-66, Ashland
$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.

993 Siskiyou Boulevard, Ashland
$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.

145 Normal Avenue, Ashland
$1,035,000
3 Beds ⋅ 3 Baths ⋅ 220228353 MLS
Tucked at the end of a cul-de-sac, this distinctive single-level home offers the rare feeling of country living right in Ashland. Set on a private, fenced and irrigated acre, it was thoughtfully built with Logix ICF insulated walls, owned solar, radiant-heated floors and energy-efficient windows. Inside, warm wood ceilings, a dramatic skylit cupola, walls of windows and a large fireplace give the home character, while the spacious kitchen features abundant cabinetry and a generous granite island. A large studio/game room adds wonderful flexibility. Outdoors, expansive Trex decking connects to a screened gazebo, pergola and covered patio overlooking mature landscaping, a pond and waterfall, raised garden beds and fruit trees, with mountain and valley views beyond. Oversized 2-car garage, workshop/storage and RV/boat parking. Near the bike path, schools and Hunter Park--peaceful, private and wonderfully connected to town.

145 Normal Avenue, Ashland

Listing courtesy of Millen Property Group.

120 E Main Street, Ashland
$1,000,000
220222324 MLS
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

Listing courtesy of John L Scott Ashland.

8612 OR-66, Ashland
$999,999
3 Beds ⋅ 4 Baths ⋅ 220217132 MLS
Stunning new contemporary home with mountain views on 20+ private acres! Interior highlights include natural hickory and maple hardwood floors and steps; porcelain tile in kitchen, bathrooms and great room, granite counter tops, washer and dryer in upstairs primary bedroom closet and connections for a second set up downstairs, windows wired for electric blinds or shades, beautiful stone fireplace all the way to the ceiling, all Dacor appliances. The exterior has stucco siding, and a metal roof on both the main house and detached garage. The oversized garage has enough space for 2 cars plus a shop area with ample lighting, EV charging outlet, and a heated full bathroom. The garage also has an attached 2 car carport. The covered patio boasts an outdoor fireplace and the upstairs balcony off of the primary bedroom is a perfect place to accommodate a hot tub and enjoy the views.

8612 OR-66, Ashland

Listing courtesy of John L. Scott Medford.

541 Fairview Street, Ashland
$996,000
5 Beds ⋅ 3 Baths ⋅ 220225227 MLS
Beautifully restored 1908 classic home located on a rare R2 zoned double lot just blocks from downtown Ashland's theatres, restaurants, galleries, and parks. MAIN RESIDENCE Featuring 3 bedrooms and 2 full baths, interior highlights include original fir floors, high ceilings, designer lighting, updated kitchen, pantry and abundant natural light throughout. Flexible layout supports guest space, office, or extended living arrangements. LOWER LEVEL Remodeled with separate entrance, kitchen, bedroom and full bathroom offering independent living space. Foundation of main home was updated in 1997 with central heat, air, electrical and plumbing systems. DETACHED COTTAGE Separate remodeled cottage with bedroom and bath ideal for additional flexible living needs, guest suite, or office. OUTDOOR FEATURES Mature landscaping with fenced yard, irrigation, water feature, dry sauna, spa, storage shed, and ample off street parking. ADDITIONAL HIGHLIGHTS R2 zoning ideal for income producing living.

541 Fairview Street, Ashland

Listing courtesy of Realty Net of Central Oregon.

480 Mount Ashland Ski Road, Ashland
$995,000
3 Beds ⋅ 3 Baths ⋅ 220227627 MLS
UNOBSTRUCTED VIEWS OF MT. SHASTA from the residence and not just somewhere on the property. Discover a rare mountain retreat, about 54± acres, where you can enjoy amazing privacy, peace, and stunning views of Mt. Shasta and Mt. McLoughlin without any obstructions. This unique lodge-style home boasts impressive massive post-and-beam construction and timeless design. The 3-bed, 2-bath home features an open great room w/floor-to-ceiling windows & breathtaking views. The expansive deck is perfect for sunsets, entertaining, & enjoying peaceful mountain life. A separate 1-bedroom guest cabin with its own deck and beautiful views adds extra privacy and flexibility. It's perfect as a main home, a luxurious second home, a family retreat, or a creative escape. You'll find it about 3 miles from Mt. Ashland Ski Area & 15 miles from the lively downtown Ashland. This is a truly unique chance to experience remarkable architecture, acreage, recreation, tranquility, and extraordinary natural beauty

480 Mount Ashland Ski Road, Ashland

Listing courtesy of Millen Property Group.

523 Strawberry Lane, Ashland
$995,000
5 Beds ⋅ 4 Baths ⋅ 220216782 MLS
Available for the first time, 2004-built custom home in Ashland's Strawberry Meadows. This 3,105 sq. ft. 5 bed/4 bath house sits on a private .46-acre lot bordering an oak-lined creek open space. Main level includes double-height entry with skylights, living room with wood-fire insert, dining room, well-planned kitchen with large pantry, and a primary suite with deck. Upper level offers four bedrooms, 3 with walk-in closets, and large family room with balcony overlooking the creek. Versatile layout accommodates expansive family life and home office space. Additional features include a 2-car garage, robust storage, an approx 200 sq ft finished bonus room not included in the square footage, and a generous patio off the dining/kitchen area with perennial gardens enclosed in a custom deer fence. Situated in a Firewise-certified neighborhood near Lithia Park with access to local hiking trails. This private and quiet property offers a rare opportunity for a special home in a coveted setting.

523 Strawberry Lane, Ashland

Listing courtesy of Gateway Real Estate.

381 Clinton Street, Ashland
$991,800
3 Beds ⋅ 3 Baths ⋅ 220210724 MLS
Stunning new construction in Ashland's Magnolia Meadows! This exceptional 3-bedroom home features a unique design and thoughtful use of space, making it a true neighborhood gem. Enjoy a pitched roof ready for solar panels, a fully fenced yard with drip irrigation, and beautiful landscaping with views of Grizzly Peak. Inside, benefit from top-of-the-line heating and cooling, on-demand hot water, and heated flooring in the primary bath. Elegant vaulted ceiling with skylights and clear story windows that envelope rooms with light. Gas fireplace serves as a focal point, complemented by 8-foot rift oak doors. Single-story living with no carpeting, deluxe primary suite, beautiful wide planked hardwood oak floors with the expansive living and dining area featuring custom built-ins, quartz countertops, and gourmet kitchen with a 36'' Bosch induction range, wine cooler, and more. Discover your dream home today!

381 Clinton Street, Ashland

Listing courtesy of Millen Property Group.

5831 Old Highway 99 S, Ashland
$950,000
3 Beds ⋅ 4 Baths ⋅ 220228020 MLS
Set on more than 37 private acres in the Siskiyou Mountains, this property offers space, privacy minutes from Ashland and the Rogue Valley. Mt. Ashland Ski Area, Emigrant Lake and the Pacific Crest Trail are nearby, putting Southern Oregon recreation close at hand. The main residence features soaring wood-clad ceilings, exposed beams, expansive windows and a stone fireplace. The open great room flows into a gourmet kitchen with cabinetry, full-size refrigerator and freezer, double ovens and island. A media room, geothermal heating and cooling, and hard-wired generator add comfort and peace of mind. A detached four-car garage provides spaces, while the auxiliary building offers an open area, kitchen, full bath and three-car garage--ideal for a studio, workshop, recreation or guest space. A loft studio, greenhouse, gardens, water storage, creek, rock outcroppings and wildlife complete this Southern Oregon retreat.

5831 Old Highway 99 S, Ashland

Listing courtesy of Windermere Van Vleet & Assoc..

501 Carter Lane, Ashland
$950,000
3 Beds ⋅ 2 Baths ⋅ 220226122 MLS
Welcome to 501 Carter Lane, a fully flat, usable property offering the ultimate blend of agricultural potential and incredible income generation! This upgraded 2,680 sqft. house is surrounded by amazing mountain views and features an 800 sq. ft. barn home, cottage, cabin, and a tiny home. The estate boasts tons of Airbnb rental income opportunity, with a 9-year 5-star Superhost history generating up to $100k+ annually. Built for growth, this farm features OMMP/ODA licensed gardens, greenhouses, and fertile soil. You'll find amazing, crystal-clear water with an endless well, irrigation ponds, and a 1-million-gallon TID water allocation. With upgraded electrical throughout and tons of equipment for farming included, it's a turnkey operation ready for your crops. Whether you want to farm, host guests, or move the whole family into this unique dream property, your endless possibilities await!

501 Carter Lane, Ashland

Listing courtesy of Real Broker.

2260 Old Highway 99 S, Ashland
$900,000
4 Beds ⋅ 3 Baths ⋅ 220227282 MLS
Welcome to PrayerFarm, a unique oasis for multi-generational living, community, homesteading, and events, all close to town. The light-filled primary home features sustainably harvested wood floors, a high-efficiency woodstove, a masonry Tulikivi, and ample indoor/outdoor entertaining spaces. A self-contained guest cabin provides overflow living. The massive 1,700+ SF ''barn'' is an absolute powerhouse, packed with an artist studio, guest suite with composting toilet, a scenic retreat loft, and a large office. Outdoor features include a cobb fireplace kitchen, ceremonial Tipi with an earthen floor, and a soothing Koi pond. The land is fully set up for self-sufficiency with a natural spring, abundant water storage, a fenced garden, mature fruit orchards, and an animal pen/coop. Modern convenience meets rural paradise with hardwired high-speed Ethernet throughout. Lovingly maintained for decades, this rare, special sanctuary is ready for its next chapter.

2260 Old Highway 99 S, Ashland

Listing courtesy of John L Scott Ashland.

1395 Woodland Drive, Ashland
$899,000
4 Beds ⋅ 3 Baths ⋅ 220229360 MLS
There's something special about a home that gives you room to live a little bigger. Your mornings can start with coffee on the large porch with unobstructed views of Grizzly Peak, while evenings offer the same backdrop from the large sitting room on the main level. Built in 1932 and offering 3,127 SF on a .30-acre lot, this is a home with history, personality, and plenty of room for what comes next. The main house has 3 bedrooms and 1.5 baths, while a permitted 1/1 ADU on the lower level creates a separate space for guests, family, or rental income. Beyond the house, the oversized heated two-story garage and shop is a major part of what makes this property unique. There's room for serious projects, hobbies, gear, storage, and vehicles, plus dedicated off-street RV parking. Inside, the home hasn't been updated to look like every other house on the market--and that's part of the opportunity.

1395 Woodland Drive, Ashland

Listing courtesy of John L Scott Ashland.

312 Sky Ridge Road, Ashland
$899,000
220221479 MLS
312 Sky Ridge Road offers 164 acres in the hills above Ashland, combining privacy, natural beauty, and usable land in a premier Southern Oregon setting. Zoned EFU, the property features a blend of moderately sloping terrain, open ground, and native landscape ideal for recreation, investment, or an exceptional estate setting. Approximately 2,220 feet of Cove Creek frontage adds scenic beauty and recreational appeal. A strong 48 GPM well, per 2018 well log, provides an excellent water source for future improvements. A fully paved drive leads to the property, with plans underway for a custom luxury entrance designed to complement the scale and quality of the setting. Elevations ranging from approximately 2,120 to 2,520 feet capture panoramic views in nearly every direction, creating a remarkable sense of space and connection to the surrounding mountains and valleys. Conveniently located near Medford, outdoor recreation, public lands, and Southern Oregon amenities.

312 Sky Ridge Road, Ashland

Listing courtesy of John L. Scott Medford.

3729 Old Highway 99 S, Ashland
$889,000
3 Beds ⋅ 4 Baths ⋅ 220224770 MLS
Enjoy spectacular views of Emigrant Lake & the surrounding mountains from this exceptional 3,713 sf custom 3 bd 3.5 ba home on over 30 acres, just 10 min from Ashland and a short drive to Mt. Ashland. From the moment you enter through the stunning mahogany door from your wrap around deck, you are welcomed into a great room with vaulted ceilings, a floor-to-ceiling rock fireplace, & windows that fill the home with natural light. Living space blends seamlessly into your gorgeous chef's kitchen & formal dining. An office w/ custom built-ins, bonus family room, & a guest half bath round out the main living space alongside an impressive primary suite, which features a private balcony, fireplace, & newly remodeled luxurious bathroom. Downstairs, you will find a guest ensuite, another guest bedroom, full bathroom, & laundry room. A 3-car garage provides plenty of space for cars & toys. Seller has done extensive fire mitigation work & paved the driveway, making this property insurable.

3729 Old Highway 99 S, Ashland

Listing courtesy of John L. Scott Medford.

5597 Highway 66, Ashland
$875,000
3 Beds ⋅ 3 Baths ⋅ 220225745 MLS
Tremendous 360 view on 5.75 flat white fenced acres & walking distance to Emigrant Lake. You have 3 acres of water rights on open EFU land, a 36'x36' barn with loft, a 14' RV bay door, workshop & attached office. Behind the barn is a single horse stall. To the side is a gazebo to enjoy those wonderful summer outside nights. This home is greeted by a paved & gated 800' driveway leading to a drive-through that takes you to the front entrance. Brand new wrap around porch greets you so you can sit in awe at the beauty of your surroundings or sit under your backyard gazebo and say, ''Do I really live here''? Perched on a small knoll, this 2,934 sq ft 4/3 home, has 2 bonus rooms, with open floor plan, large entertaining living room with woodstove insert fireplace & kitchen with abundant cabinets & island. Ten-foot ceilings provide ample sunlight for all occasions. The upstairs primary suite has a fireplace, en-suite bathroom with soaking tub & walk-in closet. Country comfort at its best.

5597 Highway 66, Ashland

Listing courtesy of John L. Scott Ashland.

901 Hillview Drive, Ashland
$874,000
3 Beds ⋅ 2 Baths ⋅ 220228466 MLS
Under construction for mid-December 2026 completion, this architecturally inspired midcentury home sits off-street on a private flag lot in an established neighborhood with mature trees. Vertical-grain cedar and stucco meet clean lines and covered porches. This 3-bed, 2-bath home is light and bright with clerestory windows, 8 ft doors, and vaulted ceilings. The kitchen's large island with eating bar opens to the great room, where a fireplace with a built-in bench-and-mantel sits by a wall of windows. The primary suite offers a roll-in shower, double vanity, and walk-in closet. A rare pass-through garage links the driveway and rear alley; drive straight through in either direction. No HOA. Built by Suncrest Homes, an Ashland builder with 35+ years of experience, this Earth Advantage home is energy-efficient and exceeds code. Ask about a promo 5.125% rate with the builder's lender. Listing broker is related to the owners of Suncrest Homes, one of whom is a licensed OR real estate broker.

901 Hillview Drive, Ashland

Listing courtesy of Gateway Real Estate.

128 S Mountain Avenue, Ashland
$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.

219 N Mountain Avenue, Ashland
$850,000
220226802 MLS
Calling all investors and developers - rare 1.5 acre opportunity in the heart of Ashland. This expansive parcel presents exceptional potential for subdivision and redevelopment, with possibilities similar to the nearby Clear Creek Subdivision. Ideally situated in a highly desirable location, this property offers convenient access to local amenities, schools, parks and downtown Ashland. The site is well situated for those looking to capitalize on Ashland's strong housing demand and limited land availability. Buyers are advised to perform their own due diligence with the City of Ashland regarding zoning, land use,utility availability and development requirements to fully realize the property's potential. Existing structures are considered uninhabitable and are expected to be removed following approval of a redevelopment plan, providing a blank slate for your vision. Land Use Report available for interested parties.

219 N Mountain Avenue, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

774 Lisa Lane, Ashland
$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..

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