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1750 Crestview Drive, Ashland
$735,000
3 Beds ⋅ 3 Baths ⋅ 220228500 MLS
Impeccable views and quality updated home is ready to go! Step outside directly onto hiking trails and return to this tranquil turn-key home on the end of a dead end street! Ample parking and covered space for storage of all ski gear and all your toys, make this home a year round gem to come home to after a long day of adventure! Only 30 mins from Mt Ashland from the front door! Fully updated bathrooms, kitchen and backyard make this home completely turn-key! The expansive primary suite features a sauna, walk-in closet and private wrap-around deck. Impeccable views with an open floorplan provide ample opportunities for hosting. This rare gem of views, storage and quality upgrades is one you won't want to miss!

1750 Crestview Drive, Ashland

Listing courtesy of John L. Scott Medford.

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.

264 Alta Avenue, Ashland
$625,000
4 Beds ⋅ 2 Baths ⋅ 220228422 MLS
Perched above downtown Ashland on a quiet street, this spacious 4-bedroom, 2-bath home offers privacy, proximity to town, and commands beautiful valley and mountain views. The open, light-filled floor plan centers around a vaulted great room and offers 2,176 square feet of flexible living space, including additional office and family rooms easily convertible to sleeping space on both levels. Step onto the expansive deck to dine outdoors, entertain, or simply enjoy the ever-changing scenery. A sauna provides a relaxing retreat, while ample storage and an attached garage add everyday convenience. Set on nearly a quarter-acre with mature fruit trees and room to garden, the property is just blocks from Lithia Park, the Ashland Plaza, dining, shopping, and the Oregon Shakespeare Festival. This is an exceptional opportunity to enjoy space, scenery, and an enviable location close to the heart of Ashland.

264 Alta Avenue, Ashland

Listing courtesy of Millen Property Group.

63 Nutley Street, Ashland
$599,000
2 Beds ⋅ 1 Baths ⋅ 220228381 MLS
JUST THREE DOORS UP FROM LITHIA PARK, the historic Hamaker-Taylor House blends timeless Ashland charm with modern luxury! Designed by notable architect Carlos Delgado and originally built in 1889, this one-of-a-kind cottage welcomes you with an expansive covered front porch and beautifully landscaped and hardscaped front and back yards, perfect for outdoor entertaining. Inside, enjoy a brand-new luxury kitchen with sunroom/breakfast nook, an updated bathroom, two bright bedrooms, and beautiful Pergo flooring throughout. Major improvements include new windows, HVAC, plumbing, electrical updates, and a new roof (2026). The full basement offers a versatile art studio with lighting, hot and cold running water, and raised storage areas. Enjoy the sounds of the bandshell from your front porch, with the OSF, Ashland Plaza, and Lithia Park just moments away. A rare opportunity to own a piece of Ashland history with today's comforts!

63 Nutley Street, Ashland

Listing courtesy of Windermere Van Vleet & Assoc..

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.

5010 Old Highway 99 S, Ashland
$399,000
2 Beds ⋅ 2 Baths ⋅ 220228254 MLS
Peaceful country living opportunity on 6.65 acres nestled amongst the madrones, not far from downtown Ashland! The custom primary residence offers 2 beds/2 baths with a stonework entryway, pine paneling and cabinetry in the kitchen, a cozy wood stove, large windows, a metal roof, and an attached garage. A versatile bonus room adapts to a creative workshop, office, or extra bedroom. Outside, a spacious deck and flat yard lead to an impressive shop built from steel shipping containers, offering a large open workspace with a professional-grade engine hoist, ample storage, and hydraulic hangar-style doors. Down the hill, a quaint cabin in the woods offers multigenerational living, income potential, or home office space, with a full kitchen, bath, and sleeping loft. Outdoor lovers will appreciate the unbeatable access to Mt. Ashland and the Pacific Crest Trail.

5010 Old Highway 99 S, Ashland

Listing courtesy of John L Scott Ashland.

7696 Hyatt Prairie, Ashland
$675,000
3 Beds ⋅ 3 Baths ⋅ 220228159 MLS
HYATT PINES RETREAT! Escape to this beautiful year-round mountain sanctuary on 7.76 ac. Tranquil setting backs to BLM land. Mostly level, nicely treed & surrounded by exceptional homes & towering pines in the 18-parcel community. Across from Hyatt Lake & near Howard Prairie Lake, outdoor adventure is at your doorstep--hiking, swimming, boating, camping, fishing, skiing & more! The home features a striking metal roof, fiber-cement siding, & wood casement windows. Cozy living room w/pellet stove. Main-level suite offers deck access, walk-in closet, ensuite bath with walk-in shower. 2nd main-level bedroom across from guest bathroom. Upstairs includes 3rd bedroom, loft, full bath & large bonus room (~23'x16') not included in 1,912sf. Numerous updates include roof, siding, windows, kitchen, flooring, baths, doors, furnace, water heater. Outbuildings: 2 large sheds, well house, garden shed. HOA $500/yr for road maintenance/winterization. Rare blend of privacy, recreation & mountain living!

7696 Hyatt Prairie, Ashland

Listing courtesy of John L. Scott Medford.

1058 Linda Avenue, Ashland
$599,000
5 Beds ⋅ 3 Baths ⋅ 220228065 MLS
Welcome home to this spacious 5 bedroom, 3 bath multigenerational home offering approximately 3,100 square feet of comfortable living space on a roomy .23-acre lot. Thoughtfully designed with two living rooms, there's plenty of room for gathering, relaxing, or creating separate spaces for extended family. A 2-car garage provides convenient parking and storage, while the covered back deck provides space to enjoy the tranquil backyard complete with a charming fish pond; perfect for enjoying your morning coffee or unwinding at the end of the day. Located in a quiet neighborhood just minutes from everything Ashland has to offer, you're less than 10 minutes from downtown Ashland, the Oregon Shakespeare Festival, and Emigrant Lake. Come experience the space, flexibility, and peaceful setting this special home has to offer!

1058 Linda Avenue, Ashland

Listing courtesy of John L Scott Real Estate Grants Pass.

Neil Creek Road 800 Unit 800, Ashland
$99,000
220227198 MLS
Rare opportunity to own +/-12.16 acres in the Ashland area near Neil Creek Road with wooded hillside terrain, oak, madrone, pine, animal trails, and potential valley and Emigrant Lake views from portions of the property. The land has strong recreational appeal and a quiet, tucked-away feel once on site. Jackson County records show WR zoning, and County Planning has indicated a dwelling application may be possible through applicable land-use review; no dwelling approval is currently in place. No confirmed legal access, well, septic, or power service. Property is being marketed as-is, with all access, zoning, utilities, water, septic, dwelling potential, and intended use to be verified by buyer. A unique Ashland-area landholding for a buyer with vision, patience, and a willingness to complete their own due diligence.

Neil Creek Road 800 Unit 800, Ashland

Listing courtesy of Whitetail Properties Real Esta.

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..

119 Granite Street, Ashland
$800,000
2 Beds ⋅ 2 Baths ⋅ 220227845 MLS
Location, character, and potential come together in this one-of-a-kind property situated on a generous 0.22-acre lot just steps from iconic Lithia Park. From the moment you enter, you'll be greeted by an abundance of warmth and sunshine, with natural light flooding both the living room and primary bedroom. The home boasts a unique personality, blending a cozy, rustic cabin vibe, with a flexible bonus space ready for your imagination ideal for a creative art studio, office, yoga room, or guest area. In the heart of the home, the kitchen features durable Corian countertops and a charming built-in breakfast nook, perfect for morning coffee. Relax on the covered front porch overlooking a well-maintained front yard equipped with an automatic sprinkler system. Enjoy your own a private courtyard with a detached single-car garage for parking or extra storage. Whether you're seeking a serene sanctuary or a property with endless possibilities in an unbeatable location, this gem is a must-see!

119 Granite Street, Ashland

Listing courtesy of eXp Realty, LLC.

527 Sutton Place, Ashland
$745,000
3 Beds ⋅ 3 Baths ⋅ 220227832 MLS
Delightful and lovingly maintained 3-bedroom, 2.5-bath home nestled in a desirable neighborhood with minimal through traffic. This inviting property features a covered front porch entry, an open great room- dining area designed for comfortable living and entertaining, a convenient guest bath, and a bright, sunny kitchen with a breakfast nook, abundant natural light, and direct access to a covered outdoor living space. The main-level primary ensuite offers privacy and convenience with direct access to the backyard patio. Eco-friendly bamboo and cork flooring add warmth and character, while the spacious second-floor bonus room provides flexible space for a home office, media room, playroom, or guest retreat. Enjoy beautiful landscapes, mountain views, and a private fenced backyard with a covered patio overlooking a serene common area. Complete with an attached two-car garage and situated in a wonderful neighborhood, this home offers comfort, privacy, and easy living.

527 Sutton Place, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

4334 Clayton Road, Ashland
$99,000
220227665 MLS
This 5.46-acre wooded lot offers privacy, tranquility and sweeping views from high above the valley floor. Just 6.5 miles from Ashland's vibrant downtown, the neighborhood's large parcels and scattered rural homes create a sense of space, with neighbors nearby but not too close. Enjoy expansive valley and mountain views as you watch sunrises and sunsets, listen to the birds, and relish the quiet of this peaceful setting. The lot has received homesite approval twice in the past, although both approvals have expired. Buyers should conduct their own due diligence with Jackson County Planning regarding homesite and development possibilities, as well as easements and utilities. Access is via Timberlake Drive, with an undeveloped access easement from Clayton Road. Enjoy acreage, views and solitude within easy reach of Ashland.

4334 Clayton Road, Ashland

Listing courtesy of Nestwell Real Estate.

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.

2025 Green Meadows Way, Ashland
$595,000
3 Beds ⋅ 2 Baths ⋅ 220227602 MLS
What an amazing home in this highly desirable neighborhood. You have the best curbside look on the block with low maintained manicured front and backyard. Close to the Oredson Todd Woods and surrounding Ashland trails. Featured with abundant living space for all to enjoy. A large living room with dining area, wood stove and open space that leads you to an additional enclosed sunroom to enjoy the abundant sunlight, crafts and comfortable summer evenings. Also, there is a great living room for additional entertainment. Hard wood, laminate & vinyl flooring. Both bathrooms have been recently remodeled. One bedroom has been used as an office with a long countertop working space. The primary bedroom also leads you out to a wonderful large deck. Rear deck is designed for BBQ's and entertainment. Come and enjoy this special backyard with views of the Cascades and Grizzley Peak. Just 3 miles from the Shakespeare Festival. TID water comes with this property.

2025 Green Meadows Way, Ashland

Listing courtesy of John L. Scott Ashland.

2590 Siskiyou Highway, Ashland
$635,000
4 Beds ⋅ 2 Baths ⋅ 220227582 MLS
This beautiful recently renovated ranch is home located just 15 minutes from Ashland. Step inside to hickory hardwood floors, an open floor plan and unobstructed million-dollar panoramic views of Emigrant Lake, Pompadour Bluff, Grizzly Peak and the Siskiyou Mountains. Several french doors offer an immersive indoor-outdoor living concept with an ample patio perfect for dining and BBQing. The fourth extra large bedroom is adjacent to a solarium that would make a fantastic hot tub space. This 7+ acre mini-ranch is fully fenced and gated, with an interior dog fence line that is approximately two acres. Irrigated with water rights from a spring source, the ample lawn space is a dream come true. This versatile property features offer multiple workshops, a greenhouse, a paved basketball court, two carports, plenty of parking for RVs, boats, trailers and so much more. This one wont last long!

2590 Siskiyou Highway, Ashland

Listing courtesy of Cascade Hasson Sotheby's International Realty.

2140 Birchwood Lane, Ashland
$410,000
2 Beds ⋅ 2 Baths ⋅ 220227463 MLS
This inviting, move-in-ready home is filled with natural light and offers a functional, comfortable layout with fresh interior paint and upgraded blinds throughout. The living room features a cozy gas fireplace and flows seamlessly into the kitchen and dining area. Brand-new, high-end stainless appliances, a stylish backsplash behind the range, and a dedicated eating area complete the kitchen. The spacious primary suite offers a generous closet and ensuite bath with a walk-in shower. A second bedroom, additional full bathroom with a tub/shower combination, and conveniently located hall laundry closet add to the thoughtful layout. Step outside to a fully fenced, low-maintenance backyard featuring a concrete patio, southwest-facing exposure, and mature trees that provide beautiful filtered light and welcome shade. A beautifully landscaped front yard with a drip irrigation system and an attached two-car garage complete this truly charming home!

2140 Birchwood Lane, Ashland

Listing courtesy of John L Scott Ashland.

2234 Dollarhide Way, Ashland
$439,920
2 Beds ⋅ 3 Baths ⋅ 220227296 MLS
Move-in ready and beautifully updated! The main level features new vinyl flooring (2025), LED lighting, and an electric fireplace for added ambiance. The kitchen offers an eating bar, dining area, and new dishwasher (2025). A half bath with pedestal sink and attached one-car garage complete the main level. Upstairs are 2 bedrooms, 2 full baths, new carpet (2026), a spacious landing ideal for an office or flex space, and a view deck with retractable awning. The primary suite includes a walk-in closet and ensuite bath with shower. Laundry closet includes washer & dryer. Major updates include new roof (2025), heating & A/C (2024), water heater (2024), exterior paint (2026), and new smoke/CO detectors (2026). Enjoy a private fenced backyard with patio, garden beds, views, and refreshed low-maintenance landscaping. Extensive updates and a functional floor plan make this home ready to enjoy!

2234 Dollarhide Way, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

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.

10001 Dead Indian Memorial Road, Ashland
$285,000
220227276 MLS
Escape to your own private forest retreat on 20 beautiful acres at 10001 Dead Indian Memorial Road in Ashland, Oregon. Surrounded by natural beauty and offering stunning, expansive views, views of Mt Ashland, this property is ready for your vision. Quonset hut on heavy duty cement slab. Older cabin and storage out buildings. Recent improvements include a new power pole, a new driveway and new well, plus two RV spots, making it an excellent option for a recreational getaway, base camp, or future homesite. The property also offers timber value, adding to its versatility and investment potential. Enjoy the peace, privacy, and wide-open feel of your own Southern Oregon forest escape--all while being approximately 20 minutes from I-5 and 25 minutes to downtown Ashland.

10001 Dead Indian Memorial Road, Ashland

Listing courtesy of Gateway Real Estate.

583 Coffee Lane, Ashland
$379,900
2 Beds ⋅ 1 Baths ⋅ 220227252 MLS
Built in 2022 with an emphasis on efficiency, simplicity, and modern design, this Earth Advantage-certified cottage offers an easy, comfortable way to live. The bright, open interior features vaulted ceilings, abundant natural light, and contemporary finishes throughout. The kitchen pairs quartz countertops with stainless steel appliances and a convenient breakfast bar, creating a stylish and functional heart of the home. Outside, the fully fenced yard is an exceptional extension of the living space, with a private patio and room for gardening, dining, or simply enjoying the mountain views. As part of a shared solar community, the home is designed with energy efficiency and lower operating costs in mind. With its manageable size, low-maintenance design, outdoor space, and modern construction, this two-bedroom, one-bath home is a smart opportunity for anyone looking for a newer home without the upkeep of a larger property.

583 Coffee Lane, Ashland

Listing courtesy of Millen Property Group.

485 Orchard Street, Ashland
$589,000
5 Beds ⋅ 4 Baths ⋅ 220227203 MLS
Over 1/2 Acre lot near historic Ashland Plaza! This 5 bedroom 4 bath home offers 2,487 sqft of living space set in a highly sought after neighborhood just minutes from shopping, dining and entertainment such as the Oregon Shakespeare Festival. The spacious floor plan provides plenty of room for everyday living, hosting and creating dedicated spaces for work, hobbies or relaxation. Two fireplaces add warmth and character, while the multiple sliding doors allow natural light to flood the living areas. One bathroom features an ADA accessible shower with floor to ceiling tile and custom stone, delivering both style and functionality. Outside, the beautifully landscaped lot offers an ideal setting for gardening or entertaining while providing convenient parking for multiple RVs, campers, trailers or boats. Don't wait, your next chapter starts here!

485 Orchard Street, Ashland

Listing courtesy of RE/MAX Integrity.

3404 Siskiyou Boulevard, Ashland
$699,000
4 Beds ⋅ 3 Baths ⋅ 220227055 MLS
Beautiful Mountain Views on 5.4 Acres ! Enjoy stunning mountain views from the spacious front deck of this beautiful 2,989 sq. ft. home situated on 5.4 acres. The open--concept upper level features large, bright windows that fill the home with natural light, creating a warm and inviting living space . This home offers 4 bedrooms and 3 bathrooms, providing plenty of room for family, guests, or a home office. Additional features include TID irrigation, a newer roof, and a newer energy--efficient heat pump for year--round comfort. The lower level has 2 bedrooms with a full bath and side access door to enter. Whether you're relaxing on the deck, entertaining in the open living area, or enjoying the privacy of your acreage, this property offers the perfect blend of space, comfort, and scenic beauty.

3404 Siskiyou Boulevard, Ashland

Listing courtesy of RE/MAX Platinum.

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