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$6,750,000
4 Days On Site

300 Uplands Drive
HILLSBOROUGH, CA 94010

For Sale|Single Family Residence|Active
5
Beds
4.5
Total Baths
4
Full Baths
1
Partial Bath
3,800
SqFt
$1,776
/SqFt
1954
Built
County:
San Mateo
Listed by of Sternsmith Group of Compass (650) 678-5455
Upcoming Open Houses
Tue, Apr 28, 11:00 AM - 1:00 PM
300 Uplands Drive300 Uplands Drive300 Uplands Drive300 Uplands Drive
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Mortgage Calculator

Monthly Payment (Est.)

$30,796
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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.

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Listing Snapshot
Price 
$6,750,000
Days On Site 
4 Days
Bedrooms 
5
Inside Area (SqFt) 
3,800 sqft
Total Baths 
4.5
Full Baths 
4
Partial Baths 
1
Lot Size 
N/A
Year Built 
1954
MLS® Number 
ML82044375
Status 
Active
Property Tax 
N/A
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
16 hours agoListing updated with changes from the MLS®
5 days agoListing first seen on site
General Features
Attached Garage 
Yes
Cross Street 
Redwood Drive
Disclosures 
Natural Hazard Disclosure
Foundation 
Concrete Perimeter
Garage 
Yes
Garage Spaces 
2
Number Of Stories 
2
Parking 
AttachedElectric Gate
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Total 
3800
Water Source 
Public
Zoning 
R10025
Interior Features
Appliances 
DishwasherExhaust FanMicrowaveRefrigeratorGas CooktopWasher/Dryer
Cooling 
Other
Fireplace 
Yes
Fireplace Features 
Living Room
Fireplaces 
1
Flooring 
CarpetHardwoodTile
Heating 
Forced AirNatural GasCentral
Interior 
Walk-In Closet(s)Double VanityKitchen Island
Window Features 
Skylight(s)
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Exterior Features
Pool Features 
Pool/Spa ComboIn Ground
Roof 
FiberglassShingle
Windows/Doors 
Skylight(s)
Community Features
Accessibility Features 
Therapeutic Whirlpool
School District 
San Mateo Union High
Schools
School District
San Mateo Union High
Elementary School
South Hillsborough
Middle School
Crocker Middle
High School
San Mateo High
Listed by of Sternsmith Group of Compass (650) 678-5455



The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListings™ MLS system. Real estate listings held by brokerage firms other than eXp Realty are marked with the Internet Data Exchange icon and detailed information about them includes the names of the listing brokers and listing agents. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Copyright 2026, MLS Listings, Inc..
Last checked: 2026-04-28 09:04 AM UTC

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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