$1,199,000

4399 Glenwood Drive, Scotts Valley, CA 95066

Price journey

No recorded price changes. We record a move the moment we see one, and we start from when this listing entered our tracking — we don’t backfill, because the feed carries no earlier history to reconstruct. So this is a gap in our records, not evidence that the price has never moved.

18% below the Scotts Valley median of $1.5M (33 active listings)

55% of Scotts Valley listings have cut their price · half have been listed 60+ days

3beds

2baths

1,400sqft

$856/sqft

Open Houses

Sun, Sep 13·1:00 PM – 4:00 PM

Sat, Sep 12·1:00 PM – 4:00 PM

Stop by during open house hours — no appointment needed.

About this home

TWO HOUSES in rare historic setting overlooking the 1880s Glenwood Train Turnaround & bordering the Glenwood to Wrights rail tunnel! Discover a rare dual-residence opportunity perfectly blending mountain serenity, historic rail heritage & everyday convenience, nestled at the border of Scotts Valley & Los Gatos in the coveted Santa Cruz Mountains. This unique property features 2 fully independent homes surrounded by tranquil wooded views, open pastures & a seasonal creek. 4399 Glenwood Dr is a meticulously maintained & updated 3BR/2BA sanctuary offering 1400 SF of warm living space. The home sits within a fully fenced, private oasis combining peaceful seclusion with effortless access to Highway 17, Santa Cruz beaches & Silicon Valley employment hubs. 4401 Glenwood Dr is tucked privately behind the main house on it's own private right of way. This updated 1BR/1BA, 530 SF home serves as an ideal source for rental income, multi-generational living, or guest accommodations. While the residences share a private well & whole-house backup generator, they provide complete independence with separate parcels, individual septic systems, & dedicated PG&E meters. Enjoy this versatile property that seamlessly balances premium lifestyle, a prime commuter location & long-term income potential.