116 properties for sale in Guadalupe city

This property is part of the Kennedy Estate. Two adjoining parcels (APN 098 011 22 and 098 011 23) totaling 44.61 acres in a peaceful, private mountain setting. These parcels include a small home, an additional structure suitable for storage, and an established orchard, offering a blend of existing improvements and expansive natural landscape. The property features open space, mature trees, and long-term land holding appeal. Buyers should verify zoning, utilities, access, septic, water sources, and all permitted uses with Santa Cruz County. A substantial acreage offering in a desirable rural location

Set on one of the largest corner lots in one of Los Gatos’ most coveted neighborhoods, this exceptional property enjoys a premier location in the desirable sweet spot between Lark Avenue, Vasona Park, and Hwy 17. Nestled just behind the Vasona Dam, a natural hillside shields the home from freeway noise, creating a peaceful environment filled with the sounds of songbirds and the seasonal migration of wild geese. A short stroll from Vasona Lake—yet comfortably removed from weekend activity—the home offers a rare blend of tranquility and convenience. Enjoy breathtaking sunsets over the water, or take a scenic 15‑minute bike ride along the Los Gatos Creek Trail to the charming shops, restaurants, and cafés of Downtown Los Gatos. A majestic redwood—one of the few in the neighborhood—anchors the property with timeless beauty, providing welcome shade throughout the summer months. Inside, soaring vaulted ceilings and abundant natural light enhance the spacious, open living areas, creating an i

Welcome to 200 Carlester Drive, a fully renovated three bedroom, two bath home where timeless charm meets modern comfort. With 1,296 square feet of thoughtfully redesigned living space, this residence offers a warm, inviting atmosphere paired with high‑quality updates throughout. The heart of the home is the beautifully refreshed kitchen, featuring classic shaker cabinetry and quartz countertops that bring both style and practicality. New flooring and updated lighting enhance every room, while both bathrooms have been transformed with new tile, modern vanities, and fresh fixtures for a clean, spa‑like feel. Behind the scenes, the home has been extensively upgraded with all‑new plumbing, a new AC system, new exterior paint, and new exterior lighting — ensuring comfort and peace of mind for years to come. Every detail has been carefully considered to create a cohesive, move‑in‑ready home. Located in Los Gatos and served by Los Gatos schools, enjoy easy access to parks, downtown dining an

Offered through the Kennedy Estate. Set on 21.37 acres in the Los Gatos mountains, this property features a 2,559 square foot home built in 1952 with five bedrooms and three and a half bathrooms. The residence has been held by the Kennedy family for many years and remains in original condition, offering a rare opportunity for buyers seeking a large acreage setting with long established improvements. The land includes natural terrain, mature trees, and areas used for pear cultivation. A unique chance to own a substantial mountain property with privacy and space. Buyers are advised to verify all property details, including utilities, access, zoning, permits, square footage, with the appropriate county agencies

Offered by the Kennedy Estate as part of a multiparcel disposition, this 3,378 sq ft residence along with APN 562-01-038 will be sold together making approximately 79 total acres, presenting a rare large acreage opportunity in the Los Gatos mountains. Built in 1925, the home features five bedrooms, three bathrooms, an attached garage, and a detached garage. The land highlights the properties long history in the region, with natural terrain, established improvements, and a mature apple orchard that has been part of the landscape for many years. The location reflects a largescale ownership footprint within the Loma Prieta community, offering notable acreage, enduring character, and a setting that showcases the scale and presence of this mountain property

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Wonderful downtown Los Gatos location in the popular Loma Alta/Johnson neighborhood! This beautiful, almost 1/3-acre parcel features an existing historic home on a spacious lot just steps away from top Los Gatos schools, shops and dining. The expansive, open floor plan enjoys large picture windows overlooking the front as well as the tree studded ravine at the rear of the property. Update and expand while maintaining the historic nature of the exterior front facade. A unique opportunity to own a piece of history in a very desirable location in downtown Los Gatos!

Welcome to this exceptional home in the highly desirable Las Cumbres community, where comfort, space, and natural beauty come together. A stunning entryway with vaulted ceilings and a grand staircase creates a warm first impression. The open floor plan features wide hallways and seamless flow between rooms, perfect for everyday living and entertaining. The remodeled kitchen is the heart of the home, offering new appliances, a large island, ample prep space, and an eating area with charming alcove windows. It opens to a spacious family room with a cozy wood-burning stove. A formal dining room connects to the kitchen and living areas, while the elegant living room features vaulted ceilings and its own wood-burning stove. The main level includes a versatile bedroom or office and a bonus playroom. Upstairs, the primary suite offers a vaulted ceiling, walk-in closet, large bathroom, and private deck. Two additional bedrooms include alcove spaces, with new flooring throughout the second floo

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

An extraordinary architectural estate set on 86 +/- acres in the Santa Cruz Mountains, just minutes from downtown Los Gatos. Designed to capture sweeping panoramic views of Monterey Bay, the home features soaring ceilings, expansive walls of glass, and refined sight-lines that seamlessly integrate the indoors with the surrounding landscape. Rich hardwood floors and curated finishes define the interiors, offering five spacious bedrooms, three full baths, and two half baths. The primary suite is a private retreat with a fireplace, spa-caliber bath, and a generous walk-in closet. Built with exceptional craftsmanship and uncompromising attention to detail, this meticulously maintained home reflects enduring quality throughout. The grounds offer sculpted landscapes, rose gardens, open meadows, and private trails, complete with recreational amenities, creating a rare balance of luxury, scale, and mountain serenity. Served by award-winning Los Gatos Schools

Set within a private enclave of just nine homes in the prestigious Los Gatos hills, this Mediterranean-style residence is surrounded by lush greenery & sweeping Santa Cruz Mountain views. Designed for indoor-outdoor living & a connection to nature, the home feels remarkably private yet is minutes from downtown Los Gatos, top-rated schools & major commute routes. Vibrant landscaping creates a colorful approach. Beyond a black iron gate, a travertine patio unfolds beneath graceful arches & columns, with mature fruit trees, flowering plants & sculptural greenery complementing the architecture. An alder wood front door opens to a foyer with travertine floors, while engineered hardwood continues through the main living areas. The living room features a gas fireplace framed in cast stone, with picture windows filling the room with natural light & capturing views across the front grounds. The formal dining room is inviting for gatherings, with an elegant chandelier & built-in buffet with alde

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Is a mountain escape calling you? This cottage hideaway is a must see. Away from valley noise, down a beautiful forest road and conveniently just minutes from the highly acclaimed Summit Grocery and Friday Farmer's Market! Do you want beautiful flat space, privacy, sun and shade, outdoor enjoyment patios and an easy maintenance yard? This is it. This is the perfect property to enjoy guests with its abundance of parking, and indoor-outdoor living across the whole ground level. Or enjoy your solitude! Unwind taking in nature and views from the back balcony, or inside the home cozied up to the warm, soft glow of the pellet stove. Two upstairs bedrooms feature views into the treetops like you're in a treehouse. Ground floor has the full bathroom with great natural light, and a living room with sliding glass doors opening onto the back balcony. A breakfast bar opens to a brick laid patio and backyard. Light, bright kitchen perfect to grow herbs, and you can prep meals on a gas stove. Window

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Welcome to an exquisite Mediterranean estate nestled in the foothills of Los Gatos at 16840 Cypress Way. Located at the bottom of Cypress Way, this gated property offers privacy and dramatic views with easy access to the vibrant downtown. This luxurious residence boasts breathtaking vistas of the valley, offering a stunning 5,844sf± of refined living space. Designed for both elegance and comfort, the home features 5 sumptuous bedrooms, each with private ensuite bath, including a convenient main level suite for multi-generational living. The expansive main level is thoughtfully arranged, encompassing a formal living room, spacious office, kitchen/great room, and a formal dining room that opens onto a voluminous covered patio. Perfect for entertainment, this outdoor space overlooks the verdant gardens and enchanting water features. The property spans over 2.03± acres. This gated sanctuary is complemented by a 800sf± estate entertainment retreat, jacuzzi pavilion, and sunning terrace, inv

Located in the heart of Silicon Valley, this extraordinary Monte Sereno estate represents a rare fusion of grand scale, refined elegance, & unparalleled convenience. Recently transformed through a $10M+ comprehensive renovation, the residence evokes the timeless grandeur of a stately European estate. Set on 1.37 pristine, flat acres, it offers approximately 17,000 square feet of impeccably curated living & storage space beneath a brand-new $1M Tesla solar roof. The main residence features ten bedrooms & eight bathrooms, complemented by a private guest house & separate apartment. Resort-caliber amenities abound, including a ten-car garage, underground shooting range, indoor basketball & racquetball court, USTA-regulation tennis court, resort-style lap pool & spa, expansive great room, home theater, private elevator, two formal libraries, and a gym/nursery. Taken down to the studs, every detail has been reimagined w/ uncompromising quality new Jeld-Wen windows & doors, all-new appliances

Mid-Century Modern Los Gatos home with excellent Los Gatos Schools. Nestled on a quiet street in a gorgeous natural setting, this remodeled home has been impeccably maintained. The best of open concept living, there is seamless indoor-outdoor entertaining. Multiple areas for gatherings: the Chef's gourmet kitchen opens to the great room, dining room, breakfast bar, sunny nook, warm and inviting living room along with your choice of decks. Stunning volume ceilings soaring with sunshine through abundant windows each having views to the beautiful outdoors. At the heart of the home is the Chef's kitchen featuring modern cabinets, stainless appliances, pantry and sleek slab counters with plenty of prep space. The spacious primary features a large walk-in closet and ensuite bathroom. The remodeled hall bath features contemporary tile, modern vanity and a designer shower. Additional features: private quiet location, gleaming wood floors, most of the home is on one level, interior laundry, ext

Escape to the tranquility of the Santa Cruz Mountains without giving up proximity to town. This move in ready Redwood Estates retreat was rebuilt down to the studs in 2015 and blends modern comfort with the natural beauty of its redwood surroundings. This home offers light-filled spaces designed for today's lifestyle. An open-concept floor plan creates seamless flow between the living area and well-appointed kitchen, featuring granite countertops, breakfast bar seating, and abundant cabinetry. Wood window framing, crown molding, and travertine flooring add warmth and quality throughout. The floor plan offers space well suited for a home office, creative studio, or guest accommodations. Privacy surrounds the property, while ample parking provides a valuable advantage. Approx.10 min. from Downtown Los Gatos, enjoy convenient access to shopping, dining, recreation, and major Silicon Valley employment centers while maintaining the serenity and beauty of mountain living. Those seeking a ful

Experience the pinnacle of gated estate living with breathtaking views stretching from Lexington Reservoir & Mt Umunhum to the lights of downtown San Jose. Just minutes from Los Gatos, this sophisticated residence combines privacy, luxury, & an exceptional setting. The refreshed interior features new flooring, fresh paint, & an open floor plan designed for effortless living & entertaining. The main level offers an office & guest suite with a full bath. At the heart of the home is the chefs kitchen with granite countertops, a gas cooktop, & abundant cabinetry, flowing seamlessly into a light-filled living area where walls of glass frame the views. Upstairs, the versatile floor plan includes two additional bedrooms & a private gym. The luxurious primary retreat is a sanctuary of comfort, featuring a spa-inspired bath & private viewing deck. Outdoor living is equally impressive, with an expansive veranda & outdoor kitchen, creating the perfect setting for entertaining. The property also f

Nestled upon approximately 1.2 acres of manicured level grounds one-quarter mile from downtown Los Gatos, this single-story estate by Maggetti Construction and architect Gary Kohlsaat blends Old-World architecture with resort-caliber living. A dramatic gated entrance with electric security gate leads to a custom door of antique beveled and leaded glass, opening onto a natural stone foyer with mosaic medallion and dome. Formal living and dining rooms feature vaulted ceilings, natural stone fireplaces, walnut floors, Murano crystal chandelier, and French doors to the park-like rear grounds. The epicurean chefs kitchen offers custom walnut cabinetry, mother-of-pearl quartz, dual Sub-Zero refrigerators, Wolf range, stone island seating five, and butlers pantry with additional Sub-Zero. The grand family room rises to fourteen-foot vaulted ceilings with floor-to-ceiling fireplace and walnut bookshelves, while a private library or media suite provides walnut shelving and gas fireplace. The pr

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

GATED COMMUNITY | VIEWS LEAVE PEOPLE SPEECHLESS | FOOD DELIVERY, AMAZON Etc. FRIENDLY | FORTIFIED W/ SOLAR & BACK UP POWER THE RESIDENCE, THE LAND | The perfect retreat home, Upper Ellen Rd. is for people who like to be social with their neighbors, or, enjoy the serene privacy above the tree tops. Imagine sweeping views from most of your living spaces, being above the clouds, and sunsets that make you stop whatever it is you were doing. If you must, working from home is easy with 2 separate offices plus great 'net options. Simplicity with the Primary suite & 1 bdrm on the ground level. Open floor plan complements the sweeping views, and the wood paneled Family Room adds to the beauty and includes a hide-away TV space. This would be perfect for an elegant dining room, or Library! Outdoors the usable space beckons! A fenced backyard has easy maintenance fake-grass, you can exercise in the resistance pool, or relax in the hot tub looking out to the views. Plus, and additional, huge, sunse

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Located in a sought-after Los Gatos neighborhood, 38 Alpine Avenue is an expansive Mediterranean-style villa w/ grand architecture, impressive scale & curated finishes. Enjoy this iconic location, just a 5 minute stroll to the hustle & bustle of downtown LG dining and shopping & nearby hiking & biking trails. Lush landscaping surrounds the front grounds where manicured hedges, variegated shrubbery & gorgeous blooms frame this handsome estate on an expansive lot of over half an acre. Overlooking the front landscape, the handsome front entry is accented by commanding columns. Open the iron double entry doors to the exceptional circular foyer w/ 12 ft. ceilings. The sunlit interior enjoys beautiful views through the many picture windows & French doors. Gorgeous Brazilian cherry hardwood floors flow through the expansive living spaces. A large cast limestone fireplace anchors the formal living room flanked by picture windows. French doors open to a private front patio surrounded by tall he

This beautiful approximately 2,300 square foot home sits on a peaceful 9.9 acre parcel in the Santa Cruz Mountains, offering privacy, open space, and stunning natural surroundings while remaining conveniently close to town. The home features three bedrooms, two full bathrooms, and one-half bath. The main level includes living and entertaining. The house has two separate entrances: a main front entrance and a practical mudroom entry, which is especially convenient throughout the seasons and ideal for families. On the second level, you are welcomed by a spacious office with large windows overlooking a beautiful green meadow, complete with built-in library, creating an inspiring and light-filled workplace. The bedrooms are arranged in a distinctive split-level layout, each reached by short staircases that create privacy and architectural character. Exceptional outdoor living with two expansive decks (approximately 1,000 square feet and 400 square feet) ideal for entertaining or relaxing i

Set within the desirable Villa de Los Gatos community, this beautifully maintained townhouse offers generous living spaces, excellent community amenities, and a highly sought-after Los Gatos location. The inviting interior opens to a spacious living room with rich hardwood floors extending throughout the main living areas. Just beyond, the kitchen features abundant cabinetry, quartz countertops, stainless steel appliances, and a garden window overlooking the backyard. The dining area, complete with a built-in buffet, provides an ideal setting for meals with family and friends. A glass door opens to a private, sun-filled patio, creating a seamless indoor-outdoor connection. A convenient powder bath and laundry area complete the main level. Upstairs, three freshly-painted bedrooms offer a bright and comfortable retreat. The primary suite features generous closet space and an en-suite bathroom, while two additional bedrooms share a well-appointed hall bath. The private rear patio provides

Exceptional Platinum Triangle Location off Glen Una Dr central to Saratoga & Los Gatos! County address means rare opportunity to expand the existing charming Mid Century modern house or build your dream estate! Invest in South Bay's finest neighborhood! Flat usable land, majestic trees, peaceful mountain vistas & end of cul-de-sac location make this a very desirable place to live. Quiet and exceptionally private! Clean lines, floor-to ceiling windows and doors create an inviting living space drenched in natural light, allowing for harmonious indoor and outdoor living. In contrast, the wood paneling brings a natural warmth and texture. Home embraces the architectural idea of simplicity and integration with nature. in ground pool and spa ready for entertaining. Seasonal creek provides uncommon ambiance. Detached 1bd, 1ba ADU offers exceptional flexibility w/ kitchen, laundry & private deck. Perfect for guests, au pair, or a rental. This wonderful property is just minutes from the vibrant

Welcome home to Lora Manor, a small complex of neighbors located near La Rinconada Country Club with convenient access to Bay Club Courtside, Netflix and highways 85 and 17. This well proportioned updated ground floor home offers a spacious living room, remodeled kitchen and bathroom, two large bedrooms and a private patio. Recessed lighting and modern wide plank flooring can be found throughout the home as well as mirrored closet doors and coved ceilings. The remodeled kitchen is equipped with attractive granite countertops and stainless steel appliances. The updated bathroom features a large vanity, newly refinished shower over tub and attractive wood tile floors. There is a convenient community laundry with multiple machines and a folding table as well as a community room and BBQ area available to residents. Excellent schools, parks and shopping are located nearby and a short drive brings you to eclectic downtown Los Gatos with world class restaurants, shopping and community events

Exceptional opportunity in academically acclaimed Los Gatos Schools to complete plans submitted for future remodel/expansion of existing home to 2318 sq ft including 443 square foot Accessory Dwelling Unit. Expanded home would feature four bedrooms plus office and four and a half bathrooms. Alternatively, may be ideal for a remodel without expansion. The existing house is on a level 7,700 sq ft lot featuring expansive front and back yards, mature trees, patio and a multitude of possibilities for outdoor fun and entertainment. Recently painted and carpeted, the home features a bright living/great room with fireplace, formal dining area, and an eat-in kitchen with abundant storage and newer butcher-block kitchen countertops. Both sunny bedrooms have full-wall closets. Hall bathroom includes shower over tub. Additional spaces include a fully enclosed sunroom with a half bathroom and an oversized two-car garage with new garage door and workbench perfect for hobbies or storage. Ideal locati