21860 Bear Creek Way, Los Gatos, California 95033, Los Gatos, 95033 - 4 bed, 4 bath

21860 Bear Creek Way, Los Gatos, California 95033 home-pic-0
ACTIVE$1,575,000
21860 Bear Creek Way, Los Gatos, California 95033
4Beds
4Baths
2,052Sqft
156,293Lot
Year Built
1902
Close
-
List price
$1.57M
Original List price
$1.59M
Price/Sqft
$768
HOA
-
Days on market
-
Sold On
-
MLS number
ML82024386
Home ConditionExcellent
Features
Good View: Trees/Woods
Deck
Spa
ViewTrees/Woods

About this home

We found 3 Cons,6 Pros. Rank: price - $1.57M(70th), sqft - 2052(50th), beds - 4(70th), baths - 4(93th).

So much newness! Expanded from original cabin around 2008. Since 2021: New oak floors, new whole house generator, new steel ducting, much more. Charming 4 bd. 3.5 ba. home is modernized and part of Los Gatos history. Primary plus one more en-suite bdrm! Natural light fills the living areas including the kitchen where a large center island, gas stove, and lots of counter space make cooking a joy! The primary suite opens to the back deck with beautiful views and features a walk in closet and oversized tub for the ultimate relaxation. One additional en-suite room, plus 2 more bedrooms! An inviting living room with cozy Jotul gas stove opens to the back deck where the jacuzzi awaits. What is a mtn. home without a wood-beam ceiling wine cellar? Keep your collection cool in this fun space! Steps away, a separate stand alone office space, updated in 2024 and now complete with AC/Heat, recessed lighting, and more, perfect for work-from-home, she-or-he-shed or other! Frontier fiber ready, Starlink available. 3.5 ac. lot, some usable land! Fruit trees produce in abundance, chicken coop is ready for your chickens, sun and shade, this is a truly beautiful setting! It's quick and easy to get onto Bear Creek Road and then you are just 8.7 miles into downtown Los Gatos. Los Gatos schools!

Price History

Date
Event
Price
11/12/25
Price Change
$1,575,000-0.9%
10/17/25
Listing
$1,590,000
Condition Rating
Excellent

Despite the original 1902 build year, this property has undergone extensive and recent renovations, with significant upgrades since 2021 including new oak floors, a whole-house generator, and new steel ducting. The kitchen features modern stainless steel appliances, granite countertops, and a contemporary tile backsplash, all appearing virtually new. Bathrooms are also updated with modern fixtures and finishes, such as the oversized tub and sleek vanity. The detached office was updated in 2024. These comprehensive updates ensure the property meets current quality standards with no deferred maintenance, making it feel like a newly renovated home.
Pros & Cons

Pros

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 = 156293, living area = 2052.
Extensive Recent Upgrades: The property has undergone significant modernization since 2021, including new oak floors, a whole-house generator, and new steel ducting, enhancing its comfort and reliability.
Dedicated Detached Office Space: A separate, updated (2024) stand-alone office space complete with AC/Heat and recessed lighting, perfect for remote work or as a versatile flex space.
Spacious & Amenity-Rich Lot: A generous 3.5-acre lot with usable land, fruit trees, a chicken coop, and a beautiful natural setting, offering privacy and potential for outdoor living.
Luxurious Primary Suite & Multiple En-suites: Features a primary suite with deck access, a walk-in closet, and an oversized tub, plus an additional en-suite bedroom, providing enhanced privacy and comfort.
Robust Connectivity & Infrastructure: Equipped with Frontier fiber readiness, Starlink availability, and a whole-house generator, ensuring reliable power and high-speed internet, crucial for a mountain home.

Cons

Secluded Mountain Location: While offering privacy, the 8.7-mile distance to downtown Los Gatos via mountain roads may result in a longer commute and less convenient access to urban amenities.
Historic Original Structure: Despite extensive modernization and expansion, the home's original cabin dates back to 1902, which could imply potential for unforeseen maintenance or structural considerations inherent to very old properties.
Recent Price Adjustment: A recent price reduction from the original listing price may indicate a slower market response or initial overpricing, potentially impacting perceived value.

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