‘Irreplaceable’ 2,000-Acre Napa Valley Ranch With 4 Homes and a Vineyard Lists for Sky-High Price of $100 Million

A "once in a lifetime" opportunity to purchase a sprawling 2,000-acre Napa Valley ranch with four homes, 40 acres of vineyards, nearly 800 plantable acres, a private lake, and ponds has just hit the market in Saint Helena, CA, for an eye-watering $100 million.

The wine-making property has crushed its way to the top spot of the week's most expensive homes list.

Known as Glendale Ranch, the ecologically diverse estate has been in the same family for generations and has produced its legendary wine for more than a century.

The property featuring "ancient Douglas fir forests, cascading waterways, and heritage vineyards" was originally owned by late oil magnate David Fasken, who purchased the ranch in the 1930s. According to The Wall Street Journal, Lindsey Wiseman and her husband, Andrew Green, live on the property with their two young sons. Fasken was Wiseman’s great-uncle.

A primary white house built in the 1880s has wraparound porches to soak in the views. Three more residences located across 17 parcels would be ideal for multigenerational living and could also be used for rental income.

The enormous property also has a 7-acre private lake, ponds, and secured water rights to the year-round Conn Creek. Other highlights include paved roads, improved dirt roads, and an "extensive network of utilities and water."

More jaw-dropping estates to make the week's most expensive homes list include a recently completed coastal compound on Martha's Vineyard, a 102-acre New York estate with 66-car auto showroom, and Rockstar Energy Drink creator Russell Weiner's over-the-top Utah mansion returning once again to the market.

10. 1145 Arden Rd, Pasadena, CA

Price: $45,000,000

Arden Villa: The William K. Jewett House and Gardens located on 2.95 acres is owned by co-director of "Avengers: Endgame," Anthony Russo, who bought it for $15,579,500 in 2019.

The eight-bedroom compound, which has served as the backdrop for numerous film and TV shoots, including the famous lily pond catfight scene in the 1980s primetime soap opera “Dynasty,” underwent a "massive renovation" the same year Russo purchased it.

Built in 1913, the 18,565-square-foot estate now boasts modernized systems, handcrafted details, structural updates, main and secondary residences, and a Hollywood-style screening room.

Also found on the property are two pools, a tennis court, greenhouse, formal gardens, as well as the legendary lily pond, now lovingly referred to as a "reflecting pond."

Brent Chang of Compass is the listing agent.

9. 6355/6335 N Red Tail Rd, Jackson, WY

Price: $47,000,000

Antelope Trails Ranch: Located beneath the peaks of the Teton Range, this 69.07-acre ranch offers more than 920 feet of frontage along Snake River.

Three residences "designed to integrate with their natural surroundings" can be found on the property. A six-bedroom Main House has multiple fireplaces, game room, conference room, screening room, and hot tub.

The two-bedroom Woods House features an outdoor lounge overlooking a trampoline, swing, and treehouse. A two-bedroom Gate House has a loft and special event space that can accommodate up to 50 guests along with a wet bar.

Currently being used as an investment property that has hosted events, retreats, and weddings, the property also features a network of private trails used for hiking, biking, walking, cross-country skiing, snowmobiling, and snowshoeing.

Huff Vaughn Sassi of Jackson Hole Sotheby's International Realty is the listing agent.

8. 15 Forever Wild Way, Edgartown, MA

Price: $49,000,000

Great Point: Located on the island of Martha's Vineyard, this coastal estate nestled within the 200-acre Herring Creek Farm enclave is owned by tech entrepreneur and investor Michael Bronner.

Located on 31.59 acres with more than 2,500 feet of shoreline overlooking Edgartown Great Pond, the "extraordinary" property offers the "rare opportunity" to build three additional homes on "five parcels of contiguous land." The recently completed 12-bedroom legacy compound features a custom-built primary estate, a guesthouse, and several cottages.

The enormous lot also boasts mature trees, organic gardens, and a "protected waterfront."

Maggie Gold Seelig of MGS Group Real Estate is the listing agent.

7. 2 E 67th St Fl 9, New York, NY

Price: $49,000,000

Central Park views: This five-bedroom co-op built in 1927 and designed by architect Rosario Candela has been "fantastically reimagined" to now offer a sun-soaked open floor plan with expansive windows to enjoy views from all four exposures.

A private elevator provides access to an entry hall that opens up to a gallery with corner living room and dining room for entertaining. Other highlights include a wood-paneled library, a gourmet kitchen with pantry, and a corner primary suite with spa-inspired bathroom.

Opulent finishes include Juno limestone panel floors, ebonized walnut paneling, Italian leather paneling, and angled bronze trim.

The building also has a full-time doorman, porters, a fitness center, and wine cellar storage.

Serena Boardman of Sotheby's International Realty - East Side Manhattan Brokerage is the listing agent.

6. Bedford Corners, NY

Price: $49,500,000

Devonshire: With an address so exclusive it is withheld by the seller, this 101.6-acre retreat was built in 1901 for financier J. Borden Harriman.

The Gilded Age estate last traded hands in 2012 for an undisclosed sum and "set a record as the highest residential sale in Westchester County history," according to the listing. A grand main residence is undergoing a "substantial expansion" but offers the next buyer a unique opportunity to custom curate the remaining finishes.

Also found on the massive lot are a 66-car auto showroom and several "elegantly renovated" residences designed for multigenerational living, guests, or staff.

Brian Sheerin of William Raveis Real Estate - Katonah is the listing agent.

5. 4 E 66th St Fl 7, New York, NY

Price: $55,000,000

Upper East Side co-op: This five-bedroom co-op is owned by Rajaram Rao, founder of the infrastructure investment firm Global Infrastructure Partners, and his wife Anjuli Rao.

Last year, the couple purchased the property for $37 million from Sarah Solomon and the trust of her late pharmaceutical executive husband Martin, who also originally listed it for $55 million. Built in 1919 and designed by architect J.E.R. Carpenter, the limestone building features a private elevator that opens up to the seventh floor residence.

Historic highlights found inside the opulent estate include oversized windows, built-in bookcases, and three fireplaces. Lavish amenities include a grand living room, a library with Central Park views, a wood-clad dining room, an en-suite office, a chef's kitchen with marble countertops, and a corner primary suite with two dressing rooms.

A ground-floor guest apartment that transfers with the sale has a modern kitchen and bathroom. The building also boasts a full-time doorman, porters, and resident manager.

Serena Boardman of Sotheby's International Realty - East Side Manhattan Brokerage is the listing agent.

4. 253 White Pine Canyon Rd, Park City, UT

Price: $55,000,000

Monitor's Rest: Rockstar Energy Drink creator Russell Weiner is once again looking to part ways with his over-the-top estate that boasts everything from a wellness wing to a dedicated ski room.

Weiner purchased the six-bedroom mansion in May 2022 for $39.6 million and has been trying to sell the amenity-rich estate since 2023 with price fluctuations varying from $44,950,000 to $60,000,000 over the years.

The ski-in, ski-out retreat nestled in The Colony at White Pine Canyon features ornate details, including a copper roof, Croatian limestone, shou sugi ban charred cypress, and Italian thermally broken steel. Found throughout the 17,567-square-foot interior are a wellness system designed to calibrate "circadian lighting, air, and water around the clock," an "oxygen-regulated" primary suite, a fitness center, and a Himalayan salt massage room with oxygen system, hammam, cold plunge, infrared sauna, and hot tub.

The 4.97-acre mansion also has a club room with full bar and floating fireplace, a home cinema, bowling alley, golf simulator, indoor sports court with climbing wall, a room "for grandchildren" with eight queen bunkbeds, and an attached guesthouse for extended stays or staff accommodations.

Paul Benson of Engel & Volkers Park City is the listing agent.

3. 2 Park Pinnacle 49th Pl Ph And, New York, NY

Price: $59,000,000

The Woolworth Tower Residences: This Pinnacle Penthouse is owned by the chief executive of online art-investment platform Masterworks, Scott Lynn, who purchased it in 2023 for $30 million.

The 9,680-square-foot crown jewel is being offered with "the potential for an approved combination of the 49th floor" that would provide the next buyer a massive 12,131-square-foot estate. Built in 1910, the Thierry W Despont-designed condo boasts a private elevator, three bedrooms, a customizable floor plan, and the opportunity to own a mile-high estate in the sky located 727 feet above the ground with a private 408-square-foot observatory terrace.

Offering panoramic skyline views of New York City, the residence will be "delivered in designer ready white-box condition."

Community amenities found in the 32-unit building include a lounge, fitness studio, pool, and a wine cellar with tasting room.

Joshua Judge of Sotheby's International Realty - East Side Manhattan Brokerage is the listing agent.

2. 36 E 63rd St, New York, NY

Price: $60,000,000

Neo-Georgian mansion: This "exceptionally wide" Upper East Side townhouse once owned by former chairman of Revlon Ron Perelman was reportedly sold to a foreign LLC in February 2026 for $46.75 million.

Built in 1929, the 10-bedroom brownstone boasts 15,875 square feet of opulent space. Double-wide doors open up to an oak-paneled gallery, a book-lined study, a living room with two fireplaces, and an entertainer's kitchen with breakfast room.

Originally designed as the Hanger Club, a private club for aviators, the enormous estate now features a lavish primary suite spanning the entire third floor that has dual dressing rooms, a sitting room, and two bathrooms.

A rooftop terrace is ideal for soaking in the skyline views. The lower level features a movie room, a wine cellar, staff kitchen, and fitness center.

Serena Boardman of Sotheby's International Realty - East Side Manhattan Brokerage is the listing agent.

1. 750 Conn Valley Rd, Saint Helena, CA

Price: $100,000,000

Glendale Ranch: This 2,000-acre property in Napa Valley boasts four homes and a 40-acre vineyard featuring more than 20 acres of cabernet sauvignon, four acres of malbec, along with additional plots of petit verdot, petit syrah, and merlot.

The enormous sanctuary that has been producing wine for more than a century also has ancient Douglas fir forests and "cascading waterways." A historic White House built in the 1880s has wraparound porches to take in the serene views. Designed as a legacy compound, the property also encompasses three additional residences that could be used for rental income or staff accommodations.

There is a 7-acre private lake along with ponds, wells, and access to the year-round Conn Creek with secured water rights.

Erin Lail of Coldwell Banker Brokers of the Valley - St. Helena is the listing agent.