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$3,495,000
4 Beds 3 Baths ML82054521 MLS Pasatiempo Property Owners Inc. BLDG.
The view is the headline. Expansive. Unforgettable. Ever-changing. Perched behind the gates of Pasatiempo, 16 Kite Hill Road is a captivating 4 bed, 3 bath, 3,119 sq/ft retreat offering true single-level living on nearly half an acre, wrapped in palms and tucked into one of the area's most peaceful settings. A quiet, palm-lined approach gives little away, then the home opens to sweeping panoramas of Monterey Bay, Santa Cruz city lights, mountain ridge lines and the fairways below. Arched windows, vaulted beamed ceilings and skylights frame the scenery and flood the interiors with light. Easy, single-level living flows from a custom kitchen anchored by a substantial island into open dining and living spaces, all connecting seamlessly to the outdoors. Step outside to an expansive stone patio built for resort-style living, with a built-in BBQ, sink, refrigerator, hot tub and fire pit overlooking the coast. A spiral staircase climbs to a private bonus view room, made for reading, working or watching the sunset with a glass of wine. Private. Peaceful. Transportive. Minutes from downtown, the beach and Hwy 17, yet once home, it feels like a permanent resort retreat.

16 Kite Hill RD, Santa Cruz

Listed by Strock Team, 831-688-9800 from eXp Realty of California Inc
(If provided) CoList: from

$2,499,000
3 Beds 3 Baths ML82050906 MLS
Nestled on nearly three acres in an exclusive gated enclave of the estate quality homes, this custom California Contemporary Mediterranean residence offers an extraordinary blend of privacy, natural beauty and timeless Craftsmanship. Located just 1.7 miles above the DeLaveaga golf course clubhouse, the property enjoys sweeping panoramic views across Monterey Bay. The grounds feature an orchard of more than 100+ year old olive trees originally planted in the 1880s by Jose Vicente DeLaveaga. The picturesque setting is enhanced by equestrian amenities, including double covered stalls, a tack room, and a fenced grazing area, ideal for horse enthusiasts. Inside, the home showcases exceptional custom tile work and fine wood craftsmanship throughout, while open-beam ceilings add warmth, character and architectural appeal. Thoughtfully designed living spaces capture the stunning ocean vistas from multiple vantage points, and an detached bedroom/office above the garage. Modern conveniences include a solar electric system, whole-house backup generator, and a shared mutual well water source. Combining historic significance, premium amenities, and breathtaking Monterey Bay views, this remarkable property presents a rare opportunity to experience the finest in California coastal living!

3430 Loma Alta LN, Santa Cruz

Listed by Randall Brown, 831-818-5055 from Coldwell Banker Realty
(If provided) CoList: from

$1,999,000
5 Beds 3 Baths ML82051212 MLS
AMAZING NEW PRICE! Santa Cruz View Retreat! This exceptional 5BR, 2.5BA home sits on 4+ acres of breathtaking, deer proof gardens w/ panoramic views from Monterey Bay to San Lorenzo Valley and the Summit. A well designed 2,587 ft floorplan offers serenity, privacy, and the quintessential Santa Cruz lifestyle. Enjoy full 360 vistas from the wraparound farmhouse porch w/ multiple areas for viewing sunrises, sunsets, or sailboat activity on the Bay. The property includes 2 garages, one w/ workshop, generator with propane tank, enclosed veggie gardens, metal gopher and rabbit proof planters, 2 Tuff Sheds, multiple outdoor living spaces. Stroll the gazebo, patios, decks & secret gardens. Listen to the quiet or to the gurgling fountains. Gardeners will love 20+ fruit trees, 2 greenhouses, mature landscaping & extensive brick and gravel pathways. Additional features include a dog pen with dog door, security system, auto drip & sprinkler irrigation systems. Located in an official Firewise community, this rare retreat offers peaceful, expansive living just minutes from town. Perfect for nature lovers, entertainers, and anyone seeking a truly 1 of a kind property. Owner spent decades infusing the property with whimsy, eclectic touches and an insatiable love of plants & garden spaces! WOW

200 McAmant DR, Santa Cruz

Listed by Frank Murphy Realty, 831-234-4343 from Frank Murphy Realty
(If provided) CoList: from

$4,498,000
4 Beds 4 Baths ML82049466 MLS Pasatiempo Home Owners BLDG.
Exquisite gated Pasatiempo residence overlooking the renowned Alister MacKenzie-designed golf course, recognized among the nations Top 100. Privately set at the end of a quiet lane, this exceptional property offers sweeping Monterey Bay and fairway views from many rooms. The thoughtful floor plan features two primary suites, one with a fireplace, one on the first floor, a dedicated office, and elegant living spaces designed to capture the stunning surroundings. The island kitchen with butlers pantry opens to the dining area overlooking the gardens and pool. Soaring ceilings, expansive windows, and abundant natural light enhance the warm, inviting atmosphere. The formal dining room, gracious living room with fireplace, and entertainment room with wet bar and spectacular golf course and Monterey Bay views create beautiful spaces for gathering. Outdoors, enjoy a pool with stone decking, rose gardens, mature fruit trees, stone courtyards, and multiple patios through French doors. A detached guest house offers comfortable accommodations, while the poolside bonus/game room with full bath provides flexibility as a recreation space, guest retreat, or private getaway. This exceptional residence blends elegance, comfort, privacy, breathtaking views, and the coveted Pasatiempo lifestyle.

22 Hollins DR, Santa Cruz

Listed by Janie Hanson Team, 831-345-7921 from KW Thrive Santa Cruz
(If provided) CoList: from

$2,495,000
6 Beds 4 Baths ML82048077 MLS
The Willey House at 105 Sylvar Street in Santa Cruz, is a historically designated Victorian residence set behind a canopy of mature trees on Santa Cruzs historic Mission Plaza. This iconic property blends timeless Stick-Eastlake architecture with rich local heritage and enduring character. Originally built in 1887 for Henry Willey, the first president of Peoples Bank, this distinguished 3,698 square foot residence showcases unparalleled craftsmanship. Expertly constructed from locally harvested old-growth heart redwood, the 6-bedroom, 4.5-bathroom residence stands as a testament to enduring quality. Every corner of the home tells a story, from its intricate woodwork, detailed stained glass, and steeply pitched rooflines to the inviting wrap-around porch and period detailing throughout. Tall windows flood the interior with natural light, highlighting soaring, vaulted ceilings, original millwork, and elegant living spaces designed for both entertaining and everyday living. The home offers City Views and an excellent Walk Score, making it a highly convenient commute location. The property also features a legal detached ADU with a dedicated separate entrance and private yard space that currently generates substantial income, providing financial flexibility and additional value.

105 Sylvar ST, Santa Cruz

Listed by Sam Bird-Robinson, 831-515-8582 from Compass
(If provided) CoList: Charlie Lambert from Compass

$4,588,000
4 Beds 4 Baths ML82047237 MLS
Some homes simply have an address; this one has a vantage point. From the moment you step inside 116 Monterey Street, a coastal panorama unfolds: Loma Prieta stands sentinel to the east, the iconic Santa Cruz Boardwalk and Wharf shimmer below, and the Monterey Bay Marine Sanctuary stretches to the horizon. This Mediterranean masterpiece was entirely reimagined in 2007 by the current owners, ensuring every detail was overseen with an owners eye for perfection. They meticulously preserved the vintage character, designing a high-end modern residence around that historic core.From the structural integrity to the lush,professional landscaping, every inch of this property has been built, lived in, and maintained to an immaculate standard.Situated just steps from West Cliff Drive and the Cowells Beach stairs, this residence caters to an active lifestyle centered around the ocean. The chef's kitchen, anchored by a Wolf range and a generous island, makes entertaining effortless. Evenings end in a private coastal oasis featuring an 8-person outdoor hot tub and a convenient outdoor shower, the essential finish to a morning surf session.The permitted 1bed/1 bath ADU sits atop a 2-car mechanic's garage and offers a proven income of $30-40k annually.

116 Monterey ST, Santa Cruz

Listed by Craig Springbett, 831-239-9966 from Christie's International Real Estate Sereno
(If provided) CoList: from

$2,750,000
4 Beds 3 Baths ML82039785 MLS
Price adjusted to reflect exceptional value in one of the Upper Westsides most soughtafter neighborhoods. Ocean View Santa Cruz, breathtaking views of the Santa Cruz skyline, and expansive panoramic unobstructed Monterey Bay full ocean view extending to Moss Landing, Monterey, and beyond. Enjoy the Giant Dipper, sailboat races, and colorful scenes of Santa Cruz. A gated entrance driveway, lined with custom exterior lighting, makes a striking statement. This iconic home boasts a great room filled with abundant natural light, floor-to-ceiling walls of windows, sliding glass doors, and high ceilings. Discover the grotto kitchen with an island gas cooktop and formal dining room. The spiral staircase leads to 4 rooms and 2 full bathrooms. A double-sided fireplace is the focal point of the cinema/play or billiard room, 1/2 bath, bar service room, and exclusive wine cellar. The sliding glass double doors lead to the pool, hot tub, sauna, and patio. BBQ entertain or relax while soaking in the ocean view. 2 car garage, pool house, garden, shed, security system, air conditioning, electric gate. Walkway bridge to downtown, shops, restaurants, Holy Cross School, Pognic Open Space hiking and biking trails, UCSC 3 min, Surfing 8 min, downtown 4 min, Urgent care 4 min, access Highway #1,17.

350 Highland AVE, Santa Cruz

Listed by Laura Lynn, 831-479-4894 from California Real Estate
(If provided) CoList: from

$6,799,000
3 Beds 2 Baths ML82042792 MLS
Wake up to panoramic ocean views spanning Monterey Bay at the former home of surfing legend Jack O'Neill on one of the most sought-after oceanfront stretches on the California coast. The ultimate coastal lifestyle combining exclusive privacy with unparalleled walkability to local restaurants, coffee collectives, and world-class surf. Privates Beach, The Hook, Pleasure Point, and Capitola Village are all within walking distance. Some properties ask you to imagine the potential. This one hands it to you. One of the very few oceanfront homes with significant coastal bluff protections already in place, including a hard-armor concrete seawall, rip-rap revetment, and anti-erosion netting. 4360 Opal Cliff Drive offers you the unique ability to bypass the notoriously complex and costly coastal entitlement process with approved plans and building permits for a customizable remodel. Acquire the home, pick your finishes, and start building. The opportunity is rare and the possibilities are endless. 1) Enjoy the vintage beach charm. 2) Remodel the existing footprint with your personal touches. 3) Go big; add the ground floor primary suite and 3-car garage for a 5BR, 4.5BA, 4,220 SF oceanfront compound with multiple lounge areas and a semi-detached ADU for a flexible guest suite or office.

4360 Opal Cliff DR, Santa Cruz

Listed by Megan Lyng, 831-345-0503 from David Lyng Real Estate
(If provided) CoList: Troy Hinds from David Lyng Real Estate

$5,650,000
3 Beds 3 Baths ML82041622 MLS
Properties like this rarely come to market. Built and completely reimagined in 2018, this home sits on a lot held by the same family since 1910 offering a truly special blend of history, craftsmanship, and modern luxury. From the moment you step inside, you are welcomed by sweeping views of the harbor, beach, lighthouse, and the iconic Santa Cruz Boardwalk in the distance. Expansive NanaWalls open the main living space to a wraparound stamped concrete patio, complete with both gas and wood-burning fire pitscreating effortless indoor-outdoor living thats perfect for entertaining year-round. The kitchen features a generous island and sleek finishes beautifully contrasted by rich Brazilian teak floors. A flexible Murphy bedroom just off the living room offers the ideal space for guests, a cozy lounge, or a private home office. Upstairs, accessible by stairs or an elevator that covers all levels, you will find dual primary suites and a stunning deck with panoramic ocean views your own private retreat above it all. A touch of the unexpected, hidden rooms are tucked behind custom bookcases throughout the home. Discover a secret staircase leading to the finished basement complete with a large recreation space, full bath, and second laundry or uncover your own lookout tower.

2974 E Cliff DR, Santa Cruz

Listed by Megan Lyng, 831-345-0503 from David Lyng Real Estate
(If provided) CoList: from

$5,400,000
8 Beds 6 Baths ML82037953 MLS
Perched atop 3.42 private acres overlooking Monterey Bay and the lights of Santa Cruz, this extraordinary legacy estate offers a rare blend of privacy, scale, and proximity to Silicon Valley. Designed for those who value both connection and retreat, the property presents an exceptional opportunity for multigenerational living, executive respite, or a private family compound. Expansive indoor and outdoor gathering spaces create an ideal setting for entertaining on any scale, from intimate family celebrations to grand events. Sweeping views, open grounds, and thoughtfully designed living areas provide a seamless backdrop for creating lasting memories while enjoying the natural beauty of the Central Coast. The estate's generous footprint offers flexibility for extended family, guests, personal collections, creative pursuits, or executive work-from-home lifestyles. Whether envisioned as a private sanctuary, an entertainer's showcase, or a generational asset to be enjoyed for decades to come, the possibilities are as inspiring as the setting itself. Conveniently located within reach of Silicon Valley's innovation centers while offering a world apart from the demands of everyday life, this is a property that combines luxury, privacy, and lifestyle in a truly exceptional way.

535 Highland AVE, Santa Cruz

Listed by Tim Allen, 831-214-1990 from Coldwell Banker Realty
(If provided) CoList: from

$6,950,000
4 Beds 3 Baths ML82033309 MLS
Along the coveted stretch of Opal Cliff Drive, this one-of-a-kind property offers one of the most desirable waterfront locations in Santa Cruz County featuring a large parcel, approximately 127 linear ft of ocean frontage, & sweeping panoramic ocean views. Perfectly positioned between Pleasure Point & Capitola Village, it overlooks world-class surf spots including The Hook, Sharks Cove, & Privates, & is just minutes to beaches, shops, & coastal dining. This custom-built, one-owner home maximizes its oceanside setting with breathtaking views from nearly every room. Set back from the street on almost half an acre, the property welcomes you with a spacious parking courtyard, lush lawn, & inviting entryway. Inside, enjoy vaulted ceilings, cozy fireplaces, & walls of glass that open to an ocean-view deck, seamlessly blending indoor & outdoor living. The main level includes the primary suite, kitchen, living areas, & a den/optional 4th bedroom, offering flexibility for single-level living. Upstairs are two bedrooms, a shared bath, & a deck with coastline views. Originally designed as a three-car garage, it now features a two-car setup with workbench & built-in storage. Recent improvements include a professional soil stabilization system along the cliffside & refreshed landscaping.

4250 Opal Cliff DR, Santa Cruz

Listed by Lyng-Vidrine Team, 831-345-0503 from David Lyng Real Estate
(If provided) CoList: Donna Hooper Danza from David Lyng Real Estate

$589,000
ML82031602 MLS
Perched above the city in one of Santa Cruzs most desirable settings, 760 Escalona Drive presents a truly rare opportunity to own an expansive ocean-view lot with breathtaking coastal vistas by day and glittering city lights by night. This exceptional property offers the perfect canvas to custom design and build the home of your dreams, thoughtfully positioned to capture ocean views, natural light, and the relaxed coastal lifestyle Santa Cruz is famous for. Ideally located with easy access to world-class surf breaks, scenic hiking and biking trails, UCSC, beaches, and vibrant downtown amenities, this lot combines tranquility with everyday convenience. Whether you envision a modern coastal retreat or a timeless Santa Cruz residence, the possibilities here are extraordinary. The seller has pre-development information available to interested buyers, providing valuable insight into the development potential of the property. Ocean-view lots within the City of Santa Cruz are vanishingly rare, making this a once-in-a-lifetime opportunity to create a legacy property in an iconic coastal community. Don't miss your chance to secure one of the last remaining view lots of its kind.

760 Escalona DR, Santa Cruz

Listed by Daniel Oster, 831-252-5000 from Coldwell Banker Realty
(If provided) CoList: from

$575,000
ML82027091 MLS
Exclusive Resort Living: Lot with Home Plans! Start with architectural plans for a magnificent 4,881-square-foot luxury home, giving you a powerful head start on creating your perfect estate. Water service is in, and the site features established infrastructure with paved road access. Your future neighborhood offers immediate, optional access to the amenities of the Chaminade Resort & Spa (membership not included), all just steps from your future doorstep: Fine Dining, state-of-the-art fitness center, multiple tennis courts, spa services multiple and swimming pools. Imagine waking up to breathtaking, multi-faceted views that define the Santa Cruz experience. Enjoy stunning panoramas encompassing City Lights, tranquil Forest/Woods, lush Garden/Greenbelt, and rolling Mountains. This prime location offers immediate access to the best of Santa Cruz, just minutes from iconic attractions like Steamer Lane and the Santa Cruz Wharf. Central California Convenience: Achieve the perfect balance of serene, luxury living and major urban access: a convenient 30-mile drive to Silicon Valley, and about an hour's scenic journey to the cultural hubs of San Francisco, Monterey, and Carmel-By-The-Sea. Don't just build a house; build a legacy. Secure your spot in this exclusive community today.

00 Lupine LN, Santa Cruz

Listed by Paul Burrowes, 408-497-3989 from David Lyng Real Estate
(If provided) CoList: from

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