Luxury Home Magazine Silicon Valley | SF Peninsula | Coastal Issue 19.2
S ILICON V ALLEY • SF P ENINSULA • C OASTAL
Iconic Crosby Estate on 2.4+ Acres in Hillsborough
• Built in 2003 by Chessler Construction in the prestigious Blue Oaks neighborhood
• 5 bedrooms, 6 full baths, and 2 half-baths
• Approximately 7,735 total square feet
• Formal living and dining rooms, executive office, plus family room off the gourmet kitchen
• Luxurious primary suite with Bay views
• Lower-level recreation room, full bar, wine cellar, and fitness center
• In-ground spa, fireplace, and outdoor shower
• Approximately 1.29 acres
• Backup generator
• Excellent Portola Valley schools
Brian Chancellor has built his leadership position in Palo Alto and on the Peninsula one successful relationship at a time. Brian believes in honesty, transparency, community, and a steadfast commitment to always act in his clients' best interests. If you're buying or selling a home, there's never been a better time to chat with Brian. We think you'll agree, trust, combined with over 3 30 years of local real estate experience, makes for one perfect blend.
444 TENNYSON AVENUE, PALO ALTO
Property Totals: ±9,029 SqFt | Lot ±0.46 Acres
Main Residence: 4 Beds | 4 Full Baths
2 Half Baths | ±8,219 SqFt
Detached Guest Suite: 1 Bed | 1 Full Bath | ±340 SqFt
Pool House: Kitchenette | 1 Full Bath | ±470 SqFt
Detached 3-Car Garage:
5 Car Capacity (2 Lifts) | ±975 SqFt
Offered at: $24,888,000
TennysonPaloAlto.com Saratoga Estate: A World-Class
Michael Dreyfus
650.485.3476
m.dreyfus@ggsir.com Lic. #01121795
22480 MT EDEN ROAD, SARATOGA
Main Residence: 6 Beds | 6.5 Baths
Attached 4-Car Garage | ±7,500 SqFt
Pool House: 1 Bed | 1 Bath | ±920 SqFt
Exercise Studio: ±665 SqFt
Apartment 1: 1 Bed | 1 Bath | ±390 SqFt
Apartment 2: 2 Beds | 1 Bath | ±1,280 SqFt
Gym: ±1,250 SqFt
Barn: ±685 Finished SqFt | ±5,150 Unfinished SqFt
Lot: ±37.025 Acres
Offered at: $18,500,000
MtEdenSaratoga.com
Michael Dreyfus
650.485.3476
m.dreyfus@ggsir.com Lic. #01121795
Michael Dreyfus
650.485.3476
m.dreyfus@ggsir.com
Lic. #01121795
Hillary Ryan 707.312.2105
hillary.ryan@sothebys.realty Lic. #01934302
12 Car Garage: ±2,600 SqFt Storage Barn: ±9,000 SqFt Party Barn: ±2,000 SqFt ATV/Quad Barn: ±1,000 SqFt Greenhouse: ±8,000 SqFt
1,119± Acres Across 6 APNs Price Upon Request
TheSummitSonoma.com
Michael Dreyfus
650.485.3476
m.dreyfus@ggsir.com
Lic. #01121795
Kristie Eddy
949.577.1717
k.eddy@ggsir.com
Lic. #02095273
PUBLISHER
Tim Crenshaw
650.996.6549
tim@lhmsvp.com MARKETING
Angie Crenshaw
650.559.9200
ads@lhmsvp.com
Market Perspective: The Peni nsula | Q1 2026
Erika Demma
455 Pinehill Road
Entertainment, Comfort, and Craftsmanship Redefined.
Set atop a private 2.5-acre promontory in Hillsborough, this custom estate commands sweeping Bay and canyon views from nearly every room. Designed by MAK Studio, the residence features a striking stone-and-wood façade, soaring 22-foot ceilings, and expansive walls of glass that blur the line between indoor and outdoor living.
Resort-caliber grounds feature a 50-foot pool with outdoor bath and shower, expansive lawn, fire pit terrace, scenic viewing areas, and a custom 10-hole putting green with pitching area and sand trap. The estate is completed by dual two-car garages, a motor court for five additional vehicles, and ample guest parking.
Phil Chen, Broker-Associate
Christie’s Sereno | Sybarite Luxury Realty
DRE# 01715177 | 415.271.1920
phil@sybariterealty.com
Artful Living on Every Level.
• Private office ideal for executive use
• Dedicated fitness studio for at-home wellness
• Golf simulator for year-round recreation
• Expansive wine cellar and custom home bar
• Crestron automation system seamlessly integrates lighting, climate, shades, and security
• Energy-efficient infrastructure including radiant heat, solar power, and tankless water systems
• Full backup generator for uninterrupted comfort and reliability
Price Available Upon Request.
The Gina Haggarty Group
2026 New Construction Portfolio
A Modern Château in Old Palo Alto
A rare find! An exquisite, French-style residence unfolds elegance across 6,024 square feet, including garage and pool house. Tree-lined privacy protects the rear ground’s pool, equipped with a resistance current you can swim against, and spa. The spacious living areas are accentuated by high ceilings and rich hardwood floors, offering a seamless blend of sophistication and comfort. Features five generously proportioned bedrooms, eight bathrooms, a theater room, large recreation room, office, wine cellar, elevator, luxury bathtub, steam shower, gourmet kitchen, breakfast nook, butler's kitchen, pantry room and more. Enjoy cozy evenings by the fireplace in the living room or master bedroom, each offering a serene ambiance for intimate gatherings or solitary reflection. This property is more than a home; it is an opportunity to experience an unparalleled lifestyle of luxury and elegance in Old Palo Alto, the heart of the Bay Area.
Experience Old Palo Alto at its most refined Call to inquire about the property.
Co-listed with Jenn Gilson, Golden Gate Sotheby’s International Realty
A secluded trophy estate in the heart of highly coveted Lower North Hillsborough, this extraordinary 2.4+ acre property offers rare scale and privacy on one of the towns largest parcels. Originally designed by acclaimed architects John Bakewell Jr. and Ernest Weihe, the French Chateau-inspired residence was once home to Hollywood icon Bing Crosby and is rich with storied provenance, including connections to the legendary Seabiscuit and curated antique details from the Hearst Collection. Thoughtfully updated by the current owner, the home spans four levels and features 11 bedrooms, 10 full baths, and 5 half baths, blending grand architectural presence with a warm, livable layout. Designed for both intimate daily living and elegant entertaining, the floor plan includes multiple salons, a formal dining room, a wood-paneled library, a private office, and a distinct guest wing. The park-like grounds showcase sweeping lawns, a resort-style pool with fountains, and expansive open space, creating a serene and majestic setting. With its remarkable history, refined craftsmanship, and exceptional acreage, this is a truly irreplaceable legacy estate an unparalleled opportunity to own a landmark property from California’s Golden Era.
THE CHÂTEAU, HILLSBOROUGH
7 Bed | 8 Bath | 9,675 Sq Ft | 0.85 Acre Lot
RALSTON AVENUE, HILLSBOROUGH 5 Bed | 7 Bath | 10,495 Sq Ft | 2 Acre Lot
Daniel Casabonne Presents
4377 Warm Springs Road, Glen Ellen | An Incomparable Wine Country Estate
This estate, known as Villa Montebella, won the 2024 Vacation Property of the Year award. Now newly refinished, the villa is ready to become someone’s family residence, a home for multigenerational living, or an incomparable vacation mecca for family and friends. The compound, which lives as an 8-bedroom estate, comprises 5 buildings. Surrounding the buildings are a Cabernet vineyard, pool, hot tub, bocce court, play area, pool house, palms and other mature trees, and a 4,860-sq-ft wine cave. Showings by private appointment only.
A striking expression of modern architecture set against the beautiful vistas of Las Trampas and overlooking Roundhill Country Club, this newly constructed residence invites you to experience life from an elevated perspective.
Simon Sahi brings championship discipline and deep local insight to Silicon Valley’s luxury real estate market. A former professional basketball player, Simon applies the same precision, strategic focus, and winning mindset that defined his athletic career to every transaction.
A longtime Peninsula homeowner and resident, he knows the exclusive neighborhoods of Los Altos, Palo Alto, Menlo Park, Atherton, and Woodside intimately. With over ten years of full-time experience and more than 250 million in closed sales, Simon specializes in high-end properties from modernist hilltop estates to timeless family compounds.
Clients value his calm authority, sharp negotiation skills, and genuine ability to connect. He listens deeply, anticipates needs, and builds lasting relationships based on trust and integrity.
In a competitive market, Simon offers something rare: the poise of an elite athlete, the perspective of a true local, and the sophistication to deliver exceptional results for discerning buyers and sellers.
Partner with Simon Sahi for expert guidance in the Peninsula’s most coveted luxury enclaves.
Simon Sahi
East Coast Grandeur meets Northern California Living
TRI-LEVEL ESTATE OFFERS POOLHOUSE, 3+ ACRES Transport yourself to the East Coast in this incomparable custom estate. Gated acreage framed by California oaks reveals an exquisite Shingle-style home surrounded by bridges, enchanting gardens, a three-car garage, and fully functional poolhouse with saltwater pool and spa.
Faced by a circular gravel drive, the tri-level main residence built in 2010 has been wonderfully maintained, boasting all ensuite bedrooms, a turret study, gym, and media lounge with full bar. Enjoy a sensational master chef’s kitchen, ultra-luxurious primary suite, multiple fireplaces, surround sound, and ground-level guest/au pair quarters. Grounds offer paver terraces, a barbecue island, and expansive synthetic lawns for leisure or entertaining.
Moments from shopping, dining, trails, and breathtaking scenery, this piece of bucolic paradise is nestled near tech and venture capital centers, and only ~ 30 minutes from SFO and SJC.
1031 Exchange
If a vacation home is primarily held as an investment property, it may be eligible for a 1031 Exchange.
The property should be rented at fair market value for at least 14 days per year.
Personal use should not exceed the greater of: 14 days, or 10% of the days the property is rented.
If these conditions are met for two consecutive 12-month periods, the IRS generally treats the property as held for investment, making it eligible for a 1031 Exchange.
Vacation homes can quietly appreciate for years. If structured properly, owners may be able to sell, defer taxes and reinvest into a larger or more diversified investment property.
Your investment deserves expertise. Let’s make your next sale a tax-smart one.
Tel: 877-471-1031
www.ax1031.com
— FULL-SERVICE INTERIOR DESIGN — End-to-end orchestration from concept to execution. — LANDSCAPE DESIGN — Outdoor environments shaped through layout, flow, planting direction, and furnishing concepts. — ADVISORY —
Provide vision and aesthetic guidance to clarify direction and support confident vendor alignment.
— VISUALIZATION —
Photorealistic interior and exterior renderings, paired with immersive virtual walkthroughs for clarity before execution.
273 Austin Ave, Atherton | $28,250,000
Listed by Mary & Brent Gullixson
3426 17 Mile Drive, Pebble Beach | $24,500,000
Buyer Rep., Shelly Mitchell Lynch
3490 Tripp Road, Woodside | $16,250,000
Listed by and Buyer Rep., Scott Dancer
1806 Doris Drive, Menlo Park | $12,000,000
Listed by Erika Demma
161 Lowell Ave, Palo Alto | $11,550,147
Listed by Brian Chancellor
222 Albion Ave, Woodside | $10,500,000
Buyer Rep., Mary & Brent Gullixson
1483 Bonifacio Road, Pebble Beach | $10,000,000 Listed by Tim Allen
190 Almendral Ave, Atherton | $32,000,000 • Listed by Mary & Brent Gullixson
LUXURY SALES
Highlighting LHM agents’ recent successes in Silicon Valley & Coastal Regions
6 Cedar Lane, Woodside | $23,500,000 • Listed by Scott Dancer & Jenn Gilson
588 Craig Road, Hillsborough
Listed by Phil Chen
12359 Farr Ranch Road, Saratoga | $7,340,000 • Listed by Nevis & Ardizzone
2930 Privet Dr, Hillsborough
Set behind private gates in Hillsborough’s prestigious Skyfarm, this 9,035 sq ft estate offers sweeping San Francisco Bay views, dramatic vaulted ceilings, and sun-drenched living spaces. Highlights include a chef’s kitchen, multiple fireplaces, formal and family rooms, a luxurious primary suite, six additional bedrooms, staff quarters, wine cellars, and a glass-enclosed indoor pool with spa, all framed by expansive patios and manicured grounds.
