$1,199,000
bedrooms
3
bathrooms
2
square feet
1,400
Acreage
0.4
Open Houses
year built
1993
Full Baths
2
Half Baths
0
FINAL OPEN HOUSE SUNDAY (09/20/2026) before the owner takes the property off the market. 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 its 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. Enjoy this versatile property that seamlessly balances premium lifestyle, a prime commuter location & long-term income potential.
| Location | |
| Subdivision | - |
| County | - |
| Elementary School | - |
| Middle School | - |
| High School | - |
Open houses
Sep
20
Sunday
1PM
— 4PM
Find out more
Tell us who you are, and we will have someone reach out to you.
MLS number: ML82053482
Listing status: Active
Listing agent:
Lisa Dailey-goodrich
#02155959
Listing broker:
Miritz & Bailey Real Estate, Inc.
(831) 588-4528
Copyright © 2026 MLS Listings, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
[source]
Last update: Sunday, September 20 2026 at 6:09 a.m. EDT
Kotohomes National
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