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17,424 sqft

$1,174,000

4399 Glenwood DR, Scotts Valley CA, 95066

Price per sqft$67.38
Built in1993
Property size17,424 sqft
Property typeMulti-family

Overview

Active

Listed Jul 14, 2026

Updated 8 days ago

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 ver

$7,811/mo

Est. mortgage payment based on a $1,174,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
82054170ML

Interior Features

Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.4 Acres

Other Property Details

Association Fee Frequency
Monthly
View
Yes

Listed by Lisa Dailey-goodrich with Miritz & Bailey Real Estate, Inc
Listing Contact: 831-325-6320 

Based on information from The MLSTM / Combined LA/Westside Multiple Listing Service, Inc. IDX information is provided exclusively for consumers' personal, non-commercial use, it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information is deemed reliable but not guaranteed and should be independently reviewed and verified. Property locations as displayed on any map are best approximations only and exact locations should be independently verified. All properties are subject to prior sale, change or withdrawal, and may or may not be listed by the office/agent presenting the information. Neither listing broker(s) nor Approach Properties Premium Real Estate Services shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. 

©2026 Combined L.A./Westside MLS. All rights reserved.

Data last updated 9/28/2026

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