Imagine stepping into a world where architectural brilliance meets unparalleled luxury. Across Southern California, five extraordinary estates, priced between $3.6 million and $4.3 million, redefine elegance with their bespoke designs. From the historic Craftsman sophistication of South Pasadena to the modern-traditional grandeur of Simi Valley and the rare waterfront charm of Ventura’s Tuscan villa, each property offers a distinct lifestyle—whether rooted in timeless heritage, expansive privacy, or serene coastal access. These homes are not just residences; they are masterpieces crafted for those who seek exclusivity and inspiration in every detail.
1524 Milan Avenue | $4,298,000


Michele Downing

Michele Downing
Positioned along one of South Pasadena’s most prestigious, tree-lined streets, this breathtaking early 1900s Craftsman Estate stands as a masterpiece by renowned architect and builder G. Lawrence Stimson. A testament to timeless sophistication, the residence effortlessly marries classic charm with modern convenience. A meticulously landscaped front yard welcomes you to the inviting covered porch, setting the tone for the elegance within. Step through the formal entryway and discover an expansive living room, where a striking box-beamed ceiling, an exquisite fireplace, and custom built-ins create a warm, refined ambiance. Every detail of this home reflects Stimson’s visionary craftsmanship, offering a rare opportunity to embrace a lifestyle of grace and heritage. Ideal for those who appreciate architectural history, this estate provides a serene retreat amidst the vibrant surroundings of South Pasadena, blending past and present in perfect harmony.
- Price:
- $4,298,000
- Size:
- 4,393 sq ft
- Contact:
- Michele Downing, Compass, 626.523.6939
A Truly Unique Property | $3,999,999


Martha Azizi

Martha Azizi
Situated within an exclusive gated community, this custom executive estate offers a rare blend of privacy and prestige on over an acre of pristine land. With only two homes on this secluded street, tranquility defines the setting. The home itself marries modern traditional design with timeless elegance, featuring soaring ceilings and intricate custom woodwork that exude warmth and grandeur. The open floor plan seamlessly connects the formal living and dining spaces to a gourmet kitchen, a chef’s haven equipped with Wolf appliances, a Sub-Zero refrigerator, and a sprawling island—perfect for gatherings. Overlooking a lush, tree-lined landscape, the primary suite serves as a personal retreat with a spa-inspired shower, soaking tub, and expansive walk-in closet. Outside, a four-car garage, RV parking, a massive pool and spa, a basketball court, and vast grassy areas invite endless possibilities for relaxation and recreation.
- Price:
- $3,999,999
- Size:
- 6,338 sq ft
- Contact:
- Martha Azizi, Agents of LA, 805.501.5708
2790 Sailor Ave | $3,925,000


Fred Evans

Fred Evans
Situated along the serene waterways of Ventura Keys, this Mediterranean Tuscan-style villa offers a captivating blend of elegance and coastal charm. Rebuilt in 2009, the spacious two-story residence spans approximately 3,458 square feet, featuring three bedrooms and four bathrooms. Inside, the living room impresses with a hand-carved marble fireplace and a temperature-controlled wine closet, perfect for refined gatherings. Step outside to the waterfront entertainment deck, where panoramic views and gentle sea breezes create an idyllic setting for relaxation or hosting. A private, approximately 38-foot boat dock adds a unique touch, catering to nautical enthusiasts eager to explore the open water. With its thoughtful design and prime location, this home effortlessly combines luxury with the laid-back allure of waterfront living, offering a lifestyle of both sophistication and adventure.
- Price:
- $3,925,000
- Size:
- 3,458 sq ft
- Contact:
- Fred Evans, RE/MAX Gold Coast Realtors, 805.267.6701
Contemporary Retreat With Panoramic Views | $3,750,000


Ryan Shimp

Ryan Shimp
Set against the serene backdrop of Westlake Trails, this newly redesigned waterfront home offers a harmonious blend of contemporary elegance and breathtaking Conejo Valley views. Elevated above the street and accessed via a private, winding driveway, the residence ensures unparalleled privacy. Inside, expansive windows flood the living spaces with natural light, highlighting luxurious finishes and modern design. The heart of the home, a stunning kitchen, seamlessly connects to open entertaining areas, ideal for gatherings with family or friends. Step outside to a resort-style backyard, where a sparkling pool and soothing spa create an oasis for relaxation. With every detail thoughtfully crafted, this property embodies a lifestyle of sophistication and tranquility, perfectly positioned to enjoy the beauty of waterfront living while remaining a private retreat from the everyday.
- Price:
- $3,750,000
- Size:
- 4,431 sq ft
- Contact:
- Ryan Shimp, Engel & Völkers, 818.314.8606
Timeless North Ranch Luxury | $3,600,000


Listing agents: Jordan Cohen & Aimee Mckinley

Listing agents: Jordan Cohen & Aimee Mckinley
Set against the serene waterfront of prestigious North Ranch in Westlake Village, this expansive estate spans over 5,027 square feet of meticulously crafted living space on a generous 17,859-square-foot lot. Tucked at the end of a tranquil cul-de-sac, the home offers 6 bedrooms and 4 bathrooms, blending comfort with elegance. A grand two-story entryway welcomes you into an open-concept layout, perfect for both intimate gatherings and lively entertaining. The formal living and dining rooms exude sophistication, while the family room flows effortlessly into a gourmet kitchen featuring granite countertops, stainless steel appliances, and rich wood cabinetry. Outside, a backyard oasis awaits with a resort-style pool, spa, sport court, and sprawling lawn. With hardwood floors, high ceilings, and proximity to top-rated schools, scenic trails, and fine dining, this property embodies refined rural living.
- Price:
- $3,600,000
- Size:
- 5,027 sq ft
- Contact:
- Jordan Cohen & Aimee Mckinley, RE/MAX One, 818.435.5220 , 805.405.0978












