300 Uplands Drive, Hillsborough, CA 94010

• 5 beds |
• 5 baths |
• 3,800 sqft

Property Description

Located in prime Lower South Hillsborough, this beautifully updated home sits on approximately 0.42 acres of flat, private, and meticulously landscaped grounds designed for effortless indoor-outdoor living. The front yard features manicured turf and a putting green, while the backyard offers a resort-like setting with a pool, built-in BBQ, outdoor TV, and multiple entertaining areas. Light-filled interiors showcase a seamless flow with a spacious kitchen/family room combination and formal living and dining rooms, all oriented toward the backyard. A rare highlight is the presence of two primary suites, providing exceptional flexibility. The upstairs primary retreat features dual closets, a private deck overlooking the pool, a spa-like bath with soaking tub, dual sinks, and high ceilings, plus an attached office with built-ins. A nursery is conveniently located adjacent to this suite. A second primary suite is located on the main level and overlooking the backyard. Alongside, is 2 additional bedroom suites, offering comfort and privacy for family and guests. Ideally located, mere blocks from Crystal Springs Uplands School, South Elementary, The Episcopal Day School, and just minutes to downtown San Mateo.

Listing Status:

Pending

Date Added:

April 23, 2026

Data Last Updated:

May 21, 2026 at 12:20AM

Listing Office:

Compass : (650) 375-1111

Listing Agent:

Sternsmith Group : 650-678-5455

MLS ID:

ML82044375

Interior

• General: Walk-In Closet(s)
• Appliances: DishwasherGas CooktopMicrowaveRefrigeratorVented Exhaust Fan
• Flooring: CarpetTileWood
• A/C:
• Heating:
• Fireplace: Living RoomFireplace

Exterior

• General: In Ground
• Pool: In Ground
• Parking: Parking spaces: 2

Construction

• Roofing: FiberglassShingle
• General: 2

Location

• Originating MLS: CRMLS_MLSL
• School District: Other
• County: San Mateo

Lot

• Zoning: R10025032392030

Utilities

• Water: Public
• Sewer: Public Sewer

Financial

• Source: CRMLS_MLSL