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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.
Property Type(s):
Single Family
| Last Updated | 4/28/2026 | Year Built | 1942 |
|---|---|---|---|
| Garage Spaces | 1.0 | County | San Mateo |
Additional Details
| AIR | Other |
|---|---|
| AIR CONDITIONING | Yes |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Forced Air |
| HOA DUES | | |
| LOT | 0.3301 acre(s) |
| LOT DIMENSIONS | 0.3301 |
| PARKING | Underground, Garage |
| SEWER | Public Sewer |
| STORIES | 1 |
| WATER | Public |
Listing provided by Wilson Leung | 650-455-6035KW Advisors
Bay East ©2026. CCAR ©2026. bridgeMLS ©2026. Information Deemed Reliable But Not Guaranteed. This information is being provided by the Bay East MLS, or CCAR MLS, or bridgeMLS. The listings presented here may or may not be listed by the Broker/Agent operating this website. This information is intended for the personal use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated at 4/30/26 10:32 AM PDT
This IDX solution is (c) Diverse Solutions 2026.
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