Welcome to Culebra Park, a magical retreat in the heart of Hillsborough estate country. After decades of cherished memories by one family, this is the first offering to the market since 1970! The architecture delivers the best of Revival romance, circa 1935, cast in the iconic Monterey Colonial style. The current owners have honored the home with love and their luxurious upgrades, including a spectacular Primary Wing and indoor/outdoor Family Room addition. The Primary Wing is a true Wow Factor complete with its own Office, huge marble bathroom, and surely one of the grandest walk-in closets in Town! 

Appointments include 5 bedrooms, 5.5 bathrooms (Plus Primary Office) spanning 5,425 sq. ft. of living. The principal living areas are all strategically lined up along the rear of the home, promoting smooth garden entertaining through French doors. Stately 9 ft. ceilings enhance gracious dimensions in the 25 x 18 Living Room and 15 x 18 Formal Dining Room, each with direct access to the rear terraces. The surrounding gardens are so picturesque, they infuse the interiors with the ambiance of a dreamy private park. Connected to the kitchen, the family room addition was executed with a contemporary touch, including a wall of glass and 12 ft. vaulted ceiling. A tucked-away lower level expands options with space for media room, gym, or artist studio, plus an Old World wine cellar.

The rarity and beauty of the floorplan lies in the top floor, where you will find 4 bedrooms all together (plus Primary Office), with both the east and west facades opening to quintessential Monterey Colonial verandas. From the rear veranda, you will survey the majestic park-like grounds of .73 acre...a sylvan setting of heritage trees, velvety lawns, and Bay vistas on the horizon. The secluded and 100% usable environs invite you to dream up a future pool, ADU, Firepit Lounge, and outdoor kitchen with ease. Award-winning landscape architect Terra Ferma has already drafted dazzling conceptual plans that will elevate this pristine park into a Five-Star resort. 

Since the 1920's, this prestigious South Hillsborough location has hosted many of the Town's leading estates, topped by the nearby #1 sale in history at 835 Chiltern. The sense of privacy and East Coast architectural grandeur are uncanny. For 2023, the home right next door at 869 Culebra was the #1 sale of the year at $17,000,000. Hillsborough's beautiful central gathering spot of Vista Park is just two blocks away (0.3 mile) for a walk-friendly diversion with playground, basketball court, and grassy field. Like our most timeless estates, 865 Culebra Road tells the story of Hillsborough elegance...an opportunity that has been a half century in waiting...a classic and enduring statement now ready for its next chapters.

At a Glance

• 5 bedrooms, 5.5 bathrooms, plus deluxe Primary Office with Bay view, fireplace, and built-in workstation
• Approx. 5,425 sq. ft. of living (per paid vendor Floorplan Visuals) 
• Lot is 31,950 sq. ft. (0.73 acre) per county record
• Grand rooms on the main level including the classic Living Room and Dining Room opening to the vast terraces
• Exceptional top floor bedroom layout (very hard to come by!) of 4 bedrooms and 3 bathrooms, plus Primary Office
• Main level guest bedroom and hall bath ideal for guest or au pair (plus a separate powder room) 
• Spectacular Primary Suite comprises its own wing featuring Custom Office with fireplace, Bay-view bedroom, large marble bathroom with heated floors, and enormous walk-in closet with two islands and custom wardrobes
• Lower level with bonus destinations for media room, artist studio, wine cellar, plus full bath. 
• Attached 2-car garage with extra storage. Oversized motor court and turnaround. 
• Assigned to South Elementary and Crocker Middle
• 7 minute walk (0.3 mile) to Vista Park