For Sale For Rent
Advertise
bedrooms
bedrooms
3
bathrooms
bathrooms
1
square feet
square feet
1,300
acreage
Acreage
0.3301
open houses
Open Houses
-
year built
year built
1942
full baths
Full Baths
1
half baths
Half Baths
0
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.
Location
Subdivision -
County San Mateo
Elementary School -
Middle School -
High School -
open houses Open houses
None scheduled.
Find out more
Tell us who you are, and we will have someone reach out to you.

By proceeding, you consent to receive calls, texts and voicemails at the number you provided (may be recorded and may be autodialed and use pre-recorded and artificial voices), and email, from Kotohomes, Wilson Leung, and their network of service providers about your inquiry and other home-related matters.

Msg/data rates may apply. This consent applies even if you are on a do not call list and is not a condition of any purchase.

MLS number: ML82029273
Listing status: Active
Listing agent: Wilson Leung #01904259
Listing broker: Keller Williams Peninsula Estates (650) 627-3700
Copyright © 2026 MLS Listings, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.   [source]
Last update: Friday, February 13 2026 at 7:15 p.m. EST
Kotohomes National