265 Chestnut Street, San Carlos, California 94070, San Carlos, 94070 - 3 bed, 1 bath

265 Chestnut Street
San Carlos, California 94070
Property Price
SUMMARY
Analysis of 265 Chestnut Street, San Carlos, California 94070 is currently available with a list price of $2,500,000. The property maintains a Tear down Condition Rating (10/100), reflecting significant deferred maintenance. This property is best suited for experienced investors or developers prepared for substantial renovation work. Located in a high-demand neighborhood within the San Carlos Unified School District, this asset is categorized as a low-risk, high-reward acquisition suitable for Experienced Investors and Fix-and-Flip Specialists.
Condition Analysis
OVERALL CONDITION SCORE
Property is land value only, full reconstruction required.
Built in 1942, this property is marketed primarily as a redevelopment opportunity on an expansive lot. The interior features a severely outdated kitchen and a single bathroom with original-style fixtures and finishes. Given the age of the structure, the lack of significant renovations in over 50 years, and the listing's emphasis on the land's potential for a 'custom vision' or 'reimagining,' the value lies in the land rather than the existing dwelling.
PROSSTRENGTHS & OPPORTUNITIES
- High Available Lot Utilization
The property has a large lot size, which is more than 4 times of its living area. lot size in square feet = 14379, living area = 1300.
- Great Schools
Middle School: Ralston Intermediate School (9/10). High School: Carlmont High School (9/10).
- Expansive Lot & Development Potential
The massive 14,379 sq ft lot offers a rare redevelopment or expansion opportunity in a high-demand Peninsula market, providing a significant canvas for a custom luxury estate.
CONSRISKS & DEFICIENCIES
- Dated & Undersized Structure
The original 1942 home is only 1,300 sq ft with a single bathroom, likely requiring a complete teardown or substantial capital investment to meet modern luxury standards.
- Hillside Construction Complexity
While offering views, the sloped hillside topography can lead to higher engineering costs and more complex foundation requirements for future construction or expansion.
About 265 Chestnut Street
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
Public Facts
- Property Type
- Single Family Residence
- Year Built
- 1942
- Lot Size
- 14,379 Sq. Ft.
Interior
- Total Bedrooms
- 3
- Total Bathrooms
- 1 (1 Full, 0 Half)
Exterior & Parking
No exterior & parking available.
Utilities & Misc
- HOA Fee
- $0 / Month
Neighborhood Insights
San Carlos Unified Schools
Cipriani Elementary School
Grades K-5 • 2.2 mi
Redwood Shores Elementary School
Grades K-5 • 2.6 mi
Sandpiper Elementary School
Grades K-6 • 2.7 mi
Sensitive Facilities
No sensitive facilities data found.
Neighborhood Comparison
| Feature | Subject | Average Home | Neighborhood Ranking (50 Listings) |
|---|---|---|---|
| Beds | 3.0 | 3.5 | 50% |
| Baths | 1.0 | 3.0 | 12% |
| Square foot | 1,300 | 2,020 | 12% |
| Lot Size | 14,379 | 6,631.5 | 93% |
| Price | $2.50M | $2.73M | 38% |
| Price per sq ft | $1.9K | $1.4K | 95% |
| Built year | 1942 | 1953 | 18% |
| HOA | $0 | $0 | 50% |
| Days on market | 23 | 148 | 7% |
Pricing History
Listed for Sale
Feb 12, 2026
$2,500,000
Initial Listing












