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$799,000
1 Beds 2 Baths 220224982 MLS
It's all about the beautiful 13.39 contiguous acres with 12.6 acres of TID irrigation, panoramic views and just minutes to downtown Ashland. Family owned since 1964, the original home was built in 1915. There are 3 separate tax lots, one with the original home,8-stall horse barn and workshop (5.81 acres), one that has a non-expiring homesite (confirm with county) with fantastic panoramic views (4.53 acres) and the third with a large barn (3.05 acres) and separate access. All 3 may be sold separately (check with Jackson County Planning). Tax lot #700 has a small home, large shop, a 8-stall barn, tack room and small living quarters in the back. There is a 2-story barn on tax lot #300. The portion of the property growing grass and clover for hay produces approximately 400-600 bales and has wheel line irrigation. There are many other potentials for this EFU property.

1249 N Valley View Road, Ashland

$1,185,000
3 Beds 2 Baths 220224794 MLS
Lovely home on just over 5 acres located on a private drive in the Maitri community, just minutes to both downtown Talent and Ashland. You'll love this peaceful rural setting with stunning mountain and valley views. Single level living, meticulously maintained and tastefully renovated to give you the best of country living. Expansive windows capture the big skies of So. Oregon, colorful sunsets and twinkling lights of the valley. The spacious open floor plan and sophisticated, yet easy, design style make this home perfect for entertaining. Relax in the large primary bedroom en-suite complete with soaking tub, separate shower and large walk-in closet. Plenty of room for outside entertaining on the large paver patio and rear deck that overlooks the rolling hills, pastures and fenced raised bed gardens. Basement space below the home provides excellent storage and could be finished out for additional square footage.

651 Holton Road, Talent

$1,149,000
4 Beds 4 Baths 220224723 MLS
Perched in one of East Medford's most sought-after neighborhoods, this distinctive High Oaks estate captures breathtaking valley and mountain views from nearly every room, offering the rare opportunity to enjoy both spectacular sunrises and sunsets from the comfort of home. Set on .75 acres, the 3,963 square-foot residence features 4 bedrooms, 3.5 baths, a living room, family room, formal dining room, breakfast nook, and entertaining area with wet bar. Walls of windows and vaulted ceilings fill the home with natural light, while a unique glass sunroom connects to the pool, spa, and surrounding scenery. Main-level bedroom, split-bedroom design upstairs, walk-in pantry, poolside sauna, multiple decks, and 3-car garage add to the home's appeal. Plus a 48-panel solar system and newer HVAC. Located 5 minutes from Rogue Valley Country Club, RoxyAnn Winery, shopping, dining, and medical services.

229 Mariposa Terrace, Medford

$690,000
2 Beds 2 Baths 220224672 MLS
Amazing opportunity with 5 legal lots per City of Ashland and phenomenal views. Amy Gunter of Rogue Planning & Development Services has extensively researched and received letter from City of Ashland Legal Lot Determination stating 5 lots. TID water rights. In addition there is a cute, sweet 2 bedroom, 2 bath home with detached garage. Orignal wood floors in bedroom and livingroom and maybe under the carpet in the hall. Living room has fireplace with built in bookcases on either side and you will love the unbelievable mountain views through the picture window. Home has been rented for many years and sits ''as is''. Cute unique kitchen with dining nook. Call listing agent for details and property package. Buyer to do their own due diligence for their own plans for the property.

595 Monroe Street, Ashland

$1,200,000
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 a workshop, playhouse and covered carport. A former homesite offers additional potential. The Airbnb has its own private driveway and entrance, ADA access, kitchenette with granite counters and a luxury bath, ideal for rental income, guests or multigenerational living.

4567 Old Highway 99 S, Ashland

$799,000
3 Beds 2 Baths 220224388 MLS
High on a hill near Jacksonville is the 21.49 acre property with a custom built home of 2626 sq ft. Featuring 3 bedrooms and 2.5 baths with an open concept and soaring tongue and grove wood ceilings in great room and Primary suite and massive windows to take in the incredible panoramic view. This primary has an ensuite bath room with double vanity and walk in shower and walk in closet. There are two additional bedrooms that share a bath. The Trex decking runs the length of the great room and the primary with access from both and super for entertaining. There is also access to the 1/2 bath from the deck. The seller is motivated and this property needs some TLC. Attached in documents is an estimate for roof repair needed, not including the dry wall repair needed on the inside. Some of the photos have been virtually staged . All information is deemed accurate and the buyer should do own due diligence as to the uses and condition of this property.

465 Strawberry Hill Lane, Jacksonville

$2,000,000
5 Beds 5 Baths 220224293 MLS
Rare Mediterranean estate with panoramic views, masterfully built by Michael Pagnini. This 6,231 sq.ft. executive home offers 5 bedrooms, 4.5 baths on 1.22 private acres, plus a beautiful main-level office. A grand entry welcomes you to formal living and dining spaces, where floor-to-ceiling windows frame sweeping mountain, valley, and city-lights views. The chef's kitchen impresses with granite, a four-sided glass display cabinet, built-in fridge, and full-size freezer, anchored by a double-sided fireplace shared with the family room. The luxurious primary suite features a private gym, your own retreat for wellness and renewal. Step outside to a salt water infinity-edge pool with electric cover, sunken hot tub, and a gas fireplace beneath an elegant gazebo, ideal for entertaining. Complete with a home theater, 966-bottle wine cellar, and 4-car garage with abundant storage. Every detail reflects exceptional craftsmanship and timeless design. Prepare to fall in love.

1491 Montclair Terrace, Medford

$695,000
2 Beds 3 Baths 220223937 MLS
Beautifully Maintained Custom Ashland View Home! This property offers a blend of distinctive architecture and serene privacy with custom windows and natural beauty throughout. Step-down living room with gas fireplace, dining room has built-in shelving; house has engineered hardwood flooring and carpeted bedrooms; kitchen has newer 36'' gas range and built-in desk. Spacious ground-floor master bedroom, second upstairs bedroom, separate office that could be used as a guest bedroom, plus upstairs laundry room. View decks for indoor-outdoor living, mature landscaping and peaceful setting that includes patio, firepit, walking paths and fully fenced backyard. Quality upgrades include Karastan wool carpeting, newer roof, high-efficiency 2-stage HVAC, fresh interior paint, oversized garage with workshop/bonus area, central vac, 220v for EV charging and great storage throughout. Lovely hillside home on a quiet cul-de-sac just minutes from downtown with EZ access to Ashland's trail system.

590 Taylor Street, Ashland

$2,950,000
5 Beds 6 Baths 220223587 MLS
Stunning mansion located in Southern Oregon! This home was fully completed in 2015 with millions of dollars in infrastructure and high-end finishes. Recently finished high end pool was put in for you to enjoy as you take in the breathtaking 360-degree views of the Rogue Valley. This property comes with over 20 acres of land, partially usable with room for animals, fully paved + gated entrance gives you security and peace of mind. This home features over 1800 sqft of garage space (6 cars) and could fit more. This is truly an entertainer's home with plenty of room in the front yard for large gatherings, or in the backyard on the patio and in the pool - Or downstairs in your bar/wine cellar! With 5 bedrooms, and 5.5 bathrooms + office + entertainment rooms. Built with 13'' ICF walls maximizing efficiency. Also - a sauna, wine cellar, concrete safe room, bar and so much more. Too much for a short description - Please inquire for more information, come and tour it to see the rest!

15202 Richards Way, Eagle Point

$629,000
3 Beds 2 Baths 220223536 MLS
Welcome home to Jacksonville charm! Nestled among mature trees & abundant wildlife, this newer single-level home offers a peaceful retreat just minutes from downtown. The bright open floor plan has vaulted ceilings, transom windows, & a cozy fireplace that creates an inviting gathering space. The spacious kitchen is designed for everyday living & entertaining, featuring granite countertops, stainless steel appliances, pendant lighting, & classic white subway tile. The private primary suite includes a walk-in closet, dual vanities, & a beautifully tiled shower. A sliding door opens directly to the tranquil backyard, where a covered patio, paver seating area, & gas hookup for summer barbecues invite outdoor living year-round. A charming garden offers raised beds for flowers, herbs, or vegetables. Neighborhood amenities include a community center, open space, & direct access to the 255-acre Jacksonville Woodlands, with miles of scenic trails & natural beauty

250 Oak Knoll, Jacksonville

$699,000
3 Beds 3 Baths 220223512 MLS
Gorgeous home, priced to sell!!! Perched above the boulevard in an upscale neighborhood of high-end homes, this picturesque property offers the perfect blend of luxury and nature. Located just steps from the scenic hiking trails of Hald-Strawberry Park, less than 1 mile from Lithia Park, OSF, and the best restaurants and shops in Ashland. The main level welcomes you with beautiful views out of every window, solid oak hardwood floors, and a living room with a classic brick fireplace and French doors leading to a lovely deck. The fully renovated kitchen stuns with premium travertine tile flooring, stunning Brazilian quartzite counters, and stainless steel appliances. There's more to love upstairs- gorgeous views, a spacious primary suite, a light and bright guest room, and a flexible 3rd bedroom that easily doubles as a home office, featuring built-in shelving and a charming window seat. Solar. EV charging. Garage workshop space and so much more! Home appraised at 815k. Instant equity!

215 Piedmont Drive, Ashland

$850,000
3 Beds 2 Baths 220223497 MLS
Tucked in the hills of Ashland, this exquisite light filled brick home offers a rare blend of elegance, privacy, views and natural beauty. This 3 bedroom, 2 bath house features a large open floorplan, skylights, chef's kitchen with 6 burner gas range and island, expansive great room, double paned windows, dining room, primary suite with walk in closet and so much more. This thoughtfully designed home showcases quality craftsmanship, refined finishes and allows for seamless indoor-outdoor living. The yard features fire safe landscaping, custom organic gardens, dozens of varieties of flowers and trees, Japanese maples, dogwoods, abundant wildlife and a koi pond with waterfall. Enjoy the large multiple car garage and workshop, along with an additional downstairs bonus room with multigenerational living potential. Total square footage including the garage/workshop and finished bonus room is 3436! The home has been very well maintained, with both a newer roof and brand new HVAC system

1365 Ponderosa Drive, Ashland

$1,250,000
3 Beds 2 Baths 220223463 MLS
Set on 2.21 impeccably maintained acres with two gated entries, 2564 Old Military Rd offers privacy, polish, and close-in convenience in a truly stunning setting. This refined single-level estate captures sweeping views of Mt. McLoughlin, Roxy Ann, the valley, and surrounding mountains from landscaped grounds with mature trees, garden space, pasture, covered patios, and outdoor living areas. The move-in ready home has been extensively updated for a comfortable, elevated lifestyle with acacia wood floors, imported travertine tile, leathered granite counters, vaulted ceilings, rich wood details, and expansive windows that bring the views inside. A thoughtful split floor plan places two bedrooms and one bath on one side, with the luxury primary suite privately positioned on the other. Guest quarters above the shop add flexibility, while attached carports provide space for RVs, boats, trailers, or utility vehicles. An attached 2 car garage completes this peaceful, turn-key property.

2564 Old Military Road, Central Point

$14,000,000
220223436 MLS
Offered for sale for the first time ever, Belle Fiore Estate Winery is Oregon's most significant vineyard estate and event destination situated on 51+ acres, including 37+ irrigated acres and an established vineyard with 14 grape varieties. The estate encompasses more than 27,000 sqft and features multiple tasting rooms, a ceremonial barrel room, elegant ballroom, full-service restaurant, expansive terraces, and outdoor dining areas overlooking the vineyard and valley. The production facility is designed for commercial-scale operations with 8 barrel-storage bays, refrigerated wine storage, soaring ceilings, and extensive infrastructure. Hosting more than 50,000 visitors annually, Belle Fiore is a recognized destination for wine tourism, weddings, corporate retreats, and private events. This combined with significant growth potential make this a rare opportunity to own a premier winery. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

100 Belle Fiore Lane, Ashland

$12,000,000
7 Beds 19 Baths 220223437 MLS
Chateau at Belle Fiore is one of Oregon's most extraordinary estates. Spanning over 17,400 sqft across 4 levels, this French-inspired masterpiece offers 7 bedrooms, 19 bathrooms, and exceptional craftsmanship throughout. An elevator services all floors, including an 8,000 sqft lower level with a wine room, game room, gentleman's lounge, multiple wine bars, and expansive entertaining spaces. Premium finishes include custom cumaru flooring, granite surfaces, and intricate architectural detailing. Set on 17+ acres, including 12+ irrigated acres and a producing vineyard, the estate is ideal for private enjoyment, weddings, retreats, and special events. Exterior features include hand-chiseled golden granite, a hand-cut slate roof, custom copper gutters, dormers, and downspouts. A 2,500+ sqft carriage house, 4-car garage, prep kitchen, and grand gathering spaces complete this iconic estate. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

200 Belle Fiore Lane, Ashland

$26,000,000
220223435 MLS
Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is for sale for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,400+ sqft; it has four levels, 5 bedrooms, 19 bathrooms, a 4-stop elevator, vineyard, 2 bedroom 2500+ sqft carriage house, 4-car garage, resort style pool, hand-cut slate roof, custom copper detailing, and one of a kind craftsmanship throughout. ~ Separately, the Winery features a 32-acre vineyard with 14 distinguished grape varietals. The 27,000+ sqft Italian basilica-inspired facility includes tasting rooms, a ceremonial barrel room, ballroom, restaurant, outdoor dining areas, panoramic views of the Rogue Valley, and a commercial production facility with extensive refrigerated wine storage. Set on nearly 70 acres, this offering includes 49+ acres of water rights. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

100 Belle Fiore Lane, Ashland

$26,000,000
7 Beds 19 Baths 220223434 MLS
Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is for sale for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,400+ sqft; it has four levels, 5 bedrooms, 19 bathrooms, a 4-stop elevator, vineyard, 2 bedroom 2500+ sqft carriage house, 4-car garage, resort style pool, hand-cut slate roof, custom copper detailing, and one of a kind craftsmanship throughout. ~ Separately, the Winery features a 32-acre vineyard with 14 distinguished grape varietals. The 27,000+ sqft Italian basilica-inspired facility includes tasting rooms, a ceremonial barrel room, ballroom, restaurant, outdoor dining areas, panoramic views of the Rogue Valley, and a commercial production facility with extensive refrigerated wine storage. Set on nearly 70 acres, this offering includes 49+ acres of water rights. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

200 Belle Fiore Lane, Ashland

$824,999
4 Beds 3 Baths 220223402 MLS
Experience breathtaking mountain views from nearly every main living space in this beautifully designed 2021 Jacksonville home. Walls of windows fill the great rm w/natural light, seamlessly connecting to expansive view decks creating exceptional indoor-outdoor living. The gourmet kitchen features premium BlueStar gas range, lg island, leathered granite counters, stainless appliances, walk-in pantry & abundant workspace. Maple hardwood floors, designer lighting, Hunter Douglas window coverings & quality finishes enhance the home's appeal. 4 bed plan w/main-level primary suite offering private deck access w/serene valley views, walk-in closet, soaking tub & oversized tiled shower. Also on the main level are a dedicated office w/built-ins, half bath & laundry rm w/sink & storage. Downstairs offers 3 more bedrooms, full bath & spacious bonus rm, ideal for guests or multigenerational living. EV-ready garage. Perfect for those who travel- leave w/peace of mind & return to effortless living!

1300 Andrews Place, Jacksonville

$2,140,000
5 Beds 5 Baths 220223401 MLS
Rare 203-acre Ashland estate with sweeping south-facing views offers a resort setting tucked away at the end of a mountain road. Completed in 2015, the 7,468 sq ft Craftsman residence was designed for beauty and function. The main level showcases two primary suites, two additional oversized bedrooms, expansive living and family rooms, and a gourmet kitchen. One walnut staircase leads to a private loft while a second stairway leads to a spacious upper level bonus room. The partially finished daylight basement has exterior and patio access. The original 1,812 sq ft home is now an amazing fully finished flex space, ideal for guests, office, studio, or recreation. Surrounded on three sides by the Siskiyou Cascade National Monument for vast recreational opportunities. The property offers pasture, wooded terrain, and creek frontage. This rare legacy estate delivers self sufficiency, seclusion, and unparalleled outdoor access while remaining within reach of Ashland's renowned amenities.

22494 Jefferson Road, Ashland

$1,295,000
3 Beds 3 Baths 220221928 MLS
Stunning Modern Home with Unobstructed Panoramic Views. Designed as the builder's personal residence, this exceptional modern home was thoughtfully crafted to capture the beauty of Southern Oregon from nearly every room. Expansive windows frame breathtaking views of RoxyAnn, surrounding mountains, and twinkling city lights below. Offering over 3,000 SF of primarily single-level living, the home blends clean architectural lines with warm finishes including soaring ceilings, white oak flooring, oversized doors, and a stunning chef's kitchen at the center of the home. Outside, enjoy terraced landscaping, greenhouse, outdoor fireplace, and an expansive covered patio designed for year-round entertaining. Complete with parking for 5 vehicles, workshop space, generous storage, and a versatile lower-level flex room with full bath, this Bill Burfield Construction home perfectly balances luxury and functionality.

4310 Tamarack Drive, Medford

$989,000
5 Beds 4 Baths 220223317 MLS
Escape the summer heat at your own private Southern Oregon retreat! Nestled on peaceful acreage with the North Fork Little Butte Creek flowing through the property, this one-of-a-kind estate offers cool mountain air, unmatched privacy, and abundant wildlife. Enjoy hiking, fishing, horseback riding, hunting, ATV trails, and nearby public lands, all just 25 minutes from Eagle Point and 35 minutes from MFR. The extensively renovated main home features hundreds of thousands of dollars in upgrades, soaring vaulted ceilings, exposed beams, skylights, curved architectural details, and Andersen windows and sliding doors that showcase the surrounding landscape. A lower-level apartment and detached guest cottage offer flexible space for multigenerational living, guests, or income potential. Creek frontage, mature trees, gardens, an insulated studio, chicken coop, and more. See attached improvements list.

24041 Highway 140, Eagle Point

$779,000
4 Beds 4 Baths 220223301 MLS
Custom view home with charming detached guest cottage located just above downtown between Lithia Park and the Ashland Public Library. Main level great room with vaulted double-height ceiling, walls of windows, reclaimed clear-grain fir trim, solid-core doors, refinished oak floors, kitchen with composite dining bar, tile counters and backsplash, cabinets with solid wood interiors and custom pull-outs, dining room with glass door to view deck with gas BBQ hookup, bedroom with closet and full ensuite bath, and pantry with washer and dryer. Upper level primary with skylights, hanging closet, French doors to private balcony, and full ensuite bath with jetted tub. Versatile lower guest suite or family room with French doors to paver patio, full bathroom with oversized shower, storage cellar with stainless utility sink, and one-car garage. Detached cottage with permitted kitchen, living area, full bathroom, loft bedroom, and private gated entrance from Terrace Street. Inquire for details!

307 Hillcrest Street, Ashland

$585,000
2 Beds 2 Baths 220223164 MLS
A rare opportunity on beautiful Birdseye Creek Road. This cherished family property has been lovingly maintained for generations and is ready for its next chapter. Situated on 7.44 fully fenced acres, the property offers a wonderful blend of privacy, usability, and versatility. A security gate at the entrance provides added peace of mind and a welcoming sense of arrival. Highlights include: Approximately 1.7 irrigated acres Fully fenced property with gated entry. Large ventilated shop ideal for hobbies, equipment, or storage. Existing second homesite with septic and separate power meter already in place. Plenty of room for animals, gardening, or recreation Whether you're looking for space for extended family, a hobby farm, or simply a peaceful country setting, this property offers exceptional possibilities. Generations of care are evident throughout this unique property, offering both comfort today and opportunity for the future.

2640 Birdseye Creek Road, Gold Hill

$649,000
3 Beds 2 Baths 220222193 MLS
This is the kind of property million-dollar estates are built on. This beautiful one-owner 3.49-acre property captures the best of country living in an incredible natural setting, all just 5 minutes from downtown Talent. Enjoy sweeping views, Wagner Creek frontage, full TID irrigation, and a high-producing well. The level, usable acreage offers endless possibilities, whether you're dreaming of horses, a hobby farm, or a private country retreat. The property also features a chicken coop and an established orchard with pear, apple, and plum trees, providing the opportunity to enjoy fresh fruit right from your own backyard. Properties with this much usable land, abundant water, stunning views, creek frontage, and established agricultural features are becoming increasingly difficult to find.

7355 Wagner Creek Road, Talent

$569,000
3 Beds 2 Baths 220222554 MLS
Perched atop a private hill just outside of Jacksonville, this one-of-a-kind retreat offers breathtaking views stretching across mountains, valleys, and Southern Oregon skies. Situated on just over 40 acres, this 3-bed, 2-bath home was designed to embrace its incredible setting with expansive windows, multiple outdoor viewing areas, and a deck perfect for stargazing or soaking in unforgettable sunsets. The main living space is open and inviting, while the downstairs wood stove helps heat the entire home. The lower level includes a single-car garage and additional living space, creating a functional layout with room to spread out. Private, peaceful, and truly unforgettable--this is your chance to own a rare hilltop sanctuary just minutes from the charm of Jacksonville. Please no drive-bys.

1528 Morton Way, Jacksonville

$767,000
2 Beds 2 Baths 220222465 MLS
Custom round home designed and built by architect Clair Killen, positioned to capture panoramic views of Dutchman Peak and Little Grayback Mountain. The lower-level solarium provides exceptional space for year-round gardening and plant cultivation. Backing to BLM land, the property offers privacy, direct access to miles of public land, and a network of neighborhood trails, including a trail from the property that connects to the Sterling Mine Trail system. A gardener's paradise with two wells, extensive water storage, and two greenhouses with underground power. Multiple outbuildings and an ADU provide flexibility for guests, multigenerational living, rental income, hobbies, or workspace. Whether you're a gardener, homesteader, artist, or outdoor enthusiast, this property offers the space and infrastructure to bring your vision to life. Owner may carry.

9595 Sterling Creek Road, Jacksonville

The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

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. Listing content is copyright © 2018 SOMLS, Medford, Oregon. Last updated: