265 Chestnut Street

Property Overview
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.
Home Details
- Property type
- Residential - SingleFamilyResidence
- Year built
- 1942
- Living area
- 1,300 sq ft
- Lot size
- 14,379 sq ft
- Parking
- 1 spaces
- Garage
- 1 spaces
- Stories
- 1.0
- Days on market
- 1
- MLS status
- Active
- Zoning
- R10006
Features & Amenities
Parking
- Other
Community, Schools & Utilities
Utilities
- Heating
- Central
- Water
- Public
- Sewer
- PublicSewer
Location & Neighborhood
Frequently Asked Questions
Homeowner resources
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“Reza was the best agent we have ever worked with.”— Russell & Susan McQueen
Listing Agent

