300 Uplands Drive

• Sun Apr 26, 2:00 pm - 4:00 pm

  A picture perfect home on a flat and beautifully landscaped lot in Lower South Hillsborough. With 2 primary suites, one on each floor and 2 additional en-suite bedrooms, this home exudes luxury, beautiful millwork and natural light at every turn.

• Tue Apr 28, 11:00 am - 1:00 pm

  A picture perfect home on a flat and beautifully landscaped lot in Lower South Hillsborough. With 2 primary suites, one on each floor and 2 additional en-suite bedrooms, this home exudes luxury, beautiful millwork and natural light at every turn.

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.

Days on Market

3 days

Current Status

Active

Original Price

$6,750,000

List Price

$6,750,000

On Market Date

Apr 23, 2026

Property Type

Single Family Home

Area

441 - Brewer Subdivision/Upland

Zip Code

94010

MLS ID

ML82044375

APN

032-392-030

Year Built

1954

Stories in Building

2

Possession

COE

Data Source

MLSL

Origin MLS System

MLSListings, Inc.

Bed

5

Bath

5 (4/1)

Double Sinks, Primary - Tub with Jets, Showers over Tubs - 2+, Skylight, Stall Shower

Parking

2

Attached Garage, Electric Gate

SQ FT

3,800

SQ FT Source

Unavailable

Lot SQ FT

18,089.0

Lot Acres

0.415266 Acres

Pool Info

Pool - In Ground, Pool / Spa Combo

Kitchen

Cooktop - Gas, Countertop - Stone, Dishwasher, Exhaust Fan, Island, Microwave, Oven - Built-In, Refrigerator

Cooling

Other

Dining Room

Dining Area, Formal Dining Room

Disclosures

Natural Hazard Disclosure

Family Room

Separate Family Room

Flooring

Carpet, Hardwood, Tile

Foundation

Concrete Perimeter and Slab

Fire Place

Living Room

Heating

Central Forced Air - Gas

Laundry

Washer / Dryer

Possession

COE

Fee

Unavailable

MLS and other Information regarding properties for sale as shown in Theo have been obtained from various sources such as sellers, public records, agents and other third parties. This information may relate to the condition of the property, permitted or unpermitted uses, zoning, square footage, lot size/acreage or other matters affecting value or desirability. Unless otherwise indicated in writing, neither brokers, agents nor Theo have verified, or will verify, such information. If any such information is important to buyer in determining whether to buy, the price to pay or intended use of the property, buyer is urged to conduct their own investigation with qualified professionals, satisfy themselves with respect to that information, and to rely solely on the results of that investigation.

School data provided by GreatSchools. School service boundaries are intended to be used as reference only. To verify enrollment eligibility for a property, contact the school directly.