$2,500,000
265 Chestnut ST
San Carlos, CA, 94070
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 Details
Price:
$2,500,000
MLS #:
ML82029273
Status:
Active
Beds:
3
Baths:
1
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
699notdefined
Listed Date:
Feb 13, 2026
Finished Sq Ft:
1,300
Lot Size:
14,379 sqft / 0.33 acres (approx)
Year Built:
1942
Schools
School District:
Other
Interior
Bathrooms
1 Full Bathroom
Heating
CF
Exterior
Parking Spots
1
Roof
OTH
Financial
Get Out There, A Simply Outgoing Approach to Life. James Outland Jr. is one of those rare people who simply has an outgoing approach to life. No matter the activity… from dune buggy riding to skydiving to motorcycling to riding the local Pismo Beach waves… James Outland Jr. approaches life with a “just get out there and do it” kind of attitude. A zest for Life. James’ zest for life is obviously apparent in his many exciting hobbies. In his spare time, he loves riding dune buggies or hi…
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Map
Current real estate data for Single Family in San Carlos as of Feb 14, 2026
34
Single Family Listed
50
Avg DOM
1,062
Avg $ / SqFt
$2,435,188
Avg List Price
Community
- Address265 Chestnut ST San Carlos CA
- CitySan Carlos
- CountySan Mateo
- Zip Code94070
Similar Listings Nearby
Property Summary
- 265 Chestnut ST San Carlos CA is a Single Family for sale in San Carlos, CA, 94070. It is listed for $2,500,000 and features 3 beds, 1 baths, and has approximately 1,300 square feet of living space, and was originally constructed in 1942. The current price per square foot is $1,923. The average price per square foot for Single Family listings in San Carlos is $1,062. The average listing price for Single Family in San Carlos is $2,435,188. To schedule a showing of MLS#ml82029273 at 265 Chestnut ST in San Carlos, CA, contact your James Outland agent at 8057482262.
Courtesy of KW Advisors. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the California Regional Multiple Listing Service. Detailed information about real estate listings held by brokerage firms other than James Outland include the name of the listing broker. Neither the listing company nor James Outland shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. California Regional Multiple Listing Service. All rights reserved. 265 Chestnut ST
San Carlos, CA



























