577 N Chester Avenue, Pasadena, California 91106, Pasadena, 91106 - 6 bed, 4 bath

577 N Chester Avenue, Pasadena, California 91106 home-pic-0
ACTIVE$1,900,000
577 N Chester Avenue, Pasadena, California 91106
6Beds
4Baths
2,946Sqft
7,452Lot
Year Built
1911
Close
-
List price
$1.9M
Original List price
$2.3M
Price/Sqft
$645
HOA
-
Days on market
-
Sold On
-
MLS number
25588501
Home ConditionFair
Features
Spa
Patio
View-

About this home

We found 3 Cons,5 Pros. Rank: price - $1.90M(47th), sqft - 2946(65th), beds - 6(97th), baths - 4(65th).

This timeless Craftsman offers something few homes can: the soul of Pasadena's history paired with the freedom to make it your own. With original woodwork, vintage details, and that unmistakable Pasadena charm, the home carries the kind of history you can feel the moment you step onto the porch. Originally built as a triplex, the layout adapts beautifully for modern life and offers extraordinary flexibility: two upstairs suites can serve as private quarters for extended family, creative studios, or income-producing rentals or keep the whole home together as a single, cohesive space. Your choice. Out back, a newly built one-bedroom ADU brings clean lines and modern comfort to the mix. It's perfect for guests, in-laws, college grads, a studio, or tenants.The generous backyard ties everything together and is ready to be lived in with room to garden, entertain, or create your own compound. The hot tub and the gorgeous lemon tree are both yours to enjoy.This is not a cookie-cutter house; it's a home with layers, personality, and room to grow into. It's where the old and the new live side by side. Come see why this Pasadena property feels less like real estate and more like a lifestyle.

Price History

Date
Event
Price
11/20/25
Price Change
$1,900,000-9.4%
10/02/25
Price Change
$2,097,000-8.8%
09/07/25
Listing
$2,299,000
Condition Rating
Fair

The main house, built in 1911, retains significant vintage charm with original woodwork and period details, including the kitchen and main bathrooms which feature dated but clean fixtures and finishes (e.g., vintage stove, checkered floor, pedestal sink). While well-maintained, these areas would require substantial renovation to meet modern aesthetic and functional standards. The property benefits significantly from a newly built, modern ADU, which is in excellent condition. However, considering the primary residence's age and the need for updates in key areas to align with contemporary tastes, the overall property condition is best described as 'Fair', as it is aged but maintained, with major components showing signs of being outdated, despite the new ADU.
Pros & Cons

Pros

Historic Charm & Architectural Integrity: The property showcases timeless Craftsman architecture with original woodwork and vintage details, offering unique character and a strong connection to Pasadena's history.
Exceptional Income Potential & Flexibility: Originally a triplex, the main house's adaptable layout with two upstairs suites, combined with a newly built ADU, provides significant flexibility for multi-generational living, creative studios, or substantial rental income opportunities.
Modern & Versatile ADU: A newly constructed one-bedroom Accessory Dwelling Unit (ADU) offers contemporary comfort and broad utility, ideal for guests, extended family, or as an additional income-generating unit.
Generous & Amenity-Rich Backyard: The property features a spacious backyard, perfect for gardening, entertaining, or creating a private compound, complete with a hot tub and a mature lemon tree.
Ample Space & Configuration: With 6 bedrooms and 4 bathrooms across 2946 sqft, the property offers substantial living space, further enhanced by its flexible layout options to suit various needs.

Cons

Age-Related Maintenance & System Concerns: Built in 1911, the main house may require ongoing maintenance and potential updates to older systems (e.g., plumbing, electrical, HVAC) that are not explicitly mentioned as modernized, which could incur future costs.
Significant Price Reduction History: The property has undergone substantial price reductions from its original listing ($2.299M to $1.9M), which could indicate initial overpricing or challenges in attracting buyers at higher price points, potentially signaling market resistance.
Potential for Extensive Renovation in Main House: While the ADU is new, the description's emphasis on 'original' and 'vintage' details in the main house suggests that significant investment might be needed to bring its systems and finishes up to contemporary standards, beyond cosmetic preferences.

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