265 Chestnut Street

Welcome to 265 Chestnut Street, a rare opportunity set on an expansive 14,379 sq ft lot in one of San Carloss most desirable neighborhoods. Perched atop a hill, the property enjoys sweeping views and an elevated setting, offering exceptional potential for expansion, redevelopment, or a custom vision. The generous lot size provides ample room to reimagine the existing home, expand square footage, or create a truly special indooroutdoor living experience. Its hillside position enhances privacy and outlook, making it an ideal canvas for buyers, builders, or investors seeking a high-upside opportunity in a prime Peninsula location. Conveniently located just minutes from Hillsdale Shopping Center, Downtown San Mateo, and everyday essentials including Whole Foods, Costco, Trader Joes, and Target, the property also offers close proximity to top-rated schools, neighborhood parks, and major commuter routes. Easy access to Highway 101 ensures a seamless commute throughout the Peninsula, Silicon Valley, and San Francisco. 265 Chestnut Street presents a compelling opportunity to create something exceptional on a large lot with views, location, and long-term value in one of San Carlos most sought-after areas.

Days on Market

1 day

Current Status

Active

Original Price

$2,500,000

List Price

$2,500,000

On Market Date

Feb 12, 2026

Property Type

Single Family Home

Area

355 - Cordes Etc.

Zip Code

94070

MLS ID

ML82029273

APN

050-045-420

Year Built

1942

Stories in Building

1

Possession

Unavailable

Data Source

MLSL

Origin MLS System

MLSListings, Inc.

Bed

3

Bath

1

Parking

1

Other

SQ FT

1,300

SQ FT Source

Unavailable

Lot SQ FT

14,379.0

Lot Acres

0.330096 Acres

Cooling

Other

Dining Room

Dining Area

Disclosures

Natural Hazard Disclosure

Family Room

Other

Foundation

Other

Fire Place

Other

Heating

Central Forced Air

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.