Live Oak/ Pleasure Point

Far from the tourist-filled beaches of downtown Santa Cruz, the Eastside neighborhoods offer an authentic taste of the California surf life. In the inland suburb of Live Oak, once seen as Santa Cruz's country cousin, cute bungalows and local gems like People's Coffee are bringing new energy. But it's the oceanfront enclave of Pleasure Point that remains the star, with its charming beach cottages, epic waves, and the legendary surf pioneer Jack O'Neill calling it home. The tight-knit community centered around 41st Avenue boasts a funky district packed with surf shops, sushi spots, and thrift stores that exude the ultimate laidback, surf town vibe. While downtown may be crowded, the Eastside is where you'll find the heart and soul of Santa Cruz surf culture.


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Aerial view Live Oak, Pleasure Point

Real Estate Statistics

Average Price $2M
Lowest Price $2K
Highest Price $23M
Total Listings 181
Avg. Price/SQFT $925

Property Types (active listings)

Search Live Oak/Pleasure Point Real Estate Listings

   

More about Live Oak / Pleasure Point

Live Oak is a sought-after coastal neighborhood for visitors and homebuyers alike. Its coveted beachfront homes offer breathtaking vistas of the Pacific's azure waters and Santa Cruz's iconic sandy beaches. This idyllic community is also revered by surfers for its world-class waves at Pleasure Point, one of California's premier surf breaks. With its stunning natural beauty and iconic surf culture, it's easy to see why Live Oak captures the hearts of all who visit this seaside paradise.

The Live Oak neighborhood stretches along the Santa Cruz coastline between the vibrant city of Santa Cruz and the charming village of Capitola. From beachfront condos at the Santa Cruz Yacht Harbor to the cliffside estates overlooking Capitola, Live Oak real estate offers homebuyers an abundance of options.

Some of the most coveted properties line the scenic East Cliff Drive, granting direct access to premier Santa Cruz beaches and world-class surf spots like Pleasure Point. The Live Oak community boasts a strong sense of togetherness with many parks, beaches, community centers, and local businesses bringing neighbors together. For homebuyers seeking coastal living in a lively yet intimate community, Live Oak provides the ideal blend of natural beauty, amenities, and small-town charm.

Pleasure Point, a popular surfing spot on the coast east of Soquel Point toward Santa Cruz, has an intriguing name with an embellished backstory. Local lore claims it was named for a rumored 1930s brothel, but the name derives from a mansion called The Owls that once stood on the site. The beach below was originally called Houghton's after A.D. Houghton, who built the mansion after retiring in 1903. Though the mansion burned down in 1914, its basement was filled with seawater and became a swimming pool. Later renovated into the Pleasure Point Plunge health spa, it remained a local attraction until going bankrupt in the mid-1950s, giving Pleasure Point its memorable name.


Restaurants

Shadowbrook Restaurant
Categories: American Restaurants, Banquet Rooms, Event Planning, Lounges, Nightlife, Restaurants
1750 Wharf Rd., Capitola CA 95010

Johnny's Harborside Restaurant
Categories: American Restaurants, Foods, Restaurants, Seafood Restaurants
493 Lake Avenue, Santa Cruz CA 95060 (831) 479-3430

The Crow's Nest Restaurant
Categories: American Restaurants, Bars, Banquet Rooms, Stand Up Comedy, Event Planning, Happy Hour / Game Nights, Lounges, Live Music Bars, Nightlife, Restaurants, Seafood Restaurants
2218 E Cliff Drive, Santa Cruz CA 95062

Harbor Cafe
Categories: American Restaurants, Breakfast/Cafe Restaurants, Cafes, Restaurants, Event Spaces
535 7th Ave., Santa Cruz CA 95062

Chaminade - Linwood's Bar and Grill
Categories: Restaurants
One Chaminade Lane, Santa Cruz CA 95065 (831) 475-5600

The Point Chophouse & Lounge
Categories: Bars, Nightlife, Restaurants, Steak Restaurants
3326 Portola Dr., Santa Cruz CA 95062

Lago Di Como
Categories: Italian Restaurants, Restaurants
21490 E Cliff Dr., Santa Cruz CA 95062

Dharma's
Categories: Restaurants, Vegetarian Restaurants
4250 Capitola Rd., Capitola CA 95010

Silver Spur
Categories: Breakfast/Cafe Restaurants, Cafes, Diners, Restaurants
2650 Soquel Dr., Santa Cruz CA 95065

Taqueria Michoacan
Categories: Mexican Restaurants, Restaurants, Burrito Places
21401 E Cliff Dr., Santa Cruz CA 95062

East End Gastropub
Categories: Bar, Restaurants
1501 41st Ave., Capitola CA 95010

Pleasure Pizza East Side Eatery
Categories: Pizza Restaurants, Restaurants
800 41st Ave., Santa Cruz CA 95062

New Leaf Community Markets
Categories: Delis and Meats, Markets and Specialty Foods, Grocery Stores, Restaurants, Sandwich Shops
1210 41st Ave., Capitola CA 95010

Canton
Categories: Chinese Restaurants, Foods, Lounges, Nightlife, Restaurants
900 41st Ave., Santa Cruz CA 95062

Cafe El Palomar
Categories: Breakfast/Cafe Restaurants, Cafes, Caterers, Event Planning, Food Services, Mexican Restaurants, Restaurants
2222 E Cliff Dr., Santa Cruz CA 95062

Leo's Taco Bar
Categories: Mexican Restaurants, Restaurants
1710 Brommer St,. Santa Cruz CA 95062

Canton Restaurant
Categories: Restaurants
820 41st AveSanta Cruz CA 95062

Kaito
Categories: Restaurants
830 41st Ave., Santa Cruz CA 95062

Star Bene
Categories: Argentinian Restaurants, Italian Restaurants, Restaurants
21245 E Cliff Dr., Santa Cruz CA 95062

Betty Burgers
Categories: American Restaurants, Burger Joints, Restaurants
1000 41st Ave., Santa Cruz CA 95062

Takara Japanese Restaurant
Categories: Japanese Restaurants, Restaurants, Sushi
3775 Capitola Rd., Capitola CA 95010

El Jardin Restaurant
Categories: Mexican Restaurants, Restaurants
655 Capitola Rd, #102, Santa Cruz CA 95062

Suda Restaurant
Categories: American Restaurants, Bars, Nightlife, Restaurants
3910 Portola Drive, Santa Cruz CA 95062

Tacos Moreno
Categories: Mexican Restaurants, Restaurants
1601 41st Ave., Capitola CA 95010

Wharf House Restaurant
Categories: American Restaurants, Restaurants
1400 Wharf RoadCapitola CA 95010

Aloha Island Grille
Categories: Asian Fusion, Hawaiian Restaurants, Restaurants
1700 Portola Dr., Santa Cruz CA 95062

Guang Zho Chinese Restaurant
Categories: Chinese Restaurants, Restaurants
3150 Portola Dr., Santa Cruz CA 95062

Chill Out Cafe
Categories: Breakfast/Cafe Restaurants, Cafes, Live Music Cafes, Restaurants, Burrito Places
860 41st Ave., Santa Cruz CA 95062

Taqueria Vallarta No 2
Categories: Mexican Restaurants, Restaurants, Burrito Places
893 41st Ave., Santa Cruz CA 95062

Chinese Village
Categories: Chinese Restaurants, Restaurants
3780 Capitola Rd., Santa Cruz CA 95062

Pizza My Heart
Categories: Pizza Restaurants, Restaurants
2180 41st Ave., Capitola CA 95010

Point Market and Cafe
Categories: American Restaurants, Cafes, Restaurants
E Cliff Dr at 32nd AveSanta Cruz CA 95062

L & L Hawaiian Barbecue
Categories: Barbeque, Restaurants
460 7th AveSanta Cruz CA 95062

Bamboo Garden Restaurant
Categories: Chinese Restaurants, Restaurants, Asian Restaurants
3744 Capitola Rd., Santa Cruz CA 95062

Kong's Market
Categories: Fast Food, Markets and Specialty Foods, Grocery Stores, Restaurants
400 26th Ave., Santa Cruz CA 95062

Amazon Juices
Categories: Brazilian Restaurants, Cafes, Markets and Specialty Foods, Juice Bars, Restaurants
1066 41st Ave., Capitola CA 95010

Betty Burgers
Categories: American Restaurants, Burger Joints, Restaurants
1000 41st Ave., Santa Cruz CA 95062

Casa Rositas
Categories: Mexican Restaurants, Restaurants
2608 Portola Dr., Santa Cruz CA 95062

Capitola Diner
Categories: Diners, Foods, Restaurants
1900 41st Ave., Capitola CA 95010

Whole Foods Market
Categories: Markets and Specialty Foods, Grocery Stores, Restaurants, Vegetarian Restaurants
1710 41st Ave., Capitola CA 95010

Roux Dat Cajun Creole
Categories: Cajun/Creole Restaurants, Restaurants
3555 Clares Street Ste T, Capitola  CA 95010

Dynasty Restaurant
Categories: Chinese Restaurants, Restaurants
3601 Portola Dr., Santa Cruz CA 95062

US Meal
Categories: Burger Joints, Restaurants
21505 E Cliff DrSanta Cruz CA 95062

Ihop
Categories: American Restaurants, Breakfast/Cafe Restaurants, Cafes, Restaurants
1549 41st Avenue, Capitola CA 95010

Chili's Grill & Bar
Categories: American Restaurants, Restaurants
1855 41st Ave Ste E1, Capitola CA 95010

Cole's BBQ and Catering
Categories: Barbeque, Caterers, Event Planning, Food Services, Restaurants
2590 Portola Dr., Santa Cruz CA 95062

Asian Express
Categories: Chinese Restaurants, Clothing & Accessories, Jewelry, Restaurants, Shopping, Vietnamese Restaurants, Asian Restaurants
1955 41st Ave Ste A-2, Capitola CA 95010

Conscious Creations Cafe Market And Bistro
Categories: Cafes, Restaurants
1121 SOQUEL AVE., Santa Cruz CA 95062

KFC
Categories: Restaurants, Fried Chicken Restaurants
2120 41st Avenue, Capitola CA 95010

Miyako Sushi
Categories: Restaurants, Sushi
1820 41st Ave, Ste G, Capitola CA 95010

Pleasure Pizza
Categories: Italian Restaurants, Pizza Restaurants, Restaurants
800 41st Ave., Santa Cruz CA 95062

Sunset Restaurant
Categories: American Restaurants, Restaurants
Chaminade Resort & Spa, Santa Cruz CA 95065

Pleasure Pizza
Categories: Pizza Restaurants, Restaurants
4000 Portola Dr., Santa Cruz CA 95062

Round Table Pizza
Categories: Pizza Restaurants, Restaurants
3715 Portola Dr., Santa Cruz CA 95062

McDonald's
Categories: Fast Food, Restaurants
1760 41st Ave., Capitola CA 95010

Upper Crust Pizza
Categories: Pizza Restaurants, Restaurants
2501 Soquel Dr., Santa Cruz CA 95065

Pink Godzilla
Categories: Japanese Restaurants, Restaurants, Asian Restaurants
830 41st Ave., Santa Cruz CA 95065

El Chino
Categories: Mexican Restaurants, Restaurants
2525 Soquel Dr, #A, Santa Cruz CA 95065

Naka Sushi
Categories: Restaurants, Sushi
851 41st Ave., Santa Cruz CA 95062

Coles Bar B Q
Categories: Barbeque, Restaurants
2590 Portola Dr., Santa Cruz CA 95062

Armadillo Willys BBQ
Categories: Barbeque, Restaurants
2180 41st Ave., Capitola CA 95010

Nuevo Southwest Grill
Categories: Caterers, Event Planning, Food Services, Mexican Restaurants, Restaurants
21490 East Cliff Drive, Santa Cruz CA 95062

Hot Dog On A Stick
Categories: Fast Food, Restaurants
1855 41st Ave , SPC #R-2, Capitola CA 95010

Brown Ranch Marketplace
Categories: Chinese Restaurants, Clothing & Accessories, Cosmetics, Jewelry, Restaurants, Shopping, Hair Salons/Barber Shops
3555 Clares St., Capitola CA 95010

Crush
Categories: Advertising Services, Automotive, Burmese Restaurants
4350 Clares St., Capitola CA 95010

Chipotle Mexican Grill
Categories: Mexican Restaurants, Restaurants
1955 41st Ave., Capitola CA 95010

Sushi Cafe
Categories: Restaurants, Sushi
3218 Virgil Ln., Capitola CA 95010

Far West Marine
Categories: Restaurants, Seafood Restaurants
493 Lake Ave., Santa Cruz CA 95062

Santa Cruz coast

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