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

265 Chestnut Street, San Carlos, California 94070 home-pic-0

265 Chestnut Street

San Carlos, California 94070

ACTIVE UNDER CONTRACT
CONDITION: TEAR DOWN
3Beds
1Baths
1,300Sq Ft
14,379Lot Size

Property Price

LIST PRICE$2,500,000

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

Tear down
TeardownExcellent

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 The interior features a severely outdated kitchen and a single bathroom with original-style fixtures and finishes.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

8/10

Redwood Shores Elementary School

Grades K-5 • 2.6 mi

7/10

Sandpiper Elementary School

Grades K-6 • 2.7 mi

8/10

Sensitive Facilities

No sensitive facilities data found.

Neighborhood Comparison

FeatureSubjectAverage HomeNeighborhood Ranking (50 Listings)
Beds3.03.5
50%
Baths1.03.0
12%
Square foot1,3002,020
12%
Lot Size14,3796,631.5
93%
Price$2.50M$2.73M
38%
Price per sq ft$1.9K$1.4K
95%
Built year19421953
18%
HOA$0$0
50%
Days on market23148
7%

Pricing History

Listed for Sale

Feb 12, 2026

$2,500,000

Initial Listing

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