The five highest-priced home sales reported in the Santa Cruz–Watsonville Area, California for the week ending October 25, 2026, were all in the city of Santa Cruz, and together they totaled $15.43 million. The group runs from an oceanfront property on Pleasure Point to a Victorian, with an architect-designed midcentury home, a home in a golf-course community and a custom home on a hillside in between.
No. 1 — $4,400,000 · 3020 Pleasure Point Dr, Santa Cruz, California
The week’s top sale was an oceanfront property at the tip of Pleasure Point, where 3020 Pleasure Point Drive sold for $4,400,000. The 8,886-square-foot lot has the Pacific on three sides. Its views span 200 degrees across Monterey Bay, and the surfers at Sewer Peak are close enough to pick out from the deck.
The home on the site was built in 1980 and has four bedrooms, four baths (three full and one half) and 3,156 square feet. Inside are vaulted and open-beam ceilings and skylights, and there are two fireplaces, one in the living room and one in the primary bedroom. A two-car garage completes the home.
The listing presents the site as much as the home. It includes conceptual renderings by Fuse Architecture for a modern surf house drawn for this lot, with broad expanses of glass, rooftop living space and rooms turned toward the water, and it notes that the current home could instead be renovated. The listing says coastal permits, architectural plans and seawall approvals are already in place.
The Strock Team of eXp Realty of California Inc was the listing agent, and Benjamin Strock of eXp Realty of California Inc represented the buyer.
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No. 2 — $3,600,000 · 39 Ortalon Ave, Santa Cruz, California
Architect Kermit Darrow, AIA, designed 39 Ortalon Avenue in 1962 around an idea he called “Light for Living.” Daylight moves through the rooms from morning to evening, and the interior opens directly to the outdoors.
According to the listing, the same family owned the home from the time it was built, and this was the first time it was offered publicly. The one-story home, on the Upper Westside, has four bedrooms, two baths and 2,982 square feet on a 9,975-square-foot lot. It has vaulted ceilings and skylights, and fireplaces in both the living room and the family room.
Darrow’s design was kept intact as the home was brought up to date. The kitchen was updated with Miele appliances, the bathrooms were redone, and the home has radiant-heated floors and owned solar panels. Joni Janecki & Associates redesigned the outdoor entertaining areas.
The home went under contract 12 days after it was listed and sold for $3,600,000, which was $400,000 above its asking price of $3.2 million. Eli Karon and Nicole Karon of Karon Properties were the listing agents, and Neal Langholz, also of Karon Properties, represented the buyer.
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No. 3 — $3,202,000 · 22 Hollins Dr, Santa Cruz, California
In Pasatiempo, a community with a golf course designed by Alister MacKenzie, the home at 22 Hollins Drive sold for $3,202,000. It sits at the end of a quiet lane, with views of the golf course and Monterey Bay.
Built in 1990, it is the newest of the five homes and the largest, with 4,677 square feet on two stories. It has four bedrooms and four baths, and its 0.40-acre lot is the biggest in the group.
The home has two primary suites, one of them on the main level, plus a dedicated office. The island kitchen has a butler’s pantry and opens to dining areas that look out on the gardens and the pool. An entertainment room has a wet bar and a fireplace, and its windows look across the golf course to the bay. A living room and a formal dining room give the home more space for guests, and there are three fireplaces in all.
Outside, the pool is set in stone decking. Rose gardens and mature fruit trees share the grounds with stone courtyards and patios. A detached guest area and a poolside bonus or game room with a full bath add room beyond the main home.
The Janie Hanson Team of KW Thrive Santa Cruz was the listing agent, and Greg Lukina of David Lyng Real Estate represented the buyer.
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No. 4 — $2,304,190 · 419 Locust St, Santa Cruz, California
Built in 1885, the Victorian at 419 Locust Street is the oldest of the five homes. It stands at the end of a cul-de-sac on a lot planted with fruit trees and flowers, near the heart of Santa Cruz and a short drive or bike ride from the Santa Cruz Beach Boardwalk and the coast.
The home has five bedrooms, four baths and 3,440 square feet on three stories, on a 10,585-square-foot lot. A studio on the top floor has its own kitchenette and bathroom. An attached accessory dwelling unit of 646 square feet has one bedroom, one bath and its own entrance, and a large barn stands at the rear of the property. The property last sold for $290,000 in 1986, 40 years ago.
The home went under contract 12 days after it was listed and sold for $2,304,190, which was $205,190 above its asking price of $2.099 million. Logan Andren of Andren Homes Inc was the listing agent, and Caroll Basile of Bailey Properties represented the buyer.
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No. 5 — $1,925,000 · 117 Esmeralda Ct, Santa Cruz, California
Near the top of the hill in Carbonera Estates, the custom home at 117 Esmeralda Court sits at the end of a quiet cul-de-sac, with views across DeLaveaga Park and the neighborhood to the ocean. It was built in 1988 and sold for $1,925,000.
The home has four bedrooms, four baths (three full and one half) and 3,800 square feet on two stories, on a 9,583-square-foot lot. The primary suite and a second bedroom are on the main level, along with living and dining spaces, a separate den and a kitchen ringed by windows. Downstairs, a large family room has a bar and a fireplace, and two more bedrooms share the level with flexible space for an office, a gym or guests.
The home has owned solar panels and an attached two-car garage with Level 2 EV charging. It is minutes from downtown Santa Cruz, about 30 minutes from San Jose and convenient to Highway 17. The property last sold for $1.01 million in 2008.
Michael Heffner of 1st Class RealEstate Mavericks was the listing agent, and the home went under contract 28 days after it was listed. Gizelle Sipin of Christie’s International Real Estate Sereno represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 25, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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