Hillsborough CA Real Estate & Homes for Sale

Privately tucked away on a bucolic cul-de-sac in a rarely available enclave in upper Hillsborough, this gracious transitional-style residence captures the magic of true indoor-outdoor living. A bougainvillea archway precedes the front porch where double doors open to grand-sized rooms showcasing walls of windows with tranquil views and French doors opening to decks, courtyards and landscaped grounds. Premium hardwood, stone and new carpeting sweep through the three-level floorplan with exquisite custom details, sophisticated lighting, four fireplaces and outdoor access at every turn. From the foyer and marble-lined formal living and dining room, to the chefs kitchen and family room with wrap-around deck, and lower-level rec room with living, dining, board and game table areas, entertaining is a delight. The alluring primary suite occupies the entire upper level of the home, 4 bedrooms are on the main level and 1 bedroom and office are on the lower level. Refined living at its finest.

Newly Remodeled | Open Floor Plan | Eat-In Kitchen with 9-Foot Island | Thermador Chef Grade Appliances | Zephyr Hood and Wine Refrigerator | Sharp Microwave Drawer | Great Room with Grand Ceiling Height | Four Bedrooms Including Two En Suites | Three New Spa-Like Bathrooms | Laundry Room with Electrolux Appliances | Two-Car Attached Garage with New Cement Slab | Expansive Driveway | Grand Perimeter Trees | New Sprawling Turf Area | Newly Fenced Yard and Landscaping | Award-Winning Schools

ONE OF THE BEST BAY VIEWS IN ALL OF HILLSBOROUGH! AN ABSOLUTE TREASURE & LANKMARK PROPERTY! These views MUST BE SEEN IN PERSON to truly admire, we mean it! Stunning unobstructed panoramic 270-degree+/- views as far as the eye can see, to the blue waters of the SF Bay & beyond! Enjoy breathtakingly vibrant sunsets & cool relaxing nights under the stars. Privacy & luxury are other hallmarks. You can go ahead & move right into this TURN-KEY RENOVATED home or use the preliminary architect drawn renderings of a new DREAM HOME. The move-in ready home offers scenic views from almost every room in the house, plus an open floor plan & premium renovations. The new dream house will sit in a new location way back, w/ a HUGE flat yard on the front & side. You get everything you could want, long driveway, total privacy, immaculate billion-dollar views, huge backyard, exclusive neighborhood & a home sure to impress everyone. Photos: https://greenbanker.com/255pinehill/ *Tenant occupied dont drive in.

CURATED CASTLE AT LEGENDARY CHATEAUX LOCATION! Built New in 2001, discover Modern-Era Luxury with Charismatic Grandeur. Heralded as the height of Hillsborough prestige for over 100 years, this Pullman Road location hosts ultimate luxury as your castle in a land of Chateaux. Just around the corner from the historic Carolands Chateau, 610 Pullman occupies the perfect spot in the neighborhood of minimal through-traffic and flat streets. The 600 block has emerged as its own Mansion Row with many regal estates gazing out toward the Bay. Inspired by the best of European elegance, this home was built new in 2001, crafted in French Country style spanning 5,740 sq. ft. of living on three levels. *5 bedrooms, 5.5 bathrooms, CEO Library, plus lower level Rec Room ideal for Media, Gym, or even a 6th bedroom/Guest hideaway. *Awesome high ceilings *Smooth Modern Floorplan and Main Level Suite that acts as a Second Primary* Resort-style Pool/Spa and Open Lawns.

THE BEST DEAL IN HILLSBOROUGH TO BEAT INFLATION!!! THE LOWEST $/SQFT FOR A HOME WITH FLAT LAND! This luxurious property is located on a HUGE MOSTLY FLAT 0.51-acre corner lot w/ USABLE LAND. Sprawling front & back green lawns, just waiting for an ADU. Youll be hard pressed to find a better deal. Wide-open, spacious living quarters are beaming w/ lots of natural light. This home has unlimited potential & an ideal floorplan. This homes perfect for multi-generational living or growing families. The main level features a formal living room, dining room, eat-in kitchen, family room & 3 bedrooms. The lower level offers a great room, en-suite bedroom, game room & access to the back. The backyard has a large lawn, mature trees, a pool & a deck w/ a hot tub spa; perfect for the whole family. Picturesque Carolands has quick access to Hwy 280, Downtown Burlingame & highly coveted schools. This move-in ready home presents an opportunity for create your dream home! Dont wait until its too late!

CHATEAU NOUVEAU...nearly 9,000 feet of Contemporary Zeitgeist. Discover this Residential Work of Art at the very heart of Lower South Hillsborough. Architecture that designers dream of with towering ceilings, open flowing spaces, and bold, exciting statements in the modern vernacular. Imagine crafting a re-invented color palette, your minimalist interior design vision, or eclectic interpretation on a grand scale. 6 beds, 6.5 baths, Office, Gym, Screening Room, Recreation Room, Indoor/Outdoor Loggia, 4-car side-by-side garage, plus gated 2-car carport. This pancake-flat lot of .78 Acre is 100% usable and welcomes your new ADU/Pool House Ideas. Just steps to South School and the Hillsborough Racquet Club, this is a special location filled with history, prestige, and utmost convenience. *Seller may entertain Seller Financing to Qualified Buyers*

Spacious sun-drenched living quarters & elegant amenities converge to create the perfect quintessential Hillsborough home. This corner-lot estate is emanating w/ thoughtful design choices & functional appointments. Tasteful hardwood flows throughout this open floor plan, complemented by crown molding, tall ceilings, recessed lighting, & wide windows. The myriad of windows opens this home up to lots of natural light creating an open airy ambiance. The floorplan is ideal for routine living & hosting. The stylishly appointed kitchen is equipped w/ all high-end appliances. The dining room & living room connect by way of open concept, perfect for entertaining. The family room has a custom bar, half bath, & access to the backyard. All the bedrooms are a welcome retreat after a long day. The pristine bathrooms feature double vanities. The cherry on top is the backyard with a sparkling pool, big lawn, & pickleball / multi-use sports court. Minutes from Dwntwn San Mateo & sought-after schools.

Elegance and quality craftsmanship radiate throughout this thoughtfully remodeled ranch style home sighted on a level 23,244 sq. foot lot in the highly coveted Country Club neighborhood. Paved, circular driveway with 3 car garage. The idyllic open floor plan includes 5 bedrooms, 4 bathrooms with a spacious and voluminous Primary Suite. The redesigned public areas are open and bright, and the newly remodeled gourmet kitchen is fitted with top of the line Hestan appliances, 9 foot island with waterfall edge and seating for 4 is ready to please when entertaining family and friends. Stepping outside you will revel at the resort like professionally landscaped grounds. The masterful use of hard surfaces seamlessly wrapping around the sparkling pool, fireplace with pergola, bocce ball court, she shed/artist studio, outdoor kitchen equipped with top-of-the-line Viking Grill & appliances including a Lynx pizza oven all designed to provide the ultimate in entertaining spaces & outdoor enjoyment.

Situated on a private side street, this grand estate sits on a majestic 2-acres with jaw-dropping panoramic bay views, some of the best in all of Hillsborough. Exquisite architectural detailing and finishes throughout, including inlaid parquet walnut floors, hand carved fireplaces, and walls of glass framing iconic bay views and landscaping. The main level includes a stunning office, billiard hall, and the "Morocco Room" lounge. Upstairs, the large master suite enjoys equally stunning views of the bay, in addition to a luxury spa bath and formal sitting room. A separate in-law suite and wine cellar with tasting room are located on the lower level of the residence. Equally impressive are the surrounding grounds, fully landscaped with grand-scale trees, expanses of manicured lawn, and an elevated terrace overlooking the views and swimming pool. All of this just minutes from shopping, dining, golfing, parks, and top rated Hillsborough schools. (Square Footage Per County Records: 8,629)

One of the finest properties to ever hit the market... a spectacular 2.24 acre trophy estate in the heart of Hillsborough. Classic architectural styling meets modern sophistication at this French country manor designed by renowned local architect Farro Essalat with approximately ~11,500 Square Feet of living space between the main house and guest house. Tucked away at the end of a setback driveway for the utmost privacy, the home's natural illumination uplifts grand interior spaces that imbue a sense of scale and panache, with exquisite period details such as beautifully stained oak hardwood floors and dramatic exposed-beam ceilings. Pool, full size tennis court, a three-level guest house, underground wine cellar, and breathtaking bay views, this property has it all. Hillsborough has exceptional access to boutique shopping, fine restaurants and Vista Park lies just up the road - a year-round children's playground with outdoor recreation. (Square Footage Per County Records: 8,065)

Timeless character & architecture awaits w/ an impressive 7,600 SqFt of living space. Taking cues from the neighborhood, this home offers total privacy & lots of verdant foliage. Quality craftsmanship takes center stage in this one-of-a-kind tutor abode. The wide-open & airy ambiance this floor plan offers is the perfect platform for both entertaining on a grand scale & everyday living. High ceilings, hardwood, crown molding, custom fireplaces, a grand staircase, tall windows, & intricate design elements can be found throughout. Expansive living quarters on multiple levels & two separate kitchens make way for plenty of room for you & your family/guests. Aspects include a fully equipped kitchen, huge formal dining room, custom library, grand office, a master suite fit for royalty, 2 decks w/ BREATHTAKING PANORAMIC SF BAYVIEWS, two living rooms & MORE! Private backyard oasis w/ a sparkling pool & lush lawn. Walking distance to Downtown Burlingame / North Elementary & Crocker Middle.

REMODELED THROUGHOUT MOST, COMPLETED IN 2023. The BEST location with a HUGE flat three-quarter-acre lot with usable land. One of the best deals you can possibly find in Hillsborough. The lot features sprawling lawns, a sparkling pool, & total privacy. Lots of space to play and entertain with the whole family. Minutes from Downtown Burlingame & prestigious schools. This Monterey Colonial has been totally transformed. Luxurious finishes can be found all throughout. Excellent floor plan overflowing w/ natural light from large windows & skylights. Host with ease. Well-sized living room & kitchen / family room. The NEW modern kitchen is constructed with high-end appliances. All the spacious bedrooms are en-suite with NEW pristine bathrooms & new closets. Lower level can be a home gym / play room / entertainment room. Home office and laundry room. Most lights controlled by smart features. Brand new heater. TOO MANY DETAILS, the list goes on and on. Take advantage of this rare opportunity.

Newly transformed modern farmhouse in the Carolands, walking distance to West school. This 4BR 4.5BA home offers an open and casual layout. Greeted by a paved semi-circular driveway, with exterior features such as wrap around terraced yard with planting areas, a huge private courtyard, sport court and a large deck with views of the airport and bay. The interior is equipped with hardwood floors, recessed lighting, and an open floor plan. The remodeled kitchen looks out onto the courtyard and also overlooks the dining area. Nearby lies the bright and spacious formal LR with vaulted ceilings, and a gorgeous fireplace. Adjacent to the LR is bonus room, perfect for an office. Sliding glass doors connect you to the private courtyard, making this home ideal for indoor/outdoor entertaining. Other highlights include a grand master suite, updated bathrooms, and a large detached garage with a bonus room, extra storage and plenty of guest parking.

Beautifully Updated & Located in Prestigious Lower Hillsborough, this is the Perfect Blend of Traditional Timeless architecture & today's Modern Lifestyle. The open floor plan features fine details & craftsmanship, offering comfort, style, and elegance. Interior spaces include a grand foyer with a sweeping staircase, a sizeable step-down living room w/fireplace, a formal dining room &updated kitchen that extends into the family room & casual eating area. The second level hosts an exquisite Primary Suite overlooking the delightful gardens, and two additional bedrooms, with an enlarged walk-in closet and adjoining bath. The top floor has a Massive 4th Bedroom/Bonus Room, ideal for an office, media, or playroom. The rear grounds feature a spacious patio outside the family & living rooms, freshly landscaped gardens,& Large entertainment upper deck with a pool & hot tub. This Fabulous Home is Only Minutes away from Shopping, Restaurants & both Downtowns of Burlingame&San Mateo Welcome Home!

GREAT OPPORTUNITY FOR THIS TROPHY ESTATE***If you are looking for the best of the best, this is a once-in-a-lifetime opportunity for you to enjoy your life! After years of renovations, 1868 Floribunda Avenue is ready for you to view! The lot is almost 5x bigger than standard lots, all usable! Renovated to the highest quality, situated in one of the best locations in Hillsborough! Nearly 20,000 square feet throughout 6 buildings. New custom-built water well. Three private gates - resident driveway, guest driveway, and pedestrian walkway. No expense was spared for this property to reach the ultimate heights in a smart & secure dream home! You have to see it, to believe it! Qualified buyers only; qualifications requested in order to be screened before showings.

Spacious & elegant, this Hillsborough beauty showcases luxury interior design complimented by gorgeous outdoor living. The grove of heritage olive trees beckons as you enter the spectacular courtyard with its rose garden, calming fountain & private patio. Anchoring the home is the remodeled kitchen with Carrara marble counters, custom cabinetry, stainless steel appliances, Wolf range & artisan tile. The living & family rooms are each warmed by a brick fire place. Step inside the fabulous butler pantry & attractive mudroom conveniently situated next to the large 3 car garage. Outside, a magical oasis awaits with the expansive backyard featuring fresh landscaping, new lawn, a pool, spa, & sport court with separate patio areas on the oversized .64 acre lot. This stunning Hillsborough home is close by downtown San Mateo & Burlingame with a variety of popular outdoor cafes, restaurants & shopping. Excellent schools and easy access to highways, Caltrain, Bart, & S.F. Airport.

Dream a little dream in Hillsborough, California. Seize the moment on thisestate. Great size home on large lot approximately 25,200 square feet. This is a great opportunity to put your finishing touches on this gem. Don't miss thisunique chance to say ''hello'' to your new dream getaway! All potential buyersare asked to check with City, County, Zoning, Tax, and other records todetermine all details on this property listed above to their satisfaction. Thisis an AS-IS REO property.

Elegance and quality craftsmanship radiate from all corners of this Modern French Chateau. Mature trees line the private drive leading to the thoughtfully-designed home set within a beautifully landscaped .63 acre lot. From wide planked wood floors and arched doorways to grand formal spaces and sparkling en-suites, this estate property provides that embellished interior you've been looking for in a quiet, friendly neighborhood. The spacious foyer opens to a soaring three-story entry inviting you to explore the impressive great room where natural light pours in through French doors, illuminating the quality finishes while offering breathtaking views. You'll be more impressed by the amount of space this home offers on every level where possibilities are endless! Whether its space for a game room, home theater, gym, music studio, wine cellar or space for guests, this home has it all. Privacy and tranquility have never looked better together.

The bright, flowing indoor floorplan has been tastefully updated and is move-in ready. The home carries the dual-pedigree of San Francisco design pioneers architect Gardner Dailey and famed landscape architect Thomas Church. The indoor living areas naturally extend through French doors from the spacious main hall into a landscape of ambling paths under mature oaks, welcoming rose gardens, and shaded lawns. The circular terraces and circular Emerald pool are signature Church design elements as featured in Architectural Forum magazine and two Thomas Church books.

One-of-a-kind corner-lot Mediterranean-inspired estate that is seated on a generous 16,450 sqft lot. Located in the sought-after neighborhood of Hillsborough Park. This 3 story home shows off stunning architectural aesthetics w/ tall white columns, spectacular arches, terracotta accents, wrought iron elements, & more! Inside this house, you will be greeted by a cozy fireplace, high ceilings, exposed ceiling beams/truss that add a dramatic sense of strength & heft to the living room. This house has a spacious kitchen, formal dining, & breakfast nook. There is a family room that can be found in the basement, & this house has a space for a potential laundry room. There are 3 master suites upstairs, 1 bd on the main level & 1 on the lower level of the house. This home has plenty of windows throughout the entire house that brings in an abundance of natural light. Huge & Extra wide manicured lawns w/ plants & trees are found at both the front/rear exterior of this home w/ a large side patio.

SHOWCASE HILLSBOROUGH HOME REMODELED FROM THE STUDS OUT IN 2022! Never lived in since the remodel! Be the first to reside in such an elevated living experience. This home offers up-to-date contemporary designs with the finest appointments available; perfect for the modern family. Wide-open modern floor plan w/ tons of natural light thanks to tall windows & 3 skylights. The great room is huge and blends the living room/kitchen seamlessly; the perfect hosting platform. White oak hardwood runs from edge to edge. Recessed lighting illuminates ever corner. The brand new gourmet chef's kitchen has all top-of-the-line appliances from Thermador, Bosch, Sub-Zero, & more! You'll also find a center island w/ a built in sink & integrated appliances + quartz countertops. Easily master your culinary skills. All the bedrooms are ensuite & comfortable. Bathrooms feature polished quartz, rainfall shower heads, double vanity, etc. 2 AC units, 2 Furnaces, & a wrap around backyard/garden. DON'T MISS OUT!

Magnificent Mediterranean Estate with 6 bedrooms, 6 bathrooms, plus an additional two half bathrooms/Soaring ceilings with custom skylights provide an abundance of natural lighting over the dramatic entry that features grand columns and graceful staircases with custom ironwork and a cascading water wall feature/Spacious Primary bedroom with high coffered ceiling, bold crown molding, fireplace, a separate walk-in closets and spacious main bathroom that features a large shower with dual heads and a separate tub/Sizable office/study with cozy fireplace and built-in bookshelves that are blessed with an abundance of natural lighting from multiple sides/The resort-style backyards is perfect for entertaining and relaxing. Dramatic views of San Francisco Bay and beyond can be enjoyed from the spacious terraces and patio that surround the huge refreshing pool and jacuzzi. Other feathers include a sports court, water fountains, fireplace, and fire pit. A spacious gated driveway and 3-car garage.

Recently completely remodeled to studs, w/ 1,200 SqFt* of additional space added. Nestled on a private 1.5-acre lot at the end of a tree-lined driveway. Exquisite craftsmanship, complementary designs, & an elevated living experience awaits. Brimming w/ premium amenities & appointments, this home will inspire you every day. A highly desirable, modern open floorplan w/ hardwood flooring extends throughout. The great room flows seamlessly to the dining area & kitchen, perfect for hosting. An expansive wall of La Cantina doors opens up to a long balcony w/ stunning canyon views. The newer gourmet chefs kitchen features all top-of-the-line Thermador appliances such as a fridge, espresso machine, 6-burner stove, microwave drawer & MORE, + a center island w/ a built-in sink. The ensuite bedroom is spacious w/ the bath featuring a double vanity & soaking tub. All other baths have double vanities. 2 AC Units, a backyard, a landscaping area, a sports court, & approved plans for an ADU.

Over 1.8 acres, every square foot totally level, A perfect rectangle, Subdividable into 2 lots. One of only a few parcels of this size and quality in all of Hillsborough. Located in the most desirable location of lower Hillsborough among of some of Hillsborough's most beautiful estates. The perfect building site. When gone there will be no others.

Discover this stunning custom home in the Lakeview community of Hillsborough. Completely rebuilt, the unique design and exquisite features will captivate you. Inside, soaring ceilings, arched doorways, and chandeliers welcome you. The chef's kitchen boasts quartz counters, a 9-foot island, and Viking appliances. The home includes a large office, 5 bedrooms, and 4 en-suites. Details include walnut floors, tray ceilings, and custom casement windows. Accordion doors open to an entertainer's paradise with an outdoor kitchen, fireplace, wine cellar, jacuzzi, pool, and 5-pin putting green. Simply put: exceptional design for luxurious living.