Brian Elbogen couldn’t afford a house in San Francisco. So he bought one-third of a three-unit building. That got him wondering: Were there other ways to slice a home’s price down to a manageable size?

That insight led Elbogen to launch Jubilee Homes in 2024, built on a simple premise: You buy the house, Jubilee buys the land and rents it back to you. This model, called a land lease or leasehold, can shave six figures off a home’s price. In expensive markets, land accounts for more than half a home’s value. Jubilee buyers can put down just 1%–2% of the property price and trim their monthly mortgage by 20%.

“It helps buyers get their foot in the door,” Elbogen explains. “Everyone understands owning and renting, but there’s a big chasm between the two. This hybrid solution allows people to bridge the gap.”

A new spin on splitting a house

Residential leaseholds are common around the world, but are relatively rare in the US and have a bit of a bad rap. But as Elbogen points out, “We’ve gone through the history books and designed a version that ensures everyone has better outcomes.” For instance, the most Jubilee can raise “ground rent” is 3% per year. Buyers can buy the land at any time for up to 99 years. The buyout price means the homebuyer and Jubilee share proportionally in the property’s total value based on their initial investment. If homeowners choose to sell, they can recombine the house and land into a traditional sale. Unlike renters, they build equity; unlike traditional buyers, they pay a fraction of the price.

Leaseholds are just one of several approaches companies are using to make homeownership more accessible. Ownify lets buyers in with only 2% down, covers the rest of the down payment, and collects fixed monthly payments as equity builds. Acre Homes takes just 5% down and grants buyers half of the home’s appreciated value over five years. Although fractional ownership is often built for first-time buyers who need a foothold, investors have noticed the discount, too. But not all are eager to share.

“I don’t buy fractional ownership since you don’t have full control and may face a difficult exit,” says Shawn Zar, a real estate investor in New York City. “I prefer to own 100% of even a small property.”

Leaseholds, in particular, can come with risks: Not only can ground rent go up, but resale and refinancing can be complex, and some lenders may steer clear. And even in the best of circumstances, leaseholds and other fractional models come with fewer upsides and more tradeoffs: You pay less, but gain less—although you also risk less than you would pouring every last cent you have into a house.

“Owning a house can be a very concentrated bet on a single illiquid asset,” Elbogen points out. “By having less tied up in your house, you can diversify—with stocks, crypto, or even other real estate.”

Keep reading for a deeper dive into leasehold math and its downsides, including refinancing constraints, resale complexity, fine-print risk, and more.

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When Silicon Valley’s elite need to truly unplug, they head 25 miles away to Lupin Lodge, a nudist resort where they can leave everything at the door. In operation for nearly a century, this 110-acre property was listed in 2024 for $32.8 million, slashed to $29.2 million in 2025, and was recently pulled off the market to regroup. Listing agent Joseph Pollifrone at Just Realty opens up about why it’s been tough to sell.

Q: What’s this property’s story? “Once a winery that was closed during Prohibition, Lupin Lodge was founded by the Naturists during the Great Depression in 1935. It’s the oldest establishment of its kind west of the Mississippi. Over the decades, it has developed a loyal following, where guests come to connect with nature just minutes from Silicon Valley. It includes cabins, yurts, tent sites for camping, RV spaces, and common gathering areas, including a pool and a jacuzzi. ”

Q: It was for sale for over 400 days before being delisted. Why no takers? “The primary challenge is that properties with this much land, history, and infrastructure rarely come to market in Silicon Valley. The buyer pool tends to be specialized. Finding the right buyer is less about speed and more about aligning the property with someone who understands its potential.”

Q: What interest has it received? “A variety of groups, including hospitality investors, retreat operators, wellness organizations, and buyers exploring opportunities to reposition the property as a boutique resort, school campus, or conference center, as well as potential uses related to corporate retreats, educational programs, and wellness-focused experiences. But at this time, the owner has decided to temporarily take Lupin Lodge off the market while we re-evaluate before going back on the market in the future.”

Q: How well does it do as an investment currently? “Detailed financial information is available to qualified buyers under confidentiality agreements. What we can share publicly is that the property has operated successfully for many years with a long-standing guest community.”

Q: How did you end up with this listing? “Many have asked if I am a member. I am not. The owner was looking for a broker with experience marketing distinctive real estate assets.”

You don’t have to be Mark Zuckerberg or Oprah Winfrey to afford a piece of Hawaii. Here’s proof from Kristy Nakamura, a broker in Oahu at eXp Realty and co-founder of Your Oahu Home Team with her husband, Austin.

Single-family home median price: $1,205,000 (up 1.69% YoY)
SFH sales: 177 (up 5.99% YoY)
Condo median price: $500,000 (up 1.21% YoY)
Condo sales: 291 (down 0.68% YoY)
Average rent: $3,028/month (up 8.15%)

Pros: The island of Oahu—home to Honolulu and 70% of the Aloha State’s population—is actually a smart place to invest if you know how to navigate this unique market. “Limited land supply on an island means inventory stays tight and values hold,” Nakamura says. Plus, “Strong demand from military PCS relocations (over 50,000 active-duty personnel) creates consistent buyer activity year-round. Military rental demand near Joint Base Pearl Harbor-Hickam and Schofield Barracks keeps vacancy rates low.”

Cons: Home prices are among the highest in the nation. Luckily, “VA loans with zero down make homeownership accessible for a large buyer pool,” Nakamura explains. She and her husband specialize in helping military families use VA loans to buy homes. When these families get transferred elsewhere, the couple help convert their Oahu residences into rentals, adding, “That’s actually one of the most common investment paths we see here.”

Her advice: “Look at emerging neighborhoods like Ewa Beach and Kapolei for better entry prices with strong appreciation potential,” Nakamura says. And since leasehold properties are common in Hawaii and can complicate financing, make sure you’ve read our primer on leaseholds above.