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3 Beds
2 Baths
1,400 sqft

$1,299,000

4399 Glenwood Drive, Scotts Valley CA, 95066

Price per sqft$927.86
Built in1993
Property size1,400 sqft
Property typeResidential
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Overview

Active

Listed Mar 6, 2026

Updated 4 weeks ago

Discover the perfect blend of mountain serenity and everyday convenience at this exceptional dual-residence property on the border of Scotts Valley and Los Gatos in the coveted Santa Cruz Mountains. Surrounded by natural beauty, 4399 Glenwood Drive is a meticulously maintained and thoughtfully updated 3 bedroom, 2 bath home offering +-1400 SF of warm, inviting living space. Set within a fully fenced private oasis, the home combines peaceful seclusion with effortless access to Highway 17, placing Santa Cruz beaches and Silicon Valley employment hubs just minutes away. Privately positioned behind the main residence on its own private right of way, 4401 Glenwood Drive is a charming updated 1 bedroom, 1 bath, +-530 SF second home. Ideal for rental income, multi-generational living or guests, this fully independent unit offers exceptional flexibility and long-term value. The homes share a well and whole house generator, while each residence maintains its own parcel, septic system, and PG&E meters providing both autonomy and convenience. Enjoy tranquil wooded surroundings, open pastures and views of a seasonal creek from this peaceful and versatile property--an opportunity that seamlessly blends lifestyle, location and income potential.

$8,642/mo

Est. mortgage payment based on a $1,299,000 home price.

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

Additional information

MLS® ID
ML82037469

Interior Features

Bedrooms
3
Bathrooms
2

Exterior Features

Lot Size
0.4 Acres
MLS provider logo

Broker Reciprocity Courtesy of Miritz & Bailey Real Estate, Inc, Lisa Dailey-goodrich

Website E2E - Playwright - Full Name

- Phone Number

[email protected] - Email

Jim Halpert - Brokerage Name

76321 - MLS License Number

 

Data last updated 12:22 PM UTC, 9/13/2026

 

Based on information from California Regional Multiple Listing Service, Inc. as of 9/13/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing.  Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.

 

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