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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 |
|---|---|---|---|
| Community | 699 - Not Defined | Garage Spaces | 1.0 |
| County | San Mateo |
Additional Details
| AIR CONDITIONING | Yes |
|---|---|
| AREA | 699 - Not Defined |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Central |
| LOT | 0.3301 acre(s) |
| LOT DIMENSIONS | 14379 |
| PARKING | Underground |
| SEWER | Public Sewer |
| STORIES | 1 |
| WATER | Public |
Location
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Listed with KW Advisors
The information being provided by Conejo Simi Moorpark Association of REALTORS® (“CSMAR”) is for the visitor's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. Any information relating to a property referenced on this web site comes from the Internet Data Exchange (“IDX”) program of CSMAR. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. Any information relating to a property, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by CSMAR and is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited.
This IDX solution is (c) Diverse Solutions 2026.
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