The 5 Most Expensive Homes for Sale (and Sold) in Calabasas, CA — of All Time
There’s luxury — and then there’s Calabasas, where the air smells faintly of eucalyptus, ambition, and freshly detailed Bentleys. Here, privacy isn’t just desired — it’s engineered. From hillside moderns wrapped in glass to Lake Como villas reborn under California sun, this corner of Los Angeles proves that when money talks, architecture listens
At the heart of it all stands The Oaks of Calabasas — a highly desirable sanctuary where craftsmanship meets celebrity. Home to icons such as Britney Spears, Kourtney and Khloé Kardashian, and a long list of creatives seeking serenity behind guarded walls, The Oaks remains the city’s defining symbol of prestige. Every home here tells a story of design, ambition, and quiet grandeur.
🏠 25354 Prado De La Felicidad — SOLD 2021
Sold Price: $30,000,000 (Listed $34 M | $4 M below)
Specs: 8 BD • 14 BA • 22,000 sq ft • Lot 76,130 sq ft • $1,545 / sq ft
Unique for: A French-modern showpiece by Michael Palumbo Design — wellness spa, basketball court, putting green, theater & infinity pool overlooking The Oaks’ final ridge lots.
🏠 25314 Prado De La Felicidad — SOLD 2022
Sold Price: $20,000,000 (Listed $24.995 M | $4.99 M below)
Specs: 7 BD • 11 BA • 14,021 sq ft • Lot 71,216 sq ft • $1,782 / sq ft
Unique for: A modern-French provincial masterpiece — rose gardens, goldfish pond, 9-car garage, subterranean theater & panoramic mountain vistas.
🏠 25305 Prado De La Felicidad — ACTIVE
List Price: $16,995,000
Specs: 7 BD • 10 BA • 15,745 sq ft • Lot 55,662 sq ft • $1,079 / sq ft
Unique for: “Villa Bellezza,” a rare Italianate triumph by William Hablinski — 28-ft ceilings, Venetian plaster, Chanel-inspired pool, cinema, wine cellar & unrivaled ridge-top privacy.
🏠 25242 Prado Del Grandioso — ACTIVE
List Price: $15,999,000
Specs: 7 BD • 9 BA • 14,715 sq ft • Lot 49,535 sq ft • $1,087 / sq ft
Unique for: A newly reimagined showpiece — 30-ft ceilings, dual kitchens, glass-walled wine lounge, theater, gym, guest house & resort grounds with pool, putting green & sports court.
🏠 3121 Old Topanga Canyon Rd — ACTIVE
List Price: $15,000,000
Specs: 5 BD • 8 BA • 8,953 sq ft • Lot 200,699 sq ft (≈ 4.6 acres) • $1,675 / sq ft
Unique for: Architect Robbin Hayne’s “Skycrest” — an X-shaped glass marvel with 24-ft ceilings, private courtyards, theater, wine cellar & endless canyon-to-city views.- Image and listed by Killer Williams R.E. Services
🏠 25400 Prado De La Felicidad — SOLD 2008
Sold Price: $6,000,000 (Listed $14.995 M | $8.99 M below)
Specs: 8 BD • 12 BA • 15,000 sq ft • Lot 86,684 sq ft • $999 / sq ft
Unique for: A grand Spanish-style compound on nearly 2 acres with 20-car garage, theater, game room & guest house — a snapshot of The Oaks’ early architectural ambition.
✨ A Legacy Written in Stone and Light
Each of these estates captures a moment in Calabasas history — from record-breaking sales to daring design that keeps redefining California luxury. From canyon peaks to guarded gates, The Oaks continues to set the standard — a place where the architecture is ambitious, the lawns are immaculate, and the price tags politely start with eight digits.
If you’re ready to explore the best of the best in Calabasas, or discover your own private sanctuary within our neighborhoods, I’d be honored to guide you there — where imagination meets craftsmanship, and every wish is within reach.
— Inna Ivchenko, Realtor® | Calabasas & Beyond
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