Jackson Homes with Vineyard View

Welcome to Jackson County, Oregon, a picturesque gem nestled in the heart of the Rogue Valley. Known for its stunning landscapes, rich history, and vibrant culture, Jackson County is a haven for nature lovers, wine enthusiasts, and anyone seeking a serene lifestyle. With its rolling hills, lush vineyards, and breathtaking views of the Cascade Mountains, this region offers a unique blend of outdoor adventure and urban convenience.

One of the most enchanting features of Jackson County is the abundance of homes with vineyard views. Imagine waking up each morning to the sight of sprawling vineyards, their rows of grapes glistening in the sunlight, and the gentle sound of nature surrounding you. These homes are not just residences; they are a lifestyle choice, offering a tranquil retreat from the hustle and bustle of city life.

Whether you’re sipping a glass of local Pinot Noir on your deck or exploring the nearby wineries, living in a home with a vineyard view allows you to immerse yourself in the rich agricultural heritage of the region. Jackson County is home to several award-winning wineries and vineyards, making it a perfect destination for those who appreciate fine wine and scenic beauty.

In addition to its natural allure, Jackson County boasts a vibrant community with charming towns like Ashland, Medford, and Jacksonville, each offering unique shops, restaurants, and cultural events. With a mild climate, abundant recreational opportunities, and a welcoming atmosphere, Jackson County is truly a place where you can live your dream life amidst the beauty of vineyards and rolling hills. Come discover your perfect home with vineyard views in this enchanting corner of Oregon!

Newest Jackson Homes with Vineyard View

$739,000

4 Beds ⋅ 3 Baths ⋅ 220225931 MLS

Located just minutes from downtown, this impressive 2,596 sq. ft., 4-bedroom, 3-bathroom home features striking curb appeal and breathtaking views of Grizzly Peak. The bright interior boasts hardwood floors, formal and informal dining, and a spacious kitchen with solid-surface counters. Soaring ceilings frame the great room, which opens to an expansive deck overlooking a tiered backyard complete with garden boxes, a potting shed, and storage shed. Highlights include a main-level vaulted primary suite with a jetted tub and walk-in closet, a flexible upper-level bonus room with skylights, and carpeted guest bedrooms. Modern upgrades feature a new heat pump with advanced UV filtration, an electric vehicle charger, and an oversized attached garage with workshop space plus dedicated RV parking.

960 Oak Street, Ashland

$2,895,000

4 Beds ⋅ 6 Baths ⋅ 220225736 MLS

Welcome to a wine country retreat at the gateway to Jacksonville. Set on just over 10 irrigated acres, this Tuscany-inspired estate offers nearly 4,900 SF with Venetian plaster walls, barrel-vault ceilings, and exceptional finishes. The chef's kitchen opens to the family room with pool and vineyard views and features a 6-burner Wolf range, Sub-Zero fridge, breakfast nook, wine room, and Fisher & Paykel double dishwasher. The private primary wing offers a spa bath and sitting area, while three guest suites include walk-in closets and direct bath access. An office with fireplace and formal dining room complete the main level. Upstairs features a billiards room, theater, and steam shower. Outdoors, enjoy a 50,000-gallon beach-entry pool, travertine patios, outdoor kitchen, pergola, vineyard and mountain views, plus multiple garages and a shop.

3922 Bellinger Lane, Medford

$1,350,000

5 Beds ⋅ 6 Baths ⋅ 220225703 MLS

Live the Southern Oregon Dream! Welcome to an extraordinary Ashland estate where breathtaking views of Mount Ashland, the Cascades, downtown Ashland, and surrounding vineyards create a spectacular backdrop. Nestled behind a private gated entrance on 5 acres, 3 TID irrigated, this custom-built 5 bedroom, 6 bath home offers luxury, privacy, and versatility. Whether you're seeking a peaceful retreat, a multigenerational home, or space to operate a home-based business, this property adapts to your lifestyle. The thoughtfully designed floor plan features TWO private suites with their own entrance, ideal for extended family, a professional office, or creative studio. Garden beds, fruit trees, space for horses, animals, a 28 GPM well, RV hookups w/220, abundant parking, just minutes from the Shakespeare Festival, galleries, wineries and award-winning restaurants. You'll enjoy the best of country living without sacrificing convenience. Luxury. Privacy. Self-sufficiency. Endless possibilities.

808 Pompadour Drive, Ashland

$1,899,000

4 Beds ⋅ 4 Baths ⋅ 220225369 MLS

First time on the market for this one-of-a-kind custom ICF-built home with breathtaking panoramic views! This 4 bed, 3.5 bath, 4,972 sqft home offers a main-level office, multiple large storage rooms, and plenty of space for entertaining. The upper level features a spacious primary suite with a private balcony, plus (2) additional bedrooms and a bonus loft (not included in storage). The lower level is ideal for multigenerational living with a large entertainment area, wet bar, bedroom, bathroom, and bonus office/storage space. Situated on 14.78 acres, (house on 1 acre), 13.8 acres currently in hay production, with rare dedicated unlimited TID irrigation. Propane has been plumbed both interior and exterior to add a fireplace or connect your BBQ if desired. Also includes an approx. 1,500 sqft detached shop, barn with (6) 12x12 stalls, riding arena, plus (2) full RV hookups and 50-amp available at the barn, and endless opportunities for horses, livestock, or hobby farming.

40 Ashland Acres Road, Ashland

$1,790,000

4 Beds ⋅ 5 Baths ⋅ 220225149 MLS

VIEWS, VIEWS, VIEWS! This exceptional property with breathtaking panoramic views sweeping from Eagle Point to Ashland offers Victorian charm paired with modern comfort. Just under 5 Acres and almost 4300 sq ft, this 4 bedroom 5 bath residence, features two complete living quarters, each with its own full kitchen, private entrance, and laundry area, making it ideal for multigenerational living, family, guests, or rental income potential. The upper level is enhanced by balconies on each side of the home providing the perfect place to enjoy morning coffee and evening nights. Also featuring a Stiltz Elevator for convenient access to upper level. Main level of the home has a great floor plan with space for everyone inside and out with a covered porch. The four-car garage provides abundant space for vehicles, toys and storage. Ideally located just minutes from the historic town of Jacksonville, wineries, and shopping, this home is truly incredible.

4303 Tami Lane, Central Point

$795,000

3 Beds ⋅ 3 Baths ⋅ 220224946 MLS

Enjoy expansive views of the 9th fairway at Oak Knoll Golf Course, Grizzly Peak, and surrounding vineyards from this inviting 3-bedroom, 2.5-bath home. Located on a quiet cul-de-sac, the 1,995 sq.ft. residence offers peaceful golf course living with direct cart access. This well-maintained home features a new roof (January 2026), a large deck perfect for entertaining, and RV parking. Inside, you'll find both a living room and a spacious family room with an open vaulted ceiling, plus a kitchen with a new double oven and gas cooktop. The primary bedroom and bath are generous, with elegant cultured marble counters and shower surround. Additional highlights include HVAC with an advanced air scrubber filtration system and ADA accessibility. Ideal for those seeking a single-level lifestyle with stunning golf course and mountain views in a highly desirable Ashland location. A rare opportunity to own a golf-front home in one of Southern Oregon's most beautiful areas.

738 Fairway Court, Ashland

$795,000

3 Beds ⋅ 3 Baths ⋅ 220224732 MLS

Nestled in the heart of Southern Oregon's premier wine country, and close to the historic town of Jacksonville, this property on 4.98 acres offers the perfect blend of rural charm and functional infrastructure. The property features a magnificent, classic wood barn set against a backdrop of mature landscape, sweeping valley and mountain views. The home boasts bright, inviting living spaces, a spacious upstairs primary suite, a light-filled sunroom, and a private entrance leading to 2 downstairs bedrooms, 1 full bathroom and studio. Enjoy unique access to the Applegate river, IRRIGATION WATER RIGHTS dated from 1876 and the natural beauty of the surroundings. Bring your horses or enjoy it as a peaceful country retreat. A true Applegate gem waiting for its next chapter.

7935 Upper Applegate Road, Jacksonville

$1,675,000

3 Beds ⋅ 4 Baths ⋅ 317835913 MLS

Privately gated and gracefully set on 5 acres in the heart of Southern Oregon wine country, this extraordinary estate blends timeless craftsmanship, architectural elegance, and the rare luxury of a privately owned 250-vine vineyard. Constructed at a cost exceeding $2 million, the residence was thoughtfully designed to reflect enduring quality and sophisticated living at every turn. A striking custom stone exterior, crowned by an authentic 100-year slate roof, creates a commanding first impression, while the roofline was intentionally crafted to mirror the surrounding mountain vistas. Inside, soaring ceilings, rich custom woodwork, and polished vein-cut travertine flooring create an atmosphere of refined warmth and understated grandeur. Designed for both elevated entertaining and everyday comfort, the chef’s kitchen features premium appliances, exquisite custom cabinetry, expansive gathering spaces, and a fully appointed butler’s pantry. Walls of windows frame serene mountain views, inviting the beauty of the outdoors into the home’s luxurious interior. The primary retreat offers a true spa-inspired experience with dual private bathrooms and separate custom closets, creating a level of comfort and privacy rarely found. A separate VIP guest suite or executive office provides exceptional flexibility for extended stays, multigenerational living, or private accommodations. Beyond the residence, the estate unfolds into a lifestyle property unlike any other — complete with a producing 250-vine vineyard, manicured grounds, and a peaceful sense of seclusion just minutes from modern conveniences. Every detail reflects intentional design, uncompromising materials, and a vision of luxury meant to endure for generations. This is more than a home — it is a legacy estate to be experienced in person to be fully appreciated. One seller is a licensed OR Realtor.

727 EARHART RD, Rogue River

$2,500,000

4 Beds ⋅ 6 Baths ⋅ 220223748 MLS

Experience Southern Oregon luxury in this stunning custom-built home on 6.77 private irrigated acres. Featuring 5,597 sq ft of exquisite craftsmanship with crown molding, custom ceilings, and Brazilian teak wood floors. Relax by the gorgeous stone wood-burning fireplaces or entertain in the media room w/ open beam ceiling & large wet bar. The chef's kitchen boasts honed granite counters, a large island, Sub-Zero fridge, & Wolf appliances including double ovens & six-burner gas cooktop w/ griddle & warming drawer. Spacious primary suite on main floor offers 8-ft French doors to patio, marble & travertine bath with stone shower and body sprayers. Enjoy the large covered patios, heated gunite pool/spa with electric cover, and outdoor stone wood-burning fireplace. A 30x45 insulated shop with bath, office, storage, and upstairs studio completes this exceptional property. Privacy, luxury, and space--it has it all!

4244 Griffin Creek Road, Medford

$14,000,000

220223436 MLS

Offered for sale for the first time ever, Belle Fiore Estate Winery is a premier Southern Oregon winery 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 square feet 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 eight 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. The combination of established vineyard production, hospitality operations, event revenue, and significant growth potential creates a rare opportunity to acquire Oregon's most significant vineyard esta

100 Belle Fiore Lane, Ashland

$12,000,000

7 Beds ⋅ 19 Baths ⋅ 220223437 MLS

Offered for sale for the first time ever, Chateau at Belle Fiore Estate Winery is one of Oregon's most extraordinary residential estates. Spanning over 17,400 sqft across four 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 over 17 acres, including 12.1 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, four-car garage, prep kitchen, and grand gathering spaces complete this iconic Southern Oregon estate.

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 being offered for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,800 sqft; it has four levels, 5 bedrooms, 19 bathrooms, elevator service, a vineyard, a 2 bedroom 2500+ sqft carriage house, four-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 featuring 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, a priceless feature of this one of one opportunity to own Oregon's most significant vineyard estate.

100 Belle Fiore Lane, Ashland

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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: