$2,500,000
bedrooms
3
bathrooms
1
square feet
1,300
Acreage
0.3301
Open Houses
-
year built
1942
Full Baths
1
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 | - |
Find out more
Tell us who you are, and we will have someone reach out to you.
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
Other listings you might be interested in
$2,950,000
3 Bed •
2 Bath •
3,000 ft²
30005 Summit RD
LOS GATOS, CA 95033
$2,199,000
3 Bed •
3 Bath •
1,784 ft²
577 Creekside CT
HALF MOON BAY, CA 94019
$2,651,000
4 Bed •
2 Bath •
2,688 ft²
16999 Mcgill RD
Saratoga, CA 95070
$2,799,000
3 Bed •
3 Bath •
2,872 ft²
153 Castillo CT
APTOS, CA 95003
$3,298,000
2 Bed •
2 Bath •
2,017 ft²
20510 Brookwood LN
SARATOGA, CA 95070
$3,500,000
3 Bed •
3 Bath •
3,000 ft²
900 E Bel Mar DR
LA SELVA BEACH, CA 95076
$3,850,000
4 Bed •
2 Bath •
2,000 ft²
3803 Hamilton WAY
REDWOOD CITY, CA 94062
$2,398,800
4 Bed •
3 Bath •
2,640 ft²
16280 Oak Canyon DR
MORGAN HILL, CA 95037
$2,575,000
5 Bed •
3 Bath •
2,508 ft²
3028 Neal AVE
SAN JOSE, CA 95128
$2,500,000
4 Bed •
4 Bath •
3,403 ft²
24595 Skyland RD
LOS GATOS, CA 95033
$2,488,000
4 Bed •
4 Bath •
3,689 ft²
17864 Holiday DR
Morgan Hill, CA 95037
$3,675,000
4 Bed •
3 Bath •
2,598 ft²
19437 Via Real DR
Saratoga, CA 95070