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$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

$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

$2,950,000
3 Beds 3 Baths ML82027765 MLS
Unobstructed views of the Pacific Ocean and Monterey Bay from this exquisite home located in the desirable Westlake community. No expense was spared when completely remodeled in 1998. Tile, granite, marble and only the best in fixtures throughout. Main level of the home consists of the living room with fireplace, family room, dining area, kitchen, primary bedroom with bathroom, second bedroom, second bathroom and laundry room. An enchanting staircase leads downstairs to an additional living room with fireplace, bar area, third bedroom and bathroom. Large, expansive decks off both levels with spectacular views along with your own putting green. Too many features to list. See for yourself.

902 Laurent ST, Santa Cruz

Listed by Russell Gross, 831-464-4700 from Russell E. Gross Real Estate
(If provided) CoList: from

$2,875,000
3 Beds 3 Baths ML82052339 MLS
Exceptional remodeled Tudor-style home on Santa Cruz's coveted Upper Westside with breathtaking panoramic ocean views. This beautifully updated residence offers 3 bedrooms, 3 bathrooms, and 2,614 sq. ft. of living space, plus an attached 3 car garage, and a 374 sq. ft. bonus room and a full bath. Situated on a 9,017 sq. ft. lot, the property features terraced gardens, a private ocean-view patio, and inviting outdoor living spaces just minutes from West Cliff Drive, beaches, New Leaf Market, and popular restaurants. A stained-glass archway welcomes you into a private courtyard with mature landscaping. Inside, hardwood floors, a gas fireplace, and picture windows create a warm and inviting atmosphere. The chef's kitchen features a Viking 5-burner cooktop, GE double ovens, quartz counters, and Dutch door to the patio. Additional amenities include owned solar, smart-home features, a luxurious primary suite with ocean-view balcony, finished attic office space, and a versatile bonus room ideal for guests, multigenerational living, or a home office. Rare opportunity to own a character-rich Tudor with charm & ocean views in one of Santa Cruz's most coveted neighborhoods!

1418 Escalona DR, Santa Cruz

Listed by Lauren Spencer, 831-818-3723 from Coldwell Banker Realty
(If provided) CoList: Georgia Phillips from Coldwell Banker Realty

$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

$2,250,000
3 Beds 4 Baths ML82046761 MLS
Positioned just off West Cliff Drive and with a fantastic new price,1010 Pelton Avenue offers a 10/10 location with a rare combination of ocean views, privacy, and untapped potential. Step out your front door and you'll be on West Cliff taking in the fresh ocean air, in an approximate minute while still enjoying a more private setting than some front-row coastal locations. Inside and upstairs the open ceiling soars allowing Sunsets galore to fill the home and become part of everyday life. Multiple rooms have ocean views and the energy is one that feels both peaceful and connected to the coastline. So if your days involve surfing, sailing, dancing, reading, biking along the stunning coastal landscapes or just listening to the soothing sound of the surf you truly can have it all. This home and location offer the timeless rhythm of wind, waves, and ocean ebbs and flows; all part of the exceptional Santa Cruz coastal lifestyle. Lovingly lived in by a local family for decades with a detached additional rustic structure with a full bath and a loft large enough for a king-size bed adds flexibility and further potential to the property. Ready to be reimagined, this is a rare chance to own this special property in one of Santa Cruz's most sought-after coastal neighborhoods.

1010 Pelton AVE, Santa Cruz

Listed by Stacey Mitchell, 831-234-2356 from Bailey Properties
(If provided) CoList: from

$1,999,000
2 Beds 2 Baths ML82054301 MLS
Discover the endless possibilities of this Lower Westside gem, located just two houses away from the ocean! This charming 2-bedroom, 2-bath single-story home offers the perfect canvas to build or reimagine your dream home, featuring ocean views from the living room and private back yard. Situated in one of Santa Cruz's most coveted neighborhoods, enjoy a prime location just moments from Westcliff Drive, the bike path, and amazing views of the Monterey Bay. Embrace the convenience of being moments away from the popular Swift Street Courtyard, offering easy access to local hotspots like Cat and Cloud, Humble Sea, New Leaf Market, Bantam, and an array of wineries and dining attractions. With mature landscaping in the front and convenient alley access in the back, this home combines classic appeal with incredible future potential. Don't miss this opportunity - A MUST SEE!!

123 Merced AVE, Santa Cruz

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

$949,000
ML82051423 MLS
The Circles are the heartbeat of Westside Santa Cruz. Unique concentric streets radiate out from Errett Circle like a bullseye creating an uncommon and beautifully laid plan that has shaped the Westside's identity for almost 140 years. For the first time the center circle has opened up to residential development. The community of homes planned is designed for gathering.The Circles sit between Mission St & W Cliff Dr. With a Walk Score of 82 and Bike Score of 100~you wont need to drive to access the very best~located just a few blocks awaythe Pacific Ocean & Monterey Bay, Lighthouse Field & Steamer Lane, theWharf & Boardwalk, Mitchells Cove w/incredible sunset views over world class surf breaks and Natural Bridges State Beach. Positioned at 10,11 & 12 on the clock, these are sought after lots that face West Cliff Dr w/ocean views from a 2nd story perch. 5K sf lots are fully cleared and ready to submit plans for permits. Theres a community centerpiece/gathering space that features a grassy lawn, fire pits, a bocce court, raised flower beds, picnic areas & community gardens. This is a rare chance to design-build your dream home and to get in on the ground floor and seize an early advantage to nurture a unique community in one of the most coveted and fiercely loved neighborhoods.

111-08 Errett CIR, Santa Cruz

Listed by Daniel Alvarez, 831-818-4181 from David Lyng Real Estate
(If provided) CoList: from

$949,000
ML82051421 MLS
The Circles are the heartbeat of Westside Santa Cruz. Unique concentric streets radiate out from Errett Circle like a bullseye creating an uncommon and beautifully laid plan that has shaped the Westside's identity for almost 140 years. For the first time the center circle has opened up to residential development. The community of homes planned is designed for gathering.The Circles sit between Mission St & W Cliff Dr. With a Walk Score of 82 and Bike Score of 100~you wont need to drive to access the very best~located just a few blocks awaythe Pacific Ocean & Monterey Bay, Lighthouse Field & Steamer Lane, theWharf & Boardwalk, Mitchells Cove w/incredible sunset views over world class surf breaks and Natural Bridges State Beach. Positioned at 10,11 & 12 on the clock, these are sought after lots that face West Cliff Dr w/ocean views from a 2nd story perch. 5K sf lots are fully cleared and ready to submit plans for permits. Theres a community centerpiece/gathering space that features a grassy lawn, fire pits, a bocce court, raised flower beds, picnic areas & community gardens. This is a rare chance to design-build your dream home and to get in on the ground floor and seize an early advantage to nurture a unique community in one of the most coveted and fiercely loved neighborhoods.

111-10 Errett CIR, Santa Cruz

Listed by Daniel Alvarez, 831-818-4181 from David Lyng Real Estate
(If provided) CoList: from

$860,000
ML82034329 MLS
Exceptional opportunity to build your custom dream home on this 7,928 square foot vacant lot, ideally located on a quiet cul-de-sac in Santa Cruz. Tucked away in a peaceful setting, this property offers privacy and the potential for city and ocean views with a thoughtfully designed two-story or elevated floor plan (subject to city approval). Adding to the appeal, the adjacent 7,579 square foot lot is also available for sale creating a rare chance to secure one or both parcels. Purchase both for a combined 15,507 square feet and expand your vision with additional space for a larger residence, guest house or enhanced outdoor living areas (subject to city approval). Conveniently located just minutes from beaches, downtown Santa Cruz, UCSC, and schools, this location blends coastal lifestyle with everyday convenience. Opportunities like this side-by-side lots in a desirable cul-de-sac setting are increasingly rare. Bring your builder and imagination to create something truly special in one of Santa Cruz sought-after neighborhoods.

112 Hillcrest TER, Santa Cruz

Listed by Ronald Esche, 831-818-1323 from RAE Properties
(If provided) CoList: from

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