Lenny Sharp did not take the usual road into real estate. He spent 38 years in high tech, beginning in 1983 at Eagle Computer, with a 1987 stop at PCs Limited, the company that became Dell, and later product management at Western Digital and a four-year assignment in Japan. Today he leads the Sharp Mountain Homes Team, brokered by eXp Realty, out of Oakhurst, California, serving the gateway communities around Yosemite: Oakhurst, Bass Lake, Ahwahnee, Coarsegold, North Fork, Fish Camp, and Mariposa. His focus is short-term rentals and vacation properties, and he approaches the work less like a salesman and more like an operator.
Most of his clients are Bay Area and Los Angeles professionals who want a mountain place near Yosemite for their family and want vacation rental income to cover much or all of the cost of owning it. He and his wife Teresa have hosted vacation rentals since 2016 as Airbnb Superhosts, earning more than 850 five-star guest reviews across properties in Mariposa, Oakhurst, and San Antonio, Texas. Since getting licensed in 2021, he has closed 85 transactions totaling over $37 million, including 54 short-term rental deals, and his 2025 volume alone topped his first four years combined. He built his own deal analysis app on licensed AirDNA data, without a development team.
His team has earned RateMyAgent awards in both 2025 and 2026, including County Winner for Madera County and City Winner for Oakhurst and Mariposa, with 49 verified five-star reviews and an Agent of the Year badge. For the families who hire him, that mix of data and lived experience is the whole point.
From Dell to the Mountains
The path started in Japan, where Lenny and Teresa hosted so many guests and family members that when they came home, they decided to try hosting for real. In 2016 they bought a house in Oakhurst with a rental unit downstairs, and for three years Lenny commuted to the Bay Area every week. When COVID hit, he negotiated a separation package, and Teresa had the idea that he should become a Realtor. His first deal came from a Bay Area agent friend with 40 years in the business who trusted him to help him buy in the mountains. “Real estate gave me something tech never did: control over my own destiny,” he explained. His first four years were steady, about ten deals a year, before 2025 brought a breakout of 31 closings and $16.2 million in volume.
An Operator, Not a Theorist
A decade of hosting shapes how Lenny advises buyers. His three short-term rentals gross roughly $130,000 a year combined, and he knows what guests pay for, what breaks, and what a five-star stay requires. He also underwrites like an investor. “If the numbers depend on unrealistic assumptions, I say so, even if it kills the deal. My job is to protect my client’s money, not to close a transaction,” he said. That discipline extends to revenue others miss. On one four-bedroom listing, the conservative whole-house projection was about $78,000 a year. Listing the units separately and pricing each month to its occupancy pattern modeled closer to $131,000 in projected gross, before expenses.
Tools He Built Himself
Lenny licenses market data from AirDNA and built an STR Deal Analyzer on top of it, filtering comparable rentals by the amenities that actually drive revenue, such as hot tubs, views, and game rooms. Clients see what a property can realistically earn rather than a best-case guess. In 2026, he launched sierra-nevada-str.org to bring that same analysis to investors across the Sierra Nevada, along with hostmade.co, which turns an Airbnb listing link into an AI-search-optimized marketing website, complete with a narrated video walkthrough, in a few minutes. He also teaches other agents to use AI as a digital employee through a free flagship class, with four more on the way. He and his development partner also recently launched realtymade.co, which uses the HostMade engine to turn real estate listings into AI-searchable websites that send buyers to the listing agent, not to competing agents.
The shift is already showing up in his own business. About a third of his recent closings came from his YouTube channel and BiggerPockets, and several 2026 buyers found him through AI chatbots like ChatGPT while searching for a short-term rental agent near Yosemite. Often the AI surfaces him first and the buyer goes to his YouTube channel next. One client, a development leader at Google, sent him a screenshot of the AI search result that turned him up. “Buyers are researching with AI now,” he said. “That is exactly why I built HostMade.”
Can You Legally Rent It? Know Before You Offer
Much of his value sits in the details buyers learn too late. Madera and Mariposa Counties regulate short-term rentals very differently: Madera’s process is faster, cheaper, and less restrictive than Mariposa’s. In neither county does a vacation rental permit transfer to the buyer, so he structures escrows around permit timing to protect a client’s first busy season. Septic capacity, fire insurance, occupancy limits, and transient occupancy tax all shape what a property can legally earn. His advice to owners is just as practical. “Build a destination, not a crash pad,” he said, noting that based on comparable rentals in his market, a hot tub alone can add around $20,000 a year in gross revenue.
The Tiny Home Opportunity
Tiny homes are the opportunity he sees most often overlooked. Many of his clients already own land that could support a second dwelling, which means untapped income on property they already have. The guest demand is there, too. Travelers coming to Yosemite want more than a place to sleep. They want a stay that feels like part of the trip, and a well-designed tiny home delivers that in a way a standard cabin often can’t. One of his clients now grosses about $125,000 a year from his tiny home. The catch most people miss is a legal one: a tiny home on wheels is registered as an RV, and Madera and Mariposa Counties will not permit one as a vacation rental. That is why Sharp Mountain Tiny Homes offers homes built on permanent foundations, designed as two-bedroom units because that is where bookings are strongest. And for qualifying owners who have already used bonus depreciation on an existing rental, a tiny home can open another opportunity for that strategy, subject to a cost segregation study and their own tax advisor’s guidance.
What Comes Next
The plans ahead include growing Sharp Mountain Tiny Homes and HostMade, expanding his AI curriculum for agents, and recruiting agents who want to run their business the way he runs his. At 68, he shows no sign of slowing down. “I get up before 5 every morning, create a song, code my app, and go sell houses. I’m having a great time,” he said. The songs are made with Suno and are often personalized gifts for clients. For his clients, that energy comes with something steadier underneath it: honest numbers, local knowledge, and a team that stays with them long after closing.
Lenny Sharp, CA DRE #02142596, leads the Sharp Mountain Homes Team, brokered by eXp Realty, in Oakhurst, California. Learn more at lennysharp.com and sharpmountainhomes.com.
